A Pleasant Surprise



What’s your gender? Man
How old are you? 21
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What’s your occupation? Student
Religious affiliation: Jewish
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

A pleasant surprise

How long ago did this hookup happen? 3 months ago

What was your relationship status at the time? Single

How would you best classify this hookup? Sex with an ex

How long did you know the person before this hookup? For 1 to 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? My ex and I were together for around two years before I broke up with her. We had met at school. She had a relatively large ass that was pretty tight as well. Her tits were Triple D which are always a plus for me. Her face was pretty nice. This hook up happened only a few months after the break up.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? This day it all began when she picked me up from work and drove me home. I thought we were still friends and she needed to pick things up, so she came in. She also needed to talk to me. There were no intentions for this to turn sexual at all.

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? One of my roommates was in the living room while we were in my bedroom. While we were talking I realized she was wearing a shirt that she knew always turned me on, so I reached down and just grabbed her ass. She kept talking like nothing had happened, so I pushed my luck and decided to move my hand into her leggings and grabbed her bare ass. Again she did not make any changes in how she talked, but she reached over and started to play with my cock over my pants.

Once we were done talking I was laying down in my bed and and comes and joins me. She immediately takes my pants off and just swallows my fully erect cock giving me an amazing blow job. After a few seconds of her moving her head up and down she looks up and says that she wants to give me as much pleasure as possible and blow me till I cum. I look at her and say that is perfect. As she continues I decide I wanted to see her tits. I have her take off her shirt and bra to see her massive tits. She continues blowing me till we here my roommate leave. I proceed to lock my front door and bedroom door and tell her we should 69. She excitedly agrees. I have her cumming and squirting within a few minutes. Since I had not finished yet she mounted me and rode me cowgirl until I finished. We sit there and cuddle a little bit before she goes back down and starts blowing me again, getting me hard. I fucked her doggy style til she reached another orgasm.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? At first I was happy to have had sex, but as time went on I realized she was still head over heels for me and I was not into her that way anymore. Before I felt that way through we did hook up two more times one of which was the best blow job she ever gave me (in her car). For a while she was sending me nudes until I told her we needed to stop everything we were doing.

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

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

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? No one.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? Very

Do you regret this hookup? Very much

Why do you regret this hookup? Because I hurt someone I still do consider a friend.

What was the BEST thing about this hookup? The fact that she gave me the blow jobs with out me asking as she hates giving blow jobs.

What was the WORST thing about this hookup? The fact that I hurt her.

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