I Couldn’t Believe What He Asked



What’s your gender? Woman
How old are you? 40s
What country and/or city do you live in? US
What’s your current relationship status? Engaged/Married (monogamous)
How many hookup stories have you here posted before? 1

I Couldn’t Believe What He Asked

How long ago did this hookup happen? Recently

What was your relationship status at the time? Same as current status

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

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 out of town for work and got all dressed up to meet an old friend who lived there for an evening out. I was in the hotel lobby when I got a text from them canceling on me. Disappointed, I went into the hotel bar and got a drink. I was sitting alone in a booth texting when a very good looking man approached me and asked if I was alone.
A few months ago, I would have blown him off, but I recently have had a different perspective (read my previous story) I told this man I had just been stood up and was alone

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it?  We sat and talked through two drinks and I was feeling both tipsy and turned on. I was thinking that I was might dip my toes into the waters of a one night – business trip – infidelity, when out of the blue he says, “last time I met some one here, the going rate was $500 an hour, is that still the rate?”
I suddenly realized this guy thought I was a prostitute working the hotel bar. I have to admit, I got an immediate rush and could feel my pussy tingle. I don’t know what my expression was, but I must have looked shocked, because he asked, “did I say something wrong?”
Luckily, I caught myself quickly and replied, “We usually are a bit more discreet”
Quickly, I decided to see where this would go. I asked him if he wanted a date for the evening and he said “yes”
I asked him what room he was saying in and I told him I would meet hem there in 10 minutes.

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?  After he left, I went to the hotel mini convenience store and bought condoms and a pack of cigarettes ( I don’t even smoke, I just felt really slutty) I went up to his room and knocked on the door. I walked inside and we kissed immediately. He gave me an envelope and I took it and walked into to bathroom to freshen up. I looked in the envelope and there were 5 $100 bills. I was thinking, “I can’t believe I’m going to do this,” but I was also so turned on, that I didn’t want to stop.
I took off my clothes, and put on the hotel robe that was hanging in the bathroom, I put if on but didn’t tie it shut. I walked out and picked up a glass of wine that he had poured for me and let the robe open up for him
We started to kiss and I undressed him and pushed him to the bed where he laid back and allowed me to suck his cock. I reached into the pocket of the robe and pulled out the condoms and put one on him. Taking off the robe and climbed atop him and guided his cock inside me and rode him to a quick orgasm. After my second orgasm, he asked if he could fuck me from behind. We did this in front of a large mirror and it was so erotic and I was so turned on that I squirted. I have to admit I was a bit disappointed when he came, because I could have fucked him all night. Afterwards, I dressed and went back downstairs. I went down to the bar, and smoked a cigarette on their patio, smelling of sex, looking like I just got fucked.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now?  The next morning I had to rush to the airport, but I couldn’t stop thinking about the night before. When I got home, I jumped my husband, who just thought I was horny from being away for a few days.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

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

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? That I stepped way outside the box and did something I thought I would never have considered. And I loved doing it

What was the WORST thing about this hookup? I want to do it again. I just don’t know if I could or if the right circumstance would ever present itself again

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, it made me more open to random sex with hot men

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

All things considered, how NEGATIVE was this experience? Not at all negative

You have a hookup story to share? Submit it here!