What’s your gender? Man
How old are you? 31
What’s your sexual orientation? Heterosexual

My Friends Girlfriend

How long ago did this hookup happen? 6 years

What was your relationship status at the time? Dating casually

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? Stacy was shorter around 5 ft 5. She had blonde hair that went down just past her chin and had bright blue eyes. She was a little curvy for her height but definitely not fat. She had nice double D tits. She had one of the most amazing asses I’ve seen thus far. She was dating one of my best friends who I have known my whole life. I was living with him at the time when they started dating. Eventually, she moved in with us. They had the room upstairs and I was on the main level. I thought she was super attractive and was a bit jealous.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was usually never home on nights as I worked most overnight shifts as did my friend. I took a week off of vacation and just planned on hanging around the house. The first day I was home it was super sunny and hot outside. When I got up I saw Stacy outside tanning. She had on her bikini which did not cover up her tits well. I sat and looked out the window as I ate just starring. Later that day she had just come out of the shower and I was on the couch watching tv. She came into the living room heading for her room upstairs. Her tits were hardly held inside the towel and it rode just at her ass on the bottom. She walked by and gave a little smile. I instantly got hard. She came back downstairs about 20 minutes later in a small crop top and booty shorts. She came and laid down on the floor in front of me to watch tv too. Her ass cheeks were hanging out of her shorts and I didn’t know she had a tramp stamp before but seen it now. I got hard again and just starred. Ahe asked if she could lay on the couch next to me as the floor was too hard. I got up and moved to the chair so she could have the couch. She had an odd look on her face and asked why I was hard. I got so embarrassed. I tried to think of an excuse but just said I hadn’t had sex in a while. She laughed at that. We watched tv in silence for a while. She then got up and went to the bathroom. I was so embarrassed and wanted to leave. When she came back in the room she had taken off her bra but had her crop top on. I could see the full shape of her breasts and her hard nipples. She sat back down on the couch and looked at me. She smiled again and asked what I was thinking. I blurted out how nice her tits were without thinking. She asked if I wanted to see them. I didn’t get a chance to answer before she pulled up her crop top.

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? They were amazing breasts. She asked if I wanted to relieve myself and she would play with her tits for me. I unzipped my pants and pulled out my hard cock. I watched her push them together and rub her nipples. She told me my cock was bigger than her bf’s and it turned her on. I asked if I could touch them and she agreed. They were amazing in my hands, I really squeezed them and then put my mouth on her nipples. She moaned a bit as I did. Then she pushed me back and told me to keep playing with myself. She got up and bent over in front of me. She pulled down her booty shorts exposing her freshly shaved pussy to me. Her pussy was beautiful with just a tiny slit glistening. She sat across from me and began to rub her clit and finger herself. I slowed down stroking and watched her pleasure herself. She only took about 5 minutes before her breathing picked up and she had an orgasm in front of me. I was so hard after seeing that. She got up and walked over to me. She knelt down in front of me. She asked if her bf had told me how much she enjoyed giving head. I shook my head no. She smiled and wrapped her hand around my cock and began to stroke it. She then lowered her mouth onto my cock. She sucked it slow and deep. She was really good at it too. I told her I was close and she took her mouth off and gave me a pouty face. She said she wanted me to hold it because she wanted to keep sucking. She took me back in her mouth and I lost it. I came so hard and she just kept slow and deep sucking motion on my cock until I emptied all my cum into her mouth. She swallowed it and kept sucking and kissing. She kept me hard and got me off in her mouth again.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? When we were both home, she gave me head on a regular basis if he wasn’t home. I fucked her about a month into it. I had to use a condom as she wasn’t on the pill she told me. It was pretty damn good too. They broke up about 3 months after we started hooking up. She moved out and I went to her place a couple times a week. We stopped hanging out once she got a new bf. The night she told me was going to be our last hookup she let me fuck her with no condom and it was so much better. I didn’t cum in her just on her stomach. I saw her last month in the paper for her wedding engagement.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Condoms

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

Do you regret this hookup? A little bit

Why do you regret this hookup? It was my best friends girl

What was the BEST thing about this hookup? Her bj skills

What was the WORST thing about this hookup? Had to end

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

You have a hookup story to share? Submit it here!