Happy young couple relaxing in home bedroom after waking up in the morning

My girlfriend and I have been dating for over 6 years, we’re both each other’s first, and we’ve taken things fairly slow because of how young we started dating (in freshman year of high school). This is especially true for penetrative sex, which we’ve only tried recently. The few times we’ve tried it’s been uncomfortable and even painful for her to take even a little bit of me. I am above average in both size and girth, which makes it challenging for her to accommodate me. We’ve found the right condom size for me, used (what we thought was enough) lube, and tried to lead up to it with enough foreplay, but it’s still uncomfortable. I think that part of the issue is nervousness and the place/time we’ve been able to try (we both live with our parents when we’re not apart from each other at different colleges).She would like to try and use sex toys to get used to penetration and work up to being able to take me. I’m not sure whether to buy just one that she can use, or multiple ones ranging in size. Any advice about our problems would be much appreciated! Thank you!


  • Michael Castleman says:

    I applaud the very conscious, loving way the two of you have explored sex together. Bravo!

    About her pain during intercourse: Have you ever heard of vaginismus? It’s a medical condition involving spasm of the vaginal muscles that partially or totally close the opening, making insertions of erections, toys, and even fingers and tampons difficult or impossible, even with lube. So first, I urge your girlfriend to consult a gynecologist and see if she has vaginismus. If she does, it can be treated, ideally by a physician well schooled in sexual medicine working with a sex therapist. To find a doctor near you who specializes in sexual medicine, visit the North American Society for Sexual Medicine. Vaginismus treatment usually includes a few months of inserting graduated dildos—from small to larger—to get the vaginal musculature used to accommodating things.

    If it’s not vaginismus, then you may be correct about nervousness/anxiety. My suggestions: Before getting sexual, she should relax deeply. She might meditate or take a hot bath or shower, or both. Then before attempting insertion, enjoy at least 20 minutes of leisurely, playful, gentle kissing, hugging, cuddling, and mutual whole-body massage, which are great warm-ups for lovemaking, especially for women. If your two sex venues are one of your homes with parents possibly nearby or one of your college rooms with roommates and others possibly nearby, lack of privacy may increase anxieties. Try to find a place where you can enjoy total privacy, for example, a friend’s home or college room when no one is home. Or consider a budget hotel.

    If your issue of pain on insertion has been going on for a while, like many months, it’s also quite possible that your girlfriend has develop a conditioned reflex. Attempts at insertion were painful … so she expects future attempts to be painful … and they are. You might consider consulting a sex therapist about this. To find one near you, visit the American Association of Sex Educators, Counselors, and Therapists. Sex therapy isn’t cheap, but given your age, you may be able to negotiate low-cost therapy.

    I don’t know how you came to the conclusion that your penis is larger than average—only about 5 percent off men are. If you are on the large side and she has an vaginismus, then the former would aggravate the latter, and she should definitely see a doctor.

    Finally, speaking of nervousness, you got together around age 14 and now you’re around 20. It’s great that you’ve stayed together so long. But I’m guessing you began your erotic play before either of you knew much about sex and lovemaking. You’re older now than you were as young high schoolers, but you may not be much wiser about sex. That’s why I suggest you consider my low-cost e-book, Enjoy the Best Sex of Your Life. Its 135 chapters discuss all aspects of lovemaking. Systematic knowledge of sex can help you both relax and feel more confident in bed. And my e-book carries a money-back guarantee through PayPal, so it’s risk-free.

    I wish you great—and pain-free—sex.

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