A new anonymous commission from DeviantArt
Jeremy: Tickle Toy of the Dom (F/M)
By MrObscura101
Jeremy double checked everything was ready as his heart began to race, the 18-year-old had been left home alone by his parents all weekend and that meant he could engage in his favourite pastime… self-bondage. He had always loved to tie himself up and over the years he had enjoyed playing the robber in cops and robbers, a willing assistant in a magic show, just any excuse to be bound, but now he finally had a chance to try out some new equipment he had bought
Stripping down to his boxer shorts he laid down on the bed and took some D-cuffs and secured them to his ankles and wrists, then attached the ankle cuffs to D-rings he had secured to the edge of the bed frame, then secured his left wrist the same way, before manoeuvring himself to bind his right wrist to the frame as well
“Ok, all secure… and the key will be out in an hour” he thought, looking over to the key he had frozen in a block of ice and left in a bowl on the nightstand that he could use to eventually free himself
Jeremy spent the next twenty minutes pulling and testing the bonds, trying his best to get free but finding himself truly stuck. He didn’t mind though, he was fully enjoying himself… until he heard a noise
“Jeremy?” a female voice called which he recognised of his neighbor Alice who was a couple of years older than him entering the house
“Alice?” he called in shock
“Your mom asked me to check in while they’re away, everything ok?” she heard him call
“Uh yeah everything’s good!” he called, now pulling desperately at the bonds to get free as he heard her walking up the stairs
“Cool, so my boyfriend… or rather ex-boyfriend cancelled our dinner plans last minute so I have a free evening, how about we get takeout for dinner? My treat?” she continued talking as she reached his room
“NO WAIT! DON’T COME IN!” he called as he saw the doorknob turn but it was too late
“What you got a girl in here…” she started to say… then her voice trailed off “oh…”
Jeremy went bright red as she looked him over
“Its…I…” he stuttered as she just stared before speaking softly
“It’s ok…” she said as she sat down by him, Jeremy had half expected her to scold him, but she seemed totally sincere
“It’s a normal thing to want to experience…” she continued, “You know what I do right? … you’re a smart kid”
Jeremy was aware that while officially she was an artist she was also a part time dominatrix, a fact his parents seemed oblivious to, he had occasionally seen her setting up the spare room in her house which he could partially see from his own room meaning he could occasionally see into it with her laying out various ropes and other items for a session before she closed the curtains, and once or twice had seen her dressed in her outfit of a corset and thigh high boots
“Uh thanks… look… could you help me?” he asked, wanting to get some clothes on at least, she looked over to the frozen key and picked up the bowl, then a grin appeared on her face
“Here you go… and she dropped it to the bed
“W…what are you doing?”
“Well…” she replied as she sat on the bed to his left “I think it’s a bit insulting that you didn’t ask for my help…” she continued before she lightly skittered her lacquered nails against his side, making him flinch “What can we do about that?”
Jeremy tried to stifle his laughter
“hhahhaa noooo waiihhtt…” he gasped
“You know I have all sorts of toys at home to tie up little boys like you…” she purred as she began moving up and down his sides before poking at his ribs, ignoring his giggles as if she didn’t realise it was tickling him
“Aiihhhllliiceee ppphllheeaseee!!!!!!” he wailed, now trying to fidget away but his movements were too restricted
“I have to say it’s not often I get someone who’s already tied themselves up… you should be careful you know… this old house is haunted by a tickle monster!” and with that she began tickling in earnest, unleashing her nails against his sides
“HAHAHHAHAHAHAHAAA OHOHOOHO GAHAHAHDDD NOOHOHOHOOO!!!!!!!” he wailed, his body leapt up as much as possible but was unable to get away
“Look at you trying to get away from the tickle monster!” Alice grinned as she then stopped for a few seconds “I think a naughty boy like you needs to be punished for getting himself all tied up like this”
Jeremy watched as she then pulled up top off exposing a black sheer bra before removing her knee-high boots and skirt showing off her sheer black panties and black socks
“Now then…” she said seductively as she climbed onto the bed and straddled his waist “Let’s see just how ticklish you are…”
“N…nohoho…waiitt ahh miinnhhuttee…” Jeremy tried to say, already giggling as her nails inched closer and closer but then they were skittering at his underarms
“HAHAHHAHAHAHAHA OOHOHOO NOHOHOHOOO PPHHLLEEASSSEEE!!!!!!” he wailed immediately
“Aw does it tickle? Tell mommy how bad it tickles”
“HHAHAHAHAHA IIHHTT TIICCKKLLEESSS SOOHSHOOO BAHAHHDDD!!!!!”
