What’s your gender? Man
How old are you? 29
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Philidelphia
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Research
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Player
How many sexual partners have you had in your life (including oral sex)? +40
How many hookup stories have you here posted before? 0
How long ago did this hookup happen? 6 months 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 year
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? Jess is late 20s, size 34DD tits, brunette, married, cute but not a supermodel. She gave birth 3 months ago and still has a little baby weight but in the places I like. When she wears tight slacks to work her ass looks sexy. Her tits are still swollen because she breastfeeds. I know that because she’s constantly taking breaks to pump.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Jess and I had been working on a project together and I knew she was having some issues at home. After giving birth her husband has been avoiding her. I didn’t know what she was hinting at until we were working late together and she let it slip he hadn’t ‘been with her’ (in the biblical sense) since she gave birth. Jess knows I have a reputation with women but I’m also respectful of her because she’s married. To cheer her up, I began a little harmless flirting and complimented her body. She had been wearing baggy clothes but once I started flirting and checking out her ass, she began wearing tighter clothes. At first, I made sure not to cross any lines but she gave me the ‘green light’ and said she didn’t mind and loved the attention.
It was time for us to travel to DC to present our project to a prospective buyer. Jess made plans with her parents for child care and we were off. We sat next to each other on the plane. I got bold and put my hand on her thigh. She put her hand on mine and squeezed tight. We checked in the hotel. Our rooms were on the same floor but not close. I stopped at my room but watched Jess’s ass as she walked down the hall. She looked at me and smiled then began walking with an extra sway. We had 2 hours to prepare for the presentation.
I changed clothes, grabbed my laptop and bag then went to the lobby. My eyes lit up when I saw Jess. She’d applied make-up, lipstick and was wearing a pinstriped business skirt outfit. She liked the attention. We rode the Metro and it was standing room only. She was stood next to me and don’t know why but I reached down and put my hand on her ass. It wasn’t firm but felt very nice to squeeze. Now, I had one hand on the bar and one on her ass. She put both of her arms around my waist and laid her head on my chest until our stop. The presentation went well and afterward we ate at a small sandwich shop. As we were leaving, I purchased two bottles of local wine from the gift shop and we went to the hotel. It was early and neither of us had plans. Jess loved the conversation and asked if she could come to my room later to try the wine and maybe watch a movie. Being flirty I said, “You know how I am with beautiful women. I might try to take you to bed.” She winked ran her hands in her hair and said, “That’s a risk I’m willing to take.”
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? An hour had passed and I heard a knock on the door. Jess was wearing a pink work-out tank top and yoga capris. My eyes almost popped out looking at her tits. I had the wine chilled and poured her a glass. We tried to find something to watch but switched it to a soft music channel.
We both leaned in and kissed. She pulled my cock out of my shorts and began to suck it. I could tell she wasn’t experienced but I was cool with her attempt. I’ve plenty experience with women and I know what Jess needed. A long oral session. We went to the bedroom and I went down on her. She was shocked at first but relaxed and let my tongue pleasure her. Her body motions told me she was loving it. I kept it up till she had an orgasm. I stood up and she begged me to fuck her. I asked if she was sure and she said, “I’m Positive!” I rammed my cock inside her wet pussy and we began having sex. She was vocal with moans of pleasure as I kept up the pace. She had amazing rhythm and I was making attempts to get off too soon. She got on top and I began playing with her tits. They felt warm and firm. She was grinding her hips onto my cock. She was forcing my cock to go deep inside her. I started licking her nipples then I squeezed it at same time. WOW! I felt her breast milk hit the back of my throat. I continued and each time she would grind harder until she had an intense orgasm. When she finished she looked at me and grinned. I asked if I should give her other tit the same attention and she said, “I wish you would or it will start to hurt.” I sucked and she squeezed until she said they felt better. She bent over the bed and we did doggy till I finished.
We had the typical small talk: no regrets, it was just sex between friends, we both wanted it, this was a one-time thing, let’s keep it a secret…. I offered to refill her wine glass but I was too late. The awkward pause kicked in she went to her room.
30 minutes later she sent me a text thanking me for a wonderful evening. We began sexting. I got bold and sent, “this bed would look much better with a beautiful naked woman in it tonight.” I got no reply but within seconds I heard her knock on my door. We had sex longer this time and Jess was very passionate then we went to sleep.
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? So far, we’ve hooked-up one more time.
Things were normal when we got back and we worked on a few projects together.
6 months had passed and on a Saturday I got a text from Jess. Her parents were babysitting and her husband was called in to work. (she told me later it was for a 12 hour shift breaker) She asked if she could come over and talk over a glass of wine? I replied, “Sounds great!” They had been going to counseling and I thought she was needing to vent. I was actually hoping this was a booty call. I texted my friends to cancel my tee time and did some light house cleaning.
She arrived wearing a thin white sun dress, heels, and carrying a wine basket with two bottles of wine. Her legs were tan and looked amazing! Once inside, she kissed me and we had passionate sex. I live in a condo at a golf resort so we spent the day drinking wine & talking in a gazebo. Before she left, we went back to my place and had amazing sex again. BTW: She’s still lactating!
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
How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it
What substances did you consume? Alcohol
How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it
What substances did your partner(s) consume? Alcohol
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
How would you best summarize people’s reactions about this hookup? I didn’t tell anyone
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? Having the opportunity to experience passionate sex with a good friend. Sucking breastmilk from her tits!
What was the WORST thing about this hookup? Having to use a condom. Jess is not on birth control because she’s breastfeeding and wants to keep her body clean of chemicals. I would love to have sex with her bareback and unload my sperm in her womb.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve never been in a committed relationship and I’ve rarely had sex with the same person twice. I enjoy sex for the pure pleasure and excitement of being with different people.
I think Jess needs sex as an emotional outlet because she can be very passionate. A new experience for me and I enjoy it.
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? I thought Jess and I were ‘one and done’ after our first sexual encounter. Then six months passed and the second time occurred (a few days ago). I’m still puzzled as to what’s going on in her personal life. We spent the day talking but her personal life was never mentioned as a topic of discussion. She’s a good person and if she want’s to hook-up again, I’ll be available.
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? My attitude toward casual sex has always been the same. Enjoy life and experience different people. A relationship is something I’m not interested in pursuing at the moment.
I think Jess is realizing people can have sex but still be in a committed relationship. She’s told me numerous times she would never divorce but during sex, I can tell she pours her heart and soul into the moment.
What do you think about the Casual Sex Project? It’s a great idea! It’s a nice place to share experiences.
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