Kaylee

by Fitnessguy

What’s your gender? Man
How old are you? 33
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What’s your current relationship status? In a serious relationship (monogamous)
What’s your sexual orientation? Heterosexual

Kaylee

How long ago did this hookup happen? Last weekend

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? One-night stand

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? Kaylee is around 5’5″, long brown hair, green eyes, nice b-cups and very cute. She has been dating my friend Todd for the last couple of months and that’s how we met each other.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A group of us went out on the boat this last weekend and ended up on a sandbar out by one of the resorts. Kaylee was there wearing an orange bikini with thong bottoms but Todd was not there. We drank quite a bit and then ended up playing football for a while. I ended up back over next to the boat by Kaylee. We were standing against the boat talking amongst ourselves. She asked where my gf was at and I said at home. I asked about Todd and she said she didn’t know. She told me she missed seeing me as Todd and her had not been around much lately. I said I missed them too. She asked if I missed seeing her specifically. I said yeah. She drank some more of her beer and it was an awkward silence for a bit. I kept looking over at her body and it was amazing the shape she was in. She finally caught me looking at her. She didn’t really make a facial expression. She cupped her breast in her hands and squeezed them then laughed. I laughed too. She leaned over and asked if I wanted to see her tits. I said sure. She pulled her bikini top to the sides and let her tits out. They were really nice and looked like implants. She just left them out and kept talking to me. I could tell she was really drunk at that point. She asked if I thought they were real or not. I said I couldn’t tell for sure. She told me to touch them. I looked around and everyone was so caught up in their own conversations that no one was paying attention to us. I reached over and felt her tits. They were nice and firm. She smiled at me. She left her tits hanging out still. I was rock hard in my swim trunks. She apparently noticed this and reached over and started to rub my cock in the water.

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? Kaylee moved closer to me and put one arm up on the boat and the other one down at her side. She slipped her hand into my swim trunks and started to stroke my cock. It didn’t feel the greatest as she had an odd grip and it was obstructed. We kept talking like normal with everyone else around us. I put a hand down and pulled her bottoms to the side. I slipped a finger into her vagina and began to finger her. She really seemed to like that. It went like this for roughly 10 minutes before everyone said it was time to head back to the house. Kaylee and I adjusted ourselves and we climbed into the boat. We ended up on the front. Kaylee laid down for the ride. I sat down next to her. Everyone else was sitting down drinking and talking. My buddy Chad was the one driving the boat. After we started to head back Kaylee started to rub my cock again. She got me hard and worked my shorts down. She then wrapped her lips around my cock and began to suck me. Chad had a full view of this and just gave me a thumbs up. I wrapped my hand around Kaylee’s hair and started to guide her pace. Unfortunately, we got back to the house before I was anywhere near cumming in her mouth. I pulled up my trunks and helped Kaylee off the boat. We pulled out the grill and everyone was helping make food. Kaylee said she was going to go shower before she ate. She looked at me as she walked down the stairs. I said I was going to run out to the garage and get more beer. I went out the front door and circled around back and went in the downstairs patio door. I bee-lined it for the bathroom. Kaylee was already in the shower when I walked in. I stripped down and locked the door. I hopped in the shower with her. We immediately started to kiss. She lightly stroked my cock as we did. She then got down in front of me and started to give me head again. She only did this until I was good and stiff. She then stood up and told me to put it in her. She leaned over the small counter in the shower. I rubbed her vagina with my hand and she was super wet. I still spit on my dick and pushed inside her. She felt amazing. I fucked her like this for several minutes before she reached back and grabbed my arm. She said she was cumming and I could feel her tighten up. I kept fucking her through the orgasm. She then stood up and turned around she put one leg up and guided me back into her. She then put her leg down and pulled me with her to the wall. We kissed as I pushed in and out of her. She felt amazing. It didn’t take long before I got close. I let her know I was going to cum and she said to pull out and shoot it on her face and in her mouth. I pulled out and she got down in front of me. My first shot hit her on the forehead before she got her lips around me. She grabbed my ass and jammed my cock into her throat. I finished unloading into her throat. She rinsed her face off as I got out and dried off. I got dressed in my trunks and went and got the beer and came back in.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? Everyone ended up staying at the house that night. I was hoping Kaylee would have snuck into my room during the night but she didn’t. I was the first one up the next morning and grabbed a couple of beers and headed out to the dock. I was sitting in the boat drinking when Kaylee came down. She joined me on the boat and I gave her a beer. She said she was hungover as shit. She said to please not say anything about what we did the day before. I said no worries. I asked if she enjoyed it and she said she didn’t really remember too much of it. I told her what we did as I was not as drunk apparently. She asked if I enjoyed it. I said yes I did. She smiled at that. I asked if she enjoyed it. She said from what she remembered yes. I made a move and leaned over and kissed her. She was a little caught off guard but responded back. We kissed for a few minutes before I asked if she wanted to fuck. She said she would but just didn’t want to get caught. I said we were the only two up. She said ok but asked if I had a condom. I said no. She asked if we used one the night before and I said no but I pulled out. She said ok that is fine. She came over and sat on my lap we kept kissing. She stood up and pulled down the shorts she had on. She was not wearing any underwear. I pulled down my shorts as well. She licked her fingers and ran them along her pussy before lowering herself down onto me. She sank deep onto me. She rode me as we kissed. We fucked like this for about 15 minutes before she came. She whispered in my ear she wanted me to cum. I asked if she meant inside of her and she said yes. She kept riding me as I tensed up and started to unload inside her. We sat there like that for several minutes after kissing and talking. She finally got off of me and put her shorts back on. She sat back down next to me. She said she really enjoyed having sex with me. I said the same about her. She said Todd and her were having issues and maybe she could come over more alone if we have further parties.

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)

How intoxicated were you? Completely Wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Completely wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

To whom did you talk about the hookup? How did they react? Chad later on as he had seen some of it. He thought Todd was a douche so he didn’t care. He was jealous as he thought Kaylee was hot.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Great kisser and great at sex

What was the WORST thing about this hookup? She’s dating my kind of friend

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? Love it

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