Dear Alice,

I have encountered a problem I never expected; my boyfriend is quite simply very large. I am unable to perform oral sex except for the first couple of inches due to the girth, and vaginal sex is not totally satisfying for him because he is too long and cannot fully penetrate without causing me significant pain. I've seen my doctor, and am reassured that there is physically nothing wrong with me — no infections or scarring, but am finding it difficult to come up with a solution. Any suggestions?

Too Shallow?

Dear Too Shallow?,

Contrary to the popular belief that "bigger is better," oral sex, anal sex, or vaginal intercourse with a particularly well-endowed man can present challenges. The great thing about being intimate with someone else, though, is that there are endless amounts of ways to get down and dirty. You and your boyfriend will just need to take some time to communicate and get creative. If you do that, you are sure to stumble across a few (or a bunch) of mutually satisfying solutions. Make note of these four words: arousal, lubrication, position, and technique. Let’s discuss a few different suggestions to try:  

  • Arousal and lubrication. Regardless of penis size, sensual touching is essential before penetration as it allows enough time for arousal as well as vaginal lubrication (also see First sex for two virgins?). Have you ever heard of vaginal tenting? It’s a (pretty cool) process that occurs during sexual arousal where muscular tension pulls the uterus upward, which can create more length and width in the vagina. The average vagina is about 3-4 inches in length, but can reach 5-6 inches in length as a result of vaginal tenting. Spending more time on foreplay can build your arousal prior to penetration, and allow your vagina more time for tenting. Adding some water-based lube to your sex play may also make sex more pleasurable and less painful.
  • Position. You mention pain when your boyfriend tries to penetrate you fully. The discomfort may be due to the head of his penis hitting your cervix (check out Curious About Her Body — What is my penis hitting? and Where does the penis go for intercourse? for more information). Different sexual positions could help reduce pain and increase your pleasure, such as those that allow you to have control over penetration and movement (e.g., being on top). You could also try out different positions for having oral sex such as with your boyfriend lying down, standing up, on his knees, or sitting. Maybe one of these angles would make you more comfortable with performing oral sex.
  • Technique. Some people feel more comfortable with partial insertion during oral, anal, and vaginal sex. The unenveloped part of the penis, as well as the scrotum or anus, can be stimulated with fingers, hands, or a vibrator. Oral sex doesn’t always have to include taking the penis fully into the mouth or fully into the vagina. While the Latin term for oral sex on a man, fellatio, means, "to suck," oral sex on part or along all of a penis (think corncob) involves caressing with the lips, tongue, mouth, breath, and fingers, together. Try using your hands on the base of the penis to stroke the part of the shaft that isn’t in your mouth when having oral sex.

As you experiment and play, tell one another how you feel, what is uncomfortable, and what feels good. This doesn't need to mean carrying out a full conversation while having sex; simple words — like "deeper" or "not so deep," "gently" or "harder," "faster" or "slower" — usually are enough to get the point across and make sex more satisfying for both of you. As you embark on your expedition, don’t forget safer sex supplies. Peace of mind is also a key ingredient for pleasurable sex. If you are a Columbia student, take a gander at the safer sex supplies map for the provisions located closest to you.

Have fun,

Alice!
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