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By my first year of college, I had been dressing secretly almost every night for close to 7 years. I had stopped, purged, and restarted a few times – usually I stopped dressing whenever I had a girlfriend I was fucking. Ever since I began dressing, my late nights in my room would be consumed with dressing in my collection of lingerie and working myself into a frenzy with a dildo until I came. I would repeat over and over u til I was spent and fell asleep. Sometimes I wouldn’t get out of my nightie before falling asleep and I would wake up with a start, wearing lingerie with my ass gaping and sore and late for school or work.
On occasion, my friends would get me to go out to a bar or just to go somewhere outside of the city to drink and smoking weed on the tailgate of a pickup truck somewhere, just being guys. I could play that side of my life just as well.
One night we all went to a popular club in town and drank our share of nickel beers. We were pretty drunk when we ran into a guy who asked if we wanted to go to a party he and his roommates were having. This guy was a real country boy, he had the hat, the boots, and everything. All night he was drinking Jack and Coke, so we kept calling him Jack. After a bit of cruising the club, we figured what the hell, should be some girls at Jack’s party and they had more beer. We got in our cars and followed Jack way out of town to a townhouse in the burbs. As soon as we arrived we could tell this party was not happening. They did have more to drink but the only people there where Jack, his two guy roommates, and one of the roommates sister. The guys all took their chances trying to hook up with the sister; but it just wasn’t happening. Meanwhile, I was at the kitchen table playing quarters with Jack and one of his roommates when an unexpected bet got thrown down.
If the roommate made the next shot I had to kiss the Jack. The roommate sinks the shot, I look around for my buddies, and then I lean over the table and kiss Jack. Nothing much just a regular kiss. After a few more rounds at quarters, I hit the restroom and then head over to a table in the corner of the kitchen where the whiskey and mixers were. I’m mixing a drink when Jack comes up behind me and starts kissing me on the neck. He reaches around and starts rubbing my cock through my jeans, then leans around and gives me a good deep French kiss. Just then one of my buddies rounds the corner Pendik Esmer Escort as says it’s time to go. I could tell he thought he might have seen something strange going on; but just wasn’t sure what. Jack tried to get us all to stay and then tried to get me to stay behind; but it wasn’t happening. My friends dropped me off at my house and everyone went their separate ways heading home for the night.
Honestly, that was my first kiss with a man and my head was spinning. I couldn’t stop thinking about it.on the ride home I had made up my mind. As soon as I got inside the house I grabbed a duffel bag and threw some of my clothes in it. I went to the bathroom and cleaned up my downstairs and grabbed my car keys. I memorized every turn on the way back, so I knew exactly where to go.
I showed up at the door to the townhouse and the roommate from the quarters game (Kyle) yelled back, “Hey Jack, look who showed up”. I came inside and Jack came up to me and gave me another deep kiss. I told him I needed to get changed then I pulled out the first thing in my bag – a black satin teddy – and said simply “I dress”. Jack and the Kyle looked slightly disappointed; but shrugged and said “well, bathrooms over there”. I went into the bathroom and pulled on the satin teddy but I had forgotten stockings or garters. My legs were hairy from the upper thigh down but I generally kept my face, chest, balls, and asshole cleanly shaven. I grabbed one of the guys razor and went to work on my legs and underarms (I was desperate). I had remembered to bring shoes, a little makeup, and a cheap blonde party wig. After I was as smooth as I could get, I put on a little lipstick and the party wig then slipped on a pair of red heels from my bag and walked out.
I had been dressing for some time now but still had a little trouble walking in heels. I teetered a bit. I move toward the liquor table as the eyes followed me across the room. Kyle was obviously no longer interested in me but Jack was – and now the other roommate (Andre) had a big smile on his face. Andre was a large guy, like large tall built guy; but also a little chubby. In the brief conversations we had I found out that he played football. Andre needed to take his sister home, so he left me there with Jack and Kyle. Before long I found myself sitting on the couch between Jack and Kyle, in a teddy and high heels, watching a movie. Jack made the Pendik Eve Gelen Escort first move and leaned over to kiss me. We kissed deep for what seemed like a long time and during this my cock came untucked from behind the thin, snap crotch of the teddy and balls and all flipped out the side. It was a very unladylike showing.