“That’s good!”
“GOOOOOHHHDDD???!!!!!”
“Oh yes the tickle monsters love finding ticklish wittle boys all trapped and helpless… some have been known to tickle their victims for hours!”
Jeremy tried to thrash about, pull his arms down or get Alice off of him but she easily pinned him down as she mocked his helplessness
“Aw look at you trying to get away!” she grinned “But all you can do is laugh… laugh for me!”
“HAHAHAHHAHAHHA AHHAALLIICEEEEE!!!!!” he cried
“Oh no not Alice, I’m the tickle monster, and I’ll only stop when I say you’ve had enough!”
Alice continued tickling Jeremy’s underarms for several minutes before stopping
“hahahahhaaa whahhaahhtt thheheee heheelll???!!!!” he snapped “ALICE GET ME OUTTA HERE!!!!!” he added, however then yelped as her index finger traced against his left underarm
“Sorry kid it’s not gonna be that easy…”
“DAMN IT YOURE JUST SUPPOSED TO BE WATCHING ME!”
“And I am, and with you all tied like this it means you can’t get into any trouble” she grinned
“WHY ARE YOU DOING THIS?!”
“Simple… its Saturday night and I just dumped my lousy ex, I’ve got no clients booked in tonight either so this is a great opportunity to get some practice in”
Jeremy looked at her
“IF YOU DON’T LET ME GO I’LL TELL MY FOLKS!”
“Go ahead…” she grinned as she held up her phone “But maybe I’ll take some pics first… I’m sure they’ll love to hear what you got up to when they were away” she added. Jeremy went pale at the very thought
“Or…” she said warmly “We could just have a bit of fun” she winked and Jeremy nodded, then yelped as she tickled his sides again making him burst out laughing
“Good boy”
“HAHHAHAHAHHAHAHA NOHOOHOHOOO!!!!!!”
“No? You don’t get to say no to a tickle monster! That just encourages us to tickle more!” she said wickedly as she continued digging into his ribs
“HAHHAHAHAA OOHHAKAKAHAH!!!! YAHAHAHHEEEESSS!!!!!!” he shouted
“If you insist!”
“THHAHAATSSS NOOHOHTT FAAHAHIIRRR!!!!!!” he yelped
“Too bad for you then…” she winked back
As Jeremy tried to think of a way out of this he then saw her notice a quill on his desk which he had bought on a visit to a colonial town
“Ohh look at this…” she said in delight as she grabbed it and moved it about like a dangerous weapon
“NO!!! ALICE DOOHOHOHOHOHOHOHOHOHOONNTTTT!!!!!!!” he began to beg until it causally brushed against his left nipple
“HAHHAHAHAHAHAHAHA DAHAHAAMMMNN IHHTHTHTTTT!!!!!!!!” Jeremy squealed as he fought like mad to get away from the feather as Alice began alternating between his left and right nipples
Alice continued this merciless teasing for several minutes before deciding he needed a break
“Feeling better?” she asked as she stopped tickling
“hahahahhahaaaa” he began to calm down from laughing
“Aw is it too much? I thought you were the man of the house not some kid”
“I AM!!!!!” he snapped, she knew that saying he was just a kid would get under his skin which was exactly what she wanted
When he had stopped laughing Alice climbed off him
“Ok kid, since I’m not totally heartless here’s the deal… if you can last two minutes without laughing I’ll let you go AND you will then get to tie me up and play with me…” she grinned “BUT if you fail… let’s just say things will get worse for you” Jeremy tried to think how things could be worse… but he knew he had to try and win this to get free, then he could pay her back!
