I'm a 31-year-old straight woman. I have a good job, great friends, and average attractiveness. I've dated close to 30 men at this point, and I can't wrap my head around this: I've never had a boyfriend or dated anyone for more than a couple months. It's really starting to wear on my self-esteem. I don't believe anything is wrong with me, but the more time goes on, the more I think I have to be doing something wrong. The guys ghost me or things fizzle out or we're not at the same point in our lives. This is particularly true for one guy I've remained friends with (common social circle) who is struggling with his career, though things are still awkward because it's clear there's still something there. Another area of concern: I'm still a virgin. Catholic guilt resulted in me being a late bloomer, with my first kiss at 21. Once I got more into dating, my low self-esteem coupled with the fact that I've basically decided I want to be in a monogamous committed relationship with a guy before having sex, relationships just never happened. I don't have unrealistic expectations that I'll marry the first dick that sticks itself into me—but I've waited this long, so I'm not going to jump into the sack with just anyone without knowing that I can at least trust them. The only guy I really do trust is Somewhat Depressed Guy, but propositioning him could further complicate our already awkward friendship. Is something wrong with me, and what the hell should I do?
What's Wrong With Me?
I get variations on the first half of your question — is something wrong with me?—all the time. But it's not a question I'm in a position to answer, WWWM, as I would need to depose a random sampling of the guys you've dated, interrogate your friends, and grill you under a bare lightbulb for a few days. And you know what? Nothing could be wrong with you.
As for the second half of your question ...
What the hell should you do? Well, gee. What you've been doing hasn't worked, WWWM, so maybe it's time to do something else. Like fuck some dude. Or better yet, go to Somewhat Depressed Guy and say, "I don't think you want a relationship right now, and I'm not sure I do either. But I like you and trust you, and I could really use your help."
While the commitment and monogamy approach has worked for some, it hasn't worked for you. And being a virgin at 31 isn't boosting your self-esteem. There are lots of people out there who jumped in the sack and did a little dick-sticking with people they barely knew but had a good feeling about. This approach doesn't always lead to committed and/or monogamous relationships, but it can.
Somewhat Depressed Guy might be somewhat less depressed if he was getting some, you might have higher self-esteem if you finally got some, and dispensing with your virginity might make dating after you part ways — if you part ways — seem a lot less fraught.
I've been with my boyfriend for more than a year. He's the first person I've had sex with. Four times now while we were having passionate sex, he has slipped out of my vagina and accidentally penetrated me anally. That shit hurts, and I can't help but cry. I know he feels super guilty each time. I love sex, but I'm kind of scared every time we have it now. We've engaged in a little anal play before, and I wasn't really a fan. But I'm not adverse to the idea of using a butt plug. Do you think this would work? Surely other people have this problem too, right?
Wrong Hole, Anal Torment
My own personal sexperience with anal led me to doubt claims of accidental anal penetration, WHAT, as anal penetration always required focus, precision, and breathing techniques. But I'm now convinced that accidental anal penetration is something too many women have sexperienced.
A strategically deployed butt plug sounds like a sexcellent solution to the problem, WHAT, but get yourself a plug with a wider-than-usual base to prevent your boyfriend's misdirected cock from pushing the plug, base and all, all the way in you or his misdirected cock from sliding in alongside the plug. (If you hate single penetration, you'll really hate double penetration.)
If the problem persists even with a plug, a thumbtack glued to the base of the plug will inspire your boyfriend to be more focused and precise.