I Had Sex with a Woman — And I Want a Do-Over

I’m reminded of it every New Year’s Eve

My sexual fantasies confused me because they were full of women.

Women turned me on and it left me with a lot of questions I couldn’t answer or didn’t want to answer.

After a while, it all kind of clicked. I didn’t have to question my attraction to women. I could just take it at face value and accept that I’m bisexual.

I was no longer questioning myself and I went into my late teens really wanting to know what it would be like to have sex with a woman.

I had crushes on a few girls, but I never pursued any of them. I’m just not a chaser, and none of the women in my life flirted with me or tried to initiate anything.

With one exception.

I met Abby in high school. She was a year younger than me but we had art class together.

I introduced her to a friend of mine and they started dating, so I got to spend a lot more time with Abby.

We got along really well. She was fun and someone I could do irresponsible things with, like taking ecstasy at the bowling alley.

We’d also get physical with each other. We would get drunk or high and then make out. We kept everything above the waist and over the shirt, but it still felt really good. I made out with other girls at parties, too, but with Abby I didn’t feel like I was the only one who was really into it.

But I wouldn’t say I was attracted to her. We were friends who got frisky at times, and that’s basically how I saw her.

We were also both in committed, mostly monogamous relationships with our boyfriends, so we knew we were just having a bit of fun. We weren’t trying to get anything serious going.

And then I turned twenty.

My Birthday Surprise

My birthdays have always been really small affairs because I was born on New Year’s day. Most people are too busy to celebrate with me on the 31st and too hung over to share some cake the day after.

I met Mr. Austin just before I turned 18 and I’ve celebrated all of my birthdays with him. Occasionally, one or two people will join us, but we always skipped the big parties and kept things low key.

The night I turned twenty, Abby asked if she and her boyfriend could come celebrate with us.

We had cake and booze and spent the evening talking in bed because our apartment was too small for a couch.

I wish I could remember how we got from talking to what happened next, but I can’t.

Maybe we were just talking and it sort of happened.

Maybe we were flirting and inching closer to each other.

Maybe we tried to fill the silence by making out and we got more handsy than usual.

Maybe she just went for it. I don’t know. But at one point, she slipped her fingers down my pants.

With her lips against mine and her fingers rubbing my pussy through my underwear, all I could think was “Oh my God, I can’t believe we’re doing this!”

Then, the panic set in. Was I going to be good at this? Do I even know how to get a woman off? What if I don’t even like it?

But I didn’t want to stop it.

It got real when she pulled my pants off. She spread my thighs and started licking my pussy.

Mr. Austin reached down and spread my lips to help her tongue get to my clit. I stroked his cock and enjoyed the way Abby’s tongue felt.

Abby’s boyfriend just watched from the sidelines, enjoying his lesbian fantasies coming true.

She went down on me until I had an orgasm. Then, it was my turn to get her off.

I pulled her up and we made out again. I tugged at her pants but couldn’t get them off. Her skinny jeans were way too tight for me to budge. I tapped into my inner domme (she doesn’t exist, but I can fake it for a minute if I have to) and told her, “Take these off.”

She did as I asked and it was my turn to go down on her. This was the moment of truth — my first time licking pussy.

I should’ve been excited. In some ways, I was. But I was mostly terrified.

I moved my tongue around in a way that felt right, but I couldn’t stop worrying that I was doing a terrible job. And if I’m being honest with myself, I probably did, because I had no damn clue what I was doing and I was way too nervous to fake my way through it.

So, I just licked and kept licking.

I wanted to finger her, too, but I was really worried about hurting her. I worried my nails were too long or that I’d be too rough or that something — what? I have no idea — would go wrong. So, while I was slowly and gently pushing my fingers in and out of her, I kept saying things like “I’m worried I’m going to hurt you?” and “Are you okay?”

I should’ve known my way around a pussy better than this, but at this point in my life I didn’t masturbate with my fingers. Even touching my own pussy was completely foreign to me. All that shame I had internalized about self-pleasure left me completely unprepared for this occasion.

She either had an orgasm or faked one. I’m not sure which, but I feel like I touched and licked her too timidly for it to do much good. I was like a kitten licking an ice cube.

I was happy I got to go down on her, but I was relieved it was over.

I had so much anxiety about the whole thing. I kept telling myself I’d do better the next time. And maybe that’s true, but there hasn’t been a next time — not with Abby or with anyone else.

Wishing I Could Do It All Over

The rest of the night was a bit awkward. Abby and her boyfriend capped off the group sex by getting into a fight.

We never fooled around again. And that’s okay because I didn’t want to sleep with Abby again. I really liked her, but I wasn’t attracted to her. I don’t think she was attracted to me either. We fucked because we were both newbie bisexuals and our desire for experimentation made up for our lack of desire for each other.

I don’t regret sleeping with Abby, but I do worry that it affected our friendship. And the whole thing left me wanting a do-over. Not with her, but with another woman.

I wish my first time had been different.

I wish there had been heat and passion between us. I wish it was with someone I desired and who desired me back.

I wish there was so much affection, tenderness, and attraction that it didn’t matter if I was good or not because it would be about so much more than that.

I wish there had been more time to ease into it, more build-up, not just a surprise hand down my pants. Enough time to anticipate it and mentally prepare myself, at least.

Not having an audience would’ve helped, too.

Every New Year, I remember that night. I think back to everything I did wrong, how inexperienced I was, and I go through all the things I should’ve done differently. I like taking the opportunity to reflect on it and learn whatever lessons I can.

I hold that memory fondly because it was my first time with a woman. But I really hope it wasn’t my last.

Let’s keep in touch! Sign up for my weekly newsletter (I won’t send you anything without your enthusiastic consent!)

❤ If you liked this post, you might also love: