The First Time a Man Paid Me for Sex

Horny, I went to bed with him for money. He didn’t victimize me.

Conrad was a new client. An African-American man in his thirties, he was slightly heavyset, shorter than I was, and had a sweet smile.

I directed him to lie back on the bed. Straddling him, I slid just the tip of his penis inside of me.

That was all we had agreed on — that he could only insert the tip.

But it felt so good. I realized I was dripping wet. I shocked even myself by how turned-on I was.

I threw caution to the wind and slid the rest of him inside of me.

I came hard.

I also became a prostitute.

I’d had a personal bias against becoming a prostitute.

I crossed a boundary that day. I’d fought against becoming a full-fledged prostitute for years. I wouldn’t even admit to myself that I was a working girl.

I classified myself as a dominatrix, not as an escort.

I posted ads in the BDSM section of the website I advertised on. I didn’t advertise in the escort section. I saw myself as being different than an escort.

An escort had sex with her clients. A dominatrix didn’t.

But still, I couldn’t deny I did to do sexual things with my clients. I offered “sensual” experiences, alternating between punishing my clients and pleasuring them.

Even as a dominatrix, I’d given a lot of handjobs. I’d also let men perform oral sex on me. I sometimes allowed analingis as a “reward.”

But penetrative sex — I never allowed that.

As long as I didn’t cross that boundary, I could say I wasn’t a prostitute.

Understandably, I didn’t want to think of myself as a hooker. Prostitution is the most taboo thing a woman can do.

I had a “no sex” rule.

This was why, over the phone, I always told each new client several times that I didn’t offer sex.

Well, I did offer sex — just not penetrative sex.

I’d told Conrad this when he called. He’d said he was okay with that rule, hadn’t he?

But then when he arrived at my apartment, he asked for sex.

He wasn’t being a jerk by asking for sex with me. I suspected he was oblivious to certain social cues. Maybe he was on the spectrum.

He giggled and I noticed he had a nervous tic. I didn’t doubt he had trouble meeting women in the real world.

Still, I told him the answer was no.

“What about if it’s just the tip?” he asked.

Why was the “just the tip” okay with me?

It’s hard to pin down exactly why I thought letting him only insert the tip of his penis inside of me wouldn’t make me a prostitute. All I can say is that I was still playing the same mental game I’d been playing with myself for years.

I pretended what I did sexually with men didn’t make me a prostitute.

As if by just accepting the tip of a man’s penis inside my vagina wasn’t having “real” sex. Like I could blink and pretend it never happened.

I’m not saying what I believed was logical. I’m just explaining my thought processes at the time.

What had changed in my life?

I was open to new experiences in general at that point in my life. I’d just recently left my kids’ father and had since gone back to working in the sex industry.

I was horny. I was playing the field after years of frustration in an almost sexless marriage.

I was having a lot of sex with men anyway — for free. And here was his man wanting to pay me for sex — the sex I already had so easily in my dating life.

I was going to bed with men I met on dating apps, often on the first night. I asked myself why I couldn’t do this now with Conrad — especially if it also meant making money?

I was finally honest about being a prostitute.

But then I had still agreed to let him penetrate me with only the tip of his penis. In the end, my arousal won over any fear of crossing my “no sex” boundary.

After accepting the tip of Conrad’s penis inside my vagina, I decided to insert all of him inside me.

I rode him until we both came. I surprised even myself by how much I liked it.

And yet I’d always expected something terrible would happen the moment I crossed that boundary. The skies would darken. Rain would fall. I’d be pulled away in a flood.

Nothing terrible happened.

Well, something terrible did happen that day — I finally committed to becoming something that society hated.

A prostitute.

At least I was finally being honest with myself though.

No one forced me to have sex for money.

After that, Conrad became one of my regular clients. I suppose he felt accepted by me. I was right about him having trouble meeting women. He felt indebted to me for breaking my “no sex” rule by having sex with him.

It was a win-win for both of us. He enjoyed the sex. I enjoyed it, too.

Now that I’d crossed that boundary, I also started to have sex with other men for money.

I committed a crime each time I went to bed with a man for payment, and yet it was a victimless crime. At least it was in my case.

No one got hurt. On the contrary, both of us benefitted. The man left happy and I ended up a few hundred dollars richer.

I realize I’m privileged.

I understand the fact I’ve had a choice in the matter means I’m incredibly privileged. I don’t have to have sex with just anyone. I’m not starving. I’m not a drug addict. I don’t need a fix.

I have sex for money because I want to — and crazily enough, I like it.

I won’t say that every single experience has been perfect. If I don’t like a client, though, I don’t see him again.

I don’t feel ashamed about what I do. I do wish I could be more honest with people, but I can’t.

The world isn’t ready to accept what I do for a living as a valid job.

At the very least I can now accept it. ❤️