“You’re on!” he said confidently, but grew worried when she sat herself by his feet…
“oh no…” he thought worriedly, as she set her watch to time two minutes and began tickling his left foot with her nails
“GHGHFFF!!!!!!” he gritted his teeth and tried his best not to laugh
“Aw look at you trying not to laugh… admirable, but a waste of energy” she grinned as she continued teasingly moving against his left foot. Jeremy manged to actually keep himself from laughing despite his ticklishness for about 45 seconds until Alice upped her game by tickling his right foot with her other hand
“GHHRHHRHFHFHHFFHFMM!!!!!!!!” Jeremy shrieked as he jolted around, adamant not to laugh but knew he was moments away from breaking
“COME ON!!!! JUST A MINUTE TO GO!!!!!!” he thought as he spied the wall clock ticking away, and knowing victory would mean getting to tickle Alice was certainly an incentive, but she could tell how he was moments away from breaking as she grabbed a hairbrush from her handbag and held it up wickedly before moving it closer…
“HHAAAHAAHHAHAHAHAHAHAHAHAHAHAAAA OOHOHHOOHOHO MAMAAHHYY GAAHAHHHDDD!!!!!!!!!!!!!!!!!!!!” Jeremy screamed as the bristles suddenly scrubbed up and down his left foot while without even pausing Alice’s nails continued at his right foot
“Uh-oh…” she smirked wickedly as she continued “Looks like someone’s in trouble…”
“HAHHAHAHAHAHAHAHAHAHA STAHAHAHHAHAPPPP!!!!!! PPPLLHEHEHAAASSSEEE!!!!!” he cried frantically
“Well…” she hummed “Since you asked so nicely…” and she stopped
Jeremy gasped as he tried to stop laughing
“hahhahahaa...iihhh…” he began to say
“Lost the bet, so my little tickle toy I guess things are gonna get worse for you!” she grinned deviously. Jeremy tried to work out what she meant by worse as she climbed onto the bed and sat between his spread legs
“You know, working in the job I do I have become very good at reading people…” and she took the waist of his boxers
“HEY!!!!!” he gasped as she pulled them down
“And I know you’re actually enjoying this!” she grinned
Jeremy went bright red as his manhood was now exposed
“A…Alice…” he gasped in shock
“No no… tickle monster” she corrected him as she held up the quill from before. Jeremy went pale as she moved it around
“NO!!!! ENOUGH NOW OK!!!! ITS ENOHOHOHOOHOHOHOHOOHOHOHOHOHOHUUGGHHH!!!!!!!!!!!!!!!!!” he began to shout, then lurched wildly as the feather lightly brushed against his shaft
“What was that?” she asked
“HAHHAHAHAHAHAHAHAHAHAHAHAAAAAA SSTAHAHAHAHAHAPPP!!!!!!!!”
“I warned you it would get worse” she shrugged as she continued
Jeremy was now trying everything in his power to escape this nightmare while Alice simply moved the feather against his rapidly hardening manhood
“Oh my look how hard you’ve gotten, too bad you didn’t win before, then you could be teasing me like this… guess that’s sucks for you”
“HAHAHHAHAHAHAAA QUUIIEEHEHHEHETTT!!!!!!!!” he cried in frustration and she then flicked the feather against his tip making him squeal
“No back-talk young man!” she ordered
Alice continued teasingly moving the feather against him as Jeremy howled with laughter and strained about, he never would have guessed he could be so ticklish here, but he was and Alice’s skills were simply unbearable and making him laugh and laugh so much until he was sure he might pass out
“Ah look at you straining about my little tickle toy!” she cooed as she finally lessened the tickling
“HAHHAAHAHHAA AHAHAHAHLLIICCHHEEE!!!!! MEERHHRCCYY!!!!!!!” he cried
“Mercy? I don’t think so, you lost the challenge and you’ll stay here until I say so… unless…”
“Yes?”
“You want to try double or nothing?”
“What do you mean?”
“We can play another game… if you win I’ll let you go?”
“What kind of game?”
“I’m not telling you” she grinned coyly
“SO HOW AM I SUPPOSED TO DECIDE?!”
“That’s the risk you take, you can either lay here and be tickled all night by me or try something that might earn you your freedom…”
Jeremy had no idea how to proceed now
“I need a hint!”
“Sorry dear, mistresses don’t give hints to tickle toys” she replied “Better choose quick…” and she swayed the feather about menacingly
“OK!!!!!” he cried in a panic
“Good, now firstly, pick a number between one and ten right now!”
“Uh… seven…” he blurted out, wondering what she needed that for
“Ok…” she smiled deviously
“Here’s the deal kid… it’s pretty obvious you are near climax…” he blushed at hearing this “So I’m gonna stroke you seven times, if you survive without cumming you win, if you fail you’re mine!”
“WHAT?!” THAT’S INSANE!!!!” he cried
“Self-control is a very important aspect to learn” she smiled as she then peeled off her socks and discarded them “One of my clients is currently at work and wearing a chastity cage on his manhood for that very reason” she then brought the feather back to him
“Ready?”
