Glovelover
TMF Regular
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- Dec 28, 2003
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I finally completed a new story. It is a fictional, erotic story that contains very explicit, sexual content. Fair warning if that is not your ‘cup of tea’.
I posted the entire story rather than just posting only the Tickling related content (as with most of my stories, it contains a good bit of background and set-up of the scenario). However, if you want to skip all the ‘set-up’, fast forward to “THE POINT OF NO RETURN” which is just prior to the Tickling content.
Enjoy!
BACKGROUND
Jeff & Tyler knew each other casually from the brief discussions they had over the past several months at a local lounge in the city.
Jeff was in his mid thirties and was tired of the club scene. He found this lounge located in the city near his work and enjoyed becoming part of the regulars there who averaged in age, slightly older than he. On Saturday nights there would either be a piano player or sometimes a small jazz group or guitar performer playing in the lounge. It was actually a place where people could actually sit, talk and enjoy the company of everyone in the place. He was cognizant to avoid being there all the time, in that, he was a regular but did not want to become yet another ‘bar fly’ of a place.
Tyler was a forty something woman who occasionally stopped by the lounge with her friends on Saturday nights after attending the symphony which was located a few blocks down the street. On rarer occasions, she would make an appearance at the lounge during Happy Hour whenever business or an errand brought her into to the city. With the exception of her height, Tyler was not a woman that would stand out in a crowd. She was slender and attractive, but had long, brownish colored hair and did not exude an excessive shapely frame that some people pay big money for.
Now despite Tyler’s conservative persona and appearance, Saturday Nights were a special night out for her. Tyler loved going out to the Symphony or Opera and it was a special girls night out for her. Tyler also had a strong passion for elegance and she would put that too on overdrive as well. It showed as they walked into the lounge after these events for their nightcap. So much so, that Tyler actually stood out when she entered because she was dressed to elegant perfection, which often included a pair of long evening gloves. There were occasions too when her friend Trish would be wearing gloves, however it was Tyler who regularly wore them. Her gloves were the initial catalysts that caught Jeff’s attention the night they met. The sight of a woman wearing gloves like that in public is a true rare thing with the exception of costume parties around Halloween. Thus it was unavoidable for Jeff to miss Tyler’s entrance.
Jeff got to know them initially the first couple of times they were there and he always made it a point to be short and polite with people he met in the lounge, particularly with Tyler and any of her friends. One of those first few times they spoke, Tyler coincidentally was sitting next to him at the bar. They always spoke casually about things and their conversations would never delve towards flirty content. It was a mature, casual friendship.
THE OPPORTUNITY
On one special Saturday, as routine as they were, a different chain of events took place.
Jeff was catching up with a few friends and like clockwork, in came Tyler and Trish to the lounge. Tonight Tyler wore the white gloves and Jeff chuckled to himself “Mmmm, a White Glove Night……Lovely!” However, he curbed his enthusiasm and they just exchanged smiles as they always did as she walked by. Jeff returned to his conversation. Tyler and Trish sat towards the back corner of the place and blended in to the smoky room.
A little while later, Jeff decided to stop by and say a personal “hello” to them which too, was also a typical thing.
Tyler and her friend were chatting as they noticed Jeff approaching. They each smiled back at him giving him a subtle sign that he was not interrupting anything special.
“And how was Haydn’s Symphony No. 45 tonight?” Jeff asked once approaching their table.
“Absolutely lovely!” Tyler responded with a smile.
“Perhaps they will surpass themselves next week” Was Jeff’s response.
They exchanged small talk and Jeff as he normally did excused himself and wished them a wonderful night. Making an effort to not overstay his welcome.
“Why don’t you sit and join us?” Tyler asked.
“I am not about to impose on your night out together” was Jeff’s quickest response. “Besides, I feel underdressed” as a cute way to extend a compliment to their formal attire.
“Don’t be silly, besides I must be going anyhow…….Stay and keep Tyler company.” Trish said as she checked her purse.
“Please sit, you are not imposing and this will give us a chance to talk about something more deeper than the weather or our jobs” Tyler said with a pleasant smile. Her palm was patting the table to emphasize her wish for him to sit and join her.
Jeff tried as best he could to keep it brief and let her do the talking. ‘Breaking the ice’ was not required and they were both at ease with each other and the conversation flowed very effortlessly for each other. He was though struck by how different Tyler looked on these nights out verses the occasional happy hour meetings. Tyler paid so much attention to details of her makeup, accessories, etc., which she actually looked as though she could be at a Hollywood Premier. She was absolutely stunning and that alone made him a little nervous talking with her. Jeff also had a hard time avoiding glancing down at Tyler’s gloves that were neatly folded and laying so innocently on the table.
Their conversation remained casual and each avoided flirtatious content up until the point where Tyler recalled an earlier conversation of theirs.
“Every time I see you Jeff, I always remember that flattering statement you made……” Tyler was referring to an “Elegantly Stunning” description he used one time when he greeted her. Deep down he was referring to her attire coupled with her long evening gloves.
“You know, if I would have had the nerve, I would have kissed your hand too!” Jeff chuckled.
Jeff then inquired why she was not wearing the gloves and letting such a lovely pair lay unused on the table. Jeff deep down was nervous mentioning the word “gloves” to her since they were quite a private secret he kept to himself. Tyler conceded that since they were her favorite white pair, she wanted to avoid getting any stains or smudges on them since they are so hard to clean.
“You could always use the 3 button opening as it was intended” Jeff said with a combination bold, and yet nervous hint in his voice.
“Oh?” Tyler said with a surprise “Please expound!”
Jeff explained the purpose of the opening beneath the wrist as Tyler smiled and leaned into him closer.
“…and just how does a young man from your generation know that unique, little fact?” Tyler softly said with a raised eyebrow.
Jeff was stuck. Inside he knew that this was not a thing of trivia that most people know. Thus an awkward silence resulted as he tried to have his humor dig his way out of this hole.
None-the-less, they both laughed about it yet it confirmed something to Tyler that she perceived previously from her bar friend. ‘Gloves’ must be something ‘more’ to him than he is willing to disclose. With her years of experience and meeting several gentlemen over the years, it became easy for her to suspect when one of them had a fetish, or fixation of some sort. Deep down, she could not blame Jeff. Gloves were a special part of her too and deep down when she thought about it, one would conclude gloves too were a fetish of some sorts to her.
That moment lead the conversation down another path and even though Tyler did not down right confront Jeff about his glove fetish, their conversation moved closer and closer to it. The spontaneity of this conversation coupled with the wine gave Tyler the opportunity to open more of his secret compartment and the more Jeff spoke, the more it confirmed to her that women’s gloves were something that really excited him.
Jeff was getting turned on from this conversation and Tyler’s innocent questions made him slip more and more.
When Tyler was finished with her glass of wine, she took the opportunity and pulled her gloves on to further tease her friend even more. As time went by, their chairs got closer and closer together as their conversation became more ‘private’. She then put everything on the line with one simple question, one that Jeff often fantasized to hear and as she put her gloved hand down to confirm the erection he was hiding. After that question, there was no turning back for either of them.
“How long do you think you could hold yourself back if I stroked you with my gloves!”
Jeff was trembling in his chair and he could not break the eye contact she was giving him. Again, he was at a loss for words and did not know how to respond?
“Of course, there would be strings attached…….conditions of mine that you would have to agree to first.” Tyler said with a pronounced confidence in her words.
“…..and those would be?” Jeff asked in a cautious tone.
Tyler leaned in closer to him and in a sultry, sexy whisper into his ear said…
“I get to tie you up to my bed first!” After saying it Tyler drifted back to her chair, winked at him and noted his reaction.
“Bondage….She’s into Bondage!” Jeff said silently to himself as a wave of nervousness surged deep within his body.
The shock and the tease of it made his mind race with questions as he stared back at her and wondered what was racing through her mind and what devilish ideas she was contemplating. Seeing this new side of Tyler, created a sparkle in her eyes that became so attractive to Jeff.
“So, are we interested?” Tyler asked.
