I’m dating a Catholic virgin (both of us are professional adults). We’re going to have sex soon, and I want to make it good for her, but I’m not very experienced myself and I’m both long and thick; I have to buy custom condoms because nothing store-bought fits. Worse, I have a pronounced downward bend; it caused problems with my first-ever girlfriend, and that left a lasting impression on me. I really don’t want to ruin this for her; do you have any advice?
The most important advice I can give you about this is, DON’T RUSH. If she’s a virgin your size may scare her at first, so you need to be ready for that possibility. If it happens, you need to sincerely tell her that it’s not a rush, and you have to mean it so she sees it in your eyes and believes you. Start with fingers and oral, to get her ready before you even try; if she has an aversion to fingers, try gently explaining that you’re concerned about hurting her so you want to take it slow & get her ready. The vagina can take a LOT more than any human man has; lesbians often fist each other (which even though women’s hands are smaller than men’s, are still MUCH thicker than penises). Plus, babies, right? But that’s after warmup and relaxation. So anything you can do to help her relax is a bonus; a few cocktails (you don’t want her drunk, just relaxed) or some good cannabis are time-tested methods. When you do start the actual penetration process, don’t be in a rush; a little at a time, with kissing and touching, will help her to stay calm and relaxed. And make sure you have plenty of water-based lube on hand; women vary in the amount they lubricate naturally, and if she’s nervous she may be drier than under optimal conditions. Plus, condoms require more lube than bareback sex; the latex produces more friction than bare skin. If she does get scared and changes her mind, don’t get angry; that isn’t uncommon. Just gently withdraw and assure her that it’s OK, and that y’all can try again another time (again, you need to mean it because she’ll know if you’re just saying it).
Just because she’s a virgin does not mean she’ll be super-tight; women’s genitalia come in all sizes just as men’s do, so once she gets over the nervousness you may fit quite well. And it’s a myth that a lot of sex loosens a woman; after 36 years of sex I’m still extremely tight. What some guys mistake for loosening is just the woman learning to relax, which of course increases with experience (childbirth can also damage the muscles, but that’s a subject for another day). It’s possible that your angle may cause an issue, especially if it’s pronounced; you may need to try a couple of different positions to see which one works best for her. Reverse cowgirl (woman on top, facing the man’s feet) can be good for penises with a pronounced downward bend, and that has the bonus of letting her control the rate and depth; of course, that also results in deper penetration, which is not so good for a long cock. So you’ll probably need to experiment to see what’s best. Incidentally, I believe there has been some progress in the treatment of Peyronie’s Syndrome (that’s what the pronounced bend is called), so you may want to talk to your doctor for referral to a specialist for consultation.
Finally, and VERY importantly, do not worry about your skill level. Really, honestly, that is of little to no consequence to most women. What’s important is that you be loving, gentle and patient; that you listen to what she says and watch her nonverbal cues about what feels good and what doesn’t; that you make her feel beautiful, desirable and loved, and not pressured or inadequate; and that you help her understand that more than anything else you want intimacy with her, specifically, and not just any attractive woman. And that because of that last, you’re willing to take your time and do whatever it takes to make her happy and comfortable.
(Have a question of your own? Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)
