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What’s your gender? Woman
How old are you? 44
What’s your race/ethnicity? Black
What continent do you live on? North America
What country and/or city do you live in? Florida
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Writer/Consultant
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? sneaky pete freak
How many sexual partners have you had in your life (including oral sex)? 40+
How many hookup stories have you here posted before? 5

The Appreciative Short Cock

How long ago did this hookup happen? 2 years ago

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

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than 6 months

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? J was a married, older gentleman (Caucasian), mid 50’s. Gray goatee and hair, receding hair line, thin top. Nice looking, distinguished. A little on the heavy side, but always dressed very nice. I had known him for a few months. We met on Ashley Madison pre-the hack). I was just out of a LTR with a partner (another story for another day), and we met. He was professional, well-connected in politics and other high-profile endeavors so discretion was of the utmost importance. Claimed he and his wife did not have sex or sleep in the same bedroom (have no idea how people can do that). We met frequently out for lunch and/or coffee to build our relationship. He was really nice, and gentlemanly. I felt quite comfortable with him and was attracted to him in a sapiosexual type of way. He is the only man that I’ve ever met in my life that could touch you me any place on my body and made me wet. Not even sexually, just having a conversation and he would rub the inside of my wrist, or we would be taking a road trip and he would rub my thigh and it would make the hair raise on my arms. He was indeed intimate and experienced in every sense of the word.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Well after a few weeks of meeting talking and be intellectually stimulated, he was ready to have his first experience with an African-American woman. I really liked him so I was ready. We had planned to hookup for sex a few other times, but something always came up (on his end) which was frustrating. This one time the stars aligned and we set off to consummate the LTR. Much planning was involved. He got a hotel in another county, we met, I got into his car and we drove to the meeting place. He was always so prompt. He was retired, but time management was his thing. We both instigated it.

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? We both were a little nervous, he more so than myself. He was going to be the second Caucasian man I’d ever been with sexually so I wasn’t sure what to expect. He checked in, came out to get me and we went into the room. The room had a couch so we turned on the TV and sat really close to each other. He did that touch thing that he did and my pussy started running like the Mississippi River. We began kissing, which was nothing spectacular. He kissed like a bird, barely opening his mouth. I didn’t like the way he kissed but I liked him and he does so many other things that were important to me that I settled on not having that. He moved his way down to my breast and took off my dress and removed my bra. I stood up and sat on his lap so he can enjoy that triple D buffet. He lifted me up and inserted his fingers inside of my pussy and I just threw my head back in ecstasy.

He had had a back surgery so he was getting a little stiff. I suggested we move to the bed. I had pussy juice all over his pants. I got up from sitting on his lap and he needed to use the rest room. I used that time to scurry to the bed and pose for him when he came out. He took a shower and came out nude. To say I was disappointed to say the least was an understatement. He penis (not hard) was as long as my pinky finger. Should have figured… can’t have everything in one package I suppose. He told me he wanted to eat my pussy, so I hashed my legs up and let him have at it. He was marvelous at eating pussy, breast play at the same time. He pulled me to the edge of the bed, got on his knees and blessed my pussy with his mouth. After about 10 minutes I came. I laid back on the bed… and I was trying to figure out what am I going to do to satisfy him. I knew I wasn’t going to be satisfied AT ALL with his little short cock.

I climbed on top of him, turned my pussy to his face and we did 69. He was so happy he just moaned in delight. It was nothing to it. He had been so nice to me prior to sex, I felt like I owed him something special. After about 10-15 minutes he told me he wanted to me climb on top and fuck him. I was thinking to myself “fuck what” like there is nothing here. Besides he had a huge belly that I had lift to get to the cock. I did my sidepiece duties and pushed his belly up, lifted the short cock and inserted into my pussy. It felt like I just had the tip of a penis inside of me. I couldn’t move because it would come out, so I placed his hands on my breasts, and pressed my pussy tightly onto his cock so that it wouldn’t come out and rode it like a champ all awhile looking him directly into his eyes as if he was the love of my life. He came in about 4 minutes, and he came so hard. I could tell it had been a very long time since he’d been fucked in that manner. Afterwards, I fell off next to him and we cuddled. He was very happy, saying that I fucked him intensely and I made him feel like I really cared. It made me feel sad for him, but happy that I was mature enough in that moment to understand that not all men are well-endowed and how they can feel unappreciated because of this. We cuddled for about another hour, took showers, regrouped and headed back to our county. I really liked and respected him. We continued to see each other, but we didn’t ever get the chance to have full-intercourse anymore. I would say for the tools and skills he had he was a good lover. It ended when he dropped me back off at my car, we kissed and he left. We texted and emailed each other frequently after that day.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? Afterwards, I really wasn’t interested in having sex with him anymore as I was the interested in the companionship. The next day I still liked him a lot. We continued our LTR with more fondling, kissing, lunches/chats. He ended up having a car wreck and needed to have another back surgery which put him out of commission for a very long time. He told me he couldn’t do much for me (in any way shape or form) and we broke it off. He also had other health issues (had had a heart attack earlier), which prevented him from being intimate so I think he ended up having self-esteem issues. We lost touch. I think he is nice still today, and I remember how well we connected on so many levels.

