Sex Column: Come Undone

Note: Due to the nature of this week’s question, this happens to be a vagina-centric article. I apologize if any penis owners feel excluded, but I encourage you to read it anyway!

Dear Tippy Maple,

I’m a pretty sexual person. I’ve had my fair share of partners and kinky experiences, and I’ve been an ardent masturbator ever since I was a little girl. Despite all this experience, I still have difficulty orgasming during sex, and (this is embarrassing to admit) knowing whether or not I’ve cum. Since I’ve brought this problem up to my boyfriend, he has been trying really hard to make me cum, which makes me doubt myself even more. Do you have any advice on how I can make sex with my boyfriend as satisfying as sex with myself?


Hopeless and Horny

Dear Hopeless and Horny,

First of all, good for you that you’re comfortable and experienced enough with your body to know how to satisfy yourself (which, ultimately, is more important than any other person knowing how to satisfy you!), but, understandably, it would be nice to be able to orgasm during sex. One problem that comes up when talking about sex with female-bodied people is which word to use—finish, orgasm, or cum—as they all have slightly different connotations. For convenience’s sake, throughout the course of this article I will discuss the female orgasm, and I will address the “cumming” issue at the end of the column. That being said, there could be a few things that are keeping you from fulfilling your frolics:

Like you, I’ve been masturbating since I was a little kid, and, even though this is mostly good, sometimes it can cause problems. Because you’ve been masturbating for so long, you may be limiting yourself in how you orgasm and the types of orgasms you have. I would recommend mixing up your masturbation routine. Buy a vibrator if you don’t already own one, or, if you do, buy a different type. Working solo on your orgasms will help you learn to orgasm in new positions and from different sensations.

And, now, to the second part of your question: on knowing whether or not you’ve orgasmed.

First, my two (feminist) cents: The entire idea of “finishing an orgasm” is a penis-centric concept and a bit Freudian, in that women are expected to “finish” by imitating the way men finish. Vaginas are built to orgasm in different ways than penises cum. Moreover, vaginas orgasm in different ways from one another; many orgasm in waves, others orgasm in one culminating moment, others experience cycles of build-up and then release of tension, and so on in infinite, different ways. It would be condescending if I told you what an orgasm should feel like or how long it should take you to orgasm—to each her own.

Second, recognize that the orgasms you have during sex might, and probably will, be different from the orgasms you have when you masturbate. When you have sex with someone else, you have new equipment in different places, so it makes sense that you might have a type of orgasm you have never experienced before, i.e. a much better one. (For example, I was a devout atheist until I had my first G-spot orgasm, then I decided there was a God after all.)

The “cum”nundrum: Regarding your query about “cumming” during sex, the excretion of discharge, or “squirting,” can be present in some female orgasms, although it is by no means necessary to indicate that you successfully orgasmed. Some vaginas can squirt, some can’t. Those that can don’t do it all the time, so even if you happen to be a “squirter,” you may not always have “evidence” that you came. If you’re curious as to whether you “squirt,” ask your partner to look out as they finger you or eat you out. If you do spunk your gunk, it will be easier for someone else to see/taste than for you to feel it.

And while it’s great that your boyfriend is invested in your orgasming, sometimes being pressured to orgasm only stresses you out and makes it impossible to achieve anything. Only when you stop worrying and doubting yourself will you be able to orgasm; it’ll “cum” when you’re least expecting it.

Happily horny,

Tippy Maple

*Winners of last week’s challenge—most exciting places where people have hooked up on the 5Cs:

1. Pitzer laundry room

2. Glass room on top of the Kravis Center

3. Stranger’s dorm room

New contest:

What is the kinkiest and/or most bizarre favor someone has asked you to do in the bedroom? (Note: It is not necessary that you completed said favor.) Anonymously submit your answer (and any other sex questions you may have) to:

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