Sherbet Riley
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Long time lurker, first time poster. I've been writing tickle fiction for many years but never had the guts to post anything until now. I figure life's too short, might as well share it with folks who may get something out of it instead of locking it away in some vault. I actually settled on this pen name last minute and figured I'd make a new account to post stories under said moniker.
This is one of the first stories I ever wrote and it's quite long so I figured I'd post it in chunks as opposed to one go. That way, if it's terrible I won't embarrass myself as badly, and if it's good I can milk the suspense. Win win. This first part is mostly set-up but the end felt like a logical place to stop for now as, again, it's quite long. Either way, I hope you enjoy.
Under Her Palm
Teddy needed a cigarette. He’d been craving one for days now but had been able to valiantly offset his cravings by keeping himself occupied. A cigarette would be his reward; he told himself, after he’d applied to enough jobs and unpacked enough boxes to justify the indulgence. The trick was to not have any lying around. Inevitably, by the time he’d accomplished enough to earn his nicotine fix he’d be too tired to bother with a trip to the store. But now he was halfway through his third beer and the smell of smoke was radiating off every new arrival at the bar. It was only a matter of time before he wandered outside to ask one of the barflies for a cigarette. He had a spare dollar if it came to that.
It had been nearly a decade since he’d visited The Shoehorn, in fact it had been his go-to bar as a teenager. After acquiring a fake ID just after he turned 17, Teddy would visit any chance he could. The bartenders might look at him askance, but if they ever doubted the authenticity of his ID they’d never said anything. The trick, he would tell his friends, was to tip generously. Teddy smiled at the memory. He’d felt like such a grown up back then, nursing Tecates and making small-talk with strangers.
But he felt far from an adult now. Just last month his living situation in the city had deteriorated to the point where he had no choice but to move back home with his parents. He had been one of the few people to actually make it out of this town and Teddy had sworn he would never return - outside of family events and holidays, of course. His parents had been incredibly supportive and understanding. In truth, it had been nice spending time with them those first few weeks. But being back in his childhood bedroom and sleeping on his old twin bed had gotten old fast. Now it thoroughly depressed him.
Of course, this was temporary – that’s what he kept insisting to himself and anyone who bothered to ask, anyway. But two months had gone by and the longer things went on, the more boxes he unpacked, the less and less temporary the situation felt. Teddy had been lucky enough to find work here and there, but at the rate he was going it would be nearly a year before he could to afford to move back to the city, just shy of his 27th birthday.
Shit, he really needed a cigarette.
“Screw it”, Teddy thought to himself, downing what remained of his now lukewarm beer. “If there was ever a time to treat myself it may as well be now.”
Teddy hugged his jacket close to his body as he stepped outside. It had become decidedly chillier since he’d arrived. He was drunker than he thought and was still struggling with the buttons of his jacket when a familiar sound stopped him cold.
Heheheheheheheh *snort* hehehehehehhehehehe….
Teddy’s mouth went dry. It couldn’t be….
But there was no mistaking her. Curvaceous and short, with full cheeks well framed by dark brown curls, there she was, his old babysitter: Amy Ruth Baker. It may have been nearly fifteen years since they’d last seen each other, but Teddy recognized her instantly.
Amy was tucked away in the corner near the window, lighting the cigarette of a tall, athletic woman with a bright blonde ponytail – the one who had made her laugh. Amy was appropriately dressed, warm and comfortable under a thick, wool sweater that hugged her prodigious bosom while complimenting her dark jeans and red converse shoes. She must have been around 40 years old now. From what Teddy could tell, Amy had gained some weight, but so had he since he’d been home. Amy had been very athletic in her younger years, sturdy. She was often tasked with playing goalie or among the first to be selected for the wrestling team. He remembered that she had always been very strong.
But of course, that’s not all he remembered.
No, what Teddy remembered best was Aunty Amy, the Tickle Monster. He had always been reasonably well behaved as a boy. In fact, he had an almost pathological fear of getting in trouble. It was so pronounced that he’d even get a pit in his stomach whenever he watched teens sneaking out of the house or otherwise break the rules on TV. But as polite and well behaved as he was for his age, Teddy was still prone to the occasional outburst or tantrum. He may have refused to brush his teeth or fibbed about finishing his homework, and when he did Amy knew exactly how to handle him.