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

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have, I was feeling lonely, Making new friends

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? My friend in TX who is a therapist and my best friend. My therapist friend thought it was cool, but figured since the primary idea of the hook up (for me) was for sex I would not be interested in him very long. She wished she could date him (she’s single) because the companionship was more important to her than the sex. She encouraged me to make a decision about my marriage because eventually it was going to be an issue. I did leave (but I came back). My best friend just dies laughing because I have all of these crazy hookup stories.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? That I was able to connect with J, meet someone intelligent and interesting. I made him feel cared for and sexy. I learned that there are men out here who are really deep, and they know how to stimulate the mind in a manner that is very similar to a sexual relationship. I learned that all White guys aren’t the same. All guys period aren’t the same. I also learned that there are many White men desiring to be with African American women and other women outside of their culture, but it does seem that older men who have less to lose are more apt to the idea. He really taught me to open my eyes and my mind to relationships and the possibilities, and to not be loyal to one race or ethnic group becacuse society has issues regarding race. Sometimes we are forced to have personal preferences and loyalties for reasons none other than bias/racism. Age, sex, penis size, color……. shit gets really complicated.

What was the WORST thing about this hookup? His penis was small. He was self-conscious of it. If he had a big penis the event would have been absolutely beautiful.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I think casual sex amongst older, married individuals is a very taboo and undiscussed topic. I enjoy all sex, casual and monogamous. I question my sexuality more, and I’m leaning to not being in any more long-term relationships, especially as a middle aged person. I meet so many unhappy men who are forced to dark corners to find and have sex because spouses believe it’s not longer important any more. Furthermore, many people get older and desire to try things as they feel they have lived their lives for and through others and are ready to explore sex for themselves in a way that pleasurable to the individual in need of self-exploration. I plan to continue my escapades, my sexuality bothers no one. It’s no one’s business. I am responsible for my own pleasure and happiness.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? We continued on with connecting on and off for about a year. J’s health continued to go down, and he had several mini-strokes. I tried to keep in touch, but he stopped responding. I’m not sure what happened to him. He’s one man that I would have figured out a way to please and be pleased by because he was such a wonderful man in every sense of the word that’s meaningful to me.

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 have had a love hate relationship with casual sex. The NSA is ok and approrpiate for me at certain times of my life, but then I begin to crave a monogamous relationship only to eventually be let down by the decrease in sex and interest (by my partner or myself if the sex gets horrible) as the relationship progresses. Sex is very important to me. I just find people change, and we ought not to be bound be so many rules as it pertains to sex, especially women. I want to be able to be satisfied, and sometimes one person in a lifetime isn’t enough if you’re highly sexual or understand your own needs and desires and an individual.

What do you think about the Casual Sex Project? I love it. I have had so many situations that I never told anyone about because I was embarrassed (they happened when I was younger), but I have read so many stories very similar to mines. I learn about the unique needs of individuals especially men. I’m very interested in the stories of older individuals, and the stories about married men sleeping with transexuals or having non-traditional same sex connections as an experiment or because they are living a double life. Kind of scares me, but I am also forced to address the reason why these men partake in these types of relationships. It’s because of all these rules society imposes. Sometimes people surpress their true sexual desires because of fear of not being accepted. I don’t think any of us should have to live like this. At least there is a way for us to connect in our own different ways to express how different and vast our sexual needs/desires are. Shit happens sometimes, and sometimes we are living a lie to please others… not ourselves. We must live, before we die.

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

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