While Jack and I were kissing, he unzipped and took my hand and placed it on his bare cock. I’d never touched a cock other than my own. It was a little exciting but oddly not that big of a deal – it was a bit like holding my own. We kept kissing and I feel Jack’s hand slide up to the back of my head and begin pushing my head down to is chest. I knew where this was going but I had never sucked a cock before. I placed the soft tip of Jack’s cock in my mouth and moved my tongue around it – sort of like sucking on a lifesaver. His hands kept lightly pushing my head deeper and deeper onto his cock until I realized I had the whole thing in my mouth. I started slowly sliding my mouth up and down the shaft taking Jack’s cock deeper and deeper until it was just at the edge of my throat. I had moved up onto my knees on the couch with my ass partly in the air and the whole time I could feel Kyle rubbing my smooth legs, up and down, from my thigh to the back of my knees, getting closer and closer to my cock each time.
Not having any blowjob experience, I was moving very slowly up and down Jack’s cock and it was taking a while to get him going. I felt fingers fiddling with the snaps on the crotch of my teddy and then suddenly a snap as the crotch gave way and came undone. I kept slowly bobbing up and down on Jack’s cocking could hear his breathing getting deeper. Having been the receiver of a few blowjobs I knew what that meant. I kept bobbing and tried to add a little sucking pressure but that caused Jack to shift around, so maybe I did it wrong. Now I could feel fingers tracing my asshole. I heard the sound of a bottle cap popping and then felt the finger again but this time wet and slick – Kyle was lubing my ass! The fingers slid into my ass and I could feel the thickness of the knuckles. I’m sure Kyle was surprised at how easy it was to get his fingers in – I had been using rather hefty dildos for years but never had a real cock, so I was only technically a virgin. He didn’t seem to care and slid what may have been three fingers into my ass as far as they would Pendik Evi Olan Escort go.
The extra attention didn’t completely register and I was focused on my first blowjob and what to do next. I could hear Jack’s breathing getting deeper and I moved my hand down to his balls. As soon as I touched his balls he jerked and I could feel his cock jerking in my mouth and between my lips. A flood of warm cum hit the back of my throat and my gag reflex started to kick in. I quickly swallowed and it stung the back of my throat. I could still feel Jack’s cock jerking in my mouth but there was no more flood of cum, so I stayed there with my mouth fully over Jack’s cock. His hands were on the back of my head pushing down slightly on his cock and I could feel two hands placed on my ribs and slide down to my hips. I could feel the hands pull back slightly on my hips as a decent sized cock pushed into my asshole. I lifted my head from Jack’s lap to look behind and saw it was Andre and not Kyle. Andre had an above average cock, it didn’t have a lot of girth – or at least not more than my dildo – but it was a bit long.
Andre started out slow and pushed deeper and deeper into me. Whenever he got the full length of his cock inside it seemed to hit the end of my ass and I felt an uncomfortable pressure each time. I don’t think I made a sound at all – no moans, certainly no dirty talk, just maybe a little heavy breathing. Andre kept working up to a rhythm where he would pull almost entirely out of my ass and then plunge deeper. At one point I put my hand back to slow him down as each time he was hitting that uncomfortable spot deep in my ass. He kept his big hands firmly around my waist and kept rhythmically pulling my hips toward him and pushing deep into my ass. At one point he placed one of his large hands on my shoulder and pulled me back toward him, arching my back, and then suddenly he gripped my waist and pulled my shoulders back hard and drove his cock deep into my ass directly on that pressure point. I realized he was coming and I just froze. He held me there for what seemed like a few minutes and then let go of my shoulder and slid his cock out entirely. I slowly rolled over to sit on the couch and just stared straight ahead at the television. I remember. Saturday Night Live was on.
Jack hung around for a bit longer to talk but Andre went to his room almost immediately. After a short time I went to the bathroom and got changed back into my street clothes and drove home. Andre didn’t wear a condom so I was leaking his cum out of my ass the entire next day, and my guts deep down were pretty sore. I never heard from Andre or Kyle again but I did hear from Jack and we hooked up one more time.
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