This is my story about my first homosexual encounter.
I was a troublesome teenager, booted out of my moms house when I was 18 for being a wildchild. I had problems with authority and was always getting into trouble with the law. After getting the boot I lived at a downtown shelter for homeless youth. It was a filthy 3 story building where you slept with the light on to keep the cockroaches at bay.
One evening while roaming the downtown core with a two of my pals an older gentleman approached us, his name was Allen he was about 55 yrs old and asked if we would like to come to his place for a party, he offered free hash and beer, that was enough for us to respond with a hearty yes!
The three of us piled into his car and headed out for a night of getting wasted.
We arrived at the mans beautiful cottage a short time later, myself and my buddies were excited for the chance to get plastered and party all night for free!
At the time I was maybe 5’9 135lbs, with long blond hair and had very feminine looks. My friends were a few years older and they shared a tiny bachelor apartment just outside of the downtown core. We drove for about 45 mins to a rural lake area where Allen’s cottage was located.
We partied like rockstars until well after midnight, drinking beer and doing hot knives with hash, smoking a few joints and tequila shots, Allen did not consume very much booze he just toked and sipped a few beer, then the expected happened as all both of my friends got so wasted they were ready to pass out and acting stupid, I being the lightweight of the group drank much slower than they did (no Tequila for me 🤢) and was feeling good but not nearly as wasted as my two pals were. I always preferred a few tokes over alcohol at that age as booze seemed to knock me on my ass.
Allen then offered to drive everyone home at that time and so off we went back to the city stopping twice during the commute to let my pals get sick on the roadside.
Allen dropped my friends off first at there apartment and then was driving me back to the shelter, he asked if I was still up for a few drinks and or toked and offered his couch for the night if I wanted, and said he couldn’t imagine having to sleeping in a shelter. I graciously accepted as a couch with a fireplace nearby was a big upgrade from a cot in a dorm where the cockroaches and filth covered every wall.
We got back to Allen’s cottage about 2 o’clock A.M, it had been awhile since my last drink or toke so I was relatively sober as was Allen. He grabbed us a beer out of the fridge and we started sharing stories and puffed a joint, I was on the couch and he was in the Lazyboy. I hadn’t sat in front of many fireplaces and the flames mesmerized me as the hashish took its effect. Allen told me this was his cottage and he had an apartment just east of the city so he stayed here once or twice a week since his divorce. I told him stories about the ‘street life’ and he stated that was no life for any person.
We sipped beer and toked until 3-4 A.M and I was getting a strong buzz and getting sleepy, I told Allen this and he got me a blanket and pillow out of a chest near the door. We finished our final beer and Allen headed to the bathroom, he must have had a good buzz as well as he simply pissed with the door wide open and I could see him from the sofa, he brushed his teeth, turned off the lights and headed into his room while I got cozy on the couch, staring into the fireplace was very relaxing and I could feel my eyelids getting heavy, I took off my hoodie and jeans and got comfortable the couch.
I was awoken a little while later when I heard Allen get up to get a glass of water, upon opening my eyes I could see his silhouette in the kitchen area, he was totally nude and had a semi erection, I paid no attention and closed my eyes again as this wasn’t the first time I had seen a guy nude, I played alot of sports in school when I bothered to show up and had seen plenty of guys showering. I woke up again and due to the beers I had earlier my bladder was about to burst, so I got up walked to the bathroom and did my business, on the way back to the couch I heard Allen call my name, I looked into his room and said ”what’s up”? He said if the couch was uncomfortable I was more than welcome to sleep in his huge bed, he was just laying there with the blankets pulled back to reveal his nakedness a semi hard cock.
I was speechless, I politely declined and headed back to the couch.
My mind was racing, did he just hit on me or was it my imagination? Was it just the dope? There was no way he was gay was there? I couldn’t just leave as I was 25 miles away from town!
I could not sleep after this happened so I sat there in my boxers and t-shirt replaying the events in my head.
