by Jenny

Gender: Female
Age: 22
Race/ethnicity: Caucasian/Part Native American
Location: Northern Midwest, US
Highest education received: Some college (not currently in college)
Occupation: Night/Weekend Manager, Food Service/Delivery Restaurant
Relationship status: In a heterosexual relationship for almost 4 years
Religious affiliation: Working towards Buddhism
How religious are you? Not at all
Sexual orientation: Bisexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Pansexual & Polyamorous, no boundaries
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? 0

Strange Tryst For Three Dear Friends

How long ago did this hookup happen? 2ish-3 years ago.

How would you best classify this hookup? Three friends with prior sexual relations with one another; committed to a threesome.

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? One was a guy and one was a girl. The girl I’ve known since we were just out of our pre-teens. I’ve pretty much been in love with her from first sight, and back in our exploratory younger years we messed around a few times, with me as the instigator, kissing and touching her usually. She was bi-curious but most of the girls our age acted fairly bisexual, at least until the last second when they’d admit to not REALLY liking girls. I knew from at least age 10 I was sexually attracted to girls just as much as guys, in fact just feeling sexual/emotional attraction to anyone striking my fancy, regardless of traits. This girl broke my heart when we were kids because I thought I’d get a chance at dating her, and eventually it came out that she was pretty much hetero. We still stayed really close friends, like sisters (in a weird and kind of hot incestuous-intimacy-friendship way) and at this point in time we were still extremely close. She’s as short as me (just over 5 feet tall) and while we were both relatively the same weight at the time, she has a very petite bone structure with an hourglass figure and a HUGE chest. I’m sort of awkwardly hourglass-shaped, with broad shoulders, wide hips, small chest and a huge ass. She pretty much looks like a miniature porn star, whereas I’m fairly awkward and tend to be more tomboy.

The guy was a friend of mine first; we’d been long-distance friends for about 4-5 years, and we had a casual, affectionate & sexual sort of relationship throughout our interaction. I had had a massive crush on him early into meeting him, but he’d been dating another girl for a long time and we were both comfortable with our situation. Besides, I had and still have a boyfriend, whom I love very very dearly, but I still feel it’s natural for people to be attracted and have sexual or at least intimate relations with multiple people, whereas my boyfriend is fully monogamy-oriented and still can’t grasp where I’m coming from with my perspective. So it’s sort of a secret thing I have to hide from him and try to restrain. Anyway, the guy friend is well over six feet, very lean and slender, very energetic.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The guy friend was visiting for the first time. He and the girl had started dating about a year beforehand, even while he and I were still casually fooling around with each other for our personal self-pleasure. The girl came into this relationship knowing the affectionate, playful, and highly arousing friendship he and I shared, but I saw her fall head-over-heels and I cared about her too, so I sort of just pulled away from the intimacy with him and stayed good friends. At this time, and for the first time in years, the girl was actually actively getting intimate with me, because she knew the two of us together turned HIM on, and she’s pretty naturally porn-tastic I don’t know, like a natural sexual goddess or something. I kept my feelings for her this adoring, sisterly, mildly incestuous but mostly girlish & silly type of interaction, and everything seemed mostly pacified emotionally.

We were in a hotel room. We’d been in a few different ones over a couple of nights, and we were partying hard – booze, drugs, swimming pools, mild crime spree, everything. The night we decided to hook up I was pretty dissociated on some chemicals and we all three sort of agreed (while fucked up) that this “thing,” the threesome we’d been joking about without any seriousness for like a year now, should actually happen. We all three agreed but I was fairly unemotional and practical about it, being pretty messed up; I thought nothing about consequences or anything, just that it would be an experience and we could get it out of the way.

Oh, also should mention, the girl had been getting pretty jealous and possessive of the guy in the past few weeks before this. I understand how couples get with their significant other and I have dealt with being the target of animosity just for being polyamorous, but it seemed to come out of nowhere and I was offended that she would pull dominance over me just because they’d been dating; I’d known HIM longer than she had, I’d known HER longer than he’d known her, I’d been intimate with both of them before they’d ever even met each other…well it was just odd. So the last thing we agreed (without bringing any of this up but we were all aware of the jealousy issue) was that during the threesome, the girl and I could touch each other, and they could touch each other, but he and I were by no means allowed to touch each other (which also somehow absolved me of any feeling like I was cheating?).

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? It started out interesting enough. We were all pretty messed up but I think I was moreso than either of them, they were just really excited to be having sex finally (oh yeah, it was their first time consummating their relationship, forgot about that). We were all naked except I had a pair of boyshorts on, because I was more interested in being the dominant if I was going to be just playing with a girl. He and I were fondling her and getting her aroused, and most of the night I had a weird thought that it was like we were carrying out rites or duties to some sort of sex deity (could’ve been the drugs though).