The visual going through his head, of this elegant, older woman securing him to a bed really struck a submissive nerve inside him. Imagining her standing over him and teasing him with her gloves in that situation became a very, erotic and enticing idea. Without much hesitation, Jeff agreed and their journey to this new adventure began.
THE POINT OF NO RETURN
Since Trish drove, Tyler needed a ride home and Jeff naturally offered to do so. The ride did not take too long and soon Jeff was driving up a long driveway to a large house in a remote corner of a nearby town. After parking, Jeff pumped up the courtesy, got out first, walked around and let Tyler out of the car. Tyler extended her gloved hand out as he gently took it, helping and admiring her frame get out of the car. She then took his arm and allowed him to escort her to the door.
Jeff asked for her key and unlocked the door and opened it for her. Tyler was most impressed with his manners and enjoyed this courtesy which made her feel as royalty would feel.
“Please do come in and make yourself comfortable.” Tyler motioned to the family room as she excused herself to freshen up briefly.
“Please pour me a little brandy from the bar and feel free to make yourself a drink if you wish” Tyler last said as she walked upstairs. Taking her earlier hint of brandy, he choose one bottle and poured two small drinks.
As he waited in the room for her, he looked around and saw some photos on the bookshelf. He had to get up and walk closer to see them because something caught his attention. Sure enough, there were a couple photos of Tyler and Trish and to add more torment to the pending question of the night, they were dressed formally and, of course, wearing gloves. One photo in particular must have been at a unique masquerade type ball since they were both wearing masks with Tyler looking slightly different than her normal expression. With the mask, the dark red lipstick and her hair pulled back in a tight pony tail, she resembled more of a Dominatrix which teased him internally more at this time due to her earlier proposition. Jeff even held the frame as he admired her look while he internally compared this image with the ‘normal’ everyday looking woman he knew Tyler as. The contrast was amazing!
“Care for a wallet size?” Tyler teased as she entered. “You just cant leave my gloves alone can you?”
Jeff gasped to himself when he saw her. Tyler slipped out of her dress and was wearing a long, silky black evening gown that hugged and absolutely complimented her figure. It had lace accents in strategic locations and a long slit up the side that allowed him to notice the silky stockings. For his benefit, she completed her attire with a pair of long, black satin gloves. As Tyler approached him, her appearance reminded him of the mysterious, sexy and dangerous women in the Spy Movies. He handed her a glass and they sat down on the couch.
“I wanted to show you something that I know you will appreciate.” Tyler said with enthusiasm as she put down her drink and opened a slender plastic bag. She pulled out and unfolded another pair of ultra long black satin gloves.
“I bought these for another ball Trish and I attended the other year!” Tyler unfolded them and laid part of them on her lap as she focused his concentration on the ends. “They have a pointed hem which points well above my shoulders!” Tyler said with excitement in her voice. “I could not believe some of the looks I got throughout the night and Trish was so jealous she didn’t have a pair too!”
Jeff enjoyed her story but was internally going crazy watching her and thinking about their negotiation. All his mind could do is imagine ‘why’ her price was what it was? The ‘anticipation’ was gnawing at him and he kept wondering what she had in mind after tying him up? Tyler could read from his expressions that he was in this far too much to turn back and was completely confident that Jeff would not have a change of heart, finish his drink and then leave for the night. She could also tell by the folds of the crotch of his trousers that he was still very excited and was not currently thinking with a clear head.
“So? What shall we do next?” Tyler smiled as she sipped from her glass.
She then took her hand and rested it on his leg and slowly slid it up towards Jeff’s crotch. Even through the fabric of his pants and her gloves, she could feel the warmth of his erection. Jeff was quiet and did not say a word. Tyler made the next advance and began undoing his belt, then his zipper, then unbuttoned his shirt. Jeff was entranced as he watched this gloved woman make her advance and obviously had not intent to stop her. She had him stand in front of her as she finished removing his trousers then finally his briefs and in no time Tyler had Jeff standing before her, completely excited and erect. Tyler got up and stated one last requirement as she retrieved the long glove from the table and began wrapping it around his head, effectively using it as a blind fold.
“So, you want me to touch you with my gloves Jeffrey?” Tyler whispered into his ear as she stood behind him, pressing her body hard against his. The silkiness of her gown felt wonderful against his skin.
“Oh My Yes….Please!” Was Jeff’s only response.
“You may carry my other glove for me while we go into the other room.” Tyler said as she laid the other glove over his erect cock. Not being able to see the glove, yet feel it draped over his cock was quite erotic to him.
She took him by the hand and carefully led him upstairs and into another room.
Jeff was positioned to sit on what felt like the side of a bed and was told to stay there a minute while Tyler briefly lit a candle. After a minute or so Tyler gave him commands and had him lay back on the bed. She first placed each wrist to a separate leather cuff. The cuffs were attached to ropes and for the moment, Jeff had plenty of slack to move his arms about. Next he could hear Tyler at the foot of the bed and she carefully positioned his legs. Jeff had became puzzled as his ankles slipped into softly, padded notches and then soon realized his ankles were tightly immobilized when she lowered an upper piece down, effectively locking his ankles into stocks of some sort.
“What?….What are you doing?” Jeff asked in puzzlement.
“Getting you ready.” Tyler said as she walked back up to the head of the bed.
“I am so amazed at how people can be lured into such vulnerable situations by just their sexual desires” Tyler said as she was now removing any slack in the ropes holding the cuffs.
As he was lying there Jeff was realizing that this woman had a much darker persona than he first envisioned. Tyler must really be into bondage and other kinky things to have such a unique bed as he perceived as he lay there feeling more and more helpless.
“Don’t go away……I’ll be right back” was Tyler’s parting words to him as she left briefly to apply some more make-up and finalize her attire. Jeff’s mind drifted to the thoughts of feeling her gloves touching him and also thoughts of the unknown. What else was this woman planning? Soon, she was back in the room to begin this erotic session with her new friend.
Tyler looked at Jeff and smiled at the sight of him stretched tight and helpless. His excitement still showed as his cock remained erect and anticipating her stimulation. Tyler then sat down on the bed next to him, leaned onto him, pressing her body against his.
“So, are you ready to feel my gloves touch your skin?” Tyler said as she kissed him.
Jeff was so ready as this was now beyond any dream come true for him.
Tyler placed her gloved hand over his mouth and nose area allowing Jeff to worship her gloved hand. He took in the aroma of the satin and lightly kissed her palm. Tyler used her other hand and removed the glove/blindfold from his face, allowing him to grasp the full visual of her. He first noticed she applied a much darker shade of lipstick, which looked almost black in the candlelight. She had also applied more makeup accents to emphasize her eyes and finally, a black dot which coupled with the lipstick and makeup, made her look devilishly evil. Jeff’s eyes also savored her body adorned in the sexy gown with her long, soft black gloves.
After granting him a few minutes to worship her hand, Tyler began rubbing her hand around his body very slowly.
“You know Jeffery, we are very similar people, in that, we have unique ‘turn-ons’ that are so very special to us!” Tyler continued caressing his body with her gloved hands “…and I would imagine you would be surprised to know that I too have a fetish, of sorts?”
Jeff was listening but was all too focused on her gloves as he felt them lightly glide over his body and looked at her image.
She glided her hand over his body applying pressure primarily with her palms and smiled as she watched him enjoy the contact. Then, she started to change the contact while applying the pressure more with her gloved fingers and then eventually with her fingertips. Still watching his face, she concentrated on his eye movements, breathing and sounds as her fingertips moving over his body. It wasn’t long until his reactions confirmed that he was trying to fight off a particular reaction from her stimulation.
“Do I detect that you are a bit Ticklish Jeffrey?” Tyler said with a smile.
“yy…Yes……” Jeff said with a tone of uncertainty. “Quite….T..Ticklish…” as he closed his eyes trying to remain in control.
“Then I suppose you’ll be in serious trouble if I did this!” Tyler said as she really began tickling his sides.
Jeff burst out laughing immediately from her tickling and he thrashed back and forth in an effort to escape her fingers.