On one of their first nights together Amy had discovered Teddy’s weakness: he was unbearably ticklish. All it took was a crooked finger under his arm or a poke to the belly and he’d melt into a puddle of giggles on the floor. He still remembered the first time Amy tickled him. Really tickled him. It was so clear to him, even now. He remembered the scratchy feeling of the carpet rubbing against his cheek as Amy pinned him facedown on the floor, her butt pressed into his back as she pulled his ankles toward her and tickled the socks off his feet. He recalled the way she hooked her finger under the elastic lip of his sock and inched it up and down his foot, testing for tickle spots as he giggled and wriggled under her weight. He remembered her own socked feet, greying and pilly, resting inches from his face as she teased him mad, slowly breaking down what little resistance he had against her delicate touch.
“Uhhh oooohhhhh, does my tickawy Teddy have sensitive widdle paws?” she cooed, drawing little circles on his heel with her index finger as he’d giggled helplessly into the carpet. “You know what happens to baby bears when they lie to Auntie Amy, don’t you? Don’t you?”
He knew very well. In fact, nine times out of ten Teddy had intentionally provoked Amy into tickling him. He hadn’t been able to put his finger on it at the time, but there was something exhilarating about the time he spent squealing under her nimble fingers. Growing up he’d always enjoyed being tickled, or at the very least didn’t detest it the way some of his friends did. But when Amy tickled him it was different somehow. Maybe it was the fact that she clearly enjoyed it too, laughing nearly as much as he did sometimes. He had a vivid memory of looking up at her through teary eyes to find her smiling down at him, giggling along with him as she played “accordion” with his ribs until he was hoarse from laughter.
Then time passed as it always does. Teddy grew up. One day he was too old for a babysitter, and certainly too old for the Tickle Monster. But as puberty kicked in and he grew into an adult, Teddy found that tickling had taken on new significance for him. It did not take long for him to realize that nearly every fantasy he had revolved around tickling or being tickled. By the time he was 20 Teddy learned to accept the truth: he had a potent tickle fetish. He spent many a night on tickling forums, reading stories, watching videos, and sharing formative anecdotes with likeminded individuals online. He’d mentioned Amy there more than once, and as time passed she became more and more central to some of his most vivid fantasies. He often found himself alone at night, touching himself at the thought of being under her control once more, her cooing teases softly into his ear as she tickled him hysteric.
And now there she was, standing outside the Shoehorn, lighting someone’s cigarette. By the time Teddy realized he was staring it was too late.
“Teddy? Teddy is that you?”
Amy was looking right at him now, smiling in recognition. She didn’t have to ask. She knew it was him. Teddy felt his ears getting hot as he waved at her awkwardly.
“Hey Amy. Good to see you.”
“What are you doing back in town?”
“Oh, I’m just vi-“
Amy put her hand up to her ear and leaned forward a bit.
“What’s that? I can’t hear you. Come on over. Don’t be shy! Be a good boy and say hello.”
Something about the way she said that last bit made his pants feel tight. Nevertheless, he stuffed his hands in his jacket pockets and shuffled over to Amy and her friend. Amy put her hand on her companion’s back and gestured toward Teddy.
“Moira, this is Teddy. I used to babysit him back in the day. Teddy, this is Moira. She’s an old friend.”
Moira held her cigarette between her lips as she stuck out her hand to shake.
“Pleasure to meet you, Teddy.”
“Likewise.”
Amy kept shifting her weight from foot to foot, rubbing her hands together to keep warm. Her cheeks were pink and her eyes ever so slightly unfocused. She was a little drunk. This felt somewhat scandalous to Teddy, who had only ever seen her drink Powerades and Diet Cokes in the time he’d known her.
“What are you doing in town, buddy? I thought you’d moved away.”
“Oh, just visiting. Figured I’d say hi to the folks, help them out a bit.”
“Help them out? They’re not…” Amy seemed genuinely concerned.
“Oh! No, no. They’re fine. Just, uh…being a good son, I guess.”
