32 [M4M] First Time With a Woman: Bisexual Roleplay

NSFWM 4 M

I am a bisexual male looking for another bisexual male to do a long term roleplay with me. This scenario will be have gay, bisexual and straight elements. It will involve us playing versions of ourselves, and two additional female characters who we can base off of porn stars. Ultimately, this scene will be about the two of us watching one another explore our first times with a woman, step by step.

You and I are a happily committed, monogamous gay couple, we could be boyfriends or husbands, whichever you’d prefer… but we’ve been together for quite a few years and are well cemented in our relationship. More recently, our bi curious sides have come out… we’ve been watching more bisexual porn together and it’s been turning us both on. Neither of us has been intimate with a woman before. One night when we’re relaxing, I confess that I’d like to try having straight sex with a woman, and you confess the same. After this, we also have a thoughtful discussion about everything we want to try.

We decide to reach out to two women who we’re fairly well acquainted with, friends, coworkers, or neighbors who we find slightly attractive. We explain our situation with these women, and they know we’re married and want to try this together, so it’s not awkward. They’re very open to taking things slow, taking it one thing at a time, letting us give in to our curiosities and discoveries.

This leads to you and I having some deep conversations as a couple, wondering how it’s going to go… because there is some nervousness. We decide that this can be a weekend long affair, for two nights. The first night is us in a room with two double beds, one for each of us, as we follow the same rhythm, step by step, having sex with a woman for the first time. Each of us watching one another and turned on seeing our partner do this. The second night will be us in separate rooms, alone with our woman, away from our partner, exploring on our own. During this experience, both of us learning and embracing this new side of ourselves.

I’m very open as to how things can go and some of the details. I am into deep romantic roleplay, as well as pregnancy risk, so very open to that. I would like this to be a long term scenario. I am very kink friendly and pretty open minded! Please be open minded and be able to carry a conversation.

Posted Apr 7, 2026, 11:32 AM UTC · locked

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