by Traveler

Gender: Male
Age: 40’s
Race/ethnicity: White
Current location: NorthWest
Highest education received: College degree (eg., BA, BS)
Occupation: Technical Manager
Relationship status: Married
Religious affiliation: Agnostic
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

The Hottie Business Trip Hookup

How long ago did this hookup happen? 1 month

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? I was on a business trip in a midwest town.  Met her at the pizza place bar across from my hotel.  She was about 20 years younger.  Very curvy.  Tight T-Shirt and jeans.  Totally out of my league even when I was 20 years younger.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I sat at the end of the bar.  There was a group of younger people that appeared to be having some drinks after work.  There was one very hot woman that I made eye contact with a couple of times.  She ordered another drink and the rest of her friends left.  She continued to talk to the female bartender that she seemed to know.  They talked about their husbands.  I picked up a bit on the conversation.

We then introduced ourselves.  As the bartender walked away I asked the hot Milf what she was doing next and that I wanted to spend some time with her.  I had never been so upfront.  This was really a fantasy of mine and as I’m getting older maybe one of the last chances to live it out.

She asked me where I was staying and suggested she meet me at the bar at my hotel.

We had a drink at my hotel bar then she asked to sit and talk at a table.  At the table she tells me “there’s something she really wants…”  I’m thinking she wants something really kinky.  She tells me she’s had an “arrangement” with an older professional and it was an amazing turn-on.  She suggest I pay her because it turns her on.

I don’t carry much cash and didn’t have enough to offer her.  I knew she was really horny and just wanted to fuck.  I told her I just wanted to fuck her.  Then she asked me to tell her what I’d do.  I told her I would undress her and suck her tits and lick her pussy.  At that point she tells me she wants a cock in her mouth.  Not making this stuff up…  So we grabbed another drink and took them to the room.  She again asked me for money.  I think the idea of making it transactional totally turned her on.  Her husband had no idea.  I told her again I didn’t have any money and then just started rubbing her huge tits and getting on with it.

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? I reached down her pants to feel her ass.  She had a thong on.  I undid her bra and sucked on her huge tits.  She then undid my pants and gave me my first ever real blow job.  She was amazing and she loved it.

We moved to the bed.  I put my finger in her ass and it turned her on even more.  She  sucked my cock some more.  She then wanted to fuck.  As I got ready to put the condom on she sucked my balls, which was amazing.

She then got on top of me and rode hard.  She was completely shaved with a tight pussy.  I wanted to slow it down and change positions to go from behind.  She wanted to keep going on top and then it was too late, I came.

We both stood up and she tells me she wanted to be fucked in the ass next.  It was like finding some hot gal from a porno movie.  Unbelievable.  She suggested she try to suck me again to make me hard.  She put in great effort but it takes me atleast 30 minutes to get hard again.  She then wanted to lean over and have me finger her from behind.  Such a great ass.  I gave her some slaps on the ass which really turned her on and fingered her from behind until she came.

Did you have an orgasm? Did your partner(s)? Yes, with her on top.  Her from behind by fingering.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condom

What were your REASONS for having this hookup? Bucket list fantasy.
Getting old, one last few chances.  Never had done anything like this before.

Were alcohol or drugs involved? If so, how much? 4-5 drinks each

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 walked her to her car and kissed her good night

To whom did you talk about the hookup? How did they react? no one.  I’ve needed to tell the story

Was this a consensual and/or wanted experience for you? For your partner? yes, both consensual.  Both our fantasies in different ways.  Her fantasy to have sex with an older professional and my fantasy to have sex with a sexy young housewife.

Do you regret this hookup? If so, why? no.  some guilt but mostly new confidence and contentment with my marriage.

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? Lived out a fantasy which still seems totally unbelievable.  I think of people that get paid for sex in a new way.  I think there are people that just really enjoy sex and giving pleasure.  Although I didn’t pay for sex, getting paid was clearly a huge turnon for my partner.  I have felt more confident.  The worst thing about the hookup is having a secret that can’t be told.

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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