This is a story about one of the hottest, yet strangest, sexual encounters I’ve ever had. To this day I still occasionally wake up rock hard in the middle of the night thinking about it.
It happened a few years ago when we were all in our late twenties. We were five friends going out for dinner downtown one night, meeting at a married couples house for drinks beforehand. The other two guests were “John”, a single straight guy driving in from out of town for the weekend, and “Annie”, a single girl friend driving in from the suburbs.
We had all known each other since we worked together in our teens and had not caught up in a while. I had always had a little crush on John and would blatantly objectify him, he played along gamely like he did with his bro friends and their homoerotic banter. The running joke was that he had sex with or dated most of my girl friends… which is actually very accurate. He’s never had any problems scoring with women, and gays were always attracted to him.
John is a very charming guy, about 5’9 like me, with big blue eyes, dirty blonde hair and a ruggedly handsome face. He’s always been in good shape without being huge, consistently going to the gym and maintaining nice arms and pecs. Reviews of his sexual prowesses were always extremely positive, one friend who dated him for a little while raved about the wild sex they would have. I always wanted to get into his pants but knew he was super straight.
At dinner we shared a few dozen oysters, multiple wine bottles and a few rounds of shots. It was a really fun time, and, predictably enough the married couple went home after dinner, leaving us three singletons to continue the night with some bar hopping. And yes, we got really fucking drunk.
They obviously couldn’t drive home so I told Annie and John they could crash at my place. We took an Uber there and we smoked a joint and had another drink before going to sleep. I lived by myself but didn’t have a guest room, so we had to figure out some sort of sleeping arrangement for three people. We decided it made the most sense for Annie to share the bed with me and for John to take the sofa in my office. We drunkenly stripped down to our underwear and went to bed.
A few minutes later, John got up and came into the bedroom and said “Fuck I can’t sleep on that sofa it’s too small, make room for me”. He proceeded to get on the bed and snuck in under the covers between the two of us. I had a queen sized bed at the time , so he fit but we were definitely shoulder to shoulder, I thought it was weird but didn’t mind having his warm body close to me. I closed my eyes again telling myself this is going to be uncomfortable but oh well, it was a really funny end of night.
But the evening was about to get really confusing and much more fun.I was laying on my back, trying to sleep when there was rustling in the bed. I figured they were both trying to get comfortable. Then I realized John was turned towards Annie and I was hearing kissing sounds.What the fuck.Stoned panic was kicking in. Do I say something? Do I leave the room and let them do their thing? Were they flirting all night and I simply missed it? Should I have let them have the bed from the get go? How could I possibly have misread the evening to such an extent. I was so confused.
Not a single word was ever said for the rest of the night.
And then as they were still making out and I was planning my exit, the situation changed drastically. John reached behind behind him and grabbed my hand, placing it on his hip.I froze.Was this really happening?
I squeezed his ass and he responded by arching his back and pushing it towards me. I turned over towards him and ran my hand up his back and placed my other hand on his right hip, grinding my crotch onto his rear. My cock was getting hard really fast against his muscular hockey butt, my briefs and his boxers keeping us contained for the moment.
I could feel the length of his body against mine as I leaned in to kiss his shoulders, the crook of his neck. He smelled warm and manly, with a hint of tequila.He was still grabbing Annie’s tits when he turned his head towards mine, opened his lips and kissed me. I was in shock that all this was actually happening, that one of my best straight guy friends was instigating this wild threesome scenario. Don’t get me wrong, I would have gotten down on my knees to suck him off instantly had he ever asked me to. But I also had no interest in exploring the feminine mystique … I am really, really gay. Thankfully, somehow, Annie and I never had actual contact during this adventure, it’s as if we were both having our own intercourse with John. I guess this speaks to his sexual talents?
