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Hookup Help: Watching Her Masturbate

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Q: Dear Holly. I’ve been seeing a woman I met online for about three months. The sex is passionate, loving, and adventurous. I love watching a woman masturbate but my lady seems a bit shy to do this in front of me. I know she masturbates regularly on her own, so how do I convince her let me watch the show? – Erin

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A: Hi Erin. Great question! From my own experiences, you’re not alone. Many of my lovers have wanted to watch me play with myself. When I was younger I too felt self-conscious about doing this in front of a partner. Hell, I didn’t even start masturbating until I was in my early thirties!

I brought up this subject at my recent Ladies Night to get some feedback and thoughts on what makes a woman comfortable enough to indulge this fantasy for a partner.

Tips for Watching Your Girlfriend Masturbate

Do it first. Ask your lover if you can masturbate in front of her… or just start and see how she reacts. I love watching a man play with his package. It’s the best way to learn the strokes and pacing he prefers.

Do it together. This can be such a turn on and challenge. Make it your individual goals to reach climax and orgasm at the same time.

Watch porn together. She might do this when she is alone, so it may feel more natural for her. And this can take the focus of her (or so she thinks) while you get a two-for-one show.

Give her a toy. Most women already own a vibrator or dildo that they use to masturbate with, but if she doesn’t— give her one.

Show your appreciation. Don’t just lie beside her like a wet noodle—get involved! Touch her breasts, suck her nipples, stroke her hair, kiss her neck… and tell her how much it turns you on watching her play with her pussy.

Make her cum again. After she orgasms on her own, make it your mission to give her a second if not third orgasm. You’re likely already hard and ready to go, so put her in her favorite position and work your magic.

Hookup Help is a Q&A series. If you want advice or a female’s perspective on hooking up, online dating, relationships, or sex… we want to hear from you. SUBMIT YOUR QUESTION, and who knows, you may appear in the next Hookup Land newsletter. -xo Holly and Tia

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