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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
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
How many sexual partners have you had in your life (including oral sex)? 40+
How many hookup stories have you here posted before? 3

The Strappin’ Young Buck

How long ago did this hookup happen? 2 years ago

What was your relationship status at the time? Engaged/Married (monogamous, but separated from husband)

How would you best classify this hookup? Short fling

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? He was handsome, a former college football player (I call him Strappin Young Buck). He was very strong, muscular, dark-skinned, and he was “my type.” He was young (26) and was a former childhood friend of my son. I used to work with his mother (we are the same age) many years ago, and we are passing acquaintances with friends in the same social circle. I felt like he was just a kid, one of my sons before the hookup.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was separated from my husband and had relocated back to my old town temporarily for work. I was hanging with some of my friends that I had not seen in years watching football and trash talking. These were primarily guys. I can’t remember if he was there or if he arrived later, but he was quiet, as he doesn’t talk much. He’s nearly 15-20 years younger than many of guys in my old crew. They were talking about sex and their penis sizes, what they could do for a woman (or to me) and I pulled out my tape measure on my key ring and offered to measure them. My mantra is 6 figures or 9 inches. You need to have a big dick or resources to make me forget you don’t have one. Anyway, after trash talking and basically killing all of their spirits, Strapping Young Buck walks over and says when you meet the criteria, you don’t have to talk about it…and walked off. The crowd went back into the building where the games were playing, and the Strapping Buck and I were left outside. We chatted a bit briefly, nothing sexual at all and we said our goodbyes. I was hoping he would ask me for my number or make an advance, but he didn’t. But I couldn’t get that body out of my mind. I went back to my best friends house where I was staying and told her about the strange encounter and my desire to test him. My friend shook her head and basically said she wants no parts (because of our social circle and the ugly fallout that could possibly come from it if it was ever disclosed). They all worked at the same place, which made it kind of awkward.

I instigated it. I went to my bedroom to calculate how I could make our paths cross again. He was on Facebook, so I sent him a private message. About 2 days later he responded and we chatted via private message for a few days. He offered to take me out on a date. I was excited. We went out (he picked me up), he made sure to tell me that my age didn’t matter and that he was private and wouldn’t disclose our date to anyone, even though we were out in the public. We went to a late movie, which was cool, no one was really out. He told me that he had recently seen my son who had graduated from college (which was weird) and how nice of a guy he was. The night ended, he dropped me off and attempted to kiss me. It was weird and kind of awkward and unexpected. We ended the night with plans to get together again.

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? A few days later, the old cougar invited him over for lunch while he was on his lunch break. I was working in the field so I was able to come home and prep something so we ate. I wore an easily accessible sundress with lots of skin showing. He ate lunch, then he ate me. He wasn’t a great kisser, not good at foreplay, but it was fine at that point because I only wanted his dick. He whipped it out and I took my tape measurer to measure it. Sure enough it was 9 inches! I was wet just thinking about riding on it. We were in the living room and standing so I unzipped his pants, dropped down on my knees to give him a blow job. I could tell he was enjoying it. He had on his nice little dress slacks and work shirt.

He started stripping like he was in the movies. As I sucked his thick, long, chocolate dick, he was moaning like we were all alone and enjoying it. He pulled my dress down to find nothing on underneath. Strappin Buck grabbed my boobs and sucked and squeezed them in a way that let me know he appreciates breast. He led me over to the sofa, sat down and motioned for me to sit on top of his dick. I did so enthusiastically. I was so wet. I slid down his shaft and moved up and down in the beginning slowly so he could enjoy my breast and savor the moment like I did. It was something so wrong about it, yet so right. At that moment I was only thinking about how this young kid had grown up into such a handsome, strong, sexy young man. We tried several positions before he came. The Young Buck came several times. He was very gentle, very experienced once the foreplay was out of the way. I got the feeling that he liked older women and that he had been with plenty. I’m pretty sure of it. When we were done we cleaned up, and I thanked him for being such a great lay. He made sure he left no doubts that he not only enjoyed it but also wanted more. I was a little skeptical as I did not want to get caught.

It felt really good during, and afterwards. He was respectful afterwards, but kind of immature in how an older, experienced woman desires and need to be coddled prior to intercourse sometimes. He was always interested in what I did for a career and learning how to advance in his career as well. He was a very business-minded young man. He was a very good lover. We hooked up about 4-5 more times before I decided to return home and try to work things out with my husband. Strapping Buck wanted something serious, but I wasn’t interested in him in that manner. I think he liked a woman that would care for him like a mom and that wasn’t happening. I’m pretty sure I hurt his feelings, but I couldn’t risk all the landmines of that type of relationship. Plus, he had small kids which is an absolute deal breaker for me. I’m not interested in babysitting anymore. My kids are grown, so it was never a consideration for me to be more than just a lay. He was good. Eventually, he got better with the foreplay and the next few times we had great sex. I came multiple times, had squirting orgasms during intercourse. He told me I was the wettest woman he’d ever been with. I was proud of my pussy that it could still tame strapping bucks.

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 was fine the next day. I had a glow because it had been so long since my body had that type of work out. Men my age don’t have the stamina to keep up with me and my insatiable appetite. I can deal with the young buck drama and youthfulness. It was nice that he got the picture and still wanted to continue to see each other. He wanted more, but I didn’t. There is no future, though I have seen him once or twice since I returned back home. Since we stopped engaging sexually, we don’t communicate much. We used to text, but I don’t do anything that will give him ideas about anything long-term. He’s been with other women, all of them older than him. I think they cater to him, I don’t. I think he still nice, and extremely handsome. He is still conscious of his body image, which will make him constantly attractive to suitors and me, Ms. MILF.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Thought it was an important experience to have

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 best friend. She just died laughing and hoped there was no fallout from it. She lives through me, she says. She is always supportive and I share everything with her. Eventually, they ran into each other one morning leaving her house when he stayed past the walk of shame hour. They share chuckles at work about it (they work for the same company, he’s in upper management).

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

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? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The sex was amazing. He was an amazing specimen of a man.

What was the WORST thing about this hookup? He’s so young. It was the first time I’d ever been with anyone that young and so close to my kids. I feel bad just a smidge. My kids don’t know.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No, I love casual consensual sex but it confirmed that I need to stay away from guys too young and young single guys. I don’t want to turn any young bucks out with seasoned blow jobs and exciting sexual encounters.

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

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

Anything else you want to add about this hookup? It made me realize how important foreplay is to have a good sexual experience for me. A lack of intimacy leading up to sex is a mood killer and I can’t get over it during the encounter. I have to have that even if it’s casual sex for a good encounter.

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? In general, I like it. I’m a rebel, so I’m done with caring about what society says about it. I’m sad that my friends are so prudish, even when most are divorced because their husbands cheated (multiple times). Monogamy is an unrealistic and unattainable objective. The sooner we realize it, the better. There is no happily ever after, and the number of married people dissatisfied (look at the stories posted here) really confirms it. I wish we would stop encouraging superficial things in relationship in our society and focus on addressing the core things (needs) that cause us misery, causing many of us to be cheaters. Society tells us we need to have one wife/husband, have kids, and do all these things that take away from being happy. Sex is a basic need like food, water, and shelter. For some, it is more important than others. We shouldn’t have to downplay our interest (or lack of it) just to be mated to someone we are going to eventually cheat on. It’s crazy.

What do you think about the Casual Sex Project? I love it. Can’t get enough of it. I read everyday or every other day.

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