Amy smiled and put her hand on his shoulder. Teddy could feel his heart beating faster as she turned toward Moira.
“I bet you are. Moira, I swear, of all the kids I babysat Teddy here was probably the best-behaved little boy of the bunch. He was always so polite and quiet, well, except for…” She let it hang there a moment, giving Teddy a knowing look. “…well, lets just say I had to put his foot down now and then. Sorry, my foot.”
Realizing her slip of the tongue, Amy giggled to herself.
Hehehehehehehehehe *snort*
Teddy could really feel the weight of her hand on his shoulder now. Why was he suddenly so warm? Goddamn he needed a cigarette.
“Excuse me, Moira, but could I bum one of those?”
Moira wordlessly handed him a cigarette. Amy gasped.
“Teddy! Since when do you smoke?”
“Since college. I don’t know…”
“I don’t know if you remember, but when you were little you promised me you’d never, ever smoke.”
Teddy shrugged and smiled at the memory. He had promised her that, hadn’t he? Then again, he’d promised a lot of things while pinned beneath his chesty babysitter.
“Yeah, well…things change.”
“Do they?”
Amy was looking right at him now, a slight curl to her lips and a mischievous glint in her eye as she challenged him. He recognized that look. Both anxiety and excitement began comingling in his gut. A black car pulled up to the curb and Moira crushed what remained of her cigarette beneath her boot.
“Shit, that’s my car. I gotta run.”
She shook Teddy’s hand and hugged Amy goodbye, promising that they’d see each other again soon. Then she got in her Uber and took off into the night. Teddy and Amy lingered outside a while. She teased him a bit at first for smoking but soon found herself taking a drag of her own once he offered. Eventually the cold got the better of them and the two decided to move things back inside.
At the bar the two finally caught up in earnest. Teddy told Amy all about his time in college and the jobs he’d worked after graduating, the friends he’d made and parties he’d attended, always taking care to obscure the details of his present circumstances. Through their conversation, Teddy learned that Amy had gotten an MA in psychology but had found some difficulty getting her footing in the field once she’d earned her degree. She still lived in town, not all that far from the Shoehorn actually, and had secured some part time work as a hostess at a local Mexican restaurant. Teddy couldn’t be sure, but after a couple of drinks it felt like their banter had taken a warmer, slightly flirtatious tone. But surely that was all in his head.
“So how do you know…?” He was searching for her name. He was drunker than he thought.
“Moira.”
“Yes, Moira! How do you two know each other?”
Amy smiled and took a sip of her Blue Moon.
“We met in college, actually. She was a poli-sci major with a wicked sense of humor, which is why I think we got along so well. She had a little…side hustle that I helped her out with from time to time. Still do, actually. Mostly I just drive her places, check in, stuff like that. Help out sometimes, if she asks”
Teddy nodded, playing with the little red straw sticking out of his now room-temp whiskey sour. “Am I allowed to ask what the side hust-“
“She’s a dominatrix.” Amy said bluntly, watching Teddy’s face for any trace of a reaction. She noticed him swallow and raise his eyebrow ever so slightly. “I drive her to the clients houses and stay nearby in case anything happens. Nothing ever does, mind you, but I think she feels safer knowing I’m there.”
Teddy couldn’t believe this. As far as he was aware he’d never met a dominatrix before. So many of his fantasies – all of his fantasies, really – revolved around being dominated by women and tickled into submission. He briefly thought of Moira, and what it might be like to be at her mercy. He imagined her effortlessly pinning his hands above his head with one hand while counting his ribs with the other. His pants were growing tight again.
“Oh wow. And you, uh, you said you ‘help’ from time to time? What does that mean?”
Amy set down her drink and cleared her throat, not making eye contact with Teddy.
“Well, one day she had a client with a certain…preference. Apparently he’d glimpsed me when I was dropping Moira off and I guess I fit a “type” that was agreeable to his fantasy. He asked her to see if I’d be interested in assisting her in the session and I agreed. One thing led to another and…well, I actually had a lot of fun. So now whenever the clients request it, I help Moira out in…certain situations.”
“You said you fit a type. What type is that?”
