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What’s your gender? Woman
How old are you? 42
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? Freelancer
What’s your current relationship status? Separated/in a new relationship
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? 7-8

She Messed Up My Whole Life!

How long ago did this hookup happen? Jan 2017

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For less than a month

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 was beautiful. Tall (6ft), soft spoken, beautiful brown skin, feminine. I only knew her for a few weeks. We chatted online, had a lot in common, could deal with each others’ situations (we both were married, she married for 25 years), and decided to embark on a safe FWB relationship. I wanted to explore being with a woman and this was a discreet way for me to do so. I met her on a site (shybi.com), a site for women questioning their sexual identities. I was married, in a bad marriage (11 years) nowhere slow. I always had a desire to be with a woman, and after a bad holiday season, I decided to explore my options for a female friends with benefits that would be less suspicious than having a male partner. I really liked her initially. I just expected it to be sex and nothing more. Boy was I wrong.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hookup began at a pre-determined location. Planning was definitely involved. We met at an upscale resort, all arranged by her. I brought wine. From the moment I valeted my car, she took care of me. She met me outside and greeted me with a big hug. We walked to the elevator, where we were alone and I got my first real kiss by a woman, a mature woman. It was awesome. We entered the room, and the patio door was open. The resort was on the beach and our room had an ocean view. She suggested the encounter. She was very aggressive, which was refreshing and sexy to me.

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 had a sex toy so that I could ensure I got an orgasm as I have a long drive. We had a beautiful lunch at the resort and had a long talk (2 hours). I was nervous. It was my first time. She was very relaxed, with a little more experience under her belt than I did. We went back to our room went to the balcony and began kissing in the public which was very freeing. Sexy. I didn’t care who saw us. As things got hot and heavy, we paused to open the wine, put on some mood music, had a little then started going at it again. We rubbed and touched each other, explored our bodies just being revealed for the first time.

We stripped each other down and made our way to the bed where our bodies touched. Breast on breast, taking turns for each of us being on top of each other. She went down on me first, from my neck to my breast, to my pussy. I was so wet. She ate me for a long time, but I wasn’t able to cum. I flipped her over and at her pussy. I enjoyed her reaction. Her smell, how she tasted, and how wet she was as a result of her attraction to me. I enjoyed licking her breast, her hips, every inch of her body. I had a sex toy, so I decided to pull it out and our saving grace for orgasms on that day. We both used the vibrators to finally cum and collapsed in pure pleasure and satisfaction. We hugged and kissed and thanked each other for the wonderful experience.

She was a great lover, she was a patient partner. She changed my life. We talked about being happy to find someone sane, and willing to accept the fact that we were married, yet not putting pressure on the other to change their status. We talked about lots of things for hours. We lay naked and chatted, napped, and had sex again until it was time for me to leave (no orgasm) lots of intimacy. I had a long drive home (2 hours)

How sexually satisfying was this hookup? Very

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? After the hookup…..I was happy. I felt like I had experienced something I always wanted to experience. It felt natural and normal for me. The next day, I had no regrets for the relationship, only regrets that I did not explore my bisexuality earlier in life. I wanted to be with her long-term. Now, I love her. It’s been a very fast, intense relationship. Being with a woman is far different than being with a man, in a good way. We had searched for a long time to find the right partner, and we were both happy we were able to compliment each other in and out of bed. I am hoping for a long-term spouse. Eventually a partner/spouse even maybe. All I know is I want to be with her every day for the second half of my life. She’s good to me and good for me.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Sterilization, Discussed STI testing history, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, To feel better about myself, To feel more desirable, I was feeling lonely, Revenge / Getting even

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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 best friend. She flipped. Questioned my sexuality, and my reasoning. It was a lot of talking but eventually, she understood.

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? I met a new lover. We left our spouses and are working (slowly) on a long-term relationship. It’s complicated when you’ve lived a heterosexual life for over 40 years.

What was the WORST thing about this hookup? I fell in love. My life changed. I have to maneuver the landmines of disclosing to the wrong people. I am not able to freely love a person that has so much love for me without ridicule and religious bias. We can’t tell our families.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I love casual sex. I think you don’t know what you like/dislike without exploring your sexuality. Sex is good.

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

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

Anything else you want to add about this hookup? I have decided that I love being with a woman more than being with a man. I love how women connect emotionally and communicate openly. We decided to take it slow, maintain a monogamous long-distance relationship, and eventually be in a more committed relationship. Everything has happened so fast. From Jan to now…it’s been a whirlwind relationship. I feel complete.

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? Casual sex taught me a lot. I think it’s positive. It’s a natural human activity, and religion and prudes try to Sheppard over our vagina’s and penises. I think grown consenting adults should be able to do a lot without the confines of religion. I would like to see more real life sex education for teens and adults, and less government and media bias/intrusion into our bedrooms, cars, and sex lives.

What do you think about the Casual Sex Project? I love it.

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

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