Oops I Did It Again

by P

Gender: Female
Age: 19
Race/ethnicity: White
Current location: New York
Highest education received: Some college (currently in college)
Occupation: Student
Relationship status: Single
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 0

Oops I Did It Again

How long ago did this hookup happen? 2 months ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? sex with an ex

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? My ex boyfriend and I broke up about 6 months ago and since then we have had sex a handful of times. He is tall and skinny with dirty blonde hair and green eyes. Very Handsome. We’ve stayed in contact since the breakup and remain close friends (despite the initial difficulties). Although our relationship is over we are still incredibly sexually attracted to each other. This particular encounter took place in his childhood bedroom (we go to the same university and were both home for the summer). After the hookup I initially felt happy/satisfied but then as time went on I started to feel regret and shame. I constantly struggle with this feeling after casual sex because of social stigmas surrounding it. I am a very sexual person and don’t want to force a long term committed relationship just because I want to satisfy my desire for sex. This is a constant battle against the societal standard that casual sex is wrong and therefore should not be done (especially by a young woman).

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was coming into his hometown to visit some other friends and so I let him know (via text) that I would be in town. Like I mentioned previously we are very close and so we arranged to get together (sex was not planned but I was secretly hopeful it might happen (and I think he was too)). We planned to meet at his house and then decide what we wanted to do/where we wanted to go from there. I arrived midday and he met me at the front door. We hugged and went to his room to talk and catch up. His parents and sister weren’t home. After a few hours of talking on the couch in his bedroom he started to touch my leg. I am the type of person that doesn’t act on something until I feel pretty confident in the situation so I let his hand move up and down my leg but did not acknowledge it. I kept talking like nothing was happening (I think I started talking about the weather at some point). Then I mentioned my hair (which I had recently cut short) and switched my gaze from the window to his face. He made some remarks about my hair and then raised his hand to touch it. At this point his face was really close to mine and he went in to kiss me. We started making out on his couch for a few seconds (him on top of me) and then we began to fall off of the couch so we moved to the bed.

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? After we moved our make out to his bed things started escalating quickly. He took my shirt off and soon we were both naked. He went down on me after sucking on and playing with my nipples (they are extremely sensitive). That lasted for maybe 10 minutes (or less?) at which point I was desperate to get his penis inside of me (he has a really nice penis – large and smooth). I told him to stop because I wanted him inside me and so he stopped and tried to put his penis inside me without a condom. I am comfortable with him but not stupidly so. therefore I told him he needed to put a condom on. He agreed completely and told me where they were (his desk drawer). I got a condom and came back to bed. I handed it to him (he was sitting against the wall on his bed) and told him to get it out of the package while I proceeded to suck his dick. He was extremely hard and I could tell he had a hard time telling me to stop giving him a blow job so that he could put the condom on. After he did we began to have sex missionary and talk dirty to one another. We switched to all kinds of positions (cowboy, doggy style, etc) and he was pounding into me hard. The sex is always incredible with him and I was n oorwetter than I can ever remember being before. We finished missionary style with my legs on his shoulders so that he could go really deep. He orgasmed and then the sex was finished. It lasted for a little over an hour.

Did you have an orgasm? Did your partner(s)? He orgasmed. I did not have an orgasm, I find that it is extremely difficult for me to achieve orgasm without the aid of a vibrator. Sometimes I can come from someone going down on me and fingering me simultaneously but today it just would’t do the trick. This was not to the detriment of my sexual experience – it was great.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used a condom and I have no STI’s (neither does he) – we talked about it when we were in a relationship.

What were your REASONS for having this hookup? We were both sexually frustrated and in need of release. As I previously mentioned we are still massively sexually attracted to each other so when we are both frustrated it is hard to avoid.

Were alcohol or drugs involved? If so, how much? No alcohol or drugs were involved.

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? After the hookup we lay beside each other and I rested my head on his chest and wrapped my arms around him (mostly out of habit). He seemed to get a bit spooked   by this and got up pretty soon after and started to get dressed. I followed suit. Then we talked and joked around for a bit until he checked the time and realized he had to pick up his little sister (he had mentioned this when we were originally making plans so I knew beforehand that he had to leave to do that). After that we went downstairs to his kitchen and he offered to make me something to eat (I declined as I was starting to feel like he was politely pushing me out). We talked for a little while longer and then I got the hint and said I had to go. He walked me to his front door and there was a slight pause as we said our goodbyes (unsure whether we should hug? kiss? handshake?). He broke the tension by taking me in for a big hug. I said I’d see him back at school and got in my car and left.

To whom did you talk about the hookup? How did they react? I talked to my sisters and a few close friends about the hook up. In the few days following it I couldn’t stop thinking about it but felt guilty because I knew I shouldn’t probably be having sex with this ex. I had an extremely difficult time getting over the breakup and struggled a lot with it. I knew that by having sex with him I was opening up old wounds and subjecting myself to possible heart break (again). After I told my best friend she echoed my negative thoughts and so I called him the next day to say that we couldn’t continue this type of relationship anymore. I felt like I owed it to my past (heart broken) self. I also wanted to protect myself (for I often miss him intensely after we have had sex post break up).

Was this a consensual and/or wanted experience for you? For your partner? It was consensual and wanted by both of us.

Do you regret this hookup? If so, why? Part of me doesn’t regret the hookup because it was fantastic sex and fulfilled my needs. However, I do partially regret it because of the emotional (past and present) implications. It honestly depends on the day (and how sexually satisfied I’m feeling).

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 part about this hookup was the sexual need that it fulfilled – it was extremely satisfying and felt really good. I felt like I was in charge of my sexuality and unapologetic w/r/t my needs and preferences. The worst part of this hookup was the guilt that oftentimes follows in the wake of a sexual encounter with this particular individual. This hookup illustrates the mixed emotions I have about casual sex for ME as an individual. Am I capable of doing it without getting emotionally attached? And if I’m not emotionally attached, will it still be pleasurable for me? I struggle with hookups for these reasons.

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

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

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