Amy shrugged.
“Maternal, I suppose. I remind some men of their moms or aunties or…babysitters.”
Teddy swallowed.
“Can I ask what the clients usually want you to –“
“I tickle them.” She was looking Teddy straight in the eye now, her tone warm but firm, assured. Teddy’s mouth went dry. There was no way this was real. He could feel blood rushing to his cheeks, among other places, and was keenly aware of his heart beating faster in his chest. Noticing his reaction, Amy drew inward a little bit, embarrassed. “Oh honey, I didn’t mean to fluster you. I’m sorry. We don’t have to talk about this.”
“No!” It came out more forcefully than he’d intended. Amy tickling people was all Teddy wanted to talk about. He registered Amy’s surprise to his reaction and tried to quickly backpedal from his outburst. “I mean, uh, I – sorry. Just, that’s interesting is all. What do you mean you…’tickle’ them?”
Amy watched him for a moment, her eyes searching for something in his face. She’d been caught off guard by just how easy it had been to talk to Teddy now that he was an adult. They had been friendly when he was younger, sure, but she’d always remained professional. They mostly talked about school, cartoons, family, that sort of thing. She’d never expected that she’d one day be talking to him about anything even remotely sexual. Amy would never admit it, but she cared what Teddy thought of her. She wanted him to see her the way he had when she last babysat him, as someone who had their shit together. An adult.
But when she told him about her work with Moira, there had been no judgment, no disillusionment. Sadly, this had not always been the case when she opened up to people about it. But this went beyond mere curiosity, there was a hunger to Teddy now that she hadn’t noticed earlier. Once the conversation turned to tickling and his interest peaked, something clicked for Amy. Maybe it was the alcohol, maybe it was nostalgia, but at that moment all Amy wanted to do was tickle Teddy silly. And she knew he wanted that too. She smiled hungrily at him and decided to move in for the kill.
“I think you know exactly what I mean.” Amy purred as she leaned forward, resting her warm palm on Teddy’s knee. “Turns out some people are willing to pay pretty good money for some tickle time with Aunty Amy.” She gave his knee a little squeeze. It tickled. Teddy pulled away instinctively. Amy raised an eyebrow. “Something wrong, buddy?”
Holy shit, this was happening. Teddy cleared his throat and pressed his knees together, hoping he could hide his excitement.
“N-no. Nothing. Just…surprised me is all.”
“Oh yeah? Are you sure it isn’t something else?”
“Like-like what?”
Amy gave a little pout, like she’d just spotted a cute stray puppy in need of a good home. “You know what.” She beckoned him now, curling her index finger to bring him closer. “Come here…”
Teddy leaned in. Amy did the same. She placed one hand on the back of his neck and brought him in close. He could feel her warm breath tickle his ear and send goose bumps down his back as her voice dropped into a husky, maternal register. “Are you still my tickly widdle teddy bear?”
Amy’s hand was back on his knee, now drawing tickly little circles. Just a tease, light enough to titillate without evoking a laugh. It was getting harder to hide his erection, which was now straining forcefully against the zipper of his jeans. He could taste the bitter adrenaline creeping up the back of his tongue.
Barely able to believe it, Teddy could only eke out the most bashful whisper in response, “…yes.”
“Good boy,” Amy breathed. She pulled back and looked at him with a dreamy smile, her finger still lazily drawing circles on his knee, which was now bouncing ever so slightly from excitement. “Now ask me.”
Teddy was confused, his mind clouded by arousal. He had always been shit at reading signals. “Ask you…?”
“Go on. Nobody will hear you. It’s okay.” Her thumb was rubbing the back of his neck now, the edge of her thumbnail ever so lightly scratching at the base of his skull. “Tell Aunty Amy what you want.”
Teddy realized he’d never said it out loud before, had never outright asked to be tickled. All those years ago it had been something of a game, finding ways to provoke Amy into tickling him silly. But the idea of just asking was incomprehensible to him.
“Please…” He couldn’t say it. He couldn’t.
“Please what? Look at me.” Amy said it more firmly this time, casually slipping into a more dominant mode. Clearly Moira had taught her a few things. “Please…?”
