Chapter 3

I had plenty of time to rest and eat some lunch before Jenny showed up from work. She was a little bit tired, so we sat on the sofa in the family room to talk for a few minutes while she rested. For no reason other than just making conversation, I told her what had happened at Mrs. Jackson's house that morning. With practically anybody else, I would have been better off keeping my mouth shut about Mrs. Jackson and the fucking episode.

However, Jenny and I had always shared our secrets. I guess I had conveniently forgotten that Jenny had not told me about her fucking sessions before we started. I had to find out about those on my own, but it never bothered me. As it turned out, Jenny was not upset that I had fucked another woman, but she was very interested in the $100 tip that I had received.

"Dammit, Billy, I told you that you had a woman's dream between your legs. How do you feel about selling sex? You know, you could make a lot of money as a gigolo. Just think about those guys on the TV show that we've been watching. They talk about getting as much as several thousand dollars for a single date. I know that you could not make that much in this town for a single date, but, at your age, $50-$250 per date would not be bad. What do you think?"

"Oh, my God, Jenny, that would be a great way to make a living! Shit, I'd love to give it a try, but how would you feel?"

"I don't know for sure, Billy. I think I would be fine with it as long as you were getting paid. If you did it for free with another woman, I would probably get jealous, but I don't think a paying proposition would bother me in the least. Especially, if you let me be your agent. You could pick up the stray woman as you cut grass and probably do pretty well. On the other hand, I'll bet that I could drum up you a steady client list from the girls that come to the beauty salon where I work. Most of them would be high school girls who would be thrilled to be fucked by a professional. It sounds like great fun to me."

We talked about it some more and worked up a few ground rules. The two main rules were that the girls had to prove they were free from disease and they were protected from getting pregnant. They had to know, upfront, that I had no intention of marrying them or supporting a kid that was produced by our meeting. We figured that the best bet for our meeting would be at the girl's house. That way, if we were caught in the act, it would be apparent that the girl had made the arrangement.

Jenny said that she would start working on the deal tomorrow, but first, she was going to work up a form for the girl to sign to prove that she had solicited me, and not vice versa. I didn't think the paper would do much good if I got arrested, but it made Jenny happy so I went along with the deal. I was young enough to figure that I was going to live forever, so I was not worried about getting caught.

Once we had that thrashed out, Jenny and I adjourned to her bedroom. We normally fucked in some variation of the missionary position, but Jenny thought it would be a good idea for me to practice some of the other positions in case my customers wanted to give them a try. This time, she selected the doggie position. That was not my favorite position, but I went along with Jenny because she thought it was important.

I didn't like the doggie position because it was impossible for me to bump my partner's clit while we were fucking, and both Jenny and Mrs. Jackson had seemed to like that little extra something. I hope to come up with an alternative to the clit bumping, but I didn't know what it would be at the moment.

Nowadays, no foreplay was necessary with Jenny. She would start to drip from her cunt as soon as we started to walk toward her bedroom. Therefore, it was only necessary for us to remove each other's clothes, and to climb onto the bed. Hell, I didn't need the foreplay, because I was always ready to fuck!

Previously, when we used the doggie position, Jenny had always rested on her hands and knees. This time, she proposed that she rest on her shoulders and use a pillow for support. As soon as she assumed the position, I knew that I preferred this version because it made her cunt easier to get to.

I climbed on the bed and knee-walked up to Jenny's ass. I was already sticking straight out, so it was easy to slide my cock back and forth along Jenny's pussy slit. I got myself good and wet and lined up with her pussy hole. By this time, Jenny's cunt was loose enough for me to slide right in. I kind of missed having to work myself past those first muscles and stroking several times before I could bottom out, but I chalked this up to just one of those things.

I began a steady stroking rate, but there was something wrong. Jenny realized the problem first: I was not hitting her G-spot. I shifted position, and she tightened up a little more, and that combination put me in the right place. Neither one of us were really fans of the doggie position, and that problem with not hitting the G-spot was the reason.

I was about to come, but Jenny was still not ready. This was a totally unacceptable situation as far as I was concerned, so I wracked my brain for a solution to the problem. Suddenly, it dawned on me that all I had to do was reach around her thigh and diddle her clit with my fingers. I hardly had to touch her clit before she started coming. That triggered my release, so that, for practical purposes, we came together.

Both of us were happy that we had a solution to the problem, but it didn't do anything to increase our interest in the doggie position. Oh, well, I had a solution to an aggravating problem if the question came up. But honestly, I hoped that I would never be asked to perform in the doggie position. Unfortunately, we didn't have time for another fuck that afternoon, but Jenny had been relieved, and I always considered any fuck as a good fuck. Anyway, we were showered and dressed before our parents got home.

I now had an unexpected $100 that I had to deal with. I could not open a bank account on my own because any banking account for a person under 18 in our state required that a legal adult also be on the account. I did not want my parents to know about my new job, and they were the only adults I knew of to sign up with me. Until Jenny turned 18, it looks like the only choice I had was to hide the money. The only solution I could come up with at the moment was to stick the money between the pages of a book that I normally kept in my room. I hoped that was going to be good enough, but I hated to bet on it.

A few days later, Jenny had a customer for me. She was a high school senior who just could not connect with a boy. The girl had a serious acne problem that made her almost hideous to look at. She could cover most of her problem with heavy makeup, but that made her look like a tart. Despite all of this, she was a very nice and intelligent girl who was just stuck with the worst sort of luck. Alice Holbein was her name, and she was paying me $250 for the full treatment, including dinner and a movie. Thank God, she had a car so that we did not need a hotel room.

Fortunately, I did look several years older than my actual chronological age, so Alice did not have to be embarrassed to be seen with such a young boy. Of course, there was no alcohol involved, her parents insisted on that, but we went to a very nice Italian restaurant and then to a movie. After the movie, Alice drove us to one of the common high school make out spots. I had never been there, and Alice had not been there in some time, so this amounted to a new experience for both of us.

Like any sensible teens, we moved to the back seat before we did anything else. The weather was still quite warm, so that we were wearing light clothes without coats. That made things a lot easier, and Alice had pitched a couple of towels on the backseat of the car before she left home.