Hey all, this story was inspired by ticklephehe. In fact, she was kind enough to read the rough draft and gave me some excellent encouragement and feedback. Hopefully there will be a part 2. As always, comments, and suggestions are always welcome
Enjoy
The Challenge
How many was that? I lost count but I think I just had my fourth forced orgasm. The first one was achieved when my Mistress used her nylon toed foot to stroke and tease my clit. It felt amazing and my climax was very intense! She then used her ever so talented fingers to make me cum another time. But this last orgasm Dominatrix Sara used a stiff feather. I never thought a feather flicking against my love button would bring me to a ground shattering orgasm, but it sure did! I got to hand it to this one, Mistress Sara really knows how to get a girl off ha, ha, ha. But alas just like the other ones, the bitch only gave me a few brief seconds to enjoy the afterglow of these powerfully pleasurable climaxes before engaging her sharp nails to tickle my insufferably ticklish toes. Oh, my fucking GOD she made me wish I was born without toes lol! The way she flicked, jabbed, and teased up and down the stems, sides, tips, the sensitive crease just underneath them, and the webbed flesh in between my post-orgasm gumdrop shaped toes sent me spiraling into unspeakable and agonizingly ticklish sensations! I never laughed so hard and forcefully in my life and I have been tickled dozens of times by some real sadists but; umm never like this!
I suppose it doesn’t help that my feet were encased in a pair of sheer 5 toed nylon stockings. You know, the ones where each toe fits into the nylons like a glove? In these nylons my toes are very accessible to tickling as if they were bare. But nylons as I have learned the hard way, make my feet much more ticklish and this woman took full advantage of that! I can only assume that wearing these nylons was part of the “challenge” of this session which I will describe later.
Let me tell you a little about myself. My name is Jennifer. I am about 5’6”, with brown hair and light eyes. I am athletic but not skinny. I am very, very ticklish everywhere but my underarms and size 7 and ½ feet are my most ticklish spots. I have a love/hate thing about tickling and this Dominatrix here really tested my limits for sure!
In this situation, I was fully clothed with these sheer nude 5 toed nylon stockings except that the hose had been cut open to expose my crotch area. My hands and legs are tied spread eagle in a chair reclined at an angle for my Dominatrix to have easy access to my feet.
Now the soles of my feet are cocooned and mummified by plastic wrap so that only my toes are exposed and pulled up so they are taut making the soft flesh underneath my toes particularly vulnerable.
Okay, so here is the challenge I came up with to endure. First, I searched around to find a Dominatrix that was expert at tickle torture because I wanted to be pushed to my tickle limits. Mistress Sara came highly recommended and when we spoke and got comfortable with each other I offered her a challenge. I told Sara that she could only tickle ONE part of my body and if she could “break me” and make me use my safe word in under 2 hours I would pay her twice the rate of a normal 2-hour tickle session. Basically, she would have to be skilled enough to make me safe word by tickling only ONE body part. If she could do that, she’d get paid double. If, I survived the challenge and did not safe word during the 2-hour time frame she would not get paid at all for the session.
Well, Sara gleefully took up the challenge which I was sure she’d fail. I mean I didn’t think anyone was THAT good at tickling to make me safe word by only tickling one body part even if it was my most ticklish place.
In fact, instead of being intimidated by my challenge Mistress Sara actually upped the stakes and said that if she made me safe word before the deadline that I would not only pay double her rate for the two hour tickle session but I would be forced to endure an additional hour of tickling and pay her time and a half for the additional hour. In effect, I’d be paying her a substantial sum of money if I lost this challenge. Being very confident I said “sure, bring it on girl”.
Spoiler alert, I lost, BIG TIME! Come to find out that Mistress Sara has mad and I mean MAD tickle skills! She kept me on edge and outright drove me completely bonkers making me cry, beg, and laugh like a pathetic little schoolgirl. She even made me verbally tease myself AND beg for her to tickle me! It was pitiful and humiliating. She made me her tickle bitch for sure! Obviously, I definitely underestimated her….umm ingenuity.
Let me go back to the beginning. We agreed that Mistress Sara could take some time to first locate and find the area that she would focus her tickles on for the challenge. This exploration time was not part of the 2 hour challenge because, to be fair, Sara needed to get a good spot because this would be the only place, she would be allowed to tickle me for the challenge, so I gave her the proper time to explore my tickle zones.
At the start I was bound spread eagle but not yet gagged. Now someone really good must have schooled Sara in the art of bondage because after she tied me up I had no play at all. I realized fast that I wasn’t going anywhere. I’ve been bound many times before, but her bondage technique made me a wee bit nervous. I mean, I’m a stronger than average girl but when I pulled on my ties I legit couldn’t budge an inch. If she was trying to hold me captive like in a kidnapping, I doubt I’d be able to escape even if my life depended on it. Truth be told it was kind of scary, but I totally trusted her and was awaiting my tickle torture with bated breath.
Sara then investigated my bound body for all the usual tickle spots and quickly discovered how ticklish my underarms are. From the jump I could tell this bitch knew what she was doing, and she tickled and teased my armpits really well employing a whole range of techniques. Most ticklers often use their nails to alternate between hard and light tickles into the armpit. Both ways send me howling. But these kinds of tickles generate a uniform sensation. Sara employed a technique that offered duel tickle sensations. She used her thumb nails to softly but firmly dig into the tissue in the middle of my armpit and tickled it using tiny circular motions. At the same time, she danced and flicked her other nails along the bottom and sides of my pits. As she did that, oh man! She got me singing notes of laughter I never knew I could reach! Those two different tickle vibrations, firm digs with rotating nails in my pit hollows and light scratching along the sides excited my armpits like nothing else and I crumbled into ear splitting laughter.
Jennifer: Oh ha ha ha ha ha ha ha aahhh ah ha thahahaht tihehehh tickles soohohoh bahahahahd ohohoh ha ha ha ha!
I couldn’t take it and almost safe-worded after only a few minutes. I was in complete hysterics. What made the tickling worse was her verbal taunting (more on that later). I couldn’t stand being reminded how helpless I was or how ticklish she was making my armpits. I must say, a good verbal teaser can make me way more ticklish and Sara is a real pro there to.
I thought whoa, if Sara chooses the armpits, I might be in a whole lot of trouble. But she kept exploring other spots and she made me laugh like a crazy woman on all of them because number one I am dreadfully ticklish everywhere and number two she’s really, really good at exploiting tickle spots. I remembered saying to her after she let me rest before moving to another part of my body “damn girl, you are quite the tickler, aren’t you? Those nails are something else! I think I made the right choice.” I said confidently that “I’m still going to win, but this is going to be fun”. I just didn’t know that the word “fun” would have such a different meaning after this session.
Then she got to my feet. Now before the session began, she insisted that I ware five-toed pantyhose. I never heard of them before really, but she put them on me and actually it was kind of hot. She took off my heals and carefully slipped the nylons on but curiously she then cut a big hole in the crotch area. I thought at the time she did this because she wanted access to my inner thighs in case my feet were not her choice tickle zone, but I was wrong there too ha, ha, ha. Once the stockings were on, she probed my feet with her nails and I just about jumped out of my skin when she tickled them! I don’t know if it was the sharpness of her nails or how fast she could move them or what, but I have never felt so God darn ticklish on my feet before. I swear, a complete idiot that never tickled anyone could turn me into a giggling mess by touching my feet, but this girl was setting my lungs on fire with the tickling she was putting to my arches and soles. I was begging and pleading like I haven’t done in a long time and I’ve been tickled by lots of skilled male and female Domes before. But this girl was in a league all her own.
Furthermore, during this exploration phase, I found out how sadistic Sara is because when I was wailing away in ticklish hysteria and could barely breathe from her nails skittering along my arches instead of easing up satisfied that my arches and soles were extremely ticklish and a candidate spot the bitch went and dug her nails right under my toes! Well that was it! My eyes flew wide open as if I just saw a ghost. I let out a yelp from hell and a blood curling scream before my lungs ran out of air. I just held my jaw open like I was catching flies and wheezed pathetic cries of mercy mired in a wave of exhausting mirth.
“Pleahehehe (gasp) pleaheheh…stoh.(gasp).ohhophahaha”was all I could get out. I tried to beg for mercy, but no sound came out of my mouth. I reflexively curled my toes down hard on her nails trapping them in there under my toes hoping to stop their tickling advances.
Sara: Oh no, no, you don’t young lady. Gimmie back my nails so I get at these little toes! There that’s better. Coochie, coochie coo! Bad little girl trying to stop my tickle nails from getting your little tootsies (evil smile). Naughty, naughty.
Sara easily gained back control of her nails by quickly pulling back on the big toe freeing her tickle weapons. Now able to move, she concentrated the very tips of those sharp nails on grazing and tickling that tender tickle spot along my toe stems just under my toes with a focused tenacity. Helpless now to stop her talented talons from wreaking havoc on my ticklish tootsies I was kept in silent laughter for a good while longer until she let up her pace and allowed me to take in some air.
When I did finally breathe some air into my oxygen deprived lungs, she started right back up again and wiggled those damn nails faster and harder under my toes only this time with my toes held back I couldn’t squeeze them down and I immediately screamed, vibrated my leg up and down as much as my bonds would allow and swooned into a hyperventilating laugh after a few seconds. Sara had a big ol’ smile on her face at my reaction, the heartless bitch. She was toying with me realizing she hit a jackpot tickle zone. I was sure she was going to tickle me to death right then and there! She verbally teased me too.
Sara: Awe I think it’s your little tootsies that are so ticklish girl aren’t they, aren’t they? Oh yes, they are. I think I’ve found your spot and the one I will tickle to win this challenge. Unfortunately for you I am an expert toe tickler. Coochie, coochie, coo little Jennifer. Tickle, tickle, tickle Jenny’s ticklish little toesies .
Mind you I HATE being called Jenny lol! Now I’ve been tickled on my toes before many times and they are very, very, ticklish. Experienced ticklers have had no trouble finding and exploiting my toe area, and a good tickler can really make me suffer by tickling my toes in just the right way. But, every time (before Sara that is) after a while like most tickle spots, my toes would get a little desensitized and the tickler would invariably move on to another zone. So, I figured Sara wouldn’t be able to keep me laughing for the two-hour challenge if she only focused her tickles on my toes. Nope! Wrong again ha, ha, ha.
After tickling all parts of my foot, Sara decided she would direct her attention on my toes and said she could easily keep me in hysterics for the two-hour duration and make me safe word by assaulting my tender planter digits. To be able to devote her tickling on just my toes, she wrapped the length of my soles and ankles tightly with plastic wrap and pulled up on the wrapping to make my sole taut. With my feet bound in this position it made it difficult for me to flex my soles and arches to scrunch my toes in protection, so they were very vulnerable. Because my feet were pulled back so tightly, I could barely wiggle my toes. This was some serious foot bondage.
Sara: Okay Jennifer dear now let’s begin your challenge. Just be clear on the terms. I will focus my tickles only on your toes and tickle them until you utter the safe word “Gold”. If I do that, I will win double my normal fee and get to tickle you for an additional hour at time and a half my fee. Is this correct?
Jennifer: Yes, Mistress Sara that is correct. You can use any tools you wish but you can only tickle my toes during the 2 hours”.
Sara: Oh honey, the only tools I’m going to need are my fingernails. I’m afraid you will safe word after about an hour. You’re pretty tough judging by my exploration time and have good stamina but you are not that tough, especially after I prime you in my special way ha ha ha.
Jennifer: Prime me? Not sure what that means but it can’t involve tickling me anywhere else but the toes.
Sara: Oh, I know that darling. My primer won’t tickle I promise. I will set the timer on my phone when I begin tickling you. But I’m not going to tickle you just yet (evil smile).
Not exactly sure what she meant I saw Sara take her shoes off. I assumed she wanted to get more comfortable before she engaged in tickling me. But then she raised her nylon foot up towards my spread and exposed crotch. Wow what a pretty foot she has! They look about my size 7 but maybe a bit smaller and I think her toenails were painted red. It was hard to tell because she had on these sexy black nylon stockings. But she has really deep arches and elegant looking toes.
Oh my, her toes are rubbing up my crotch and up against my vagina. It feels so good. Now Sara is kissing my toes gently and using her tongue to slide up the stems and glance along the tips. It tickles only a little and I smile softly in response.
