This story is original fiction by me.
It depicts sexual acts and is not intended for minors.
by AmieLA (shortskirtAmie@hotmail.com)
Travis had earned a reputation as the most reliable babysitter in the neighborhood: he was available at a moment's notice, he was fantastic with the kids, and always left the house in impeccable condition. When the night of Lisa's benefit dinner came up, Brian had no hesitation in calling the 15 year old Travis to watch the kids.
"Would it be alright if I picked you up around 6:30?" offered Brian, knowing that Travis would otherwise have to bike the mile or so between his house and the Madsen's.
"Really, Mr. Madsen? Yes, please, that'd be great! I mean, thanks!" stammered Travis.
Brian stifled a laugh at Travis's enthusiasm. "We should be home around 11." What a charming kid, thought Brian. Travis had always held had such a unique presence about him. Brian could remember watching him circle the neighborhood on his bike as a younger boy, his bright blond hair and striking blue eyes undeniably magnetic.
As the sun began to falter, Brian and Lisa were busy prepping for a formal benefit dinner. Brian finished a precise shave. He lent Lisa a hand attaching the clasp of a choker of pearls, running his nose of the softness of the back of her neck, taking in her delicate perfume. "Mmmm…" she purred, and he stiffened a bit in his slacks.
"Ah, shit, I have to pick up the babysitter," as he saw the alarm clock reading 6:17.
"Is it Travis?" as she zipped her black cocktail dress.
"Yup," as he patted down the dresser, searching for his keys.
"Good," said she, almost an afterthought as she turned to her makeup.
Brian waved to Travis's parents as he backed out of their driveway with their son in the passenger seat. Brian patted him on his bare knee and made small talk. "So, how's school, champ?" The undersized Travis just smiled brightly back at Brian. He's an odd one, though, isn't he? mused Brian.
Travis knew the routine; he'd feed the kids their macaroni. Leave the dirty dishes, pleaded Lisa, knowing that Travis wouldn't listen. Have a lovely time, he bid them.
"Lovely, yes. Thank you Travis. We'll see you around 11." said Brian.
And then there was the smile again.
9:17. This was Travis's favorite time. He'd put the kids the bed, done the dishes, even straightened up the living room. Now was what he'd been looking forward to since yesterday, his one guilty pleasure: he could dress up like the girl he dreamed of being.
Terrified to attempt it at home because of his hyper-strict parents, who might just implode from confusion if they knew, Travis awaited the chance to babysit. He had dressed up at the Miller's, the Olson's and the Rosen's, but the Madsens were easily his favorite. Lisa Madsen had such a petite little body. Just like mine, thought Travis. We could be sisters.
He snuck into Brian and Lisa's bedroom, listening intently for any stirring in the children's rooms. Silence. He tiptoed to her bureau. Opened her underwear drawer like he was unearthing the dead sea scrolls. He gently placed his hands on top of the two neatly folded piles of panties: there were boy shorts, g-strings, even a thong. Mrs. Madsen is one sexy lady, thought Travis. He picked a pair of low-riding teal boyshorts and set them on the bed. Next, he picked out a spaghetti-strap, flowered summer dress. He held it up in front of himself and saw the way the bright blues and yellows made his eyes sparkle. Yes. He stepped into a pair of strappy low heels. Perfect fit he thought. Now, to get ready.
He turned on the tub, adjusted the temperature, then began to fill it. He located Lisa's razors, and once the tub was filled, set to shaving his legs. The softish hair of his legs came off easily in the hot soapy water. He raised his leg straight in the air just as he'd seen in so many commercials. It felt so smooth.
Out of the tub, he saw the tuft of pubic hair above his soft cock. Hmm. He trimmed it into a neat triangle, having thought he'd heard somewhere that boys like that.
He dried off and carefully applied a coat of nail polish in peach to his toes then his fingers. As the polish dried, he carefully set to doing his mascara, eyeliner, blush, lip liner and lip gloss. The lip gloss was his favorite. He'd picked another shade of peach that had a metallic finish. He looked just like Trinity Smithson, the hottest girl in 10th grade, he thought. Matt Jansen fingered her at a party a few months ago, according to hallway gossip. That made Travis sigh. Oh, to be in Trinity's place that night… He finished by spritzing himself with the perfume that lay on the bathroom counter.