Allen walked back out of his room a few minutes later, this time he was wearing boxers, he sat down and old me he was sorry if he spooked me, he explained he was bisexual and was just innocently flirting and maybe it was the booze talking, he also said he expected nothing from me and to just enjoy a good nights rest, he told me if I was interested he only wanted to give me a blowjob and if I changed my mind his door was open, he returned to his room and my mind started racing again….
My fears were now confirmed, Allen was trying to get me to go bed with him, I had been with a few girls prior to this, I was still a virgin but had fooled around with plenty of girls my age, but I had never even considered the thought of being with another male.
There was no way I could sleep now, I was worried if I fell asleep Allen might make a move on me, I pictured him sneaking out of his room and trying to suck my cock while I slept, for some reason the more I ran that scenario through my head the more detail I added, I kept picturing myself waking up and my hard cock being sucked by him, then something happened, my cock started to actually get hard thinking about it, the more I tried to push the thoughts away the more vivid the thoughts became.
Being a younger male it didn’t take much for me to get an erection, and in no time I had a full fledged hard on.
This was too strange for me to comprehend, I sat up and lit a smoke watching the flames in the fireplace dancing but I still could not stop running scenarios through my head of Allen trying something on me.
I finished my smoke and my dick was still kind of hard, I peeked over at Allen’s room and his light was out so I started to slowly jerk my cock figuring there was no point in wasting a perfectly good hard on!
I replayed images of making out with girls in my head all while slow massaging my cock and balls, but every so often those thoughts of me waking up with my cock in Allen’s mouth crept back in, I was getting worried, was I gay too? Was this normal?
I laid there for about thirty minutes just massaging myself, my cock was getting very close to exploding, but the closer I came to cumming the weirder my thoughts became, I wondered what it would feel like having another guy suck my cock, would it feel the same as a girl?
I had never received a blowjob before so I really had no evidence for the argument, other thoughts crossed my mind like would Allen try to fuck me too? Would he want me to touch his dick as well?
Would he tell anyone?
I almost slapped myself, as the more I asked these questions the more curious I became about the answers.
Was I really thinking about making out with a guy? Why was my cock getting so hard thinking about it?
Enough! I told myself, I kept repeating in my head that ‘I am not gay’ and I tucked my cock back into my boxers before I came.
I got up and went to grab a glass of water, and passed Allen’s room yet again, he was sleeping and his nakedness was on full display, he had a large cock compared to mine and was in very good shape, my eyes took note of his bare chest, and muscled abdomen “what would it be like” I asked myself, feeling another males body next to mine, would he be rough or gentle? I guess my presence at the door woke him up as his eyes fluttered open and he smiled at me!
He asked if I had reconsidered his offer earlier that night, I said no very quickly in a hushed tone. Then Allen said to me “well it looks like something did” and pointed at my crotch, I looked down to discover that while staring at him sleeping I was again getting hard, my dick was making a tent in my boxers and there was no way to hide it, I was half erect and red with embarrassment!
I abruptly turned away and headed back to the sofa, a minute later Allen came out and sat beside me, I was distraught with nervousness but Allen was very understanding, he said he wasn’t going to force me into doing anything I wasn’t comfortable with which was a huge relief.
Allen sat up, he was wearing boxers and rolled up a hash joint, we smoked it and talked about the experiences we both had pertaining to sex. He explained he had only been with men since he got divorced and I told him I had never been laid.
I got pretty baked off the joint and started to feel more relaxed with Allen, he asked if I liked porn movies (what teenaged guy didn’t) I said yes and he turned on the VCR and TV, picked out a movie and pressed play, it was a scene with a sexy milf and a guy, the woman was hot and she was working the guys dick with her hand and mouth, Allen said it was okay if I wanted to jerk off a little while watching it, I resisted that idea not wanting this to go much further.
