by DJ

Gender: Male
Age: 30
Race/ethnicity: Caucasian
Current location: Connecticut, USA
Highest education received: Some college (not currently in college)
Relationship status: Engaged
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Bisexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Bisexual recovering sex addict
How many sexual partners have you had in your life (including oral sex)? 45+
How many hookup stories have you here posted before? 11

Work Trip Fling

How long ago did this hookup happen? One year 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…)? One night stand

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? Cheryl was a sexy, kinda punkish, kinda goth, but very sweet redhead. She was just slightly overweight but still had a great hourglass figure, and amazing legs. Lots of tattoos and lots of piercings including on her clit, nipples and tongue.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was in Rhode Island for work, staying overnight in a hotel room. I was feeling horny and lonely, so I started browsing a dating site. I sent Cheryl a snarky message that clearly got her attention. I told her my situation and that I was only looking for fun. To my surprise, she was receptive to the idea. So she came to the hotel room within an hour of when we first started chatting.

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? She showed up and I was very pleased with her appearance. I found her petite body and punk rock look to be very attractive. We sat on the bed for a few minutes, chatting and shooting the shit, then she went outside to have a smoke. I got the feeling she was getting impatient, so I kissed her. She remarked how surprised she was that I kissed her. “I thought you were reconsidering and weren’t attracted to me”. I reassured her that I was incredibly attracted to her. We went back up to the room and immediately started kissing and tearing each other’s clothes off. I loved the feel of her pale skin on my fingertips and she had an amazing ass. She got to her knees and sucked my cock for a while, doing a great job sucking my balls and licking the shaft. I played with her tits and ran my fingers through her hair as she pleasured me. Then I decided it was her turn to be pleased. I went down on her, kissing her body all the way down. I licked her clit for half an hour, rubbing her g spot and making her cum very hard. She had a very sexy orgasm squeak. I then started to enter her tight wet pussy, all the while kissing her and looking her in the eyes. I love eye contact and she was very good at giving it back. It became very intense as we felt extremely close to each other, emotionally and physically. The tension was very intense. She climbed on top of me and rode me for a while until she came. Her ass felt great bouncing on my hips. I’ve had strong instant connections with women in bed, but none quite as overwhelming as this. We looked into each other’s eyes and could see into our souls. The feel of her pussy on my cock was just a compliment to the pleasure of that connection between us. We held each other close and kissed passionately like our lives depended on it until we both came together with me on top, thrusting deeper and deeper inside her. We ended up having sex a couple more times that night. She left around 2 AM.

Did you have an orgasm? Did your partner(s)? Yes we both did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Used a condom the first time but then decided we didn’t want to use one the next two times.

What were your REASONS for having this hookup? I was lonely and horny.

Were alcohol or drugs involved? If so, how much? None.

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 cuddled and talked a lot about everything. We laughed and joked a lot as well. The next day, I visited her when I had a break. She worked at a pastry shop and made me some pastrys and we talked and made out a bit. It was really sweet actually. We eventually saw each other again a few months later when I had to go back for work. The chemistry was still there, but my situation wouldn’t have allowed me to pursue a relationship. Not to mention we weren’t close. She remarked that she felt like she loved me that first night we were together. I said I felt it too. Maybe it was just hormones, but the feeling was intense. She moved away and I haven’t seen her since. I think about her almost daily.

To whom did you talk about the hookup? How did they react? My therapist and my friend. They both think that I am in love with the concept of love and that I use sex to make women fall for me. I don’t know. Maybe they’re right.

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

Do you regret this hookup? If so, why? Not at all.

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? Her body and our connection. The worst? That it had to end.

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 or anything else? I’d like to hear if anyone else has had any experiences where they felt love on the first fuck. Lol that sounds so stupid. I read all of these and I’d love to hear of any similar experiences.

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