Naughty Waitress

by Handsome Exec Virginia

Gender: Male
Age: 47
Race/ethnicity: White
Current location: Virginia
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Sr. VP
Relationship status: Married
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 135
How many hookup stories have you here posted before? 5

Naughty waitress

How long ago did this hookup happen? Last 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…)? 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? From time to time I’ll pay for sex but only if it achieves something I’ve never had before — a certain ethnicity, for example, or a model. This was a little different in that “M” hadn’t escorted before. I met “M” at a restaurant — she was a waitress at a high-end restaurant during a business dinner. She was short, very pretty with dark hair and piercing blue eyes. She looked fantastic in a black outfit with tight pants and apron. I couldn’t help but notice her ample breasts. We exchanged glances but that was it. A few days later I was perusing the local escort selections, which I rarely do. And there she was — a full face photo, which is rare. Her ad said this was her first time doing something like this. I made note of the phone number (from out of town) and put it aside for a few days. Later in the week I looked again and she wasn’t visible on the post. But I called and she answered right away. I told her we met before and not to freak out but I wanted to set up a date with her. So we did and she asked me to come to her apartment that afternoon.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I called her from outside the apartment lobby and she came down — the same person who was our waitress. She led me to her apartment and I took a seat. I learned that she was a master’s degree student from another state and that she was new in town. We actually talked for 20 minutes and I found her to be smart, ambitious and focused. She was 27 — 20 years younger than me and ever so beautiful in daytime lighting. She was wearing pants and a blouse. I asked her why she was doing this and she said for the money and the excitement but revealed she would only be doing it for a week. As it turns out I was her first paying date. She also said she had never been with an older man and was really turned on having met me before. I assured her she was in the right hands. After more talking and ensuring we had protection on hand, I leaned in to kiss her.

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 french kissed for several minutes, each of us exploring each other with our hands. I was rock hard just feeling her breasts — large natural Ds. I took the lead and after making out a good 15 minutes I began to take off her clothes. She seemed to enjoy it as I explored her massive and very beautiful breasts. I kissed her flat belly and pulled down her pants and then her panties, revealing dark natural bush. She was not up for oral so I rubbed her with my hands until she quivered. I then put on a condom and asked her to mount me. She said she had never done that before, showing she didn’t have a tremendous amount of experience. At any rate, we went at it in multiple positions until we both lay exhausted on her bed.

Did you have an orgasm? Did your partner(s)? I came inside the condom while doing her doggie style and holding on to those succulent breasts. I believe she came when I rubbed her — hard to tell.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condom.  We did not discuss history but I sensed her nervousness in the beginning and I told her I was clean.

What were your REASONS for having this hookup? She needed the money and I was in the mood — but I only did this because it was the same woman I met waitressing.

Were alcohol or drugs involved? If so, how much? None.

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 texted her afterward and told her she did great for her first time escorting. I told her if she ever wanted to hook up again I would be ready. A week later she texted to say she didn’t want to escort anymore, that she slept with a few men but didn’t get into it. She said she really liked our encounter. I saw her on the street once while with business colleagues and waved hi but haven’t heard from her since.

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? Yes. I’m was surprised at the guts she had for wanting to start escorting all of a sudden.

Do you regret this hookup? If so, why? Not at all.

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 best was realizing the waitress I was attracted to was available to sleep with. The worst was that I had to pay. I don’t do it much and I’m always careful it doesn’t go to someone into drugs or pimps.

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

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

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