He says that she could cum from him cumming in her ass. I’ve only done anal twice before (with the same person), and he spent several sessions working up to it (fingers, then toys). Once I got past the initial twinge of pain/discomfort, I enjoyed the feeling, and I am not averse to trying it again with my current boyfriend. The problem is that he doesn’t really like foreplay, and even though I’ve suggested that he could start using fingers to work up to the point of penis-in-ass penetration, he’s shrugged off my suggestions and just said, “don’t worry about it, we can do it some other time.” I truly think he doesn’t believe me when I tell him how much it hurts for most women because the last girl he was with apparently was down to do it anytime, any place. Do you have any suggestions regarding how I could possibly make him understand that despite his past experience, most women need to build up to having anal so that it doesn’t cause extreme pain?
Sweet girl, you’re not just missing the point… you’re missing several of them. You are, in fact, comprehensively missing all of the points.
- He’s not-so-subtly taunting you with tales of an ex with an invincible asshole. Now, in a relationship with me, that’d be pretty normal… a girl of mine wakes up every morning knowing this may be one of those days when I decide to aggressively remind her that she’s fungible. But he’s not me, and you’ve said nothing to indicate you’re anything but an odd girl with odd taste in blogs… so that means he’s just being a coercive dick to a nervous partner.
- In fairness to him, “not averse to trying it again” is a looooooong way from Little Miss Magic Colon. Assuming he’s telling the truth about her, he was probably turned on by her eager, hungry attitude as much as the fucking itself… and while you can give him your ass, I doubt you can give him the parts that really matter. So if you intend to pursue experimentation with him, make sure you’re doing it for you.
- “He doesn’t really like foreplay.” Welcome to Crazy Bedtime’s Problematic Party-Favor and Red Flag Emporium! I see you’re a knowledgable customer, based on the man-sized crimson wall-hanging you’re dragging through my store. Just pile it over there and give it your phone so it can play Fortnite while we talk business. … Okay, now that we’re out of earshot of the Scarlet Speedster over there… heads up, dummy. If he doesn’t like foreplay, he probably doesn’t like you. You’re a hole to him. Does that make you wet? Awesome! But if it doesn’t… that’s probably a significant concern. Take steps.
- The “don’t worry about it response” can be interpreted two ways, depending on the validity of observation #2 above. Either he’s trying to guilt you into something —is he pressuring you to endure an assault on Mount Ass, or is most of the conversation initiated by you out of insecurity?— or he’s genuinely disinterested in the prospect of “dirty, taboo sex” with someone who isn’t a gung-ho freak about it. (Issue #3 is what makes me believe it’s the former, for the record.)
- If you truly think this is a matter of questionable assumptions based on limited experience, then the path forward is obvious… buy the smallest, smoothest, least-penis-looking anal vibe you can find, and tell him to give it a try. One of two things will happen: he’ll yelp a lot and (gingerly) walk away a more sympathetic man, or he’ll get hip to the benefits of a warm-up and you’ll be trying it out next. Or, well, of course he could go with the Special Bonus Option and tell you to go fuck yourself. But then you’ve got a boy who doesn’t listen, doesn’t like you, and doesn’t care, at which point you need to be a girl who doesn’t put up with his shit.