Sissy Stories with Con

Welcome to my first ever story! I'll be splitting this particular one up into a few chapters depending on then feedback.

Just a bit of info before we begin. Many details and characters in this story and the stories that might follow are based on real people. Before anyone asks, yes, I do own all items listed in this story and yes, I do use them. The story itself however is fictional. Please enjoy!

My name, or alias rather, is Con. I'm 19 years old and I'm completely straight (as far as everyone knows). Secretly I'm actually a closet bi. Most other boy's expect me to be a top because of my height and build. Being 6 foot 3 makes it hard to come across as submissive. My cock isn't particularly small either. I have a 6.8 inch dick (erect) so a bit above average, but nothing special. The moment I turned 18 and got my drivers license, I went to the local sex shop and got my first real dildo. I kept expanding my collection from there and I now own three dildos among other toys and trinkets. A 13 inch double ended dildo with a width of 1.75 inches, a 10 inch suction cup dildo with a width of 1.85 inches and my biggest dildo, an 18 inch long double ended dildo with a width of 2.5 inches.

It all started when I got a job working for a small ISP owned by a man we'll call Mr Q. He was a handsome man with a well built but lean body. I'd secretly stare at his masculine body, especially eying his bulge, every time he'd get out of the shower. Scandalous, I know! I would work for him personally as I was to be his successor one day. I came home from a long day's work, feeling much hornier than usual. I'd been pent up for an entire week now as I'd been holding of on any form of masturbation. Luckily, I would be home alone for the entire weekend. You see, I was renting a room in my boss's house. He would regularly stay at his girlfriend's pad though, leaving the whole house to me. As soon as I locked the door I stripped nude, got my toys and headed to the shower. I spent the next hour and a half properly cleaning myself, inside and out. When I was done, I headed to the lounge and got my toys ready. I was shaking in anticipation! As a bonus the walls were pretty thick so they were pretty much sound proof. I switched the TV on, connected my hard drive, went to my special folder (which just so happened to have about 10 hours worth of sissy and tranny porn pmv's), and started the first video.

As a start, I laid a large towel onto the ground, positioned myself, ass in the air, and lubed my asshole which was already tingling in anticipation. Using my fingers, I started slowly stretching my hole, getting it nice and lubed up. Foreplay is key! I fucked my hole to the beat of the music, in and out, in and out! Two fingers.. Three fingers... Four! At the same time I grabbed my 13 inch double dildo and started sucking on it. I was pretty good at that by now. Practice makes perfect! I went down on the dildo, shoving about 7 inches down my throat! I gagged hard as I pulled off, but immediately plunged back down, adding another 2 inches to the count! Up and down, up and down! In and out, in and out!

I was happily deepthroating 9 inches of the dildo while finger-fucking my ass. Nothing got me harder than choking on that dildo! (This was if I wasn't mercilessly fucking my ass.) My dick was viciously twitching in excitement at this point. No touching though! I wanted to cum a different way. I took the dildo out of my mouth. It was covered, top to bottom, in sticky, sloppy spit. I pulled my fingers out of my ass as well (which was now gaping) and scooped up the pre-cum which was dripping from my cock. Full of lust, excitement and glee I sucked about half of it down, thoroughly enjoying the taste, and puched my fingers back into of my gaping asshole, adding the rest of the pre-up to the my already lubed hole. I was ready!

I put the tip of the dildo against my asshole, slowly pushed the head in and then rammed it forward! Seven inches disappeared instantly! (Practice remember!) Rocking my hips back and forth I worked my ass onto the dildo until I was comfortably riding 12 inches. It was a delicious feeling. I pulled it all the way out and slammed it back in, feeling my fingers which were holding onto the other end, slap against my ass. Precum was constantly leaking from my cock as I fucked myself silly. I was feeling brave, so I decided to shove the whole length all the way into my ass and clenched down!

The dildo disappeared, my legs shaking viciously! I had a tantalizing dry orgasm! I was far from done though. I had an idea. It was a dangerous idea, but I'd done it before and was always careful, so I wasn't too worried. I grabbed my suction cup dildo and started to slowly push it in. Rocking back and forth, I fucked the double ended dildo even deeper into my ass! I worked into a rhythm until I was fucking myself with another six inches of dildo. This meant the double dildo was now 19 inches deep! Again, my legs started shaking and I clenched down. Dry orgasms were the best! I was leaking pre-cum like a faucet!

My cock bounced up and down excitedly as I relaxed my asshole. Totally paralyzed, I lay there for a few minutes until I could gather the strength to stand up. I pulled the first dildo out with a pop and soon the second slid out making an extremely lewd, wet sound followed by a bunch of clear, sticky lube dripping from my loosely stretched hole. Poor thing... Damn that felt good! I was in heaven! Despite all this, I wasn't done yet! There was one dildo left... Big Boy. (Yes, I called my 18 inch dildo Big Boy. And why wouldn't I? It's fucking huge and thick as hell!)

It was now time for the finale! I grabbed Big Boy and the lube. I didn't really need more lube but I just love getting all sticky! I opened the cap and poured a generous amount lengthwise onto the dildo. Getting back down on all fours, I jerked the dildo, spreading the lube evenly over the entire length. It was time, and boy was I excited! Pushing the tip against my hole while clenching as best I could, I felt a tingling sensation ripple through my body. I pushed the dildo harder and relaxed my ass. About 14 inches disappeared instantly! The pressure was insane! Slowly I started rocking back and forth to the beat of the music. I pulled the entire length out, gaping my wide stretched hole, then slammed Big Boy back in!

Another 4 inches slid in! I fucked my ass with short, powerful strokes, fucking myself deeper and deeper. Eventually I felt my fingers touch the rim of my asshole, which was now stretched tightly around the dildo. My cock was about to explode and I was starting to feel dizzy, drunk from the pleasure of railing my hole! Rhythmically, I pulled the entire length out and slammed it all the way back in, over and over again, savoring the delightful sensation. In a moment of utter lust and pleasure, I arched my back and came hands free! Cum pooled underneath me as I kept pounding my ass, squeezing every last drop of cum from my balls, shooting stream after stream into the already pre-cum soaked towel beneath me! When I finally stopped cumming, my dick now merely dribbling out the last few drops of cum left in my aching balls, I fell forward, feeling the sticky white liquid spread onto my belly. I lay there, eyes closed, just enjoying the aftershocks of my mind shattering orgasm as the dildo slowly slid out of my ass.

I got up, cum spread all over my crotch and stomach, legs weak from the waves of shivering orgasms they had endured and the harsh punishment my ass had taken. After a warm shower and some cleaning up I went to bed, finally satisfied. Little did I know that my actions hadn't gone unnoticed. I slept soundly, unaware of the small, blinking red light in the top corner of the living room...

Thank you all for reading my first story. If you'd like me to continue with a part two just leave a comment.

Love you all!