I still think about an “arrangement” I had with a friend I made through work. Although thinking back to it— one of my first same sex escapades— has become more infrequent since it happened two years ago, the memories still get me harder than any other of my sexual experiences. But, unfortunately, I’m finding the details of what began a few years ago are beginning to fade, so it’s for that reason that I’m writing this, my first gone wild story.
At 22 I graduated college and moved to New York. I didn’t really have any plans but I liked art so I figured that I would try to work in art galleries while I figured out whatever my life was going to be. The type of self discovery I was planning on doing during this time was only having fun in my youth with friends and figuring out maybe what I wanted to do more long term. This is to say that I was NOT planning on doing any sexual discovery. To the outside world- even if I worked in art- I was a straight guy. I had always seen women. My kind of gender role was jock/dumb guy.
But, this isn’t to say that I never thought about men. While I would say my base sexuality in terms of watching porn always has skewed heavily toward women, toward Reilly Reid anal videos or Sara jay getting fucked deep by some stud or mompov, in my teens I added a heathy dose of trans porn to my routine. I lived to find new Bailey Jay and Sarina Valentina videos. Soon this built out into watching Venus Lux top and reading gay first time erotica. I’m sure one type of attraction to these videos was the sense that a taboo was being broken. That I was watching something new and risqué. But more so the attraction was intuitive— the type of reaction I had to them was so much more emotionally vivid. When I would watch Bailey Jay top Bee Armitage I could feel a burning deep in the pit of stomach that would extend down so I could feel the ring of my asshole pulsating. A butterfly type feeling of sheer horniess that was unmatched by anything else in my life.
So anyway, I’m an ostensibly straight guy working for an art gallery in Manhattans UES. The place I work isn’t a titan of the art world but it is very hip and gets written up all the time. When we would have openings, usually about 50% of the crowd were regulars— people would knew the owners/gallerists and did business with them regularly. I dreaded these openings because socially I can be very awkward and, also like a pretentious art school kid myself, I always found the society types of a UES art show to be so boring.
Quickly after a few of these things I found one regular I actually enjoyed taking to. His name was Jules, he was 25, and my read on him was always that he was a rich kid who kind of understood how that was perceived so he always wanted to downplay his privilege in order to be seen for his own personality. He always was a kind of jeans and blazer type c-suite aspiring guy. Anyway he regularly bought work from my boss and was always around so we interacted frequently. Being cool, we became quick friends and every once in a while would grab lunch if he was around the gallery in the afternoon. Soon, convenient lunches became hanging out on weekends and meeting each other’s friends.
Jules wasn’t hot but he wasn’t unattractive. He was like 5 foot 8, maybe 150 pounds, cute-ish in the face, and, again, had a kind of hip but tailored look- horned rim glasses, nice designer jeans, blazers, that type of stuff. I, on the other hand, had a bit of a stranger look— I was 6 flat, 190 pounds, and had a very dark complexion— dark hair, hazel eyes, olive skin, always light bearded, and hairy. I wasn’t super “fit” But I wasn’t fat. I was thick in that I was muscular but had a little gut. Now, what made me turns heads was that I’m very cute in the face. So while I wasn’t everyone’s cup of tea, I knew there were people who I turned on— and I KNEW Jules was the type of person that I turned on. I could see it from the way his eyes lingered on me, from the way he thought everything I said was interesting or laughed too hard at my jokes. What gave it away even more tho was, when we’d see each other out, he do little things like touch my back while we were ordering drinks or always ask “where the next party was” during closing time like he was throwing a conservative Hail Mary- tonight would be the night I let him take me home.
So my second summer out in NY. I had gotten a job interview with a very cool gallery to help run a pop up thing they were going to be doing in the Hamptons. Anyway I was talking about it one afternoon at work with the other gallery workers when Julien walked in— he chatted us all up, but of course was most interested in hearing what was up with his boy me so of course I told him that I had this interview next week and I was going to need to take the LIRR during the day and come back. He told me good luck and went on with whatever he was there to do. No big deal!
Later that night, I got a text from Jules. We texted frequently so this wasn’t weird or anything. It was just a simple text asking me what day again my interview was in the Hamptons. I quickly responded “Thursday” to which he immediately responded that his family had a place out there and that if I didn’t want to make the long train ride out there for only an afternoon I should stay at his place that weekend. He said not to worry about anything because he was friends out to his family’s spot all the time. This sounded great and I agreed.
The week of the interview finally came. The only communication I had with Jules was about when I should meet him at the station, there was no like “pack something cute winky face” type shit. This was just two boys going to have a fun weekend.
