Two Night Fling



What’s your gender? Woman
How old are you? 23
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Washington DC
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Actor
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 0

Two Night Fling

How long ago did this hookup happen? 3 months

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a month

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? We met on a dating app. We went out to a bar for the first date and talked for a long while. I felt we had a real connection, and I felt comfortable bantering with him. He had a unique, but attractive smile. Pretty soon, the conversation turned to our dating experiences. He said some stuff that raised some red flags with me, but I continued on with the date because I was so excited by our earlier connection. He walked me back to my Metro stop and asked to kiss me before we crossed the street. I hesitated because I was taken aback by his timing. He muttered “‘never mind” and started to cross, which is when I said “wait, come back!” and kissed him. We continued on to the Metro, and he asked me if I was drunk. I said no, even though I was a little tipsy. He asked if I wanted to come back with him to his place. I paused for a moment, then said yes. He said “yeah I know what you’re thinking. You’re thinking you’re gonna sleep with this guy….” (his assuming he knew what I was thinking was a common theme on this date). He kissed me again, and we talked amicably for a few minutes. I slowly realized though, that I wasn’t ready to have sex with him and told him so. He was very demonstrative in saying that it was no big deal, and totally my choice, and that I didn’t have to feel bad. We were on the same train, and boarded and sat together. He wasn’t much more interested in talking, and was weird about me trying to continue with the get to know each other part of the date. He said something like “no we’re past that” (???). We went our separate ways and texted a little bit over the next few weeks.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was working late in the city, and exhausted and stressed from a few other things going on in my life. He hit me up and asked me if I wanted to hang out, but also offered to meet in public. Genuinely, I would have met him in public, except that I didn’t want to pay for parking in the city so I agreed to meet at his place. I wasn’t expecting something to happen, but I knew it might. When I got there, we went up to his room and chatted for a bit. I asked for some water since I was thirsty after work, and he handed me the water that was already on his bed side table. That didn’t feel so good. But, when he started kissing me I was into it and thought “why not?”.

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 had oral and vaginal sex. I hadn’t had penetrative sex before, and I told him that and asked him to go slow though he seemed a little bit impatient about it. A few minutes into him being inside of me, he asked if he could call me names. I asked him what he meant, and he started calling me his “little bitch”. I let him TRY it, but realized quickly I was not into it and asked him to stop. He tried at some points to finger and perform oral sex on me, but I’m very sensitive and sometimes have a difficult time enjoying that. When I asked him to be gentle, it frustrated him because he didn’t seem to know how to be more gentle than he was. I went down on him, however, which I enjoy doing, but it quickly became uncomfortable when he thrust into my mouth without asking. I asked him to stop, then let him try again when I was better prepared. All in all the sex hurt a little, because I was new to it and I couldn’t go for long. He jacked himself off by looking at me and moaning my name. Afterward, we were fairly quiet. He said “at least your first time was good, my first time I couldn’t get it up”. I stayed the night but couldn’t fall asleep because I was feeling so anxious. I think he was too. Eventually he said “if you want to leave I won’t be offended”, and I did since I had work in the morning anyway. He kissed me goodbye and I drove him.

The second night, happened a week later. We had been texting and flirting and he invited me over. We talked for a little while and drank some wine that I had brought over, and started kissing. He asked to call me names again, to which I said no. I don’t remember much of the details except that we went into penetrative sex pretty quickly. I was at the beginning of my period, and his penis acted like a suction that made me bleed more heavily so I had to hurry to the bathroom to clean up. When I came back, he said “well I guess we’re done. Sorry, I don’t want to ruin my sheets”. We kept fooling around and he asked me to dominate him. I didn’t exactly have the inclination for it, so I asked him what he wanted. He said, “whatever your instincts tell you” while avoiding eye contact. So, we engaged in some anal play while I talked dirty to him and he came all over his sheets. Afterward, when he had stripped the bed of its linen, he acted a little strangely. He immediately launched into an explanation of why men get tired after sex and why women want to keep going (in retrospect he seemed to mean “I’m tired, get out”). He then talked about what he and his ex girlfriend did after sex, and apologized for it. We had some conversation getting to know each other, and he seemed to begrudgingly engage in it. Then finally, he said that he had work early and I took the hint to leave. As I got up he said “oh you’re mad aren’t you?”. Confused, I said “no I’m not mad, I’m just….getting up to leave?”. He walked me out and kissed me good bye, saying, “we should do this again”. We texted for a little while after that, but when I attempted to make plans he eventually stopped responding. I did see that he had updated his dating profile.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? No, not even close

Did your partner have an orgasm? Yes, one

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? I felt pretty icky. I thought sex was a means of getting to know this person, even if it happened early on, but I felt like a human sex toy in his bed. Exploring the sensations of sex was thrilling, and I found pleasure in pleasing someone else. But, in retrospect, had I been more experienced I would have realized that he was likely just after a hook up. I know I don’t have anything to feel guilty about, because I just said yes to an opportunity that was offered, but I regret the experience. I didn’t necessarily want to date him, but I was frustrated because he kept saying “I’ll text you” and “we should do this or that!” when clearly he was hoping that I would just disappear, or be occasionally available for sex.

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, Hoping or expecting it would lead to something more, Thought it was an important experience to have, Just happened, I don’t know why, just went along with it

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? Somewhat

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? My friends! They were surprised at this behavior during sex, but had more foresight than me in realizing what this guy was probably after.

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

Did you get emotionally hurt as a result of this hookup? Very

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? Very much

Why do you regret this hookup? I didn’t ever want to experience sex in this way. I want partners who are present with me, not treating humanity as something to get past in order to get laid.

What was the BEST thing about this hookup? Exploring various things I liked in bed

What was the WORST thing about this hookup? Wondering if I had done something wrong/was unattractive

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Casual sex isn’t for me, and I need some boundaries when it comes to dating instead of going along with what comes up. If I have sex again, I need a clear motivation for it.

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

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

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 just wish we were all more comfortable communicating with each other. After this I realized I needed to communicate with partners before sex, but also needed them to communicate with me. You CAN ask for just sex if that’s what you want. It’s not shameful. It’s also not shameful to have sex early on in a relationship.

What do you think about the Casual Sex Project? I think it’s vital to share our stories with each other, and writing out my own is useful to me!

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