Before he could answer the feather moved against the length of his shaft once more
“Onnnnneeee” she said for emphasis
“AAARGRGRHHH!!!!!!” he groaned, shifting about
“Twwwwoooo…” she continued and again he shrieked, his member getting harder and harder
“Thrrrreeeee…”
After three strokes she then lifted her legs up
“W… what are you doiiiHHNGNGNGGGHHH!!!????” he asked as she moved her bare feet either side of his shaft
“Don’t act innocent, I saw how your eyes immediately looked to my feet the second I took my socks off…, plus I’ve seen you sneak looks at them before. Most guys would look at my chest… but the foot guys…well I can always tell who they are…” she smiled. Jeremy didn’t know what to say… it was true he liked looking at women’s feet and hers were flawless, he always made sure to sneak a look if she was barefoot or in sandals… which was now coming to bite him in the ass!
“oohohhh…” he moaned as her soft soles pressed against his member
“Like them? I had a pedicure earlier today so they’re super soft…” she asked as she moved them up and down his shaft
“Foooouuurrr….” she then added
“URURUUGUGGHGHHH!!!!!!!” he grunted back, unable to speak now as he focused on the sensation of her silky smooth soles against his throbbing member, it was the most amazing feeling he had ever experienced
Jeremy had given up protesting now, in fact he had barely spoken as Alice continued for the fifth and sixth strokes, a part of his mind had been thinking to try and ignore the sensations so that he might win the challenge… and hopefully be allowed to play with her feet but it was so difficult to ignore her flawless soles, even bound like this he felt lucky to be in this position
“Well… one more to go…” she grinned as she pulled her feet away and repositioned herself once more, lowering her body down between his legs
“Let’s see if you can hold out one more time…”
“Wai...HAHAHAHAHAHAHAHTT!!!!!!” he tried to say… then her lips enveloped his cock
“OOHOHOHOHOOH MAHAHAHAHAYYY GAHAHAHHDDD!!!!!!!” he shrieked as she slowly moved her lips up and down his shaft, he could also feel her tongue gently probing at the tip as well
“AAHHLLICCEE!!!!! IIHHHMM GOOHHANANAAA… AAHRHRHHRHGHHHGHH!!!!!!!!” he tried to say, but finally he came, his body shuddered as he did so, exhausted arms and legs pulling at the restraints as he achieved the biggest orgasm of his life
Once he was finished, he lay there completely spent, then noticed Alice was still sucking away
“iiihhmm…” he tried to say but was so drained he simply blacked out…
Jeremy slowly awoke and gasped to see Alice there decked out in her dominatrix outfit of a latex corset, panties and black thigh high boots as she gently teased his nipples
“Wakey wakey…” she cooed and he realised he wasn’t in his room, instead it was some kind of dungeon set up, tied down to an x-frame totally naked with a huge ball gag in his mouth
“ggmhmff…” he groaned in confusion before realising they weren’t alone
“Bout time!” a voice said
“Yes times a wasting!” another voice added
“GHGMMFFH??!!” he cried upon realising two other women dressed similarly to Alice were also there
“Jeremy, these are my friends Mistress Ebony…” she gestured to a young African-American woman “And Mistress Thorn” and she pointed to an Asian woman, “Since you failed the challenge I decided that you’re going to spend all weekend with me… and them” all three then grinned at him
“GHFMFMFMFH???!!!!!” he cried
“Oh don’t worry I told your parents you were feeling lonely so you’ll be staying with me while they’re away”
Jeremy watched as the three began to take up positions around him as Alice held something up
“Look what I got for you!” it was a leather collar with TICKLE SLAVE on it
“NFFHFHFH!!!!!!!” he shook his head as is was placed around his neck, then from behind Mistress Ebony blindfolded him
“He’s a cutie!”
“Oh yes, its so much fun tickling little immature boys like this to insanity!” Mistress Thorn added
“Now my friends couldn’t believe how ticklish you were so I thought we could give them a demonstration first”
“GHGFMMFMFFHHH!!!!!!!!” he shook his head frantically
“And if you’re a good boy… maaaaybe you’ll get to have some fun with our feet after” she added. Before he could say anything, they then descended upon him tickling his underarms, stomach and feet between them with their sharp nails and a selection of feathers
“HMFMFFHFMFMFFHFMFMFFHH!!!!!!!!” he screamed, then yelped as a feather grazed against his member
“Look how hard he’s already gone!”
“This will be so much fun!” they chuckled between themselves. Jeremy fought and pleaded for mercy… but he was now the plaything of the Doms
The End?