Jennifer: Hmm, are you planning on lickling my toes to torture me? I must say I do enjoy it. But I don’t think you’ll win this way (giggle giggle) hmm ha ha ha even though it does tickle a bit.
Sara just smiled at me as she continued her licks and soft nibbles on my toes. But now I started to feel her own toes enter into my vaginal area and petting the labia flaps. The smoothness of her nylons combined with the softness of her tongue on my toes is getting me real horny.
I started to get a little wet and sensing my wetness Sara began to stroke my clit with her toes very gently and softly. I reflexively moaned and sighed. Almost as if on cue, Sara took the big toe of her other nylon clad foot and penetrated me with it; back and forth, back and forth like she’s fucking me with her big toe. It felt incredible! She then used her toes to more aggressively stimulate my clit as my vaginal area became increasingly moist. And oh, watching the tongue of her pretty face licking my toes so passionately and lovingly was one of the hottest things I’ve ever seen. But when she started to talk to me that is when all hell broke loose!
Sara: Hmm Jennifer darling your toes taste so good. They are so very pretty. Not a dry piece of skin anywhere on them. I think you like Sara’s tongue licking up and down you widdle toes huh? I think so. You feel so wet down here baby. You like my toes up your snatch honey? Do you want more huh, sweetie? Do you want Sara’s tootsies to make you cum? Is that it?
I immediately responded: “Oh hell yes! Keep fucking me with your toes Sara (moans and sighs). It feels so good!”
I got to tell ya, my pussy was dripping like a busted water pipe as her smooth nyloned big toe was fucking me in and out fast and hard and her other nylon toes were stimulating my clit something fierce. Incredibly her toes were as agile if not more so than fingers. Now I’ve had my share of some excellent lovers, both men and women, who brought me to powerful orgasms, but this woman was about to make me squirt a ton of cum by using her toes! I didn’t think that was possible. But there I was; moaning and grinding my hips like a dog in heat helping her toes fuck me. I was completely lost in a sea of pleasure. Feeling smooth nylon toes on my clit and in my pussy coupled with Sara’s warm tongue and mouth sucking and licking my feet and toes was overwhelming. With the 5 toed pantyhose she was able to easily snake her talented tongue in between my toes which again kind of tickled but felt so good and amplified my sexual pleasure. I think I was actually turned on by hearing myself giggle softly in response to her teeth and tongue slurping around my toes as my clit was on fire and becoming engorged.
Sara: Hmm your toes taste so good (slurp, slurp, lick lick). Are you gonna hmm (lick, lick, nibble, slurp) cum for me Jenn baby huh (lick, lick, slurp)? Do my nylon (long lick up the toes) umm toes against your (lick, slurp, lick) clit feel good my dear hmm (nibble, lick, slurp)?
“Oh my GOD YES!” I cried in earnest. My eyes rolled in my head and I was arching my back and thrusting my hips wildly towards Sara’s toes digging and grinding relentlessly on my clit. Just then, Sara reached up and undid my blouse and bra to expose my tits. Then she pulled one of her nyloned foot from my pussy and started to rub against one of my breasts. I didn’t even notice that foot coming towards my naked mounds but as they landed on them, she spread her nylon big toe and wrapped my nipple in between her big and second toe and tugged on it gently. It felt amazing! The wetness of her nylon foot up against the nipple of my breast was so stimulating and caused my already rock-hard nipples to become even more erect and prominent. I let out a deep sigh of passion and pleasure as her moistened toes then wafted back and forth across breast. I felt as though three different lovers were attending to me.
As Sara was worshiping my feet and using her own nylon toes and feet to pounce on my clit and tits, she verbally teased me.
Sara: Now (slurp, lick, slurp) beg me to tickle your toes baby. If you (lick, slurp, slurp) beg me to tickle your toes without mercy (lick, lick, slurp, slurp) I will make you orgasm honey. Beg me with all your hmm (slurp, slurp, lick, lick) life to tickle your toes and I’ll let you orgasm. But you gotta hmm (slurp, slurp, long lick, lick) beg for the toe tickles first!
Well my clit was on fire and I never wanted to cum so bad in my life, so I did the unthinkable and begged Sara to let me orgasm just as she asked. It was quite embarrassing, but this crazy talented bitch was not giving me any choice at all! I was in a deep sexual trance with no way to escape, not that I wanted to. Bottom line is that Sara had me right where she wanted me, and she knew it!
And so needless to say, I begged ! I begged with all my heart! “Oh GOD okay, okay! Sara please, oh, oh tickle my hmm (biting lip) tickle my toes. I…I, oh shit right there…please I beg you, hmm (huge passionate smile) tickle torture my…OH GOD YES!”
Sara: Your what? Tickle your (lick, lick, slurp,) what honey? What do you want Sara to tickle? (furiously stimulating the clit with her nylon toes).
“OH, OH, JESUS! TICKLE…OH GOD..TICKLE MY…HMMM YES! MY TOES! TICKLE MY TOES! Tickle my ohh ohh GOD… TICKLE MY TOES …PLEASE!!”
Sara: Tickle your toes huh? Do you (lick, lick, slurp, nibble) want me to tickle your toes mercilessly? Is that what (slurp in between the toes) you want me to hmm (long lick along the toes) do?
Sara’s foot and toes were loving on my clit so artfully and relentlessly I screamed and begged for my poor toes to be tickled just as she instructed. I had no resistance left. My libido was too jacked up. I needed to release the enormous sexual energy building inside me, and I whined and begged again like she asked. It was so humiliating!
“YES! YES! TICKLE MY TOES MERCILESSLY! MERCILESSLY! OHHH GOD I WANT TO CUM”! I couldn’t believe my own ears! I was literally begging this woman to tickle my feet and toes without remorse or quarter. I simply could not control my will or thoughts. All I wanted to do was orgasm all over this woman’s foot stimulating my clit. It was so intense!
Sara: Good girl Jenny! Mistress Sara will make you cum now.
All I remember after that is the feeling of what appeared to be the nail of her nyloned big toe graze the tip of my clit several times. After which my body exploded into one of the most intense orgasms I’ve ever had. My hips thrust forward with such force I felt the restraints dig into my thighs. I let out a scream of pleasure so animalistic the volume rattled my teeth. It was definitely a very prolonged orgasm! I experienced several waves of pleasure coursing through my body as I convulsed for several seconds. It was incredible! Then as I was recovering, I felt Mistress Sara stroke my lightly sweaty hair from my face with her nails. She kissed me passionately on the lips which I returned in kind, thanking her for that enormous feeling of pleasure.
Sara: Hmm, did you like that Jennifer? I think you did. My nylon foot is absolutely drenched ha ha ha. I felt a little tickle to my own nylon toes from the force of your pussy juice squirting all over them ha ha ha. Quite remarkable indeed.
Wheezing and still out of breath, I said “oh my God that was incredible Sara! I don’t think I ever came so hard in my life ha ha ha. Whew. That was so intense. I don’t often squirt like that but based on the orgasm you gave me, I’m certainly not surprised I did ha ha ha”.
Sara: Good! Now that my toes have given you such pleasure my nails here are going to reciprocate and pleasure your toes (wiggles her sharp nails in front of Jennifer’s face). After all dear, didn’t you beg me to tickle your toes just a moment ago? And to tickle them without mercy?
Jennifer: Oh, holy shit NO! Don’t! Don’t do that. Please don’t tickle my toes. I..I..didn’t mean it. Oh God please, I’m too sensitive right now (I pathetically begged knowing full well what her plan was all along).
Sara: No? Oh, but dear you pleaded with me so convincingly to tickle these toes of yours that I must do so right now (evil smile). So here you go. Coochie, coochie, coo Jennifer’s little toes. Tickle her toes, my sharp little nails. Tickle them good just like Jenny asked you to do. Kitchie, coo, kitchie coo.
Sara set her timer now because she is about to unleash a fury of toe tickles that will have me breathless in minutes.
First, she used all her nails to gently flick and tickle the tender stems of my medium sized toes on both feet. She concentrated the tips of her sharp nails near the top of the fleshy part of the toe stems. The nails moved quickly but gently at first. However, because my nerves were so heightened and sensitized by my incredibly powerful orgasm just moments ago her toe tickles sent ticklish waves through my toes the likes I have never experienced, and I let out a torrent of feverous laughter!
“OHNOO….hahahahahahahahahaha…(wheeze,gasp)…thahahahahat..hahahahahahahahtickles soohohohohoho bahahahahad! Ahahahahahahahahhahah!”
I slammed my head back down on the soft headrest of the chair and laughed dutifully and powerlessly. Sara then took one set of nails and tickled across the middle of my toe stems in a horizontal motion while the other set of nails continued to parade up and down the length of my toes. Long slow tickle strokes up followed by fast skittering flicks as they reached the tops of the toes and back down again. Changing patterns constantly. The fact that she could move each of her fingernails to create such different tickle patterns was amazing! I thought I was being tickled by several sets of nails not just two and I was beginning to regret my “bet” with this very talented Mistress.
“Hahahahahahahaa..stoohohohop..hahahahaha..ohohohoh..thehehehehe toehohohoes..nothahahahaha.thehehehere.hehehehehahahahahahahahahaha.”
I was beside myself begging like a wimpy little bitch. I would normally be able to take a little bit of toe tickling especially this kind of gentle teasing of the toes, even though they are one of my worst spots. But this was different. My oversensitive nerve endings from the orgasm gave the fuel to this tickle fire unleased upon my toe flesh and the smoothness of the nylons were just putting gasoline on that fire. Sara’s fingernails moved with such speed and grace that the nylon fibers were scratching my sensitive toe flesh in unison with the tips of the nails. It was like a tickle echo chamber; a fingernail scratch, followed immediately by a nylon itch up and down and across my ticklish toes. It was maddening! And the verbal teasing was just sending me over the edge.
Sara: Hmm kitchie, kitchie, coo little toes. Oh, I know you love Auntie Sara’s nails ticking and tickling your ticklish widdle nylon tootsies huh Jenny baby? Listen to you laugh as my tickle nails go up and down your toes, and now across the toes. Hmm, yes, tickle, tickle, tickle the toes. The nylons make it tickle more, huh? Hmm, I’m so glad I made you wear these special nylons. They help my fingernails that are so good at giving Jenny the tickles she wants on her toes! Coochie, coo, coochie coo little toes. Tickle, tickle, tickle (big evil smile).
I was screaming now in a tickle panic the likes of which I have never done before. The combination of her nails tickling against the smooth nylon fabric was simply unbearable. I tried to wiggle my toes a little or curl them down but the angle of my arched foot by the plastic wrap made that impossible to be of any relief. My toes were prisoners to her nails and stood there helpless to her tickle administrations which were as relentless as they were precise. I was in tickle hell!
ohhhahahaha…(gasp) nomohohohrehahahah..(gasp)..I screamed. I was in tickle agony and would have done anything for her to stop those nails tickling my toes. But my fate was sealed. Sara was going to tickle my toes until I safe worded. I know she will stop at nothing to win this challenge and I feared I was already losing the battle. The tickling sensations were beginning to overwhelm me, but I tried to just embrace my sub-side and take it. Well that strategy didn’t last too long as I now felt Sara’s evil nails start to dig and wiggle into the tender space right under my toes!
Almost as if she felt my desperation, her sharp nails plunged into the delicate area at the top of the ball of my foot and nestled into the soft fleshed canal right at the base of my toes. The fingertips of the nails rested along the ridge of the toe line providing the fulcrum for the sharp edge of Sara’s nails to wiggle and scratch the thin nyloned skin residing in the region connecting the toes to the ball of my foot. Her nails gyrating in this area elicited ungodly ticklish sensations. It’s as if her nails were perfectly designed (and skilled) to fit snuggly into this spot for the purpose of stimulating and tickling this murderously ticklish area!
Not surprisingly, my eyes widened, my mouth formed a perfect “O”, and I let out a screech of laughter before my head slumped down towards my chest and I slipped into silent laughter. I tried to speak, beg, plead but all that came out was
”ohhahh..(silent)..nohohoh..(silent)..NO! (wheeze, gasp) NOT..NOT THERE! hahahaha (silent gasp)….OH PLEASE (silent wheezing)!!
