First Time & Desperate

by Jay

Gender: Male
Age: 28
Race/ethnicity: White
Current location: New York
Highest education received: College degree (eg., BA, BS)
Occupation: Import
Relationship status: Single
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Bisexual
How many sexual partners have you had in your life (including oral sex)? Approx. 25
How many hookup stories have you here posted before? 0

First Time & Desperate

How long ago did this hookup happen? 10 Years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Paid

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? I was just starting college and I was still a Virgin.  I met this Girl on campus the day before classes started and we were taking a bit. She ( Jennifer) was  about 5′ 8″ 140 lbs with a beautiful set of tits and an ass to kill for. Jennifer and I realized we were living around the corner so I invited her over for dinner that night. She was really attractive and was dropping very subtle hints that she liked me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Jennifer comes over for dinner wearing what I though was really cute it was a red dress that barely covered her boobs ( they were spilling out) with the skirt super short. I had ordered some Chinese ( college kids) and she brought some hard booze I had some beer. We were hanging out and she walked by to get something for the kitchen and she brushed by me a felt up my penis. I was turned on big time. I just kept on eating as not to give away I was desperate but I could barely hold back.

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? Issue she came back in went for it….I went in for the kiss and she came along for the ride. We had our hands all over each other. I was feeling her up and vice versa but then I got my fingers to her pussy she stopped me and said she needed cash for books. I agreed to give her some book money in exchange for two hours of her time. I gave her $400 and brought her to my room. I stripped her and started eating her out. She orgasmed twice and I had her give me a bj. The bj was ok and I blew a load down her throat. Oddly enough she swallowed my load.I then laid her out and started to fuck her (with a condom) I went for approximately 10 Minutes and then I rolled her over a fucked her doggy. I blew another load inside her. I then lay down and we relaxed for about an hour and a half. At this point she wanted to go because I had worn her out. She could barely walk.  I toldher no I still had another hour and I was going to use that time. She said no and I said then I want my money back and she would not. I demanded she lay back on the bed or I would take all the money I paid her.she lay back on the bed and I had her roll over and I had anal and vaginal sex with her another time each. I then ate her out and she gave me another blow job. ( I was on a heavy dose of viagra)

Did you have an orgasm? Did your partner(s)? She did in the beginning twice maybe more. I came about 5 times in the coarse of 5 hours.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condoms and found out she was on the pill

What were your REASONS for having this hookup? Desperate

Were alcohol or drugs involved? If so, how much? She had alcohol I had a beer.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Nothing we both cleaned up and she left. She then told me she was a part time hooker. Still unsure what part time hooker means. I felt sexually satisfied. Never again. The experience was enjoyable until she tried to rip me off.

To whom did you talk about the hookup? How did they react? Best friend.  Happy. Never told him about the part where I forced her.

Was this a consensual and/or wanted experience for you? For your partner? The beginning it was consensual for both and at the end only for me.

Do you regret this hookup? If so, why? Not really. It was a great way to lose my virginity but I was not happy that it was a Hooker.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Great sex. She was a Hooker.  No change other than I dont have sex with prostitutes.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

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