By the time his makeup was done and his hair combed straight and gelled so it looked like a girl's sporting a boyish look, it was 9:41. He only had 45 minutes or so to enjoy this, he thought, before he'd have to take it all off and go back to being a boy. He wasn't discouraged though; she was here now and was devoted to enjoying herself.
He had aroused herself by referring to herself with the feminine pronoun. It helped him fill the fantasy even more. Now he (she!) slipped the teal boyshorts over her freshly shaven legs. What a feeling. They rode low and showed the top of his sweet little ass. Now he slipped on the spaghetti-strap summer dress. It fell down and tickled the tops of his thighs, just a few inches over his panties. Finally, the shoes. He shuffled his way to the mirror for his grand reveal.
He gasped. Stunning, he thought. I'm a hottie!
He stared at himself as the gorgeous teenage girl he'd become for a good ten minutes. Now it was 9:54. Better enjoy this quickly, he thought. He walked to the door of Brian and Lisa's bedroom, listened carefully to make sure the children were still down then slipped out into the hallway. He made his way to the kitchen. He poured himself a tiny glass of white wine from an open bottle in the fridge. He'd never had a single drink in his life, but he loved the way that women looked with a glass of white wine in their hands.
He sat on the living room sofa, crossed his legs and sat there sipping his wine. He admired his nail polish. He mimed like he was at a cocktail party, even rested his hand on his imaginary boyfriend's thigh. Some day, he hoped.
He closed his eyes and dreamed of his boyfriend. He'd have chestnut hair, wavy. And friendly eyes. And broad shoulders. He'd kiss me in public, and when we got behind closed doors, I'd wrap my legs around him and he'd make me a women proper. And we'd get married, and honeymoon to the tropics…
Travis's full-fledged dream was interrupted by the sharp noise of the door from the garage opening. He sprung awake with a start. Or she did, really, as he was still head-to-toe a female. He couldn't believe he'd fallen asleep and now had the most instantaneous panic one could have. He wanted to die and melt into the floor and never be seen again. And he was trapped.
Brian walked into the room and saw Travis standing there, arms clutched at his chest, crying intensely. Brian's heart reacted first. He wanted to hold the poor kid, who was so busted. But he didn't reach out. Now was the time to help the kid. "Where are your clothes?"
"Under your bed," whispered Travis.
"Stay here and stay quiet. I'll be right back," assured Brian.
Travis was humiliated but consoled by Brian's soothing demeanor. He was such a kind man, such a handsome guy, my hero…
Lisa was already brushing her teeth when Brian entered the bedroom. "Are you going to take Travis home?" she asked.
"Yeah, right now," replied Brian, surprised to hear nervous complicity in his voice. He fell to his knee silently then reached frantically under the bed for Travis's boyclothes. He set a hand upon them and yanked them out. "Back in a flash," he said with relief as he cruised out of the bedroom.
He handed them to Travis who was standing in the same spot. "Put them on and I'll take you home. Travis slipped the dress up over his head. It stuck around his shoulder blades and Brian instinctively leaned in helped slide it smoothly off. What is this erotic energy? thought Brian. What the fuck is going on with me?
Travis pawed through his clothes. "My underwear! They're not here," cried Travis.
"I'll get them tomorrow. Lisa's in bed now, so just wear what you're wearing." Travis slipped on his jeans and t-shirt. He now looked like the most beautiful, tear-strewn boy-girl. Brian wanted to kiss him. They made eye contact and Brian hoped Travis couldn't read his thoughts. "Let's get you home."
They rode in silence nearly the whole way, but the energy in the car was palpable. It was uncomfortable, sure, but had the excitement of possibility too. Brian cursed himself for allowing himself the thoughts he had, but he didn't tried to stop them either.
Finally Brian broke the silence. "Do you think you're transgendered?"
"What?" asked Travis.
"I mean, do you think you want to be a girl."
"Oh. I… yes." Travis felt such relief. "Yes. Yes yes yes. Yes, very badly."
"Well I think you're a very beautiful girl," said Brian, playing the role of guidance counselor and hopeless flirt at the same time.
Travis was too embarrassed to reply. He felt hot in the face. Brian was the first person who had ever found out about his secret desire, and his response was so positive that Travis wanted to fling his arms around the man's neck and kiss him mercilessly.