Sara smiled triumphantly and with a snide snicker in her voice said “Oh, really? Not here? Are my nails tickling you right here under your tender little toes Jenny pooh? Hmm, yes, I think they are! I know someone who has some very ticklish toes! I think you love to be tickled right here just under your toes! But this is just one foot. Let’s see if you like it more if I tickle BOTH feet right here where you love it so much. Won’t that be nice? I bet it will tickle very much (evil grin). Kitchie, kitchie, coo. Tickle under Jenny’s toes on both her feetsies little sharp tickle nails. Tickle under Jenny’s toes right here. Come on now coochie, coochie, coo her right here under her toes. Afterall, she begged us to tickle her toes. Didn’t she? Yes, she did! She just loves her toes tickled, so coochie, coochie coo under the toes!
The evil bitch knew I was tail-spinning into silent laughter and wanted to send me over the edge by doing the exact same thing to my other foot. Smiling cruelly, she clawed her fiendishly effective tickle nails under the toes of both feet. I swear I am never going to wear nylons again during a tickle session. A really good tickler would destroy me in these hose same as this woman is now. With the double underneath the toes tickling I was losing all control, coming in and out of silent laughter for what seemed like several minutes. Her sharp nails glided and dug in and out periodically under my toes, while also occasionally nipping at the toe stems to keep me off balance only to return to pulse and jab her talons softly but firmly against the absurdly ticklish spot underneath my toes. She was driving me into a tickle induced state of lunacy. These were not fun tickles. No, these tickles were causing my nerve endings to implode, and I could barely stand it any longer!
I didn’t know how much time had passed but I was confident I was almost at the end of the two hours. I thought if I could just hold on a little bit longer, I would make it and win the challenge. Suddenly and curiously Sara eased up her tickling and pulled her nails from underneath my toes and simply flicked her fingertips along the tops of my toes, almost massaging them. I welcomed the reprieve and was hopeful I had endured the worst but alas my hopes were completely dashed when I heard Sara tease me again.
Sara: Oh, Jenny darling you are doing so well! You haven’t yelled your safe word yet and it’s been a full 30 minutes! You have wonderful stamina. Because you’ve done such a good job, I’m going to stop tickling you, shut off the timer here and make you cum again. Wouldn’t you like that?
I thought to myself OMG, you’ve gotta be kidding me! I’ve only suffered for a half hour of her tickling? When I heard that my heart sank, and I realized I am so screwed and thought about giving up right then and there. I almost used my safe word a few moments ago when this bitch was vibrating her nails under my toes and I thought for sure she knew I was about to give up, when she stopped her tickling advances. I didn’t understand it at the time, but this was Sara’s plan all along. She wanted to break my will so badly and completely that the way to do that was for her to have ultimate control over my reactions, body, and mind.
Sara: Yes dear. Here you go. Let Auntie Sara make you orgasm again sweetheart. There now, that’s so much better isn’t it? How do my fingernails feel as they dance on your pussy? You like them on here huh baby? Hmm better my nails fingerbang your pussy than scratching and tickling your poor toes hmm honey (evil smile)?
As soon as her fingers entered my pussy and landed on my clit, I let out a moan and a sigh as I felt such intense pleasure. She went right for the golden love button as my pussy was still sopping wet from my last orgasm and the subsequent tickling that always arouses me. But what a contrast from the cruel tickling on my toes just moments ago. I arched my back and moved my crotch towards her loving hands as they flicked along the edge of my pussy lips and stimulated my clit. This woman must have finger fucked hundreds of women because boy oh boy did she know her way around a vagina hahaha. My pussy was on fire in seconds and longing for her to make me cum again. I bit my lip and moaned louder encouraging her towards making me orgasm.
Sara: Hmm, feels good baby? You know, I could have made you use your safe word back there if I continued to tickle underneath your toes. You know that right? (stimulating Jennifer’s clit harder).
Jennifer: Hmm, yes..oh yes. I know that. Oh God (sighing and moaning), please..right there!
Sara: I want you to admit that I could have made you give up by tickling underneath your toes. Say it and I will make you cum so fucking hard and long! Coochie coo Jenny’s clit, coochie coo.
Jennifer: Oh Jesus! Okay, okay. You..oh God.. you could have..hmm (biting lip)..made me give up…OH GOD…ahh yes..give up by tickling…ahh ohhh please fuck me more…by tickling underneath my..ohh yeah, ohh yeah..my toes! OH GOD!
Sara: Good girl! Such an obedient girl. Now I want you to beg me and ask Mistress Sara, to please tickle you right in between each of your toes with her nails and make you safe word. Say that and I will let you orgasm.
I gotta hand it to this woman, she is making me beg to be tickled with such great intensity that I safe word and lose my challenge. I mean what an absolute mind fuck! She wants me to beg for my own demise. I know once I orgasm and she tickles me in between my toes I will have a very difficult time resisting and I don’t think I can hold out for another hour and a half with her tickling my toes, especially not after I orgasm like I’m going to be forced to do again. My nerve endings will be shot, and I’ll have virtually no resistance left against her skillful and agile nails. I just know my toes will be way too ticklish and I’ll crack for sure. The question is how long will she tease me and prolong the inevitable? How long will she make me suffer the tickle torture which I know is coming? I feel deflated yet very excited about the prospect of being so mercilessly tickle tortured. I mean this is part of the reason why I came up with this challenge. I wanted someone to push my limits and really torture me! Well, looks like it’s happening now.
Sara: Say it baby! Beg me to tickle you in between your cute ticklish little nylon toes. Beg me and I’ll continue to fuck your pussy and clit to make you cum, and cum hard!
Sara stopped stimulating me to let me know she is serious and wants me to beg her as she asked. I felt so powerless and humiliated but having no choice I complied.
Jennifer: Oh no don’t stop please, Sara (pant, pant). Make me cum. Please make me cum (pant, pant).
Sara just grinned disappointingly at me and said “well then if you want to orgasm then beg me! Beg me you tickle slut! Beg your Mistress to tickle right in between your toes!” She commanded.
Jennifer: Okay. Okay. Mistress Sara, please I beg you, please, please tickle in between my toes. Please I want you to tickle in between my toes so badly. Please!
Sara: Hmm, how long do you want me to tickle you in between your little toes Jenny darling?
(Oh God do I HATE being called Jenny but what can I do?) “Hmm, oh..umm..tickle me there until I.. until I..”
Sara: Until you what? (stimulating Jennifer’s clit again and finger fucking her harder). Tell me or I’ll stop fingering you (singing chiding voice).
Jennifer: Until I..say my..until I say my safe word. Tickle my toes until I safe word..PLEASE (pouting face), OH GOD! YES! DON’T STOP! RIGHT THERE! I’m gonna cum so (panting and moaning) so, OH GOD! SO MUCH! AHHHH!
As I felt her artful fingers stimulate my engorged clit my mind took off to a destination of pleasure I didn’t know existed. Sara grinned widely, nodded her head and said “As you wish darling”. Then her fingers caressed my clit again and I was catapulted into a fantastically long and hard orgasm. I squirted pussy juice again as wave after wave of pleasure coursed through my body. As the orgasm raced through my body, her fingers no longer were needed on my clit and she simply watched my body writhe in orgasmic convulsions. The aftershock of orgasmic energy made me dizzy and I gasped several times to try and slow my breath and come back to Earth.
Jennifer: Holy shit! What the fuck was that? How, (panting and gasping) whew, how did you make me cum so fast and hard? Oh my God that was soooo intense. My compliments to the chef ha ha ha.
Sara: Oh, why thank you love. It’s actually quite easy to make a girl orgasm like that after she’s been tickled to the brink of madness as you just were ha ha ha. All the nerve endings in the erogenous zones are on high alert and all it takes is the right stimulation to unleash their fury. Glad you enjoyed that because now unfortunately, I am going to have to tickle in between your nylon toes with such a ferocity that you will safe word within minutes. But I don’t want that to happen, so I am going to have to gag you now. Oh, I’m perfectly aware if you say the safe word I automatically win the challenge, but I know I am going to win anyway I just want to make you suffer more and I don’t want to be gentle with your toes. I want to tickle them savagely and I can’t have you ruin my fun by safe wording to soon. So, here is what I am going to do. I’m going to take off one of my nylon stockings here (Sara unclips the stocking off her right foot from the garter belt) and use it to first wipe your pussy to get it nice and wet with your own love juice. There we go (Sara dabs the stocking fabric onto Jennifer’s soaking wet mound making the nylon very moist and soppy).
Now I’m going to gag you with this nylon stocking soaked in your own cum juice hahaha. Hmm lovely!
Jennifer: At that moment before I understood what was happening Sara stuffed that balled up nylon stocking wet with my own orgasm tang in my mouth and secured it with a ball gag. “NO!” Please don’t gag…“me..muphhphph”. As I tried to beg not to be gagged, the bitch stuffed my mouth too quickly to complain. I tasted my own cum as I inadvertently bit down on the nylon trying to free if from my mouth. I felt so violated and humiliated. And I have to admit I was a bit nervous at that time. There was a part of me that did not want Sara to tickle in between my toes because I know how bad it’s going to tickle me especially after the ground shaking orgasm I just had and now I wasn’t going be allowed to beg much less say my safe word.
Sara tapped her chin with her pointer finger as she started the timer again and mused: “Now, let’s see where should I begin? I think I’ll tickle in between your second and third toes here on your left foot. Gimmie these toes here. Tickle, tickle, tickle, in between Jenny’s tootsies. Does my fingernail tickle you here?”
Gently pulling my second toe to the side exposing the space in between it and the ring toe she carefully scratched a nail along the nylon meshed webbed space between these two toes. I motioned “NO” with my head and eyes as the gag prevented my verbal protest. And as soon as the nail made contact with the nylon covered flesh and wiggled there my eyes flew open my head lurched forward and I screeched into my gag with ferocious hilarity. It was brutal! “Mphhphahahahahahaha”. I felt that I just got electrocuted with a lightning bolt of tickles as I tried desperately to bring my toes together and stop her nail from its evil tickle path, but Sara held these toes apart easily. I had no leverage at all.
She laughed to herself knowing she hit a good spot and moved to tickle the space in between the ring and forth toe. Another maniacal scream of laughter tried to escape my gag as I felt Sara’s slender sharp fingernail tantalize and tease this sensitive area. It always amazed me how one finger tickling such a small space could inspire such unendurable tickling sensations causing me to explode in involuntary laughter so easily.
Sara: Oh, good lord Jenny dear how incredibly ticklish you are between these toes! Hahaha, such a tickly widdle girl you are hahaha. Kitchie, kitchie, coo in between these little tootsies. What about the space in between your fourth toe, and baby toe? Do you think this place will be ticklish? Huh, my slutty little tickle bitch? Answer me you tickle whore. Nod your head and tell me if in between your pinky toe is ticklish (cruel evil smile).
The evil Mistress paused for a second to separate my pinky toe from the fourth toe and wiggled her sharp index fingernail in a mocking fashion just above the gapped area informing me she is about to tickle the crevasse between these toes. Seeing her fingernail ominously wagging above my incredibly sensitive toes, I nodded my head affirmatively to indicate “Yes” your fingernail will send massive tickle derived sensations if it scratches in between my fourth, and baby toe. It will indeed tickle like crazy!
Sara: Hmm, I thought so! Usually baby toes are quite ticklish. Kitchie coo, kitchie coo pinky toe! Enjoy my sharp fingernail coming to tickle you (she said in baby talk voice). Coochie, coochie, coo!
Sara did indeed position the edge of her tapered index fingernail into the crease between these two toes and glided the sharp nail across the tender webbing laying beneath the surface of the sheer nylon fabric. I gasped and then hollered a fit of laughing torrents cruelly silenced by the tight gag enveloping my mouth. I quickly started to laugh uncontrollably but the lack of sound escaping the gag did not hide the incredible tickle panic my body was experiencing. Sara’s fingernail scratched and tickled the webbing between these two toes and then proceeded to pull back on the littlest toe to tease and play with the insanely ticklish crease just under the bend of the pinky toe which I never knew was so God damn ticklish! As she tickled and gnawed at this very tender spot, I let out another involuntary scream and whipped my head side to side trying to escape the “out of this world” tickle sensations as the nail invaded the ticklish recesses of the pad and wrinkled fold of skin underneath my poor baby toe. It was incredible how bad it tickled!
