The Hook Up: Painful sex and ditching a rebound who won’t take the hint

Photo: Deux/Getty Images

Photo: Deux/Getty Images

Editor’s Note: This article was first published on AfterEllen in 2014 as part of an ongoing series called “The Hook Up” by Anna Pulley. The advice is just as relevant today, of course. Please comment to let us know if you’re interested in seeing a similar relationship/sex advice column  on AE in the future. 

Anna, My partner and I have been together for about 10 years, neither of us has ever slept with a guy and we have only experimented with toys a few times, rather unsuccessfully. We tried to make a go of it the other night but didn’t get very farliterallybecause it was rather painful for both of us. We use smaller than average toys so I don’t think that’s the problem.

Here’s my question: She and I were talking about it afterwards and we were like, “Are we that small or are we just being pu$$ies (pardon the pun) about the pain?” I have never heard my straight friends talk about how painful it is, especially the first time, which I would assume has to be painful for most everyone. It’s not that we can’t be together in other ways, of course we definitely do. It’s just that I’ve never had a vaginal orgasm and I’d like to get past the painful part to the fun part. I guess I’m just curious if I’m in the majority or minority that think it’s kind of difficult to get past the pain.—Tiny

Anna says: Dear Tiny, Vaginal sex should never hurt if you’re being mindful of your body’s needs and limitations. Sex pain isn’t something to be endured or tolerated, like dental surgery or watching season six of The L Word.

It’s true that the first few times women experience vaginal penetration, it could result in pain or bleeding (though more often it does not) due to the “breaking” of the hymen (it’s more of a wearing away of the membranes/tissues. For more on hymens, read this.) Most of the time, however, the pain associated with first intercourse stems from lack of lubrication or not being aroused enough. I would venture a guess that, since you and your girlfriend have been boning for 10 years, you’ve probably used fingers at some point, meaning you’ve experienced penetration before and that we can rule out hymen-related pain.

“Sex pain isn’t something to be endured or tolerated, like dental surgery or watching season six of The L Word.”

It’s possible also that even “smaller than average” toys might be too much for you, and that you might need to experiment with shorter or thinner implements, different shapes, and materials. Try toys that are made of more yielding materials like flexible silicon or cyberskin, instead of ones made of glass, metal, or god forbid, plastic. Also, be sure whoever is being penetrated is nice and warmed up before you go spelunking with a dildo. Start with a lubed-up finger (trim your nails or use gloves!). If that feels OK, add another one. Apply lube as needed and make sure you’re not neglecting the clit or other erogenous zones. The more turned on she is, the better.

Once the receiver feels ready for the toy, you might STILL need to experiment with positions. Some angles and positions are better than others when it comes to depth of penetration, hip flexibility, and overall body structure. Honestly, it can even depend on the day. Some days a reverse cowgirl feels impossible and other days, it’s like, giddy up. Play around with it. One girl’s missionary position is another girl’s anxious wallabyyou never know what might feel awesome or terrible until you try it. And again, if something hurts, especially any sharp or stinging pain, stop. Try something else. The last thing you want is internal bleeding or tearing.

I’d also like to point out that it’s pretty rare for women to come from vaginal intercourse alone (about 75 percent of all women can’t). This isn’t to discourage you and your partner from experimenting with toys, strap-ons, whatever. Just to remind you that, should you not achieve the elusive and Freudian orgasm, you shouldn’t despair. It’s no easy feat, even with the aid of a perfectly tailored vibrating jelly double dong.

Aaaaand here comes the ol’ advice columnist PSA: If after trying all these things, you are still experiencing pain, you might need to call a doctor. There are some physical medical conditions that exist, like vaginismus or dyspareunia, and some psychological factors that might be contributing to painful vaginal intercourse. Those are rarer cases, but not impossible, and are often manageable with the help of a medical professional.

Good luck, Tiny! May your ambitions be ever larger than your name sign-off.

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