She Had a Huge Surprise



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? New York City
Highest education received: High school diploma
What’s your occupation? Sales Rep
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Jewish
How religious are you? Somewhat
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Into sexual freedom, exhibitionism, nudism etc.
How many sexual partners have you had in your life (including oral sex)? 25+
How many hookup stories have you here posted before? 1

She Had a Huge Surprise

How long ago did this hookup happen? 8 years ago.

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Paid sex

How long did you know the person before this hookup? Just met that day

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 obviously never met her before. I heard some people in the neighborhood complaining that there is a hooker cruising one of the streets in the neighborhood late at night. One night, I came home late from work and I decided to go check it out. When I passed through the street, I saw her walking in a very scantily clad outfit. She looked beautiful. She was tall, slim, nice tits and ass that were barely covered by her mini dress, with dark skin and dark long hair. I would later learn that she was Latin.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I drove around the block a few times and she noticed that I was looking at her. She gestured with her hand as if to ask what I want, so I slowed down the next time I passed her. My heart was pounding. I have never done anything like this before. I have never paid for sex and I definitely never picked up a street hooker. My original intention that night wasn’t to pick her up, but rather to just check her out, see what she looks like. But there was something about her that made me lust for her. I just couldn’t resist. When she arrived to the car, I rolled down the window and she asked what I want. I asked her how much and she responded “60 for blowjob, 120 for sex”. I told her that I hadn’t planned for this and I only have 40 on me. She thought for a second and then said that she will do a bj for 40 only if we do it in the car.

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? She came into the car, her smell was intoxicating and her looks were just a wonderful sight. She showed me to drive a few blocks, turn into a parking lot of an apartment complex and showed me to park in the corner. She started feeling me up right away, slipping her hands into my shirt and softly rubbing between my thighs. My cock became instantly erected and excited. Meanwhile I started playing with her tits, rubbing her body, which she seemed to enjoy. She guided my hand over her body till she gently pushed it between her thighs and under her dress. That is when I felt it! Between her beautiful feminine legs, I definitely felt a huge erect cock!

At first, I was shocked. I have never touched a cock other than a couple times when I was a little kid experimenting. But otherwise I have always seen myself as strictly straight with no interest in anything, but female tits, pussy, and ass. I looked at her with the greatest shock look on my face and she just shrugged and said, “I am a transsexual”.

Within a few short seconds, I noticed that not only was this not a turn off for me, I was even more turned on than ever before. I felt my whole body tingle as I played with her tits with one hand and her cock in the other. It was a nice thick 8 inch uncut cock! I asked her if I can suck it. She put on a condom and I sucked it for a few seconds and this got me even more turned on.

Meanwhile she took out another condom and put it on my cock. I was so turned on that I felt like I am going to explode, which I did 10 seconds after she started blowing me. She cleaned me up, took my money and left the car. I was in a daze and couldn’t drive for another 15 minutes.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? This encounter opened my eyes. I couldn’t stop thinking and dreaming of this woman’s huge cock. I dreamed of sucking her to her last drop, fucking her and being fucked by her. I also started checking out tranny porn and after that gay porn. That is when I slowly learned that I am bisexual and that I am equally attracted to men and women. I had other occasions to be with other transexuals and crossdressers and with many other sexy men, but I never met this girl again, I wish I could. My guess is that she moved.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Just happened, I don’t know why, just went along with it

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

How intoxicated was your partner? I don’t know

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? Somewhat

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 don’t think that I ever told anyone this story.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I learned that I like cock and it was a new experience for me.

What was the WORST thing about this hookup? It didn’t last longer.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No.

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? I think that people should be able to have sex with whomever they want as long as it is done in a legal and consenting way. You don’t think twice before you go into a restaurant to buy a good meal even if your partner/wife is the best cook.

What do you think about the Casual Sex Project? I love to read the stories.

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