“Mhahahaha (silent gasp) hahahahahaha (wheeze, gasp) uhhauahahahaha”
Sara’s powers of observation from tickling dozens of women are so well-honed because realizing immediately that she hit a particularly good tickle spot she exacerbated my state of tickle agony she teased me.
Sara: (tilting her head to the side like George Clooney does in so many of his movies said in a singing like chiding voice), oh my goodness, someone’s widdle pinky toe is so very ticklish. I think Jenny wants Sara’s tickle nails to really tickle this pinky toe, huh? Nod your head again like you did before and encourage ALL my tickle nails to tickle in between and all around your baby toe… baby no pun intended hahaha (she said with an evil chuckle and smile).
I instinctively shook my head “NO” and wailed unintelligibly for her NOT to tickle my baby toe anymore. My head was spinning, and my lungs burned from laughing so hard and forcefully. However, Sara was not pleased by my “answer”, became very angry and decided to punish me severely!
Sara: NO! You are shaking your head “no” to me? Are you fucking kidding!? You are defying your Mistress? Oh, I see. You must really want to be tickle tortured huh girl? Okay you asked for it! Do you remember how bad my nails tickled underneath your toes? Well I’m going to use these sets of nails to tickle underneath that delicate area right under your toes (waves her red nail polished fingernails into the air for me to see) and these sets of nails to tickle and tease in between all your toes. I will unleash holy tickle hell on your toes now! You are a disobedient bitch! You will safe word in mere minutes, but I won’t hear it through that gag. You will most likely pass out from silent laughter as you run out of breath. And when you wake up, I’ll do the exact same thing again. I’ll teach you to disobey me. First, let me tie your baby toe and big toes so I can spread them out nice and wide.
I was shocked by Sara’s display of cruelty. It was such a small, unintentional, and innocent bit of defiance caused by tickle induced delirium, but it didn’t matter. She wants to torture and humiliate me pure and simple. All she needed was a little pretext to carry out her maniacal plan of utter conquest. She knows she has totally broken me. Both her and I know I have lost the challenge even though I have not technically used my safe word yet. It doesn’t matter because Sara knows I will speak it the moment she removes this gag. She is just focused on humiliating me and completing my torture.
With that, Sara looped a thin piece of string around the baby and big toes and tied them to slots on the side of the chair so that my toes were spread and completely helpless to pull together or scrunch up. My toes are doomed to be tickled. Now I am not ashamed to admit that for the first time in my life I was really scared! I mean legit scared!
My toes now tied and utterly helpless, Sara begins the ruthless torture. Framing her left hand as a “claw” she hovered right over my flayed-out toes pointing the tips of her nails to pierce directly in the creases between them. Smiling cruelly, she teased me.
Sara: Here come my nails to tickle righhht in between all of your wonderfully spread nylon toes on this foot (left one). Your toes wrapped in these special glove-like nylons make getting in between them so very easy and we know how much more ticklish your toes are in these nylons.
She was so right. I think these nylons made her tickling machinations on my toes so much more ticklish because of both the nylon material and the easy access to the areas in between the toes. Continuing with her verbal teasing, Sara said
Sara: And these nails over here (wiggled in the air approaching my right foot) are going to torture the crease of skin lying just under your toes on this foot. Here they come, here they come to tickle you hehehe! Tickle, tickle, tickle. You are such a weak pathetic bitch! You are going to laugh so hard when my nails settle into the space between your toes and the area underneath them. You see them? You see them? Here they come! Here they come to tickle you to DEATH (she scowled and sneered ).
Sara slowly lowered her sharp, pointy nails into the crevasses between my toes on my left foot. As she did so I tried desperately to pull my toes together and protect the ticklish skin in between them, but the toe ties made that impossible. The nail points contacted the thin nylon mesh and as they did she carefully and gently motioned them back and forth, back and forth in a pulsating motion. The thin skin between my toes was stimulated by these nails and my head snapped forward instinctively. At the same time my mouth opened as wide as it could propelling a rush of air forcibly through the balled-up nylon gag in a laughing panicked scream! “NO! MMHAHAHAHAHAHAMAHHAHA”. Meanwhile, after a few seconds I felt her other set of nails dig effortlessly into the crannies of nylon vailed skin at the base of my toes on my right foot. The nail tips once again feasted on the phalangeal region of my toes and did their familiar tickle dance as I laughed and screamed all the air out of my tired lungs again. I was DONE! After only a few moments of this torture I wanted to safe word so badly and indeed uttered it through the gag when I got enough air to surface to form words. Sadly, any word forming cries were sufficiently stifled and all I could do was laugh.
As Sara’s fingernails slowly undulated in between all my toes and under my toes she noticed how desperately I was trying to avoid her tickles. She relished this moment and teased me again.
Sara: Hahaha, look at you trying to curl and wiggle your toes to try and stop my nails from their tickle path. How cute is that? Hmmm, I admire the effort, but you are so helpless and have no choice but to endure my merciless toe tickles! Unbearable isn’t it honey? But this will teach you not to disobey your Mistress. Now, laugh you poor thing. Just laugh your little heart out. Coochie, coochie coo, in between and under your toes. That’s it. Kitchie, kitchie Jenny’s widdle toes (broad evil smile).
Jenny: MHAHAHAHAH…..(silent wheeze and gasp)..MMHAHMAHAHAHAHAH…
After initially screaming a maniacal mirth into my gag the artful and cruel tickling sensations once again robbed me of my breath and I collapsed into silent laugher. With my mouth wide open, my head jerked and bobbed as the rounded piece of saliva-soaked nylon stuffed in my mouth vibrated against the ball gag. I couldn’t form coherent thoughts or words. I could only feel and respond to the waves of ticklishness crashing and roaring through my body. The tickles consumed my consciousness completely and my physical state was reduced to a laughing puddle of goo. It was the most helpless I’ve ever felt being tickled. It both terrified and sexually aroused me! My pussy once again oozed sex juice, signifying my intense sexual state.
The nails kneading the undersides of my toes then started to crawl up the toe stems, then back down them; weaving and scratching the tender flesh of these toes several times before settling back to their initial place at the base of the toes. Apparently wanting to elicit a different reaction from me, she next moved her nails in unison horizontally along the undersides of my toes in a motion analogous to “brushing teeth”. That stimulation caused my head to shake and vibrate trying to avoid the murderous ticklish sensations raging into my nervous system. Yelping what little breath I had left into my gag I again tried to scream “GOLD” my safe word. I couldn’t take Sara’s tickles anymore and I wanted this to end now!
Alas, Sara did not stop. Instead, using the nails tickling between all my toes, she started to attack each individual space between my toes with her index fingernail. A quick scratch and tickle with a nail in between my big and second toe were followed up with a jab and tickle of the crevasse between my third and fourth toe. She would alternate between different patterns of in between the toe tickles that kept me in absolute hysterics with no hope of predicting the path of her evilly skilled nails. After what seemed like a year Sara stopped her nails from wiggling and tickling between my toes, but she kept these nails poised in my toe crevasses and pulled the other set of nails from under my toes. Instead she used her thumbnail and index finger to scratch and tickle the pads of my big toe on my right and left foot in an alternating pattern. Although I was relieved that Sara stopped the unbearable tickles in between the toes and underneath the toes I was shocked by how ticklish my big toes were. Just tickling my big toes in this way was horrifyingly ticklish and I wailed hysterically into my gagged mouth. “mhahamhahahohahahmmmhahahahaha”
Smiling with her evil grin Sara’s thumbnail quickly slid up and down the nylon covered big toe pads while her index fingernail traveled up to the tip of one big toe and began to scrape at the delicate thin skin under the big toenail which was extremely ticklish too! I became hysterical once again. “MHAHAHAMMHANOOOHAHAHAAHAHMMMAHAHA”
Sara: Oooh so your big toes and the skin right here just underneath your big toenails are so very ticklish too huh darling? How lovely. Let’s see if you like the toenail skin of your tootsies tickled. Here we go. Kitchie, coo, kitchie coo right here. Does it tickle honey? Huh?
Sara removed her fingernails from their holding pattern in between my toes and gently gripped my big toe at the toe pad. Then she focused her index fingernail of her free hand and tickled the very thin skin just underneath the big toenail. Satisfied with my intense reaction to that maneuver she lovingly held the second toe around the stem leaving the nylon covered toenail skin available. Then she methodically stimulated the toenail skin of my second toe, followed by the third, fourth, and finally the baby toes. The nails snared the nylon mesh as both rubbed along this delicate skin transmitting painfully ticklish signals through my brain and I vacillated in and out of silent laughter.
Sara: Looks like Auntie Sara found another great tickle spot didn’t she? Yes, she did! Kitchie, kitchie coo. I’ll be you didn’t know just how ticklish your toenail skin is didn’t you baby (she smiling sinisterly)? Well dear, unfortunately, our time is almost up. Now, I need you to do something for me. I am going to take the gag off you. When I do, you better you say “GOLD” your safe word immediately, so I win the challenge. If you don’t say your safe word I will re-gag you and tickle all over your toes, underneath, in between, toe pads and toenails etc. until you pass out. You are beaten and you will give me my earned victory. Do NOT defy me (she said with a stern scowling face). Do you understand?
She was right. I was beaten and I needed a rest and certainly did not want to endure any more of her toe tickling techniques. I was sure that if I did not give in now, Sara would probably stop the timer, make me orgasm again then tickle my toes as mercilessly as she did before, which would be far too much to take. Up until my second forced orgasm I thought I could endure Sara’s tickling advances, but after that second orgasm my nerve endings were completely shot and Sara’s tickling skills were too powerful to ignore and overcome. I knew I simply wouldn’t last another moment and immediately agreed to her request. I lost the challenge. I knew it, and she knew it.
Jennifer: Mmmyesmm! (Nodding her head affirmatively).
Sara: There, there my dear. You are such a good girl! Here, let Auntie Sara take off this nasty gag for you. That’s it.
Sara first unbuckled the ball gag from around my head and gently pulled the saliva-soaked nylon rag from my mouth and kissed my cheek. She then ran her fingernails through my sweaty and tattered hair lovingly in a display of warmth and compassion. Looking at me gleefully, she asked “okay Jenny honey do you have something to say to your mistress?”
As soon as I could gather the strength from my aching mouth I uttered my safe word repeatedly so there was no ambiguity or delay. I was totally broken and did not want to be tickled any more at least not the way I know Sara was going to tickle me if I refused to capitulate.
Jennifer: GOLD, GOLD! (pant, pant). I say GOLD! You (pant, pant). You win Mistress Sara. You win fair and square. Oh God that was awful! Pure torture. I give up (smiling sheepishly). Gold, Gold!
As I was admitting defeat, Sara smiled at me and gave me drink of water. I thanked her and she kissed me again on my cheeks and lips which I returned just as passionately.
Sara: Hmm, I knew I would win baby, but you were a tough one. I had to pull out all my tricks to break you. Typically, I can get people to safe word within a half hour of my tickles once I find their main spots, which I always do (smiles coyly). But you! You lasted a good hour and a half. Then again, I was only allowed to tickle one body part and not even the whole part, so I guess that partially explains the time delay so to speak. Still, you held your own pretty good. You definitely challenged my tickling skills which I appreciate.
Jennifer: Oh well I suppose we both learned much from this experience. I’ll tell you this I am never gonna ware these types of nylons ever again to a tickle session. My feet are way too ticklish in them. Nails on these nylons for me just don’t mix hahaha. And you are one hell of a tickler lady!, Them fingernails of yours are the devil himself! I mean yeah my toes are a real hot zone of ticklishness but those nails you got tortured my poor tootsies like I never felt in my life. Congrats again! So, you want to unhook me now? We done right?
Sara looked at me quizzically and to my horror uttered words I certainly did not want to hear.
Sara: Let you go? Hmm, no I don’t think so honey. Remember? You still owe me another HOUR! But since you were so compliant, I think I’ll reward you with another mind shattering orgasm before I tickle you to tears…again hahaha.
Sara pulled a stiff feather from her bag and began to stroke my sopping wet pussy with it. She carefully moved the soft barbs of the feather across my vaginal lips dipping the tip into my love hole occasionally. The teasing strokes of the feather against my now aching loins was devastatingly pleasurable and I moaned in appreciation and lust. She is going to make me cum again, powerfully which will increase my sensitivity to her tickling administrations; a prospect I am both excited for and very, very nervous. I ask myself how will I endure Sara’s torturous fingernails for another hour? Unfortunately, only time will tell.
