How I Learned to Stop Worrying and Love the Cock

Note: This got really long, apologies. I guess I just needed to vent as this is all true and I have nobody to tell it to. This deals with my many years of fantasies and how I finally made the leap and met another guy, hopefully it will be helpful to anyone in the same boat.

I am your ‘typical’ 20-something ‘straight’ guy, date girls, enjoy sports etc, all the cliché stuff. For years however, I’ve always secretly fantasised about sex with other guys. These have taken various forms over the years, but have primarily focussed on me being a sub(ish) bottom for older men. I enjoy looking at pictures/videos of twinks and transwoman, however the vast majority of my gay fantasies have concerned me bottoming for daddies, often in semi-anonymous settings with cross-dressing elements.

Naturally, I have always watched a lot of gay porn, and my tastes definitely reflect my fantasy life. I’m also fairly active on various hookup sites and apps like Grindr. I’ve had lengthy and often quite personal chats with countless guys over the years, have traded pics and cammed with many of them. However, despite my strong desire to actually have sex with a man, I have never managed to take that final step and actually go through with it. I’ve made lots of half baked plans with guys, stuff like ‘I’ll be free next week’ and ‘I might be free on Thursday’ etc., empty promises that I already know will amount to nothing. I would get that sick nervous feeling in my stomach even at the thought of it, and had essentially resigned myself to the fact that I would be too cowardly to ever do it. At points I wondered if I was even bi-curious or bisexual at all, or if my desires were simply fuelled by horniness and too much porn. I think I used this doubt to justify my nerves about meeting.

My normal routine is to filter out everyone below the age of 40, so I have my pick of mature men to chat with. This changed over the past month or so, for whatever reason, and I found myself chatting to more guys my own age, give or take a few years. To my surprise, I discovered that I really enjoyed talking to younger guys, perhaps even more so than the mature guys I had spent so much time on. Sure, many of them were creeps or pushy etc, but a lot of them seemed really cool, and I felt our conversations flowed better and felt more natural.

Sometimes conversations would barely involve sexual chat, if at all. This didn’t happen often, but I actually found it refreshing when it did. It was interesting to get a glimpse of the actual personalities ‘behind the dick pics’, if you will. This was never something I would have imagined myself ever caring about, as I always felt attracted to cocks and mens bodies and never particularly cared for the rest of the person.

Two weeks ago I started speaking to a guy a couple of years younger than myself. He was a slim twink, slightly femme in appearance but not ‘trap’ like or androgynous. We had a great conversation over a couple of days, touching briefly on sex, but mostly about hobbies and interests, of which we shared several. Eventually, he asked if I would be interested in going over to his place. This immediately gave me the familiar nervous sickness, and I closed Grindr with my heart pounding in my chest. I didn’t reply to him for a couple of hours, and sat for a long time thinking about what to do.

I almost never tell guys online that I am a virgin with men, opting instead to portray myself as an experienced bottom who loves getting pounded. I find this works to get the kind of chat I’m looking for started, plus I don’t particularly like being seen as a virgin who needs to be broken in, which a lot of guys seem to be into. With this new guy, the topic of sexual history hadn’t come up, and so I thought to myself that if I wanted to actually meet him, my best option would be to be totally transparent and honest about my experience and what I was looking for.

I messaged him back and pretty much told him I was totally inexperienced and was scared shitless of actually meeting up with someone. He was great, so understanding and told me I could just come over to hang out and there was no pressure to do anything. He sent me his address, it was an area not far from my house and a neighbourhood I knew well. I told him I would be free the day after next, a promise I’d made to countless guys before him, but something definitely felt different this time.

My mind was absolutely racing the following day, I was a mess with anxiety and nerves. One primary fear that stopped me from meeting in the past was the idea of getting murdered by some sketchy older dude. This guy was younger and smaller than me, so (hopefully) wouldn’t be much of a physical threat, and he stayed in a nice part of town that I was familiar with which helped to further allay those fears. I had a new fear now, however, the thought of me getting there and realising I wasn’t attracted to men at all. I had a horrible vision of me realising I’d made a terrible mistake, and that my mind had been warped by excessive porn and fap sessions, and that it would be terribly awkward and embarrassing. To get past this, I thought to myself, ‘it might be awkward, so what? If I get there and I’m not into it I can just makes my apologies and leave and never have to think about it again’. This really helped settle my nerves, and I felt a lot more comfortable about the whole situation.

The day came, and again I was a nervous wreck. I did my best to push my fears to the back of my mind and started getting myself ready. I had agreed to go up early afternoon, so I wouldn’t have the chance to wait around all day, overthink it and chicken out. I did some man-scaping, douched my ass just in case, and made sure I was dressed and smelling nice, then it was time to go. The hardest part was stepping out my front door, I had to will myself to do it. Once I was out of the house though, it was surprisingly easy, and I felt (almost) fine on the drive over. It took me about 25 minutes to get to his place, and once there I parked outside, walked up and rang the bell.