Anyway we get out there and I immediately go to my interview. Jules agrees to take my stuff to his place, and tells me he’ll pack me up at the gallery when I’m done. The interview goes whatever— not good, not bad, just average enough that I don’t want to think about it. Jules picks me up in a Benz wagon (of course this is his family’s “beach” car) and we head back to his place.
When we get there it’s beautiful- 4 brs, giant main floor, pool and it’s on the water. Every time a wealthy friend had invited me out to his beach house it was kind of like a dinner party, maybe someone else I knew was going also but it would be like the parents have a friend out and each kid has a friend out. Big happy time. Anyway, when we get to the beach house no one is home. I asked if anyone else is coming and Jules smirks back “no, we have the place all to ourselves.”
“Jules!” I chuckled to myself. I never thought he was going to have the courage to try anything but this was clearly the weekend he was going to try and get in the pants of his crush.
I wasn’t mad, I didn’t think I had been played, but it wasn’t also like I had an immediate boner. When he said we had the place to ourselves, I immediately had this feeling that by the time I took a train back to New York City, I probably will have fucked him.
What’s important here though is that I had never even kissed another guy, let alone let one pop my ass. So, with me being unsure, i thought it was going to be important for Jules to be very slow on how he was seductive. Really warm me up so I was ready to take the plunge. That being said, for one of the first time in my life I really felt like the pursued- and it turned me on. I felt the power of having this guy my wrapped around my finger, dying to let me embrace him.
Anyway, that stuff about needing a long seduction period— that was kind of wrong. We didn’t exactly jump into fucking and sucking, but it became clearer pretty fast I think to Jules that he was going to get what we wanted.
After saying we were there alone Jules quickly broken the tension by saying “let me show you around.” The tour of the place of course ended upstairs where he showed me my room. He told me he would be satiating in his parents room- the master suite. We chit chatted at he made some excuse like his parents had to do something else last minute blah blah blah. Sure man whatever. When we walked in his parents room it was massive- big king bed with all white sheets and comforter except sitting at the end of the bed all neatly folded on the end was what he had packed for the weekend. We talked about fashion regularly and had gone shopping before so I didn’t feel weird immediately flipping through what He had packed. It was all nice stuff- Alexander McQueen tees, APC jeans, etc. But in the bottom, the most colorful entries in the collection, what I found was a number of jock straps he had packed.
When I picked it up I let it dangle from from one finger like I wasn’t impressed or grossed out by it. He laughed and said “yeah, well, you know, when in rome” before asking me if I had ever worn one. My response was “I think you know I haven’t,” to which he laughed and replied “well you’re missing out, they make guys look super hot, and as your friend if you wanted to try one on and see how you looked, I could tell you honestly if it was for you or not.” “Oh you could? Could you?” I shot back sarcastically. Honestly, I was surprised how smooth Jules line was, so with the jock dangling from my finger, and my sarcastic tone still hanging in the air I walked slowly toward the bathroom.
Once I closed the bathroom door I did think about immediately coming out and pretending it was a joke. My feeling was that I was afraid doing this now would deter Jules advances. I wanted this. I wanted this to happen. So I dropped my clothes and put on a black jock with a gold band. As a hairy guy I thought the black complimented me. Again, I’m bigger than Jules by a few inches and pounds so the thing was TIGHT on my body. But I knew I looked good naked it was just a matter of how the jock fit.
I was semi hard when I dropped my pants and by the time the material of the jock touched my body I was 100% big vein pulsating full mast. I knew I couldn’t walk out there with a full on hard on. First, the jock was small so it couldn’t cover my dick. Second, I wanted to be soft when he saw me in it because I didn’t want to relinquish my position as the pursued. I didn’t want him to know full on I wanted this. I wanted the doubt to linger in his mind that, at the last second, I might deny him what he’s wanted all these months we knew each other. Basically, I wanted to tease him.
So, I flicked my nuts hard enough for the hardon to disappear and I walked out. I was met with mock oohs and ahhs. While I knew I was hot, the jock didn’t fit really as I planned. I figured I would looks like a thick girl in booty shorts in it. That I would be busting out of it in all the right ways. Instead, I was only busting out it— I thought it was I’ll fitting and not sexy. Jules being the ever honest friend told me he didn’t think it fitted. “I know black is “your look” but that’s an old one,” handing me a red jock now he said “this one is I think one size bigger.” I snapped the red jock out of his hand and spun around so that my front was out of view of Jules hungry eyes. I dropped the black jock bending over and giving him a view of my ass before quickly pulling the jock up around me.
