[long read] I [22M] unexpectedly lost my virginity to a gay man [35M], and I liked it

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To give a bit of context : I grew up as a socially awkward boy in the countryside, and went to a catholic school. I never had a girlfriend, never had sex, not even a kiss, nothing. The concept of having sex with a man also never crossed my mind, no one in my immediate environment was openly gay, and the word "gay" itself was (is?) mostly used as an insult. Moving out of my parents' house to live alone a big city fixed most of my personal problems, but finding a partner was still one of them.

I'm still not an outgoing guy, not interested in activities that would make me meet people, and all the girls at my university are either taken or not interested in finding a partner at all. Yes, I tried Tinder, but it sucked, as it does for most people.

At 21 during the lockdown at the very beginning of the pandemic and shit out of luck, I decided to get naughty on the internet, in places where people actually want you to get naughty (so no dick picks in girls' DMs, never sink that low people). I signed up on a couple of nude sharing websites, took a couple of pics showing my nude body in various glorious poses, including a couple of hard dick close-ups for good measure, uploaded them all and waited, not knowing how people would react to them. Remember that at this point, nobody had seen me fully naked since the day I was able to take showers on my own, so I really had no idea.

What followed was a TORRENT of comments and private messages of people who all replied ultra positively to my pictures. In the span of a couple of minutes, it felt like I had turned from someone nobody wanted to the most prized sexual object on the Internet. I felt the adrenaline rush from knowing hundreds and maybe thousands of people were enjoying watching my body right now, and most of them made it very clear that they wanted to fuck me. I could NOT believe it. I felt wanted, finally. I went to sleep with the idea that I would probably not die a virgin. It made my year tbh.

But there was a problem : out of the couple of hundreds of messages and comments I got, I could not find a single woman. All of them were from gay/bi men. Now don't get me wrong, I've never been really homophobic, but because of my upbringing, I wasn't ready to be approached by men. I never thought I would be approached by so many at the same time either. Some of them were bottoms and wanted to ride me, others were tops and wanted to pound me. All of the sudden I had to learn how to communicate with lgbt men sexually, to understand and make myself understood, something I never cared about before. I didn't want to simply reject them, I loved the attention too much and didn't want to throw it all away. I loved it so much in fact, that I started imagining what having sex with a man would be like. (just in case, right? it's still sex after all)

I watched gay porn, found some I could totally fap to (which was new), found some in which I would have liked to participate, went through the profiles of the guys who approached me.. "oh I'd totally fuck this one, nice thicc ass, oh wow that's a dick, I wonder how it would feel like inside my.." you get the idea, I found stuff I didn't know I liked and really opened up. I'm most definitely not gay, not really bi either, I just happen to want sex so bad that I'm ready to go curious and have some with men, but for example I wouldn't date a man. It's all strictly sexual.

I continued flirting with guys online because of the lockdown, I didn't want to go too crazy too fast. When the lockdown was lifted, I started asking out the ones I really liked. They all knew I was a virgin and they all wanted to be my first. I made sure to talk to them a lot before we would see each other IRL, so some of them were cool, some of them were creepy and I pulled the plug, and in the end the ones who could have come all chickened out at the last minute. I didn't meet anyone from the hundreds of messages I got. Well shit. I kinda expected it because of course, people tend to be bolder online than they are in real life. I ended up deleting my accounts on all the websites I posted on and just lived for the next few months with these memories.

March 2021, I turn 22. I am once again considering installing Tinder, knowing damn well I will probably not find anyone on there. "Lol, let's try Grindr instead, men love me". I wasn't keen about putting my face as a profile picture, I never showed it to anyone online to avoid being recognized, but fuck it, I will delete my profile in a few hours anyway. I download Grindr and set up my profile, and I am instantly weirded out by the fact that I actually get to see men's faces before I see their dicks. Yep, that's how I know I'm definitely not gay. I get about 20 new messages in a few minutes, I start actual conversations with people, share a couple of nudes, it feels a lot more serious than the websites I used to post on, but I'm still not expecting much.

That's when Jean comes in. (not his true name). Jean goes straight for it : he sends me 3 pics, one with his pants down and his junk hanging out, one of his beautiful thicc ass covered in a tribal tattoo, and another of his welcoming face including a sweet smile. He asks "you want me ?". Oh yeah, I wanted it all. Remember I installed the app only about 15 minutes ago at this point. He looks different, he looks like he actually wants to meet me. I ask him to confirm that he is real, as I was tired of bots and wasting my time with other guys. He proceeds to totally and reliably confirm his identity and location. Holy shit, this might be the guy. I'm getting nervous, I'm trying to keep my cool, not fuck it up, not get sucked into something fishy. I make it clear that I only want sex, and he does as well.

