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? Last 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 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? Caitlyn was extremely fit, long brown hair back in a ponytail, very cute with an amazing ass. I had hooked up with her before when I was out of town in the fall of 2018. I wanted to hook up with her again but never went that way for work again.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was out shopping last night when I ran into Caitlyn in the mall in my hometown. She looked amazing. He had on a fox racing sweater and tight blue jeans. When she saw me she was with a guy walking hand and hand. She had a big smile on her face. She came over to me and gave me a huge hug. The dude she was with was giving me the “who the eff is this guy” look. She said she couldn’t believe she ran into me and asked how I was. We talked a bit and she then introduced the guy she was with as her bf. He seemed like a douche but I shook his hand. He asked how I knew her. She said we were old friends from where she used to live. She looked back at me and said I just moved up to this area. I figured she must have gotten a divorce then. She couldn’t stop smiling and the guy she was with was pissed. I told her it was nice to see her and maybe we could catch up sometime. She said she would love that and I said it was nice to meet her bf and he didn’t say anything. I finished up my shopping and headed home. My gf said she was going to go out with friends tonight and I’d be on my own. I ended up looking through my old messages and found Caitlyn’s number. I wasn’t sure if she still had the same number and texted it. I got a response back saying it was her. I told her it was me and she sent back a smiley face. I asked if she had plans tonight. She said she was going to dinner with some friends of hers but would be free after. I asked if she wanted to meet up. She said yes she’d love to. I told her to just send me a message later. It was around 9ish when I got a message from her asking if I still wanted to hang out. I said yes. She asked if I could pick her up at the restaurant she was at as she had been drinking some. I stopped over and she hopped in my car. I asked what she wanted to do. She said let’s go somewhere and catch up. I asked where she’d like to go like to get coffee or a bar. She said a bed. It made me laugh as it caught me off guard. I said I was down. I ended up driving to a hotel right outside of town and getting us a room. We walked in and she jumped up onto me wrapping her legs around me.

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? We started kissing, she smelled really good. She said she was sad that I never came back through her town before but glad she ran into me today. We continued kissing. I carried her to the bed. I set her down softly on the bed. She leaned back and undid her pants and I helped pull them off. She pulled off her sweater as I got naked. She had really toned up and was even more attractive than before. She pulled me onto the bed and got on top she came down to me and we kissed. She lowered her self down and rubbed her bare pussy back and forth along the tip of my cock. It felt great and she was very wet. I grabbed her hips and tried to push into her and she pushed my hands off. She said not yet. She worked her way down my body and wrapped her lips around my cock. Her skills at giving head had not diminished a bit. She was amazing. She didn’t use her hands except to cup my balls as she pushed me down her throat. She didn’t have much of a gag reflex but she did tear up a bit as she looked up at me. It was super hot. It didn’t take long as like last time before I lost it and unloaded into her mouth. She eagerly sucked and swallowed all my cum. She kept sucking keeping me hard and then got on top. She slid down easily with as wet as she was. She leaned down and we kissed as she rode me slow. She moaned and had a cute little whimper to her as she took me in. She stared into my eyes intensely the whole time. When she started to cum she leaned down and moaned into my ear. She kept riding me after and said she wanted my cum inside her. That’s all I needed to hear. My cock tensed up and I shot my load inside her waiting pussy. She pressed down hard getting every drop she could out of me. She then rolled off the bed and went to the bathroom. She came out a short time later and got dressed. She asked me to drop her off at her friend’s place. I agreed. I drove her to her friend’s place and she leaned over. We kissed for quite a while and she said not to be a stranger and got out.

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? Haven’t texted her after yet but hope to make her into a fuck buddy.

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? Not at all (no alcohol or drugs)

How intoxicated was your partner? A little tipsy/high

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? Getting a 2nd chance to fuck her

What was the WORST thing about this hookup? Nothing

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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