Stoya On Infidelity & Dating Younger

We love chatting with Stoya — writer, thinker, on-screen-sex haver — about all manner of sexual, sensual, and feminist topics. In fact, we had so much fun talking with her that we asked her to write a monthly sex and relationship advice column. Have a burning question? Send any and all queries to
I’m 22 years old. Some time ago, I was dating this amazing, 36-year-old, big-ass woman, and the sex was INCREDIBLE. We would fuck on the bed or standing up with her hands on the wall. We even had sex in a mall! It was amazing, and she was able to turn me on in seconds!
Nowadays, I'm dating another amazing girl. She's 20 years old and does everything for me — everything. We both agree that our sex is not the greatest in the world, but when we started dating, I knew she was a virgin. I have much more experience than she does, and it's my job to advise her on things I like and things that maybe we will both like. I believe in "ladies first" and try to make her come every time we have sex.

But, our sex positions are getting too repetitive, and sometimes when I go too deep and hard, she feels pain. Sometimes I regret breaking up with the 36-year-old woman, but I love my girlfriend. Do you have any advice on what we could do to spice things up a bit?

— G

Since you and the 36-year-old woman are no longer dating, I’m certain there is some reason the two of you broke up. Take a couple minutes to remember that reason, and then put this comparison between her and your current girlfriend out of your head for good.
I agree that it's your job to express your sexual desires and needs to your girlfriend. However, unless it’s part of a mutually agreed-upon power dynamic, your young and sexually inexperienced girlfriend is not a puppet to train to your liking. It’s only your job to ask what she wants and needs, to actively listen, and to try to give her those things, as long as they don’t violate your boundaries.
You get to make a choice here between being the guy who stunted her sexual growth by imposing his ideas about what she might like on her or being the guy who is a fantastic partner while she explores and discovers new things about her sexuality. Be the second guy.
If you give her the space to be curious, you have the opportunity to foster feelings of safety and trust. The safer and more trusting people feel in sexual relationships, the more open and relaxed they tend to be. She’ll probably feel more comfortable sharing her desires with you, and she may become more physically comfortable as well. This is likely to lead to more natural variety and novelty in your sex life.
In the meantime — and in case deep-and-hard penetration remains out of her comfort zone forever — there are a few things you can do: Work on training your body to require less pounding for sexual satisfaction. If your masturbation routine habitually ends with rapid and aggressive strokes, take a long break from it. Focus on other sensations that also feel good.
Another thing you can do is wrap your hand around the base of your penis during penetrative sex. Or, ask your partner to use her hand. This works like the opposite of a penis extension sleeve. Instead of making your penis longer, it provides a few inches for you to thrust into without hurting her.

I'm having a lot of trouble with men, and I need help. I've always dated men who were five to 10 years older and usually NOT single. Now, I'm very much in love with a guy who says he's in love with both his actual girlfriend and me. I'm always forgiving him for his lies or false promises. But, I'm definitely not happy. It's hard to let it go and hard to be free. I mean, the sex is really good.

— C

You didn’t mention if the partners of these not-single men are aware they’re dating you. If their partners don’t know, stop doing that. Whether the agreement between people in a relationship is to always wear one yellow sock or to never physically touch another person, knowingly participating in the violation of that agreement is morally dodgy territory. Incredibly dodgy.
Now that you’ve developed an emotional attachment to one of these men, he’s lying to you and breaking promises. I’m working off the assumption that his girlfriend doesn’t know about you, but if he’s being less than honest with his girlfriend — and also lying to you — then you’re almost certainly setting yourself up for disappointment by expecting him to change. Even if his girlfriend does know about you, and the secondary relationship is completely okay within the boundaries of their agreement, he’s still lying to you and breaking promises. Everyone deserves to be treated better than that.
I know really good sex can be hard to walk away from. And, I know emotional attachment can be hard to walk away from too. But, my advice is that you walk away.
Tell him you’re finished and don’t look back. And, on the day you do that, mark your calendar for exactly six months in the future. For those six months, do not date, flirt with, or have sex with anyone but yourself. The idea of being alone can be terrifying, but getting through that fear and developing confidence in your own independence will give you freedom.
You should also stay sober during this time. The sobriety will help make sure you don’t spend those six months numbing your feelings accidentally. Learn how to have really good sex with yourself — super-great-fantastic sex even. Put all the energy you’d normally spend on dating and sexual relationships into something else that makes you happy, accomplished, or good, like your career or learning a new skill.
Finally, do some introspection about what you want from relationships and what your needs are. When those six months are over, open yourself up to romantic and sexual involvement when you feel ready. Just stay out of that morally dodgy territory of enabling infidelity.

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