To be continued
EnjoyThe Challenge
How many was that? I lost count but I think I just had my fourth forced orgasm. The first one was achieved when my Mistress used her nylon toed foot to stroke and tease my clit. It felt amazing and my climax was very intense! She then used her ever so talented fingers to make me cum another time. But this last orgasm Dominatrix Sara used a stiff feather. I never thought a feather flicking against my love button would bring me to a ground shattering orgasm, but it sure did! I got to hand it to this one, Mistress Sara really knows how to get a girl off ha, ha, ha. But alas just like the other ones, the bitch only gave me a few brief seconds to enjoy the afterglow of these powerfully pleasurable climaxes before engaging her sharp nails to tickle my insufferably ticklish toes. Oh, my fucking GOD she made me wish I was born without toes lol! The way she flicked, jabbed, and teased up and down the stems, sides, tips, the sensitive crease just underneath them, and the webbed flesh in between my post-orgasm gumdrop shaped toes sent me spiraling into unspeakable and agonizingly ticklish sensations! I never laughed so hard and forcefully in my life and I have been tickled dozens of times by some real sadists but; umm never like this!
I suppose it doesn’t help that my feet were encased in a pair of sheer 5 toed nylon stockings. You know, the ones where each toe fits into the nylons like a glove? In these nylons my toes are very accessible to tickling as if they were bare. But nylons as I have learned the hard way, make my feet much more ticklish and this woman took full advantage of that! I can only assume that wearing these nylons was part of the “challenge” of this session which I will describe later.
Let me tell you a little about myself. My name is Jennifer. I am about 5’6”, with brown hair and light eyes. I am athletic but not skinny. I am very, very ticklish everywhere but my underarms and size 7 and ½ feet are my most ticklish spots. I have a love/hate thing about tickling and this Dominatrix here really tested my limits for sure!
In this situation, I was fully clothed with these sheer nude 5 toed nylon stockings except that the hose had been cut open to expose my crotch area. My hands and legs are tied spread eagle in a chair reclined at an angle for my Dominatrix to have easy access to my feet.
Now the soles of my feet are cocooned and mummified by plastic wrap so that only my toes are exposed and pulled up so they are taut making the soft flesh underneath my toes particularly vulnerable.
Okay, so here is the challenge I came up with to endure. First, I searched around to find a Dominatrix that was expert at tickle torture because I wanted to be pushed to my tickle limits. Mistress Sara came highly recommended and when we spoke and got comfortable with each other I offered her a challenge. I told Sara that she could only tickle ONE part of my body and if she could “break me” and make me use my safe word in under 2 hours I would pay her twice the rate of a normal 2-hour tickle session. Basically, she would have to be skilled enough to make me safe word by tickling only ONE body part. If she could do that, she’d get paid double. If, I survived the challenge and did not safe word during the 2-hour time frame she would not get paid at all for the session.
Well, Sara gleefully took up the challenge which I was sure she’d fail. I mean I didn’t think anyone was THAT good at tickling to make me safe word by only tickling one body part even if it was my most ticklish place.
In fact, instead of being intimidated by my challenge Mistress Sara actually upped the stakes and said that if she made me safe word before the deadline that I would not only pay double her rate for the two hour tickle session but I would be forced to endure an additional hour of tickling and pay her time and a half for the additional hour. In effect, I’d be paying her a substantial sum of money if I lost this challenge. Being very confident I said “sure, bring it on girl”.
Spoiler alert, I lost, BIG TIME! Come to find out that Mistress Sara has mad and I mean MAD tickle skills! She kept me on edge and outright drove me completely bonkers making me cry, beg, and laugh like a pathetic little schoolgirl. She even made me verbally tease myself AND beg for her to tickle me! It was pitiful and humiliating. She made me her tickle bitch for sure! Obviously, I definitely underestimated her….umm ingenuity.
Let me go back to the beginning. We agreed that Mistress Sara could take some time to first locate and find the area that she would focus her tickles on for the challenge. This exploration time was not part of the 2 hour challenge because, to be fair, Sara needed to get a good spot because this would be the only place, she would be allowed to tickle me for the challenge, so I gave her the proper time to explore my tickle zones.
At the start I was bound spread eagle but not yet gagged. Now someone really good must have schooled Sara in the art of bondage because after she tied me up I had no play at all. I realized fast that I wasn’t going anywhere. I’ve been bound many times before, but her bondage technique made me a wee bit nervous. I mean, I’m a stronger than average girl but when I pulled on my ties I legit couldn’t budge an inch. If she was trying to hold me captive like in a kidnapping, I doubt I’d be able to escape even if my life depended on it. Truth be told it was kind of scary, but I totally trusted her and was awaiting my tickle torture with bated breath.
Sara then investigated my bound body for all the usual tickle spots and quickly discovered how ticklish my underarms are. From the jump I could tell this bitch knew what she was doing, and she tickled and teased my armpits really well employing a whole range of techniques. Most ticklers often use their nails to alternate between hard and light tickles into the armpit. Both ways send me howling. But these kinds of tickles generate a uniform sensation. Sara employed a technique that offered duel tickle sensations. She used her thumb nails to softly but firmly dig into the tissue in the middle of my armpit and tickled it using tiny circular motions. At the same time, she danced and flicked her other nails along the bottom and sides of my pits. As she did that, oh man! She got me singing notes of laughter I never knew I could reach! Those two different tickle vibrations, firm digs with rotating nails in my pit hollows and light scratching along the sides excited my armpits like nothing else and I crumbled into ear splitting laughter.
Jennifer: Oh ha ha ha ha ha ha ha aahhh ah ha thahahaht tihehehh tickles soohohoh bahahahahd ohohoh ha ha ha ha!
I couldn’t take it and almost safe-worded after only a few minutes. I was in complete hysterics. What made the tickling worse was her verbal taunting (more on that later). I couldn’t stand being reminded how helpless I was or how ticklish she was making my armpits. I must say, a good verbal teaser can make me way more ticklish and Sara is a real pro there to.
I thought whoa, if Sara chooses the armpits, I might be in a whole lot of trouble. But she kept exploring other spots and she made me laugh like a crazy woman on all of them because number one I am dreadfully ticklish everywhere and number two she’s really, really good at exploiting tickle spots. I remembered saying to her after she let me rest before moving to another part of my body “damn girl, you are quite the tickler, aren’t you? Those nails are something else! I think I made the right choice.” I said confidently that “I’m still going to win, but this is going to be fun”. I just didn’t know that the word “fun” would have such a different meaning after this session.
Then she got to my feet. Now before the session began, she insisted that I ware five-toed pantyhose. I never heard of them before really, but she put them on me and actually it was kind of hot. She took off my heals and carefully slipped the nylons on but curiously she then cut a big hole in the crotch area. I thought at the time she did this because she wanted access to my inner thighs in case my feet were not her choice tickle zone, but I was wrong there too ha, ha, ha. Once the stockings were on, she probed my feet with her nails and I just about jumped out of my skin when she tickled them! I don’t know if it was the sharpness of her nails or how fast she could move them or what, but I have never felt so God darn ticklish on my feet before. I swear, a complete idiot that never tickled anyone could turn me into a giggling mess by touching my feet, but this girl was setting my lungs on fire with the tickling she was putting to my arches and soles. I was begging and pleading like I haven’t done in a long time and I’ve been tickled by lots of skilled male and female Domes before. But this girl was in a league all her own.
Furthermore, during this exploration phase, I found out how sadistic Sara is because when I was wailing away in ticklish hysteria and could barely breathe from her nails skittering along my arches instead of easing up satisfied that my arches and soles were extremely ticklish and a candidate spot the bitch went and dug her nails right under my toes! Well that was it! My eyes flew wide open as if I just saw a ghost. I let out a yelp from hell and a blood curling scream before my lungs ran out of air. I just held my jaw open like I was catching flies and wheezed pathetic cries of mercy mired in a wave of exhausting mirth.
“Pleahehehe (gasp) pleaheheh…stoh.(gasp).ohhophahaha”was all I could get out. I tried to beg for mercy, but no sound came out of my mouth. I reflexively curled my toes down hard on her nails trapping them in there under my toes hoping to stop their tickling advances.
Sara: Oh no, no, you don’t young lady. Gimmie back my nails so I get at these little toes! There that’s better. Coochie, coochie coo! Bad little girl trying to stop my tickle nails from getting your little tootsies (evil smile). Naughty, naughty.
Sara easily gained back control of her nails by quickly pulling back on the big toe freeing her tickle weapons. Now able to move, she concentrated the very tips of those sharp nails on grazing and tickling that tender tickle spot along my toe stems just under my toes with a focused tenacity. Helpless now to stop her talented talons from wreaking havoc on my ticklish tootsies I was kept in silent laughter for a good while longer until she let up her pace and allowed me to take in some air.
When I did finally breathe some air into my oxygen deprived lungs, she started right back up again and wiggled those damn nails faster and harder under my toes only this time with my toes held back I couldn’t squeeze them down and I immediately screamed, vibrated my leg up and down as much as my bonds would allow and swooned into a hyperventilating laugh after a few seconds. Sara had a big ol’ smile on her face at my reaction, the heartless bitch. She was toying with me realizing she hit a jackpot tickle zone. I was sure she was going to tickle me to death right then and there! She verbally teased me too.
Sara: Awe I think it’s your little tootsies that are so ticklish girl aren’t they, aren’t they? Oh yes, they are. I think I’ve found your spot and the one I will tickle to win this challenge. Unfortunately for you I am an expert toe tickler. Coochie, coochie, coo little Jennifer. Tickle, tickle, tickle Jenny’s ticklish little toesies .
Mind you I HATE being called Jenny lol! Now I’ve been tickled on my toes before many times and they are very, very, ticklish. Experienced ticklers have had no trouble finding and exploiting my toe area, and a good tickler can really make me suffer by tickling my toes in just the right way. But, every time (before Sara that is) after a while like most tickle spots, my toes would get a little desensitized and the tickler would invariably move on to another zone. So, I figured Sara wouldn’t be able to keep me laughing for the two-hour challenge if she only focused her tickles on my toes. Nope! Wrong again ha, ha, ha.
After tickling all parts of my foot, Sara decided she would direct her attention on my toes and said she could easily keep me in hysterics for the two-hour duration and make me safe word by assaulting my tender planter digits. To be able to devote her tickling on just my toes, she wrapped the length of my soles and ankles tightly with plastic wrap and pulled up on the wrapping to make my sole taut. With my feet bound in this position it made it difficult for me to flex my soles and arches to scrunch my toes in protection, so they were very vulnerable. Because my feet were pulled back so tightly, I could barely wiggle my toes. This was some serious foot bondage.
Sara: Okay Jennifer dear now let’s begin your challenge. Just be clear on the terms. I will focus my tickles only on your toes and tickle them until you utter the safe word “Gold”. If I do that, I will win double my normal fee and get to tickle you for an additional hour at time and a half my fee. Is this correct?
Jennifer: Yes, Mistress Sara that is correct. You can use any tools you wish but you can only tickle my toes during the 2 hours”.
Sara: Oh honey, the only tools I’m going to need are my fingernails. I’m afraid you will safe word after about an hour. You’re pretty tough judging by my exploration time and have good stamina but you are not that tough, especially after I prime you in my special way ha ha ha.
Jennifer: Prime me? Not sure what that means but it can’t involve tickling me anywhere else but the toes.
Sara: Oh, I know that darling. My primer won’t tickle I promise. I will set the timer on my phone when I begin tickling you. But I’m not going to tickle you just yet (evil smile).
Not exactly sure what she meant I saw Sara take her shoes off. I assumed she wanted to get more comfortable before she engaged in tickling me. But then she raised her nylon foot up towards my spread and exposed crotch. Wow what a pretty foot she has! They look about my size 7 but maybe a bit smaller and I think her toenails were painted red. It was hard to tell because she had on these sexy black nylon stockings. But she has really deep arches and elegant looking toes.
Oh my, her toes are rubbing up my crotch and up against my vagina. It feels so good. Now Sara is kissing my toes gently and using her tongue to slide up the stems and glance along the tips. It tickles only a little and I smile softly in response.
