by Dale

Gender: Male
Age: 38
Race/ethnicity: Asian
Current location: New York NY
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Computers
Relationship status: Mistress
Religious affiliation: Not applicable
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 0

My Southern Belle

How long ago did this hookup happen? 5 years

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…)? Short fling
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 a tall, fit, tan, 26 year old long haired blonde from the South. She had a penchant for wearing dresses and forgetting to wear underwear. She had moved to New York from Nashville looking for work. We worked together on as consultants. We went out for drinks a few times after work where we would talk about life. She was beautiful and young. I was older and married. I mentioned I was on the rocks with my wife.

One day we went with separate groups of friends to a concert. She abandoned her friends to hang with us. We ended up alone and she made her move. Once we kissed, it was inevitable where this was headed. Truth be told, until we kissed I didn’t see it coming.

Over the course of a hot summer, we fucked everywhere. On rooftops, in stairwells, in public parks.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After the first kiss, we talked a lot about how that was that and nothing else would come from it. We still hung out a lot after work. The following weekend, she asked if she could come over and she was aggressively texting/ calling me. I felt good I resisted but I could only say no so much.

She had been hit on by a co-worker and didn’t like it. She said she needed to see me so I said OK. We made out everywhere as we talked and walked around the city on a hot summer night. She didn’t seem to mind me being very handsy in public spaces. Eventually we circled back to my temporary place where I was staying. A friend was kind enough to let me use a spare apartment off Central Park.

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 agreed to sleep on the couch clothed and without fucking. I was holding her in my arms falling asleep and my hands roamed into her pussy. She was really wet already. The good type of wet where she was thick and sticky. I asked her if I should get a condom and she said yes. I stripped down and put on a condom. I ripped her clothes off. As I pulled off her underwear, I sniffed it. After fingering her for hours earlier and now, it had this amazingly clean smell but stiff crusty texture. It was intoxicating.

We dove right into missionary. She was moaning like crazy and although everything was really vivid and we were going at it missionary and on her side for over an hour, it just went really fast. With her on the side, I started fingering her ass and she was moaning so I kept pressing in a little more until I had a fingertip in her ass. I would later find out she wasn’t so crazy about anal play but we were so into each other being the first time and all she would have let me do anything. She had 2 orgasms pretty close to one another but the whole thing of still being married despite being separated was still in my head. I was getting soft without cumming. I was still horny and only had the one condom. I didn’t want to take it off so we took a 5 min breather mid way. We talked a little more. I was soft and still had the condom on so I had her suck my balls. I got rock hard again we went at it. She came again. I was missing sex, particularly blowjobs. I figured the third orgasm was enough so I pulled the condom off, went in bareback into her wet pussy and used her juices to take the latex smell/ taste off my penis. She said she loves giving blowjobs so I was really looking forward to it. I laid back and she went to town. It had been a while being with a girl who liked giving head and sucking me dry. I warned her I was going to bust soon but she just went at it harder. I was worried about unloading in her mouth but she told me to stop, relax and enjoy. I ripped 4 or 5 solid ropes of cum into her mouth.

Before I knew it we were getting dressed and we went back out for a walk at 5am through Manhattan. It was muggy and sunny but the streets were super empty. Surreal to be so sleep deprived, stimulated from the new sex and walking around an empty Times Square on a muggy summer morning.

Did you have an orgasm? Did your partner(s)? I had one; she had 3.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used a condom. We had talked about STIs and pregnancy risks before hand.

What were your REASONS for having this hookup? I was missing sexual contact and she was beautiful.

Were alcohol or drugs involved? If so, how much? She had been drinking earlier but sobered up by the time she came over. I hadn’t been drinking. No drugs.

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? We spent the summer and fall hanging out, talking through stuff and I really thought about starting a life with her. Ultimately I wasn’t ready. I ended up in therapy with my wife and we reconciled. She moved back to the south; it would be so much harder if she hadn’t.

To whom did you talk about the hookup? How did they react? No one.

Was this a consensual and/or wanted experience for you? For your partner? It was consensual.

Do you regret this hookup? If so, why? I needed the physicality and apparently so did she. The only regret I have is that I’ll never know what it would have been like to date her normally.

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? The sex of a new partner was amazing. The worst, the emotional turmoil I was going through. It changed how I think about sex and emotions of being separated at the time. I think if I had another situation where I was separated, divorced, widowed, etc. I wouldn’t jump into another relationship but I know I probably would take the sex again.

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

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

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