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How I lost my virginity to a guy

Biboy27

On the Prowl
Joined
Apr 4, 2025
Posts
62
Reaction score
366
Points
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Location
United States
A couple years ago I had my first ever experience, and with a guy none the lest. I think I was 25 at the time. I decided to download Grindr on my phone. Browsing it at 4am I found a guy who was willing to hookup, and he was a short drive away. We exchanged pictures, and he really wanted me to come over. I really wanted to bottom, but he was exclusively a bottom, so I settled with topping. He gave me his address, and told me he would leave a lit candle in certain place easily seen, so I knew I had the right place. I remember trembling with anxiety the whole drive there. But I really just needed someone. At first I couldn't find the place, and was just going to go back home out of my own nervousness, when I spotted the candle shining in the dark. I walked shakily up the drive to the lower door. Creeking it open, across the room I was faced with him bent over on the couch. The room was dark and I could only see his ass. I awkwardly fumbled in the dark for the provided condom and lube. I began to hotdog him for a moment, before I drew back to push in. I didn't quite know what to expect for my first time ever. But after I slipped in, It felt warm, but somehow almost like nothing really. I tired to give him a reach around handjob, but couldn't quite get a good angle/grip I came within a few minutes. In which I pulled out, removed the condom, and awkwardly left back out the way I came. I remember still feeling so kind of shook up after leaving. But years later now. I find myself wanting that again. I tried redownloading Grindr. But I just can't work my nerve up again.
 
A couple years ago I had my first ever experience, and with a guy none the lest. I think I was 25 at the time. I decided to download Grindr on my phone. Browsing it at 4am I found a guy who was willing to hookup, and he was a short drive away. We exchanged pictures, and he really wanted me to come over. I really wanted to bottom, but he was exclusively a bottom, so I settled with topping. He gave me his address, and told me he would leave a lit candle in certain place easily seen, so I knew I had the right place. I remember trembling with anxiety the whole drive there. But I really just needed someone. At first I couldn't find the place, and was just going to go back home out of my own nervousness, when I spotted the candle shining in the dark. I walked shakily up the drive to the lower door. Creeking it open, across the room I was faced with him bent over on the couch. The room was dark and I could only see his ass. I awkwardly fumbled in the dark for the provided condom and lube. I began to hotdog him for a moment, before I drew back to push in. I didn't quite know what to expect for my first time ever. But after I slipped in, It felt warm, but somehow almost like nothing really. I tired to give him a reach around handjob, but couldn't quite get a good angle/grip I came within a few minutes. In which I pulled out, removed the condom, and awkwardly left back out the way I came. I remember still feeling so kind of shook up after leaving. But years later now. I find myself wanting that again. I tried redownloading Grindr. But I just can't work my nerve up again.
Hi BiBoy. It's understandable that you were anxious and felt awkward afterward. Having sex with a random stranger can be nerve racking. Having sex for the first time is a major step in your life, and to do it like you described - no introduction, no foreplay, and I presume you didn't see his face or exchange words - must have taken a lot of courage on your part. I guess this is how he wanted it: anonymous dick, walk in, fuck and leave. Maybe he's a famous senator or something and couldn't show his face. Who knows? The only thing we know, from what you've described, is that he used you for sex and he got what he wanted.

No wonder you felt awkward and shaken afterward. You just had sex for the first time, with an ass up in the air.

I think it's important for you to understand that it doesn't need to be like that. Sure, many of us enjoy hookup sex. Whether guys are finding their way, discovering their sexuality and not sure about being open about it, or just enjoy the thrill of the random encounter - there's a lot to be enjoyed when two guys get together for physical sex. You both want something and you can satisfy each other's wants. If everything's consensual and nobody gets hurt, that's great. Hookups can involve greeting each other, foreplay, enjoying bodies. The sex can be more personal, more relaxed and fun. Hookups can even progress to regular fuck buddies / friends with benefits, where you know each other, you know what makes each other tick, and you care about giving each other enjoyment.

I think if you want it again, you should work towards getting it. I know you haven't asked a specific question, but I'll answer a question you might be asking yourself: How can you work up the nerve again? My suggestion, if I may be so bold, is to forget the idea that sex should be what you described. Sure, you can hook up, but in a more friendly and interpersonal way. Grindr is very much about random sex, as are some of the other apps/websites: I've had mixed success with Squirt, where I've found guys who developed into good fuck-buddies. Chat with them, get to know them a little bit. If you're unsure, ask to meet them in public, say for a coffee. You might consider trying to meet guys in real life through bars or clubs if that's your thing. I understand you're young, finding our about yourself, and might not want to risk being outed; that's understandable. Try to figure out a way to have a better experience than what you described.

Let me say again - what you described was not what many or most people would consider to be good sex, and was not a great experience for you for your first time. Don't use that as a benchmark for what to expect.

If I may give you a couple of bits of advice. One is that if you want a particular thing, say you want to bottom, don't settle on topping just to get an encounter. It's not what you want, so why let yourself be used for your dick.

Another is that bottoming for the first time is a major thing to do. You should be prepared for it, physically and mentally. I suggest not doing it like that guy did, facing an unlocked door with your ass up. If safe sex is your thing (and I suggest it should be) stick to your game plan. Over on the forum "Health and Well-being" is a pinned page "All About Ass". It's worth reading and taking the time to learn about your body.

