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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? FL
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Consultant
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Agnostic
How religious are you? Somewhat
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? 6

Shalamar Reunion

How long ago did this hookup happen? 6-7 months ago

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 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 a former high school classmate I hadn’t seen in about 28 years. He was my high school boyfriend for a spell (nothing sexual, just some kissing). I was in foster care, so I was forced to transfer high schools to be nearer my group home. My parents were crazy and strict, so I wasn’t able to date or have a normal childhood (which I think has led to my sex positive attitudes about casual sex).

We met at a class gathering at one of the classmates house. I’ll call him Shalamar, because he looked like the lead singer of the R&B group from back in the day. I didn’t know he was coming, and he was friends with one of the classmates present that had been at the first event (K.). They were best friends. We all arrived and were unpacking our cars for the cookout/crab boil we had planned. The Friend came to my car and gave me a hug and told me that there was someone in his car that knew me, could I guess who it was. At this point, it has been almost 30 years so I just said no. The guy was just sitting in the car, so we both began walking over to the car and as I got almost to the passenger side car door he got out. It took me about 3 seconds to figure out who he was because he had Vitiligo, so he was not easily recognizable. But when he started talking, I immediately recognized who he was. He was still handsome, black (very light skinned), wavy thick hair, about 5’11, a neat goatee. He had on his pro football gear (we liked the same team). We hugged briefly as I was in he middle of unpacking my car. He complained that I gave him a church lady hug. We all laughed I continued to unpack. We all sat down in the same room and reminisced about our childhood. He talked about all the things he recalled about me in middle and high school…..which was very interesting. He remembered some project I presented in middle school which amazed me because I had forgotten about it until he recalled it. We really liked each other during middle and high school, but because of my disruptive home life and strict parents, I just wasn’t able to be a real girlfriend. He told the group that I should have been his childrens’ mother and I should have been his wife. It was nice to hear that and I was flattered. Because I was prepping food, I really didn’t have a chance to socialize as much as I would have liked, but Shalamar kept coming in and checking on me, asking me if I was alright which was very nice. Others hadn’t seen him in years, so he was a hit and he was working the room. He was trying to make sure he talked to everyone there. Before the hookup, I was happy to see him, glad he had come to the event, but a hookup was not even a thought for either of us.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I instigated. As the night went on and we all were in the same room trash talking like we always do, we started talking about sex and my requirements in a man. A big penis, good penis was what we were discussing and they all cracked up on my visual descriptions. Shalamar says I have been saying the same thing since school and that he found it hilarious that I was still saying it. I told him that I meant it now, and everyone laughed. He had been really working the room hard, saying things to some of the ladies at the event trying to see if anyone was open to offering him an invite. He didn’t live in town, his kids were with his Mom and from my understanding, he was raising them as a single dad, which I admired. All throughout the night, he kept asking me if I needed or wanted anything to eat or drink, which I also admired. I had some shots of moonshine, and was feeling like I needed to get laid. He had been indirect all night, he knew I was married and I didn’t do anything out of character in front of anyone to make them think I had cheating prospects.

As the night closed and everyone started to leave, he and his friend had packed up their things. I was cleaning up in the kitchen of our mutual friend who’d gotten drunk and was passed out in his bedroom. J, the friend that brought Shalamar to the event came into give me a hug and said he was getting ready to leave. I told him pretty bluntly that I was gonna fuck Shalamar tonight, so how could he leave me without saying goodbye. J says immediately, “By all means don’t let me stop a man from getting some pussy,” then went outside to relay what I said. Shalamar came in and was extremely excited about the possibility of hooking up with his high school crush (or someone at the party for that matter lol). I invited him to my hotel, and told him what time I’d arrive. He told me he needed to get his kids situated at his Mom’s and then he would come back out to meet me. He asked if he needed to bring anything and I said no.

He told me to call him when I arrived at my room, and I did just that. I hoped in the shower, shaved my pussy and legs, put on some shorts and a t-shirt (no bra or panties), and got in the bed waiting for him to arrive. He called, I gave him the room number and he came in. We hugged each other, and sat down on the sofa in the room.

