I Had A Threesome And It Was Awkward AF

But I’m so glad I went through with it anyway.

Shannon Ashley
Mar 14 · 10 min read
Photo by Larm Rmah on Unsplash

You can learn a lot about yourself and the world around you by making shitty choices. As much as everybody worries about fucking up… it can actually be pretty damn good for you.

Betting on the wrong pony, throwing caution to the wind--I don’t want to minimize the reality that some bad choices can, um, kill you.

But the ones that don’t can help you grow.

For someone who’s had a lot of sadness in her life, it might seem strange that I don’t have many regrets. I’d like to think that’s because I tend to learn something relevant from most of my "mistakes."

Honestly, a threesome isn’t an inherently bad choice. Yours could be, if it led to something like… murder. I once watched an episode of Forensic Files where that’s exactly what happened. To call that ménage à trois a bad idea is an understatement.

I had a threesome once, and it was definitely with the wrong people for the wrong reasons. But it also didn't lead to anything terrible or even too dramatic. It was honestly awkward AF, but I learned a lot from the experience.

I used to hate being single.

In the winter of 2014, I was a new mom grappling with singleness. My fiance ended our relationship early in my pregnancy and quickly wound up living with a new woman after kicking me out of the apartment we shared.

I was spectacularly broken back then and I didn’t know how to escape the toxic blurred lines that remained between me and my ex.

He broke my heart, but he also treated me like dirt. And I let him. Despite our breakup, I still loved him and he still fucked around with me because of that.

During the pregnancy, he went so far as to suggest that we become fuck buddies on the down low. He wanted me to agree to have threesomes (without telling his girlfriend, of course.) And he wanted me to insist upon delivering our daughter by cesarean, since he was worried my pussy wouldn't be tight after a vaginal birth.

I hated the fact that I didn't know how to turn off my feelings for a man who treated me like trash. I felt unable to maintain any boundaries with him, so I made a real effort to meet somebody new mainly because I wanted to get over my ex.

Through the magic of online dating, I met Ian. On paper, we were a good fit. He was a single dad who had his daughter every other week, he was intelligent and a little nerdy. The attraction was there.

It’s not often that I enjoy sexting someone new. It’s not often that I find myself attracted to anyone new. But Ian ticked a ton of boxes, and I wanted to get over my ex.

Of course, the problem with Ian was that he was unequivocally a jerk. I knew it every time he made plans and then canceled them with me. When I was on my way to meet him. And I knew he just wanted to use me for sex, despite saying he wanted an actual relationship. The worst part was that he wanted it to be easy and convenient for him--and he wasn't honest about that.

Ian didn’t care about the fact that I was a single mom and that every time he canceled on me last minute, it was a pretty big deal to find childcare all over again.

In those days, I had a hard time letting go of a relationship in any stage if I felt attracted to and invested in the person. I knew the “smart” thing was to quit indulging him, but I decided to stick it all out because I needed to prove to myself that I could get past my ex.

Even my fantasies are awkward.

Having sex with someone new felt like an important milestone after the hell I’d been through with my daughter’s dad. I was afraid that I couldn't even enjoy sex again.

Somewhere in our texting/sexting, it came out that I was breastfeeding, and Ian had a lot of curiosity about that. Personally, I don’t have any problem separating the non-sexual function of breasts from any sexual purpose in the bedroom, and I really don't understand the squeamishness some people have about breast play with a nursing mom.

When it came out that he not only wanted to know what it was like to be with a breastfeeding woman, but he also wanted to have a threesome, I went ahead and agreed.

He had a female friend with a generic name like Jenny, who thought my pictures were cute. I didn’t have any persuasion one way or another about her pictures, but I did want an environment to explore sex with a woman. Something about it being with a stranger seemed better and more low key.

To be honest, I have never been sexually attracted to any specific woman, but I have long been turned on by the idea of it. The only type of porn I watch is lesbian porn. And whenever I engage in solo sex, if there isn’t a particular man I like, you can bet I’m fantasizing about having sex with a woman. Not just that, but I imagine having a woman school me in bed.

Of course, I recognize that there's angst in the lesbian and even bisexual communities about hereto women who are bicurious. It's easy for the queer woman to feel used while the hetero one behaves selfishly. I've never wanted to do that to anyone, which gave me another reason to try a low-key threesome.

Merry Christmas to me?

I waited until Christmastime when my daughter’s dad was visiting to go ahead and make plans with Ian and Jenny. Amazingly, he never canceled those plans. My ex dropped me off at Ian’s apartment and agreed to care for our infant that night. At nearly 9 months old, our daughter went through a happy period where she slept all night without needing to nurse.

At Ian’s, he and I spent time with each other before his friend arrived. We watched Futurama, ate pizza, drank wine, and began making out. Pretty quickly into the makeout session, he asked me to suck his dick.

After a large but internal eye-roll, I complied, got him off, and we dry humped until his friend arrived. She was perfectly nice, though I felt no actual attraction--just curiosity about what would happen and I wondered whether or not she would want to go through with it all.

The three of us spent some time together on the couch. It was hard for me to not feel a little weird about being the newcomer. Or about Ian taking turns kissing us and moaning with his hands down both of our shirts. I mean, the dude was in heaven and it all felt pretty damn harem-y. Like the two girls were only there to please him.

Some uncertainty diminished when his friend suddenly shot up off the couch and said, “Okay, who wants to get into bed?” We all shuffled over to his bed and the next few minutes were a blur.

