M27. Still a virgin, lonely and depressed. Though I’m working through my trauma with a therapist.

I’m wondering if any, preferably guys, could chime in on my situation.

I missed the sexual train throughout high school and university, primarily by being socially awkward and introverted – you know the kind.

With this in mind, I’m feeling ready to date, quite possibly in a year or two. Lost weight, built a quality physique, finished my degree with a good job at the end of it, and in general much healthier compared to my early 20s. I’ve allocated the next 1-2 years with the intent to work on platonic relationships/social skills.

I’m feeling kind of envious of all the missed years and sexual opportunities gone by. I want to catch up through casual dating. I also want to enter a more serious relationship at some point but worry that no experience will hinder me if I don’t start now.

A period of experimentation so to say – I frankly don’t know what I like, sexually.

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Is this a feasible plan and can it be approached in a sex-positive way that won’t come to bite me later?

Personal experiences and anecdotes are appreciated.

13 comments
  1. I mostly hooked up with people through serious relationships then did something similar to what you’re saying now. Basically worked on my self, dated and hooked up like crazy, tried experimenting, etc.

    It made me more confident and when my ideal partner fell in my lap I didn’t have any lingering thoughts about other people or desires or anything in the back of my mind. I had proven to myself I could do it, and frankly finding someone to hook up with can be a lot of work, so I was extremely happy to stop dating and end up with my ideal partner

    It’s important to be safe, if you experiment with bottoming to other men be very careful and make sure that they know and agree to use condoms. Lots of guys out there will either say “well I can’t come without a condom so if we’re going to hook up I don’t want to use one”, and a small number may try to stealth you (that’s happened to me), so keep an eye open for that

    As long as you use protection and get tested regularly I can’t see a real issue with this. Keep working on yourself and have fun and be open to having “the one” fall in your lap

  2. Im not a guy and also not the age youre asking about, but bear with me.

    Having multiple casual partners doesnt (in my opinion) mean that you dont care about them at all. I would recommend you to not have too many ONS, but thats simply because sex tends to become better the better you know your partner. First time sex is basic. You dont understand yourself, nor your partner, plus you only do the most pressing/basic stuff since you dont really know when the next time youre gonna be able to score a partner would be. I guarantee you, having a reoccurring partner and slowing down to enjoy various scenarios and fantasies makes it much better.

    Id recommend you as well to actually date a bit, in order to gain some relationship experience. Teenage love is so increadibly short lived and messy not just bc of hormones but also bc they are wholly unexperienced. Without practice you dont know where your boundries are, how you prefer your partner to treat you, where your own weaknesses may lie. Theres a whole other persons life that you gotta intergrate into after all.

    Anyway, what i wanna say: date, fuck, do whatever with an open mind. Dont rush, dont have some mental checklist to fulfill and quickly rushing to the next point. Stir the boat as you want, when you get to the wave, dont obsess over a previously mapped out route.

    Oh and more about your question: Personally i dont think that hoeaing around is an endless endeavour. Personally I dont think about “whats out there” nor am i noatalgic about past conquests. Though that may be a consequence of finding out that not all rare fish are tasty, hah. Once you got them on the plate you may be very disappointed. Really gotta judge with your stomach, not with our head.
    However there ARE people out there that just cant stop. Usually they notice that theyre the happiest having casual partners, that they dont want being monogamous. I cant tell you if youre one of these people, so im afraid you gotta ask yourself that question

  3. You missed the first car; the train’s still running. Hop on.

    Yes, you can have fun and gain experience in a sex positive way. I did this with the apps. Approached it like I was looking for “something casual” or “fwb.” I would flirt a little dirtier (but really, nothing serious lol no pics or anything directly explicit, just not your Sunday church coy flirting).

    After meeting in person, if the vibe was still there, I’d bring it up over text. I never found the courage to do it irl. But I would just be super clear and positive about it. “So I’m really on the apps looking to explore myself sexually. I haven’t had much experience, but I have a healthy curiosity and would love to explore with someone sex positive and up for it!” The convo would go from there lol. How they responded was a “weed-out” gate for me.

    Some were weirded out, some said some red flag things, almost all asked questions about lack of experience. As a woman, I was fetishized often and had my safety radar on high alert. I really wanted to make sure I wasn’t meeting up with anyone who’d take advantage.

    I’d be prepared with how you’d answer the “how’d you get here” in a not-depressing tone. Something like “I was really quiet and introverted throughout high school and college, and didn’t have confidence to break out of my shell. Once I was out of school, it was harder to meet people in general and the pandemic certainly didn’t help! I’m making a genuine effort now to get out of my comfort zone and have some fun.” I’d talk ahead of time about what I was comfortable with, what I was interested in, etc to establish if we were generally in the same ballpark in our sexual interests.

