I (m24) recently started flirted with a woman (38f) i met from a common social circle, and we went on a date last weekend. I felt a lot of chemistry and the thought of hooking up with or dating an older woman was really hot. I guess i also craved the intimacy because i don’t have much dating experience.
We were touching/flirting throughout the date and building up tension. When we left the bar, she invited me back to her place and i happily obliged.
However, I’m sexually inexperienced and wasn’t sure if i was ready to lose my virginity to her. I came clean with her and told her that while i have fooled around with women in the past I haven’t gone all the way. I kept on mentally asking myself if I’m ready or not.
She was understanding and made sure i didn’t feel pressured. After getting naked and fooling around for a bit, i thought fuck it let’s just get it over with. She double checked with me and then we tried having sex.
I put on a condom but then couldn’t get it in. Even though i was hard it just felt like poking through a wall. We tried changing positions, got her on top so that she could guide it in. But after not getting in the first few times i started losing my erection in frustration. So we just gave up on intercourse for that night and just cuddled more.
I haven’t seen her since then as she was away for a few days but I’m supposed to see her again next week. But a part of me is just not interested anymore. I don’t feel the same spark of attraction. I don’t know if it’s because it was just supposed to be a one night stand for me or it’s because of the frustration of not being able to have sex. We both also went down on each other but i wasn’t able to properly relax/enjoy. I haven’t been able to cum from any of the 3 BJs I’ve had in my life.
I know there’s a lot to unpack here but I’m kinda looking for the following answers, is it more likely that I’m just not that attracted to her, or is it because of the frustration of not being able to have sex? I’m kinda reluctant to go all the way because I’ve put my virginity on a pedestal due to cultural reasons. Even though I’m not saving myself or marriage or someone i love, I thought it would have happen with someone I have passionate lust for.
Also I’m slightly worried i may have a death grip problem because blowjobs feel just mildly pleasurable and I’m not even close to cumming from them. How do i sort these issues out?
5 comments
First thing is I’d suggest really trying to relax around all this. It sounds like you have several forces all pulling on you (you want to stay a virgin and you want to have sex and you want to find an amazing parter and you’re concerned about porn and masturbation etc) and those are all pulling you around. So yeah take a breath and slow down.
Secondly I think it’s wise to trust your feelings. If you don’t feel this is the right time or this is the right person then trust that and wait.
Thirdly I think a really helpful thing with sex is to focus less on penetration and much more on eroticism and everything around it. Like you can go to her house and giver her a long sensual massage, for instance, and that can be super erotic and tingly and fun and sexually satisfying, without your dick being involved.
So many people get trapped on the rails of “foreplay” -> “penetration” being sex and honestly it’s like the only meal they can cook is steak. And sure steak is amazing. But that’s like 0.1% of what food can be.
So yeah just relax, go slow, breathe. This are very usual problems a lot of people have. Give your body a chance to work the emotions through. Communicate and just see what happens.
Definitely because of the frustration you couldn’t have sex properly.
If you liked her, and still do, and she seemed supportive and comfortable to be with through a clumsy first go, I’d imagine frustration and maybe a little embarrassment are hanging over your current perception of her. Maybe enough to make you want to pull away from this.
Of course it’s your life and your choice, but the only way you’re going to know what it is and if it can be overcome is if you see her again and sort your feelings out, which sounds like something you already gleaned from another comment so I’ll just add this: the nice thing about older women is there’s very little they’ve not seen and handled. They’re patient and understanding and pretty hard to shock. She’s probably been hoping you’re not worried about anything that happened and she’d probably be happy to explore some more stuff again if you’re up for it.
It’s frustrating when you want to have sex but things don’t work out. Since you already have some experience with her, go out again and see what happens. If it doesn’t work out again, move on. Maybe your dick isn’t attracted to her!💋
You have to push forward despite all your worries. Feel the fear and do it anyway!