A good day, dear reader! I’ve decided to seek for advise regarding the current state of my sexual life. With this I want to share a pretty long story. Of course, feel free to not read it entirely and perhaps only give me the advise I seek for, as it is not necessary to be familiar with the entire story, to give advise.

Over 2 years ago I (now 18 y.o. M) met a girl through a game (now also 18 y.o., half a year younger then me). After we’ve bin talking daily for about half a month we found out how much we liked eachother and decided to get into a so called long distance relationship, or at least you could say we started dating. We both had never bin in a relationship before. We got really close and comfortable with eachother rather quickly and we can talk about basically anything. We live far apart from eachother and only 4 weeks ago I finally had the opportunity to meet her in person. During our 2 years of this online relationship we also started talking about sex at some point a few months in. We where both completely unexperienced. As someone who had watched a lot of porn during my teenage years, I felt ready from the beginning and even quite excited to finally do it myself with her. Since she never watched porn (tho having mastrubated) it took a bit longer for her until she got at a point where she also felt ready for it. Some more months later we even started having conversations driven by our sexual imagination and desires while turning eachother on and mastrubating together. As time passed, the messaging became calling more and more often, as we felt more and more comfortable in this.

Now I am with her for 2 months straight this summer. During these 2 years we both became more and more sure that we’d end up having sex during my long awaited visit. I took condoms with me here, and read a few tips online here and there. The first night together the following things happened: I kissed, sucked and gently bit her neck and tits, which she really enjoyed, and I ate her out until I made her cum. i apparently did a very good job. She also gave me a hand job and tried to blow me. I didn’t end up coming this night and nothing felt that great either. I’m sure this is because she’s just unexperienced, nor has she ever seen anyone else do such things to a guy. She did enjoy giving me a hand job, but sucking it felt rather uncomfortable for her and she didn’t really enjoy doing it. She mentioned that she didn’t wanna take it any further for now, which I agreed on.

After about 2 weeks (she was also on her period during this time) we had a similar night. The difference is that she didn’t blow me this night and I attempted to finger her. She had never fingered before and I was being extremely careful and gentle. But as soon as I even found the entrance and even began my attempt to enter, she immediately reported that it hurt a lot. As she said this I also took my finger back right away, and this happend like this each of the few attempts I did, while also changing positions to find the optimal way. After that, and her not being able to get me to cum once again, we felt quite bad for some time. It’s not that she didn’t want to have sex, we where just both scared if the pain it was causing her if I’d even try to enter her wtih a single finger. But I assured her as much as possible that I don’t need sex in ny life, and that I’d rather stay with her and never have sex.

Until now, 2 more nights like these occurred quite close to one another: I finally came during night 3, mostly because she got a lot better at giving me a hand job and I imagined fucking her as good as I could. It also felt incredibly good at this point. The 4th night was the first time she didn’t end up coming. This is because I asked her for a final time if she felt like trying it again, and because her thoughts about me wanting it but she being scared of the pain made her feel quite bad again. It was dumb of me to bring this up at this time, I really regret this. We talked again and I gave her mire reassurance

Now I decided to make it clear that I’d NEVER ask her again or try things myself again. So it’s clear that she shouldn’t expect me to make any moves anymore, nor will we end up feeling bad like night 2 and 4. Only she would bring up trying it again if she’d ultimately feel like it, regardless of he fact that the pain will still be there. And if she would never end up doing this, then we’d simply never end up having sex.

FROM HERE ON I’L MORE CLEARLY DESCRIBE THE ADVUSE I SEEK FOR

I just don’t understand how you start sex if it hurts so much… Even tho we both read and heard about how amazing sex can be and feel, she just doesn’t want to experience the pain she felt until now and is even quite scared, and I don’t want to cause her such pain, not pressure her to just deal with the pain for now and accept it. I don’t think any advice could help me at this point to be honest… But perhaps someone could share their experiences and maybe tell me something I could do or maybe even address something that I might be doing wrong.

Btw, I’m sorry if my English is not the best.

4 comments
  1. I skimmed through

    Well until she doesn’t get any curiousity about sex, you shouldn’t do anything anymore.

    That said, a good path to take would be to start doing things with parts of your bodies that you are both comfortable with. Like kissing her neck, massaging. And maybe you can also try to see if she likes your leg between hers.

    Step by step you might be able to go on and maybe start playing with some more erogenous zones, like her nipples, or even your penis, but clearly not her vulva since she doesn’t like it.

    In any case, if she never gets any curiousity about it, it might also be that she’s asexual, and in that case sex might never happen at all with her. Or at some point she’ll be willing to do some stuff to explore or even just to please you, some asexuals do that. Some others will never agree on anything sexual.

  2. I remember sex being rather painful for a long while after losing my virginity (which, in and of itself, hurt). I also used tampons before then, which some people claim helps, but certainly did not help. One thing I might suggest is introducing toy-play, like dildos. Perhaps you could find something smaller to try and then work your way up from there. They have ones with all sorts of fun features too. If you want something smoother, try glass or metal. Silicone can feel a little rougher, so make sure you use a proper lubricant. And for that I recommend The Good Stuff; it’s a great natural lubricant available in all major grocery stores that causes me no issues and smells/tastes fabulous.

    When my current bf and I first met, he was a virgin and I was the experienced one. However, what I had experienced prior to this relationship was certainly sub-par, as I did not even think it was possible for sex to be satisfying or even feel good. Communication really is key to having good sex. Anytime something hurts I’m sure to let my bf know and we adjust accordingly.

    So, don’t give up. Prioritize making her feel good. Make sure she’s really ready (proper lubricated) before you insert anything into her. Go slowly. Work your way up in size. Eventually, you’ll get there. That’s my best advice.

  3. Just be enthusiastic about sex. You’re not going to be good at it the first time you do it. To make it more enjoyable try to keep the excitement and great it as a stepping stone and practice to get better!

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