Jennifer: Hmm, are you planning on lickling my toes to torture me? I must say I do enjoy it. But I don’t think you’ll win this way (giggle giggle) hmm ha ha ha even though it does tickle a bit.
Sara just smiled at me as she continued her licks and soft nibbles on my toes. But now I started to feel her own toes enter into my vaginal area and petting the labia flaps. The smoothness of her nylons combined with the softness of her tongue on my toes is getting me real horny.
I started to get a little wet and sensing my wetness Sara began to stroke my clit with her toes very gently and softly. I reflexively moaned and sighed. Almost as if on cue, Sara took the big toe of her other nylon clad foot and penetrated me with it; back and forth, back and forth like she’s fucking me with her big toe. It felt incredible! She then used her toes to more aggressively stimulate my clit as my vaginal area became increasingly moist. And oh, watching the tongue of her pretty face licking my toes so passionately and lovingly was one of the hottest things I’ve ever seen. But when she started to talk to me that is when all hell broke loose!
Sara: Hmm Jennifer darling your toes taste so good. They are so very pretty. Not a dry piece of skin anywhere on them. I think you like Sara’s tongue licking up and down you widdle toes huh? I think so. You feel so wet down here baby. You like my toes up your snatch honey? Do you want more huh, sweetie? Do you want Sara’s tootsies to make you cum? Is that it?
I immediately responded: “Oh hell yes! Keep fucking me with your toes Sara (moans and sighs). It feels so good!”
I got to tell ya, my pussy was dripping like a busted water pipe as her smooth nyloned big toe was fucking me in and out fast and hard and her other nylon toes were stimulating my clit something fierce. Incredibly her toes were as agile if not more so than fingers. Now I’ve had my share of some excellent lovers, both men and women, who brought me to powerful orgasms, but this woman was about to make me squirt a ton of cum by using her toes! I didn’t think that was possible. But there I was; moaning and grinding my hips like a dog in heat helping her toes fuck me. I was completely lost in a sea of pleasure. Feeling smooth nylon toes on my clit and in my pussy coupled with Sara’s warm tongue and mouth sucking and licking my feet and toes was overwhelming. With the 5 toed pantyhose she was able to easily snake her talented tongue in between my toes which again kind of tickled but felt so good and amplified my sexual pleasure. I think I was actually turned on by hearing myself giggle softly in response to her teeth and tongue slurping around my toes as my clit was on fire and becoming engorged.
Sara: Hmm your toes taste so good (slurp, slurp, lick lick). Are you gonna hmm (lick, lick, nibble, slurp) cum for me Jenn baby huh (lick, lick, slurp)? Do my nylon (long lick up the toes) umm toes against your (lick, slurp, lick) clit feel good my dear hmm (nibble, lick, slurp)?
“Oh my GOD YES!” I cried in earnest. My eyes rolled in my head and I was arching my back and thrusting my hips wildly towards Sara’s toes digging and grinding relentlessly on my clit. Just then, Sara reached up and undid my blouse and bra to expose my tits. Then she pulled one of her nyloned foot from my pussy and started to rub against one of my breasts. I didn’t even notice that foot coming towards my naked mounds but as they landed on them, she spread her nylon big toe and wrapped my nipple in between her big and second toe and tugged on it gently. It felt amazing! The wetness of her nylon foot up against the nipple of my breast was so stimulating and caused my already rock-hard nipples to become even more erect and prominent. I let out a deep sigh of passion and pleasure as her moistened toes then wafted back and forth across breast. I felt as though three different lovers were attending to me.
As Sara was worshiping my feet and using her own nylon toes and feet to pounce on my clit and tits, she verbally teased me.
Sara: Now (slurp, lick, slurp) beg me to tickle your toes baby. If you (lick, slurp, slurp) beg me to tickle your toes without mercy (lick, lick, slurp, slurp) I will make you orgasm honey. Beg me with all your hmm (slurp, slurp, lick, lick) life to tickle your toes and I’ll let you orgasm. But you gotta hmm (slurp, slurp, long lick, lick) beg for the toe tickles first!
Well my clit was on fire and I never wanted to cum so bad in my life, so I did the unthinkable and begged Sara to let me orgasm just as she asked. It was quite embarrassing, but this crazy talented bitch was not giving me any choice at all! I was in a deep sexual trance with no way to escape, not that I wanted to. Bottom line is that Sara had me right where she wanted me, and she knew it!
And so needless to say, I begged ! I begged with all my heart! “Oh GOD okay, okay! Sara please, oh, oh tickle my hmm (biting lip) tickle my toes. I…I, oh shit right there…please I beg you, hmm (huge passionate smile) tickle torture my…OH GOD YES!”
Sara: Your what? Tickle your (lick, lick, slurp,) what honey? What do you want Sara to tickle? (furiously stimulating the clit with her nylon toes).
“OH, OH, JESUS! TICKLE…OH GOD..TICKLE MY…HMMM YES! MY TOES! TICKLE MY TOES! Tickle my ohh ohh GOD… TICKLE MY TOES …PLEASE!!”
Sara: Tickle your toes huh? Do you (lick, lick, slurp, nibble) want me to tickle your toes mercilessly? Is that what (slurp in between the toes) you want me to hmm (long lick along the toes) do?
Sara’s foot and toes were loving on my clit so artfully and relentlessly I screamed and begged for my poor toes to be tickled just as she instructed. I had no resistance left. My libido was too jacked up. I needed to release the enormous sexual energy building inside me, and I whined and begged again like she asked. It was so humiliating!
“YES! YES! TICKLE MY TOES MERCILESSLY! MERCILESSLY! OHHH GOD I WANT TO CUM”! I couldn’t believe my own ears! I was literally begging this woman to tickle my feet and toes without remorse or quarter. I simply could not control my will or thoughts. All I wanted to do was orgasm all over this woman’s foot stimulating my clit. It was so intense!
Sara: Good girl Jenny! Mistress Sara will make you cum now.
All I remember after that is the feeling of what appeared to be the nail of her nyloned big toe graze the tip of my clit several times. After which my body exploded into one of the most intense orgasms I’ve ever had. My hips thrust forward with such force I felt the restraints dig into my thighs. I let out a scream of pleasure so animalistic the volume rattled my teeth. It was definitely a very prolonged orgasm! I experienced several waves of pleasure coursing through my body as I convulsed for several seconds. It was incredible! Then as I was recovering, I felt Mistress Sara stroke my lightly sweaty hair from my face with her nails. She kissed me passionately on the lips which I returned in kind, thanking her for that enormous feeling of pleasure.
Sara: Hmm, did you like that Jennifer? I think you did. My nylon foot is absolutely drenched ha ha ha. I felt a little tickle to my own nylon toes from the force of your pussy juice squirting all over them ha ha ha. Quite remarkable indeed.
Wheezing and still out of breath, I said “oh my God that was incredible Sara! I don’t think I ever came so hard in my life ha ha ha. Whew. That was so intense. I don’t often squirt like that but based on the orgasm you gave me, I’m certainly not surprised I did ha ha ha”.
Sara: Good! Now that my toes have given you such pleasure my nails here are going to reciprocate and pleasure your toes (wiggles her sharp nails in front of Jennifer’s face). After all dear, didn’t you beg me to tickle your toes just a moment ago? And to tickle them without mercy?
Jennifer: Oh, holy shit NO! Don’t! Don’t do that. Please don’t tickle my toes. I..I..didn’t mean it. Oh God please, I’m too sensitive right now (I pathetically begged knowing full well what her plan was all along).
Sara: No? Oh, but dear you pleaded with me so convincingly to tickle these toes of yours that I must do so right now (evil smile). So here you go. Coochie, coochie, coo Jennifer’s little toes. Tickle her toes, my sharp little nails. Tickle them good just like Jenny asked you to do. Kitchie, coo, kitchie coo.
Sara set her timer now because she is about to unleash a fury of toe tickles that will have me breathless in minutes.
First, she used all her nails to gently flick and tickle the tender stems of my medium sized toes on both feet. She concentrated the tips of her sharp nails near the top of the fleshy part of the toe stems. The nails moved quickly but gently at first. However, because my nerves were so heightened and sensitized by my incredibly powerful orgasm just moments ago her toe tickles sent ticklish waves through my toes the likes I have never experienced, and I let out a torrent of feverous laughter!
“OHNOO….hahahahahahahahahaha…(wheeze,gasp)…thahahahahat..hahahahahahahahtickles soohohohohoho bahahahahad! Ahahahahahahahahhahah!”
I slammed my head back down on the soft headrest of the chair and laughed dutifully and powerlessly. Sara then took one set of nails and tickled across the middle of my toe stems in a horizontal motion while the other set of nails continued to parade up and down the length of my toes. Long slow tickle strokes up followed by fast skittering flicks as they reached the tops of the toes and back down again. Changing patterns constantly. The fact that she could move each of her fingernails to create such different tickle patterns was amazing! I thought I was being tickled by several sets of nails not just two and I was beginning to regret my “bet” with this very talented Mistress.
“Hahahahahahahaa..stoohohohop..hahahahaha..ohohohoh..thehehehehe toehohohoes..nothahahahaha.thehehehere.hehehehehahahahahahahahahaha.”
I was beside myself begging like a wimpy little bitch. I would normally be able to take a little bit of toe tickling especially this kind of gentle teasing of the toes, even though they are one of my worst spots. But this was different. My oversensitive nerve endings from the orgasm gave the fuel to this tickle fire unleased upon my toe flesh and the smoothness of the nylons were just putting gasoline on that fire. Sara’s fingernails moved with such speed and grace that the nylon fibers were scratching my sensitive toe flesh in unison with the tips of the nails. It was like a tickle echo chamber; a fingernail scratch, followed immediately by a nylon itch up and down and across my ticklish toes. It was maddening! And the verbal teasing was just sending me over the edge.
Sara: Hmm kitchie, kitchie, coo little toes. Oh, I know you love Auntie Sara’s nails ticking and tickling your ticklish widdle nylon tootsies huh Jenny baby? Listen to you laugh as my tickle nails go up and down your toes, and now across the toes. Hmm, yes, tickle, tickle, tickle the toes. The nylons make it tickle more, huh? Hmm, I’m so glad I made you wear these special nylons. They help my fingernails that are so good at giving Jenny the tickles she wants on her toes! Coochie, coo, coochie coo little toes. Tickle, tickle, tickle (big evil smile).
I was screaming now in a tickle panic the likes of which I have never done before. The combination of her nails tickling against the smooth nylon fabric was simply unbearable. I tried to wiggle my toes a little or curl them down but the angle of my arched foot by the plastic wrap made that impossible to be of any relief. My toes were prisoners to her nails and stood there helpless to her tickle administrations which were as relentless as they were precise. I was in tickle hell!
ohhhahahaha…(gasp) nomohohohrehahahah..(gasp)..I screamed. I was in tickle agony and would have done anything for her to stop those nails tickling my toes. But my fate was sealed. Sara was going to tickle my toes until I safe worded. I know she will stop at nothing to win this challenge and I feared I was already losing the battle. The tickling sensations were beginning to overwhelm me, but I tried to just embrace my sub-side and take it. Well that strategy didn’t last too long as I now felt Sara’s evil nails start to dig and wiggle into the tender space right under my toes!
Almost as if she felt my desperation, her sharp nails plunged into the delicate area at the top of the ball of my foot and nestled into the soft fleshed canal right at the base of my toes. The fingertips of the nails rested along the ridge of the toe line providing the fulcrum for the sharp edge of Sara’s nails to wiggle and scratch the thin nyloned skin residing in the region connecting the toes to the ball of my foot. Her nails gyrating in this area elicited ungodly ticklish sensations. It’s as if her nails were perfectly designed (and skilled) to fit snuggly into this spot for the purpose of stimulating and tickling this murderously ticklish area!
Not surprisingly, my eyes widened, my mouth formed a perfect “O”, and I let out a screech of laughter before my head slumped down towards my chest and I slipped into silent laughter. I tried to speak, beg, plead but all that came out was
”ohhahh..(silent)..nohohoh..(silent)..NO! (wheeze, gasp) NOT..NOT THERE! hahahaha (silent gasp)….OH PLEASE (silent wheezing)!!
