I'm sorry for the length, I started typing and got a little carried away.
This is is a semi-second hand story from a guy I hook up with:
Growing up, he was the epitome of a straight guy—a basketball player in peak physical shape, standing 6'4" and 230lbs of rippling muscle. He was a total ladies' man, absolute girl crazy pussy slayer always chasing girls and living the life. In his mid-to-late 20s, he had an old high school friend he'd go out with to hit the clubs and pick up women.
One night, after years of friendship, his friend confessed something unexpected: even though he still liked women, he had fantasies about *him*. It was late, they were both pretty drunk, and he brushed it off, sending his friend home without another word. They never spoke of it But curiosity eventually got the better of him. One day, he invited the same friend over, and that's when he got his first blowjob from a guy. I’m not sure how many times it happened, but it never went much further than him being on the receiving end . Over time, the friendship fell apart-likely because of his friend's attempts to escalate things-and they lost contact.
Fast forward to his early 30s: he's married with two kids but secretly experimenting on Grindr with a blank profile, mostly meeting trans women. That's when he met me. It's been almost four years since we started seeing each other. At first, it was just kissing (which felt boring, to be honest), but liked watching him use the safe space I gave him to test his own boundaries & eventually, we progressed to him giving me oral.
Then, he let me touch his ass and rub my fingers around his hole (I wasn’t allowed to finger him yet)-but just as i was getting hopeful he disappeared for months. Out of the blue, he came back and asked if I'd be willing to take things further. Of course, I said yes-l'd been ready since day one. He flaked so much after that out of anxiety I guess it was a full three months before I saw him again and finally topped him. The first time we had sex, l wrapped up, but it was so incredible that I immediately went on PrEP the following week. It was transcendent-like nothing I'd ever experienced before. I've had my fair share of conquests , but this was different. I'd never had sex before where it felt like we stopped being two separate people; even at times, it was as if we'd switched bodies when we got bored of being one melded pile of flesh with one mind. The passion was unmatched. Over the years, l've watched him transform from someone who was just curious to an outright demonically voracious bottom. He just takes and takes all nine inches of me, always wanting more.
In the time we’ve known each other, his marriage ended, he went through a string of girlfriends, so our relationship has had its ebbs and flows.Sometimes we'd hook up once or twice a month; other times, when he’s single, we'll see each other multiple times a week-or even multiple times a day. I'm completely addicted; I can't get enough of him, he says I'm the only person he bottoms for.Looking back, I'm grateful to his old friend for having the courage to confess his feelings. That moment set him on a path that eventually led him to me—and to owning my dick.
This next one is an ongoing exploration that I feel will end up turning a fully straight friend of mine out and giving him HIS bi awakening:
I’m a pretty decent Muay Thai/kickboxer, training six days a week, sometimes twice a day. Being around other strong, in-shape, and dangerous men is something I’ve grown accustomed to—a far cry from my early teens as a scrawny, socially awkward kid afraid of my own shadow. Now that I’ve grown into my own, I still struggle to recognize cues if a guy isn’t direct enough. One of my training partners, let’s call him H, is someone I’ve known for a few years. We spend a lot of time together. He’s straight, handsome, and in incredible shape (he had a girlfriend when we met and still has one now). Honestly, I’m perfectly content being platonic friends with him—I genuinely don’t see him that way. But recently, every couple of months, we end up in ridiculously homoerotically charged situations, and they keeps escalating.
It started one day after training when we were bored and decided to do shrooms. That led to us giving each other massages in his bedroom, which soon became a regular thing, even when we were sober. At first, I didn’t think much of it—until one day, we were the only ones left in the gym after sparring. In the showers, I heard him ask, “Hey! Think you could help me get my back? I just want to make sure I’m extra clean.”
He knows I’m into men, so even though my mind went *???*, I gave in and started sudsing him up, working from the nape of his neck down to the small of his back. I went up and down a few times before it dawned on me that this might be his way of inviting me to experiment. Just to cover my bases before touching his butt, I asked, “Did you want me to do JUST your back?” My mistake, he laughed and said, “What do you think this is? Fuck outta here!” Then he whipped the curtain shut and joked about fulfilling my “Make-A-Wish” for the year. I was confused, so the next time we hung out, I brought it up: “If that was an invitation, cool. If it wasn’t, also cool! But don’t poke fun after creating a gay situation for us.” He said it wasn’t an invite and that he’s strictly into women. I dropped it and never brought it up again.
Fast forward two months, and he ends up spending the night at my place. He mentions having back pain, and I offer to help. I grab some almond oil and get to work, massaging his neck, shoulders, lats, middle, and lower back. I ask him to tug the band of his shorts down so I can get to the dimples above his butt. Without hesitation, he pulls his shorts halfway down, and I’m surprised by how aroused I’m getting. I move to his feet, calves, and thighs, then ask, “Can you move the shorts a bit? They’re in the way.” Off they go—he’s fully naked, lying facedown with his legs spread. I spend the next half hour gliding my hands up and down his body, from his feet to his head and back, slyly spreading his cheeks to get a glimpse of his hole. He doesn’t stop me. When I flip him over to do his front, he pulls his shorts up to cover his dick, but I still slide my hands under (for lymphatic massage, of course

) and graze his balls and tip a few times, even rubbing down from his cest to the base of his shaft. He murmurs that I'm the only guy he'd let do this without getting violent, because he feels safe with me. When I’m done, he’s so happy he buys me breakfast the next morning.
I’m not sure when it’ll happen again, but the next time we end up in a porno-like situation, I’m definitely touching on his hole and hoping for the best.