by Ann123

Gender: Female
Age: 36
Race/ethnicity: White
Current location: New York
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Company COO
Relationship status: Single/Divorced
Religious affiliation: Chrisitan
How religious are you? Somewhat
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Straight but experimented with women
How many sexual partners have you had in your life (including oral sex)? 60+
How many hookup stories have you here posted before? Zero

Cutting Lose One

How long ago did this hookup happen? Two Months or so

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…)? One Night Stand

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? Scott was a handsome man, a few years younger than myself (late twenties I think).   He had a short beard and a toned muscular body and overall a bit of a hipster look (judging from the bar that night he probably was a hipster).  I met him at the bar the night we hooked up  He was charming and I was instantly attracted to him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Since this is my first post I will share a little background.  I have been sexually active since I was fifteen.  I was married to an older man for a while in my twenties, he and I split nine years ago now and were divorce a year later.   I have had a few boyfriends since but have been single the past three years.  I have also had numerous hookups.
Now I find sex extremely pleasurable and enjoy having it recreationally.  A lot of women do but would never admit that. I came from a religious background and also would never admit this to many people or anyone I work with.
So one piece of advice my first mentor advised me was that she liked to always have sex the night before anything big at work.  I also find sex very relaxing and always feel very focused after and usually for days and have followed her advice.
Now I had a big presentation to the Board of our company the next day.  I had no boyfriend and had also recently ended things with a guy I had been in a fuck buddies type arrangement with for more than a year.  This meant I was going to have to attract a mate.
I shaved my legs, put on a thong and short shorts and a tank top that showed some cleavage.  As a fit woman with large breasts I have never struggled to find a partner when I desire one.  I hadn’t done this for a while and I am a bit old for the club scene now so I went to a bar I used to frequent.  It had changed in the year or so since the last time I was in there, the crowd was a bit younger and had the hipster look to them but I recognized the bartender.  He said they had moved in a few months back and taken over.
Still I wasn’t exactly looking to go somewhere else.  I few guys bought me drinks but I have standards so I wasn’t just going to jump in bed with the first one that bought me a drink.  Scott bought me a drink, and I felt an instant attraction to him.  He was pretty charming and we flirted a bit.  He asked if I wanted to go to his place since it was within walking distance and I said yes.

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 walked back to his place and I let him grab my ass a bit.  At his place we made out and undressed and ended up on a shag carpet on the floor of his living room.  I like being in control so I mounted him and let him feel me.  He kept grabbing my boobs and leaning forward so we could kiss while we fucked.  I moaned and screamed a bit as it felt really good.  He came and then I did and afterwards we both laid there for a bit. He said he was a little surprised at how loud I got and I told him it was because I was enjoying myself. I asked to use the bathroom which was past his bedroom.  I had intended on peeing and getting dressed and leaving.
On the way out he surprised me.  We started kissing again and then he put me down on the bed and turned me around and penetrated me.  As I said I like being in control so I don’t normally enjoy doggie or even let guys fuck me in that position.  Still it felt really good again to have his hands on me again and he grabbed me by the waist hard and fucked me.  He got loud and sweaty and we both ended up coming again this time in near unison.  He laid down after and fell asleep and despite how late it was I got dressed and left.  I had gotten exactly what I came for, a good fuck.  Also as a rule, I do not sleep over.

Did you have an orgasm? Did your partner(s)? We both did both times

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Didn’t discuss it but he wore a condom both times.

What were your REASONS for having this hookup? I wanted to relieve some stress and I was horny.

Were alcohol or drugs involved? If so, how much? I had two glasses of bourbon all together, but a few guys had bought me drinks

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? I nailed my presentation that next day.  I ended up with bruises on my waist from where he had grabbed me so hard and I was a little sore.  We ended up texting back and forth a bit and I considered seeing him again but I decided he was a one night stand only and broke contact.  Scott seemed to understand and stopped texting me and I saw him out recently with some blonde hipster type around his age.   I am happy for him actually.
This also started me on a period of self reflection the past few months about my life and how many partners I have had. I will share more on that below.

To whom did you talk about the hookup? How did they react? I haven’t told anyone because honestly it’s none of their business and I don’t need the judgment

Was this a consensual and/or wanted experience for you? For your partner? Yes for us both

Do you regret this hookup? If so, why? Yes a bit because of some of the realizations after

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? I would say the best part was the sex, it was pretty good.  I would say the worst part was how I have been feeling lately following this and a bad hookup I had about a month ago.  I realized it’s been more than three years since I had a boyfriend and I have been sleeping around having meaningless sex for a while.  I have also realized I might still like to have children and a family even though I have always focused on work.  So I would say yes this did change how I feel about casual sex.  As I said above I find it really pleasurable and fun but I want more.

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

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

Anything else you want to add about this hookup or anything else? I have a few others I am comfortable sharing and will post them as I have time

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