The taller man of the two moved behind me. He carressed my cheek with a calloused hand, sending shivers shooting up my spine.  His rough hands grabbed at my ass, pulling apart my cheeks and exposing my hole. I quivered a little in my restraints and moaned. I couldn't believe it - I was about to lose my virginity. 

Part 1

For a guy, I wouldn't say I was bad looking. I had a slender athletic frame, often swaying more towards the former of the two. My hair was a dark brown, and I'd grown it out to my shoulders. My skin was tanned enough to stand out amongst my friends, which suited my brown eyes that often looked black in the right light. I'd never been the most masculine of the bunch, but I got by on my looks and boyish charm. However, as I got older, I realised that it wouldn't be quite the blessing it had been. My friends got taller, stronger, and manlier. Whereas I stayed the same; a guy that looked faintly like a girl.

I tried to bulk up and change but to no avail. I was stuck as a bit of a runt. The doctors were stumped and guessed I was just a late bloomer. 

So here I am, at twenty years of age, no facial hair, barely any muscle and standing at about five foot six. I'm Kai, nice to meet you.

As my friends grew older and started dating properly, I realised not many girls were into me as they once had been. I mean, it was fair - I was the opposite of the masculine Greek gods that they'd idolised on Instagram. Out of luck and out of, well, any sexual communication, I started to explore pleasuring myself since no one else seemed interested in helping. 

I dove into porn. I absorbed as many fetishes as I could and before I knew it, I was standing in my room, admiring the cute girl in my full-length mirror. Except... it wasn't a cute girl. It was me, dolled up, cleaned and ready for another night of pretending to be fucked senseless. 

I was in the typical 'slutty' schoolgirl outfit - pigtailed hair in red bows, plaid miniskirt and close-cut crop top, white stockings with bows of course and cherry lipstick with black mascara. I wasn't too big on makeup as I've never seemed to need it to be mistaken for a girl, so I don't like it when I dress up in private.

I eyed myself in the mirror, posing and strutting, thrusting out my ass and pursing my lips. I was hot. I was the kind of girl I wish I could fuck. Spinning round, I looked at the toys laid on my bed, the small collection I'd managed to gather over my few years of debauchery: a small purple plug, an eight-inch pink dildo and several red ropes for bondage. I had plenty of lube and condoms too, for good measure. 

I surveyed my equipment, double-checked my door lock and got busy. I loaded up one of the many JOI and encouragement playlists I'd made and set sights on my ropes. I wound the first around the base of my cock and balls, then separately around my cock - sorry, it was quite small, so I usually call it a 'clit' when dressed up - and then pulled the rope down between my balls, separating them and making them bulge in a wonderful ache. Tying the clit-trap off, I grabbed my plug and begun sucking, whilst staring at the screen as images of cocks and creampies caused my eyes to glaze over. 

I don't remember how long I worshipped the small plug, but I was snapped out of my daze by a painful half-erection, so I knew it was time. With a little bit of lube and the saliva coating the plug, I slipped it into my tight ass. Immediately I moaned in ecstasy and began stroking my clit whilst sucking a painted finger. It felt like heaven; pushing just right on my g-spot and causing a bead of precum to appear at the end of my tied-up clit. I wiped it with a finger and greedily lapped it up. I wanted more, and I knew how to get some. I wrapped a much-too-large condom around my clit to catch anymore that would inevitably leak out of me.

As I continued lightly stroking, I grabbed my pink dildo. It was big, and I'd never fully gotten it in me. I was too tight, but tonight I was determined. Using the images on screen to guide me, I began to gently suckle the head of the dildo. My ass clenched around the plug as my tongue slowly teased the shaft, massaging the fake balls of it and coated the plastic cock in spit. I began to take it into my mouth, circling it with my tongue as it plunged deeper past my painted lips. I began to bob my head, only a few inches of the cock was in my mouth but I already felt like gagging. But I couldn't hold back and my inner slut came out. I took as much as I could, shoving it down my throat as my tied-up clit throbbed in pain. My eyes started watering as I held it down my throat, gagging and spluttering I finally released. Large strings of spit - and probably some tears - attached from me to the head of the cock as I gasped for breath. Deepthroating was fun, but my ass was pulsing and wanted more. 

I moved the laptop so I could still see the porn and got into a more comfortable missionary position. I pulled out the plug, gently fucking myself a few times with it before removing it completely. I had nowhere to put it, so I kept it in my mouth, tasting myself and moaning as I did. My clit began to ache more as I teased it with the much bigger dildo. "You're about to be fucked by a real cock," I told myself. With a few squirts of lube and the willpower of the slut I knew I was, I placed the head of the cock at the entrance to my hole. I was ready.

With a deep breath, relaxing my ass and praying in my head, I pushed the thick pink dildo into me. I couldn't help but moan like a bitch in heat as the first two inches or so slipped into me. It felt incredible. I began to push my body onto the cock, forcing another inch or two inside me. By this point, I was a mess. My tongue lolled out of my mouth around the plug and my clit was leaking precum endlessly. My inner slut took over and instead of waiting for the rest of the dildo, I began to fuck myself on what was in me. Bouncing my ass on my pink boyfriend, my eyes rolled back into my head as waves of pleasure spread through my lower body. With what little makeup I had on running down my stained face, and my tiny cock leaking juices in its rope prison, and the large pink cock fucking my ass I couldn't hold it back. 

It started slow, but then grew exponentially. Soon my whole body was quivering as I rode the fake cock to a wonderful, mind-boggling orgasm. I moaned and wept, and moaned more as my ass was pounded by the invading dildo. My clit burst and began pouring cum into the condom. 

As it died down - and I got my breath back - my ass began to tighten around the dildo and I had to pull it out. My hole felt hollow when I did, empty. I needed something else in there. I picked up the plug that had fallen out of my mouth as I came and slid it easily into my gaping little hole. 

I was still ridiculously horny, so I took off the cum-fulled condom and emptied it into my waiting mouth. I loved the taste of it, salty-yet-sweet, and so delicious. I was in love with my own cum. 

Mindlessly, I started watching the copious amount of porn on screen and began licking the dildo clean of my own taste. I was happy, another Saturday night well spent. 

As I began to close off the windows of porn, I realised I'd gotten a new email, from someone I didn't recognise. I opened it, trusting the safety of my email client.

To: kai_02@gmail.com
From: mistressS@desires.com

Hello Kai,

my my. What a show! Thanks for that, really. Of all of those I've recorded, that has to be one of my favourites. 

I'm Sarina, or Mistress to you now. Unless you want the attached video to leak. 

You'll be hearing from me soon.

Ta-ta for now.

S x

I read the email in a post-orgasm daze. What? Video? Recordings? I opened the attachment, and to my horror, found a video of myself. Dolled up like a schoolgirl, makeup ruined and fucking myself with a thick pink cock. There was no doubt it was me. Fuck. 

I panicked, my heart beating faster than it ever has.

What the hell is going on?