“Oh my!” Tyler said with a bright smile “You are Ticklish!” Tyler cooed “Cant get away can you!” as she continued tickling his sides for several more seconds, eventually stopping.
Tyler got up from the bed to allow her victim to regain some composure as she retrieved a lighter from the end table, and lit more candles about the room.
Tyler went to a table and retrieved a piece of yarn and then stood at the foot of the bed. Jeff could not see what Tyler was doing since the stocks were rather large and even the tips of his toes were barely visible. He could feel her wrapping his large toes together with the piece of yarn and then tied the remaining length to a hook in the top of the thick, black stocks. He watched her face, her smile as she restrained his feet to the point that movement was quite impossible. The expression on her face clearly showed she was enjoying her new, bound victim.
“Have you figured out what my fetish might be?” Tyler asked with a devilish smile on her face.
He began to look around the room since his eyes were adjusting more to the candlelight and noticed the arrangements strategically placed about the room in vases. In that, each vase held a vast assortment of feathers including Long Ostrich, Peacock, and other various fluffy Feathers. Tyler walked over to one assortment and carefully selected a feather from the vase. Tyler looked at him, smiled and stared back at him as she slowly returned to the foot of the bed. Jeff looked more closely at his helpless position and his intellectual brain finally put it all together.
“Oh God No Tyler…….Not That!” Was Jeff’s first plea to stop the circumstances that he now knew was about to happen.
“Why not?” Tyler cooed with a smile as she leaned on the stocks with her arm, dangling her gloved hand over the edge “You wanted me to touch you with my gloves and we have this wonderful opportunity to both enjoy each other’s passions!”
“You will indulge my interests first, then I will return the favor.” Tyler said as she began to slowly stroke his foot with the feather.
“You should consider yourself lucky!” Tyler said with a smile. “….because I’m very good at this!”
The tickly sensations caused a chill in his spine and he was unable to move his feet away from the stimulation. Tyler smiled as Jeff closed his eyes and attempted to hold back the laughter.
“Stop fighting it or I’ll tickle your ribs again!” Tyler threatened as she continued tickling his feet with her feather.
Jeff’s face was getting red from holding his breath, fighting the urge to laugh and soon he would not be able to hold back any longer.
“I just adore a ticklish man Jeffrey…….Shall I touch you with my glove again?” And with that, Tyler started to stroke his other foot with her finger. She slowly glided it up and down the arch of his foot. Tyler noted by the expressions on his face of the hot spots on his feet and then focused little tickles to each spot.
Her precision of the little tickles soon paid off as Jeff gave up holding back and started laughing.
“There’s my Ticklish Man!” Tyler congratulated him and transitioned her single finger tickle technique into a multiple-finger tickling of his foot.
Her change in technique caused a change in Jeff’s laughter confirming her tickling was effective.
“Don’t my gloves feel wonderful?” Tyler cooed.
Mixed in with his hysterical laughter, all he could mutter were various pleas and whimpers.
“HAHAHAHAA…No More!…HAHAHAHAHAHAA..Please!…HAHAHAHAHAHAHAA..”
After a few minutes, Tyler stopped her tickling and gave Jeff a brief chance to recover.
“Enjoying the ‘touch’ of my gloves?” Tyler inquired?
It took Jeff quite a period to settle down and he then pleaded that being tickled was not what he had in mind. Tyler countered that his erection was still there and deep inside he must enjoy it.
“You said you wanted me to touch you with my gloves?” Tyler countered.
“If you would prefer, I can remove my gloves and use my fingernails?”
Jeff thought about it and quickly concluded that perhaps that option could be worse.
“Tell you what? Why don’t we use that button wrist opening that you are so knowledgeable about and give it a try?” Tyler said as she pulled her one hand through the button opening at the wrist.
Once Tyler tucked the fingertips of the glove back inside, she smiled at him most devilishly and started wiggling her fingers towards him. She had long fingernails and those alone could be deadly against ticklish skin. Jeff begged again in protest as her nails made contact with the soles of his feet. His suspicion was correct, her fingernails tickled much more!
Immediately, Jeff broke out in a fit of helpless laughter again!
“Ooooh!” Tyler reacted with a bright-eyed smile back at him. “Look how Ticklish you are now!”
Again, Jeff struggled to move his feet away from the tickling but it was impossible. His mind was going mad trying to endure this torture and knew he could not for too much longer. All he could do was laugh and beg as best he could in between the laughter. It took less time for Jeff to get into the hysterical state he was in when she gave him the first break. Tyler was correct, she was very good at tickling. Her fingertips and nails glided over his soles with accurate perfection, the right pressure, the right scratchiness and it was driving Jeff absolutely mad. All-the-while his cock remained hard and Tyler teased that deep down something in him loved it!
“Would you like me to stop?” Tyler cooed.
“HAHAHAHAHAHAA……Yessssss………HAHAHAHAHAHAA……Plllllleeeease….HAHAHAHAH”
“What are you willing to do for me?”
“HAHAHAHAHAA……..Anything……HAHAHAHAHAHA……Anything……HAHAHAHAHA”
“Anything?…..Are you sure?” Tyler was now using a single finger to tickle his soles, which lessened the intensity allowing his laughter to subside some to give him a chance to think about his response.
“Perhaps we should start small for the moment……” Tyler said as she watched her finger glide up and down his sole “For I plan to tickle you for a good, long while tonight…..”
“HAHAHA…..Please…….Anything………” Jeff’s laughter was less intense but the tickling was still driving him mad.
“Well, perhaps a special friend could pick up my tab at the lounge on certain nights?” Tyler offered as she applied more pressure and velocity to her strokes.
The tickling sensations intensified and quickly pushed Jeff back into hysterics.
“Noooooooo…..HAHAHAHAHAHA……….I …….WILL………HAHAHAHAHA……I…..WILL”
“Are you sure? We have very expensive tastes!”
“HAHAHAHAHAHA……..YES!………….ANYTHING……………I……..WILL”
Tyler tickled his feet for a few more seconds, making Jeff repeat the new agreement despite his hysterical laughter and then finally stopped to give him a break. She got up, gave him a kiss and briefly left the room. Jeff was settling down as he watched her return to the room. His eyes got big as he noticed Tyler gliding on another pair of gloves. Tyler smiled at him as she stood next to the bed, giving him a show of her gliding on the gloves. These were an older pair of gloves that she had for some time, they were a satin pair that she removed the fingertips from and knew they would be perfect for this particular tickle session. Tyler took a seat next to him on the bed, showed him the gloves and again had him kiss and worship each hand.
“I suppose you deserve some stimulation with which you initially thought you would receive.” Tyler said as she took one hand and began caressing his cock and balls.
Jeff closed his eyes and moaned as he savored the pleasurable stimulation as it was the first time he ever felt a woman caressing his genitals with gloves. Tyler then used both hands and coupled strokes with the satin fabric along with her exposed fingernails to heighten the stimulation. Tyler was watching Jeff closely, reading the excitement level in his face as she gripped his cock harder and started jerking it slowly. The last thing she wanted him to do was to climax this early in the session.
“Oh….Please don’t stop.” Jeff moaned, savoring the sensations building inside.
“And just what are you going to do about it if I do?” Tyler said to remind Jeff of his position.
“Please!!….” Jeff was focused on a building orgasm that was getting close.
And just as Jeff was getting close, Tyler slowed her jerking and then let go of his cock. She laughed as she did to reinforce the frustration Jeff felt as he watched his cock stand there throbbing and longing for some contact as the climaxing urge diminished.
Jeff closed his eyes in frustration.
“That was mean!” Jeff softly whispered.
“Mean? You want to see mean?” Tyler threatened with very serious glance as her gloved hands moved to his torso and began a thunderous, tickle attack of his sides!
There was no way he could fight off this assault and immediately Jeff was thrashing and screaming in laughter as Tyler showed him just how good at tickling she was.
“If you want mean…..I can be verrrrrrrrrrrrrrrrrrrrrrry Meaaaaaaaaaaaaaaaaaaaaaaaaaaaaan!” Tyler said to her helpless victim as she frantically tickled his torso, focusing on each normal tickle-spot and noting his reactions in her mind.