He wants me to come see him at his barber shop in the center of the town, right now. He wants to be my first. He's a bottom, he'll close everything and we'll fuck in the back shop. He is indeed at the barber shop right now, I verified it all with his pictures and Google Maps. I tell him that I prefer waiting until tomorrow (lockdown at 6 PM and it was already 4:45 or so), he tells me don't worry, I'll treat you as an employee and you won't get caught. I insist, just so I can process what is happening, to get my head straight. It's okay, we'll meet tomorrow afternoon.

Fast forward tomorrow afternoon, it's Thursday the 25th of March. This is it, I'm ready. I pick up a couple of condoms I bought a month ago, which I didn't think I'd get to use before the expiration date, and I go out. I've got the barber shop's location on my phone, I'm walking. It's only about a kilometer away from my apartment. I see the shop, I see him inside on his phone, waiting for me. I enter the shop. He walks up to me and tells me "don't, go back out and around and I'll open the back door for you, there are cameras here". He warned me about these cameras in a message while I was coming, but I didn't see it. He's actually an employee but he works alone. I wait at the door, he opens it, drags me into the back shop and closes every door in the way. It's quite cramped in there, there's a lot of noise from people talking and walking up and down the stairs to their appartments above us, not very comfy.

-Now, this is the part you've been waiting for-

We look at each other in the eyes, he starts breathing heavily and touching me. "You're so beautiful" I had no idea of what to say or do, so I just say "thank you" with a nervous smile. He says "can I kiss you ?" to which I also nervously answer "haha I don't know !". He then starts taking off all his clothes, oh my god someone is getting naked for me on purpose ! He then gets on his knees, pulls my pants down to reveal my semi-hard dick, and he takes it in his mouth and starts sucking hard. Oh wow, that's how it feels. Here I am, watching a 35 years old man nude and on his knees for me, and my cock is in his mouth. I'm concentrating on my cockhead, I feel the wetness of his mouth, the sucking pulling my whole dick inside him, his tongue running around it tasting me, he even deep-throats me a couple of times. I'm in total disbelief. "I love your cock !" he says as he gets back up, and closer to me. We're basically hugging at this point, except he is slowly jerking me off and kissing me in the neck. I didn't use my hands at all at this point, this is how clueless I was. He takes my hand and puts it on his dick, which I start jerking in the same manner. He's absolutely rock hard. Me, I had trouble keeping it up. The stress of the first time got to me for sure, and the uncomfy environment wasn't helping at all. I tried my best all along to keep it semi-hard. He asks me again if we can kiss, to which I agree because even though I said I didn't know, I wanted to. Funny note : I got my first blowjob before my first kiss.

Turns out I love kissing. This is definitely the part in which you feel the most loved. There's something special about two sets of lips encountering each other. We're both doing the same thing, we're kissing each other, we're sharing. After a couple of kisses, he even throws his tongue into the mix. I answer by bringing mine to the party as well. We're French kissing, and I actually feel myself getting harder for that than when he was sucking me off. After about 5 minutes, we stop and I ask him if I can suck his dick. He accepts, and I get down on my knees to do my part.

I see this around 6" meaty junk I had seen in the pictures yesterday, now rock hard and aiming straight towards my face. I put my hand at its base to support it, and start licking the head. It's so smooth ! Still nervous and now going way outside of my comfort zone, I take it in my mouth and start sucking. My mouth is quite small, so it's actually quite hard to suck when the cock doesn't leave any space for air ! But the smoothness of the head and the warmth of the shaft, wow. I quickly gave up trying to perform a blowjob like the one I had just received, so I concentrated on tasting it all instead. He put his hands on my head and guided me for a while, until I decided to stand back up and get back to kissing. He then asked me if I wanted to touch his ass, yes for sure !