“Please…” God, his mouth was so dry. “Please…tickle me.”
Amy squeezed his knee again, and again Teddy pulled away. It tickled.
“Good boy.”
This is one of the first stories I ever wrote and it's quite long so I figured I'd post it in chunks as opposed to one go. That way, if it's terrible I won't embarrass myself as badly, and if it's good I can milk the suspense. Win win. This first part is mostly set-up but the end felt like a logical place to stop for now as, again, it's quite long. Either way, I hope you enjoy.
Under Her Palm
Teddy needed a cigarette. He’d been craving one for days now but had been able to valiantly offset his cravings by keeping himself occupied. A cigarette would be his reward; he told himself, after he’d applied to enough jobs and unpacked enough boxes to justify the indulgence. The trick was to not have any lying around. Inevitably, by the time he’d accomplished enough to earn his nicotine fix he’d be too tired to bother with a trip to the store. But now he was halfway through his third beer and the smell of smoke was radiating off every new arrival at the bar. It was only a matter of time before he wandered outside to ask one of the barflies for a cigarette. He had a spare dollar if it came to that.
It had been nearly a decade since he’d visited The Shoehorn, in fact it had been his go-to bar as a teenager. After acquiring a fake ID just after he turned 17, Teddy would visit any chance he could. The bartenders might look at him askance, but if they ever doubted the authenticity of his ID they’d never said anything. The trick, he would tell his friends, was to tip generously. Teddy smiled at the memory. He’d felt like such a grown up back then, nursing Tecates and making small-talk with strangers.
But he felt far from an adult now. Just last month his living situation in the city had deteriorated to the point where he had no choice but to move back home with his parents. He had been one of the few people to actually make it out of this town and Teddy had sworn he would never return - outside of family events and holidays, of course. His parents had been incredibly supportive and understanding. In truth, it had been nice spending time with them those first few weeks. But being back in his childhood bedroom and sleeping on his old twin bed had gotten old fast. Now it thoroughly depressed him.
Of course, this was temporary – that’s what he kept insisting to himself and anyone who bothered to ask, anyway. But two months had gone by and the longer things went on, the more boxes he unpacked, the less and less temporary the situation felt. Teddy had been lucky enough to find work here and there, but at the rate he was going it would be nearly a year before he could to afford to move back to the city, just shy of his 27th birthday.
Shit, he really needed a cigarette.
“Screw it”, Teddy thought to himself, downing what remained of his now lukewarm beer. “If there was ever a time to treat myself it may as well be now.”
Teddy hugged his jacket close to his body as he stepped outside. It had become decidedly chillier since he’d arrived. He was drunker than he thought and was still struggling with the buttons of his jacket when a familiar sound stopped him cold.
Heheheheheheheh *snort* hehehehehehhehehehe….
Teddy’s mouth went dry. It couldn’t be….
But there was no mistaking her. Curvaceous and short, with full cheeks well framed by dark brown curls, there she was, his old babysitter: Amy Ruth Baker. It may have been nearly fifteen years since they’d last seen each other, but Teddy recognized her instantly.
Amy was tucked away in the corner near the window, lighting the cigarette of a tall, athletic woman with a bright blonde ponytail – the one who had made her laugh. Amy was appropriately dressed, warm and comfortable under a thick, wool sweater that hugged her prodigious bosom while complimenting her dark jeans and red converse shoes. She must have been around 40 years old now. From what Teddy could tell, Amy had gained some weight, but so had he since he’d been home. Amy had been very athletic in her younger years, sturdy. She was often tasked with playing goalie or among the first to be selected for the wrestling team. He remembered that she had always been very strong.
But of course, that’s not all he remembered.
No, what Teddy remembered best was Aunty Amy, the Tickle Monster. He had always been reasonably well behaved as a boy. In fact, he had an almost pathological fear of getting in trouble. It was so pronounced that he’d even get a pit in his stomach whenever he watched teens sneaking out of the house or otherwise break the rules on TV. But as polite and well behaved as he was for his age, Teddy was still prone to the occasional outburst or tantrum. He may have refused to brush his teeth or fibbed about finishing his homework, and when he did Amy knew exactly how to handle him.
