[MM] – Popping the cherry. My first time with a man.

Well, it was shortly after I broke up with my first ever girlfriend. I was 22, eager and adventurous and always a bit into men. I never knew what exactly it was, I wasn’t into male on male blowjobs or into anything romantic with them. But as I am more of a boyish guy, with little self-confidence when it comes to being dominant and manly, I always adored looking at strong males. Alpha types, muscular, self-confident, knowing what they want. I also always loved cocks.

So, after some struggles I finally convinced myself to go on Tinder and put my search for males only. It went as I thought, when I wasn’t horny I wasn’t that much into your average guy, until I found him. The perfect one. He was so very attractive, swiss guy, brown to blackish, tall and super fit. I couldn’t believe what happened when I saw him, as he turned me on. I swiped right and couldn’t believe it again when I saw that we matched up. Well, there you go, first gay match.

We chatted it up a bit, I was very direct and honest with him, told him that I was new to this, inexperienced, recently broke up with a girl, yadda yadda. He was super interested and nice about all of it, super open to my stories and wishes and told me he wasn’t looking for a relationship either, he was into girls for that. So we agreed to meet up and talk there.

First time meeting was great, we met in public and had some fun chats, then went to something more private, still in the public though and talked some more intimate things. He asked me if I was ready and wanted to come to his place and I was surprised but figured I wouldn’t do it if I didn’t right now, so I agreed.

So, we got to his place, real nice one, rooftop, great view around the city. Really looked like a business man place, I felt mega comfortable. He opened a bottle of wine, we had a glass or two and talked on his couch. He then, after some getting closer, just leaned over and started kissing me.

Albeit I said I am not into kissing other men, that changed when he just did it. It felt right, not THAT different from kissing girls, but it definitely felt different to be kissed and not be kissing. I loved the feeling of submission, of letting go for someone. He did quick work, some kissing, some fondling and then undressed me to the point where I was completly naked on his couch. He was very nice and gentle about it, then picked me up. I am about 192 cm, so a guy picking me up made me feel real fucking weird. I felt like a girl, like I was 20cm shorter and lighter and it felt real weird but mega hot. I think I was rock hard already there.

He carried me to his bedroom and put me on his bed, told me to get on all fours, starting playing with my butt, slapped me and jerked me. He then started rimming me. It all felt so very mega intense. He got out some lube and started rubbing it all over me, pulled out a plug and slowly inserted it. It felt so ultra weird, very…filling, very spreading and a bit painful. But my horniness and the lube helped.

He then told me to turn around. He had already taken off his clothes while he was working me, only in his tight boxers now. His dark skin and athletic build were so very much more manly than my pale, average body. I felt mega attracted to him. He told me to get on my knees. I did like he said, fell in front of him, while he sat down on the bed. He reassured me of everything, told me to just say if something wasn’t quite right.

He then pulled down his boxers, revealed a beautiful, 8 inch, nice and girthy dick. He was made from the gods really, and I loved it. He told me to do it, like i like it. And then, seconds later, I found myself with a black cock inside of my mouth, struggling to keep it all in. He had a cupboard with a mirror attached to it in his bedroom. I once looked to the left to see myself like that and felt my cock twitching. I felt like a faggot, and I loved it.

After sucking him off for quite a while and feeling him get more and more erect in my mouth, which was a very good feeling to me, I felt like I did a good job, telling by his moans and him laying on his back and just relaxing. He grabbed my head one time and pressed me deeper onto himself. I think he didn’t really realize, or maybe he did, that I just loved him overpowering me so freaking much. I never have a hard cock while I eat out a girl because most of the time I focus so much, I lose the erotic aspect of it but during that, I was constantly hard.

He told me to stop after a while, pulled me up and we kissed for a bit. I felt his cock touch mine, and I felt the energy running through it. It almost felt like cumming already, I was so excited by all of it.

He put me on all fours again, face facing towards the wall and his damn cupboard. He pulled out the plug, slowly, and I couldn’t believe that feeling. While pushing it in felt somehow painful, pulling it out felt…mega good. Like it felt like heaven. So much good feelings ran through me. I moaned, I think. He gave me a slap and told me that’s good, because obviously I was into it. He told me that even though now I was spread a bit, I was still mega tight and he was kinda big, so he would go slow, but it would hurt. I should tell him when it was too much.

He then leaned over me, and I felt his cock touch my asshole. I think I was never as nervous as I was in this moment. I had white spots in front of my eyes, my arms were twitching and I was sweating all over. I felt him above me, felt so vulnerable and so very gay, it was so powerful to me. Splitsecond later, I felt like my ass was being torn apart. He entered, lubed up from my spit and the lube and just pushed. I cried out loud, dropped on my face and he immediately started comforting me.

“It’s just the first half right now.” He said and we both laughed. He pulled out and I moaned again, now from the good feeling. It took a while, minutes. I don’t know how long exactly, but long but in the end suddenly I felt his tummy pressed against my butt. He was completly inside of me.

It felt amazing. Like I was so very spread out, so very filled, so…in my place. I was still rock hard. He told me that was super hot to him, because most guys go flaccid during anal and he found a hard cock mega sexy. We then started to find a rhythm.

So, in other words. He started having sex with me. I felt his motion and the constant change of pain-good-pain-good started to change into less pain and more good feelings. It was awesome. I loved the whole scenery around it, I loved hearing him moan, grabbing my butt, I loved him pushing into me. I looked up after a while, and straight into the mirror.

To this day, I still can see that picture. Me, on all fours, so very helpless and vulnerable and that tower of a man above me, his face focused, sweaty and pounding away at me. Whenever I am in situations where I have to be manly, I remember that picture and it turns me on.

In fact it turned me on so much in that situation,that suddenly I felt the feeling of an orgasm. But it was different than usual. While usually it feels like an eruption of sorts, where the cum pumps and then cums out in a bunch, this felt like I was orgasming without cumming. Like it just felt incredibly good. I was quivering and moaning and said “I…am cumming…I think?” And he just laughed and told me that yes, I was, a bit already. And I looked down and just saw that mess I was making. The cum was just running out of me like a river. No contractions really, just very small ones, but an endless feeling of “good”.

That seemed to had motivated him, as he now picked up the tempo and started to go real fast while grabbing me. Just as it was getting too much again and the pain started taking over, he suddenly stopped and pressed real deep. And then he came. He just pulsated inside of me. I was so very overpowered by all of that. The feeling of him cumming, his moans, his sweaty grab, the smell of both our perfumes, my cum and the sweat, the heat and the knowledge that a man was cumming into me was so much for me, that my arms broke away to the side again, I dropped on the bed and came a second time.

Source: reddit.com/r/gonewildstories/comments/ssm335/mm_popping_the_cherry_my_first_time_with_a_man