As I kissed him I reached up to his muscular, hairy pecs then ran my hand down his abs to his crotch. I finally got to touch what I had been practically begging to see for years. Through the fabric of his boxer briefs I grabbed his rock hard cock and he responded by thrusting his pelvis into my hand. From what my friends had told me over the years I was expecting a really big cock, but it was actually fairly similar to my own. About 6” and cut, maybe a bit thicker than mine. I always say my dick isn’t huge but that it is very pretty, I would say exactly the same about his. A nice mouthful but not scary in any way. I think gay men probably have much “bigger” expectations when it comes to cocks and tend to be size queens. Women complement a dick that is used well, and he is definitely talented.
We took off our underwear and at that point I was still unsure how this was going to play out, was I supposed to just give him attention and not expect anything in return? I would have gladly submitted to that, but he surprised me by reaching for my cock. He grabbed it confidently and started jerking me off as I lay on my back. Annie started going down on him and he guided the back of her head with his right arm and placed his left behind my shoulders, leaning in to make out with me again.
When she came up for air he let go of my cock and I took it as a signal to have my turn tasting him. As they made out I moved down the bed to be between his legs and grabbed the base of his dick. It was really beautiful, rock hard and straight with a slight curve towards his stomach, the head throbbing pink. He’s a pretty hairy guy but keeps things nicely manicured, his pubes were trimmed short and his big balls were almost smooth. I started by licking the soft spot under the head, and then sucked on the tip, twisting my tongue around it. I took all of him in my mouth in one shot, it was already wet from Annie’s work there. His cock filled me up completely to the point just before where I would gag. It was perfect.
I sucked his cock for a while, really fucking loving it. I ran my tongue up and down the tender urethra and around the head, my saliva was leaking down his heavy balls and I made my way down there. Despite their hefty size I managed to cram them both in my mouth, sucking on them and pressing my thumb right under them. He seemed to really love that… I came up for air a bit and then sucked down his cock again, using my tongue to extract some sweet pre cum that was already leaking out. I looked up his muscular body and saw that Annie was literally sitting on his face getting eaten out. He smacked her ass a couple times and she turned around, noticing I was looking up, and we wordlessly shuffled around to take on new positions.
Moving back up to the top of the bed I lay back on the pillows, John leaned in to kiss me again with his firm, manly mouth. Fuck he was a good kisser, I loved the feeling of his rough stubble on my lips. He then kissed Annie, and turned back towards me, grabbing my throbbing cock. I still wasn’t sure how far he would take things… but he went there. He was hesitant at first, but he approached my dick slowly and opened his mouth, licking the tip. I was captivated, my dick was pulsating it was so hard, here was about to go down on me.
We made eye contact as he slowly swallowed me whole, taking in all six inches of me. He quickly pulled it out, I though “oh shit he’s backing down now and regretting this whole thing”, but he didn’t. John grabbed both my balls in his hand and the base of my dick, and took it in slowly again. He was getting used to having a penis in his mouth for the first time, and from what I’ve heard from the (many) first timers that experimented with me, my dick is the perfect introductory size.
(Side-note: since this adventure I basically fetishize bi guys, nothing turns me on more than sucking the dick of a guy who also likes women)
Like all first timers he was a little toothy at the beginning, but he quickly adjusted his technique. I was in ecstasy feeling his mouth on me, my hands were playing with his soft blond hair, and then I grabbed his head and guided his rhythm up and down my shaft. He was taking it like a champ, sometimes gagging a little but he kept going at it. My balls and ass were shaved smooth so he had easy access to everything. John also imitated what I did to him and licked and sucked on my balls. Mine are definitely smaller than his so easy to take in. The thought that such a manly man was sucking on my testicles was insane, and then he surprised me again and he lifted my hips up and went to my hole. His strong tongue lashed at my tight pink hole, his years of expert pussy eating were evident. He didn’t stay down there too long unfortunately, and redirected his attentions towards Annie.
Honestly I had no clue what she was doing while he was going down on me, so I guess it was her turn to be serviced. She was on her back with her knees bent, and he was on all fours at the bottom of the bed, voraciously eating her pussy out. I could see his beautiful ass from my vantage point next to Annie and I couldn’t resist, so I got up and went behind John, grabbing his hips. He surprised me once again, fully thrusting his juicy ass into my crotch, which I took as permission to continue. I slid my hard cock up and down his furry ass crack, feeling the soft hairs and sweat.
