Learning How To Do It

by Rob

Gender: Male
Age: 23
Race/ethnicity: Caucasian
Current location: New Hampshire
Highest education received: College degree (eg., BA, BS)
Occupation: Grad school
Relationship status: Currently single
Religious affiliation: Not religious
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 1

Learning How To Do It

How long ago did this hookup happen? 4 years 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…)? Fuck-buddies

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? Andrea was a thin, fragile looking girl with dark black hair, pale skin and a sort of former-goth aura. She also had a silly, kind of girlish quality to her. When I met her, it was clear that she had a troubled past and was probably not from a very well-off economic background. I went to college in Maine; she had lived in Maine her whole life. I was 19; she was 20. She chain smoked and listened to heavy metal. I met her at a party at the same house at which this story takes place. For some time in December and January of my freshman year, we dated. But then something changed in our relationship which turned us in to people who compulsively fuck each and not people in a romantic relationship. Also, she was the girl I lost my virginity to, although this is not that story.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was in the trailer home of her friend Sam, who hosted lots of parties. Andrea had called me, drunk, while I was at a different party in a friend’s dorm room. Apparently, some guy had been flirting with her and had made her nervous and she wanted to see me. I tried to resist coming over because she was interrupting a good time I was having. She tried saying that she was sorry, she was drunk, I didn’t have to come over… But I decided to anyway, probably because I felt like getting laid. I think I was still operating under the false pretext, at the time, that we were dating.

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? So I got a ride to this trailer home, a whole town away and arrived there after midnight. Everybody was drunk except for me. I found Andrea and she seemed happy to see me but not particularly affectionate, which I found odd. We hung around and drank some more. The party was winding down and the guy who had been hitting on her had left long ago. Andrea and I were eventually left alone in Sam’s living room on her pullout couch (no pun intended). We made it in to a bed and lay there, kissing. I asked her if she wanted to have sex and she teased me about the way I asked. “Do you want me? Are you sure?” she said. She said that of course she wanted me but I should just come out and say it to her. I undressed although I recall her keeping her t-shirt on. She was on the pill. With her help, I guided my cock inside her. But keep in mind that at this point I was still sexually inexperienced. I didn’t know that you had to stick yourself all the way inside a woman to make it feel good for her and best for myself. So I started lightly moving around with the tip of my cock inside her and she whispered, “…stick yourself all the way inside me.” So I did. She sighed and I started moving faster and harder than I had ever previously moved. She whispered, “Go as hard and as fast as you want.” So I went hard and fast. I started realizing that I was really fucking her this time; that this is how it was meant to be. The bed was creaking and the sheets were rustling and everything. I heard her breathing heavily, but she was trying not to make much noise because there were four other people sleeping in the house in rooms on either side of us. She held my back with one arm but didn’t look me in the eyes. My entire cock felt very wet and I could feel myself building up to a better orgasm than I’d ever had before. She sighed and whispered, “You’re gonna make me cum…” As if to congratulate me on a landmark I’d finally reached. I was surprised for a moment about how many orgasms that had to meant she had faked previously. But her words made me speed up even faster and I listened to her quietly exhilarated breathing in my ear and then came very heavily. Since I was still moving in and out of her, I slipped out and got cum all over the sheets.

After we had settled down a bit, she got nervous about what a mess the sheets were and said that we had to clean up now, that this was a part of sex. I suppose she knew that I had cum on the sheets but I wonder if she had gotten any fluids on the sheets as well. I helped her wipe down the sheets. We got back under the covers. I think I asked her if that was really the first time I’d made her cum. She said that previously I had made her feel good, but that was the first time I’d given her an orgasm. I accepted it and we fell asleep.

Did you have an orgasm? Did your partner(s)? I had the orgasm of my life, at the time. She also came, as evidenced by the story.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Andrea was on the pill. I didn’t have to wear a condom. We had previously, briefly discussed STD history. Both of us were clean.

What were your REASONS for having this hookup? I was a horny college student? I lost my virginity later than any of my friends, which made me sort of angry and want to overcompensate for it. At the same time Andrea was very promiscuous and troubled and this was an open secret among her friends. I think this knowledge made me more attracted to her even as I tried to ignore it, if that makes sense.

Were alcohol or drugs involved? If so, how much? She was very drunk. I wonder if she would have cum if she weren’t drunk. I was a little drunk.

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 slept, woke up, she gave me a ride back to my dorm. We kept hooking up for a little while afterwards, although keep in mind that she was promiscuous and moody and I was also somewhat depressed, immature, and didn’t always think about what I said to people. I occasionally said hurtful things to her and twice shouted at her on the phone. She used me for sex and manipulated me to a certain degree. Needless to say, we officially broke up not long after that night in the trailer home. Basically, we were both troubled people who weren’t entirely in control of our emotions.

To whom did you talk about the hookup? How did they react? This particular hookup? Nobody, really. Although one of Andrea’s friends said something to me shortly after, when I saw her, that I “bet I had a good night,” or something to that effect. Perhaps everybody heard us fucking, I don’t know.

Was this a consensual and/or wanted experience for you? For your partner? Absolutely.

Do you regret this hookup? If so, why? No. It was a normal sex act between two young people who don’t completely understand each other. I miss being able to do it without a condom.

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? Having sex without a condom and hearing her ecstasy. The worst was the lack of emotional involvement that at least I was pretending was there.

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

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

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