    I hope you can get out there and have fun. I hooked up with some really kind, attractive, thoughtful, and fun people!

  4. Late virgin here, had sex first at 29.

    One thing I didn’t really knew about (or I knew, but didn’t *really* know) is that sex is a skill. Not just in making it enjoyable to others, but enjoyable to yourself. There’s a non-insignificant chance you may have premature or delayed ejaculation your first time, even if you are fine when masturbating.

    And if that happens, you really want a caring person who sees some value in you besides the sex if you don’t want to add to your traumas. If your whole value to them relies on how good at sex you are, you might inadvertently create a lot of pressure for yourself.

    That doesn’t mean you shouldn’t go with your plan. But I would at least advice you don’t have your first time with any random you met that day. Not because of any “Your virginity is precious” crap, but to avoid getting started on a rocky start.

  5. It’s alright to be late. If you are worried about being a virgin, you can get an escort/prostitute to get over that first time and gain some confidence.

    I’m a guy like you and started out late, around 32-33. Had my first time with an escort. Wasn’t planned, I just happened to be there, in the mood. Subsequently, I decided to use apps. Paid subscription for those apps, got more hits. Was very open about wanting just casual relationship and I actually manage to hit it off with 2 girls around the same time. Had some fun times with them but soon there was some emotions involved and I called it off.

    So, you have nothing to worry about.

  6. I wasnt a virgin but I got married pretty young and got divorced at 32. I had a fucking blast. It was an eleven year marriage and my god things changed. You’ll be fine. Just make sure you actually get out there and do things in the real world and make yourself at least somewhat interesting. Do things you love. People dig that.

  7. I’m M27, didn’t lose it until 23, never been particularly sexually active, the most so was probably in my one real relationship, I can count on one hand the partners I’ve had, so I never got to have a “hoe phase” I wish I could, because I am an incredibly horny bastard, but I unfortunately work constantly and live with my parents and am incredibly socially awkward. Cards just seem stacked against me. Idk.

  8. I went through my hoe phase in my early 40s. I lost my virginity at 16 and only had sex with 3 people until I was 41.

    I missed a ton being married to an asexual woman for 14 years.

  9. I’m 36 going on 37, I’ve yet to start my hoe phase because I’ve been shy and awkward most of my life. I’ve been reading books like Models by Mark Manson to become more skilled at the dating game.

  10. I lost my virginity at 16 but for reasons kinda like yours haven’t had a ton of sex between now and then. Or rather, there have ended up being loooong dry spells. I’m 29 now, feeling better about myself than I have in years and am similarly looking to fill in some gaps in my experience. So you’re not alone.

    Going straight into one night stands with people who have more experience might be daunting though, so I’d go looking primarily for fwb’s who get your situation and are willing to work with that though. Chances are that’s going to be a better introduction, one that’ll teach you more and have you feeling confident and comfortable sooner.

    For me anyways, the best sex I *have* had was when I’d been with the same girl a few times, enough to not feel anxious anymore, get over the cumming too fast/not getting hard-fears and to know my way around enough to know she was having a good time too.

  11. It is very common to not discover your sexual self until your late 20s or 30s.

    Lots of people for lots of reasons end up in that situation. Sometimes sexual trauma, health issues, or body image issues keep people from really exploring sex until relatively late. Sometimes people have busy or stressful lives like going to Med School or having a child as a teenager.

    Some people end up getting married young to someone they don’t have good sex with, and they don’t get divorced or open up the relationship until 10 years have gone by.

    And, because of surveys of sexual satisfaction done by groups like the Kinsey Institute, we can actually say that *for most sexually active people* the sex they have in their 30s is much better than the sex they had in their 20s.

    It might be several more years before you start having sex or having the sex you want— but then you’ll still have literally decades left to enjoy it and you won’t be alone in that journey.

  12. Absolutely possible. Something like that happened to me. I got my first date at 27. My dating skills snowballed after the first few dates. My first date just wanted something casual and she didn’t really believe I couldn’t date so she generously put a lot of time and effort coaching my conversation skills to be less awkward and weird and making my dating profiles better. That gave me the skills and confidence to go from never having dates despite putting many hours a week into dating attempts to being overwhelmed, going on 3 dates with 3 different girls a week and having to stop seeing some girls as I didn’t have the time. I had dates with a dozen girls and had sex with 7 of them before finding my current partner and stopping that within 3 months. I preferred the relationship but I could absolutely could have continued the hoe phase if I wanted to. Hoe phase still feels lonely but relationship does not imo.

    I did get very lucky to have such a kind and helpful first date. She helped me so much. I am also in good shape, have a good job, am tall and probably have it easier than a lot of other people. So this might not work for everyone.

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