His screams went unnoticed by her and he learned from this exchange that Tyler was actually rather sadistic, deaf to any of his helpless pleas muttered amongst his hysterical laughing, screaming or cries! Eventually, the volume of his screams lessened more and more yet he thrashed violently. Tyler had now taken him to a hard limit in just a matter of seconds. In Jeff’s mind he was going absolutely insane not being able to get away from her fingertips and was dangerously hyperventilating. And as quickly as her tickling assault began, Tyler stopped!
“Relax and try to take slower, deeper breaths” Tyler instructed, helping him to try and calm down. His gasps remained fast for awhile and finally Jeff settled down, yet he felt a rush surging inside his body.
“So, are you going make any more stupid comments?” Tyler said.
Only he could mutter was a hoarse “no”.
“What was that?” Tyler said as her fingertips lightly tickled his sides.
And in a burst of laughter, Jeff screamed “HAAAAA NO TYLER! HAAAAAAHAAAAAAA!” and Tyler stopped her tickling.
She only allowed him a few seconds of rest until she returned to the foot of the bed and with her nails, motioned her intent to resume tickling his feet.
“No……No More……Please!” He pleaded.
“Cootchie….Cootchie!” Tyler said with a smile as her fingernails began stroking his arches.
As before, Jeff bursted out laughing immediately!
Tyler loved tormenting her victims while she tickled them and Jeff proved to be very fun subject since he was quite submissive and horribly ticklish.
Then through the laughter, the phone began ringing. Tyler answered it and Jeff learned it was Trish checking up on her. As Tyler talked on the phone, she continued to periodically tickle his feet.
“Yes, that’s Jeff” Tyler chuckled as she looked back at him. “Yes, I would say he is absolutely Tickled to be here!” Tyler continued chuckling with their exchange “Don’t worry, I’ll be sure to treat him with Kid Gloves!”
Jeff then panicked when Tyler ask “You coming over?”
Tyler was smiling “You sure? He’s VERY TICKLISH!” as she intensified the tickling making Jeff’s laughter louder and more desperate.
Tyler got up, walked around and sat next to Jeff on the bed as he was settling down.
“Would you like to talk to him?”
Then Tyler held the phone to Jeff. “Tell Trish how much you want her to come over!” as she began tickling his sides with her nails.
Amongst his laughter he tried talking but was far to overtaken from her tickling and he just continuously laughed.
“Hear that? He’s just dying for you to come over.” Tyler said with a laugh “See you soon!”
Tyler paused from her tickling to put the phone down on the nightstand and then sat and watched her victim settle down.
“Now where were we?” Tyler asked
“Oh, that’s’ right!” And extended her hands to his sides again.
“No More Tyler.…….Please!” Jeff pleaded knowing the tickling was about to resume. “You’re killing me!”
Tyler removed her fingerless gloves and glided on a pair of white gloves that she wore earlier that evening to the Symphony. She glided them on and resumed stimulating his genitals with them and masturbated him, stroking and pumping his cock. Jeff’s body was quite exhausted, yet her stimulation did not take long to work him again towards a climax.
“I believe you actually enjoy being tickled Jeffery?” Tyler said as she pumped his cock.
“And I think we should make this a more permanent relationship…”
Jeff knew his position now and was not about to disagree or challenge anything Tyler said. Frankly, this was defining a part of who he was deep down and was surrendering completely to her. It was odd how he could be frightened and still excited at submitting to her mix of pleasure and also torture.
“Now, would you like me allow you to come with my gloves?”
“Yes Please….Ms Tyler…..Please!” Were his pleas.
“Fair enough……but how about one last challenge before I do so?” Tyler said as she stopped pumping his cock to deny him yet one more time. Tyler adjusted her gloves as they slipped down her arms and gathered below her elbows.
“If you can hold off from climaxing for three minutes……I’ll let you come, relax and then I’ll untie you.”
“However, if you climax before that time, I’ll cruelly tickle you again like before?”
“Or, I can untie you now with no climax and you may leave?”
Tyler was confident the third option would be unlikely for him to select, however she provided it as a test to confirm he was deep down, enjoying this scene.
“Shall I just untie you now?” Tyler asked again.
Jeff thought as best he could given his current exhaustion and contemplated the challenge. Frankly he (as well as Tyler) knew the odds were stacked in her favor.
“No, Tyler please….. Please allow me to come.”
“Okay then, here we go!” Tyler said as she looked at a clock in the room and started pumping his cock.
Her strokes were slow at first and as the seconds ticked away, her frequency increased. The sensation of her glove hand pumping his cock felt amazing and Jeff enjoyed the building urge inside while still trying to not let it build beyond control. Watching Tyler in her gloves contributed to the stimulation and Jeff quickly realized within only the first minute that Tyler might succeed within the deadline. Thus, he closed his eyes to shield this contribution.
“Oh no you don’t!” Tyler objected as she briefly tickled his side with her other hand. “Eyes Open!”
Tyler could tell by his breathing and moans that he was getting close.
“You’re getting close…..” Tyler cooed as she took her other hand, gently stroked his sack while her other hand increased its tempo.
Jeff feared the reality of being subject to more of her tickling, however his urge to climax was just getting too much despite his efforts to maintain control. He could feel his body giving in. Tyler too could read it in his eyes and began squeezing the base of his cock with her free hand to help him hold it back. He didn’t even make it to two minutes yet.
“You’re not gonna make it…… are you?” She cooed as she looked over at the clock.
“No…I’m gonna…” Was all he could mutter as he held back his climax for the last few seconds.
“Are you my new Tickle Slave Jeffrey?” She said as she clamped the base harder…holding him back.
“Yes……..yes…….Tyler….” He whispered as he left go of all control as Tyler let go of the base and slowly pumped with her hand.
It was several hours since his excitement began earlier that evening at the lounge, thus the build-up to this ejaculation was long in the making. Jeff’s body lurched as he let out a loud moan while a warm stream shot from his penis and landed on his chest. Tyler smiled as she watched the semen stream from his cock. Once the throbbing subsided, she left go of his member and allowed Jeff relax and relish the pleasure for a few seconds.
Until…..
Her gloved fingertips returned to his sides and slowly began pinching and squeezing his torso. Jeff quickly learned how sensitive, i.e., more ticklish people can be after climaxing. Immediately, he thrashed and screamed trying to escape this final tickling assault from Tyler. This period of tickling consisted of her going full circle around the bed. She tickled him from his armpits, down his sides, his hips, and down his legs. When she tickled his feet, she demonstrated how effective the feather was with his newly enhanced sensitivity and ticklishness. She verbally continued tormenting him during this last period calling him names, questioning him and getting him to agree to just about anything if she would stop tickling him. She tickled her way back up his legs, his hips and finished at his sides one last time. Jeff was reaching that hard limit again and finally, she stopped!
As Jeff slowly calmed down this last time, Tyler was quick to point out that his cock that was going flaccid when she began tickling him, and now it was actually slightly erect again.
Jeff’s body was limp as Tyler loosened each restraint and released his legs from the stocks. Tyler then removed her gown and all that remained were her gloves, stockings and garter. She stepped up on the bed and climbed over him.
“Now its your turn….” Tyler said as she lowered herself towards his face…….
Even though Jeff was exhausted, he gathered all the energy he could to pleasure her and bring her to a climax. It was obvious how turned on she was from their session and Jeff did the best he could to bring Tyler to climax since this actually was rather new to him. With her help by subtle instructions, his efforts became successful as she grabbed his head hard, pressed him tight against her and she finally exploded in orgasm!
Their erotic night had finally ended, however Tyler recommended Jeff sleep there the remainder of the night since he was so exhausted from her session.
He slept on a couch in the family room, awoke before she did and prepared a nice breakfast for her to enjoy before he left.
As he drove home his mind recalled the events of that erotic night. He fondled the white gloves she wore at the end of the session that became soiled. Tyler left him have them as a remembrance as well as to have them cleaned and ready for their next time together. Suddenly, a message vibrated on his phone. It was from Tyler and included a photo taken by a camera hidden in the room while she tickled him. A message from her said
“Until next time, my dearest Glove Loving Tickle Slave!”