On one of their first nights together Amy had discovered Teddy’s weakness: he was unbearably ticklish. All it took was a crooked finger under his arm or a poke to the belly and he’d melt into a puddle of giggles on the floor. He still remembered the first time Amy tickled him. Really tickled him. It was so clear to him, even now. He remembered the scratchy feeling of the carpet rubbing against his cheek as Amy pinned him facedown on the floor, her butt pressed into his back as she pulled his ankles toward her and tickled the socks off his feet. He recalled the way she hooked her finger under the elastic lip of his sock and inched it up and down his foot, testing for tickle spots as he giggled and wriggled under her weight. He remembered her own socked feet, greying and pilly, resting inches from his face as she teased him mad, slowly breaking down what little resistance he had against her delicate touch.
“Uhhh oooohhhhh, does my tickawy Teddy have sensitive widdle paws?” she cooed, drawing little circles on his heel with her index finger as he’d giggled helplessly into the carpet. “You know what happens to baby bears when they lie to Auntie Amy, don’t you? Don’t you?”
He knew very well. In fact, nine times out of ten Teddy had intentionally provoked Amy into tickling him. He hadn’t been able to put his finger on it at the time, but there was something exhilarating about the time he spent squealing under her nimble fingers. Growing up he’d always enjoyed being tickled, or at the very least didn’t detest it the way some of his friends did. But when Amy tickled him it was different somehow. Maybe it was the fact that she clearly enjoyed it too, laughing nearly as much as he did sometimes. He had a vivid memory of looking up at her through teary eyes to find her smiling down at him, giggling along with him as she played “accordion” with his ribs until he was hoarse from laughter.
Then time passed as it always does. Teddy grew up. One day he was too old for a babysitter, and certainly too old for the Tickle Monster. But as puberty kicked in and he grew into an adult, Teddy found that tickling had taken on new significance for him. It did not take long for him to realize that nearly every fantasy he had revolved around tickling or being tickled. By the time he was 20 Teddy learned to accept the truth: he had a potent tickle fetish. He spent many a night on tickling forums, reading stories, watching videos, and sharing formative anecdotes with likeminded individuals online. He’d mentioned Amy there more than once, and as time passed she became more and more central to some of his most vivid fantasies. He often found himself alone at night, touching himself at the thought of being under her control once more, her cooing teases softly into his ear as she tickled him hysteric.
And now there she was, standing outside the Shoehorn, lighting someone’s cigarette. By the time Teddy realized he was staring it was too late.
“Teddy? Teddy is that you?”
Amy was looking right at him now, smiling in recognition. She didn’t have to ask. She knew it was him. Teddy felt his ears getting hot as he waved at her awkwardly.
“Hey Amy. Good to see you.”
“What are you doing back in town?”
“Oh, I’m just vi-“
Amy put her hand up to her ear and leaned forward a bit.
“What’s that? I can’t hear you. Come on over. Don’t be shy! Be a good boy and say hello.”
Something about the way she said that last bit made his pants feel tight. Nevertheless, he stuffed his hands in his jacket pockets and shuffled over to Amy and her friend. Amy put her hand on her companion’s back and gestured toward Teddy.
“Moira, this is Teddy. I used to babysit him back in the day. Teddy, this is Moira. She’s an old friend.”
Moira held her cigarette between her lips as she stuck out her hand to shake.
“Pleasure to meet you, Teddy.”
“Likewise.”
Amy kept shifting her weight from foot to foot, rubbing her hands together to keep warm. Her cheeks were pink and her eyes ever so slightly unfocused. She was a little drunk. This felt somewhat scandalous to Teddy, who had only ever seen her drink Powerades and Diet Cokes in the time he’d known her.
“What are you doing in town, buddy? I thought you’d moved away.”
“Oh, just visiting. Figured I’d say hi to the folks, help them out a bit.”
“Help them out? They’re not…” Amy seemed genuinely concerned.
“Oh! No, no. They’re fine. Just, uh…being a good son, I guess.”
Amy smiled and put her hand on his shoulder. Teddy could feel his heart beating faster as she turned toward Moira.