I had never touched someone else's ass before. It's so incredibly smooth. He asked me if I wanted to bone him, I said yes, he said well start taking the condom out while I'm sucking you off. We did exactly that, but I was nervous seeing I still couldn't get very hard. I put the condom on, he turned around, spit on his hand and rubbed his asshole and leaned forward, I got in position and tried to push it in.. No luck. I try again, nope still won't enter. He takes my dick and tries to guide it, still didn't work, and then it got soft.. I couldn't do it. I didn't know how to feel at that moment. I knew that the first time rarely goes as planned, but still, dammit. He brushed it off, no big deal, it apparently took him until his 3rd or 4th time to get hard. We decided to finish ourselves by hand, and I would cum on his torso. He went back on his knees to suck the shit out of me, and then I followed by jerking myself and cumming all over him, while he did the same to himself. He cleaned himself and we dressed back up, he went back into the shop by the inside door while I went back around. We talked a little bit, he wanted to reassure me that I was really good and he would love to see me again, and when customers started coming back, I left and went home.

We met again 5 days later in the same place, same process, except this time I was more confident and determined. This time around I had less problems getting hard as I knew what to expect, I also finally started using my hands and being more dominant, albeit still careful, so as to not cross any boundaries. He loved it. We did the same stuff as before, we shared kisses, blowjobs, grabbing each other's asses and generally feeling each other a lot more. And then came the test. This time I was hard, and the satisfaction of seeing my dick hard alone made me even harder. My dick is 7.5" FYI. I put on the condom, he leaned forward with his ass lubed up and ready to take me, I placed myself and pushed it in.. I'll never forget the guy's face as he looked at me, right as I could feel my cock pushing his inside walls away. We both instantly started sweating profusely. I didn't know what to do, should I start pounding him like there's no tomorrow, or should take it slow and progressive ? I was at the risk of losing my erection while inside him, so I had to choose fast. I chose the slow route. I thrusted it back and forth slowly inside him, while admiring the view of his round butt cheeks covered in a tribal tattoo, gently slapping on my pelvis. He looked at me every once in a while, with his face completely red and his mouth wide open.

We were both equally impressed with my stamina. We had sex for something like 20 minutes with no end in sight, before we had to stop as he had ignored a suspicious amount of phone calls in the shop while we were at it. (remember, he's an employee and his boss can see the cameras). Sure enough, his boss called him but only once and it was about some file he sent him, the rest were clients. I suspected that the years of masturbation I had been through were the cause of this unexpected stamina, and that it could be a problem if I actually wanted to cum (death-grip syndrome ?) I didn't feel much while I was inside him, apart from the warmth, sometimes I could feel my head being squished and it was awesome, but it was obvious that in order to cum, I had to fuck faster than I did. We talked again in the shop before going, and this time he told me that I was extremely good at it and we HAD to meet at my place, so we could finally fuck properly ! I went home with a big (invisible, because of my mask) smile on my face and a Chad-like walking posture, and realized only when I arrived at my place that I walked an entire kilometer in the city with my zipper still open. Woops.. I hope the customers waiting at the door didn't notice..

Two months later in May, it happened. I gave him my address, he came to my place, and finally, we could play on the bed. The biggest problem before was the environment, we couldn't do anything but standing doggystyle and I always feared that someone would hear us, would walk in on us, or his boss would figure stuff out. This time, none of that would bother us. Safe to say my erection problems completely evaporated. We tried some new positions, missionary, 69, cowgirl (he would bounce up and down on me), and the last one, the reverse cowgirl. This one I couldn't handle, as he blocked my legs and rubbed his ass against me with my cock inside.. I had about 3 seconds in total to let him know that it was coming and BAM ! The Consecration. I came inside him. He looked at me, smiled, turned around, sat next to me and we started kissing again. After about 10 minutes, I said that I was ready for round two if he wanted so, and we went back at it again, this time in doggystyle. After 10 minutes he couldn't hold it and he came on the bed. I tried to cum again as well but it was difficult to achieve after cumming not too long ago, so he told me to lay down, and he would finger my prostate and kiss me at the same time. He slowly slid two fingers in my ass and I felt a pleasing burning sensation as his two fingers rubbed against my prostate, it didn't take me too long to shoot my load again.

We took our time after that to get clean and talk before he left, it's been a little over 2 months and I can't wait to see him again. I move back into my parents' house for the summer so I have to wait. There's such a good mutual understanding between us, and we are into the same stuff so there's no real risk of crossing boundaries. We are planning to try some other stuff next time, like him cumming inside my mouth, or even him penetrating me. He encourages me to try to meet other men on Grindr, but I haven't yet found someone who seemed as trustworthy as he is. Back when I was a touch starved horny teenager, I didn't think my first time would be with a man. I would have probably hated the idea, but now that it's done, honestly I don't regret it at all. A very cool experience all-around. Thank you for reading my story !

submitted by /u/BicuriousNiceDude
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