Jacks Awakening Ch. 01

This is my first story! Please CnC :x

Chapter 1: The Mistake

Another hard day at work, finishing late yet again because my boss needs me to do her work for her and saying no is harder than you first think. I dump my keys into the bowl near the door and waddle into the kitchen. My boots fall off my feet on the way and I reach up into the top cupboard and grab out some cereal to have a quick dinner. "Another day, another day alone", I muse to myself. Being a 25 year old effeminate male has meant I rarely go out and as a corollary, still a virgin.

I sit in front of the TV, pick my legs up onto the sofa and start browsing through the channels. Finally deciding on a soap drama thing I settle in for the night. Kicking my trousers off revealing my frilly panties and garter stockings, pull off my shirt but leaving on my leather corset as I like the feeling while I sleep.

Throughout my life I've always found myself a little strange, always feeling for both men and women and often getting crushes on both as well. I've always been into fashion and envied the elegant beautiful clothing women can wear and a few years ago started to dress privately as I wished. I found a lovely tailor who made me some fitted corsets and she helped with tips on how to keep it a secret from my workmates.

The feeling of soft, supple clothing on my skin made me feel happy, comfortable and more of a complete person. Of course I enjoyed using them in the bedroom as well, having always loved anal play since I discovered it at a young age. The TV drama evolves into a classic story of a man and a woman falling outa nd getting back together again. Tiredness catches up to me and I slowly drop asleep.

After a couple of hours I'm woken up by a text on my phone, a 'friend' sending me a picture of him and his girlfriend having sex doggy style, the woman seemingly screaming in pleasure. "Thanks for that, fuck face", I mutter and then try to fall back asleep, but by now the image had burned into my mind. Now completely awake I'm struggling against the soft cotton of my panties, rubbing my legs together to squeeze my balls together.

Squirming against the image, my fingers gently strolling up to my lips where I rub the soft skin against my tongue. My finger like a surrogate tongue of an imaginary lover wrapping around mine in a passionate kiss. My stomach feeling fluttery and light as my mind races through possibilities.

I rush upstairs, I need something to satisfy my lust. I delve into my drawer of devices and dig out a big, real looking dildo. I start talking to it like it's my boyfriend. "Well hello there big boy, whats that? You want me to suck you?" I say, with little embarrassment as I'm by myself. I fall down onto my bed, throwing the stuffed animals off and rubbing the toy over my chest.

My nipples immediately get hard and I rub the head on them, bouncing them up and down, the feeling making me go crazy. I bunch up my pretend breasts, rubbing the dildo with them and licking the tip. The thrill of this sends my entire body into chills and I start to take the bulbous head into my mouth. Dying for the taste of cum I rub my fingers on the top of my sissy dick to collect pre-cum and suck my fingers clean.

I roll over, and slap my round tight ass and give out a squeal. With my other hand I reach into my bedside cabinet and grab out my (well used) bottle of lube. I empty some into my hand and start fingering my asshole open. First one finger, then two, pulling my panties to the side making sure my cock can't escape, tonight I was nothing but a sissy slut. I grab the dildo and start sucking it again, It's very wide and I haven't been able to get it in my sissy hole yet, but tonight is the night I thought. So I take it in my mouth as far as possible, about half way! Amazed that I was able to get close to 4 inches in my mouth I get lost in the moment and force a third finger into my ass. A muffled moan comes out and I start finger fucking myself, the knuckles bumping against the walls of my ass and bringing me and closer to the point of no return.

I pull the cock substitute out of my mouth and gasp for air. Once I get my breath back I start begging for it in my ass, savoring the idea in my head. I Roll backwards and firmly affix the suction cup against a near wall. Down on my knees I go, sucking away at the cock, pre-cum flowing from my own begging for it in me. After nearly choking myself trying to deep-throat I stagger to my feet and drop my panties to the floor. I pick them up and stuff them in my mouth, sucking the pre-cum out of them.

Reaching between my legs I grab the huge head of the dildo and position it carefully. My mind rushes with adrenaline and I force it as far as I can in one go. I scream loudly, even through the panties, my legs shaking with pain and pleasure as I stand there, proud I've taken it in. My corset tight on my stomach helps me feel every bump, every ridge inside me. Once my composure's regained I start to move. Slowly at first as my raw asshole grabs the dildo and tries to suck it in deeper but eventually speeding up. My own petty cock bouncing between my spread legs as I force the dildo in deeper and deeper, clear liquid dripping from the eye of my dick over my floor. I can feel my climax building and I start to moan louder and louder.

When I can't take any more I pull the panties out of my mouth and wrap them around my cock. I stroke a couple of times and climax, I bury the dildo right to the hilt in my asshole and strings of cum fly over the floor. I stagger, half naked and used in to my bed and pass out, not realizing my curtains were open the whole time.