I don’t remember taking off our clothes, although I know I was scared. Because I have lipedema, I’m always hesitant to reveal my body to somebody new. I never know what they will think about my unusually large legs. But nobody said anything about my shape.

Definitely, the worst part about the whole thing was that I felt like an outsider. The two friends were obviously already routine fuck buddies and had lots of inside jokes. They chatted and made plans for future weeks and for the most part, I felt excluded, like I was a novelty item to them. I also wondered if Jenny was hoping to become more than fuck buddies with Ian, but I figured it wasn’t my business.

Awkward is an art for me.

I don’t want to describe the sex as terrible, or hint to it being among my worst experiences in the world. Honestly? It wasn’t great, but I think a lot of that was simply due to me being unable to relax.

There was definitely an awkwardness about what to do when Ian was fucking Jenny, and honestly, he was on the large size. Between his size and my nerves, I don’t think he was able to penetrate me. I also didn’t cum.

At the time, I was really embarrassed about that, but now that I’m older and more experienced, I realize it didn’t even matter. We were all there for the experience, and the foreplay was really the best part anyway.

There was one point where he went down on me, and it was all so rough and clumsy that all I could think was, “Oh God, make it stop.” But I was too embarrassed to say anything. I eventually just pushed him away so we could move onto something else.

I kissed a girl and I kinda liked it.

At least, I think I liked it. It was definitely weird, and I had a lot of guilt from my upbringing telling me it was wrong. It was different being on the other side and doing the things that have traditionally been done to me.

I fingered her until she got off, and I felt her nipples beneath my tongue. It was different, because it was never about passion or intimacy. It was more about mere mechanics and getting the damn experience. To be fair, it was probably the only time I could separate my emotions from a sex act.

When I think about the threesome now, it genuinely doesn't bother me that I wasn't attracted to Jenny or that there were no emotions between us. It was like scratching a deep itch we both had, and I get turned on just thinking about it. If it happened these days, I have to admit I'd probably be much more into it and have fewer inhibitions.

But the best part for me by far was the breast play. User DominantSoul64 from FetLife once wrote about how getting breast play right was, in fact, getting the “keys to the kingdom.” I have to agree.

If I’m a little bit on the fence about having penetrative sex because I’m simply tired or not in the right headspace, having my breasts get plenty of attention and foreplay is one way to get me into the mood.

So how can I say it? It was fun having a man and a woman drink my breast milk simultaneously. They were both surprised that it tasted sweet like vanilla milk. And I was happy to feel sexual and desirable after so much shit with my ex.

Here’s where it devolved into a sitcom.

I’m not the greatest sleeper and I typically have a hard time sleeping in new places. After the threesome grew weary, I couldn’t seem to fall asleep while the other two snored, so I snuck out at 4 or 5am.

My ex picked me up and a few hours later we were at a used bookstore because I had decided to sell my enormous manga collection since it was Christmastime and I didn’t have a job. I needed the money.

To my horror, while we waited for the employees to price my books, I saw Ian browsing the history titles. That’s him, I hissed to my ex.

I was suddenly very sheepish about sneaking out of his apartment and unsure if I should say hello. I didn’t know if he’d seen me.

The whole thing was cringe-worthy, but I opted to say hi and hoped I didn't look like a stalker--with my baby, baby daddy, and manga all in tow just hours after what was basically a one night stand.

Ian was surprised I had left and said he wished I had stayed. But I didn't regret leaving that awkward bed when I couldn't sleep. We said goodbye and never saw each other again.

Ian did occasionally text me whenever he felt horny and wanted a hookup, but I never obliged. It turned out that even though I didn't know exactly what I wanted or needed back then, having that threesome did what I needed it to do.

It showed me that I could still be a sexual being, but more than that, it confirmed that I wanted better. Like a partner who respected my limited time as a single mom.

This story is... hard.

Some stories are so taboo, it’s hard to even know where to begin. This has been one of those tales, and I’ve grappled with the question of how to approach the story for far too long.

Threesomes are taboo for multiple reasons. For one thing, our culture is so strongly positioned for monogamy. But we know that plenty of people still get off on the idea of a threesome.

Yet the idea of regular people (not celebrities, and not perfectly beautiful) having a threesome is too tough an idea for many folks to swallow.

Plus, the former evangelical in me is still ashamed for certain people to find out. The realist in me knows that plenty of people will be grossed out. And the sex-positive champion in me questions why I ought to feel embarrassed at all.

In my heart, I think the real cause of my embarrassment over having a threesome isn’t solely hinged upon the spiritual shame of my background, but the reality that I had a threesome for the "wrong reasons."

I had a threesome because I was lonely and miserable in my role as a new mom with no partner. I had a threesome in an effort to help me try to get over my ex. And I had a threesome with a dude who really didn't respect me that way I would like.

For the record, I am not against casual sex. I am not judging or condemning anybody who engages in casual sex. That said, casual sex is usually a poor choice for me as a demisexual who seeks an emotional connection before a physical one.

But remember what I said about bad choices? Sometimes they're pretty damn good for you, and this one was. It helped me feel more comfortable with my sexuality, and these days, I no longer do things because I feel pressured by men or by shame.

These days, I know how to talk about what I want because of such "bad choices."

And that's a pretty big fucking win--even coming from a fuck-up.


Awkwardly Honest

A home for some of my most cringe-worthy tales that have been well-received on Medium.

Shannon Ashley

Written by

Single mama, fulltime writer, exvangelical. It's not about being flawless, it's about being honest. Top Writer. http://www.patreon.com/shannonashley

Awkwardly Honest

A home for some of my most cringe-worthy tales that have been well-received on Medium.

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