“Thanks for doing this, Alex,” Mr Stevens said as he shook my hand.
“Bye Mr and Mrs Stevens!” I called out from the front door as my neighbours waved before stepping into their car. They were celebrating their anniversary with a night away and I’d volunteered to babysit their young son. Timmy was a good kid, so even though most 18 year olds idea of a fun Saturday night probably didn’t involve looking after a 5-year-old, I didn’t mind. Besides, he was already in bed and that meant I had plenty of time to do what I’d really come here to do.
With Timmy hopefully asleep upstairs, I sat down on the couch, flicked on the TV for some background noise, and opened my bag. I took my new outfit and laid it down, piece by piece, on the coffee table, savouring the feel of the exotic, delicate fabrics. Next, I peeled off my boring guy clothes and crammed them into my bag, until I was sat on the couch in my neighbour’s house completely naked, butterflies in my tummy, my smooth legs and ass buzzing at the unfamiliar sensations, my cock stiffening with excitement. I took a deep breath and slowly got dressed.
There was no mirror in the living room so I made do with my phone, posing for some sexy selfies in my girly lingerie. Then I remembered the Stevens had a mirrored wardrobe in their bedroom. I could pose on the bed and fully appreciate my new look, maybe even take a few more pics. So I slowly tiptoed upstairs, careful not to make a sound that might alert Timmy. I entered the bedroom, turned the bedside lamp on real low and stepped in front of the mirror.
I looked hot. Well, I looked very cute, at least. I was wearing a sheer black babydoll nightie with red lace cups, open at the front below the bust and revealing my tight tummy and belly button. Below I had on a matching thong, black with a cute red ribbon tied in a bow at the front. The thong was so small it barely held my little balls while the tip of my now rock-hard cock poked up over the band behind the red bow. My legs were covered to the mid-thigh by sheer black stockings topped with a red lace frill. I turned around to admire the rear view. The babydoll barely covered half my ass, exposing my plump round cheeks separated by a hint of black g-string buried deep between. I didn’t have a wig, so I still looked like a boy with my boring boy hair, but I was the cutest boy you’d ever seen.
Propping my phone on the bedside chest, I hit record and got onto the bed, trying to look as sexy as I could. I knew I probably looked very silly, but I was having fun and who cares, no one else was here to see me. I crawled towards the camera, my ass poking up in the air. I turned around with my ass facing the camera and pulled the g-string aside to show my little hole. I sat back with my legs apart, rubbing my cock through my panties and moaning as seductively as I could.
That’s when I thought I heard a door close. I froze and held my breath. It was just Timmy getting up to go to the bathroom. I would just wait for the toilet to flush and for him to go back to bed. A minute passed in what felt like an hour, but then I heard the toilet flush and footsteps echo down the hall. I breathed again, grabbed my phone and leaned back on the pillows to watch my performance. The bedroom door opened and I froze again.
“What the…?” said a male voice.
I couldn’t move. I dropped my phone on the pillow and stared in shock. It wasn’t Timmy.
“Wait… Alex? Is that you? What are you… doing?!”
It was Scott, Timmy’s much older brother. He was a few years older than me, a few years above me in high school, but we’d never really been friends. He was a sporty jock type; I was very much not. He’d moved out last year and was living on his own. Or so I thought. Why was he here? And, as my panicked mind desperately tried to make sense of the situation, with Scott finding his kid brother’s babysitter dressed in lingerie on his parents’ bed, how was I going to explain this?
“Um… I… uh… can explain.” I tried to say. I really couldn’t.
That’s when I noticed how good-looking he was. I’d never noticed before. Why had I never noticed? He was tall, maybe half a foot taller than me. He was wearing a basketball style singlet which showed off his muscular arms, skinny denim shorts cut off just above the knee and low-top trainers.
“Well?” said Scott, after a few moments of silence.
“I… I… uh…” was all I could offer.
“Where’s Tim?”
“He’s… in bed.”
“Right,” he said, entering the bedroom and closing the door behind him. “So, you thought you’d offer to babysit him then, what, check out my mum’s wardrobe and dress up like a fucking girl?”
“No… I mean… no, they’re mine. The clothes.”
“Fuck, of course they’re yours. I always knew you were a little sissy, Alex.”
He took a few steps closer until he was standing at the foot of the bed. He looked even bigger now. I could feel my cock tingling again and pulled my knees close to my chest to try to hide my excitement from him.
“You know, for a guy you actually make for an alright girl,” he said, almost sounding impressed.
“Don’t tell them,” I whispered.
Another few steps and he was standing next to me, his crotch now level with my eyeline. I couldn’t help but look at bulge in the shorts. For a second, I thought I saw it grow.