Jeremy: Tickle Toy of the Dom (F/M)
By MrObscura101
Jeremy double checked everything was ready as his heart began to race, the 18-year-old had been left home alone by his parents all weekend and that meant he could engage in his favourite pastime… self-bondage. He had always loved to tie himself up and over the years he had enjoyed playing the robber in cops and robbers, a willing assistant in a magic show, just any excuse to be bound, but now he finally had a chance to try out some new equipment he had bought
Stripping down to his boxer shorts he laid down on the bed and took some D-cuffs and secured them to his ankles and wrists, then attached the ankle cuffs to D-rings he had secured to the edge of the bed frame, then secured his left wrist the same way, before manoeuvring himself to bind his right wrist to the frame as well
“Ok, all secure… and the key will be out in an hour” he thought, looking over to the key he had frozen in a block of ice and left in a bowl on the nightstand that he could use to eventually free himself
Jeremy spent the next twenty minutes pulling and testing the bonds, trying his best to get free but finding himself truly stuck. He didn’t mind though, he was fully enjoying himself… until he heard a noise
“Jeremy?” a female voice called which he recognised of his neighbor Alice who was a couple of years older than him entering the house
“Alice?” he called in shock
“Your mom asked me to check in while they’re away, everything ok?” she heard him call
“Uh yeah everything’s good!” he called, now pulling desperately at the bonds to get free as he heard her walking up the stairs
“Cool, so my boyfriend… or rather ex-boyfriend cancelled our dinner plans last minute so I have a free evening, how about we get takeout for dinner? My treat?” she continued talking as she reached his room
“NO WAIT! DON’T COME IN!” he called as he saw the doorknob turn but it was too late
“What you got a girl in here…” she started to say… then her voice trailed off “oh…”
Jeremy went bright red as she looked him over
“Its…I…” he stuttered as she just stared before speaking softly
“It’s ok…” she said as she sat down by him, Jeremy had half expected her to scold him, but she seemed totally sincere
“It’s a normal thing to want to experience…” she continued, “You know what I do right? … you’re a smart kid”
Jeremy was aware that while officially she was an artist she was also a part time dominatrix, a fact his parents seemed oblivious to, he had occasionally seen her setting up the spare room in her house which he could partially see from his own room meaning he could occasionally see into it with her laying out various ropes and other items for a session before she closed the curtains, and once or twice had seen her dressed in her outfit of a corset and thigh high boots
“Uh thanks… look… could you help me?” he asked, wanting to get some clothes on at least, she looked over to the frozen key and picked up the bowl, then a grin appeared on her face
“Here you go… and she dropped it to the bed
“W…what are you doing?”
“Well…” she replied as she sat on the bed to his left “I think it’s a bit insulting that you didn’t ask for my help…” she continued before she lightly skittered her lacquered nails against his side, making him flinch “What can we do about that?”
Jeremy tried to stifle his laughter
“hhahhaa noooo waiihhtt…” he gasped
“You know I have all sorts of toys at home to tie up little boys like you…” she purred as she began moving up and down his sides before poking at his ribs, ignoring his giggles as if she didn’t realise it was tickling him
“Aiihhhllliiceee ppphllheeaseee!!!!!!” he wailed, now trying to fidget away but his movements were too restricted
“I have to say it’s not often I get someone who’s already tied themselves up… you should be careful you know… this old house is haunted by a tickle monster!” and with that she began tickling in earnest, unleashing her nails against his sides
“HAHAHHAHAHAHAHAAA OHOHOOHO GAHAHAHDDD NOOHOHOHOOO!!!!!!!” he wailed, his body leapt up as much as possible but was unable to get away
“Look at you trying to get away from the tickle monster!” Alice grinned as she then stopped for a few seconds “I think a naughty boy like you needs to be punished for getting himself all tied up like this”
Jeremy watched as she then pulled up top off exposing a black sheer bra before removing her knee-high boots and skirt showing off her sheer black panties and black socks
“Now then…” she said seductively as she climbed onto the bed and straddled his waist “Let’s see just how ticklish you are…”
“N…nohoho…waiitt ahh miinnhhuttee…” Jeremy tried to say, already giggling as her nails inched closer and closer but then they were skittering at his underarms
“HAHAHHAHAHAHAHA OOHOHOO NOHOHOHOOO PPHHLLEEASSSEEE!!!!!!” he wailed immediately
“Aw does it tickle? Tell mommy how bad it tickles”
“HHAHAHAHAHA IIHHTT TIICCKKLLEESSS SOOHSHOOO BAHAHHDDD!!!!!”