I then got on my knees on the floor and started kissing his ass cheeks, making my way to his sweet hole. I licked it and it tasted a little salty from the sweat, and his body once again immediately responded to my touch pushing himself into my face. I ate his ass out like I have rarely eaten ass before, usually preferring to be the recipient. I was in heaven, tasting this handsome mans most vulnerable spot, using all the force my tongue could muster and tried to burrow my face as deep as possible inside him. I loosened his tight hole, digging in to the sweet spot. I ate him out as he simultaneously ate out Annie, getting his ass completely drenched.
Then I got up again and put my dick on his wet crack, using my own spit and his sweat to jerk myself, simulating fucking him. He also seemed to love that … responding to every thrust in kind. I kept going for a while, then I went back to eating his hole, which was nicely dilated now. I pressed my cock onto it and he pushed back, trying to enter him, but after a few tries it was clear that more work and lube would be needed, and I don’t think we were ready for that. If it was just the two of us I would have loved to explore entering his hole and taking his virginity… nothing would have made me hornier. But we were in an awkward threesome situation and communication was not exactly happening.
I went back up on the bed, still raging hard. John is obviously a man that likes to please, hence his being so popular with all the ladies, so he returned his attention to me. He went for my cock with his mouth again, this time really going for it and applying suction and his tongue to it. I was almost delirious at this point, and I needed the release of an orgasm.
John was almost agressive in the way he sucked me off, I was holding the back of his head but he was going at his own rhythm. I started to tense up, my ass muscles flexed, and my moans were clearly indicating that I was close. He kept going at it and my hard cock was buried deep in his throat when I started to cum. At first, instinctively, he tried to back off but I put my second hand on his head and held him in place, basically forcing him to swallow it all. He didn’t fight it and dutifully took it in, then he looked up at me and I must say that FUCK he looked so hot. My straight friend just swallowed my load. I could die happy now (or be cursed to fantasize about it for the rest of my life…).
At this point I was spent. It must have been like 4am, the booze and the weed suddenly rushed back to my head as I lay my head back on a pillow. John kissed me again, then he took Annie by her hand and went into my office next to the bedroom and proceeded to fuck her. I found that to be strangely considerate? Like my fantasy would have been to be the one getting a pounding but this scenario did not allow for it, at least I didn’t have to watch them do that. They came back to the bedroom, got into bed with John in the middle, and he kissed me goodnight. We then passed the fuck out, naked, exhausted, and spooning.
The next morning we got out of bed, looked at each other and proceeded to laugh our asses off. I don’t think this was on anybody’s vision board for our night out on the town. I offered to order us some McDonald’s to help with the hangover and they both agreed emphatically. I then drove them back to their cars and they went home.
Needless to say this was one of the most exhilarating experiences of my life, literally getting to fulfill a longing I had had since I was 17 when I met John working at a coffee shop. Obviously this was not the exact fantasy I had in my head… I never would have dreamed of including Annie or any woman in this… but it was fucking hot anyways.
It has been over three years since it happened, and amazingly enough we are still all friends in the way you stay friends with people once you are in your 30s: we don’t talk often, but if we see each other it is always with a big smile.Annie has banned me of ever mentioning it again, and reminds me of the policy when we travel together (to be fair, people outside our circle would probably be mortified, and I do love to shock people when I am drunk… and her boyfriend probably wouldn’t think I am an inoffensive gay man if he knew).
John finds it absolutely hilarious and basically trolls me with sexual tension when I see him, he knows I would get down on my knees and suck him off instantly if he asked. Fun fact: he is the only person who knows I write these stories.
The funny thing is that since then, I have actually fantasized about having a MMF threesome and interacting with the female. But only with the guidance of a guy I trust, and with a girl that I absolutely do not know and will never see again. I am legitimately curious what a pussy feels like, but since I am 100% a homo I would need a man to keep me hard. Maybe my next adventure will make me lose my lady virginity?