“Or what? What if I don’t tell them? You’re gonna beg, say you’ll do anything I want as long as I keep your sissy secret?”
“Maybe…?” I looked up from his crotch and thought I could sense a strange look on his face.
“You’re gonna beg me to, what, let you suck my dick so I don’t tell anyone?” He laughed. “I’ve seen that porno before, dumbass. I’m not into blackmail. And besides, in those pornos the girl’s always saying ‘No please, I’ll do anything’ like she’s really reluctant. Like she thinks she’s doing the guy a favour. But you know what, sissy, you know it’s the other way around. You know he’s really doing her a favour. She’s not reluctant at all, she’s just faking it. She wants to do anything. She’s a slut.”
I must have looked confused. I certainly didn’t know what to say.
“I think you’re a slut, too,” Scott continued, leaning down closer to me. “A little sissy slut. So here’s how this is gonna work. I’m not going to blackmail you to suck my dick. Maybe I’ll tell my parents what you were up to. And maybe I won’t. I don’t know, I haven’t decided yet. What I do know is that what I decide to do is gonna have nothing to do with whether or not you suck my dick. Got that?”
I nodded, still confused, still staring at his crotch.
“But you are gonna suck my dick, aren’t you? You haven’t taken your eyes off it from the moment I stepped into this room. The whole time you’ve been terrified that I’ve discovered your little secret, you’ve been thinking about my dick. Haven’t you?”
I nodded again.
“So, no need to resort to blackmail. You’re just gonna ask nicely, ok?”
“Ok,” I said, and before it really registered, I continued, “Can I suck your dick?”
Scott straightened up and, looking down at me, nodded towards his crotch. I got the hint. I leaned over and touched the front of his shorts. I could feel his heat through the denim and traced the large outline of his cock with my fingers. I fumbled the button undone at the waist then slowly unzipped the fly. The black boxer briefs underneath bulged then tented alarmingly as I freed him from the confines of his shorts. This close, I could smell his sweat and see the curls of hair above the waistband of his boxers. The sight and smell were a heady rush. I could feel my own cock straining once more against the soft, lacey thong.
He still hadn’t said a word when I pulled down his boxers and let his big cock hang free. I don’t know how big I expected it to be – I’d seen plenty of big dicks in porn, but the only cocks I’d seen in real life until now were my own (5 inches when erect) and my dad’s (bigger than mine, but it had been so long ago I couldn’t remember the details). Scott’s dick was thick, maybe as thick as my wrist. And it was long, maybe even as long as my forearm. The base and his balls were covered in dark hair while the shaft curved upwards and was circumcised, with a large head. Even in the soft lamp light I could see pre-cum glistening on the tip.
My tongue licked the head of his cock, tasting the salty sweetness. What surprised me was not only how soft it felt, but how warm. I took the whole head in my mouth and began to move back and forth, frantically trying to recall precise details from countless blowjob porn clips. I decided to just focus on the head, rolling my lips and tongue just onto the shaft before drawing back, and soon I settled into a steady rhythm. If I was doing it wrong, Scott didn’t seem to mind.
“Mmm.” I heard him grunt what sounded like approval. I glanced up, again feeling so tiny beneath him, and realised he had his eyes closed, his head tilted back. I kept going, now also using my left hand to massage the shaft while I running the fingers of my right hand through his public hair to caress his balls.
“Keep doing that,” he urged, and placed a hand on the back of my head, encouraging me to accept more of his cock into my mouth.
“Yeah, that’s it, you slut,” he said, louder than before. I glanced up again and made eye contact with him. His grip firmed on the back of my head and I could now feel him pushing his hips forward, impatiently. “You love sucking my dick, don’t you, you little sissy slut.” He was soon thrusting his cock in and out of my helpless mouth.
I felt him tense up. He grabbed my head with both hands and shoved his cock to the back of my throat, nearly causing me to gag. I felt something warm hit my throat then another hit the roof of my mouth. He pulled out and wrapped his big hand around his thick cock and stroked himself a few times, shooting one long rope of cum across my face and then a second directly into my still open mouth. He squeezed out one final, smaller trickle of warm cum onto my cheek then pushed his cock back inside my willing mouth. I continued to suck him, trying to swallow as much of his cum as I could while his cock occupied my mouth.
He pulled out again and wiped his dick on my cheek, smearing yet more cum across my face. He wriggled back into his boxers and zipped up his shorts.
“You’re a good little cocksucker,” he said, as he left the room. “Now go clean yourself up.”
I looked in the mirror and saw a beautiful girl dressed in black and red lace, sitting on a bed. Her face was covered in cum. Her name was Amy. She looked so happy.