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What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Palm Springs
Highest education received: College degree (eg., BA, BS)
What’s your occupation? RN
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? over 60
How many hookup stories have you here posted before? over 10

A Sick Co-Worker

How long ago did this hookup happen? about 10 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 1 to 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’ll call her Mary. I was 42, and Mary was 31 at the time. I had met Mary at work a couple of years before and we had worked off and on together. There was nothing special about Mary. She was attractive with medium length blonde hair, a nice ass, and a small waist. She was always pleasant with a smile and a nice word to say about people

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had heard that Mary was in the hospital and was about to be discharged home. I knew she had separated from her husband a few months before. I stopped by her room on my lunch break to see how she was. She seemed depressed and said she was not looking forward to going home to her house alone. I asked her if she would like me to stop by after work to check on her, and she said she would like that. I got to her house later and knocked on the door. She opened the door, and she was dressed in a blue robe. She let me in, got me a soda, and we sat on the couch with the tv going. I asked if she was okay and she began crying.

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? I pulled her over to me and she rested her head on my chest. I tried to comfort her as best as I could and pulled her in close to me. She looked up at me and I kissed her. She moved even closer to me and began kissing my neck, her hand went to my thigh and began working up towards my crotch. I pulled her in so that her chest was against mine, and at that time I realized that I had never appreciated how large her breasts were. I reached inside of her robe and took one of her breasts into my hand. I later found out that she was a 32DD. She rubbed my now hard cock with her hand through my pants, I leaned over and took her nipple into my mouth and sucked her hard nipple into my mouth. She stood up, took me by the hand, and led me into her bedroom. She pulled the covers back and dropped her robe to show me that she had nothing on underneath. She laid down on the bed as I quickly got out of my clothes.

I got in bed with her and laid on top of her, her huge breasts against my chest. I kissed her and we used a lot of tongue. She grabbed my ass and pulled my hard cock that was laying between her legs up tight against her cunt lips. I rolled her onto her side and began sucking her breasts as my hand wandered down her body to her hairy cunt. I separated her cunt lips with my fingers and slid my finger into her very wet pussy. She grabbed my cock and was stroking me as I was sucking her tits and fingering her pussy. She pulled away from me and pushed me down on my back. She began sucking my cock as she massaged my balls with her hand. She went down to my balls and began sucking my balls into her mouth as she fingered my asshole. She slid a finger into me slowly and then began massaging my prostate as she sucked my cock. It didn’t take long and I was shooting rope after rope of my cum into her mouth. She withdrew her finger from my ass and sucked my cock until it was limp.

I rolled over on to her and began eating her sweet tasting hairy pussy. I did my ABC’s on her and flicked her clit with my tongue. I slid my fingers into her very tight pussy and stroked her g spot. I felt and heard her cum. I did not let up, I kept licking until she had 3 orgasms as she was coming down from her last one I spread her legs, placed her ankles on my shoulders and began to work my throbbing cock into her tight wet pussy. I took a while, but I finally got balls deep into her. I worked up a rhythm and soon had my balls slapping against her ass. I kept getting close to cumming, but kept holding back. Her pussy felt so good and her breasts were so terrific for sucking on, that I didn’t want it to end yet. I finally got to a point where I had to cum. I told her that I was going to cum and asked her where she wanted it. She told me to cum inside of her. About that time I started shooting my load into her tight pussy. I kept thrusting into her until my dick softened to the point that I couldnt penetrate her pussy any more. I lay on top of her and sucked her breasts as I went soft. I rolled off of her and she sucked my cock into her mouth and sucked me clean.

We laid there and talked and kissed and caressed each others’ bodies for a while. I would suck on her nipples and she would tell me to suck and pull harder on them. She had an orgasm while I sucked her tits. She sucked me off again and I came in her mouth again. Maybe an hour after this, we started getting into pleasuring each other again. She straddled me and began working my cock in and out of her, she would grind on my cock and I would pinch her nipples and feel her cum on my cock. I finally rolled her over one last time and pounded her pussy until I unloaded in her again.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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 met up many more times after this. She would stay the night at my place or me at hers, always fucking until we are exhausted. I have never gotten over how tight her pussy is or how tremendous her tits are. After several years of meeting as fwb, she moved away. We still stay in touch, and maybe some day I’ll be in her area and we can hook up again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have, Making new friends, Just happened, I don’t know why, just went along with it, It was easy / convenient

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? No one

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? Some fantastic sex with a very sexy lady.

What was the WORST thing about this hookup? It ended.

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

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

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