Can’t Shake The Feeling



What’s your gender? Man
How old are you? 48
What’s your race/ethnicity? Hispanic / Latino/a
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? IT Exectiuve
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
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)? About 30 or so
How many hookup stories have you here posted before? None

Can’t Shake The Feeling

How long ago did this hookup happen? Affair ended about two years ago

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

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

How long did you know the person before this hookup? For 1 to 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 fairly tall (with heels), long hair, the clearest porcelain skin, not a BBW but she has a couple of extra pounds. Long legs, they used to call her flamingo because of her shape and that is how she was shaped really. You know what they say, chubby girls are always cute and she was no exception. The one thing she had was ‘sex appeal’ and that was one of the nicknames I gave her.
I met her at work, I would pass by her cubicle when I was leaving work. We worked in the same organization but in different areas. I ran IT, she was a product analyst on the business side. Our paths at work rarely crossed.
Before we hooked up, we would chat but very sporadically. Outside of me passing her desk when I would walk by, I didnt talk to her nor speak to her. I did find out that she was recently married and she did tell me she was going to Jamaica for her honeymoon. I didnt push up on her nor did I have any intention of connecting with her. Although I found her attractive, I really didnt pay much attention to her. I figured her recently being married was an indicator that she was happy and not interested in looking around (and neither was I, although my marriage was in rebuild mode, I was not seeking a lover).

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After a year, I asked her out for lunch, just to get to know her better as we had been in different meetings (not work related per se, but for an organization where I was the site leader and she joined the organization). We actually never ended up meeting for lunch and instead connected over drinks after work.
First time out, we went to a bar which was basically empty. We just started talking about each other. We have the same nationality and for the roles, we are in, there are not many people like us. I was the only Hispanic IT executive and she was the only Hispanic woman in her department. She wanted to get her MBA and I already received mine from an Ivy League institution. Ironically she wanted to get her MBA from the same school. It was natural for me to assist. That started us talking a bit more.
Before you know it, I knew all her details: unhappily married, already having an affair with someone at work (started three months after her Jamaica trip and at this point about 8 months in). Now I know she plays.
We are now sexting, talking about different escapades (threesomes, hours long sex sessions, preferences, etc.). I ask her out for drinks again but ask her if she can stay out alittle later which she agrees to. Long story short, we met at Hilton bar and I got us a room. I had her sit at the end of the bed and I told her, “You have 10 minutes, you can ask me anything you want” and I watched her nervous but excited face. She asked me if I have any FWB and I said no. After the 10 minutes were up, I asked her if she was ok which she replied, “Yes.” I then told her, “Take your clothes off.” and that was how it started.
I did tell her after our first night that I have a feeling that we have really good chemistry and energy and if this FWB doesn’t work out, I would like to remain, friends because I thought she was just a cool person. She concurred and we promised each other we will remain, friends, if things don’t work out on this level.

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 had an affair which lasted about two years. In that time, we had A LOT of sex. There were times I was having more sex with her than my wife. We both have very healthy sexual appetites. Her appetite was almost insatiable but I loved providing. We both never had a lover who can fully satisfy us. She was a voluminous lover. She wanted me to leave her sore to the point of not being able to stand, which I accomplished more often than not. We would plan meetings in other offices out of state so we could have overnights. We would have quickies in a place we called “The Forest” which was equidistant from her house and mine (old dog trail entrance). We would go to different bars and fuck in the parking lot. We never had sex without her giving me head first. I never met a woman that liked giving me head so much but she knew when she did, I would be even more aggressive when we had sex which she craved.
Over time she started to have feelings for me and vice versa. She eventually divorced her man and I helped her get an apartment on her own. This was the first time she lived by herself (she had known and was with her husband since freshman year in college, she was now 32). Our sex frequency only increased as I would go to her house before work and after work several times a week just to get our fix in. We did this for the better part of a year.
I was presenting at a conference in Florida and told her to come down so we can spend a few days alone and away and really enjoy each other continuously. All we did was eat, fuck, sleep, go to the pool, wash and repeat. We stayed in bed mostly and were naked 95% of the time. It was a great trip and proved to be the end of our relationship.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? When we flew back, I was due to fly to Europe for two weeks so our contact was going to be limited. When I get back, she was 100% different. She was acting very odd and distant. Friday’s we would hook up but she was trying to make it so that I didn’t/couldn’t come by. She started to make excuses. Two months later of this kinda distant behavior, she tells me she is pregnant with her ex-husband’s child. She tells me this on my birthday. Since the Florida trip, I had only seen her twice. I congratulate her and tell her that I am very happy for her. I drive her back to her car and we kissed one last time. That was the end…That was 2017.
She has since had a daughter, got remarried and moved to the same town I live in (but on the other side of town). We have not had much communication in the last couple of years. The first time I saw her again, she was just chatting about shallow things, nothing about our past or anything. I kept things very light and non-emotional. She asked me if I replaced her and my reply was, “I’m retired.”
I saw her maybe 1-2 additional times in 2018 but again, nothing special. Seemed more like a check in than anything else. She spoke about being a mom and her daughter and being bored. I didnt take any bait. I told her, it’s a new life, you just have to adjust.
In January 2019, she sends me a text to meet for a drink. Our communication is basically nonexistent. She would want to meet for drinks and then not reply to a text for a couple of weeks. After this type of communication, we would eventually connect and she asks me, “if I wanted to start over, how would it work?” I was surprised but also not so much. Again, not taking the bait, I told her, “When you have time, you text me and we will set something up, otherwise, I am not texting you.” I wanted to make sure she is not expecting anything from me. By this time much of my warm feelings for her have vanished and now the only me keeping them in my mind was the mind blowing sex we had. I missed that the most. I want to get that back but not at the expense of falling again. She said she will let me know.
A few weeks later, she texts me to hook up for drinks again. I ask her how much time she has and she never replied back. After a couple of additional weeks, she texts me again to hook up. I replied to her and told her I didnt expect to hear from her so quickly as she usually takes weeks to respond. She was quick to reply this time. Her reply, “Oh, so I won’t bother you again.” I didn’t know where that came from but to me was the nail in the coffin. There is where anything that was possible (friendship, FWB, booty call) became impossible.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, I have a vasectomy

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Power / Dominance, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol, Marijuana, hashish

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

How wanted was this hookup for you at the time? Somewhat

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? Only my mother and my sister knew about this hookup.

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

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

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 connection was real and really nice.
The sex was amazing

What was the WORST thing about this hookup? She was not 100 with me. I told her never to lie, steal nor take me for granted. She broke two of the three (she didn’t steal from me).

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, I’m retired (from hooking up). I realized that I can get emotionally attached when I make a connection and where chemistry is high. The downside is when it ends. Takes me longer to let go.

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? I learned a lot about myself and women with her. I learned that it is better to be callus than charismatic when it comes to FWB.

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 has now become the norm and people need to realize that. I am not saying cheating is right because it really isn’t. That being said, people who choose to cheat will because the opportunities are too many.

What do you think about the Casual Sex Project? I think it’s great.

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