Another (and I did say a couple of bits of advice, lol, but here's more) - hookup manners. Bring condoms and lube, and a travel-pack of tissues, and a small bag for rubbish which you should clean up afterward. A guy may feel awkward after sex, like you did. Smile and thank him. You both got what you wanted. Always remember that if you're in his home, you're his guest, and behave as such. I'm not suggesting that, when you described removing the condom then leaving, that you left the used condom on his floor. But if someone did that at your place, you might think that was pretty poor form.

Man-sex done right is fun, mutually enjoyable, and need not leave us feeling awkward, shocked, ashamed or confused. Good luck and happy fucking!
 
Hi BiBoy. It's understandable that you were anxious and felt awkward afterward. Having sex with a random stranger can be nerve racking. Having sex for the first time is a major step in your life, and to do it like you described - no introduction, no foreplay, and I presume you didn't see his face or exchange words - must have taken a lot of courage on your part. I guess this is how he wanted it: anonymous dick, walk in, fuck and leave. Maybe he's a famous senator or something and couldn't show his face. Who knows? The only thing we know, from what you've described, is that he used you for sex and he got what he wanted.

No wonder you felt awkward and shaken afterward. You just had sex for the first time, with an ass up in the air.

I think it's important for you to understand that it doesn't need to be like that. Sure, many of us enjoy hookup sex. Whether guys are finding their way, discovering their sexuality and not sure about being open about it, or just enjoy the thrill of the random encounter - there's a lot to be enjoyed when two guys get together for physical sex. You both want something and you can satisfy each other's wants. If everything's consensual and nobody gets hurt, that's great. Hookups can involve greeting each other, foreplay, enjoying bodies. The sex can be more personal, more relaxed and fun. Hookups can even progress to regular fuck buddies / friends with benefits, where you know each other, you know what makes each other tick, and you care about giving each other enjoyment.

I think if you want it again, you should work towards getting it. I know you haven't asked a specific question, but I'll answer a question you might be asking yourself: How can you work up the nerve again? My suggestion, if I may be so bold, is to forget the idea that sex should be what you described. Sure, you can hook up, but in a more friendly and interpersonal way. Grindr is very much about random sex, as are some of the other apps/websites: I've had mixed success with Squirt, where I've found guys who developed into good fuck-buddies. Chat with them, get to know them a little bit. If you're unsure, ask to meet them in public, say for a coffee. You might consider trying to meet guys in real life through bars or clubs if that's your thing. I understand you're young, finding our about yourself, and might not want to risk being outed; that's understandable. Try to figure out a way to have a better experience than what you described.

Let me say again - what you described was not what many or most people would consider to be good sex, and was not a great experience for you for your first time. Don't use that as a benchmark for what to expect.

If I may give you a couple of bits of advice. One is that if you want a particular thing, say you want to bottom, don't settle on topping just to get an encounter. It's not what you want, so why let yourself be used for your dick.

Another is that bottoming for the first time is a major thing to do. You should be prepared for it, physically and mentally. I suggest not doing it like that guy did, facing an unlocked door with your ass up. If safe sex is your thing (and I suggest it should be) stick to your game plan. Over on the forum "Health and Well-being" is a pinned page "All About Ass". It's worth reading and taking the time to learn about your body.

Another (and I did say a couple of bits of advice, lol, but here's more) - hookup manners. Bring condoms and lube, and a travel-pack of tissues, and a small bag for rubbish which you should clean up afterward. A guy may feel awkward after sex, like you did. Smile and thank him. You both got what you wanted. Always remember that if you're in his home, you're his guest, and behave as such. I'm not suggesting that, when you described removing the condom then leaving, that you left the used condom on his floor. But if someone did that at your place, you might think that was pretty poor form.

Man-sex done right is fun, mutually enjoyable, and need not leave us feeling awkward, shocked, ashamed or confused. Good luck and happy fucking!
Thanks for the tips. I admit I had let my nervousness get the better of me, and could have went about that a better way. I feel like my next time should be more personal. At the time I was very unsure of myself, and exploring. I understand that bottoming for the first time is a major step too. Mostly why I was okay with topping. I have read a bit about preparing for bottoming, and such, and have done so when I have used toys on myself. But I know a toy and an actual person is two different things. I guess I am still mostly afraid of "coming out" or being "outed" that are catching a STD. I did ask what to do with the used condom, and he told me to leave it there. I did get my first taste of what its like, but yes it could have been better.
 
I lost my virginity to a friend of mine that I never suspected was gay! After some pretty heaving drinking one .night, he asked me to drive him home from the bar. We had to pass my house before we would have gotten to his. I was kind of tired by then so I suggested we stop and rest and that I would take him home in the morning. As I only had one king-size bed he would have to sleep with me! We striped down to our tidy-whites and slipped into bed. I lay on my side facing away from him and was just about going to sleep, when he rolled over and spooned up behind me. He reached over and began to lightly feel my cock. I thought to myself, what the fuck is this? Has he forgot where he is? Well my dick betrayed me and started to get hard! Then I felt him slip down the back of my shorts and rub his hard cock on my ass. Still a bit loaded from the bar and being the passive guy that I was, I didn’t move. He must have spit on his cock and gently stuck it in my ass and began to slowly fuck me! I pretend I was asleep and never said a word. That was all the encouragement he needed! He rolled me over on my stomach and began to really fuck me hard. He soon cums in my ass, rolls over and goes to sleep!

The next morning we get up, get dressed and I drove him home. HE NEVER says a word about what happened! Maybe he was hoping that I thought it was a dream or he was too drunk to remember… we never did say a word to each other about it!…
 
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