Well, it finally might happen.

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As some of you know, while I'm looking for a cute/cool girlfriend around my age (I'm 26), I like older attractive women (30s, 40s) and would love to have sex with one especially my first time, that way there's no "what are we" pressure after. I'd break my no sex without serious dating rule for sex with a milf. And now I have my chance. The past year or so, I've been on plentyoffish looking for either a girlfriend (bad idea I know, the site sucks) or a worthwhile older woman to have sex with. Most women on there say "I'm not a cougar." or "You're cute. I wish you were 10 years older." Well finally, an attractive 48 year old woman is interested in meeting for sex without expectations other than that I try to keep in contact with her and stay friends with her after.

I don't know why, but suddenly last night, despite this being the scenario I've been looking for (she's my type physically, it wouldn't be settling), I started getting massive headaches and couldn't fall to sleep.

I don't know what I'm afraid of. I can think of few things, but none of these are satisfactory answers:

1.)The past few months, I've been so caught up in the idea of meeting the right one and falling in love that just about any woman I meet off the internet or in real life won't match up because I've been thinking in terms of "ideal."

2.)I'm afraid sex will change me and I'll become a typical guy just after the next hit and lose my desire to meet a good girlfriend.

Those are the only things I can think of. I'm physically ready to have sex. I would have had sex with the last girl I dated if our personalities hadn't have clashed before it got to that point. So I don't know why I was unable to sleep and with a migrane?

I only hope you don't contract a Sexual Transmitted Disease...there are alot of those things going around these days.

Well now it looks like it has a 99% chance of happening, and I'm excited. She empathizes with the situation (26 year old guy that was depressed for years, wants an attractive older woman to teach him)...and she wants to make a night of it. Not sure why I was so nervous before. Could have been completely coincedental.

I reckon more excitement than nerves.

Either that or the idea caused you to overload.

@ therange: not all cougars are milfs, y'know. And DAMN, I wish there were guys like you in my neck of the woods!

@ therange:

1) Don't worry too much about this. If you try and force meeting a person you'll fall in love with, it probably won't happen. I know people tell me this about sex, but I think it's even more true here--because you can decide to have a sexual encounter with a woman provided she's willing, but you can't make your ideal woman just show up. And even if you fall in love, you may fall out of love down the line, either because your desires change or the initial feeling of being in love "runs its course".

2) I would think it would do the opposite, at least it would for me. Not being sexually frustrated makes it a lot easier to evaluate women on a personal level. If that isn't the case, you probably weren't looking for a relationship to begin with.

I'd be much more worried about her wanting to "be friends" afterward. Forgive me for being cynical, but this seems like a thread that may grow into a string, and then into a rope if you're not careful, and make it so you have to be really mean to her down the line to get her out of your life. I would be much more understanding of a desire to get to know you before the encounter (hey, I'd prefer that too), or to remain friends after the encounter if you already were friends before (again, something I'd want too).

I'm not trying to tell you not to take the opportunity, as I would certainly take it too. But just letting you know what I would be thinking.

I agree with the rest of your post but nah to the above, it's obvious it's just a casual sex thing. Think about it it'd be just as embarrassing for a 48 year old lady to introduce a 26 year old to her friends and family as it would be the other way round so I doubt she's after him in that sense. They both know it's just no strings sex which is why they both want to do it. Staying friends probably isn't what she wants but if it goes well she may want to keep in touch

Sex wont change you man don't worry about that. Might put a smile on your face and a bit of a bounce in your step but that's about it

Nah.

lol depends on your family I guess.

The only way it will change you is to give you more confidence with women. There is NOTHING like a hot 40 something woman. I don't think you'll regret it at all.

Dude, if I were you, I'd really think hard about what I was doing. I apologize if it sounds harsh, but I think an honest opinion would be of benefit to you.

First of all, what you are looking for is pity sex. Whatever you wrote on pletyoffish can probably be paraphrased as "I am a desperate loser who never had a girlfriend. But, I do not want to deal with any relationship pressure, potential humiliation, hassle of improving my skills and I do not want to pay for sex. So pleeese have some pity and let me use you once or twice ". This is as unattractive as it can be to any woman. What do you think this approach will get you? The only way this will succeed is if the woman has far more serious issues than you do.

Secondly, how do you know that the 48yo you have high hopes for is even real and not some sort of a scam devised for desperate guys like you? Even if you ever meet that person, you might be in for a surprise. The "attractive" one may turn into a 400lb godzilla with a host of problems you don't even want to know about. This is what happens when you scrape the bottom of the barrel.

How about a little gut feeling that tells you that you are doing a very stupid and a potentially dangerous thing. Listen to it, it's never wrong.

If you want to have sex that badly, just go and pay for it. It doesn't have to be illegal or expensive or dangerous, you can go overseas on vacation. And I don't mean going to some banana republic. For example, there are brothels in Germany that allow you to have as much sex as you want with any of their available women for a flat entry fee which is heavily discounted during slow periods. Many of them speak English so you can explain the situation and ask them to teach you some skills. Moreover, the profession there is regulated and the chances of getting an STD are small.

If you want a relationship, you need to think of if as separate from sex. To get it you'll need some skills. You will never get them by surfing plentyoffish or any other sites for years. Approach girls in real life and learn how to handle rejection. Read some books on the subject, get some friends/family to help you with some aspects such as clothing. Just try different things and see what works. If you fail a 1000 times, that means you now know which 1000 things that don't work.

AJY, if I didn't know any better, you sound like some NT wannabe jock guy you'd find on a pick-up site.

Did it ever occur to you that I want to have sex with an older woman because I'm physically attracted to them? This isn't some "Oh I need to get my virginity over with" thing.

And also, do you think I'm stupid enough to meet some woman I've never talked to on the phone or looks "too good to be true" hot? Her pics are quite ordinary...she's pretty, not a model.

Also don't appreciate the generalizations that I don't know how to dress or have never had a girlfriend. Both are incorrect. In fact, while I want another girlfriend eventually, I would like to know what I'm getting into with sex before putting all my eggs in one basket. The last thing I need is to become attached to some girl my age and within driving distance just because sex is great. Know too many men that went down that route and are now p**** whipped with some woman they don't even like for the rest of their lives.

I don't get why this is so terribly unattractive. Not every guy who hasn't had sex is a loser in every area of life, and while after being around the lock a few times he'll probably improve both his skills and confidence, but he has to start somewhere. I think more women should be understanding of that and just be like, "Hey, you seem like a nice guy, and I'm not in a relationship or looking for one, so let's you and me play a little".

But that gets back to the question of why sex with a somewhat less-than-desirable partner is such an awful thing for women. From the way they talk about it, most women seem they would rather help a guy out by buying/making him dinner for a week, or even, I don't know, allowing him to repeatedly poke her with a stick as part of an experiment, than even get naked in front of him. And sex is supposed to be fun!

That's another thing. My profile says nothing like that and I don't imply I'm looking for sex at all. I'm on there looking to get a date with a woman my age and from my location because I know people who've had success on it. I just happened to find her and talked to her at length before bringing up the fact that I'm a virgin.

Pity sex to me implies that the woman is not the least bit attracted to you but is having sex because she feels sorry for you. I'm sure it happens, but not that often. You think if I was some fat chubby kid with pimples she'd still be meeting me?

If this is true, shouldn't we all be getting lots of non-pity sex? Are there really that many women who aren't the least bit attracted to us? I barely have to walk more than a block from my apartment most days to run into a woman I'm at least decently attracted to.

No, it depends entirely on *me*.