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What’s your gender? Woman
How old are you? 34
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (open)
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 40
How many hookup stories have you here posted before? 1
Business and Pleasure
How long ago did this hookup happen? 3 years ago
What was your relationship status at the time? Same as current status
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? I met “Matt” through a local hookup website. He was actually from across the country, but traveled to the east coast almost once a week for work. He was very intriguing in written form, and it seemed obvious in the e-mails and phone calls we shared before his next trip here that we would have a lot of chemistry between us.
I met him at the hotel he stayed at when he was working here. We had shared some photos and descriptions of ourselves, but I was still surprised by his height. He was like 6’7″, and kinda nerdy in a cute way. He carried himself well, and that was such a turn on for me.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He was staying in a suite, so we sat on the couch for a bit just carrying on a light and non-sexual conversation. I felt too shy to make the first move, and felt relieved when he finally did. He leaned in to kiss me, and things quickly escalated from there.
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? It didn’t take long before we were naked and in the bedroom. He definitely had a dominant way about him, and he instructed me to lay back. He spread my legs and began performing oral on me. He was a little rough and overzealous to begin with, but he did respond well to my cues and movements, and I was able to cum.
He then crawled up my body and placed his cock right in front of my mouth. I laid on my side and began performing oral on him. He kept one hand on the back of my head to guide my movement, and he fingered me with the other. I asked him to go down on me again, and so in a very graceful move, he straddled my face and buried his face between my legs. I was able to take his fat cock deeper into my throat from this angle, and he enjoyed fucking my face while I came on his again.
He instructed me to get on my hands and knees at the edge of the bed, and while I obliged and positioned myself, he put a condom on. I had my ass right up in the air, and I looked over my shoulder at him and begged for him inside me. He grabbed my hips tightly, and slid into my pussy. He was SO thick, and it felt so good.
He clearly paid attention to our e-mail exchanges, especially the part where I said I like it rough, and that I love my ass played with. He fucked me so hard that it was actually hard to brace myself. He grabbed my hair with one hand, and started playing with my ass with the other. As he slid a finger inside my ass, I reached down between my legs and played with his balls, and ran my fingers along his cock as it slid in and out of me. When he was about to cum, he pulled my hair tightly so as to arch my back and allow him deeper inside me. His orgasm was intense. He actually yelled that he was about to cum just before he did, and he was sure to press himself so deeply inside me that I could feel his cock pulsate.
He finally let me collapse on the bed, and he laid right on top of me, and remained inside me. He nibbled at the back of my neck and shoulders, and I found myself grinding against him, hoping he’d get hard again and fuck me. I could actually feel him growing hard inside me. He slid his hands under my body to tug on my tits and he started to fuck me again.
I asked him to let me ride him. He rolled over onto his back and I climbed on. He immediately started to fuck me from underneath me, and eveytime we slammed into each other I felt a bit of pain as he was so deep inside me. It was a good pain though, and I did cum again pretty easily. His second orgasm took longer, and he yelled about it again, which I found so hot.
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 met up several more times in the next month or two, and kept good contact while he worked here. Unfortunately, the Governor of my state really pissed off the owner of his company, and the 1.5 year contract that they had with the state was severed, and he never came back. I do still look back very fondly on these times. He was hot, fun, and we clicked well while keeping things casual.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, IUD (Intrauterine device), Discussed STI testing history
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Submission / Relinquishing power
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 gave enthusiastic consent
To whom did you talk about the hookup? How did they react? No one.
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? He was so much fun, and it was a great release for me.
What was the WORST thing about this hookup? That it ended so soon. We both knew it eventually would have to, but it ended far too abruptly, and we had talked about doing so many things that we were never able to try.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No. I have always been a proponent for casual sex.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
What do you think about the Casual Sex Project? A great way to share personal experiences anonymously, since I don’t really talk about it with anyone else. I also find it validating to read so many other similar stories from people.
You have a hookup story to share? Submit it here!