What’s your gender? Man
How old are you? 32
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

Former High School Girl

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 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? Amber and I went to school together. She is around 5’4″, long dark brown hair, fairly slender, a cups and a decent ass. I tried to hook up with her back in high school but she was one of those prissy girls and didn’t even give me the time of day.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was at the bar just down the road from my house last night. It was around 9 pm. I was sitting at the bar when Amber and another girl walked in with her. They came in and ordered drinks next to me at the bar. I recognized Amber but she either didn’t recognize me or pretended not to. They went to a table. A couple minutes later Amber came up to order more drinks and I said hi to her. She said hi back. I asked if I could buy her and her friend their drinks and she said sure. She took her drinks back to her table. About 20 minutes later Amber came back up and sat next to me to order another round. We started talking while waiting for the bartender to come over. She introduced herself as did I. I paid for her next round as well and she thanked me and went back to the table. Amber and her friend then came up and joined me at the bar. Her friend sat to the opposite side of Amber and Amber was next to me. We continued our conversation we had started. It probably was awkward for her friend as she was kept out of the conversation. Amber told me she had 3 kids and that she was divorced. I knew she had 3 kids and that she was still very much married. We did some shots at the bar. I asked Amber if she wanted to dance and she said yes. I said her friend could come to and she said no thank you. Amber and I went to the small dance floor they had there and danced to a few songs. Amber seemed pretty tuned up. We kissed a little while dancing but nothing that would have been considered making out. I grabbed her ass on the last song and she smiled at me. We walked back to the bar and sat back down. I asked her friend if she needed a drink. I got both girls and myself another drink. We ended up staying until bar close and called a taxi. We talked about just sharing a cab as they lived in town. I told them I lived just outside of town. When we got to her place her friend got out and Amber asked if I wanted to come inside for a while. I said sure. I went inside with the girls and we went to the living room. We all sat down on the couch together. Amber asked if I’d like to watch a movie with them. I said sure and she put on Netflix. Amber came and sat next to me and I was leaning against her friend. Her friend didn’t really seem too into what was going on. Amber and I ended up making out while her friend was beside us. Amber went over to her friend and they started to make out. Amber said we should go to her bedroom. I followed Amber and her friend.

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? Once we got into the bedroom, Amber began pulling off her clothes and got down in front of me. She unzipped my pants and pulled out my cock. She wrapped her lips around it nice and tight. Her friend stripped down to her bra and panties and got under the covers. Amber said I should get a condom from the dresser. I grabbed one as she slipped under the covers with her friend. They were making out while I rolled on the condom. I crawled under the covers and got between. Amber’s legs. She was busy kissing her friend when I pressed into her. She let out a moan and arched her butt up at me. I pinned her down and started to talk to her. I was pounding away watching these two make out. I reached over and began to rub her friends pussy through her panties. She didn’t seem to mind too much. I kept fucking Amber and noticed she was pretty quiet. That’s when I noticed she had passed out. It saddened me as I was hoping to fuck her brains out. Her friend, on the other hand, was awake and had a nice warm wet pussy for me. I switched over to her friend. She had red hair, nice b cups, also petite and pretty cute. I knew nothing about this girl not even her name. I grabbed her underwear and wrapped my hand around it and gave it a strong tug. I ripped her underwear right off her body. She pulled me down so I could enter her. I pushed inside of her vagina. We made out as I fucked her deep. She was really enjoying it and within a few minutes came hard. She wrapped her legs around me and clenched down on me. After she came, she asked if I’d fuck her doggie style. I was happy to oblige. She got on all fours and put her legs out. I was lining up with her hole when she told me to stop. She said she was so turned on not knowing me or anything about me. She asked me to take to condom off and fuck her raw. I pulled the condom off and pushed inside her waiting hole. I grabbed her hips and went to work on that pussy. She had an amazing was that when I pounded her moved with the motion. I pounded her what felt like forever and then started to get close. I let her know and she just said mmhmm. I took that as I should just shoot it in her. I kept pounding away as I started to cum. I shot my load into her and then we collapsed on the bed together with me still inside her. We laid there until I eventually got soft enough and slipped out. She turned around and kissed me and then went to the bathroom. She came back and the 3 of fell asleep in the bed.

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? The next morning we were all hung over a bit. Amber’s friend was up in the shower already. I spooned Amber in the morning and rubbed my hard cock against her bare pussy. She reached back and stroked me a bit and said she wasn’t feeling that great this morning. I kept rubbing on her pussy. She slowly got wet from me doing so and I eventually slid inside her. She moaned as I did and either didn’t mind or didn’t know I was not wearing a condom. I fucked her like this for about 10 minutes before she had an orgasm. She said she had to go to the bathroom as she was going to puke. I made my way into the bathroom a short time later and joined her friend in the shower. Amber was laying on the floor on all fours puking. I kind of wanted to shove it in her but figured I could just fuck her friend again. I went inside the shower still hard as a rock with some of Amber’s juices on me. Her friend was happy to see me and we began to kiss. She stroked my cock as we kissed. She leaned over against the wall and I pressed into her waiting pussy. It was kind of an odd angle due to the size of the shower but still felt good. I couldn’t really slam her and that was disappointing. She must have felt the same way as she turned around and got down in front of me. She gave me a bj that was amazing. It didn’t take too long for me to get close either. I let her know I was close. She told me to shoot it across her face and in her mouth. She told me to call her a slut when I did it too. I stroked myself and shot my load. The first shot went right into her mouth and the following ones across her face and breasts. I made sure to call her my dirty slut as I came. She wiped all the cum off of her and swallowed it down. We finished showering together and got out. Amber was back in bed. Her friend was getting dressed next to the bed. I was still horny and pretty hard still. I climbed into bed and got between ambers legs. She woke up and said really you want to still. I said yes. She said ok go ahead. I pulled on my cock and got out some of the cum that was left in me to use as lube. I rubbed my cock up and down her pussy before pushing in. It didn’t take long to get back to full hardness again as I fucked her missionary. Her friend just stood there and watched as I fucked amber. Her friend was rubbing her pussy through her panties. It was super hot. I put up ambers legs and pounded her deep and hard. I got close and didn’t even bother to tell her. I just shot my load inside her and pinned her down as I did. She got mad when she realized I wasn’t wearing a condom. She rushed to the bathroom after I was done. I got dressed and left with her friend. She gave me her number and said we should hook up again but no names would be preferred.

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

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

To whom did you talk about the hookup? How did they react? A couple of my friends from high school who knew her

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Finally got to bust one in her. Her friend was amazing and was very dirty in bed

What was the WORST thing about this hookup? She wasn’t that good of a lay after all the years.

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

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

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