“That’s good!”
“GOOOOOHHHDDD???!!!!!”
“Oh yes the tickle monsters love finding ticklish wittle boys all trapped and helpless… some have been known to tickle their victims for hours!”
Jeremy tried to thrash about, pull his arms down or get Alice off of him but she easily pinned him down as she mocked his helplessness
“Aw look at you trying to get away!” she grinned “But all you can do is laugh… laugh for me!”
“HAHAHAHHAHAHHA AHHAALLIICEEEEE!!!!!” he cried
“Oh no not Alice, I’m the tickle monster, and I’ll only stop when I say you’ve had enough!”
Alice continued tickling Jeremy’s underarms for several minutes before stopping
“hahahahhaaa whahhaahhtt thheheee heheelll???!!!!” he snapped “ALICE GET ME OUTTA HERE!!!!!” he added, however then yelped as her index finger traced against his left underarm
“Sorry kid it’s not gonna be that easy…”
“DAMN IT YOURE JUST SUPPOSED TO BE WATCHING ME!”
“And I am, and with you all tied like this it means you can’t get into any trouble” she grinned
“WHY ARE YOU DOING THIS?!”
“Simple… its Saturday night and I just dumped my lousy ex, I’ve got no clients booked in tonight either so this is a great opportunity to get some practice in”
Jeremy looked at her
“IF YOU DON’T LET ME GO I’LL TELL MY FOLKS!”
“Go ahead…” she grinned as she held up her phone “But maybe I’ll take some pics first… I’m sure they’ll love to hear what you got up to when they were away” she added. Jeremy went pale at the very thought
“Or…” she said warmly “We could just have a bit of fun” she winked and Jeremy nodded, then yelped as she tickled his sides again making him burst out laughing
“Good boy”
“HAHHAHAHAHHAHAHA NOHOOHOHOOO!!!!!!”
“No? You don’t get to say no to a tickle monster! That just encourages us to tickle more!” she said wickedly as she continued digging into his ribs
“HAHHAHAHAA OOHHAKAKAHAH!!!! YAHAHAHHEEEESSS!!!!!!” he shouted
“If you insist!”
“THHAHAATSSS NOOHOHTT FAAHAHIIRRR!!!!!!” he yelped
“Too bad for you then…” she winked back
As Jeremy tried to think of a way out of this he then saw her notice a quill on his desk which he had bought on a visit to a colonial town
“Ohh look at this…” she said in delight as she grabbed it and moved it about like a dangerous weapon
“NO!!! ALICE DOOHOHOHOHOHOHOHOHOHOONNTTTT!!!!!!!” he began to beg until it causally brushed against his left nipple
“HAHHAHAHAHAHAHAHA DAHAHAAMMMNN IHHTHTHTTTT!!!!!!!!” Jeremy squealed as he fought like mad to get away from the feather as Alice began alternating between his left and right nipples
Alice continued this merciless teasing for several minutes before deciding he needed a break
“Feeling better?” she asked as she stopped tickling
“hahahahhahaaaa” he began to calm down from laughing
“Aw is it too much? I thought you were the man of the house not some kid”
“I AM!!!!!” he snapped, she knew that saying he was just a kid would get under his skin which was exactly what she wanted
When he had stopped laughing Alice climbed off him
“Ok kid, since I’m not totally heartless here’s the deal… if you can last two minutes without laughing I’ll let you go AND you will then get to tie me up and play with me…” she grinned “BUT if you fail… let’s just say things will get worse for you” Jeremy tried to think how things could be worse… but he knew he had to try and win this to get free, then he could pay her back!