Sara smiled triumphantly and with a snide snicker in her voice said “Oh, really? Not here? Are my nails tickling you right here under your tender little toes Jenny pooh? Hmm, yes, I think they are! I know someone who has some very ticklish toes! I think you love to be tickled right here just under your toes! But this is just one foot. Let’s see if you like it more if I tickle BOTH feet right here where you love it so much. Won’t that be nice? I bet it will tickle very much (evil grin). Kitchie, kitchie, coo. Tickle under Jenny’s toes on both her feetsies little sharp tickle nails. Tickle under Jenny’s toes right here. Come on now coochie, coochie, coo her right here under her toes. Afterall, she begged us to tickle her toes. Didn’t she? Yes, she did! She just loves her toes tickled, so coochie, coochie coo under the toes!
The evil bitch knew I was tail-spinning into silent laughter and wanted to send me over the edge by doing the exact same thing to my other foot. Smiling cruelly, she clawed her fiendishly effective tickle nails under the toes of both feet. I swear I am never going to wear nylons again during a tickle session. A really good tickler would destroy me in these hose same as this woman is now. With the double underneath the toes tickling I was losing all control, coming in and out of silent laughter for what seemed like several minutes. Her sharp nails glided and dug in and out periodically under my toes, while also occasionally nipping at the toe stems to keep me off balance only to return to pulse and jab her talons softly but firmly against the absurdly ticklish spot underneath my toes. She was driving me into a tickle induced state of lunacy. These were not fun tickles. No, these tickles were causing my nerve endings to implode, and I could barely stand it any longer!
I didn’t know how much time had passed but I was confident I was almost at the end of the two hours. I thought if I could just hold on a little bit longer, I would make it and win the challenge. Suddenly and curiously Sara eased up her tickling and pulled her nails from underneath my toes and simply flicked her fingertips along the tops of my toes, almost massaging them. I welcomed the reprieve and was hopeful I had endured the worst but alas my hopes were completely dashed when I heard Sara tease me again.
Sara: Oh, Jenny darling you are doing so well! You haven’t yelled your safe word yet and it’s been a full 30 minutes! You have wonderful stamina. Because you’ve done such a good job, I’m going to stop tickling you, shut off the timer here and make you cum again. Wouldn’t you like that?
I thought to myself OMG, you’ve gotta be kidding me! I’ve only suffered for a half hour of her tickling? When I heard that my heart sank, and I realized I am so screwed and thought about giving up right then and there. I almost used my safe word a few moments ago when this bitch was vibrating her nails under my toes and I thought for sure she knew I was about to give up, when she stopped her tickling advances. I didn’t understand it at the time, but this was Sara’s plan all along. She wanted to break my will so badly and completely that the way to do that was for her to have ultimate control over my reactions, body, and mind.
Sara: Yes dear. Here you go. Let Auntie Sara make you orgasm again sweetheart. There now, that’s so much better isn’t it? How do my fingernails feel as they dance on your pussy? You like them on here huh baby? Hmm better my nails fingerbang your pussy than scratching and tickling your poor toes hmm honey (evil smile)?
As soon as her fingers entered my pussy and landed on my clit, I let out a moan and a sigh as I felt such intense pleasure. She went right for the golden love button as my pussy was still sopping wet from my last orgasm and the subsequent tickling that always arouses me. But what a contrast from the cruel tickling on my toes just moments ago. I arched my back and moved my crotch towards her loving hands as they flicked along the edge of my pussy lips and stimulated my clit. This woman must have finger fucked hundreds of women because boy oh boy did she know her way around a vagina hahaha. My pussy was on fire in seconds and longing for her to make me cum again. I bit my lip and moaned louder encouraging her towards making me orgasm.
Sara: Hmm, feels good baby? You know, I could have made you use your safe word back there if I continued to tickle underneath your toes. You know that right? (stimulating Jennifer’s clit harder).
Jennifer: Hmm, yes..oh yes. I know that. Oh God (sighing and moaning), please..right there!
Sara: I want you to admit that I could have made you give up by tickling underneath your toes. Say it and I will make you cum so fucking hard and long! Coochie coo Jenny’s clit, coochie coo.
Jennifer: Oh Jesus! Okay, okay. You..oh God.. you could have..hmm (biting lip)..made me give up…OH GOD…ahh yes..give up by tickling…ahh ohhh please fuck me more…by tickling underneath my..ohh yeah, ohh yeah..my toes! OH GOD!
Sara: Good girl! Such an obedient girl. Now I want you to beg me and ask Mistress Sara, to please tickle you right in between each of your toes with her nails and make you safe word. Say that and I will let you orgasm.
I gotta hand it to this woman, she is making me beg to be tickled with such great intensity that I safe word and lose my challenge. I mean what an absolute mind fuck! She wants me to beg for my own demise. I know once I orgasm and she tickles me in between my toes I will have a very difficult time resisting and I don’t think I can hold out for another hour and a half with her tickling my toes, especially not after I orgasm like I’m going to be forced to do again. My nerve endings will be shot, and I’ll have virtually no resistance left against her skillful and agile nails. I just know my toes will be way too ticklish and I’ll crack for sure. The question is how long will she tease me and prolong the inevitable? How long will she make me suffer the tickle torture which I know is coming? I feel deflated yet very excited about the prospect of being so mercilessly tickle tortured. I mean this is part of the reason why I came up with this challenge. I wanted someone to push my limits and really torture me! Well, looks like it’s happening now.
Sara: Say it baby! Beg me to tickle you in between your cute ticklish little nylon toes. Beg me and I’ll continue to fuck your pussy and clit to make you cum, and cum hard!
Sara stopped stimulating me to let me know she is serious and wants me to beg her as she asked. I felt so powerless and humiliated but having no choice I complied.
Jennifer: Oh no don’t stop please, Sara (pant, pant). Make me cum. Please make me cum (pant, pant).
Sara just grinned disappointingly at me and said “well then if you want to orgasm then beg me! Beg me you tickle slut! Beg your Mistress to tickle right in between your toes!” She commanded.
Jennifer: Okay. Okay. Mistress Sara, please I beg you, please, please tickle in between my toes. Please I want you to tickle in between my toes so badly. Please!
Sara: Hmm, how long do you want me to tickle you in between your little toes Jenny darling?
(Oh God do I HATE being called Jenny but what can I do?) “Hmm, oh..umm..tickle me there until I.. until I..”
Sara: Until you what? (stimulating Jennifer’s clit again and finger fucking her harder). Tell me or I’ll stop fingering you (singing chiding voice).
Jennifer: Until I..say my..until I say my safe word. Tickle my toes until I safe word..PLEASE (pouting face), OH GOD! YES! DON’T STOP! RIGHT THERE! I’m gonna cum so (panting and moaning) so, OH GOD! SO MUCH! AHHHH!
As I felt her artful fingers stimulate my engorged clit my mind took off to a destination of pleasure I didn’t know existed. Sara grinned widely, nodded her head and said “As you wish darling”. Then her fingers caressed my clit again and I was catapulted into a fantastically long and hard orgasm. I squirted pussy juice again as wave after wave of pleasure coursed through my body. As the orgasm raced through my body, her fingers no longer were needed on my clit and she simply watched my body writhe in orgasmic convulsions. The aftershock of orgasmic energy made me dizzy and I gasped several times to try and slow my breath and come back to Earth.
Jennifer: Holy shit! What the fuck was that? How, (panting and gasping) whew, how did you make me cum so fast and hard? Oh my God that was soooo intense. My compliments to the chef ha ha ha.
Sara: Oh, why thank you love. It’s actually quite easy to make a girl orgasm like that after she’s been tickled to the brink of madness as you just were ha ha ha. All the nerve endings in the erogenous zones are on high alert and all it takes is the right stimulation to unleash their fury. Glad you enjoyed that because now unfortunately, I am going to have to tickle in between your nylon toes with such a ferocity that you will safe word within minutes. But I don’t want that to happen, so I am going to have to gag you now. Oh, I’m perfectly aware if you say the safe word I automatically win the challenge, but I know I am going to win anyway I just want to make you suffer more and I don’t want to be gentle with your toes. I want to tickle them savagely and I can’t have you ruin my fun by safe wording to soon. So, here is what I am going to do. I’m going to take off one of my nylon stockings here (Sara unclips the stocking off her right foot from the garter belt) and use it to first wipe your pussy to get it nice and wet with your own love juice. There we go (Sara dabs the stocking fabric onto Jennifer’s soaking wet mound making the nylon very moist and soppy).
Now I’m going to gag you with this nylon stocking soaked in your own cum juice hahaha. Hmm lovely!
Jennifer: At that moment before I understood what was happening Sara stuffed that balled up nylon stocking wet with my own orgasm tang in my mouth and secured it with a ball gag. “NO!” Please don’t gag…“me..muphhphph”. As I tried to beg not to be gagged, the bitch stuffed my mouth too quickly to complain. I tasted my own cum as I inadvertently bit down on the nylon trying to free if from my mouth. I felt so violated and humiliated. And I have to admit I was a bit nervous at that time. There was a part of me that did not want Sara to tickle in between my toes because I know how bad it’s going to tickle me especially after the ground shaking orgasm I just had and now I wasn’t going be allowed to beg much less say my safe word.
Sara tapped her chin with her pointer finger as she started the timer again and mused: “Now, let’s see where should I begin? I think I’ll tickle in between your second and third toes here on your left foot. Gimmie these toes here. Tickle, tickle, tickle, in between Jenny’s tootsies. Does my fingernail tickle you here?”
Gently pulling my second toe to the side exposing the space in between it and the ring toe she carefully scratched a nail along the nylon meshed webbed space between these two toes. I motioned “NO” with my head and eyes as the gag prevented my verbal protest. And as soon as the nail made contact with the nylon covered flesh and wiggled there my eyes flew open my head lurched forward and I screeched into my gag with ferocious hilarity. It was brutal! “Mphhphahahahahahaha”. I felt that I just got electrocuted with a lightning bolt of tickles as I tried desperately to bring my toes together and stop her nail from its evil tickle path, but Sara held these toes apart easily. I had no leverage at all.
She laughed to herself knowing she hit a good spot and moved to tickle the space in between the ring and forth toe. Another maniacal scream of laughter tried to escape my gag as I felt Sara’s slender sharp fingernail tantalize and tease this sensitive area. It always amazed me how one finger tickling such a small space could inspire such unendurable tickling sensations causing me to explode in involuntary laughter so easily.
Sara: Oh, good lord Jenny dear how incredibly ticklish you are between these toes! Hahaha, such a tickly widdle girl you are hahaha. Kitchie, kitchie, coo in between these little tootsies. What about the space in between your fourth toe, and baby toe? Do you think this place will be ticklish? Huh, my slutty little tickle bitch? Answer me you tickle whore. Nod your head and tell me if in between your pinky toe is ticklish (cruel evil smile).
The evil Mistress paused for a second to separate my pinky toe from the fourth toe and wiggled her sharp index fingernail in a mocking fashion just above the gapped area informing me she is about to tickle the crevasse between these toes. Seeing her fingernail ominously wagging above my incredibly sensitive toes, I nodded my head affirmatively to indicate “Yes” your fingernail will send massive tickle derived sensations if it scratches in between my fourth, and baby toe. It will indeed tickle like crazy!
Sara: Hmm, I thought so! Usually baby toes are quite ticklish. Kitchie coo, kitchie coo pinky toe! Enjoy my sharp fingernail coming to tickle you (she said in baby talk voice). Coochie, coochie, coo!
Sara did indeed position the edge of her tapered index fingernail into the crease between these two toes and glided the sharp nail across the tender webbing laying beneath the surface of the sheer nylon fabric. I gasped and then hollered a fit of laughing torrents cruelly silenced by the tight gag enveloping my mouth. I quickly started to laugh uncontrollably but the lack of sound escaping the gag did not hide the incredible tickle panic my body was experiencing. Sara’s fingernail scratched and tickled the webbing between these two toes and then proceeded to pull back on the littlest toe to tease and play with the insanely ticklish crease just under the bend of the pinky toe which I never knew was so God damn ticklish! As she tickled and gnawed at this very tender spot, I let out another involuntary scream and whipped my head side to side trying to escape the “out of this world” tickle sensations as the nail invaded the ticklish recesses of the pad and wrinkled fold of skin underneath my poor baby toe. It was incredible how bad it tickled!
“Mhahahaha (silent gasp) hahahahahaha (wheeze, gasp) uhhauahahahaha”
Sara’s powers of observation from tickling dozens of women are so well-honed because realizing immediately that she hit a particularly good tickle spot she exacerbated my state of tickle agony she teased me.
