I'm a straight woman in my early 30's. I was a late sexual bloomer, having intercourse the first time a few months ago. Unfortunately it turned out like a morality tale churches tell you to scare you into abstinence. He was extremely physically rough despite my protestations, and actually ripped me open and I bled quite a lot. (Still bleeding occasionally.) He promptly dumped me the next week.

That was my only experience with intercourse. Now I'm dating someone new and of course want the chance to have a much better experience, but I'm nervous. I feel like being past 30 with one terrible sexual experience to my name is even more hard to explain than being an older virgin. Also, I don't know how to emphasize the importance of being gentle with me the first time (or however long it takes to adjust).

The guy I'm dating is great and I have no reason to believe he'd do what the last guy did, but I just would appreciate some tips in how to have this conversation and keep communication open.

Gun Shy

My response after the jump...

••••••••••••••••••••••••••

You think the new guy you're dating is great, GS, but you probably thought the the last guy you were dating was great too. Since you were wrong about Last Guy, GS, and it's possible you're wrong about New Guy.
But there's an easy to determine if you're right NG. Tell him what happened with the last guy and see how he reacts. If NG freaks out or blames you or acts like this is all about him—if he gets upset at the thought of having to be considerate and gentle because considerate and gentle just aren't his style—then guess what? New Guy isn't a great guy and you shouldn't fuck him.

If, on the other hand, NG reacts like a decent human being—if he listens sympathetically, if he tells you that's awful, if he apologizes on behalf of the males—then NG is a good-and-possibly-great guy and you should fuck him.

I understand why you're hesitant to tell NG what happened: you don't want to seem like damaged goods and/or come across as so fragile that you'll fall to pieces the next time a guy fucks you. But you do have some damage—you're still bleeding (have you seen a doc?)—and your first experience with penetrative sex was so unpleasant that there is a chance, likely a small one, that you'll get upset and need to take a break or call the whole thing off. You're less likely to fall apart, however, if NG is being gentle, if he's taking it slow, and if he's checking in with you throughout—all things he's likelier to be doing if you tell him the truth. And if you think NG might be a longterm prospect, GS, it's better to exceed expectations with a smooth experience the first time than to surprise him with a meltdown.

One final bit of advice, GS: don't have vaginal intercourse the first time you have sex with NG. Just take it right off the menu. Tell him you're ready to get naked with him, tell him you can't wait to get off with him, but the first time or two—or three or four—it's gonna be oral and mutual masturbation. That will take the pressure off you, GS, while giving your girl bits more time to recover. Even better: unless he's some sort of Jekyll & Hyde freak who becomes a totally different person during vaginal intercourse—which seems highly unlikely—you'll have a much better idea about the kind of lover he is when you are ready to give penis-in-vagina sex another go. You may still be anxious, GS, but you won't be as anxious.

Good luck—and, hey, on behalf of the males: I'm sorry about the last guy you were dating. What an asshole.