Nervous

[Indestructible]

So, I (a 24 year old guy) have never had sex, never even kissed a girl or done anything the least bit sexual, never been on a date or in a relationship, etc., and I find myself in a position where I can actually change that.

I was always much more interested in finding a "proper" relationship, someone I really liked and cared about, rather than chasing after sex. But I'm in the process of giving up on that mindset, and decided to maybe just focus on finding a casual sex partner (preferably, a FWB). With my poor real world people skills, I spent months slumming Craigslist and Adult Friend Finder, but ultimately had no success.

Then, a few weeks ago, I finally met an older woman on AFF that I got something going with. We chatted a little, then exchanged phone numbers. We spent the next day texting back and forth, getting to know a bit about the other, swapping pictures, and later, started really talking sex. We've kept in touch via texting since.

Everything about her checks out, and overall, her situation is extremely ideal for me. We sort of scheduled September 4th as the day we're going to get together and have sex, although we're meeting next week first for lunch.

On one hand, I'm excited and I can't wait to have some fun and really learn about sex. But on the other hand, the more "real" this becomes, the more nervous I get, and the more nervous I get, the more I almost don't want to go through with it. This is probably the best opportunity I'll have to be with someone/ have sex in the near future (maybe ever...), so I really feel like I should pursue this. But the nerves really get to me... I know it's "normal" to feel nervous about first time stuff like this, but I guess what I'm wondering is, how do I get myself to relax, stop stressing out, and just enjoy my time with this woman?

[Ginger2013]

Focus on the lunch first, you have to get to know her in person a bit for those nerves to settle a little. You'll still be nervous, it's normal, maybe just do something to relax yourself before the big day. Before I lost my virginity I had a few drinks, it helped a little, though I'm not advocating it for everyone.

[Indestructible]

One thing that makes me a bit... uneasy, actually has nothing to do with her. It's about my own intentions. See, there's a girl I've been hung up on for a very long time that I have/ had real feelings for, but she's more interested in dating/ sleeping with idiots. Part of the reason I've been attempting this is to sort of even things out, so to speak, and possibly help me get over her. But whether or not having casual sex with this other woman will do that for me, I don't know. In a weird sort of way, that's making me nervous and uncomfortable, too.

[Ginger2013]

This older woman has been clear it's just casual? She doesn't want more right? You have the jitters because you've never done it before, don't think too much about it. But sleeping with someone to get over someone else...I don't know if that actually works emotion-wise.

[Indestructible]

Oh yeah, she knows, she actually mentioned it before I did, heh.

[Ginger2013]

Then just enjoy it. Go to lunch, let her spoil you a little. Then have some fun! I'm an older woman with a younger man and he's mentioned many times it's the most uninhibited sex he's ever enjoyed, I've heard that a lot with older women and sex. You'll have fun and learn a lot in the process!

[michelle23]

I think you could v easily end up getting attached to this woman. Im not sure its a good idea. Maybe have sex with her once if you really wana lose your V but i wouldnt make it a regular thing. Maybe losing your V and just doing it once will help you get out there and find what you really want (love). I think you just need an initial confidence boost to help you come out of your shell

as for the girl your trying to get over. Have you cut all contact with her and accepted you can never be friends?

[Indestructible]

I think you could v easily end up getting attached to this woman. Im not sure its a good idea.

I'm not particularly worried about that. She doesn't seem like a bad person, or anything like that, but there are several factors that I think would definitely stop me from wanting to really "date" her (for instance, I don't want to actually "date" someone that's that much older than me, nor do I want to "date" someone that has kids, let alone kids that aren't THAT much younger than I am).

Maybe losing your V and just doing it once will help you get out there and find what you really want (love).

I don't believe I'll ever find what I "really" want. Over the last year or so, I've been finding that harder and harder to believe in, and I've hit the point where I just can't do it anymore. "Mutual attraction" (not physical, I mean) just isn't in the cards for me. If I hold out long enough, yeah, I *might* find a really cool girl that I want to date, but chances are, there's going to be some other guy (or guys) that are "hotter" or "cooler" or "more exciting", generally more attractive than I'll ever be. What I really want just isn't a possibility for me, plain and simple.

as for the girl your trying to get over. Have you cut all contact with her and accepted you can never be friends?

I can't, because she and I work together. She and I have started getting chummy again, which initially made me happy, because that went away for a very long time when she was dating some other guy that ended up cheating on her in the long run. But then it started coming back after they split, and I just enjoyed it at first, but now I'm starting to realize that she's reminding me again why I fell for her in the first place. I'm still indulging in it, because it's fun, and I don't have that kind of chemistry with another person, but deep down, I keep scolding myself for it, because I know it just makes me want her again.