Sara: (tilting her head to the side like George Clooney does in so many of his movies said in a singing like chiding voice), oh my goodness, someone’s widdle pinky toe is so very ticklish. I think Jenny wants Sara’s tickle nails to really tickle this pinky toe, huh? Nod your head again like you did before and encourage ALL my tickle nails to tickle in between and all around your baby toe… baby no pun intended hahaha (she said with an evil chuckle and smile).
I instinctively shook my head “NO” and wailed unintelligibly for her NOT to tickle my baby toe anymore. My head was spinning, and my lungs burned from laughing so hard and forcefully. However, Sara was not pleased by my “answer”, became very angry and decided to punish me severely!
Sara: NO! You are shaking your head “no” to me? Are you fucking kidding!? You are defying your Mistress? Oh, I see. You must really want to be tickle tortured huh girl? Okay you asked for it! Do you remember how bad my nails tickled underneath your toes? Well I’m going to use these sets of nails to tickle underneath that delicate area right under your toes (waves her red nail polished fingernails into the air for me to see) and these sets of nails to tickle and tease in between all your toes. I will unleash holy tickle hell on your toes now! You are a disobedient bitch! You will safe word in mere minutes, but I won’t hear it through that gag. You will most likely pass out from silent laughter as you run out of breath. And when you wake up, I’ll do the exact same thing again. I’ll teach you to disobey me. First, let me tie your baby toe and big toes so I can spread them out nice and wide.
I was shocked by Sara’s display of cruelty. It was such a small, unintentional, and innocent bit of defiance caused by tickle induced delirium, but it didn’t matter. She wants to torture and humiliate me pure and simple. All she needed was a little pretext to carry out her maniacal plan of utter conquest. She knows she has totally broken me. Both her and I know I have lost the challenge even though I have not technically used my safe word yet. It doesn’t matter because Sara knows I will speak it the moment she removes this gag. She is just focused on humiliating me and completing my torture.
With that, Sara looped a thin piece of string around the baby and big toes and tied them to slots on the side of the chair so that my toes were spread and completely helpless to pull together or scrunch up. My toes are doomed to be tickled. Now I am not ashamed to admit that for the first time in my life I was really scared! I mean legit scared!
My toes now tied and utterly helpless, Sara begins the ruthless torture. Framing her left hand as a “claw” she hovered right over my flayed-out toes pointing the tips of her nails to pierce directly in the creases between them. Smiling cruelly, she teased me.
Sara: Here come my nails to tickle righhht in between all of your wonderfully spread nylon toes on this foot (left one). Your toes wrapped in these special glove-like nylons make getting in between them so very easy and we know how much more ticklish your toes are in these nylons.
She was so right. I think these nylons made her tickling machinations on my toes so much more ticklish because of both the nylon material and the easy access to the areas in between the toes. Continuing with her verbal teasing, Sara said
Sara: And these nails over here (wiggled in the air approaching my right foot) are going to torture the crease of skin lying just under your toes on this foot. Here they come, here they come to tickle you hehehe! Tickle, tickle, tickle. You are such a weak pathetic bitch! You are going to laugh so hard when my nails settle into the space between your toes and the area underneath them. You see them? You see them? Here they come! Here they come to tickle you to DEATH (she scowled and sneered ).
Sara slowly lowered her sharp, pointy nails into the crevasses between my toes on my left foot. As she did so I tried desperately to pull my toes together and protect the ticklish skin in between them, but the toe ties made that impossible. The nail points contacted the thin nylon mesh and as they did she carefully and gently motioned them back and forth, back and forth in a pulsating motion. The thin skin between my toes was stimulated by these nails and my head snapped forward instinctively. At the same time my mouth opened as wide as it could propelling a rush of air forcibly through the balled-up nylon gag in a laughing panicked scream! “NO! MMHAHAHAHAHAHAMAHHAHA”. Meanwhile, after a few seconds I felt her other set of nails dig effortlessly into the crannies of nylon vailed skin at the base of my toes on my right foot. The nail tips once again feasted on the phalangeal region of my toes and did their familiar tickle dance as I laughed and screamed all the air out of my tired lungs again. I was DONE! After only a few moments of this torture I wanted to safe word so badly and indeed uttered it through the gag when I got enough air to surface to form words. Sadly, any word forming cries were sufficiently stifled and all I could do was laugh.
As Sara’s fingernails slowly undulated in between all my toes and under my toes she noticed how desperately I was trying to avoid her tickles. She relished this moment and teased me again.
Sara: Hahaha, look at you trying to curl and wiggle your toes to try and stop my nails from their tickle path. How cute is that? Hmmm, I admire the effort, but you are so helpless and have no choice but to endure my merciless toe tickles! Unbearable isn’t it honey? But this will teach you not to disobey your Mistress. Now, laugh you poor thing. Just laugh your little heart out. Coochie, coochie coo, in between and under your toes. That’s it. Kitchie, kitchie Jenny’s widdle toes (broad evil smile).
Jenny: MHAHAHAHAH…..(silent wheeze and gasp)..MMHAHMAHAHAHAHAH…
After initially screaming a maniacal mirth into my gag the artful and cruel tickling sensations once again robbed me of my breath and I collapsed into silent laugher. With my mouth wide open, my head jerked and bobbed as the rounded piece of saliva-soaked nylon stuffed in my mouth vibrated against the ball gag. I couldn’t form coherent thoughts or words. I could only feel and respond to the waves of ticklishness crashing and roaring through my body. The tickles consumed my consciousness completely and my physical state was reduced to a laughing puddle of goo. It was the most helpless I’ve ever felt being tickled. It both terrified and sexually aroused me! My pussy once again oozed sex juice, signifying my intense sexual state.
The nails kneading the undersides of my toes then started to crawl up the toe stems, then back down them; weaving and scratching the tender flesh of these toes several times before settling back to their initial place at the base of the toes. Apparently wanting to elicit a different reaction from me, she next moved her nails in unison horizontally along the undersides of my toes in a motion analogous to “brushing teeth”. That stimulation caused my head to shake and vibrate trying to avoid the murderous ticklish sensations raging into my nervous system. Yelping what little breath I had left into my gag I again tried to scream “GOLD” my safe word. I couldn’t take Sara’s tickles anymore and I wanted this to end now!
Alas, Sara did not stop. Instead, using the nails tickling between all my toes, she started to attack each individual space between my toes with her index fingernail. A quick scratch and tickle with a nail in between my big and second toe were followed up with a jab and tickle of the crevasse between my third and fourth toe. She would alternate between different patterns of in between the toe tickles that kept me in absolute hysterics with no hope of predicting the path of her evilly skilled nails. After what seemed like a year Sara stopped her nails from wiggling and tickling between my toes, but she kept these nails poised in my toe crevasses and pulled the other set of nails from under my toes. Instead she used her thumbnail and index finger to scratch and tickle the pads of my big toe on my right and left foot in an alternating pattern. Although I was relieved that Sara stopped the unbearable tickles in between the toes and underneath the toes I was shocked by how ticklish my big toes were. Just tickling my big toes in this way was horrifyingly ticklish and I wailed hysterically into my gagged mouth. “mhahamhahahohahahmmmhahahahaha”
Smiling with her evil grin Sara’s thumbnail quickly slid up and down the nylon covered big toe pads while her index fingernail traveled up to the tip of one big toe and began to scrape at the delicate thin skin under the big toenail which was extremely ticklish too! I became hysterical once again. “MHAHAHAMMHANOOOHAHAHAAHAHMMMAHAHA”
Sara: Oooh so your big toes and the skin right here just underneath your big toenails are so very ticklish too huh darling? How lovely. Let’s see if you like the toenail skin of your tootsies tickled. Here we go. Kitchie, coo, kitchie coo right here. Does it tickle honey? Huh?
Sara removed her fingernails from their holding pattern in between my toes and gently gripped my big toe at the toe pad. Then she focused her index fingernail of her free hand and tickled the very thin skin just underneath the big toenail. Satisfied with my intense reaction to that maneuver she lovingly held the second toe around the stem leaving the nylon covered toenail skin available. Then she methodically stimulated the toenail skin of my second toe, followed by the third, fourth, and finally the baby toes. The nails snared the nylon mesh as both rubbed along this delicate skin transmitting painfully ticklish signals through my brain and I vacillated in and out of silent laughter.
Sara: Looks like Auntie Sara found another great tickle spot didn’t she? Yes, she did! Kitchie, kitchie coo. I’ll be you didn’t know just how ticklish your toenail skin is didn’t you baby (she smiling sinisterly)? Well dear, unfortunately, our time is almost up. Now, I need you to do something for me. I am going to take the gag off you. When I do, you better you say “GOLD” your safe word immediately, so I win the challenge. If you don’t say your safe word I will re-gag you and tickle all over your toes, underneath, in between, toe pads and toenails etc. until you pass out. You are beaten and you will give me my earned victory. Do NOT defy me (she said with a stern scowling face). Do you understand?
She was right. I was beaten and I needed a rest and certainly did not want to endure any more of her toe tickling techniques. I was sure that if I did not give in now, Sara would probably stop the timer, make me orgasm again then tickle my toes as mercilessly as she did before, which would be far too much to take. Up until my second forced orgasm I thought I could endure Sara’s tickling advances, but after that second orgasm my nerve endings were completely shot and Sara’s tickling skills were too powerful to ignore and overcome. I knew I simply wouldn’t last another moment and immediately agreed to her request. I lost the challenge. I knew it, and she knew it.
Jennifer: Mmmyesmm! (Nodding her head affirmatively).
Sara: There, there my dear. You are such a good girl! Here, let Auntie Sara take off this nasty gag for you. That’s it.
Sara first unbuckled the ball gag from around my head and gently pulled the saliva-soaked nylon rag from my mouth and kissed my cheek. She then ran her fingernails through my sweaty and tattered hair lovingly in a display of warmth and compassion. Looking at me gleefully, she asked “okay Jenny honey do you have something to say to your mistress?”
As soon as I could gather the strength from my aching mouth I uttered my safe word repeatedly so there was no ambiguity or delay. I was totally broken and did not want to be tickled any more at least not the way I know Sara was going to tickle me if I refused to capitulate.
Jennifer: GOLD, GOLD! (pant, pant). I say GOLD! You (pant, pant). You win Mistress Sara. You win fair and square. Oh God that was awful! Pure torture. I give up (smiling sheepishly). Gold, Gold!
As I was admitting defeat, Sara smiled at me and gave me drink of water. I thanked her and she kissed me again on my cheeks and lips which I returned just as passionately.
Sara: Hmm, I knew I would win baby, but you were a tough one. I had to pull out all my tricks to break you. Typically, I can get people to safe word within a half hour of my tickles once I find their main spots, which I always do (smiles coyly). But you! You lasted a good hour and a half. Then again, I was only allowed to tickle one body part and not even the whole part, so I guess that partially explains the time delay so to speak. Still, you held your own pretty good. You definitely challenged my tickling skills which I appreciate.
Jennifer: Oh well I suppose we both learned much from this experience. I’ll tell you this I am never gonna ware these types of nylons ever again to a tickle session. My feet are way too ticklish in them. Nails on these nylons for me just don’t mix hahaha. And you are one hell of a tickler lady!, Them fingernails of yours are the devil himself! I mean yeah my toes are a real hot zone of ticklishness but those nails you got tortured my poor tootsies like I never felt in my life. Congrats again! So, you want to unhook me now? We done right?
Sara looked at me quizzically and to my horror uttered words I certainly did not want to hear.
Sara: Let you go? Hmm, no I don’t think so honey. Remember? You still owe me another HOUR! But since you were so compliant, I think I’ll reward you with another mind shattering orgasm before I tickle you to tears…again hahaha.
Sara pulled a stiff feather from her bag and began to stroke my sopping wet pussy with it. She carefully moved the soft barbs of the feather across my vaginal lips dipping the tip into my love hole occasionally. The teasing strokes of the feather against my now aching loins was devastatingly pleasurable and I moaned in appreciation and lust. She is going to make me cum again, powerfully which will increase my sensitivity to her tickling administrations; a prospect I am both excited for and very, very nervous. I ask myself how will I endure Sara’s torturous fingernails for another hour? Unfortunately, only time will tell.
To be continued
