The judge stared down at the defendant, a look of genuine concern on his face. “Ms. Hudspeth, before I pass sentence, I want to know what arrangements you have made for your son, Gregory.”

The defendant looked sweetly at the judge, twirled her hair, and tried to be as appealing as possible in an orange jumpsuit. “Well, your honor, he turned eighteen today, so fuck him.”

That’s me, Gregory Hudspeth. Or, Greg to my friends, G-Man to my really good friends, and G-Spot to my girlfriend.

For my eighteenth birthday my mother gave me the best present ever. She went to jail for four years. Sure, she had been arrested before. Prostitution, drug possession, shoplifting, that kind of thing. But never more than a few days of jail at a time. This time she tried to diversify her revenue streams by selling coke to an undercover vice cop.

Nobody knew where my father was. In fact, nobody knew who my father was. I’d gotten used to it. Now that I was on my own, it was time to celebrate.

Dear old mom kept many bottles of cheap vodka at home. I’d developed a taste for it. She couldn’t track how many bottles there were from day to day, let alone how full they had been. Most of the time she was high, or drunk, or preoccupied with fucking the latest “date.” Being hung over most days, I’d barely made it through my last year of high school. But I graduated yesterday, and today I turned eighteen. And Mommy Dearest was out of my life.

When I got home from court (I had gone to make sure mom didn’t escape) I called Christine, my high school girlfriend. We had been “doing it” for almost three years now. She was more than ready to help me celebrate.

The five-foot-six redhead knocked on the door. When I answered she just said, “Nice.” I supposed my being naked with a hard-on might have had something to do with that.

She came in and I nearly dragged her to the bedroom. I clawed at her clothes until those that weren’t in shreds on the floor were in tatters on her body. Christine shirked out of those and climbed on top of me. I was fumbling at my night stand for a condom, and she brought my hands back to the bed.

“You won’t need a condom just yet.” I wondered what Christine had in mind. She wasn’t trying to get pregnant, was she? “There are a few things I want to experiment with, starting now.” Christine wrapped her right hand around my dick and began slowly rubbing her hand up and down. Her left hand was lightly tracing circles on my chest, stopping to tease and twist my nipples every few seconds.

“Such as what?” I asked. I wasn’t afraid of her experimenting – sounded like fun – but I’d like to participate in the anticipation.

“Such as what I’m doing now. I want to watch you cum. Put your hands behind your head.” She was nothing if not direct. I complied. She was also keeping me on edge. I would come close to the cliff, then she would slow down and let me pull back. I needed to cum, and wasn’t sure just how long I would be able to hold out.

Her right hand left my dick to play with my balls, then traced a line back to my hole, drawing slow circles around it before plunging in. Her left hand wandered from one cinnamon nipple to the next, tweaking and occasionally twisting. I tried reaching for her tits, but she slapped my hand away. “I’m in charge and this is my experience,” she said. Yes, Ma’am

With my hands behind my head again, one hand found my cock and the other stroked my neck and my chin, then slowly outlined by lips. I let my tongue lick her fingers, then suck on them. She leaned forward and her tongue replaced her fingers, her tongue probing at my lips. I opened my mouth and her tongue entered to pillage my mouth. I begged her to slow down on my pole since I was near the edge. I was also near screaming.

“Do you need to cum?” she asked. I shouted my answer. “Not yet, I’m enjoying this too much.” Christine was really into this experiment. I could only imagine what the next one would be like.

She sped up her stroking on my man meat, and shifted her weight until she was pressing lightly on my balls. I was in agony and ecstasy at the same time. Her tongue left my mouth, then she sat straight up and squeezed the head of my dick.

She moaned and I shrieked.

My balls pumped out a small lake of cum, which exited my rod in streamers of white. Some landed on my stomach, some on her face, some on her tits, and some on my face. I was totally spent. Christine leaned forward once more and kissed me.

“What’s next on the agenda?” I asked her.

“I want to add a third person to our sex.” I had never seen this side of Christine, and I liked it. “I don’t have anybody in mind yet, and I’m open to suggestions.” That sounded wonderful, so I tried to give her a few names of girls I’d wanted to fuck. “That’s suggestions only. I’ll decide who the third person is going to be.” This side of my girlfriend was going to be stupendous.

After a few minutes we got out of bed and went into the kitchen. We scarfed down what food was in the refrigerator, then hit the vodka. “You’ll have to buy more groceries tomorrow,” she noticed. Oh, shit. Using what for money?

“Christine, I have only a few hundred dollars that my mother didn’t steal out of what grandma left me. It’s not enough for next month’s rent, utilities and car insurance, let alone groceries and gas.” I hadn’t thought of this part of being free.

“Then let’s find you a job.” Christine was always the practical one.

We went to seven on-line job boards. I didn’t have an engineering or math degree (shit, I didn’t have any degree), so I didn’t qualify for most of them. “Let’s try Craigslist,” she suggested.

After about fifteen minutes I was really discouraged. I could make minimum wage cutting grass or stocking shelves, but I couldn’t live on that. “OK, let’s try Backpage.” Never heard of it and told her so.

“Backpage has fewer jobs than Craigslist but, uhm, more that don’t require a degree or academic skills.” Christine looked like she was about to blush.

Backpage it was. The usual jobs were the usual minimum wage, doing shit I didn’t want to do. “Try the adult jobs,” she suggested. I did. God, I wish I had born with a vagina.

Most of the jobs were for female “models,” online “adult actresses,” and nude dancers. No good. I eventually figured out how to filter the results, and found six jobs for males. Two were for gay porn actors (no, thanks) three I couldn’t understand, and one was for a party entertainer. It paid $50 an hour. Party entertainer it was.

Instead of a phone number the ad listed a Skype address. I called it up and sent a contact request referencing the ad. I turned to Christine and we started kissing. I got my hopes up for more sex, and then my Skype account chimed.

The contact request was accepted by somebody named JSD followed by a bunch of numbers. Immediately I had a video call from him. Of course I answered.

The guy looked really old, about thirty or so. He had a thin face and an even thinner beard. “You don’t look old enough to be a G-Man,” he said. “Most federal agents are a LOT older.”

He got me laughing. “No, I’m not a federal agent, that’s my nickname. What’s your name?” I asked him.

“I’m Jake. So, you’re interested in the job, right?” I nodded.

“You know it’s for a party entertainer, right?” I nodded again.

“So, who is that behind you and why are you both bare-chested?” Oops, I forgot Christine was behind me. I motioned her to move away from the camera.

“That’s my girlfriend. We’re bare-chested because we were, ah, you know, in the bedroom.” I actually blushed.

Jake took it in stride. “Stand up,” he told me. I glanced down at the slowly diminishing bulge in my boxer briefs, and figured what the fuck. I stood up.

“Skin-tight white boxer briefs. Good. Be sure to wear them tomorrow. Show up at nine p.m. and be prepared to stay for four hours. That’s $50 an hour, or $200. And, you also might get some tips.” This sounded like the perfect job. He sent me an IM with the address. Good, it was less than five blocks away.

“Is this just a one-night job?” I asked. I needed to find something closer to permanent in order to stay in the apartment.

“For now, yes,” Jake answered. “Depending on how you do, there could be a lot more work.”

“I’m not gonna blow it,” I assured him.

“That’s a shame,” Jake replied, then he signed off.