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? Once we sat down, we reminisced for about 2 hours. He didn’t realize that the reason that I had left was because I was foster care and was really upset about it. He said his mom was a foster parent and had he known he would have asked her to attempt to get me (although I probably would be pregnant with bunches of kids lol I’m sure). We talked about our kids (he has young, I have adult), and our relationships (he’s partnered with the kids’ mother who is not parenting appropriately but they still share a home, while I am married). I could tell he was nervous. He kept talking and finally I said, “You don’t have to keep talking, we are both adults and this is not what we came here for really.” I think he was shocked at my forwardness (which is really an issue for many black men). He asked if he could shower, and I approved. He called me into the bathroom to see his body. He was very sexy even with the Vitiligo, I was turned on, but suddenly a little nervous. We went to the bedroom, and dug out my condoms and I turned down most of the lights. He pulled out his condoms as well. He walked behind me, started kissing my neck passionately, and coddling my breast .I just melted. He seemed to know exactly what my mind, body, soul, and spirit needed. He was so passionate, so caring, so attentive. I sucked his dick on and off all throughout the night. I’d ride him and hop off and suck him, then he’d put another condom on and we’d go at it like rabbits again. I was so wet, he sucked on my tits and fingered me like a professional. He twirled my body around that bed like he owned it and I enjoyed every moment of it.

We made love, and I came so many times. He ate my pussy like I’ve never been eaten out before. He passionately fucked me for hours in all kinds of positions. We whispered in each other’s ears, and we just instantly connected. It was amazing…just perfect. He gave me everything I missed at home. We fucked until about 5am in the morning. He said it had been years since he’d had sex like that. He didn’t get to come because of the condom. I didn’t offer to have him take it off either. For whatever reason, we didn’t decide to trust each other (understandably). His dick eventually died/lost life, and we laid in the bed finally dropping off to sleep a bit. The sun was rising..and it was time for him to do the walk of shame. I was so tired and weak my legs were trembling as I got up to walk him to the door. I was elated that I had such a good lay, sad to see him leave. I got up naked, gave him a hug, walked him to the hotel door and said goodbye. The last thing I said to him was to stay in touch. We had each other’s phone numbers.

He was an extremely good lover. One of the best I’ve ever had. He was my classmate, my former boyfriend which made it so special. We didn’t talk about what happens after that night. I thought about him a lot. I think he was very sad internally because of his personal appearance, and happy that I saw beyond it. I could tell he wasn’t happy in his personal life either. He walked out of the door with a disposition that just didn’t set well with me. It ended with him walking away. I haven’t seen him since.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? No

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? After the hookup, we went our separate ways. I felt very good the next day, and I still do. My expectations were that it would have sparked something. A connection or at least a connection. But I understand I am married and lived 2 states away so I’m sure that was a huge issue. Also, the fact that I was married was also likely too messy for him. I believed that he had too many issues at home, and he also has very young kids. I wonder though if my sex-positive forwardness was too much for him. I would have liked to continue with him, but he hasn’t made ANY effort to initiate any type of connection/relationship. I reached out to him once and called about 2 weeks after our hot sex session. He was kind of short, not rude, but didn’t appear to have any interest in establishing a conversation for whatever personal reason(s). I decided that I would not attempt to contact anymore and chalked it up to a one night stand. I would never sleep with him again. He doesn’t have good pussy etiquette. If it’s good, you should respect it. You never know when you may have to go back to that well! Still glad that I did him though. No regrets.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Thought it was an important experience to have, I was feeling lonely, Making new friends, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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 (classmate) that was there and my bestie. They both reacted positively. A bit concerned that there was no connection afterwards, which was so unlike him. They encouraged me to call him after a few weeks, but I didn’t. We all are perplexed, but you just never know what is going on through people’s minds. We can only control our own actions we all agreed upon.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The sex. The intimacy. The passion. The reunion with a high school sweetheart. The fact that we were able to talk prior to sexing and were comfortable enough to connect.

What was the WORST thing about this hookup? There was no connection afterwards. It didn’t lead to a longer more intense fling. The lack of respect shown after we slept together. It wasn’t expected. Kind of shook me emotionally. Such is life. Some men are assholes. Some are poor communicators. Some are selfish. Not my monkeys, not my circus.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No. I like causal sex. I just wish we could be more transparent about it.

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 was good. Wished it lasted longer. Looks are important for us at times, and looks can be deceiving. A not so attractive person outwardly does not equate to a less than satisfactory sexual 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? I think we aren’t allowed to explore our sexuality enough. I have read some interesting stories that have truly opened my mind and wanna try new things. I am on an emotional roller coaster because there are so many things that people enjoy I never knew about. Some of it is shocking, some of it is interesting. I find myself having to battle with my own mind about my teachings. I’ve decided that I’d like to be apart of as many varied experiences (safely) before I die. I wish society would share truths about sexuality, and all the “abnormal” or “non-traditional” types of sex options we could have available to us. It should be enjoyed and no controlled.

What do you think about the Casual Sex Project? I love it. I’ve learned so much about people, preferences, desires, and how many people have to hide their sexuality and personal sexual preferences. This project is going to lead me living the sex life to the fullest. I enjoy and I read it every day.

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