Not Your Usual Virginity

If the Hooker Academy were giving out awards for Funniest Experience With A Client, I should really start preparing my acceptance speech.

Last night I met up with William, a slight middle-aged man with a nervous laugh. We emailed back and forth several times hammering out the terms and he almost cancelled due to the fact that he suspected that I was a police officer. I reassured him that I wasn't and he finally believed me. I drove the 30 minutes to his luxury condo and had to be buzzed upstairs by the attendant at the front desk. When I rang his buzzer, he let me into his apartment which I thought smelled like pot. I could tell he was extremely nervous by the way he was shifting and avoiding my gaze, but I didn't think much of it. I knew he didn't have much experience with sex workers and nervousness isn't really out of the ordinary. He took my coat and we sat down on the couch. I noticed the ashtray full of cigarette butts and ashes; he had clearly been chain-smoking all night. After shifting in his seat for a minute, William turned to me.

I have a confession to make.

Ok...?

Suddenly, an inkling of what was to come began to sprout in my head.

He blushed and grinned sheepishly. Well...um...I've never, um, been with a woman before. I've never, um, even seen one naked.

I looked around at his beautifully decorated luxury condo, the coasters on the table, the diamond stud in his ear and made the leap. My eyes widened.

So you've only been with men?

Well, there was that one girl in high school, but that didn't go so well.

So there I was. With a bonafide gay man. One who was curious about women and who had hired a hooker to find out. I was living out every fag hag's fantasy.

Can I confess something to you to that might make you feel better?

He nodded and blushed again.

I'm mostly gay myself.

William looked at me with shock. Oh god! I've hired a lesbian!

I tried to assure him, but that particular piece of news seemed to make him even more nervous. He offered me something to drink and I asked for some water. When he sat back down on the couch, I assured him that I would do everything I could to make his first time comfortable. I began to lightly touch his arms and William told me how lately he had "just had a feeling" about wanting to sleep with a woman, a "busty" one in particular.

He began to touch my breasts, but there was a dress and a push-up bra in the way. I asked him if he wanted me to make it easier for him and he nodded. I stripped down to my underwear and took off the bra. William started to touch my breasts for a minute before jerking away and shaking his head.

Oh my god! I'm objectifying you! This isn't right!

I assured him that I was ok with consensual objectification and he continued to feel my breasts. I suggested we go to the bedroom, where William carefully took off each piece of clothing until he was down to a pair of styled white briefs and tube socks. He stepped close and began to grind against me, first touching my breasts and then dipping his hand down to my underwear. Because he had never even seen a woman naked before, I was afraid of what he might try to do with my hoo ha. So William fumbled around down there while I tried to jerk off his obviously soft cock. After a minute I took out a condom and some lube.

What can I do for you?

He looked kind of confused and didn't answer.

Do you want to see it?

He nodded his head and I took off my underwear. William reclined against his headboard and began to try and jerk himself off. I spread my legs and let him get a full look at my pussy while I made slow circles around my clit. He stopped abruptly.

Is that it?

Um, yes.

William buried his head in the pillow and I had to reassure him again before he started back up again. He was still soft. After another 10 seconds, William stopped again.

I'm really sorry, but I just can't do this.

It was inevitable. I had known since the second he had told me he was gay that he wasn't going to be able to fuck me or even get hard.

See, I have 7 sisters and I just feel like a dirty old man!

I assured him again that I didn't think he was a dirty old man and that it was ok if he didn't want to continue.

I do like those, though, he said, gesturing towards my breasts.

I offered to let him play with my breasts for the rest of the hour, but he objected on grounds that I would get bored.

Well how about this, then? Let's go back to the couch and talk. I'll sit there topless and if you feel like you want to touch them, you can.

William agreed and we both put our underwear back on. We began to talk on the couch and William unloaded all his questions about women and female anatomy. I explained to him the anatomy of the clitoris and the location of the g-spot. He was fascinated. He also told me about going to an all-boy school as a kid and getting kicked out of seminary school. After about a half an hour of lively conversation, William told me that he wasn't going to keep me any longer. I apologized for not being able to do more for him.

Well you know, baby steps.

I agreed and told him that if he ever wanted to take another baby step, I'd be more than happy to accommodate him. We hugged goodbye and I waved as I walked out of the door. On the way to the elevator, I looked at the fat wad of twenties in my purse and grinned.

If there was ever an empire to be built on servicing gay men curious about pussy, I'd be the first in line to head it up. Cause y'all, that shit was priceless.