I decided to wait almost a month to sleep with my newest boyfriend, rather than doing the typical “third date put-out.” I'm starting to wish that I'd gone ahead and slept with him, because even though he's a great guy who tries really hard in the sack to please me, he's got way too much tool for me to handle. I mean, there's “well endowed,” and then there's this guy. I've never had this problem before, and to be honest I never thought that something like this could be a problem! Let's just say that those things work best on paper. Sex is very uncomfortable to the point of not being enjoyable, and I can tell the poor guy's had this issue before, because he likes to spend a lot of time on foreplay before we get to actual intercourse. It doesn't matter how long, though, because every time it just hurts.
I really never thought this could be a bad thing! I like him and don't wanna break up, obviously, but I certainly can't handle sex with him. Are there things I can do to make sex more comfortable for me?
I had this same problem a few years ago, actually. Vaginas can accommodate babies, so of course they can handle well-endowed penises, but it's incredibly important that you be sure to have plenty of foreplay and be appropriately “in the mood” so that your body will be receptive and adjust itself accordingly. Don't be embarrassed to use over-the-counter lubricants, either. You wouldn't believe how many women I've spoken to who refuse lube as a point of pride about their own body's natural processes, but don't be a hero. Use a hypoallergenic brand, and I personally prefer water-based lubricants.
It seems like you two are already spending lots of time on foreplay, so maybe he really is TOO big. In that case, a practical thing you can do is be the one on top when you're intimate. I'm certain that your dude doesn't want to cause you pain or injury, but he can easily wield that thing in a way that could cause actual harm to your body. Just go slow and make sure that your body is absolutely ready to receive this guy, and this problem should fix itself!
I've been hanging out with this guy for about a month now, and I thought everything was going great. Sex is good and plentiful, and we see each other enough while still getting plenty of private time. I'm starting to regret our super-casual arrangement now, because I've basically discovered that he's got another girlfriend running around this town. I mean, he's sort of just “talking” to this other chick, but from what I can tell she gets as much of his time and attention as I do. I didn't know about him and this girl at all, but through snooping around I've learned that they've had an on-and-off thing for quite a while now. Am I getting cheated on, or am I actually the side chick? I confronted him, and he treated me like I was crazy for getting so serious about him, and it really hurt my feelings. He says that we were never that serious, and that's why he didn't tell me about the other girl. I just don't know what to do, because I want this guy, and I'm tired of losing men to other women.
Pick up your phone right now and dump this piece of crap via text message. Welcome to Athens, where boys don't commit in order to be able to sleep with a smorgasbord of local tail and give us all HPV. It sounds like you're the side chick more than the main, but either way, you want monogamy, and this guy is flat-out refusing. When you mentioned how great the relationship was, your only evidence to that was sex. This relationship doesn't sound like it's worth much to him or to you, beyond the pride of being able to say you're in one. But he doesn't even want that, does he?
Dump him and move on. Go find you a loyal man with too much penis. Now that's a good problem if I ever heard of one.