My Big Fat Gypsy Hookup

by Esmeralda

What’s your gender? Woman
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Alternative Heallh Care
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? No
How many sexual partners have you had in your life (including oral sex)? 11
How many hookup stories have you here posted before? 0

My Big Fat Gypsy Hookup

How long ago did this hookup happen? 10 years

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than 6 months

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? He was a friend of a friend. We would run into each other at parties thrown by this mutual friend. He was my “type” at the time – which was bearded, bigger and slightly frumpy. He was a bit of an odd duck, but he was funny and had a really intense way of speaking with you. He had nice lips and played music. He was also really fun to mess with at parties. This particular party was a Halloween party. I was dressed like a gypsy and I don’t remember his costume. We were both 21 or 22 at the time.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I don’t remember being particularly attracted to him, or having any intention on hooking up. But a friend of mine and I used to just heckle people at parties to see what they would do and he was our target often. For some reason there were a lot of Oreos at this party and we were stashing Oreos in people’s pockets on the sly. People wouldn’t be paying attention and then all of a sudden they’d have like 10 Oreos in their pocket. Obviously there was drinking at this party. So this guy had been a victim of the Oreos a couple of times and we were talking, I don’t remember about what. But there was some flirting going on and some physical contact, like my hands in his pockets. It was getting late and some people at the house party were starting to go to bed and pair off. At one point he grabbed me and dragged me into a closet and kissed me. It was a little unexpected and slightly weird but I kissed him back.

Now meanwhile, an ex that I had dated for about 3 years who had proposed to me about 7 or 8 months before was at this party. We had broken up after I had turned his proposal down, but we were also doing this emotionally messy occasional hookup thing. I considered myself single, but I knew the ex was still hoping that something more would happen between us again and that we would eventually get back together.

So when Oreo boy dragged me into the closet I was super nervous about my ex finding out that I was making out with someone at this party. He was a big dude and was no stranger to fist fights and I didn’t want there to be anything like that happening on my account. At the same time though I was enjoying the possibility of hooking up with this other guy.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We made out on the floor for a while, but I was afraid of people seeing us and someone reporting to the ex what was happening so I said we should go to the laundry room. This was a house of college guys so the laundry room was super gross with dirty clothes and a cat litter box in it. We made out with me sitting on top of the washing machine and him between my legs. We tried to have sex like this but our parts were not lining up so I rode him on the floor. I remember there being cat litter on the floor and the whole time I was making all kinds of jingly noises because of my bracelets and bells from my gypsy outfit. Which freaked me out because once again this was supposed to be in secret so the ex didn’t murder anyone.
He was a good kisser, like I said he had nice lips. He went down on me for awhile but I had trouble enjoying it because I was so nervous. We were both pretty drunk and clumsy. I don’t think either of us came.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? No, not even close

Did your partner have an orgasm? I don’t know

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? After the hookup he tried to snuggle with me on one of the couches. He fell asleep really quickly. But the couch was narrow and at this point I was a paranoid mess that my ex was going to see us together so I left the Oreo guy on the couch by himself. I slept on the floor in a different room. I did not have any expectation for a future with this person. I had never had a one night stand that I had the possibility of running into at future social gatherings. I either had relationships or made sure to sleep with randos that there was very little chance that I would ever cross paths with them again. I was worried that it would be awkward at future gatherings of our mutual friends. That was 10 years ago…now I still run into this person at parties of our mutual friend. I’ve hung out with him and his fiancé and we recently got into a deep (drunk) discussion about how much he loves his future wife, what he pictured their future to be together and why he is so good at his job working in collections. He is still an odd duck, still frumpy, still has very intent conversations that are a mix of serious and strangely funny.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Intoxication, Just happened, I don’t know why, just went along with it

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I think at some point I joked about it with the mutual friend. It was pretty ridiculous that I fucked his friend in the nasty cat litter covered laundry room in a gypsy costume.
I have no idea though if the ex ever found out about it. I hope for his sake that he didn’t because it was a pretty big asshole move on my part.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? Mostly because I really didn’t want to hurt my ex if he found out about it. I have felt bad about that part of it ever since. The ex was a genuinely good person, we broke up just because we were going different directions in our lives. He didn’t deserve to be hurt by my any more that he already had.

What was the BEST thing about this hookup? It’s kind of a funny story.

What was the WORST thing about this hookup? The guilt that I felt about the possibility of my ex finding out about it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I think that the way that I went about this hookup was pretty selfish. I have no problem with casual sex as long as no one gets hurt. It wasn’t really necessary for me to go along with this hookup and risk the possibility of hurting my ex. Even though we weren’t still together I think the decent human thing to do would be avoid hooking up with a mutual friend at a party where someone who proposed to you is in attendance. I have tried to be better in relationships since and try to be more conscientious of others feelings.
That being said, Halloween is a pretty fun time to experiment.

All things considered, how POSITIVE was this experience? Somewhat positive

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? Not that I can think of.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I think that it’s unrealistic to expect people to solely have sex in monogamous relationships. I think as long as it’s a positive experience for both parties, why not. I do think that that a bias still exists that it’s less acceptable for women to engage in casual sex without negative connotations, but perhaps with things like this that will slowly change.

What do you think about the Casual Sex Project? It’s fun to read and share. I’ve been thinking about telling some stories live and this is a good way to think about how I would share this story.

You have a hookup story to share? Submit it here!