A Straight Man and Gay Sex
I’ve mentioned before that I occasionally like to be with a man sexually. I’m not interested in emotional or romantic relationships with men, but I find the touch of a man to be thrilling and unique. It’s the feeling of being desired in a way that straight men aren’t used to experiencing.
My hookups early on were facilitated by the M2M section of CraigsList. I’ll say that normally, I’d be the first to try something like Grindr but I try to limit how out there I am with my sexuality. Besides, not all people can reconcile that a partner is bisexual.
My first experience was with a guy that seemed to fit the bill. With men, I kiss, enjoy nipple play, giving and receiving head, and getting fucked safely. He hosted and when I arrived, he let me in while he was on the phone. I got the feeling he was the caretaker of, or otherwise living with, an older relative. He guided me to a bedroom adorned with tchotchkes. As he continued to talk on the phone, I got restless and decided to just go for it. I undressed in front of him then unzipped his jeans to release his hardening cock. His cock wasn’t huge, but it seemed to my untrained eye that it would be more than adequate. I put my mouth on the head then began to lick and suck. I was surprised by the spongy feel; I really liked the way it felt in my mouth. Soft and hard at the same time. I looked up and heard him say, “I have to go.” He hung up the phone and started to undress. I helped him out of his t-shirt when I spotted the barbells through his nipples; I couldn’t help but to start licking and sucking them. He smelled like Irish Spring bath soap. We kissed, then he lowered me to my knees and started fucking my mouth. Since this was my first time sucking a cock, I gagged on it some but he was the perfect size. I enjoyed feeling his hardness in my mouth, anticipating his orgasm. After a few minutes, he lead me to the bed where he laid down and asked me to straddle his chest. Then he placed my cock in his mouth while he jerked himself off. I tried to reach back to help out, but he pushed my had away. He sucked me until I was about to cum; he pointed on his chest where he wanted me to cum.
For a first time, I was a little disappointed. I felt more like a masturbatory aid than a lover. I didn’t get to check off some of the boxes I was looking for: swallowing cum, and getting fucked. But I enjoyed it enough to seek out another experience. At this point I want to call out that arranging a hookup with a guy on CL shouldn’t be that hard…but it is. It may take at least ten responses before I connect with one person who is serious and not just collecting dick pics then it could take a while before we meet. So for those responding to a CL for M2M hookups, I have a few tips. In the first email, give stats, status, likes and dislikes, availability and ability to host. Include a picture if you’re so inclined but it should not take 15 emails to connect in the real world.
The next meaningful encounter was with another CL hookup. When L arrived at my loft, I let him in. He looked around and commented on the space. I lead him upstairs to my bedroom that I had prepared for us. We had been sexting all morning, and one thing I knew for sure was that I was going to get fucked by a man for the first time that day. I kissed L and let him explore my mouth with his tongue. His kiss was smoky with a hint of mint. He took off his shirt, and we continued to make out, all the while I stroked his hardening cock through his pants. He rolled over on top of me and started to suck and bite my nipples; I was squirming and moaning with desire. Finally, L stood up out of the bed and took off his remaining clothes. In our texts, L sent me a photo of his cock in comparison to a Coke can, he must have sent me the wrong photos. His cock wasn’t too big; a perfect size if you asked me. I sucked his cock hard while he fucked my mouth. I could tell my technique had improved by the way L pulled away and ordered me onto the bed on all fours. I have to admit that I kinda like being submissive to a man. I felt his lubed finger penetrate my ass. “You’re very tight, try to relax,” he said then I felt the head of his cock touching my anus and trying to push past. After a minute or two he was inside me, it was a whirlwind of sensation. L began to gently slide his cock back and forth, getting me used to the sensation of being fucked. “How’re you doing, you ok?” I nodded that I was and managed to get out the words, “please fuck me.”
L took me on a tour of anal ecstasy. He had me on all fours, then he fucked me missionary style before bringing me to the edge of the bed so that he could fucking me standing while holding my legs up so that he could get maximum penetration. The waves of delight were unlike anything I’d experienced before. I could tell he was getting ready to cum and grabbed his waist with my legs and pulled him deep into my ass so that I could feel his cock throb and convulse. At this point, I hadn’t cum and was having too much fun. I took the condom off his cock and sucked it clean so that I could taste his cum. I also wanted him to get hard again so he could fuck me more. Lo and behold the second coming, his cock stiffened in my mouth. “I want more,” I said. L gave me a bewildered look but settled in for the ride. I laid him down on the bed and mounted his cock. His cock slid in effortlessly now that it had been relaxed after a good fucking. I rode him while stroking my cock. His hands guided my hips up and down. Finally, I came and not just a little with a geyser of semen shooting from my cock. “Thanks for the shower,” L said wryly. I could tell he was pleased with himself; I was too. I was having so much fun if another guy had been there, I’d have sucked him off and fucked him too.
These are two of the more positive experiences I’ve had hooking up with men for M2M fun. However, that’s after going through a lot of flakes and fakes. I guess there are more men who’re curious and will flirt via email but disappear when it’s time for the rubber to hit the road. Anyway I’m hoping for more positive interactions in the future. I’m talking to a guy who seems to perfectly fit my bill. We’re in to the same things (in a complimentary way), he respects my situation regarding chastity and is willing to host. In fact, I get the feeling that he’ll give me what I need in the way of dominant male partner…fingers crossed.
