The Office



What’s your gender? Man
How old are you? 54
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? America
Highest education received: Some college (not currently in college)
What’s your occupation? Disabled
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? When I was younger I had sexual experiences with both women and men, but I prefer women.
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 0

The Office

How long ago did this hookup happen? 3

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

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For 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? She is very small, very dark complexion, medium-sized breasts with hard chocolate nipples, nice round firm ass and small waist, black curly hair, dark brown eyes and soft kind of plump lips. I had been seeing her for about three years as my Doctor before this happened. We had never done anything at all except that she had rubbed her tits in my face a few times while she was listing to my lungs. I had had sexual thoughts about her since I had started going to her, she would wear tight pants, and every once in a while she had a low cut top on that showed her tits off nicely.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It happened at a doctor’s visit that I had for a full checkup. When I had first started going to her, I had a lot of problems. One of which was that I was no longer producing Testosterone and had to be put on several blood pressure medications that messed with my erections. So, she put me on Testosterone and Viagra, which was working very well. My cock seemed to get back to its big self and hard as a rock. I had a late appointment around 4:30, I was not thinking when my wife and I had sex about an hour before going to my appointment. By the time I was seeing the doctor my Viagra was still working. I started to get a bit nervous thinking I would get a massive hard-on right in front of her. So, I am sitting in my room in my paper shorts and shirt with a semi going on. It was not long before she came in and said the usual things, “How have you been? What’s going on?” I gave my regular answers, “Fine how are you? I have been doing pretty well.” Then I noticed that her dark nipples are sticking out through this thin white blouse, it looked like she had no bra on by the way they just stood straight out, but she did, it was a black lacy bra that pushed her perky breast up together out of the two undone buttons at the top of her blouse. That was it, I was at full mast and trying to cover up my tent. She came over and put her hand on my chest and listened to my lungs through my back. Then she switched and listened to my heart with her Tits right in my face. Oh Geez, what was she trying to do, make me shoot a load right then? I kept my hands over my crotch trying to push my cock down. Then she told me, here comes the part you don’t like, then she shocked me and said, “Well you never know, maybe you do.” I did not know what to say, then she said, “Okay stand up, bend over the table, and pull your shorts down.” Well, that was it, no hiding it now. When I stood up my cock was sticking straight out which she noticed right away, she got a Cheshire Cat grin and said, “Well, maybe you do like it.” I said, “No that’s not it.” I thought I would put her on the spot as she did to me, so I said, “It was your sexy bra and your, well, you know, Your nipples.” My mouth went dry and I hoped I did not make her mad. She said, “Oh thank you, nobody has ever been that bold before, but thanks.” Then she said, “Pull your pants down.” The sweat started to pour, I did, and my cock was right at her stomach because she was short, she was looking at my cock and said turn around, I felt the cold K-Y go on my butt hole and then the finger as she pushed it in really slow, she asked if that hurt and if I was okay? No, it did not hurt. She felt around for a second then she pushed her finger in a little deeper and moved it around just a little and asked if it was ok. All I could say was yes, then she said, “Well, you have a swollen Prostate.” Then what happened shocked me even more, my cock was as hard as it could get, with every vein pumped full of blood and throbbing.

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 started to pull her finger out of my ass then she pushed it back in and started finger fucking my ass slowly and gently, I had to spread my legs further apart, and my back arched a little. She said, “How does that feel? Do you like that?” I said, “Yeah, it feels good.” Then, she started rubbing my scrotum from the inside. Then, she reached around and grabbed my cock and started stroking it with a loose grip slowly letting her hand glide up and down my rock hard shaft. I started to moan and tell her how damn good that felt, but then she stopped everything and told me to turn around, she pulled her glove off, washed her hands, and came back and sat down on her little roll around stool. My cock was right in her face, she cupped my balls and told me to turn my head and cough, she said nothing wrong there, I was breathing heavy and so fucking turned on, she just kept massaging my balls and then started pulling on them and grabbed my cock and started stroking it again. She said, “You have a nice big cock, and the meds seem to be working great.” I said, “Oh yes they are,” I could not hold back any longer and said, you are so damn sexy, and I have always wanted you. About that time I felt warm wetness around the head of my cock as she started sucking and licking the head of my cock. I said “Oh god, oh god that feels so good,” her tongue swirling around on my cock as she sucked it. I grabbed her hair and pulled her down onto my cock and pushed it a little deeper into her mouth. She gulped and pulled back I reached down and raised her up and started kissing her, my cock sticking between her legs, I pulled her top off and then her bra, unbuttoned her pants and pushed them down, she did not have any panties on so her pussy was out there naked. I reached down to grab her pussy and started fingering her. I parted her soaked lips and pushed two fingers inside her pushing them in and out. She moaned and started grinding her hips to my motion. Then I started sucking on her hard black nipples, I found her G-Spot and started massing it. It was not long until she was going off, humping my hand and pushing my face onto her nipples. Just felling her wet hot pussy in my hand and her hard nipples in my mouth almost got me off. My cock was so hard after she came and her body was still twitching. I picked her up and sat her on the table. My hands started massaging her from her breast to her feet, sliding all over her body, she felt so good. My mouth went right for her dripping pussy, licking and sucking her lips, then running my tongue around her clit, finally licking her clit up and down and side to side, she was cumming again and again. I raised up and put the head of my cock right in her pussy. Then she said, “Fuck me hard with that big cock.” I started pushing it in slowly as her back arched and she moaned out very loud, I just kept working it in until my balls hit her ass. Just the look of my pale white balls and cock on her dark skin was exciting and very sensual. It did not take long for me to cum as I pumped her cunt hard and fast. I pulled out shooting my white cum all over her dark pussy, I shot streams of cum hitting her pussy and stomach, and some went on her tits, I fell over on her and kissed her, then we both got up, cleaned off, and got dressed. I told her that I was so turned on that I never thought about someone coming in on us, she said that we were the only people there, everyone else went home. Then we went out, and I left.

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? I left and felt good, she is still my Doctor, and we have never talked about what happened. If it happens again, great!

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, attraction to partner(s)

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? I didn’t tell anyone

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? the sex and the excitement

What was the WORST thing about this hookup? nothing

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? Fairly positive

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

Anything else you want to add about this hookup? just the fact that sometimes fantasy comes true

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 people should be very picky.

What do you think about the Casual Sex Project? It is a good thing and can be an excellent outlet.

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