Boarding School Drop Out



What’s your gender? Woman
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Germany
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Psychologist
What’s your current relationship status? Single
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Queer
How many sexual partners have you had in your life (including oral sex)? approx. 41
How many hookup stories have you here posted before? 1

Boarding School Drop Out

How long ago did this hookup happen? 2011

What was your relationship status at the time? In a relationship (open)

How would you best classify this hookup? Short fling

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 18, blonde, baggy-jeans and snapback type of guy with an eye-catching lip piercing
We only knew each other superficially before hooking up.

We met on a train, when he sat down in front of me and had an immediate bad boy vibe to him. I was quite bored and a bit frustrated that day with my life, a little reluctant to spend my weekend travelling to several conventions as a speaker.
It was a long train ride and just his body language, flashy look and his lip piercing sparked my immediate interest. I had been curious what is would be like to make out with someone who has a lip piercing and this wasn’t the first time I found this instantly exiting. He quite obviously noticed I was observing him. An opportunity to ask him a genuine question popped up and his answer just made him more interesting (he had just dropped out of boarding school and obviously came from a family with money and was on his way home). We had a somewhat superficial conversation and it was pretty obvious we found each other intriguing, but kind of from an odd distance, like an exotic creature we didn’t really know how to approach and whether we should. When we approached his stop he offered to exchange numbers.

Before the hookup I was somewhat sexually curious about him and thought he was nice but that we had nothing in common. I was also hesitant because of the age difference and him perhaps being a fucked up kid I shouldn’t get involved with.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Since I lived in a different town, there was some planning involved. We had texted once in a while and he randomly called me and we talked quite a bit. I don’t remember how it came up, that he should come visit me, but he had spare time on his hand and a railpass he could still use til the end of school term. So he traveled quite a bit with it, just visiting people. So we decided he could visit me. We never really flirted on the phone and never specified this would be a date. But considering he was a boy who asked for my number in a situation with some tension between the opposite sexes, I guess it was clearly a possibility we would hook up. I was unclear with myself whether I wanted this but liked having him visit me and to have the possibility.

When he visited me, he slept on a guest bed next to my bed. I had been feeling a lot of tension that obviously something was kind of “supposed” to happen, since a lot of his visit had been kinda date-like and because of implication of us being in touch due to a sexual tension in the first place. This is pretty stupid, because I didn’t really feel attracted to him much during the date/hanging out.

We were lying awake, the way it is with sleepovers where you are in the same room and we kept talking. He was telling me this (seemingly?) random story about some vacation where he was massaging girls and how he really likes to massage and going on about it. Even though it was a obvious move to get physical with me, I kind of went along with it when he offered to massage me to show me his “skill.”
So he climbed into my bed and massaged me at first in a more harmless way for quite a bit. And then said he wanted to show me his belly massage technique, and things got more physically intimate. He then from there somehow transitioned slowly to massaging me intimately. At that point I figured I had let it go this far, I might as well just fuck him, even though I wasn’t really feeling it. The massage was nice, but not really good. It was somewhat erotic and nice, but also awkward and I wasn’t really aroused much. So mostly he instigated it.

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? His piercing wasn’t as hot as I had imagined. Actually more uncomfortable/distracting. He also was a disappointing kisser. Not bad, but not good. The sex itself was one the the most boring and disappointing sexual experiences I ever had. I can’t remember much details anymore, but I didn’t really like his exact missionary position moves and me taking control of movements didn’t seem to work for him.
At the time I was into BDSM with my long distance relationship partner, so I thought I was missing that kind of spice. I asked him whether I could tie him up. He kind of shrugged and said yeah sure. So I improvised, getting up to pull a scarf from my closet to tie him up. But he really just laid down on my bed spread-eagled like a dead fish. After some halfhearted attempts to dominate him with bondage, I let it be and returned to vanilla sex just letting him do his thing. Cuddling wasn’t quite as awkward after sex. but the morning half-wake / half-asleep/ kinda making out felt awkward.

How sexually satisfying was this hookup? Not at all

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? We kind of had small talk and kind of cuddled / made out or just laid next to each other in the morning. Since the chemistry was even worse in the morning and I really didn’t want to continue the sexual activity, I offered him to make pancakes. After he had breakfast, I took the bus with him to the train station. When his train came I gave him a kinda sweet, kinda awkward goodbye kiss. I think we both were kind of glad this hookup was over and it was pretty clear we would likely not meet again soon.
We didn’t stay in touch much. He wrote me briefly on Facebook a few times and for a while I’d check his Facebook once in a while. I think he is in a happy relationship now and I hope he is doing well. In hindsight I think he was just a kid figuring things out and maybe it was a mistake to let him be in the assertive role and that probably the whole thing was similarly weird and dissatisfying for him.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, To feel more desirable, To feel more confident, I was feeling lonely, Didn’t want to disappoint my partner, Boredom, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? A little bit

Did you consent to this hookup at the time? I first kind of let it happen and then consented by having a talk about using a condom

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

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 have told a few people but the story was kind of fucked up and friends were mostly shocked. I also felt awkward about me telling them about bad sex. I feel most of my friends didn’t really get my whole open relationship thing and therefore felt awkward about me sleeping with another guy when I had a partner.

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

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

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? Somewhat

Why do you regret this hookup? Now in hindsight I don’t regret it much, because I feel I learned from it and it doesn’t seem like a big deal now.
But at the time it was a sexual experience that felt uncomfortable, weird and unsatisfying and I don’t want to experience something like that again.

What was the BEST thing about this hookup? Using my freedom as a woman in an open relationship and making new dating experiences

What was the WORST thing about this hookup? the sex feeling mostly awkward and uncomfortable

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. Before this hookup I had the golden rule never to sleep with a man the first night. I definitely learned my lesson since I was only really going along with it because I felt like I had to.

Also this made me realize a lot about how BDSM works for me from an emotional and psychological level and taught me things I don’t really like (not feeling assertive in a hook-up, going along passively, lack of passion).

It still felt empowering to have had a side fling I had kind of chosen for myself without having to tell my boyfriend. But it also made me feel I should trust my instincts in a situation more and take more control and more actively phase out of situations that aren’t working for me.

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

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

Anything else you want to add about this hookup? nope

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 wish I had more casual sex but unfortunately it is usually not really casual sex. Most of my “casual” sex experiences were not casual from the level of emotional and/or cognitive intimacy. Also I catch feelings a lot, especially with men, causing perhaps more harm then pleasure overall.

Casual sex should be destigmatized, if it is conducted ethically, but also viewed more realistically. People have different needs and I dont think the standard way we portray casual sex works for people.

What do you think about the Casual Sex Project? I love the project!
That said … I don’t think the categories for the question on consent present a realistic scale.
I don’t agree with the idea of only “enthusiastic consent” being giving consent. I’ve tried to find definitions of enthusiastic consent but I think this is something that rarely happens and that the societal norm for consent is still non-verbal or some kind of verbal consent that I wouldn’t call “enthusiastic”.
Also many stories I find a little incredible and some people violate the terms by using names of their partners.
For me it has been eye-opening to see how differently men and women tend to describe their hook-ups. Obviously men and women do feel very differently about casual sex and have other ways of approaching it. Would like to see some text analysis research on this.

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