The End (for now)
I posted the entire story rather than just posting only the Tickling related content (as with most of my stories, it contains a good bit of background and set-up of the scenario). However, if you want to skip all the ‘set-up’, fast forward to “THE POINT OF NO RETURN” which is just prior to the Tickling content.
Enjoy!
BACKGROUND
Jeff & Tyler knew each other casually from the brief discussions they had over the past several months at a local lounge in the city.
Jeff was in his mid thirties and was tired of the club scene. He found this lounge located in the city near his work and enjoyed becoming part of the regulars there who averaged in age, slightly older than he. On Saturday nights there would either be a piano player or sometimes a small jazz group or guitar performer playing in the lounge. It was actually a place where people could actually sit, talk and enjoy the company of everyone in the place. He was cognizant to avoid being there all the time, in that, he was a regular but did not want to become yet another ‘bar fly’ of a place.
Tyler was a forty something woman who occasionally stopped by the lounge with her friends on Saturday nights after attending the symphony which was located a few blocks down the street. On rarer occasions, she would make an appearance at the lounge during Happy Hour whenever business or an errand brought her into to the city. With the exception of her height, Tyler was not a woman that would stand out in a crowd. She was slender and attractive, but had long, brownish colored hair and did not exude an excessive shapely frame that some people pay big money for.
Now despite Tyler’s conservative persona and appearance, Saturday Nights were a special night out for her. Tyler loved going out to the Symphony or Opera and it was a special girls night out for her. Tyler also had a strong passion for elegance and she would put that too on overdrive as well. It showed as they walked into the lounge after these events for their nightcap. So much so, that Tyler actually stood out when she entered because she was dressed to elegant perfection, which often included a pair of long evening gloves. There were occasions too when her friend Trish would be wearing gloves, however it was Tyler who regularly wore them. Her gloves were the initial catalysts that caught Jeff’s attention the night they met. The sight of a woman wearing gloves like that in public is a true rare thing with the exception of costume parties around Halloween. Thus it was unavoidable for Jeff to miss Tyler’s entrance.
Jeff got to know them initially the first couple of times they were there and he always made it a point to be short and polite with people he met in the lounge, particularly with Tyler and any of her friends. One of those first few times they spoke, Tyler coincidentally was sitting next to him at the bar. They always spoke casually about things and their conversations would never delve towards flirty content. It was a mature, casual friendship.
THE OPPORTUNITY
On one special Saturday, as routine as they were, a different chain of events took place.
Jeff was catching up with a few friends and like clockwork, in came Tyler and Trish to the lounge. Tonight Tyler wore the white gloves and Jeff chuckled to himself “Mmmm, a White Glove Night……Lovely!” However, he curbed his enthusiasm and they just exchanged smiles as they always did as she walked by. Jeff returned to his conversation. Tyler and Trish sat towards the back corner of the place and blended in to the smoky room.
A little while later, Jeff decided to stop by and say a personal “hello” to them which too, was also a typical thing.
Tyler and her friend were chatting as they noticed Jeff approaching. They each smiled back at him giving him a subtle sign that he was not interrupting anything special.
“And how was Haydn’s Symphony No. 45 tonight?” Jeff asked once approaching their table.
“Absolutely lovely!” Tyler responded with a smile.
“Perhaps they will surpass themselves next week” Was Jeff’s response.
They exchanged small talk and Jeff as he normally did excused himself and wished them a wonderful night. Making an effort to not overstay his welcome.
“Why don’t you sit and join us?” Tyler asked.
“I am not about to impose on your night out together” was Jeff’s quickest response. “Besides, I feel underdressed” as a cute way to extend a compliment to their formal attire.
“Don’t be silly, besides I must be going anyhow…….Stay and keep Tyler company.” Trish said as she checked her purse.
“Please sit, you are not imposing and this will give us a chance to talk about something more deeper than the weather or our jobs” Tyler said with a pleasant smile. Her palm was patting the table to emphasize her wish for him to sit and join her.
Jeff tried as best he could to keep it brief and let her do the talking. ‘Breaking the ice’ was not required and they were both at ease with each other and the conversation flowed very effortlessly for each other. He was though struck by how different Tyler looked on these nights out verses the occasional happy hour meetings. Tyler paid so much attention to details of her makeup, accessories, etc., which she actually looked as though she could be at a Hollywood Premier. She was absolutely stunning and that alone made him a little nervous talking with her. Jeff also had a hard time avoiding glancing down at Tyler’s gloves that were neatly folded and laying so innocently on the table.
Their conversation remained casual and each avoided flirtatious content up until the point where Tyler recalled an earlier conversation of theirs.
“Every time I see you Jeff, I always remember that flattering statement you made……” Tyler was referring to an “Elegantly Stunning” description he used one time when he greeted her. Deep down he was referring to her attire coupled with her long evening gloves.
“You know, if I would have had the nerve, I would have kissed your hand too!” Jeff chuckled.
Jeff then inquired why she was not wearing the gloves and letting such a lovely pair lay unused on the table. Jeff deep down was nervous mentioning the word “gloves” to her since they were quite a private secret he kept to himself. Tyler conceded that since they were her favorite white pair, she wanted to avoid getting any stains or smudges on them since they are so hard to clean.
“You could always use the 3 button opening as it was intended” Jeff said with a combination bold, and yet nervous hint in his voice.
“Oh?” Tyler said with a surprise “Please expound!”
Jeff explained the purpose of the opening beneath the wrist as Tyler smiled and leaned into him closer.
“…and just how does a young man from your generation know that unique, little fact?” Tyler softly said with a raised eyebrow.
Jeff was stuck. Inside he knew that this was not a thing of trivia that most people know. Thus an awkward silence resulted as he tried to have his humor dig his way out of this hole.
None-the-less, they both laughed about it yet it confirmed something to Tyler that she perceived previously from her bar friend. ‘Gloves’ must be something ‘more’ to him than he is willing to disclose. With her years of experience and meeting several gentlemen over the years, it became easy for her to suspect when one of them had a fetish, or fixation of some sort. Deep down, she could not blame Jeff. Gloves were a special part of her too and deep down when she thought about it, one would conclude gloves too were a fetish of some sorts to her.
That moment lead the conversation down another path and even though Tyler did not down right confront Jeff about his glove fetish, their conversation moved closer and closer to it. The spontaneity of this conversation coupled with the wine gave Tyler the opportunity to open more of his secret compartment and the more Jeff spoke, the more it confirmed to her that women’s gloves were something that really excited him.
Jeff was getting turned on from this conversation and Tyler’s innocent questions made him slip more and more.
When Tyler was finished with her glass of wine, she took the opportunity and pulled her gloves on to further tease her friend even more. As time went by, their chairs got closer and closer together as their conversation became more ‘private’. She then put everything on the line with one simple question, one that Jeff often fantasized to hear and as she put her gloved hand down to confirm the erection he was hiding. After that question, there was no turning back for either of them.
“How long do you think you could hold yourself back if I stroked you with my gloves!”
Jeff was trembling in his chair and he could not break the eye contact she was giving him. Again, he was at a loss for words and did not know how to respond?
“Of course, there would be strings attached…….conditions of mine that you would have to agree to first.” Tyler said with a pronounced confidence in her words.
“…..and those would be?” Jeff asked in a cautious tone.
Tyler leaned in closer to him and in a sultry, sexy whisper into his ear said…
“I get to tie you up to my bed first!” After saying it Tyler drifted back to her chair, winked at him and noted his reaction.
“Bondage….She’s into Bondage!” Jeff said silently to himself as a wave of nervousness surged deep within his body.
The shock and the tease of it made his mind race with questions as he stared back at her and wondered what was racing through her mind and what devilish ideas she was contemplating. Seeing this new side of Tyler, created a sparkle in her eyes that became so attractive to Jeff.
“So, are we interested?” Tyler asked.
The visual going through his head, of this elegant, older woman securing him to a bed really struck a submissive nerve inside him. Imagining her standing over him and teasing him with her gloves in that situation became a very, erotic and enticing idea. Without much hesitation, Jeff agreed and their journey to this new adventure began.
