The original post: /r/sluttyconfessions by /u/Plane-Estimate-8024 on 2024-12-20 02:10:03.

I (29 / 30 M at the time) had a girlfriend at the time, and she had to left to attend personal issues. I was gonna be home by myself. I was horny so I started looking around in Craigslist — that’s right, craigslist — and I found a relatively normal (e.g. not nasty, sketchy, vulgar) post of a “NYC private companion”. I reached out, shared a little bit about my stats but also myself (tastes in music, job, interests, where in Brooklyn I was living at the time, etc) and asked for more details. She replied very promptly and warmly. We exchanged a couple of details and we agreed on a date, on saturday. We were gonna go for dinner and then decide from there.

The day of the date, she emailed again, asking if I was enjoying the lovely rainy weather and if I was still up for the date, I confirmed. She asked me what I was gonna dress or how she was gonna recognize me, I said “long hair, will wear black, will have a book”. I asked her to dress cute and not over the top (this was the first escort I’ve ever encountered) and she said she was gonna wear a cute dress.

We got to the restaurant, had a nice dinner, went to my place, and we discussed if she was gonna stay all night or just a couple of hours — she confessed she was fairly new. She stayed all night. We fucked. She was amazing. She asked for what she wanted, she asked me to be on her back. We woke up tired, fucked more, she took her gift and left.

After a couple of days, we kept emailing a bit, I invited for lunch in Chelsea [Manhattan] and she agreed! We went for pizza, she told me she worked in the arts. We flirted a bit. After lunch and before I had to go to work, she confessed “this… this thing I’m doing… I’m not goin to do it forever, you know?”. I asked to kissed her, and we kissed passionately. She felt how hard I was getting, and I asked her “do you feel me?”. She moaned a little bit.

She reached out with a very personal email. Told me her real name, what she do, etc. We discussed our situation and how dangerous it was to cross boundaries. I replied with my personal email, real name, etc.

One day, I just reached out to her, boldly “I want to see you. Come to my place tomorrow, at noon.” She obediently just replied, “ok”.

She arrived, and we just started to make out. She was so horny and said “I’m very wet”. I opened her shirt, and saw she was wearing very sexy black lingerie, and she said “it’s for you”. We fucked like crazy. It was so intense. She on top, me on her back, missionary with her legs on my shoulder. I would pull her hair and she’ll scream “damn, you’re so fucking sexy!”. We came a couple of times. And she left.

We exchanged a couple of emails of how nice it was to have crossed paths, but that it was to complicated to move forward.

The end.