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What’s your gender? Man
How old are you? 27
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Some college (not currently in college)
What’s your occupation? Contractor
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 15-20
How many hookup stories have you here posted before? 5

Cassandra

How long ago did this hookup happen? 5 years ago

What was your relationship status at the time? Dating casually

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? Cassandra was a busty brunette with huge tits and a pretty big ass. She was a tad heavy but with her tits, it did not bother me at all. I was just coming out of my first long term relationship and had not really had sex with too many women. I met her at a meeting about a month before this happened. We started talking casually but one night she made some sexual comments that I was oblivious to. My one friend told me after the fact that she was flirting with me and i just laughed it off. I had her number so I decided to throw her a text.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We started sexting immediately. I hadn’t been with anyone but my ex in a long time and wanted something different. She knew how to tease me, ttelling me that we could not fuck until Friday night. This was Monday morning!!! I was so horny the whole week and she would text me and tell me what she was going to do to and what she wanted me to do to her. I pretty much walked around with a hard on all week. Friday comes and after I get out of work I call her. We make plans to go to dinner and a movie and get a hotel for the night. She pays for dinner and the hotel room. We went there right after dinner.

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? Once we got into the room, we start kissing passionately. I had not came all week so the build up was literally hurting by this point. She pushes me on the bed and pulls down my pants and admires my package for a bit. She knew how to build a guy’s ego!! She started blowing me and it wasn’t long before I was going to cum. I told her I was ready to cum and she went into overdrive. I must have shot a gallon of cum into this poor girl’s mouth. She started gagging and coughing and didn’t even finish before she ran into the bathroom, afraid she was going to throw up. I was laughing at this point and I apologized. She came back to the room a few minutes later and asked if we could go to the movies. I agreed and we went to see some cheesy horror movie. She took me to the family bathroom half way through and started blowing me again. I didn’t cum but it felt amazing. I suggested we wait until after the movie to finish. When we got back to the hotel we started kissing again. She took her pants off and laid on the bed and started playing with her pussy. Of course I was hard and slid my dick right in. She came almost instantly and kept cumming for several minutes until I pulled out and shot more cum on her stomach. We took a break and smoked a couple cigarettes. She then took her shirt off and her bra and revealed her GIGANTIC tits. She shoved them right in my face and I went to town on them. Biting her nipples sucking them, and licking them while she was moaning loudly. I started fingering her and she came again. She then started jerking me off and got on top of me. She rode me so hard my thighs were sore. She came a couple more times but I didn’t. I told her she drained me and we both laughed and went to bed. She woke me up around 3:30 with a blowjob and hopped on me again. I was half asleep when she started riding me and was kinda out of it. She kept saying she wants more of my cum, it tastes so good. I told her to get off and start blowing me again. This time she was more sensual then before. Going slow and deep and sucking my balls periodically. She kept jerking me off while licking my balls until I blew my third load all over her face. She told me she loved cum on her face. She licked up every drop and then passed out. I did too and left pretty early in the morning.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? We continued to fuck for several months. She was ALWAYS down to fuck. Even when she didn’t want to she would always suck my dick. She gave me a lot of “firsts” in my life. We eventually broke it off and no longer speak.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting

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? Very

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 didn’t give a clear ‘yes’, but didn’t give a ‘no.’

To whom did you talk about the hookup? How did they react? Everyone!!! I could not keep it to myself.

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

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? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Having fun casual sex with an attractive girl.

What was the WORST thing about this hookup? Nothing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? yes. After Cassandra I was more open to casual sex.

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

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

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

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