[M] First time with a prostitute

This is my account of the first time I went to a prostitute. I’ve previously used sugar daddy type websites, which I’ve also written about on here. I’m not (now) ashamed of what I did, as the woman in question was consenting, well paid, and I treated her with respect. My following descriptions of Anna (let’s call her) and what we did are purely objective.

I found Anna on a website advertising escorts in Manchester. She was Hungarian, late 20s or early 30s. After making contact with Anna I arrived at her address, which was a flat above a shop, which she appeared to share with other escorts. She met me at the top of the stairs. She looked maybe a little older, and less pretty than I had hoped. TBH I wasn’t blown away by her looks, but she was attractive enough, average really (and so am I, so I can’t complain). She did however have a nice figure. Maybe 5’8″, a little shorter than me. Curvy in a nice way. Quite large, pert breasts. I did wonder whether they were artificial, but whatever, they looked good. Light brown hair. Green eyes. She was wearing a kind of skimpy nighty type thing and see-through bra and panties.

She took me into her bedroom, which was bright, and did not feel at all seedy. I gave her the cash, got half an hour of her time. She politely asked me if I could wash my hands, so I did so. I came back into the bedroom, the door was closed  and this is where the fun stuff begins.

Now this was a weird situation for me. I’d slept with plenty of women, but never a prostitute. I felt guilty and there was a moral voice in my head saying “what the fuck are you doing?”. Anna came towards me and I reached out and felt her breasts through her underwear. Oh yeah…I can’t believe I’m allowed to touch her breasts, just like that. Pert, and hard nipples. Hmmm. Really horny now. But, that moral voice in my head… I said to Anna something like “I’m sorry, maybe we shouldn’t do this…is this ok with you?” Don’t get me wrong: I was fucking horny. But I was conflicted. Anna seemed mildly amused by this. Unlike me, she was used to this situation. She said “why don’t we start with a massage?” So I took off all my clothes apart from my underpants and laid down on the bed on my back. She got some massage oil and started rubbing my chest or something. I was just getting hornier, and although still conflicted, I started to fondle and kiss Anna’s breasts as they hung down. And then my fingers went down to her crotch, pulled her panties to the side and rubbed her there. How could I resist? 

I think the animal part of me took over then, and I told her I wanted to have sex, so she took her remaining clothes off and got a condom out. She put it on very carefully and then sucked on my rubbered penis while I stood up. Then she got some lube out, put some on my dick and some on herself. I went into her and we started fucking in missionary. She was making convincing but not over the top moaning sounds. Then I asked her to get onto all fours. It was strange, watching my hard dick slide in and out of the pussy of this woman I’d met barely ten minutes earlier, my hands all over her lovely hips and arse.

Usually when I have sex with a new woman I find it difficult to cum. In this situation it was the opposite. I was really trying not to cum. Partly this was because of residual guilt about the whole thing. I somehow convinced myself that if I didn’t cum whilst inside her it was ok: I wouldn’t technically have “had sex with a prostitute”. Silly, and deluded, I know. So I pulled out of her and knelt on the bed, masturbating, my free hand feeling Anna’s tits and fingering her. I came pretty quickly, filling up the condom with a groan.

I got dressed. We had a bit of chat, Anna told me about her work. And then I left. It was good, but I wish I’d dropped the guilt and just really enjoyed her body for half an hour.

Source: reddit.com/r/gonewildstories/comments/7cfjfz/m_first_time_with_a_prostitute