I like giving oral, on males or females, but by the time I decided to go down on her I just felt pretty emotionally distanced from the situation. I remember thinking, “Well, time to do this. Just go for it. Right now,” as I was going down on her. I kept having to motivate myself to stop hesitating and just jump into the fray. Once they got into it, they were more interested in each other and I felt clearly third-wheel-esque, but it was all too strange and unfamiliar to all three of us so we didn’t feel we could openly discuss the awkwardness we were all apparently feeling. 

A few times I got off the bed and went to the other side of the room to insufflate more chemicals and just leave them to their coupling, trying to be considerate and selfless without saying anything or drawing attention away from them focusing on one another. They kept changing into all sorts of positions and went at it for a while, and after dipping in to nibble and fondle the girl a little and then dipping back out to give them their moment, I kind of just crawled to the back of the bed and played music on the laptop, being my basic voyeur self and watching politely. One thing that was really confirmed is, yes, I am a die-hard natural voyeur.

Afterwards the girl decided the threesome was a super awkward bad idea, and he was sort of apologetic and consolatory in reaction; I still don’t think the threesome was a bad idea at all and it really didn’t have a lasting impression upon me, like it occurred in this window of time but once we were done it was over for good. My emotions DURING the sex were just the opposite of who I am and how I behave, especially intimately. I’m definitely a hardcore voyeur, but I’m also really dominant and aggressive with consenting girls, and I figured the guy and I would sort of be “bros” about it. I don’t know, maybe it was all very weird.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We all knew in advance that all of us were clean from any STIs, and the girl had an IUD so she wasn’t concerned about pregnancy. Being close good friends made the STD/STI concern a non-issue for us because we knew each other well.

What were your REASONS for having this hookup? I care a lot about both of them. They’re like siblings and beloved friends and hard romantic crushes all rolled up into single packages for me. I also love sex between close friends. Lovers should be the best of friends, in my mind, and friends make pretty great lovers usually.

I think all three of us have the same sort of basic affectionate casualty about sex with friends, that’s why it worked out so well.

Were alcohol or drugs involved? If so, how much? I’d had a few beers before I joined up with them. We were also doing a lot of touchy-feely (empathogenic) and dissociative chemicals, for the fun of it all. I think that’s the only way I came out of it with such apathy about it all.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We were all friends right afterwards, and for a while after. The girl and I had a serious falling out because she started cheating on him when he went back home, and it sucked to be between friends like that. They had a really terrible and vindictive breakup a few months later anyway and she went off to her own things. Her and I have had years-long falling-outs before but we’re still not really friends right now (based on her current life choices and insincere behaviors). He and I are just as close as we’ve always been, and still pretty dear to each other.

To whom did you talk about the hookup? How did they react? I told our other friends who’re friends with all three of us (long-distance non-irl friends), since we’re all sort of casually intimate poly-friends of sorts, and they were thrilled and thought it was awesome. I didn’t really tell anyone else in my irl but I’ve recently found out that the girl basically told two of her exes and her current boyfriend about what happened, as well as others in our circle of friends. I have no idea who else knows about it and it’s distressing, especially because of my boyfriend.

Was this a consensual and/or wanted experience for you? For your partner? Yeah, it was consensual, intentional, desired. Once it actually was happening I wished I wasn’t there at all, felt way exposed and lonelier than if I’d just been alone with myself.

Do you regret this hookup? If so, why? Not at all. The guy and I kept our friendship intact as it stood at the time and it’s still solid presently. I liked interacting with the girl but it was also a lesson for me, showing me exactly what kind of person(s) and in what situations I definitely don’t want to expose myself to, emotionally and physically. The vulnerability felt terrible initially but only got worse when I knew I’d misjudged the situation and it wouldn’t be a fun and inclusive experience for me.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing was testing the bounds / boundlessness of the intimacy between very dear friends, and not only did we all manage to share so much more than could have been predicted, we also came out of it pretty much unscathed. Also, got to see some realities/truths about myself and both of them in the middle of a one-in-a-million-possibilities set of circumstances.

The worst part of it all was the awkwardness that only got worse for me, the more comfortable they got with one another. It’s a bare and raw feeling of loneliness that you only really feel when totally exposed in front of others; like I said, I’d have felt so much less lonely actually being alone.

I think the one thing that was really confirmed is, yes, I am a die-hard natural voyeur. I used to think I just sort of people-watch but otherwise I watch stuff while alone; but being able to just commit to voyeurism in front of others, that was somehow comforting. Also, while I’m dominant and aggressive with females, I’m masochistic and fully submissive with males, at least generally. I think I got more awkward when, firstly, the girl was definitely in charge of the proceedings, and secondly, the guy and I couldn’t interact at all yet he’s definitely dominant. The dynamics got way too uncertain and bewildering.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience?: A little negative

Anything else you want to add about this hookup or anything else? Both the guy and I have admitted that we wish we could’ve just hooked up with each other. Oh, well!

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