Caitlyn

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

Caitlyn

How long ago did this hookup happen? Saturday night

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 more than 3 years

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? Caitlyn is a very petite redhead I’ve known for over 10 years. She was a friend of my ex.  She weighs around 100lbs, has very small A cups, a very small round ass, around 5 ft tall and is pretty damn cute. I wanted to fuck her back in the day but never got the chance.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I went to my buddy Mark’s house this weekend. He had a small party with a bunch of people I knew and some I had never met. There wasn’t a lot of good looking girls there at the party. We all decided to walk across the street to the bar and drink there. We hung out for about an hour before we headed back. Mark told me some more people were on the way over. Shortly after a couple people walked in. One was caitlyn. She had on a hoodie and jean shorts. We all said hi and went down stairs. We ended up playing some drinking games for a while. Caitlyn kept looking at me and I was looking right back. We decided to go back across the street to the bar. On our way there Caitlyn came and walked next to me. She asked if I used to date Amber. I said yes. She said she thought it was me but hadn’t seen me in like 10 years. She told me I looked good and I told her the same. We went into the bar and Caitlyn and I went to the bar to get some shots. We sat, drank, and talked. She talked about her and her boyfriend basically the whole time and how many problems they had. It was really a turn off but I stayed because she was cute. Everyone else was busy drinking and playing pool. I asked Caitlyn if she wanted to go back to the house and talk more. She said sure and we walked back together. When we got to the house she talked some more about her relationship problems and then asked if I was staying down at Mark’s tonight. I said yes and that I had my stuff in the front room already. About that time everyone walked in from the bar. I didn’t realize it was just after 1 already. People started heading off to bedrooms. Caitlyn’s friends came over and told her they were leaving. Caitlyn got up to leave and was talking to her friends. I started looking around the room to see what girls were left to try and hook up. Caitlyn seemed upset at her friends and ended up going outside and making a scene. The one guy that was with her came over and sat down next to me. He told me Caitlyn wanted to stay and hang out more but they had to go. He told me if I wanted to hook up with her she was down and she said she liked me a lot. I asked about her boyfriend and he said they were actually broken up right now. I went outside and found Caitlyn sitting on the step. I asked her if she wanted to stay and she said yes. I offered to drop her off the next day if she wanted to. She got up and gave me a huge hug and we went back inside. Her friends left and I said I was going to get ready for bed. She asked where she should sleep tonight. I told her there was enough room in the bed for her if she wanted to sleep in there too. She said of course. I went and brushed my teeth and went into the bedroom. Caitlyn was already under the covers. I turned off the light and stripped down to my boxers and crawled in next to her. She immediately shot over to me and cuddled up next to me. I wrapped my arm around her and could feel that she only had on a bra and panties at this point. I could smell her alcoholic breath close to my face and pushed my face forward. Our lips met and we began to kiss. She was a really great kisser. As we were kissing I felt her hand start to rub my stiffening cock. She pushed back the covers and moved her way down my body.

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? I felt her fingers hook around the sides of my boxers and pull them down. I felt her little mouth come down and wrap her lips around my cock. She swirled her tongue around my head and then began to bob her head. It was really hot hearing the little slurping noises she made as she did it. Suddenly the door opened and my buddy James walked in the doorway with some girl. Caitlyn either didn’t care or seem to notice and didn’t stop sucking me. James just gave me a thumbs up and his girl just starred at my cock in caitlyn’s mouth. They walked back out and closed the door. I told Caitlyn I wanted to fuck her. She made a pop noise as she pulled her mouth off my cock and slid up on the bed. I reached over and pulled down her panties. I ran a finger up and down her pussy. She was super wet and had a very small hole. I lined up with her and rubbed my cock with her juices before I pushed into her. She gasped a bit as I did. It took a few strokes but I eventually got all the way in. We kissed as I fucked her deep and slow. She bit my lip as we kissed. I reached under her and cupped her ass. I pushed in deep and pulled her ass towards me with each stroke. She was moaning and breathing heavy. After about 10 minutes of this she ended up cumming. It felt great having her little box clench down on me and I couldn’t hold back anymore. I pulled all the way out and then pushed back in as I came. I dumped a big load inside of her and it felt amazing. We kissed some more and then ended up cuddling naked and falling asleep.

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 woke up and James and his girl had come into the bedroom at some point and got into the other bed. I got up to go to the bathroom quick and came back. Caitlyn was laying on her stomach under the covers. I pulled the sheets back and just starred at her little ass. I climbed up on the bed with her. That is when she woke up. I grabbed her hips and pulled. She went up into doggystyle. I spit on my cock and shoved it in. I grabbed her hips and started to pound her pussy. We weren’t quiet by any means. I looked over and James was still asleep. I could see his girl had her eyes open watching the show. We fucked like this for about 10 minutes before we both came. She wrapped herself in the sheet and went to the bathroom.

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

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

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

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

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? Was exciting having someone watch us fuck in the morning

What was the WORST thing about this hookup? Wanted to fuck her little ass but didn’t have lube

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

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

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