THE POINT OF NO RETURN
Since Trish drove, Tyler needed a ride home and Jeff naturally offered to do so. The ride did not take too long and soon Jeff was driving up a long driveway to a large house in a remote corner of a nearby town. After parking, Jeff pumped up the courtesy, got out first, walked around and let Tyler out of the car. Tyler extended her gloved hand out as he gently took it, helping and admiring her frame get out of the car. She then took his arm and allowed him to escort her to the door.
Jeff asked for her key and unlocked the door and opened it for her. Tyler was most impressed with his manners and enjoyed this courtesy which made her feel as royalty would feel.
“Please do come in and make yourself comfortable.” Tyler motioned to the family room as she excused herself to freshen up briefly.
“Please pour me a little brandy from the bar and feel free to make yourself a drink if you wish” Tyler last said as she walked upstairs. Taking her earlier hint of brandy, he choose one bottle and poured two small drinks.
As he waited in the room for her, he looked around and saw some photos on the bookshelf. He had to get up and walk closer to see them because something caught his attention. Sure enough, there were a couple photos of Tyler and Trish and to add more torment to the pending question of the night, they were dressed formally and, of course, wearing gloves. One photo in particular must have been at a unique masquerade type ball since they were both wearing masks with Tyler looking slightly different than her normal expression. With the mask, the dark red lipstick and her hair pulled back in a tight pony tail, she resembled more of a Dominatrix which teased him internally more at this time due to her earlier proposition. Jeff even held the frame as he admired her look while he internally compared this image with the ‘normal’ everyday looking woman he knew Tyler as. The contrast was amazing!
“Care for a wallet size?” Tyler teased as she entered. “You just cant leave my gloves alone can you?”
Jeff gasped to himself when he saw her. Tyler slipped out of her dress and was wearing a long, silky black evening gown that hugged and absolutely complimented her figure. It had lace accents in strategic locations and a long slit up the side that allowed him to notice the silky stockings. For his benefit, she completed her attire with a pair of long, black satin gloves. As Tyler approached him, her appearance reminded him of the mysterious, sexy and dangerous women in the Spy Movies. He handed her a glass and they sat down on the couch.
“I wanted to show you something that I know you will appreciate.” Tyler said with enthusiasm as she put down her drink and opened a slender plastic bag. She pulled out and unfolded another pair of ultra long black satin gloves.
“I bought these for another ball Trish and I attended the other year!” Tyler unfolded them and laid part of them on her lap as she focused his concentration on the ends. “They have a pointed hem which points well above my shoulders!” Tyler said with excitement in her voice. “I could not believe some of the looks I got throughout the night and Trish was so jealous she didn’t have a pair too!”
Jeff enjoyed her story but was internally going crazy watching her and thinking about their negotiation. All his mind could do is imagine ‘why’ her price was what it was? The ‘anticipation’ was gnawing at him and he kept wondering what she had in mind after tying him up? Tyler could read from his expressions that he was in this far too much to turn back and was completely confident that Jeff would not have a change of heart, finish his drink and then leave for the night. She could also tell by the folds of the crotch of his trousers that he was still very excited and was not currently thinking with a clear head.
“So? What shall we do next?” Tyler smiled as she sipped from her glass.
She then took her hand and rested it on his leg and slowly slid it up towards Jeff’s crotch. Even through the fabric of his pants and her gloves, she could feel the warmth of his erection. Jeff was quiet and did not say a word. Tyler made the next advance and began undoing his belt, then his zipper, then unbuttoned his shirt. Jeff was entranced as he watched this gloved woman make her advance and obviously had not intent to stop her. She had him stand in front of her as she finished removing his trousers then finally his briefs and in no time Tyler had Jeff standing before her, completely excited and erect. Tyler got up and stated one last requirement as she retrieved the long glove from the table and began wrapping it around his head, effectively using it as a blind fold.
“So, you want me to touch you with my gloves Jeffrey?” Tyler whispered into his ear as she stood behind him, pressing her body hard against his. The silkiness of her gown felt wonderful against his skin.
“Oh My Yes….Please!” Was Jeff’s only response.
“You may carry my other glove for me while we go into the other room.” Tyler said as she laid the other glove over his erect cock. Not being able to see the glove, yet feel it draped over his cock was quite erotic to him.
She took him by the hand and carefully led him upstairs and into another room.
Jeff was positioned to sit on what felt like the side of a bed and was told to stay there a minute while Tyler briefly lit a candle. After a minute or so Tyler gave him commands and had him lay back on the bed. She first placed each wrist to a separate leather cuff. The cuffs were attached to ropes and for the moment, Jeff had plenty of slack to move his arms about. Next he could hear Tyler at the foot of the bed and she carefully positioned his legs. Jeff had became puzzled as his ankles slipped into softly, padded notches and then soon realized his ankles were tightly immobilized when she lowered an upper piece down, effectively locking his ankles into stocks of some sort.
“What?….What are you doing?” Jeff asked in puzzlement.
“Getting you ready.” Tyler said as she walked back up to the head of the bed.
“I am so amazed at how people can be lured into such vulnerable situations by just their sexual desires” Tyler said as she was now removing any slack in the ropes holding the cuffs.
As he was lying there Jeff was realizing that this woman had a much darker persona than he first envisioned. Tyler must really be into bondage and other kinky things to have such a unique bed as he perceived as he lay there feeling more and more helpless.
“Don’t go away……I’ll be right back” was Tyler’s parting words to him as she left briefly to apply some more make-up and finalize her attire. Jeff’s mind drifted to the thoughts of feeling her gloves touching him and also thoughts of the unknown. What else was this woman planning? Soon, she was back in the room to begin this erotic session with her new friend.
Tyler looked at Jeff and smiled at the sight of him stretched tight and helpless. His excitement still showed as his cock remained erect and anticipating her stimulation. Tyler then sat down on the bed next to him, leaned onto him, pressing her body against his.
“So, are you ready to feel my gloves touch your skin?” Tyler said as she kissed him.
Jeff was so ready as this was now beyond any dream come true for him.
Tyler placed her gloved hand over his mouth and nose area allowing Jeff to worship her gloved hand. He took in the aroma of the satin and lightly kissed her palm. Tyler used her other hand and removed the glove/blindfold from his face, allowing him to grasp the full visual of her. He first noticed she applied a much darker shade of lipstick, which looked almost black in the candlelight. She had also applied more makeup accents to emphasize her eyes and finally, a black dot which coupled with the lipstick and makeup, made her look devilishly evil. Jeff’s eyes also savored her body adorned in the sexy gown with her long, soft black gloves.
After granting him a few minutes to worship her hand, Tyler began rubbing her hand around his body very slowly.
“You know Jeffery, we are very similar people, in that, we have unique ‘turn-ons’ that are so very special to us!” Tyler continued caressing his body with her gloved hands “…and I would imagine you would be surprised to know that I too have a fetish, of sorts?”
Jeff was listening but was all too focused on her gloves as he felt them lightly glide over his body and looked at her image.
She glided her hand over his body applying pressure primarily with her palms and smiled as she watched him enjoy the contact. Then, she started to change the contact while applying the pressure more with her gloved fingers and then eventually with her fingertips. Still watching his face, she concentrated on his eye movements, breathing and sounds as her fingertips moving over his body. It wasn’t long until his reactions confirmed that he was trying to fight off a particular reaction from her stimulation.
“Do I detect that you are a bit Ticklish Jeffrey?” Tyler said with a smile.
“yy…Yes……” Jeff said with a tone of uncertainty. “Quite….T..Ticklish…” as he closed his eyes trying to remain in control.
“Then I suppose you’ll be in serious trouble if I did this!” Tyler said as she really began tickling his sides.
Jeff burst out laughing immediately from her tickling and he thrashed back and forth in an effort to escape her fingers.
“Oh my!” Tyler said with a bright smile “You are Ticklish!” Tyler cooed “Cant get away can you!” as she continued tickling his sides for several more seconds, eventually stopping.