As soon as he opened the door I knew I had made the right decision. He actually looked better than his pics, he was extremely cute and I was immediately attracted to him. We made some small talk, and he offered me a glass of water. Our chat was slighty awkward, but no more so than you would expect from 2 people who had literally just met. We ended up sitting next to each other on the bed and, during a brief lull in conversation, I thought ‘Fuck it’, and kissed him. Now, kissing has never played much of a part in my previous fantasies, but as soon as I saw this guy I wanted to kiss him, and we kissed A LOT. It got heated pretty quickly, and we were soon totally naked and all over each other. My fears about not being into it had disappeared as quickly as our clothes, I was rock hard and horny as hell. Once we managed to stop making out, he got his mouth around my cock. He sucked me like an absolute pro, and I had to push him off before he made me cum already. I took his cock in my hand and shuffled down the bed. It was slightly smaller than mine, but still really nice. Holding another guys dick in my hand was surreal. I took it in my mouth, and gave him the best head I could, which admittedly must have been pretty awful. It was a strange sensation, the skin felt a lot looser than I had imagined, and the taste was weird, I didn’t dislike it but I didn’t love it either. I did really enjoy the act of sucking cock though. Eventually we were making out again, lying side by side with our bodies pressed together. I loved kissing him, his face and lips were a lot softer than I expected, and it wasn’t totally different to kissing a girl, but it definitely felt a whole lot steamier and passionate. We lay like this for a while, making out non-stop and jerking each other until we both blew massive loads over ourselves. It was amazing.

In the lead up to meeting him, I had no idea what I would feel like once the deed was done. I was half expecting to feel disgusted in myself, ashamed, and to make my excuses and escape quickly, blocking the guy on Grindr before I even made it to the car. It was totally the opposite however, we lay there intertwined for ages, chatting shit, still kissing now and then and gently touching each other. I loved this part, and it was something I hadn’t even considered possible or even thought of at all. After a while, I had to go, but I really wished I didn’t. After getting dressed we stood and made out some more, before I had to really get going. The drive home felt like a dream, and I was on auto-pilot the whole way home. That night I messaged him and thanked him, and he said he really enjoyed himself, which pleased me, and said I’m welcome back anytime. We’ve made plans to meet again.

All in all, it was a great experience, and I’m relieved to have done something I’ve thought about for so long. What really helped me take the final step, and this might be of some help to anyone in a similar situation, was to make an actual connection with someone beforehand, as cheesy as it sounds. I’m quite a cautious person by nature, and the idea of a hookup after 2 messages with someone I don’t know at all makes me weak at the knees (not in a good way). It also helped to be honest about what I was looking for, and my lack of experience. This really took the pressure off and I felt I could be a lot more like myself.

The final point I’d like to make, is that I’ve always considered myself to be ‘bisexual heteromantic’ or whatever it is, basically attracted to men only sexually, but woman both sexually and romantically. However, what happened after I shot my load with this guy has made me seriously reconsider this, and I think its worth noting that labels I had affixed to myself prior to a sexual experience seemed wide of the mark after the fact. Maybe this won’t apply to others, but maybe it will.

If you got to end of this, thanks. I probably rambled too much, but definitely wanted to get it all off my chest.

7 COMMENTS

  1. Not at all. This was a great read. And btw you should write a book or something your choices of words and sentences are a pleasure to read.
    I have the same sort of thing.
    Ill explain. I luv anal sex and using big toys and i even huff poppers gets me very horny.
    And at the same time im hetero AF. I really luv Girls and women.
    But at the same time i really would love to experience a guy a bigger muscular not even neccesaraly could be a well Hung twink type of guy as well Just absolutely plow me. Sorry for my rather rude choice of words.
    In regards to the kissing i dont know never thought about it had one experience with it eons ago and didnt like it. Could i Kiss a guy? I guess i could.
    Anyway nice read and hope you have some more nice meetings with your New friend.

    👌💕💪

  2. Nice! Thanks for sharing.

    >It was a strange sensation, the skin felt a lot looser than I had imagined, and the taste was weird, I didn’t dislike it but I didn’t love it either. I did really enjoy the act of sucking cock though.

    LOL that was my first time to the T (just with 15)… And if my subsequent experience is anything to go by – you may well become a very passionate sucker 😀

  3. Mate, I feel so seen. I felt like I was reading about myself.

    * Romantically attracted to women but fantastise about sex with guys
    * Have been on Grindr/Scruff for years and been through endless chats and empty promises to meet
    * Almost gone through with it multiple times but been scared to death

    but then add to it the complication that I’ve been with my now wife since I was in high school (I’m 30 now) and I hid these feelings from her for so long. I never cheated on her but I was so close so many times.

    I should probably do a more in depth post about this but I did end up telling me wife my fantasies and she agreed to allow me to explore with men. I’ve yet to make the plunge but your post has given me more courage to do so.

    I agree with your point about making a genuine connection first. I’ve met a couple of people in person where I had a decent connection but the feeling wasn’t there physically. It takes so much of the pressure off to “perform” when the expectation is just to have a chat and see where things lead.

    Thank you so much for posting!

  4. Great read!! Some points and feelings really hit close to home with me. And I’ve learned a new label to use… “bisexual heteroromantic”. Sums me right up 😁

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