by Duke

Gender: Male
Age: 45
Race/ethnicity: White
Current location: New Jersey
Highest education received: College degree (eg., BA, BS)
Occupation: Business Executive
Relationship status: Married
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 60ish
How many hookup stories have you here posted before? None

Still Waiting

How long ago did this hookup happen? A Year

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/Sort of Paid Sex

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’ll call her Grace, she was in her late twenties and tall about five seven or eight.  She had long dirty blonde hair and was fit but had a nice chest on her.  She also had nice toned legs, I had seen them a few times.  She worked as a waitress in the diner across the street from the hotel I was staying at.  I thought she was cute and attractive and liked her.  I had been eating there for dinner for more than a week leaving her more and more generous tips.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Now I enjoy pursuing and bedding women and also sex very much.  Some could call me a womanizer but I don’t feel like I am one. I do have a few rules, no women I work with, wives or girlfriends of those I work with, or friends wives.  As a rule I also avoid married women all together other than my own wife.
I am married but my wife and I have an open marriage.  I feel I have never cheated on her in fifteen years of marriage and once we enjoyed a varied and exciting sex life.  However after she had our third child her libido plummeted and she has very little interest in sex and we maybe fuck once every few months.  I need to have sex much more often than that and my wife was good enough to understand and decided to allow me to pursue other people if she could do the same.  I am not sure she has much though.  It’s an arrangement we came to nearly five years ago.  Now don’t get me wrong I still love my wife and our kids but I have needs.
There are a few rules. First I am not allowed to bring anyone to the house, and I have an apartment in town I often stay at during the week anyway.  Second, her friends are off limits not that I would want any of them.  Also, no details unless she asks for them.
Now I travel often for work and usually look for women during this time.  I have had a few I would describe as girlfriends in the past five years but hadn’t had one in a while before this.  I was staying in a rather nice hotel but I didn’t like the restaurant.  I decided on the diner across the street for the dinner and it was there that I met Grace.  I thought she was cute and was attracted to her, and something inside of me wanted to fuck her.  I flirted with her a little and made a few passes at her and left her a sizable tip.
Now I ate there for dinner every night and kept flirting and making passes, and leaving her larger and larger tips.  I took a sizable amount out at the bank and tipped her, and Grace sat down and asked what my intentions were.  I told her I wanted to fuck her and she mentioned a number, I think as a joke but I put that much cash on the table and her eyes went big.  She agreed and we went in the back and I started to kiss her a little and feel her up a bit but she stopped me and told me not here.  She said she would come to my hotel room after work.  I half expected Grace not to show but she was a woman of her word and came to my room around 10.  We ordered a bottle of wine and she had a few glasses and I had one and we kissed a little.

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 started to make out and she sat on my lap on the couch.  I quickly took her shirt off and she had on a leopard print bra which I thought was a bit tacky but I didn’t leave it on long. I played with her breasts a little and carried her to the bed where i pulled her pants off and stroked her legs a bit.  I really liked her legs and she asked me to strip.
We made out naked for a while, honestly it was a little milder sex than I generally go for but I was still quite enjoying myself.  I sucked her tits a little and then mounted her and penetrated her.  Grace began to moan and got really sweaty and had an orgasm which I don’t think she was expecting and I came just a few minutes later.  I got the impression it had been a while since she had sex  We cuddled for a bit, and I asked about the sizable tribal tattoo on her left shoulder which had been hidden by her clothes and she had picked it up in Hawaii.  She was actually much more traveled and educated than I thought and we chatted about all kinds of things until we fell asleep.
In the morning I was surprised to find her asleep next to me.  I ran my hand down her back and legs and she woke up and we went again.  Again just standard missionary but we both came again.  She asked to use the shower and did so and kissed me goodbye and left around seven.

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

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Didn’t really discuss it but I did use condoms both times.  Don’t want another STD and I already have four kids.

What were your REASONS for having this hookup? Something inside of me just really wanted to fuck Grace, happens to me with women on occasion

Were alcohol or drugs involved? If so, how much? A little bit of wine

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 went to the diner again for dinner.  I had enjoyed my night with Grace and was not opposed to another one.  She was polite with me and told me but distant and I left her a generous tip again.  She asked to see me in the back and I followed her.  She started yelling at me, told me she was not a whore and it was not going to happen again. I assured her the money was just a gift to someone I liked, but she viewed it as paid sex and told me she felt very dirty.  She told me not to come in the diner again and if I did she would not serve me.  I did as she asked and filed away the memory.

To whom did you talk about the hookup? How did they react? I did tell my wife who was excited with the details and we ended up fucking.

Was this a consensual and/or wanted experience for you? For your partner? For me it was and I believe it was for Grace, I would never force myself on a woman.

Do you regret this hookup? If so, why? A little bit because of how she reacted.

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 was pretty good if milder than I prefer, if I didn’t mention it above it had also been a while for me and a good release.  I think the worst part was Grace’s reaction to the whole experience.  I have been very generous with partners before, buying them sizable gifts before and after sex.  I feel I may have not handled things completely right with Grace and have been more careful with my partners since.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

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