by CaptainSad


Gender: Male
Age: 59
Race/ethnicity: White
Current location: Unknown
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: CEO
Relationship status: Married
Religious affiliation: Christian
How religious are you? A little
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Show me a vagina and I’ll fuck it.
How many sexual partners have you had in your life (including oral sex)? 27
How many hookup stories have you here posted before? None

Horny Co-Worker

How long ago did this hookup happen? 40 years

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…)? Two Nighter

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? She was a little short and a good figure. She was my a co-worker at the time.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It started at the end of my shift one night. I was 19 as she was 34. She was divorced and had 3 boys. She asked me to come over to her house and talk.

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? It all started when she invited me over to her place after work. I was sitting on the couch while she put her 3 boys to bed. It took about a half hour. She came back to the living room in a light colored robe. You could see her hard nipples poking out of it. And I saw a bare pussy. Being 19 it was hard to hide my 8 inch erection. She just kept staring at my crotch. We were talking and of course sex talk came up. She was telling me she hadn’t had any in 6 months. I told her I masturbated more then actually fucked someone. I could tell she wanted me. She all of a sudden pushed me back on the couch and gave me one long kiss. By then my erection was at full staff. She just grabbed it. She undid my zipper and pulled my pants down and went down on me. I nearly exploded right there. She took off her robe and mounted me. Those tits were awesome. To my dismay I came really quick. Wasn’t even a minute. She said to me don’t worry we have all night. She got up and got a towel to clean ourselves off. She was still horny and decided to suck me off. I got hard in about 10 minutes. She was just bobbing up and down. And I had to tell her to stop. She kept going and another load went into her mouth. I was in heaven. I had to collect my thoughts. So I decided to return the favor and went taco diving. She tasted great. She must have cum 4 or 5 times in a half hour. She was so loud she woke up one of her boys. We calmed down and we’re talking about our lives and past sexual escapades. For some reason she put her hand on my semi stiff and got me hard again. She was impressed I could get another one. I just laid her back on the couch and entered her again. This time it lasted a good 40 minutes before I emptied again. She went nuts. We both fell asleep on the couch. It must have been 2 hours and I felt wet lips around my cock. I played like I was asleep. It was hard not to move. It got hard again and she was going to town on it. She started using her hand. I could tell she was rubbing her pussy as she was giving me a hand job. Every once in awhile she would rub her wetness on my cock. It seemed like forever and I shot another load all over her face and hair. Of course at that time I was fully awake . All I could say was thank you as my cum was running down her cheeks. She licked every drop. She made me breakfast for being so nice to her through the night. I stayed while she got her kids off to school. After the kids were off she took off the robe and asked me for one more time. I said I don’t think I have anything left. She said let me find out. She got down on her knees and put my cock in her mouth and coaxed it to becoming hard. All I remember was the pain in my shaft for being up all night. I can tell you this one was the best fuck of the night/day or whatever you want to call it. It lasted so long that she came for the first time in her life when she was being fucked. As I felt her cum I exploded with what I thought was just air. When I got off of her and looked down at her a big gush of semen came out of her pussy. All I said was WOW. I went back the next night and almost repeated the night before. Just couldn’t do it. We saw each from time to until she moved. That was what I call a true MILF (Mom I’d Like to Fuck).

Did you have an orgasm? Did your partner(s)? Yes we did. 5 for me and lost count for her.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history: Just plain bareback for me. She used an IUD.

What were your REASONS for having this hookup? Getting my rocks off. Better than masturbation.

Were alcohol or drugs involved? If so, how much? No..

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? I felt great. My ball sack was happy.

To whom did you talk about the hookup? How did they react? Just her.

Was this a consensual and/or wanted experience for you? For your partner? Yes. We both wanted and needed it.

Do you regret this hookup? If so, why? Hell no.

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? The best was cumming 5 times that night. The worst I seemed to run out of sperm.

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

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

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