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Tripping With A Convict

by Trajan


By Jay Flynn Steve was a 29 year old ex-con I met in Texas when I was 19, going to Tech school. He was about 6'-2' and very butch. He had large muscular build from working out in prison, mostly covered with tattoos of serpents, skulls, barbed wire and the like. His crew cut hair was light brown and he had a mustache like a cop. He looked like a convict, but that rough quality made him pretty hot. He was one bad ass you didn't want to cross, no question about it. He had been convicted of a combination of robbery, firearms, and drug charges and had been a regular in jails and prisons most of his life. He was out on parole in a liberal 80's program that let you out of prison early if you went to school and stayed there crime-free. I knew him from parties at the dorm complex our school ran. He wasn't the type of crowd I normally ran with, but he sold weed making our friendship a necessity. Hanging with him was flirting with the devil, but it was a turn on and he liked me - I always felt safe with him. I had heard him kidding about prison sex a few times and even watched him pretend to rape his roommate James as a joke. I was afraid to ever risk approaching him about having sex; however, just partying with him once in a while was close enough for comfort. One Friday night I was trying to score a joint and went to see him. The dorm complex was pretty dead, everyone seemed to be somewhere else. He was out of weed to sell, but said he would toke his last joint with me. We hung out there getting high watching the tube for a while, but the buzz wore off and we got bored. He asked if I wanted to do some acid with him and I went for it thinking it would be an uncharted adventure to trip with this dude. I was into that stuff for a while in my youth. We did the LSD and spent the better part of the next 9 hours spelunking around the dorm complex and the immediate neighborhood. In the early morning hours we were coming down from the high in a baseball dugout across the street from the dorms, we talked about everything on the face of the earth in explicit detail that happens with acid. It was very cold out so we cuddled up close to each other to keep warm and share the experience of coming down together. He was very quiet and down to earth for a change, unlike the usual tough as nails "bad-ass" he usually presented himself as. I was hornier than hell, and with the buzz, I was willing take a risk. I finally got up the nerve and asked him if he ever got raped in prison. "Me get raped, hell I raped the fuck out those bitches, I never got raped", he bragged. "Did you like it?" I asked. "Fuck, man when you're in the joint, you take what you can get, and take it like a man. It's just fuckin' - don't mean your queer", he said, "Why you asking? Do you want to get fucked up the ass or somethin?" I didn't answer. I didn't have to. When you are tripping acid, you sort of have this sixth sense about things, we both connected. He stood up and unbuttoned his fly, letting out his cock. It was hairy and long with a tattoo of a black snake, coiling around his huge balls and spiraling all the way up his thick shaft with it's eyes and fangs on either lobe at head with its open mouth at his piss hole. This was a trip, but a twisted sort of turn on. I dropped to my knees with my back against the dugout wall and took in his fat snake. He was sweaty and hard, and tasted sweet. He grabbed his hands on the chain link fence above by head and started fucking my face hard, banging my head against the concrete wall. I was trying hard to keep up as he seemed to be racing. "Take my cock bitch!" he repeated, "take it down bitch". He was streaming juices into my throat almost the whole time. I was foaming at the mouth and jacking off. It felt like he was going to smash my head thought the wall with his violent slamming thrusts. I could not get enough of his snake, sucking and slurping. He finally stopped and ordered me face down on the bench, pulling my pants down to my knees with one hand, while he pushed me down with the other. He got down on me and started forcing his cock into my ass. He was pretty rough, and proceeded with no romance or lubrication other than my mouth's moisture. He placed both hands on my back shoulder blades and began fucking me deep and rough. It didn't hurt as much as it should have because LSD has a numbing effect physically, but I could feel wood splinters poking into my chest and stomach as his thrusts scooted me across the bench. He was slapping my ass with his thighs violently, grunting "take it bitch, take it like a man". I was moaning in deep soulful pleasure and pain, howling like a dog at moments. He pulled out for a second wetting his dry cock with spit, and starting in again. He grabbed my hair pulling my head back as he started pumping with a spiritual vengeance, ever harder than before. All the force of his cock's pounding with was transferring back through my scalp and neck. This was the roughest I had ever been reamed and I was loving every second of it. I was getting raped in prison for all intents, screaming and grunting in with every nasty thrust, "yeah bitch, you like that big fat cock up your ass, you fuckin' bitch, fucking little faggot". He yanked back on my hair one last time delivering his load into my beaten hairy hole. The warm juice squirting into me felt heavenly and soothing, loosening him up and relieving the friction. He then laid down on my back continuing to slide his still hard snake in and out, now much more lovingly. He was cuddling like a lover, kissing and tonguing my neck. Acid gives you stamina, and he remained hard for a good ten minutes, pumping my asshole with love letting out repetitive small bursts of warm juices. When he was done we just laid there for a while sweating and kissing as one, and finally got dressed as the sun was coming up. We left the dugout and went to his dorm, having come down from space and back to earth together. Once back to the room, he continued to show me a tender side that I never expected from this ruff ass ex-con. He gave great head and let me ride him hard a few times myself as we went back and forth most of the day in between naps. We never got to together again after that, as he was suspended by the school the following Monday for dealing dope, and was promptly sent back behind bars.

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7 Gay Erotic Stories from Trajan

Framing Men, Part 1

Framing Men, Part I By Jay Flynn I find myself in the best places to observe young hard men on a regular basis--construction sites. These men are modern-day cowboys, rough, dirty, and full spirited, with red-neck bravado. They are a close knit cadre of men, like brothers, but tough to the core. They work and play hard, and most are sexual predators at heart. Many

Framing Men, Part 2

Framing Men, Part II By Jay Flynn Framing Men 2 of 3 Getting another chance to visit the construction site, I was excited about the prospect of more viewing pleasures. There is nothing like the sight of an army of shirtless dudes, sweating in the sun while working hard in their leather boots and 501's. I had to go see the job captain of a particular project and

Framing Men, Part 3

Framing Men 3 By Jay Flynn Framing Men 3 of 3 Returning from my lunchtime venture with Marc and Josh, I was still feeling the stretched and pounded pulse in my ass. No one seemed to notice my arrival and my new shirt I got from Marc, at least not at first. The yellow-green shirt did not match my brown Dockers all too well. I made my way through the unending maze

Helping Thy Neighbor

By Jay Flynn Helping out thy neighbor makes the community a closer and better place for everyone. I spend a lot of time people watching near my home, and enjoy the sights of good looking guys out in their yards or wrenching on their cars. One of my favorite neighbors, Jeff is guy about 27 or so, with short dark hair and mustache. He is tall, and well built, and works as a

My Workout/Fuck Buddy At Last!

I work-out in my garage often with my bench press and a multi-exercise unit - a gym is too much for me. I keep the garage door open part way to let in fresh air and light, although doing so sometimes attracts a neighbor to see what's cooking. I had always covertly hoped it would land me a work-out/fuck buddy. The only person ever indicating interest in even working out was

Thrown A Curve, Part 3

Doug was an adventure closeted as the experience had to be, but we flirted with danger once in a while. Stud-like and daring, he was the type that liked fooling around in the bushes "down by the river" without regard to the risk of getting caught with his pants down. One day I had been hanging with my other friend Rob who was straight, we chased women together a lot. In fact, he

Tripping With A Convict

By Jay Flynn Steve was a 29 year old ex-con I met in Texas when I was 19, going to Tech school. He was about 6'-2' and very butch. He had large muscular build from working out in prison, mostly covered with tattoos of serpents, skulls, barbed wire and the like. His crew cut hair was light brown and he had a mustache like a cop. He looked like a convict, but that rough

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