“You’re on!” he said confidently, but grew worried when she sat herself by his feet…
“oh no…” he thought worriedly, as she set her watch to time two minutes and began tickling his left foot with her nails
“GHGHFFF!!!!!!” he gritted his teeth and tried his best not to laugh
“Aw look at you trying not to laugh… admirable, but a waste of energy” she grinned as she continued teasingly moving against his left foot. Jeremy manged to actually keep himself from laughing despite his ticklishness for about 45 seconds until Alice upped her game by tickling his right foot with her other hand
“GHHRHHRHFHFHHFFHFMM!!!!!!!!” Jeremy shrieked as he jolted around, adamant not to laugh but knew he was moments away from breaking
“COME ON!!!! JUST A MINUTE TO GO!!!!!!” he thought as he spied the wall clock ticking away, and knowing victory would mean getting to tickle Alice was certainly an incentive, but she could tell how he was moments away from breaking as she grabbed a hairbrush from her handbag and held it up wickedly before moving it closer…
“HHAAAHAAHHAHAHAHAHAHAHAHAHAHAAAA OOHOHHOOHOHO MAMAAHHYY GAAHAHHHDDD!!!!!!!!!!!!!!!!!!!!” Jeremy screamed as the bristles suddenly scrubbed up and down his left foot while without even pausing Alice’s nails continued at his right foot
“Uh-oh…” she smirked wickedly as she continued “Looks like someone’s in trouble…”
“HAHHAHAHAHAHAHAHAHAHA STAHAHAHHAHAPPPP!!!!!! PPPLLHEHEHAAASSSEEE!!!!!” he cried frantically
“Well…” she hummed “Since you asked so nicely…” and she stopped
Jeremy gasped as he tried to stop laughing
“hahhahahaa...iihhh…” he began to say
“Lost the bet, so my little tickle toy I guess things are gonna get worse for you!” she grinned deviously. Jeremy tried to work out what she meant by worse as she climbed onto the bed and sat between his spread legs
“You know, working in the job I do I have become very good at reading people…” and she took the waist of his boxers
“HEY!!!!!” he gasped as she pulled them down
“And I know you’re actually enjoying this!” she grinned
Jeremy went bright red as his manhood was now exposed
“A…Alice…” he gasped in shock
“No no… tickle monster” she corrected him as she held up the quill from before. Jeremy went pale as she moved it around
“NO!!!! ENOUGH NOW OK!!!! ITS ENOHOHOHOOHOHOHOHOOHOHOHOHOHOHUUGGHHH!!!!!!!!!!!!!!!!!” he began to shout, then lurched wildly as the feather lightly brushed against his shaft
“What was that?” she asked
“HAHHAHAHAHAHAHAHAHAHAHAHAAAAAA SSTAHAHAHAHAHAPPP!!!!!!!!”
“I warned you it would get worse” she shrugged as she continued
Jeremy was now trying everything in his power to escape this nightmare while Alice simply moved the feather against his rapidly hardening manhood
“Oh my look how hard you’ve gotten, too bad you didn’t win before, then you could be teasing me like this… guess that’s sucks for you”
“HAHAHHAHAHAHAAA QUUIIEEHEHHEHETTT!!!!!!!!” he cried in frustration and she then flicked the feather against his tip making him squeal
“No back-talk young man!” she ordered
Alice continued teasingly moving the feather against him as Jeremy howled with laughter and strained about, he never would have guessed he could be so ticklish here, but he was and Alice’s skills were simply unbearable and making him laugh and laugh so much until he was sure he might pass out
“Ah look at you straining about my little tickle toy!” she cooed as she finally lessened the tickling
“HAHHAAHAHHAA AHAHAHAHLLIICCHHEEE!!!!! MEERHHRCCYY!!!!!!!” he cried
“Mercy? I don’t think so, you lost the challenge and you’ll stay here until I say so… unless…”
“Yes?”
“You want to try double or nothing?”
“What do you mean?”
“We can play another game… if you win I’ll let you go?”
“What kind of game?”
“I’m not telling you” she grinned coyly
“SO HOW AM I SUPPOSED TO DECIDE?!”
“That’s the risk you take, you can either lay here and be tickled all night by me or try something that might earn you your freedom…”
Jeremy had no idea how to proceed now
“I need a hint!”
“Sorry dear, mistresses don’t give hints to tickle toys” she replied “Better choose quick…” and she swayed the feather about menacingly
“OK!!!!!” he cried in a panic
“Good, now firstly, pick a number between one and ten right now!”
“Uh… seven…” he blurted out, wondering what she needed that for
“Ok…” she smiled deviously
“Here’s the deal kid… it’s pretty obvious you are near climax…” he blushed at hearing this “So I’m gonna stroke you seven times, if you survive without cumming you win, if you fail you’re mine!”
“WHAT?!” THAT’S INSANE!!!!” he cried
“Self-control is a very important aspect to learn” she smiled as she then peeled off her socks and discarded them “One of my clients is currently at work and wearing a chastity cage on his manhood for that very reason” she then brought the feather back to him
“Ready?”
