A
female
age
36-40,
anonymous
writes:(sorry this is kind of long!)A friend of mine from high school reconnected with me about a year ago. We went on a few dates before he suddenly (and it was definitely sudden) revealed that he didn't want to be in a relationship. At that point I was totally crushing on him and really taken aback and hurt by his sudden change of mind as the whole thing was his idea to begin with. (to this day I still don't know what happened) I eventually *mostly* got over it and we continued seeing each other on occasion and making out. After the summer we started to see each other almost weekly and the make-out sessions went further and further and lead to oral and digital play. I always stopped it before penetration. Now it's getting close to impossible to fight our sexual chemistry. I try to make our meetings not-so-regular but then when we finally do get together it's 10 times more intense. Recently I've been considering going all the way with him. The reason why I was so reluctant before was that he would be my first. I'm not sure why I waited so long (I think all the years of listening to Dr.Drew go on and on about STDs on Loveline scarred me for life), but now I feel like I'm finally ready for real sex. The issue is this guy and I aren't even dating. I don't think he's hooking up with anyone else, but I don't really know. It would be one thing if I was 16, but to wait 24 years and hold off several boyfriends only to lose it to someone I'm casually hooking up with? What if he stops talking to me? I'm not some silly teenager looking to sex to get him to love me, I want to have sex with him because I feel comfortable with him (I've known him for yeeears) and we have a great chemistry in and out of the bedroom but what impact will his have long-term? If I weren't a virgin it wouldn't be up for discussion, but should you plan for a first time that you know isn't really going to be special? Or has society given me a f-ed up version of what special really is?
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female
reader, msdgaf910 +, writes (17 February 2009):
 i think you're old enough to make the decision you want to make. if you are that comfortable with him, let him know, tell him this is my first time, and really i don't know what to feel about it. ask are you seeing someone else? is there anything i should be worried about? are you clean.... but talk to him, while things arent heated up between yall. and sex isnt the rose pedals, love story, we should be together to have sex, cause most of the time, it's not even close, and not everyones first time is that perfect dream as we hoped to be, yeah it could be but... lets get back into reality. reminder; don't do it unless you know you are ready.
A
reader, anonymous, writes (17 February 2009): Wow, that's a tough one. Here's some things to consider. Sex can be pretty emotional for a lot of women. If you have sex with him and that deepens your feelings for him, then what happens to you if he goes off and starts dating (or worse sleeping) with another girl? If you have romantic feelings for him, I can only imagine this situation hurting you in the long run - if what you want is a relationship with him. If you really and truly feel like you'll be fine not having a relationship with him, then it sounds like the sex would be great and satisfying. But I would caution you because it sounds to me like you would get more emotionally involved with him. Have you thought about discussing a committed relationship with him in the context of telling him that you'd like to have sex, but don't want to be just his toy? It'd be interesting to see what he says to that. Best wishes!
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