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What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Accountant
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 13
How many hookup stories have you here posted before? 0

Underwear Modeling

How long ago did this hookup happen? 14 years

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For less than 6 months

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? Deborah was someone I knew starting my sophomore year of college. We had some classes together. She was 20 years old, 5’6”, brown hair, cute face and solid breast. We would often flirt with each other when we talked so I thought there was a possibility of something happening. She was a little bit of a bohemian type so I figured hooking up with her could be fun.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One Friday afternoon I had gone to the local mall in order to shop for some cloths including some underwear. After I was done shopping I saw her standing at the bus stop. Since I had a car I drove by and offered her a ride back to the dorms. She asked me what I had been doing and I told her shopping for underwear. She asked if she could see the underwear. I asked if she wanted to just see them or want to see me wearing them. She smiled and said, “Model them for me.” We went back to my dorm room. Thank God my roommate was always at his girlfriend’s place so I knew we wouldn’t be disturbed.

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? When we got to my room I went to the private bathroom our room had and changed into one of the boxers. I gave my cock a couple of strokes to get the blood flowing to make sure she could clearly see it outlined. Wearing nothing but the boxers I came out and so her sitting at my desk. I did a little twirl like I was a real model. She gave a sexy smile and told me to come closer. When I was closer she started running a finger under the waist band of my underwear. I started getting even harder and she could easily tell the effect she was having on me.
Finally, she pulled my underwear all the way off. My 7 inch cock was in full display for her to admire. Deborah said, “Very nice,” and began to run her hands over my cock and balls. After a minute of that, she bit her lip and looked up with a wicked smile. She took my dick in her mouth and started sucking. Compared to a couple of previous girlfriends she really knew what she was doing.
After a couple of minutes of sucking I stood her up and started taking off her cloth’s. Her breasts were even better than I thought. I picked her up and put her in the top of the bunk bed. I went to get a condom from my night stand and climbed in with her. We fondled each other and made out for a while. I went down on her and she came from that.
After that she sucked me fully hard again and put the condom on my dick. We first started off with her ridding me cowgirl. She really knew how to have fun from fucking. Later we switched to doggy and I came hard after a minute or two. She also came once from the fucking.

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? The next day I felt great about the hookup. We hooked up many more times after that. We both loved sex and neither of us had any hang-ups or issues with friend on friend sex.

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), Emotional intimacy, closeness, connection

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? I didn’t tell anyone but some people in our circle of friends knew what was up.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The best thing was sharing sexual pleasure with a friend.

What was the WORST thing about this hookup? There were no problems with the hookup.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The hookup convinced me that people who are friends can have sex with each other and it does not have to lead to hurt feelings.

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

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

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Casual sex is a great thing. The world would be a lot better place if we didn’t have so many hangups about sex and just enjoyed ourselves.

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