I assume within the next few months, though, that she'll be finding a new, better job, and that will be the last I see of her. Which, is probably technically a good thing. But at the same time, I don't WANT to "never see her again". I've never met anyone like her before, and I really don't believe I ever will again, so it's hard to just let that go. I don't WANT her to go away, I don't want that to be the end. But what can I do?

I don't know WHY I think or hope that getting it on with some other, older chick will make it better, but there really doesn't seem to be anything else I can do to get rid of (or at least lessen) the feelings I have for this other girl. Maybe "having fun" with someone else will ease the pain, and weaken the feelings I have?

[michelle23]

Have you tried therapy OP? I think your biggest problem is you lack confidence and the women you want would rather a confident guy. Having no self-belief is unattractive. Im not talking about the cocky douchebags who treat women bad. They are losers. But being a confident nice guy really helps

[Indestructible]

Perhaps it doesn't come across through my posts here, but I question the whole confidence thing, because I try my best to come across as a confident nice guy out in the real world, and for the most part, I like to think it's a non-issue.

[FlaCooln]

Dude...you are overanalyzing and complicating this whole thing.

Keep it simple....You are a Virgin and inexperienced so use this opportunity with an older woman to learn and grow. Don't worry if you screw up and the sex is bad, as you’re not marrying the woman. Trust me, from experience older woman are awesome to learn from. I've dated a few in my time and never had a bad experience, as they can teach you a lot. Keep the communication lines open, ask her questions (find out what she wants/likes), and she will lead you the rest of the way. Use a rubber and have fun man.

I think having sex with her will do wonders for your confidence. Personally, I lost my virginity at 19 or 20 (sophomore in college) to a girl my age that I didn't really see as anything special. But, I figured better to get some practice in and learn when it doesn't matter then with a girl I actually cared about and saw a future with. Well, without me really thinking it would it totally changed me. I became a lot more confident and just way more comfortable with women and able to express my personality/be myself. For me it was like turning on a light switch.

IMHO I think waiting too long in life for sex for guys makes them socially awkward. Go for it and have fun!

[Indestructible]

Okay, so let me start getting to some more sex-specific questions. Er, well, I guess I only have one right now, because someone mentioned this to me elsewhere, and I found it a bit obtuse, so I'm wondering about it. I know oral sex is going to be a thing with this woman, and someone elsewhere said to think about using dental dams. I've heard of this usage before, a long time ago, but do people really do that? How dangerous is it really to give a woman oral sex without some kind of "protection"? Is this something people actually use, or is it a little too "out there"? Where does one even acquire these? Are they really worth going out of the way to find and use?

[Exeter19]

listen to music you like before you go to meet her, and like ginger said have a drink or some weed even to relax. don't put pressure on yourself or you won't be able to do it, or get hard. stop over thinking.

[VerticalMoon]

You're an adult, and this is entirely your decision. If you want opinions, though, I think you're better off not pursuing this. Sex shouldn't feel like something you have to do even though you're not really comfortable with it. Wait until you have somebody that you know well, and it will be much better for you.

I just think if you want is an actual relationship, this won't really help very much. You might feel really good for about two weeks knowing that you find an attractive lady to sleep with you, but that will wear off when you realize you're still single. If what you want is a relationship, then I wonder why you haven't put the same effort into getting a date that you've put into getting sex? I'm sure if you put months into legitimate dating sites, you would have gotten at least a date by now. Seeing as you haven't even done that, I think you're giving up too soon.

[FlaCooln]

You're an adult, and this is entirely your decision. If you want opinions, though, I think you're better off not pursuing this. Sex shouldn't feel like something you have to do even though you're not really comfortable with it. Wait until you have somebody that you know well, and it will be much better for you.

I just think if you want is an actual relationship, this won't really help very much. You might feel really good for about two weeks knowing that you find an attractive lady to sleep with you, but that will wear off when you realize you're still single. If what you want is a relationship, then I wonder why you haven't put the same effort into getting a date that you've put into getting sex? I'm sure if you put months into legitimate dating sites, you would have gotten at least a date by now. Seeing as you haven't even done that, I think you're giving up too soon.

I totally get where your comming from. But, the dude is 24 and there is a certain age that women just expect you to know what you are doing. A girl his age or around his age may or may not be as patient or willing to teach him. While I do agree that sex is way WAY better when it is meaningful. There comes a point when you have to explore sexually. IMHO if he knows what he is getting into and talks openly with the older woman it could be a very enjoyable experience for the both of them.

Sex does not always have to mean something. For the OP this time it can mean a sexual education.

Lasly, to the OP...if you are worried about oral/STDs and the like then both of you should go get a STD/HIV tests done. We know your clean, but its good form to get one yourself if she is.