Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Relationship status: Single
Religious affiliation: Catholic
How religious are you? A little
Sexual orienation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 23
How many hookup stories have you here posted before? A Few
How long ago did this hookup happen? Ongoing
How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Friends With Benefits
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? I met Carla my first week in Boston. I am not a fan of Starbucks so I was looking for a small shop to frequent, and I found the shop where Carla works. She’s a pretty Latina, five-five with long black hair and 22. She is thin but had a nice chest and ass.
Carla and I had been friendly and talked about her college, she was going part time and working as well. She bent over a few times so I could get a good look at her ass, and she likes to lean over so I can see down her shirt when she wipes tables or pours coffee. I thought she was just being friendly to get bigger tips. I liked talking to her during my stops in the morning, or in the afternoon when I needed a pick me up. Usually I ask for Carla or try and go in when I know she is there. One of the other baristas I am also friendly with told me Carla had a bit of a crush on me. I feel I have gotten to know Carla pretty well over the past few months.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A colleague talked me into going out for drinks. I like scotch but I have never truly been into the bar scene. However we had just made a major breakthrough in our research so we went out to celebrate. I had just ordered my scotch when Carla walked in. I wasn’t looking for anything, I had broken up with a very serious girlfriend (see The Cop) when I had moved to Boston and had only one other brief fling since.
She was dressed very different than at work, a tight red tank top that showed a lot of cleavage and tight jeans. She also had her hair down and several of her tattoos were visible. I was checking her out a bit and Carla would admit to me she had been looking to get laid that night.
My colleague told me to go ahead and I walked over and asked her if I could buy her a drink and she said yes. We talked, and flirted a bit and she brushed up against me and touched my arm. I could tell there were sparks and I was attracted to her. I asked if she wanted to go back to my place and Carla said yes.
It was only a few blocks and we went inside. I had just gotten a hot tub for some back issues and Carla asked if we could go in and had a bikini with her which I found weird. Still I said yes and went into my bedroom and got trunks and went in.
Carla came out a few minutes later, in a black bikini that left little to the imagination. She was a lot curvier than I though, had numerous tattoos and a pierced navel. Her breasts were also busting out of it. Carla sat a few feet away until I worked up the nerve and pulled her close and began to kiss and touch her. She straddled me and we began to make out.
What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? For the record hot tub sex isn’t like the movies. Jets spray everywhere and it’s hard to get comfortable. I turned the jets off for this reason. I undid her top and tossed it aside and saw her breasts for the first time. We made out with her topless and I licked and sucked her breasts a bit like I like but they tasted heavily of chlorine.
I removed my trunks and untied her bikini bottom and had her naked. In that moment I really wanted her so I grabbed her and entered her. We fucked in several different positions, water splashing everywhere. However neither one of us could orgasm even after a while so we decided to relocate to my bedroom.
I got towels and we dried off quickly. Carla laid down on my bed and asked me to take her from behind. I have always enjoyed doggie so I said yes and put my cock in her and grabbed her hips and fucked her. We actually both orgasmed quickly and in near unison, something I have found is very rare with a woman. After this it was pretty late and we fell asleep.
I awoke the next morning and found I was in bed alone. I found Carla in the living room getting dressed. She had her pants and bra on and was looking for her top. I could tell she was a little embarrassed at having given into lust. However I grabbed her by the belt and pulled her to me and began to kiss her. I took her bra off again and we made out and then Carla moved down and began to give me oral. Ultimately we fucked one more time. Carla had to be someplace so she left.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used condoms and Carla is on the pill. We both recently tested clean and have fucked once bareback and we have decided to continue doing so in the future.
What were your REASONS for having this hookup? I wanted her and I was lonely.
Were alcohol or drugs involved? If so, how much? I had one glass of Scotch and Carla two Manhattans
What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? That next Monday coffee was a bit awkward between me in Carla. She pulled me into the back so we could talk in private. Carla said while she had enjoyed herself and me she was not looking for a relationship and I said I was also not looking for a relationship. However I did kiss her and talked her into coming over that night and we fucked again.
It’s been about six weeks now, and we have settled into a rather casual friends with benefits arrangement. Carla is fun both inside and outside the bedroom. We play video games, have been to the movies a few times (more Sci-Fi like I like) only problem there was she stuck her hand down my pants a few times. Carla also likes to dress up and go out to eat, letting me explore my foodie side and it’s nice to have someone to enjoy that with. Inside the bedroom Carla is very open and the sex is good. We hang out and if it heads in a sexual direction so be it, if I call her and Carla wants to come over and fuck she does. If it’s late Carla stays over.
This is casual, a bit different for me. I was considering a break from relationships but Carla changed this. I have also found I need sex on a regular basis to function. For the future, well I don’t think I see this relationship turning serious but I intend to enjoy it while it lasts.
To whom did you talk about the hookup? How did they react? My colleague who was impressed at my bedding of a much younger woman. He is married and has been for a long time so I think he was living a bit vicariously.
Was this a consensual and/or wanted experience for you? For your partner? For me and Carla both very much.
Do you regret this hookup? If so, why? Not at all.
What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Good sex with a great person without strings attached. As for the worst part, I haven’t seen any yet. For me having a casual sexual relationship is very different, but I am enjoying it. I do feel a lot better about myself since I started with Carla.
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 or anything else? This didn’t really fit in any of the other sections. Before my hookup with Carla I was considering a period of celibacy. I have always been the more relationship type, and have pretty much been someone’s boyfriend since I was 20. Even was a fiancé for a time (see Freckles). However my hookup with Carla changed that.
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