Tyler got up from the bed to allow her victim to regain some composure as she retrieved a lighter from the end table, and lit more candles about the room.
Tyler went to a table and retrieved a piece of yarn and then stood at the foot of the bed. Jeff could not see what Tyler was doing since the stocks were rather large and even the tips of his toes were barely visible. He could feel her wrapping his large toes together with the piece of yarn and then tied the remaining length to a hook in the top of the thick, black stocks. He watched her face, her smile as she restrained his feet to the point that movement was quite impossible. The expression on her face clearly showed she was enjoying her new, bound victim.
“Have you figured out what my fetish might be?” Tyler asked with a devilish smile on her face.
He began to look around the room since his eyes were adjusting more to the candlelight and noticed the arrangements strategically placed about the room in vases. In that, each vase held a vast assortment of feathers including Long Ostrich, Peacock, and other various fluffy Feathers. Tyler walked over to one assortment and carefully selected a feather from the vase. Tyler looked at him, smiled and stared back at him as she slowly returned to the foot of the bed. Jeff looked more closely at his helpless position and his intellectual brain finally put it all together.
“Oh God No Tyler…….Not That!” Was Jeff’s first plea to stop the circumstances that he now knew was about to happen.
“Why not?” Tyler cooed with a smile as she leaned on the stocks with her arm, dangling her gloved hand over the edge “You wanted me to touch you with my gloves and we have this wonderful opportunity to both enjoy each other’s passions!”
“You will indulge my interests first, then I will return the favor.” Tyler said as she began to slowly stroke his foot with the feather.
“You should consider yourself lucky!” Tyler said with a smile. “….because I’m very good at this!”
The tickly sensations caused a chill in his spine and he was unable to move his feet away from the stimulation. Tyler smiled as Jeff closed his eyes and attempted to hold back the laughter.
“Stop fighting it or I’ll tickle your ribs again!” Tyler threatened as she continued tickling his feet with her feather.
Jeff’s face was getting red from holding his breath, fighting the urge to laugh and soon he would not be able to hold back any longer.
“I just adore a ticklish man Jeffrey…….Shall I touch you with my glove again?” And with that, Tyler started to stroke his other foot with her finger. She slowly glided it up and down the arch of his foot. Tyler noted by the expressions on his face of the hot spots on his feet and then focused little tickles to each spot.
Her precision of the little tickles soon paid off as Jeff gave up holding back and started laughing.
“There’s my Ticklish Man!” Tyler congratulated him and transitioned her single finger tickle technique into a multiple-finger tickling of his foot.
Her change in technique caused a change in Jeff’s laughter confirming her tickling was effective.
“Don’t my gloves feel wonderful?” Tyler cooed.
Mixed in with his hysterical laughter, all he could mutter were various pleas and whimpers.
“HAHAHAHAA…No More!…HAHAHAHAHAHAA..Please!…HAHAHAHAHAHAHAA..”
After a few minutes, Tyler stopped her tickling and gave Jeff a brief chance to recover.
“Enjoying the ‘touch’ of my gloves?” Tyler inquired?
It took Jeff quite a period to settle down and he then pleaded that being tickled was not what he had in mind. Tyler countered that his erection was still there and deep inside he must enjoy it.
“You said you wanted me to touch you with my gloves?” Tyler countered.
“If you would prefer, I can remove my gloves and use my fingernails?”
Jeff thought about it and quickly concluded that perhaps that option could be worse.
“Tell you what? Why don’t we use that button wrist opening that you are so knowledgeable about and give it a try?” Tyler said as she pulled her one hand through the button opening at the wrist.
Once Tyler tucked the fingertips of the glove back inside, she smiled at him most devilishly and started wiggling her fingers towards him. She had long fingernails and those alone could be deadly against ticklish skin. Jeff begged again in protest as her nails made contact with the soles of his feet. His suspicion was correct, her fingernails tickled much more!
Immediately, Jeff broke out in a fit of helpless laughter again!
“Ooooh!” Tyler reacted with a bright-eyed smile back at him. “Look how Ticklish you are now!”
Again, Jeff struggled to move his feet away from the tickling but it was impossible. His mind was going mad trying to endure this torture and knew he could not for too much longer. All he could do was laugh and beg as best he could in between the laughter. It took less time for Jeff to get into the hysterical state he was in when she gave him the first break. Tyler was correct, she was very good at tickling. Her fingertips and nails glided over his soles with accurate perfection, the right pressure, the right scratchiness and it was driving Jeff absolutely mad. All-the-while his cock remained hard and Tyler teased that deep down something in him loved it!
“Would you like me to stop?” Tyler cooed.
“HAHAHAHAHAHAA……Yessssss………HAHAHAHAHAHAA……Plllllleeeease….HAHAHAHAH”
“What are you willing to do for me?”
“HAHAHAHAHAA……..Anything……HAHAHAHAHAHA……Anything……HAHAHAHAHA”
“Anything?…..Are you sure?” Tyler was now using a single finger to tickle his soles, which lessened the intensity allowing his laughter to subside some to give him a chance to think about his response.
“Perhaps we should start small for the moment……” Tyler said as she watched her finger glide up and down his sole “For I plan to tickle you for a good, long while tonight…..”
“HAHAHA…..Please…….Anything………” Jeff’s laughter was less intense but the tickling was still driving him mad.
“Well, perhaps a special friend could pick up my tab at the lounge on certain nights?” Tyler offered as she applied more pressure and velocity to her strokes.
The tickling sensations intensified and quickly pushed Jeff back into hysterics.
“Noooooooo…..HAHAHAHAHAHA……….I …….WILL………HAHAHAHAHA……I…..WILL”
“Are you sure? We have very expensive tastes!”
“HAHAHAHAHAHA……..YES!………….ANYTHING……………I……..WILL”
Tyler tickled his feet for a few more seconds, making Jeff repeat the new agreement despite his hysterical laughter and then finally stopped to give him a break. She got up, gave him a kiss and briefly left the room. Jeff was settling down as he watched her return to the room. His eyes got big as he noticed Tyler gliding on another pair of gloves. Tyler smiled at him as she stood next to the bed, giving him a show of her gliding on the gloves. These were an older pair of gloves that she had for some time, they were a satin pair that she removed the fingertips from and knew they would be perfect for this particular tickle session. Tyler took a seat next to him on the bed, showed him the gloves and again had him kiss and worship each hand.
“I suppose you deserve some stimulation with which you initially thought you would receive.” Tyler said as she took one hand and began caressing his cock and balls.
Jeff closed his eyes and moaned as he savored the pleasurable stimulation as it was the first time he ever felt a woman caressing his genitals with gloves. Tyler then used both hands and coupled strokes with the satin fabric along with her exposed fingernails to heighten the stimulation. Tyler was watching Jeff closely, reading the excitement level in his face as she gripped his cock harder and started jerking it slowly. The last thing she wanted him to do was to climax this early in the session.
“Oh….Please don’t stop.” Jeff moaned, savoring the sensations building inside.
“And just what are you going to do about it if I do?” Tyler said to remind Jeff of his position.
“Please!!….” Jeff was focused on a building orgasm that was getting close.
And just as Jeff was getting close, Tyler slowed her jerking and then let go of his cock. She laughed as she did to reinforce the frustration Jeff felt as he watched his cock stand there throbbing and longing for some contact as the climaxing urge diminished.
Jeff closed his eyes in frustration.
“That was mean!” Jeff softly whispered.
“Mean? You want to see mean?” Tyler threatened with very serious glance as her gloved hands moved to his torso and began a thunderous, tickle attack of his sides!
There was no way he could fight off this assault and immediately Jeff was thrashing and screaming in laughter as Tyler showed him just how good at tickling she was.
“If you want mean…..I can be verrrrrrrrrrrrrrrrrrrrrrry Meaaaaaaaaaaaaaaaaaaaaaaaaaaaaan!” Tyler said to her helpless victim as she frantically tickled his torso, focusing on each normal tickle-spot and noting his reactions in her mind.
