Acting On A Crush

by Squeedy

What’s your gender? Man
How old are you? 45
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: Some college (not currently in college)
What’s your current relationship status? Engaged/Married (monogamous)
How religious are you? Very
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Exhibitionist/I want to fuck practically every woman I meet.
How many sexual partners have you had in your life (including oral sex)? Stopped counting at a little over 100.
How many hookup stories have you here posted before? 3 or 4

Acting On A Crush

How long ago did this hookup happen? Within the last week.

What was your relationship status at the time? Same as current status

How would you best classify this hookup? One-Night Stand

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? I’ve known her dad and her since I was a child. She is 15 years older than me and she works in the town we both live in. I only saw her about once a month for years. She is petite and tan, with auburn hair. She is considered a very attractive lady by most but everyone knows that she is faithful to her husband. She’s not really my type, but I always try.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She always had a smile when I would come into her office. We would usually chat and I would flirt but that was it. One day it seemed more pronounced and she caught me scoping out her ass a little bit. She said I was being bad, but the look in her eyes was different. At the time, I had some items for sale that she wanted to buy and she asked me to drop by her place in the morning. When I arrived at her house she opened the door wearing a red nylon nightshirt that came just below her waist. She had a big smile on her face and welcomed me in. My cock was getting hard as I was staring at her legs. She walked to the couch where her purse was and bent over to dig some money out and when she did I caught a slight glimpse of her pussy hair. I was still at the door and said, “damn that looks sweet!” I moved toward her and grabbed her by the waist, she turned around and we started kissing. I had very quickly pulled her top off, exposing her tits. Considering her age, she was really hot!

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 reached for my belt but stopped and started caressing my dick over my pants. I took my clothes off and she said, “oh God”. I picked her up and put her on her back on the couch and sucked her tits while I fingered her. I kissed her all over and asked her if my big dick made her pussy wet. I started eating her pussy and she came very quickly and I continued until she came again. I raised up and put my dick near her face so she could give me a blowjob but she closed her mouth. I started fondling her and sucking her tits and said, “you know I’m getting ready to fuck you, right?” I grabbed her ankles, raised her legs all the way to my shoulders and spread her legs so I could start putting my cock into her pussy. She was almost virgin tight. Her eyes were watering and she was screaming telling me to fuck her harder. I whispered to her, “I’m gonna cum in your mouth”. I pulled out and fucked her face until she had cum running down her face.

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? We laid there for about a minute and agreed that no one should ever know about it. I cleaned up, put my pants on, and left.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal

What were your motives for this hookup? Fun, pleasure, horniness

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? Somewhat

Did your partner(s) consent to this hookup? Not explicitly

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? 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 saw her just the other day and she told me jokingly, “I think your cock ruined me for other men”.

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? It has always been present in my life. Most will never admit to sexual desires they have fulfilled. I have had hookups with a few women who say they have only been with their husband. One of them was married and we hooked up multiple times. She used to send me pics and I started showing them to a friend and would tell her what he had to say about her body. Eventually, she gave him a blowjob and swallowed his cum while I fucked her.

What do you think about the Casual Sex Project? I enjoy having a forum to tell about sexual encounters.

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