On the TV another guy entered the scene and the milf proceeded to suck them both for awhile before one guy started fucking her doggie style while she sucked the other, the guy receiving the blowjob then stood up and made his way towards her ass, all of a sudden the guy fucking her was giving the other guy a blowjob while pounding away at this milfs pussy, I was rock hard by now and Allen must have noticed, “you like that scene” he asked, I was shy in answering ‘a little’…..I watched with morbid curiosity as the scene unfolded into a full on bisexual scene, everyone got sucked and fucked, I tried to hide my fascination but my cock was having none of it, I reached down and adjusted my hard dick and noticed Allen was now hard as well, I watched the movie as the milf and one guy sucked the others cock, then one guy started riding the others cock as the milf sucked his dick, they then proceeded to cum on each others clocks and the milf cleaned them both up rather nicely.
I was so horny I almost forgot Allen was sitting next to me, he had no doubt noticed my erection by now, then it happened, Allen reached over and placed his hand just above my knee, I quickly pulled away just as the next scene in the movie came.
Allen again apologized, but this time I said it was okay that I was just nervous as hell, he giggled and I sat back down on the sofa. Allen then said it would be fine if I wanted to masturbate while watching the movie, the scene had now become two men and a woman wearing a strap on dildo, she was eagerly sucking the two guys, I said fuck it and let my hand slide under my boxers feeling my already rock hard dick, I slowly played and when I looked at Allen he was also masturbating, I pulled my cock out of my boxers in the front and so did he, we watched while the woman sucked and then SHE fucked both men the ass with the strap on, sometimes she sucked on one while fucking the other, and sometimes the two guys took a turns sucking while they were being strap on fucked.
I glanced down and noticed my cock was dripping precum, I looked over and so was Allen, his cock was much bigger than mine, well trimmed, circumcised and maybe six or seven inches long, mine was about five inches, maybe.
Allen asked if I had ever gotten a blowjob, I responded no, he asked if it looked like something I would enjoy, and I said yeah I guess. Allen then asked me to stand up, I fiddled with my hard dick and then stood up, he said to move a little closer, I did, now knowing what he was going to do, he took my cock into his hand started to slowly jerk me off, I was in heaven, it felt incredible he then guided my already rock hard cock into his mouth, it was very warm and he just held it there between his lips, I though of pulling away but it felt so good, he began slowly sliding my cock in and out of his mouth, I thought I was going to cum right there and then.
After about two minutes Allen also stood up, he wasn’t a big man maybe 6’2 200lbs but I felt very small beside him, he grabbed some more blankets and made a little bed on the floor in front of the fireplace, he asked me if this was 100% okay with me and I just nodded yes. I sat down beside him on the blankets and he stroked me and then took me into his mouth again, I could still see the TV and the woman was now fucking one guy while the other jerked off nearby, as Allen was licking and sucking me I let my hand slide down onto his thigh, this made him suck me even deeper, the deeper he went the higher my hand went until I brushed his balls with my fingers, I gently grabbed his very hard cock and started to stroke him while he sucked me. I was just about to blow my load when he stopped, he watched me jerk his cock and I could feel his dick growing even more.
Looking back at the TV the two guys were now in a sixty-nine position furiously sucking each other while the woman fucked herself with a toy and watched them, I pointed to the TV and told Allen that I would like to try that so he laid down beside me and took me into his mouth again, in this position Allen’s dick was right in front of my eyes, I touched it, jerked him a little and then leaned in and kissed his cock, this made him start sucking me very eagerly, I decided to dive into this so I opened my mouth and let his manhood slide over my tongue. It felt strange at first, but with better positioning I was soon bobbing up and down on his stiff prick, he deepthroated my cock and I attempted to do the same but gagged, he started to tug on my scrotum and within seconds I could feel my balls tightening up, less than thirty seconds later I was emptying my juices into his open mouth, this sent him over the edge and he started pumping his hips while I gobbled his cock, I heard him whisper “I am going to cum” and laid me back on the blankets, he knelt between my legs and started to stroke himself and me, soon enough he was shooting globs of hot sticky cum all over my cock, when he finished he leaned over and took me into his mouth again and cleaned my softening dick clean.
I got very quiet after this and he cleaned up and shut off the movie, he returned with a beer for each of us which I damn near chugged.
Allen must have noticed how I had quieted down and said he was going to get some rest, I laid awake all night replaying the night in my head.
In the morning he drove me back to the shelter and we barely spoke, I have never seen him again. JJ