My First Time with a Woman

Women's Dating

My First Time with a Woman

Katie B.
Katie B. Updated:

My personal journey around my sexual orientation has been kind of breathtaking, especially as I look back on it.

When J. and I opened up our relationship more than two years ago, I identified as straight.

I had grown up in an LGBTQ affirming religious community and was part of my Gay-Straight Alliance in high school.

I definitely identified as an ally to the LGBTQ community, but I never saw myself exploring sex with anyone other than a cisgender man.

Looking back on my life, I see the signs.

Growing up, I had many erotic dreams with women and had several close girl friends I had crushes on and felt sexual tension with.

Because liking guys was accepted, encouraged and assumed, I think I naturally gravitated toward exploring sex, love and romantic relationships with men since those attractions were apparent to me.

Opening up our relationship, especially within the swinger community, meant I had experimentation with women served to me on a delicious platter.

We first met Carly and Josh at our swingers club.

Carly identified as bisexual and was very attracted to me. I found her very sexy, although I didn’t yet feel “attracted to” another woman. I decided I was “bi-curious.”

On our second night at the swingers club, the four of us got a room together. We had same-room sex (J. and I had sex and Carly and Josh had sex, but there wasn’t any kind of “swapping”).

However, Carly and I kissed and made out and it was an incredibly arousing experience for me. Over the next couple of months, my sexual explorations with Carly increased.

I decided I was “bi-comfortable.” For me, this meant I was pretty much just attracted to men but found sex with women really hot during a group sex encounter.


“I desired both emotional and

physical intimacy with a woman.”

I desired to have sex one on one with a woman.

It needn’t be within the context of a romantic or dating relationship, and I didn’t think I wanted a romantic relationship with a woman.

Yet this differed from Carly’s comfort levels around sex with a woman: She was only comfortable and interested when it was during group sex. The contrast in our comfort levels and desires shed light on my interests.

A few months later, we met Laurel and Jordan, whom we saw individually and together.

I was able to explore having one-on-one sex with Laurel. It was really fun and satisfying, but the contrast in our desires shed light on my interests once again.

Laurel was only comfortable if our encounters stayed within the confines of casual sex. Dating, emotional intimacy and a romantic relationship was off the table for her.

I realized I wanted to date women, as I desired both emotional and physical intimacy with a woman. This was about the time I started identifying as bisexual.

I set out to find a girlfriend.

I met a few different girls off OkCupid, but it quickly became frustratingly apparent that it is just as hard for a girl to meet girls as it is for a guy to meet girls.

I felt desperate. For some reason, I just expected to find that awesome “click” with the first pretty girl I ran across.

Desperation is not a great way to frame up dating, by the way. It led to a number of awkward first dates, friend-zone-but-sort-of-romantic relationships and a really dramatic breakup.

I decided to put my quest to date women on hold.

When you are ready to meet someone, you will. This has been my mantra, and so far, I am more satisfied and happy with my experiences with women as of late.

Melissa found me on OKC a couple of months ago, and I am really happy dating her and exploring our relationship together.

Also, in the past six months or so, I have been identifying as queer instead of bisexual. I am attracted to not just cisgender men and women, but to transgender individuals as well.

I am attracted to masculine men, feminine women, soft butch women and androgynous women.

“Queer” more accurately describes my attractions and philosophy (I don’t believe in using a binary word to describe gender since I see it as a spectrum of identification and presentation).

I identify with the LGBTQ community as whole. I like the word “queer” over “bisexual” or “pansexual”- it sounds juicier and not so clinical.

In short, I am queer. Right now I have an amazing cisgender male primary partner and a kick-ass girlfriend.

Have you ever had a sexual experience with a woman? What was it like? How have your sexual interests changed or stayed the same because of it?

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