A few more minutes of silence went by. They were nearing Travis's house, and Brian didn't want the magic to end. He settled on something more provocative to say, even though his better judgment told him to shut the hell up.
"So what do you do when dress up like a girl?"
Someone was asking Travis about his private ritual. He was bursting. "I put on makeup and pick out the cutest thing I can find to wear. And if I have time, I shave my legs."
"Did you shave tonight?"
"Really?! You shaved your legs completely?"
"Yeah! Do you wanna see?" asked Travis.
Here it was. The point of no pretense. Brian fumbled with what to say. But Travis had already started to unbutton his pants.
"Sure," muttered Brian, telling himself that he was just assuring the poor boy-girl, but secretly dying to see Travis's smooth legs. Travis was shimmying out of his jeans when Brian saw Travis's house approaching on the left. He slowed the car to a stop in the dead quiet suburban neighborhood. From where they parked, Brian could see Travis's front door.
Travis looked over at his male superior, now stripped down to his t-shirt and the teal boyshorts. Brian's breathing turned shallow. He looked like an 18 year old girl lying about in her underwear on a lazy Saturday morning. Brian was so exquisitely turned on. He was vaguely aware that he had let all his good sense evaporate, but he wasn't about to stop now.
They sat in the parked car and stared into each other's eyes. Brian semi-consciously turned the car's ignition off. "Well."
"Well." echoed Travis, his beautiful face beaming at the man.
Brian couldn't bring himself to touch the boy. Instead, Travis reached over and pulled Brian's hand to his thigh. He grazed his fingertips over the baby soft skin. "See?"
"Mm." Brian allowed his fingers now to play on their own. They traced their way from his sweet kneecap up to near his pantyline and back again. Travis stroked his arm sensuously. Brian had never once thought seriously of cheating on his wife, but here he was, with this magnetic boy dressed as a beautiful girl. And she was totally into him. He wanted to push her up against a wall, rip down her panties, and…
And go to jail, thought Brian. No, let him go. His fingers continued to stroke the tight teen body.
Travis could sense that he needed to make a move on his would-be suitor. He deftly pulled himself up and over the center console of the Volvo and sat on Brian's lap. landing his tiny ass sweetly on Brian's stiff cock.
The feeling of the young boy's ass resting on his tailored dress pants turned Brian into the animal he craved to be. He wrapped both arms around the boy and stroked his thighs simultaneously, drawing them dangerously close to his crotch. Smooth all the way.
Travis writhed and made little moaning sounds, rubbing his ass all over Brian's clothed hard-on. Brian nuzzled his nose up Travis's spine. Arriving at the nape of his neck, he smelled his wife's perfume mingled with Travis's sweet boysweat. I'm going to fuck this boy tonight, he thought.
His fingers trickled into the warm area between the boy's legs. His index finger gently infiltrated the boy's panty line, and the middle finger followed. The tip of his middle finger traced the area behind the boy's testes. Travis moaned like a bitch in heat, which egged the man on. He slid his fingertip to the edge of the boy's tight but welcome pucker, and just as he applied a bit of pressure he bit the boy's earlobe gently.
"AaaachhhAHH!" cried the boy as he ejaculated violently into his panties. His body writhed and spasmed. His knee hit the door so hard it sounded like a drum. He continued to pulse and move like he'd been struck by lightning. After ten or so seconds he subsided and collapsed gently into Brian's lap.
He curled up, resting against Brian's chest and sobbed gently. "Are you OK?" asked Brian with genuine concern. Travis sobbed, wiggled his way around and wrapped his arms around Brian's neck.
"Thank you," he sobbed into the man's ear.
They held that pose for a minute until it grew uncomfortable. Travis wordlessly worked his way back to the passenger seat and slid his jeans back on. Before he grabbed at the door handle, he stared once more at his man (HIS man). To Brian, he looked so tender. He had stopped crying but his cheeks were swollen and his eyes wet. Brian reached out to him and grazed his cheek with his hand. Travis leaned over, kissed Brian squarely on the lips, hopped out of the car and walked quickly towards his darkened house.
Brian watched him go. He reached his right hand and sniffed the fingers on his right hand. Jesus, he thought.
The End! This is the first erotic story I have ever written. If you like it, or if you don't like it, send me an email, OK? I'm at shortskirtAmie@msn.com