Advice for Watching Your Trans Girlfriend with another Woman

Dear Jamie,

My transgender girlfriend and I are pretty kinky—we enjoy bondage and discipline, pegging, masturbation shows, and role playing. We’re monogamous, but Helena has sometimes expressed fantasies and desires to be with other women. She has asked if I would be interested in watching her make love to a woman. I’m willing, of course—what man wouldn’t want that? But I’m not sure how to act, or what to do or say. – William

Congratulations, William, on the sensational times ahead in your TMF threesome! Here are a few tips for watching your trans girlfriend make love with another woman.

The first thing you’ll want to know or help determine is what level of participation you’ll have. If you will be asked to join in, you’ll want to know that ahead of time and know that both ladies are on board with that in advance.

Ditto goes for whether it’s “for your eyes only,” or if you’ll be masturbating during the show.

You don’t want to pull out your dick if you don’t have the consent of Helena’s paramour, even if you don’t touch her or them.

Once those basics of consent have been established, sit back, relax, and make the most of your lucky day!

Make sure you make Helena, and her date, feel comfortable and not awkward. Don’t make it all about you and your comfort, but focus on their enjoyment and experience.

Don’t dictate or direct. You might want to see more oral, or more kissing, or more of her penis, but unless they have expressed a particular turn on for following your fantasy, go with their flow.

Be supportive of Helena’s choice of lovers. She’s the one who brought up the subject. Don’t ask her to compromise on her fantasy for yours. Let her make the connection she sees fit with a female lover. If you’re a die-hard trans admirer, you might hope she’ll hook up with another t-girl, but she might be dreaming of licking a cis pussy or just experiencing what a cis woman feels like physically. Let it be her dream that comes true.

Don’t act strange after everyone’s orgasm. Voyeurism, group sex, and threesomes are always a lot of fun—fun that is sometimes followed by an awkwardness that sets in after the sex is over. Don’t come down from the heights of horny with moody, possessive or angry vibes. If you’re genuinely feeling strange afterwards, connect with your lover by being honest about that with her.

Do your part before and after to make the set-up and setting sensual and comfortable for your guests. Have clean sheets and towels on hand, and scrub the tub. Keep a basket of travel-sized soaps and any other goodies you can think of for your visitors.

If you’re going to her place, bring both ladies flowers or a bottle of wine as a gesture of gratitude, and come scrubbed and flossed with a change of clothes.

You can’t go wrong by making everyone comfortable after the fact with the suggestion of sharing a pizza or making up a killer fruit salad. Offer the other woman a ride home or a taxi, and then spend quality time with your girl.

Are threesomes a fantasy for you or your lover? Any tips to share? Leave a comment!

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