Pleasantly Surprised

by John

What’s your gender? Man
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? United States
Highest education received: Some college (currently in college)
What’s your current relationship status? Dating casually
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 9
How many hookup stories have you here posted before? 0

Pleasantly Surprised

How long ago did this hookup happen? Last night

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Fuck-buddies / First of (hopefully) many

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? She is a 20-year-old, slim, Indian chick. She has soft eyes, soft skin, and tough hair, so basically the perfect women. I’ve been talking to her for about a month. She told me that because she just ended a long term relationship, she was not currently ready for romance or another relationship. We’ve made out twice before this and went on a date, but I’ve been keeping my distance.

During the 4th of July weekend, my parents threw a party at their house for their friends. I invited her and she arrived at about 8. I was nervous about her meeting my family, but it worked out to my advantage after she and my sister bonded a little. What really sent her off was that, until the guests (and my siblings) left, I was doing these gentle little touches up and down her legs, she really liked that.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The guests left at around 10. We were in my parents’ basement on the couch with no one else around. We start to make out immediately. A few minutes into making out, I started to become aware of how very into me this woman had become. Maybe it’s because I’m a good kisser, maybe it was meeting my family, maybe it was the soft touches during the party. Either way, this girl was in an absolute trance. At that point, I was starting to think we might have sex, which was not part of the plan, but hey, 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? The make out session was getting heavier and heavier. During the process, I realize that her weak spot is the base of her spine, so I trace my fingers there as often as I can. I show her my weak spot (my neck) and after about 20 minutes of this, my cock was swollen. I asked, “do you want to take this to the bed room? We don’t have to use the bed, it’s just easier than the couch.” She says yes, so I picked her up, threw her on the bed, and then dragged her by the legs to me, that was all she needed. 10 minutes later, she started to take off her top and bra without even being asked. My shirt was already off, and I pulled her in close so we could touch chest to chest. Then I just worked my mouth up and down her breasts. I teased her pussy over her shorts until she was finally nodding for me to take them off. At this point, however, I am still trying to wait on having sex with her. Finally, I realize that this teasing is going to drive her insane so I asked if she wanted more but she was too flustered to answer me. All she could do was just eagerly nod yes. So I take off her shorts and panties. Wasting no time, I licked my fingers and gave them to her to lick as well.

When my fingers went inside her she bucked so hard. More fingering and a little clit sucking later and she doesn’t ask me, she tells me to take off my shorts, which I do. As soon as they’re off, she grabs my dick and I have to stop her from guiding me in. I still needed a condom. I took her off the bed (got half-dressed) and took her with me to get the condom that was in my car. When we get back, we start a quick forplay session and then she works the condom onto my dick. I fit inside her like a glove and I started going slow, making sure I got my whole cock inside her with every stroke. I’ve never had a girl cum from just my dick, but I must have done something right because she came instantly. It was only two, maybe three minutes in, when she came, and she came hard. She announced that she was close, and started to grab me tighter and tighter, scratching me pretty hard actually. Then, she said every man’s favorite words, ‘I’m cumming’. I watch intently as her eyes roll back into her head. I make sure to kiss her lips the entire time she cums, but she’s too distracted to kiss me back much though.

We kept fucking, mostly in the same position, with me on top of her, bracing myself on my knees, and her on her back. 5 minutes later she cums AGAIN and she was starting to feel bummed out that I hadn’t cum yet. So she laid me down and climbed on top of my dick and bounced. She leaned down and started kissing my neck. I started to get a warm feeling all over, as I was about to cum. I came hard and for a long time. Then, I slipped out of her and let her head to the bathroom. I took care of the condom and we laid down talking about how we needed to do that again.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

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? She kept saying how shocked and happy she was that we had sex and that she was sorry she came so quickly. We’re planning another date right now 🙂

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), Emotional intimacy, closeness, connection, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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

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 just mentioned it to my brother, but I spared him the details.

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

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Getting her to cum instantly with my dick. I thought it only happened in the movies.

What was the WORST thing about this hookup? Having to be quiet since we were at my parents’ house.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yah.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? She’s probably the most attractive women I have been with so far.

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 have yet to get to a 4th date without having sex. Like, sometimes I don’t even want it, but I’m not going to say no.

What do you think about the Casual Sex Project? <3 <3 <3

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