Naked Surprise



What’s your gender? Man
How old are you? 22
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What’s your occupation? Student
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Jewish
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 5
How many hookup stories have you here posted before? 2

Naked Surprise

How long ago did this hookup happen? About a year 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 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? This is the same ex I wrote about in another story “A Pleasant Surprise”.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? This hook up began a few days after we broke up. She came over and really wanted to get back together, but I wasn’t really thinking about that yet. I told her we could do other stuff first before that. She said ok, and that she had a surprise for me. She said she wanted me to wait outside my room while she got it ready. When she told me I could come in she was laying on my bed in only a push-up bra and a thong which she almost never wore. She told me I could do whatever I wanted.

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 closed and locked my bedroom door, walked over, and climbed in bed with her. I had her lay down on top of me as we began to make out and dry hump. I was grabbing her bare ass and slapping it hard since none of my roommates were home. I could already feel through my pants that she was beyond soaked. After a little while, she ripped my shirt off. I asked her to pull my pants and boxers off and swallow my fully erect cock. She pulled my pants and boxers off, but she said she would in a second. She began to dry hump me again through he thong. It was even wetter than I thought it would be. She began to heavily moan as we were doing that. After a while, she did go down on me and started to deep throat. Every time she did she gagged a bit which I found hot. Before she let me finish I had her stop and pull her thong off. I had her sit on my face and  69 with me. This is the only time we ever finished at the same time. She squirted all over my face while I came in her mouth and she swallowed it all to my surprise as she hated the taste. After a few seconds of me continuing to eat her out as she sat on my face, I was fully hard again, and she noticed when she reached back a bit and could feel it. I had her sit on my cock as I trusted upward as she screamed with pleasure. She squirted again, but this time on my cock which was hot. During this, I pulled her bra off for the first time and it was amazing to see these triple Ds bouncing up and down as I played with them and sucked on them. I eventually finished inside her which felt amazing.

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 continued to hook up on and off until I got into my next relationship.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, To feel better about myself, To feel more confident, To cheer myself up, I was feeling lonely, Boredom, Just happened, I don’t know why, just went along with it, It was easy / convenient

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? Very

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? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? That she wore a thong, and push up bra, and that she let me finish on her.

What was the WORST thing about this hookup? N/A

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nope

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

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

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