“I bet you are. Moira, I swear, of all the kids I babysat Teddy here was probably the best-behaved little boy of the bunch. He was always so polite and quiet, well, except for…” She let it hang there a moment, giving Teddy a knowing look. “…well, lets just say I had to put his foot down now and then. Sorry, my foot.”
Realizing her slip of the tongue, Amy giggled to herself.
Hehehehehehehehehe *snort*
Teddy could really feel the weight of her hand on his shoulder now. Why was he suddenly so warm? Goddamn he needed a cigarette.
“Excuse me, Moira, but could I bum one of those?”
Moira wordlessly handed him a cigarette. Amy gasped.
“Teddy! Since when do you smoke?”
“Since college. I don’t know…”
“I don’t know if you remember, but when you were little you promised me you’d never, ever smoke.”
Teddy shrugged and smiled at the memory. He had promised her that, hadn’t he? Then again, he’d promised a lot of things while pinned beneath his chesty babysitter.
“Yeah, well…things change.”
“Do they?”
Amy was looking right at him now, a slight curl to her lips and a mischievous glint in her eye as she challenged him. He recognized that look. Both anxiety and excitement began comingling in his gut. A black car pulled up to the curb and Moira crushed what remained of her cigarette beneath her boot.
“Shit, that’s my car. I gotta run.”
She shook Teddy’s hand and hugged Amy goodbye, promising that they’d see each other again soon. Then she got in her Uber and took off into the night. Teddy and Amy lingered outside a while. She teased him a bit at first for smoking but soon found herself taking a drag of her own once he offered. Eventually the cold got the better of them and the two decided to move things back inside.
At the bar the two finally caught up in earnest. Teddy told Amy all about his time in college and the jobs he’d worked after graduating, the friends he’d made and parties he’d attended, always taking care to obscure the details of his present circumstances. Through their conversation, Teddy learned that Amy had gotten an MA in psychology but had found some difficulty getting her footing in the field once she’d earned her degree. She still lived in town, not all that far from the Shoehorn actually, and had secured some part time work as a hostess at a local Mexican restaurant. Teddy couldn’t be sure, but after a couple of drinks it felt like their banter had taken a warmer, slightly flirtatious tone. But surely that was all in his head.
“So how do you know…?” He was searching for her name. He was drunker than he thought.
“Moira.”
“Yes, Moira! How do you two know each other?”
Amy smiled and took a sip of her Blue Moon.
“We met in college, actually. She was a poli-sci major with a wicked sense of humor, which is why I think we got along so well. She had a little…side hustle that I helped her out with from time to time. Still do, actually. Mostly I just drive her places, check in, stuff like that. Help out sometimes, if she asks”
Teddy nodded, playing with the little red straw sticking out of his now room-temp whiskey sour. “Am I allowed to ask what the side hust-“
“She’s a dominatrix.” Amy said bluntly, watching Teddy’s face for any trace of a reaction. She noticed him swallow and raise his eyebrow ever so slightly. “I drive her to the clients houses and stay nearby in case anything happens. Nothing ever does, mind you, but I think she feels safer knowing I’m there.”
Teddy couldn’t believe this. As far as he was aware he’d never met a dominatrix before. So many of his fantasies – all of his fantasies, really – revolved around being dominated by women and tickled into submission. He briefly thought of Moira, and what it might be like to be at her mercy. He imagined her effortlessly pinning his hands above his head with one hand while counting his ribs with the other. His pants were growing tight again.
“Oh wow. And you, uh, you said you ‘help’ from time to time? What does that mean?”
Amy set down her drink and cleared her throat, not making eye contact with Teddy.
“Well, one day she had a client with a certain…preference. Apparently he’d glimpsed me when I was dropping Moira off and I guess I fit a “type” that was agreeable to his fantasy. He asked her to see if I’d be interested in assisting her in the session and I agreed. One thing led to another and…well, I actually had a lot of fun. So now whenever the clients request it, I help Moira out in…certain situations.”
“You said you fit a type. What type is that?”
Amy shrugged.
“Maternal, I suppose. I remind some men of their moms or aunties or…babysitters.”
Teddy swallowed.