This one fit much better. Jules proclaimed “I think we have a fit! Now, if you’re feeling hot, and I think you are, let’s go to the pool.” He told me to meet him down there and scurried off.
As I laid in a pool chair, he emerged in a yellow jock. This is the first time I saw his body like this. He was slight but not overly small or large. He was a twink with brown hair in a stylist at the time undercut, a tiny bit of stubble, hairless body, and a modest bulge. He had a fair skin color, the type that only gets a faint tan even if you work really hard— and Jules worked really hard on it. He came ready to lay out with his bottle of tanning oil and lotion.
As he applied lotion to his body we chatted about the bars and restaurants around and what to do this weekend. It was more a friends vibe with the of course “we’re going to fuck” thing pulsing under the surface.
While this was happening I flipped from sitting up on the chair to having my head at the toe, laying on my stomach, with my bare ass now floating in the air. Not breaking conversation and with a sense that I didn’t want to watch Jules reaction and give away the game, I stole a quick glance and could see his eyes focused on the uncovered thickness still jiggling in the air.
I Knew what was coming with me in this position. It was going to be the corniest like possible- “do you want me to rub oil on your back.” I had a perfect idea to speed things along. See, maybe the nerves had started to get to me, maybe it was the excitement of finally getting to have my first gay hookup, maybe it was how much he wanted me, maybe it was how good I knew I looked, and maybe it was all these things together but right now laying on my stomach I had a massive erection. So, when Jules finally did hit me with that “do you want me to run oil on your back?” I knew exactly what to do. “No…” standing up I got in my chair sitting up/laying on my back again, I was very careful standing up to keep my boner from popping out of the strap so instead now the head remained hidden. “…why don’t I sit with my back out of the sun and you use that oil to jerk me off.” Jule bit off even more than I asked for because he immediately got up, slung his body over mine to straddle me and started making out.
After about a minute he pulled away and said with a sly smile “I’m sorry I gotta see this thing because if you haven’t been able to tell, I’ve been curious about it for a while.” He move to the foot of the chair and grabbed my jock to pull it down, sprinting free my rock hard cock
I was blessed with a very good if not great cock. It’s a nice pink color, big slightly darker head, cut, a shade over 7.5”, thick, a gentle curve to it, and I always keep a nice little thicker of dark pubes around the base. On first view he gripped it, said “I should have known” leaned in to shove his tongue down my throat, before pulling back to pull his jock aside and start frotting us.
His cock was smaller. It was probably about 5”, average thickness, and much darker than the rest of his pale body. He was totally clean downstairs, which as I write this out today, for the first time I realize this fucker probably got waxed like right before the trip. Later in our relationship I would tease him that he had a “nice starter cock. A good beginning place before I ultimately move up to bigger and blacker things.” (Idk if this teasing (in the future) got him so hot bc of the challenge or because of the mental image it created of me stuffed with a black cock but it brought something out of him but that’s all for a different story).
I laying back with legs open, him sitting between mine stroking and gyrating his hips— almost as if he was simulating what may come later, him topping me. It felt so so so good. That feeling that I mentioned earlier? That warmth I only felt deep in the pit of my stomach and around the ring of my anus and that only arose when I was watching gay porn? It was more intense right now than it had ever been. I felt so overwhelmed that I didn’t know if I was going to puke or pass out. Every few minutes he would take the bottle of oil and pour an excessive amount on our cocks.
Eventually he Said “it looks like you might need a little extra attention,” and started stroking me with both hands. As soon as he took me in both hands I let go a very big and a very feminine moan. As soon as it left my lips I paired it with a theatrical deep breathing to signal how hot being touched made me.
I looked him right in the eyes and said “please make me cum baby I want you to bring me there. I’m so hot right now Im going to explode and I want you to see me shoot all over myself.” The next few strokes felt like an eternity but I was whimpering “please daddy I want it please please.” I don’t know if I was getting close but I really really wanted it, I don’t know if I could have cum, I might have been to overwhelmed, but before I even got the chance, Jules cut off his stroking, leaned in to kiss me. Pulling back he told me he wants my first load in a different way, and he hopes I understood.
Sorry this ran so long guys, this is just part 1 of what turned out to be a very long weekend, and also a very long kind of Odyssey into same sex and group sex. If you enjoyed this story, please drop me a line and I’ll keep writing for you guys! Thanks!!
Source: reddit.com/r/gonewildstories/comments/k8k3lp/my_weekend_with_jules_m_bicurious_straight_guy
Hot!
Would love to hear what came next!