Before he could answer the feather moved against the length of his shaft once more
“Onnnnneeee” she said for emphasis
“AAARGRGRHHH!!!!!!” he groaned, shifting about
“Twwwwoooo…” she continued and again he shrieked, his member getting harder and harder
“Thrrrreeeee…”
After three strokes she then lifted her legs up
“W… what are you doiiiHHNGNGNGGGHHH!!!????” he asked as she moved her bare feet either side of his shaft
“Don’t act innocent, I saw how your eyes immediately looked to my feet the second I took my socks off…, plus I’ve seen you sneak looks at them before. Most guys would look at my chest… but the foot guys…well I can always tell who they are…” she smiled. Jeremy didn’t know what to say… it was true he liked looking at women’s feet and hers were flawless, he always made sure to sneak a look if she was barefoot or in sandals… which was now coming to bite him in the ass!
“oohohhh…” he moaned as her soft soles pressed against his member
“Like them? I had a pedicure earlier today so they’re super soft…” she asked as she moved them up and down his shaft
“Foooouuurrr….” she then added
“URURUUGUGGHGHHH!!!!!!!” he grunted back, unable to speak now as he focused on the sensation of her silky smooth soles against his throbbing member, it was the most amazing feeling he had ever experienced
Jeremy had given up protesting now, in fact he had barely spoken as Alice continued for the fifth and sixth strokes, a part of his mind had been thinking to try and ignore the sensations so that he might win the challenge… and hopefully be allowed to play with her feet but it was so difficult to ignore her flawless soles, even bound like this he felt lucky to be in this position
“Well… one more to go…” she grinned as she pulled her feet away and repositioned herself once more, lowering her body down between his legs
“Let’s see if you can hold out one more time…”
“Wai...HAHAHAHAHAHAHAHTT!!!!!!” he tried to say… then her lips enveloped his cock
“OOHOHOHOHOOH MAHAHAHAHAYYY GAHAHAHHDDD!!!!!!!” he shrieked as she slowly moved her lips up and down his shaft, he could also feel her tongue gently probing at the tip as well
“AAHHLLICCEE!!!!! IIHHHMM GOOHHANANAAA… AAHRHRHHRHGHHHGHH!!!!!!!!” he tried to say, but finally he came, his body shuddered as he did so, exhausted arms and legs pulling at the restraints as he achieved the biggest orgasm of his life
Once he was finished, he lay there completely spent, then noticed Alice was still sucking away
“iiihhmm…” he tried to say but was so drained he simply blacked out…
Jeremy slowly awoke and gasped to see Alice there decked out in her dominatrix outfit of a latex corset, panties and black thigh high boots as she gently teased his nipples
“Wakey wakey…” she cooed and he realised he wasn’t in his room, instead it was some kind of dungeon set up, tied down to an x-frame totally naked with a huge ball gag in his mouth
“ggmhmff…” he groaned in confusion before realising they weren’t alone
“Bout time!” a voice said
“Yes times a wasting!” another voice added
“GHGMMFFH??!!” he cried upon realising two other women dressed similarly to Alice were also there
“Jeremy, these are my friends Mistress Ebony…” she gestured to a young African-American woman “And Mistress Thorn” and she pointed to an Asian woman, “Since you failed the challenge I decided that you’re going to spend all weekend with me… and them” all three then grinned at him
“GHFMFMFMFH???!!!!!” he cried
“Oh don’t worry I told your parents you were feeling lonely so you’ll be staying with me while they’re away”
Jeremy watched as the three began to take up positions around him as Alice held something up
“Look what I got for you!” it was a leather collar with TICKLE SLAVE on it
“NFFHFHFH!!!!!!!” he shook his head as is was placed around his neck, then from behind Mistress Ebony blindfolded him
“He’s a cutie!”
“Oh yes, its so much fun tickling little immature boys like this to insanity!” Mistress Thorn added
“Now my friends couldn’t believe how ticklish you were so I thought we could give them a demonstration first”
“GHGFMMFMFFHHH!!!!!!!!” he shook his head frantically
“And if you’re a good boy… maaaaybe you’ll get to have some fun with our feet after” she added. Before he could say anything, they then descended upon him tickling his underarms, stomach and feet between them with their sharp nails and a selection of feathers
“HMFMFFHFMFMFFHFMFMFFHH!!!!!!!!” he screamed, then yelped as a feather grazed against his member
“Look how hard he’s already gone!”
“This will be so much fun!” they chuckled between themselves. Jeremy fought and pleaded for mercy… but he was now the plaything of the Doms
The End?
I envy Jeremy. 