“Can I ask what the clients usually want you to –“
“I tickle them.” She was looking Teddy straight in the eye now, her tone warm but firm, assured. Teddy’s mouth went dry. There was no way this was real. He could feel blood rushing to his cheeks, among other places, and was keenly aware of his heart beating faster in his chest. Noticing his reaction, Amy drew inward a little bit, embarrassed. “Oh honey, I didn’t mean to fluster you. I’m sorry. We don’t have to talk about this.”
“No!” It came out more forcefully than he’d intended. Amy tickling people was all Teddy wanted to talk about. He registered Amy’s surprise to his reaction and tried to quickly backpedal from his outburst. “I mean, uh, I – sorry. Just, that’s interesting is all. What do you mean you…’tickle’ them?”
Amy watched him for a moment, her eyes searching for something in his face. She’d been caught off guard by just how easy it had been to talk to Teddy now that he was an adult. They had been friendly when he was younger, sure, but she’d always remained professional. They mostly talked about school, cartoons, family, that sort of thing. She’d never expected that she’d one day be talking to him about anything even remotely sexual. Amy would never admit it, but she cared what Teddy thought of her. She wanted him to see her the way he had when she last babysat him, as someone who had their shit together. An adult.
But when she told him about her work with Moira, there had been no judgment, no disillusionment. Sadly, this had not always been the case when she opened up to people about it. But this went beyond mere curiosity, there was a hunger to Teddy now that she hadn’t noticed earlier. Once the conversation turned to tickling and his interest peaked, something clicked for Amy. Maybe it was the alcohol, maybe it was nostalgia, but at that moment all Amy wanted to do was tickle Teddy silly. And she knew he wanted that too. She smiled hungrily at him and decided to move in for the kill.
“I think you know exactly what I mean.” Amy purred as she leaned forward, resting her warm palm on Teddy’s knee. “Turns out some people are willing to pay pretty good money for some tickle time with Aunty Amy.” She gave his knee a little squeeze. It tickled. Teddy pulled away instinctively. Amy raised an eyebrow. “Something wrong, buddy?”
Holy shit, this was happening. Teddy cleared his throat and pressed his knees together, hoping he could hide his excitement.
“N-no. Nothing. Just…surprised me is all.”
“Oh yeah? Are you sure it isn’t something else?”
“Like-like what?”
Amy gave a little pout, like she’d just spotted a cute stray puppy in need of a good home. “You know what.” She beckoned him now, curling her index finger to bring him closer. “Come here…”
Teddy leaned in. Amy did the same. She placed one hand on the back of his neck and brought him in close. He could feel her warm breath tickle his ear and send goose bumps down his back as her voice dropped into a husky, maternal register. “Are you still my tickly widdle teddy bear?”
Amy’s hand was back on his knee, now drawing tickly little circles. Just a tease, light enough to titillate without evoking a laugh. It was getting harder to hide his erection, which was now straining forcefully against the zipper of his jeans. He could taste the bitter adrenaline creeping up the back of his tongue.
Barely able to believe it, Teddy could only eke out the most bashful whisper in response, “…yes.”
“Good boy,” Amy breathed. She pulled back and looked at him with a dreamy smile, her finger still lazily drawing circles on his knee, which was now bouncing ever so slightly from excitement. “Now ask me.”
Teddy was confused, his mind clouded by arousal. He had always been shit at reading signals. “Ask you…?”
“Go on. Nobody will hear you. It’s okay.” Her thumb was rubbing the back of his neck now, the edge of her thumbnail ever so lightly scratching at the base of his skull. “Tell Aunty Amy what you want.”
Teddy realized he’d never said it out loud before, had never outright asked to be tickled. All those years ago it had been something of a game, finding ways to provoke Amy into tickling him silly. But the idea of just asking was incomprehensible to him.
“Please…” He couldn’t say it. He couldn’t.
“Please what? Look at me.” Amy said it more firmly this time, casually slipping into a more dominant mode. Clearly Moira had taught her a few things. “Please…?”
“Please…” God, his mouth was so dry. “Please…tickle me.”
Amy squeezed his knee again, and again Teddy pulled away. It tickled.
“Good boy.”