His screams went unnoticed by her and he learned from this exchange that Tyler was actually rather sadistic, deaf to any of his helpless pleas muttered amongst his hysterical laughing, screaming or cries! Eventually, the volume of his screams lessened more and more yet he thrashed violently. Tyler had now taken him to a hard limit in just a matter of seconds. In Jeff’s mind he was going absolutely insane not being able to get away from her fingertips and was dangerously hyperventilating. And as quickly as her tickling assault began, Tyler stopped!
“Relax and try to take slower, deeper breaths” Tyler instructed, helping him to try and calm down. His gasps remained fast for awhile and finally Jeff settled down, yet he felt a rush surging inside his body.
“So, are you going make any more stupid comments?” Tyler said.
Only he could mutter was a hoarse “no”.
“What was that?” Tyler said as her fingertips lightly tickled his sides.
And in a burst of laughter, Jeff screamed “HAAAAA NO TYLER! HAAAAAAHAAAAAAA!” and Tyler stopped her tickling.
She only allowed him a few seconds of rest until she returned to the foot of the bed and with her nails, motioned her intent to resume tickling his feet.
“No……No More……Please!” He pleaded.
“Cootchie….Cootchie!” Tyler said with a smile as her fingernails began stroking his arches.
As before, Jeff bursted out laughing immediately!
Tyler loved tormenting her victims while she tickled them and Jeff proved to be very fun subject since he was quite submissive and horribly ticklish.
Then through the laughter, the phone began ringing. Tyler answered it and Jeff learned it was Trish checking up on her. As Tyler talked on the phone, she continued to periodically tickle his feet.
“Yes, that’s Jeff” Tyler chuckled as she looked back at him. “Yes, I would say he is absolutely Tickled to be here!” Tyler continued chuckling with their exchange “Don’t worry, I’ll be sure to treat him with Kid Gloves!”
Jeff then panicked when Tyler ask “You coming over?”
Tyler was smiling “You sure? He’s VERY TICKLISH!” as she intensified the tickling making Jeff’s laughter louder and more desperate.
Tyler got up, walked around and sat next to Jeff on the bed as he was settling down.
“Would you like to talk to him?”
Then Tyler held the phone to Jeff. “Tell Trish how much you want her to come over!” as she began tickling his sides with her nails.
Amongst his laughter he tried talking but was far to overtaken from her tickling and he just continuously laughed.
“Hear that? He’s just dying for you to come over.” Tyler said with a laugh “See you soon!”
Tyler paused from her tickling to put the phone down on the nightstand and then sat and watched her victim settle down.
“Now where were we?” Tyler asked
“Oh, that’s’ right!” And extended her hands to his sides again.
“No More Tyler.…….Please!” Jeff pleaded knowing the tickling was about to resume. “You’re killing me!”
Tyler removed her fingerless gloves and glided on a pair of white gloves that she wore earlier that evening to the Symphony. She glided them on and resumed stimulating his genitals with them and masturbated him, stroking and pumping his cock. Jeff’s body was quite exhausted, yet her stimulation did not take long to work him again towards a climax.
“I believe you actually enjoy being tickled Jeffery?” Tyler said as she pumped his cock.
“And I think we should make this a more permanent relationship…”
Jeff knew his position now and was not about to disagree or challenge anything Tyler said. Frankly, this was defining a part of who he was deep down and was surrendering completely to her. It was odd how he could be frightened and still excited at submitting to her mix of pleasure and also torture.
“Now, would you like me allow you to come with my gloves?”
“Yes Please….Ms Tyler…..Please!” Were his pleas.
“Fair enough……but how about one last challenge before I do so?” Tyler said as she stopped pumping his cock to deny him yet one more time. Tyler adjusted her gloves as they slipped down her arms and gathered below her elbows.
“If you can hold off from climaxing for three minutes……I’ll let you come, relax and then I’ll untie you.”
“However, if you climax before that time, I’ll cruelly tickle you again like before?”
“Or, I can untie you now with no climax and you may leave?”
Tyler was confident the third option would be unlikely for him to select, however she provided it as a test to confirm he was deep down, enjoying this scene.
“Shall I just untie you now?” Tyler asked again.
Jeff thought as best he could given his current exhaustion and contemplated the challenge. Frankly he (as well as Tyler) knew the odds were stacked in her favor.
“No, Tyler please….. Please allow me to come.”
“Okay then, here we go!” Tyler said as she looked at a clock in the room and started pumping his cock.
Her strokes were slow at first and as the seconds ticked away, her frequency increased. The sensation of her glove hand pumping his cock felt amazing and Jeff enjoyed the building urge inside while still trying to not let it build beyond control. Watching Tyler in her gloves contributed to the stimulation and Jeff quickly realized within only the first minute that Tyler might succeed within the deadline. Thus, he closed his eyes to shield this contribution.
“Oh no you don’t!” Tyler objected as she briefly tickled his side with her other hand. “Eyes Open!”
Tyler could tell by his breathing and moans that he was getting close.
“You’re getting close…..” Tyler cooed as she took her other hand, gently stroked his sack while her other hand increased its tempo.
Jeff feared the reality of being subject to more of her tickling, however his urge to climax was just getting too much despite his efforts to maintain control. He could feel his body giving in. Tyler too could read it in his eyes and began squeezing the base of his cock with her free hand to help him hold it back. He didn’t even make it to two minutes yet.
“You’re not gonna make it…… are you?” She cooed as she looked over at the clock.
“No…I’m gonna…” Was all he could mutter as he held back his climax for the last few seconds.
“Are you my new Tickle Slave Jeffrey?” She said as she clamped the base harder…holding him back.
“Yes……..yes…….Tyler….” He whispered as he left go of all control as Tyler let go of the base and slowly pumped with her hand.
It was several hours since his excitement began earlier that evening at the lounge, thus the build-up to this ejaculation was long in the making. Jeff’s body lurched as he let out a loud moan while a warm stream shot from his penis and landed on his chest. Tyler smiled as she watched the semen stream from his cock. Once the throbbing subsided, she left go of his member and allowed Jeff relax and relish the pleasure for a few seconds.
Until…..
Her gloved fingertips returned to his sides and slowly began pinching and squeezing his torso. Jeff quickly learned how sensitive, i.e., more ticklish people can be after climaxing. Immediately, he thrashed and screamed trying to escape this final tickling assault from Tyler. This period of tickling consisted of her going full circle around the bed. She tickled him from his armpits, down his sides, his hips, and down his legs. When she tickled his feet, she demonstrated how effective the feather was with his newly enhanced sensitivity and ticklishness. She verbally continued tormenting him during this last period calling him names, questioning him and getting him to agree to just about anything if she would stop tickling him. She tickled her way back up his legs, his hips and finished at his sides one last time. Jeff was reaching that hard limit again and finally, she stopped!
As Jeff slowly calmed down this last time, Tyler was quick to point out that his cock that was going flaccid when she began tickling him, and now it was actually slightly erect again.
Jeff’s body was limp as Tyler loosened each restraint and released his legs from the stocks. Tyler then removed her gown and all that remained were her gloves, stockings and garter. She stepped up on the bed and climbed over him.
“Now its your turn….” Tyler said as she lowered herself towards his face…….
Even though Jeff was exhausted, he gathered all the energy he could to pleasure her and bring her to a climax. It was obvious how turned on she was from their session and Jeff did the best he could to bring Tyler to climax since this actually was rather new to him. With her help by subtle instructions, his efforts became successful as she grabbed his head hard, pressed him tight against her and she finally exploded in orgasm!
Their erotic night had finally ended, however Tyler recommended Jeff sleep there the remainder of the night since he was so exhausted from her session.
He slept on a couch in the family room, awoke before she did and prepared a nice breakfast for her to enjoy before he left.
As he drove home his mind recalled the events of that erotic night. He fondled the white gloves she wore at the end of the session that became soiled. Tyler left him have them as a remembrance as well as to have them cleaned and ready for their next time together. Suddenly, a message vibrated on his phone. It was from Tyler and included a photo taken by a camera hidden in the room while she tickled him. A message from her said
“Until next time, my dearest Glove Loving Tickle Slave!”
The End (for now)
