Hey all, I guess I’m sort of looking for advice in multiple areas, thanks in advance for any and all help. So I came out about 5 years ago (I’m in my 30s now), but still haven’t done anything with a guy (not even kissing). I’m completely comfortable with my sexuality but it just hasn’t happened yet. I’ve been putting myself out there on the dating apps, but have only managed a few dates and no chemistry on any of them so nothing has happened. I go back and forth a lot, because ultimately I would like a relationship, so I feel like maybe I should wait for that, but I also know there’s nothing wrong with having some fun along the way in the process, and I do sort of feel like I’m missing out being in my 30s not having had any sort of sexual experience yet. I definitely find myself in general more attracted to older guys, and I usually am more drawn to them on the apps, not only because I just really find them attractive, but also because of the fact that I feel like I’d be a lot more comfortable for my first time with a guy who is more experienced and can really help guide me through the process to ensure we both have a good time. I really want to bottom, it’s what I’ve fantasized about and I really want to try it, and I really want an experienced top that can really help me enjoy it through my inexperience (I’ve never even fingered myself or anything like that so it would be all completely new for me). I guess my hang up is that every time I start chatting with a guy, I sort of just stop the conversation. I’m not sure how to bring up the topic of it being my first time and what I want, so I just sort of back down. I’m not necessarily looking to be in a long term relationship with an older guy, but I’m not necessarily looking for just random hookups either, I just like the fact of having an older more experienced top to guide me through my inexperience. I do really want to have the sexual experience, I feel like I pushed myself so hard to get over my fears and come out, and haven’t even gotten to enjoy the physical part of it I’d really like to. As I said before, being in my 30s now as well, I think I’ve just built up losing my virginity so much. I’ve done a lot of research on anal sex and bottoming but I still really feel like I don’t have any clue what to do, but I really do want to have that experience. Does anyone have any advice on how is the best way to sort of get over my own insecurities of being inexperienced and a virgin, and any tips for bottoming? I just sort of feel like I keep shutting every potential option down in an attempt to wait for Prince Charming to come along for my first time, even though I know there’s not really any reason to deny myself pleasure and fun in the meantime. I know this is a super broad question, thanks for any and all advice anyone has.
Hey First of all. I don't have a lot of experience. I've only been with a few guys for anal sex. In my experience, it is better to be intimate with someone you have a relationship of some sort with. My first time was with a guy a lot younger than me (I was almost 60) that I met on an app. We met, had dinner and only limited intimate contact the first time. Then we started seeing each other to do some rock climbing and hiking and little by little got to feel very comfortable with each other. One camping trip we decided, together, it was time for me to try bottoming. Because I trusted him, it was one of the best experiences of my life. And, he had very little experience. So, I don't know that it matters to find someone who has experience. I think it is more important to find someone you trust. We didn't have a romantic relationship. Just friends. But, I still chat with him often even though we have both moved on. I did have a one night stand once and I hated it. We all have to see what works for each of us. But, I highly encourage you to try the dating, then sex, approach. From my experience, any guy worth having will not have a problem with your situation and may find it appealing. The thing about sex is that it is the best when the goal is to please your partner. So, being with someone who you know well enough to want to pleasure is important. This doesn't have to be the love of your life. But, it sure helps if he is at least a friend. And, in my experience, sex gets better when you learn what your partner likes. So, a one time thing may not yield much of what you desire and you may find it disappointing. As far as preparing to bottom. It might be good to try some toys to allow you to learn how to relax and to learn what you enjoy. We are all a little different. Good luck.
