The Walkup

by Yaller

Gender: Male
Age: 66
Race/ethnicity: White
Location: California
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Sports instructor
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)? between 100 & 200
How many hookup stories have you here posted before? 0

The Walkup

How long ago did this hookup happen? 2 months

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? I met N. by calling an Escort Service while I was in NYC for a week. The person who answered said that there was an apartment near my hotel where we could meet and described 3 different women who were in the apartment. 2 were described as buxom and 1 as slender, that was N.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The site was a loft building in the former garment district. I had worked in a factory in this area while in HS, so it felt very familiar. But now, all of the buildings have shops, bars or restaurants on the first floor. I got there a little early so I sat on a bench outside a bar to wait. Then a really weird thing happened. A mid 20s couple came out of the bar to have a smoke and talk. She was about 5’10”, slim but busty, with shoulder length light brown hair, perfect skin, light makeup, a hip length jacket over a clingy skirt that reached her ankles. He was about the same height, slightly dark skinned, well groomed and wearing a very expensive suit. They were talking in  normal conversational tones about a handgun they’d left in New Jersey, whether they should go retrieve it and whether bringing it into the city was a good idea. As they talked, they walked a little to the west and then stopped, she facing west and he, east. It was late afternoon and the sun shone through her skirt, almost undressing her. Her legs were long and shapely in heels, her butt was tight and it was bare, she had a thigh gap and her vulva were clearly visible. Its pretty damn hard not to stare, so I closed my eyes and leaned back until I heard them start to walk away. When I looked again, it was the same view, in motion. I hadn’t been feeling all that hot before, but this unexpected flash changed all that. When it was time for the appointment with N. I walked into the small lobby and found that the elevator had been marked out of order, making the apartment a walkup. There were no signs in the lobby indicating which businesses were in the building, but the receptionist had told me to go to the fifth floor. As I walked up the stairs, both the second and fourth floors had signs indicating that they housed ‘Spas’. There was only one marked door on the fifth floor, containing the name of the Escort Agency I’d called

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I rang the bell and a tall, athletic, light complexioned African American woman, dressed in Jeans, opened up. Two other women, similarly dressed were sitting on a couch, watching TV. When I introduced my self, the first woman said she was N. but before letting me in, asked me to open my pants and show her my penis, to prove I was a legit customer. She kissed it lightly, then took me by the hand to her bedroom. Being a former factory building, the ceilings were 15′ high and the tall, street facing windows in her room were wall to wall, making it bright and cheery, with thin curtains offering a filtered view of the street below.
We lay on the bed talking a bit about our backgrounds, we were both from Brooklyn, had younger sibs and both had worked in hospitals at times. She asked if I “liked Black Girls” and I said it didn’t matter at all, but that led to a short discussion about race and the practice some escorts have of advertising “No Black Men”, which N. seemed to agree with. As the conversation moved towards what we might do together, she  said that she only had 2 limits with clients, “no anal” and “no fingers inside”, both fine with me.
I didn’t want a massage, so we made out for a while. Then she gave me very delightful, bare, oral sex, switching to covered intercourse after I told her that I just don’t reach orgasm via oral any more. She was on top and the sex was pleasing but my erection started to flag, so I asked if she would like to receive  oral or just talk a bit, while manually stimulating me. She asked for oral. I started slowly, kissing the tendons at the top of the inner thighs, licking the vulva, then the clitoris and felt her shudder just a little. When I put my mouth over the mons and clitoris, and my tongue into the vagina, she pushed her pelvis up and said, “Don’t stop” a few minutes later she reached down, grabbed my hand and without a word, guided my finger into her very wet vagina, pushing it up against the front wall.  There was no doubt when she came a few minutes later and I was as now hard as a teenager. I had been giving her oral for about a half hour at that point. So we rested embracing side by side, ignoring the alarm when it signaled my hour was up. She went down on me, bare, again, giving me a huge and long-lasting orgasm.  After washing me with a hot towel, she dressed and we talked about life in California.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condoms during intercourse, no conversation needed

What were your REASONS for having this hookup? I was in NYC, which is my hometown, feeling emotional, lonely and a little horny

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 felt great and would be very glad to see her again.
I feel very positive about her, she is comfortable in this work, but has career goals beyond it that I feel are realistically likely to be met. We are only casual acquaintances but we had a meaningful and sensitive personal connection

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? For both

Do you regret this hookup? If so, why? No

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 aspect was finding the personal connection, which enabled a pleasurable sexual encounter for both of us

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

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

Anything else you want to add about this hookup or anything else? People who have no experience of casual or paid sex usually are dismissive, thinking that its automatically tawdry and impersonal, but that is clearly not true. These are real experiences, involving vulnerability, feelings about who you are, trust and yes affection. It is a shame that talking openly about them leads to ostracism, contempt, and in the case of paid encounters, prosecution.  I led a monogamous life for more than 30 years and only started seeing other women when my wife declined, several times, to discuss our evaporated sexual and affectionate relationship. I value and love my family and my wife very much, but I’m much happier now that I have other regular sexual partners, only some of whom are sex workers.

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