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.

Missed Connection

It was Friday evening at 2:37 in the morning when my phone bleated to announce that I had a text message.

I cracked an eye open, wondering who it could be so late/early.

Do you want to make [a large dollar amount] cash?

The text was from Mr. Freddie Prinze. Yes...how? I texted back, glancing nervously at the toddler laying next to me in bed. I was babysitting her for friends and crossed my fingers that whatever it was he wanted me to do, it would be tomorrow. My phone bleated again.

Me and a friend.

Yes, but can we do this tomorrow? I can't tonight.

Shit!, I thought. There's no way I can leave her here while I go out whoring. And, like I predicted, Mr. Freddie Prinze wasn't interested in a threesome tomorrow. I texted him back to tell him no, put my phone down and tried to go back to sleep, but all I could think about was a scrolling marquee with that dollar amount flashing in big shiny letters. I needed the money, but I couldn't figure out what to do.

Finally, after about 40 minutes of obsessing, it hit me. For that amount of money, I reasoned, her parents wouldn't be too upset if I dropped their kid off at the hotel room where they were staying. After all, the parents know what I do and are very supportive of me. I figured I'd offer to buy them breakfast or something.

I texted him back. I might be able to work something out. How late are you all going to be up?

This time, he called me back. I explained the situation and he said he'd try to work something out. I'll call you back in 5 minutes.

After 15, I still hadn't heard from him. Are we on?, I texted.

Not 2 night 2 late.

By that time it was almost 3:30 in the morning and I couldn't help but agree.

I'm still kicking myself.

Bewilderedly disappointed

I haven't heard from Mike yet and I don't think I will.

Why am I kind of sad about that?

Crushing on a client is so very weird

Oh, what a night. Readers, I'm not sure if I can quite capture the hot insanity of my first date since Chad. But let me try.

Mike and I had arranged a date for Friday evening around 9 or 10 p.m. He invited me out for drinks beforehand, but I declined as I always do for unpaid activities such as that. By 11, Mike still hadn't called and I was quite annoyed, having chucked all plans for the evening only to be stood up. However, at 1:00 in the morning, my phone chirped with the sound of an incoming text message. It was from Mike. Can we still meet? I responded no, but wished him a nice evening. He texted me back immediately, asking why not. I don't tend to make a habit of rescheduling with people who don't call and ruin my plans for the evening, I wrote back. He texted me back, promising to make it "worth [my] while." I asked him for specifics and he wrote me back. But in my half-asleep stupor, I thought he offered me twice as much money. Later, I went back and saw that Mike had instead promised me at least two orgasms. Whoops!

I threw on some clothes and makeup and headed out the door. Mike lives about 45 minutes from me, but I did it in 30 because there was no traffic on the road. I got to his house at about 2:00. I called him to let him know that I was there and he informed me that he'd be there in 20 minutes. He was at a club with friends and told me that he was going to call a cab. That was quite an underestimate, however, because it wasn't until almost an hour later that Mike finally showed up. I was livid and wanted to leave, but I also didn't want to not collect my money.

Mike climbed out of the cab and another guy trailed behind him. I was shocked. Mike was incredibly handsome. Think Freddie Prinze Jr., only not so pretty-boy. I was intrigued. However, when he stepped aside, I saw that his friend had a trail of fresh puke all over the front of his peacoat. He was stumbling drunk. Mike apologized for his drunk friend and promised that he would put him to bed immediately. We got inside his apartment and I sat on the couch while Mike tried to get the friend to sleep in his bed so that him and I could do what I came for. The friend kept on asking who I was and why I was there.

Finally, Mike got his friend into bed. He went over to his kitchen counter and to my shock, he did a nosefull of coke. I thought about saying something, but I decided not to. Mike asked me how we should proceed and I indicated that I needed payment first. We need to go to the ATM, then, he said. I was getting even more annoyed at this point, but I wanted my money and I'm also a sucker for cuteness. I drove Mike to the ATM and he asked me lots of questions about my career as a sex worker. He seemed incredibly fascinated. I also didn't mind answering his questions, since I'd rather talk about the business than where I grew up or what my day job is like.

We got back to his place and the friend was still wandering around. Again, Mike shooed him to his bedroom, but the friend was drunk and wasn't listening very well. After a bit, he finally went into the bedroom and Mike and I got started. I had mentally decided that since he was really cute that I was going to try and enjoy the sex for real and not just because I was getting paid.

Bare-chested, I began to cover his chest and stomach and collarbone with kisses. Slowly, I moved up and we began to kiss. I didn't mind his kissing style, but I wasn't turned on. Mike was in love with my large breasts and played with them frequently, sucking on one nipple while tweaking the other. I took down his jeans and he was soft. However, after some stroking and licking, his cock was fully erect. It was nicely shaped and maybe slightly above average in size. I began to go down on Mike and all of a sudden, the friend walked into the room and started giggling. Mike immediately went soft and yelled at him again to go back to the bedroom and apologized to me profusely for his friend's bad behavior. He did another line of coke and then we began again.

This time, however, Mike could not get hard. No matter how much lube, licking or sucking I ministrated, his cock stayed small and soft, which I'm sure had lots to do with all the alcohol and coke he had consumed. I reassured him that having a friend interrupt me would turn me off instantly as well, but he was quite frustrated. He then decided to fuck me with his hands, which I enjoyed at first because he found my g-spot right away. I really wanted to enjoy the sensation of being fucked by a very handsome man, but I found myself having all sorts of body image issues. So here he is, this traditionally attractive 30-year old dude with a perfect body and me, the fleshy girl with rolls and cellulite. Even though I knew he found me attractive, I couldn't help but feel really uncomfortable in my own skin.

Mike continued to fuck me with his hand until he remembered that he owned a toy. He brought out a short and fat g-spot vibrator. Before he fucked me with it, though, he did another line of coke and poured a tiny bit on my nipple, which he then licked off. Strange, huh? I think he was trying to be glamorous and decadent, but as my friend said, "I think he maybe just read too many Harold Robbins novels." I told Mike to turn the vibrator on high and fuck me hard. That he did. So much that the lube began to wear off and I began to get sore. So since we had used nearly all of my lube trying to get him hard, I faked a convincing orgasm even though he had begged me earlier not to fake it. I was sure that I wasn't going to be able to get him hard, so I thought it'd be some consolation that I had "come."

My predictions were right. We tried for another several minutes, but Mike's cock was as limp as ever. I think he just got too frustrated and stressed about his friend being there and about the pressure to perform, you know? I felt bad that he had just paid me several hundred dollars and hadn't gotten an orgasm, but there wasn't much I could do. Plus, although I didn't have a clock handy, I knew it had been over an hour since we had started. To my chagrin, when I got to my car, it was past 5:00 a.m.! I had been there for over two hours and had only gotten paid for one. But I knew that after not having an orgasm, Mike wasn't going to pay me double. So I drove home without protest (see what I mean about making exceptions for cuteness?).

Now, several days later, I find myself in an odd predicament. Throughout the session, Mike kept on telling me that he wanted to do this again, to which I agreed. I sent him a thank you email on Sunday, as I do for all my clients after our first session, but I haven't received a reply. Despite his bad behavior and the fact that he's kind of a cocky jerk, I think I've developed a sort of crush on Mike. It doesn't mean that I'd see him for free, but I think my feelings might get a little hurt if I never hear from him again.

Now, I'm left wondering how often this happens to other sex workers, or if this even happens at all. It just feels weird that I, a freaky fat queer sex worker, has a crush on a straight white frat-boy type. My only current thought is that the Universe really does have quite a sense of humor.