My First Time with a Woman Was Super Awkward

It didn’t go like I expected, but I would do it again

I’ve been attracted to women longer than I’ve been attracted to men.

The first time I really had those kinds of feelings for someone, it was a girl named Hailey.

I spent the summer with her, and we got closer and closer. But then I fucked it up royally and nothing ever happened between us.

Then, I got a boyfriend, had sex, and it was a string of boys from that point on.

I still found girls really hot, but I never got close enough to any of them to form any kind of romantic attraction.

Then I met my future husband. We got real serious, real fast and I knew I’d be with this guy for the rest of my life.

Realizing that I had met “the one” was amazing, but I was also a bit sad that it closed me off to experiencing sex or a romantic connection with a woman.

That changed, though, when I got some surprise group sex on my 20th birthday.

Friends with (Slight) Benefits

I met Abby around the same time I met Mr. Austin.

We got along really well. She was cute. She was funny. She had the same sexual energy as me, so I was comfortable around her.

Abby was also in the same position as me: bisexual but with zero sexual experience with women.

We didn’t have romantic feelings for each other, but we became friends with (slight) benefits. We often made out and got physically affectionate when we were drunk or took ecstasy together.

We’d get a little physical at parties, in the back of her boyfriend’s car, and once when we found ourselves alone in a bedroom. But it never went further than that.

We often joked about fucking each other, pulling our boyfriends in for some group sex, or orchestrating some kind of orgy with our friends.

I joke about that stuff with everyone. My mind’s constantly in the gutter — it’s just how I roll. I’m pretty open minded and willing to experiment, but I’m rarely serious when I make those comments.

Turns out Abby was.

My Big Birthday Surprise

I was born on New Year’s Day, and it’s hard getting people to turn up and celebrate your birthday when it falls on a major party day.

My twentieth birthday was gearing up to be a very low-key affair. I was going to spend it alone with Mr. Austin until Abby asked if her and her boyfriend Mark could spend the evening with us.

We got drunk, ate cake, and then hung out in bed.

The details get fuzzy at this point. I don’t quite remember how it happened, but at some point, Abby had her hand down my pants. Soon after, she pulled them off me and started going down on me.

This was one birthday gift I was not expecting.

I felt nervous but also excited. I was going to fuck a woman for the first time.

And, as I soon found out, it would be awkward as hell.

For one thing, her pants were hella tight. It made it hard to reach into her underwear to pleasure her. And when I tried to take them off, I just struggled with them until I had to ask her to take them off.

And once I was between her legs, I realized I wasn’t exactly sure how to get her off. I mean, I knew the basics and I knew what I liked, but I had no idea what she was into or what worked for her.

Having an audience also made me shy. Instead of being enthusiastic, I was timid. I remember fingering her while going down on her but being very careful — probably too careful — because there wasn’t really any communication between us.

If we had been alone, we would have been two people exploring each other’s bodies. Instead, we were two inexperienced people trying to act like pornstars for the sake of the guys in the room.

There was also a total lack of communication. She just started getting me off without much advance notice, and now we were four people who hadn’t talked about our comfort or boundaries.

Was Abby going to try to do stuff with Mr. Austin? I didn’t want her to, but would he go along with it not knowing that?

Was Mark going to touch me? Did they expect me to touch him? I’m not sure how I felt about that.

Those questions just hung in the air and I had to worry that someone would do something I wasn’t comfortable with — or that I’d do something to make someone else uncomfortable.

That made things weird, but it wasn’t that bad. It’s the kind of rookie mistake you might make during your first spontaneous partner swap. We would’ve figured it out.

It’s what came next that made everything super uncomfortable.

Abby and Mark had been together for a couple of years at this point, but you couldn’t really say they got along great. They bickered a lot. One of them always ended up saying something insensitive to the other.

You would think they could set that shit aside for the duration of a foursome, but alas that wasn’t the case.

While I was on my elbows and knees going down on Abby, Mr. Austin stood behind me and gave me some good old fashioned (but too distracting) doggystyle.

Mark, on the other hand, was dealing with some performance issues, so he mostly laid back and watched. He had a long-standing fantasy of being with two women at once, but having an extra M in his FFM groupsex made him too nervous to rise to the occasion.

That’s perfectly fine, of course. He just touched himself while watching the clumsy sapphic action happening inches away from him.

But that wasn’t good enough for Abby.

When Mark couldn’t get himself hard, she started complaining.

“Emma got fucked. I want to get fucked, too.”

She blew him until he got stiff and then straddled. After riding him for about a minute, she let out a loud upset sigh and climbed off his softened cock.

She pouted. He looked embarrassed.

We tried to make small talk but they were cold to each other (and what the hell do you talk about after having group sex when you’re purposely trying not to mention the group sex?)

After several extremely uncomfortable minutes, they came up with an excuse to leave and called a taxi. We all got dressed and stood outside, shivering in the winter cold, wishing that the cab would just get here already.

I Would Do It Again, but I’d Do It Differently

We were still good friends after that experience, but the awkwardness still hung in the air. Needless to say, we never got physical again.

And not just with her — I’ve never had sex with a woman since.

It’s not because I don’t want to. Far from it. I just haven’t met the right person yet. And who knows if I ever will.

I spent years feeling embarrassed by how that night went. I thought about how awkward the whole thing was and about how I didn’t do a great job at getting her off. I worried that I was a terrible bisexual.

Over the years, I realized I needed to give myself a break. It was my first time. I was a virgin when it came to women. And it unfolded with not one but two guys watching us, which made me extremely nervous and self-conscious.

Now, when I think back to that night, I try not to cringe at how awkward it was and instead take stock of the things I learned from it.

I learned that sometimes fucking your friends makes things weird.

I learned that you can’t have great group sex without clear communication, expectations, and boundaries.

I learned that I don’t just like having a woman’s face between my thighs — I also loved having my mouth on her pussy.

And I learned that the next time I sleep with a woman, maybe I should do it when her boyfriend isn’t around.

If you liked this article, you should totally check out the Hot Pussy Eating Positions (Doing It Standing and Eating It From the Back) episode of my dirty and intimate sex podcast, Pillow Talk With Emma Austin!

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