Chapter 6

"Mrs. Arthur, I would make you a special case if that ever became necessary. However, I wonder exactly how much accurate information you got from Mrs. Jackson. Did she tell you about my new profession?"

"No, I don't recall Ruth making any sort of comment along that line. What do you mean?"

"Well, I guess you know that it is the ambition of every kid my age to own a set of wheels. I think it is obvious to anybody who gives serious consideration to the question that there is no way that I earn enough money mowing lawns ever to be able to afford a car, even a used one. Therefore, I have decided to branch out and to offer my services as a gigolo in order to raise enough money to be able to buy a decent car.

"I have already earned around $1000, and I hope to have enough money to afford a car before the bad weather of winter sets in. My current feeling is that I will charge a flat $250 for half a day of my undivided attention. I have had a very good teacher, and I am sure that I can give any woman the treat of her life. In other words, as long as it is not painful to either side or harmful to either side, I offer my services for half a day for $250, and I will attempt to do anything that my client requests within the previously stated parameters.

"Notice that the $250 rate is for a one-shot appearance. If the client wants more than a single visit with me, then I will reduce the rate to $200. That's the way things stand at the moment; would you like for me to add you to my client list? If you should decide that you want to go the $250 route, but decide later that you would like to become one of my regulars, then I would be willing to refund $50.

"How does that sound to you, Mrs. Arthur? Would you like to try me out to see if I am really worth that much money? I assure you that I am, but I can make adjustments to fit my clients desires."

"Frankly, Billy, I had no idea that you were prostituting yourself. On the other hand, with inflation being what it is, I can understand why you are doing it. Never before in my life have I ever hired a gigolo, so I really don't know what to expect from you if I do hire you."

"Well, Mrs. Arthur, I have been told that I should never give free samples, so the question really is whether or not you trust the word of Mrs. Jackson as to the quality of my services. I promise you that you will not be disappointed, but you only have my word and the word of a very satisfied customer. What else can I say?

"This morning is half gone and I have a commitment for this afternoon, so tomorrow would be the earliest that I could show up to service your needs. Perhaps you would like to think about the situation for a while before committing yourself. If so, that is fine with me. You have my telephone number, so you can call me for an appointment whenever you make up your mind. All I ask is that you do not say anything about this new career to my parents."

"Okay, Billy. I'll give your proposition some thought and let you know my decision. I hope you realize that $200 or $250 is a big wad of money for a widow to shell out for a few hours of sex. I am interested based on what Ruth had to say, but I will have to think about it. I will telephone you if I decide to take you up on your offer."

Jenny and I had our usual very pleasurable tumble that afternoon when she got home from work. For some reason, Jenny wanted the reverse cowgirl position, and I never argued with Jenny when it came to sex. That is not one of my favorite positions, but I agreed wholeheartedly with Jenny that I needed to become an expert with it. With one thing and another, we only had time enough for two rounds of reverse cowgirl before we had to shower to get ready for our parents coming home.

After we got dressed, we stayed in my bedroom and discussed business. Jenny now had three commitments for the evenings next week, so things were really looking good for our business. That's when I put my foot in it! I told Jenny about my conversation with Helen Arthur, and Jenny hit the ceiling, "Billy, you have got to stop making commitments like that! You could get into serious trouble if one of those women complained to the cops. If she had not filled out one of those forms I wrote up, she could charge you with soliciting her for prostitution.

"Things are entirely different with you and the high school girls versus you and these older women. Our tie up with Janice Upton will probably be all the protection we need from that side, but these older women don't have a reputation they would want to protect, if one of them really got pissed off at you. If Helen Arthur calls for an appointment for your services, be damned sure you don't commit to anything until after she has talked to me. Furthermore, the next time Ruth Jackson propositions you, make sure she talks to me before you agree to anything. We have got to protect our asses! I am just about old enough to be tried as an adult, so that I could spend some real time in jail.

"At least with you, you are still a juvenile as far as the court system is concerned, and you would probably not spend any time in jail, but we would all have to move out of this town if the word got out that you were a gigolo. I commend your entrepreneurial spirit, but, dammit, you have got to learn to protect all of our asses. Just one slip could get us into a world of trouble!"

Thank God our parents selected that moment to show up and to call for us. That forced the end of the conversation, and I was glad for the relief. We went downstairs and Jenny managed to cool off before we ran into our folks, so the secret was still safe for a while.

Three dates next week would amount to $675 toward a set of wheels for me, and how else could I possibly hope to earn so much money doing something that I enjoyed so much? At the rate I was going, it was quite possible that I could have enough money to afford a good car long before I could legally drive it. Man, it was going to be hard to sit on the money for several months. Maybe I could arrange for Jenny to buy the vehicle and be the official owner while I drove it with a learner's permit. That could get pretty complicated, but maybe we could work something out.

Mrs. Helen Arthur did not take long to come around, if you will pardon the weak pun. A couple of days after I talked to her, Helen telephoned Jenny at the beauty parlor to find out how to make an appointment with me. Jenny quoted her a price of $250, but with the rebate if she became a steady customer, and Helen stopped by to sign the hastily revised form that Jenny had come up with. Therefore, at 9:00 AM on the following Thursday morning, I showed up at Helen's house ready to take on my first senior customer arranged through Jenny.

Of course, I had bathed and was dressed in my usual "non-working" summer attire. I rang the doorbell precisely at 9:00 AM and Helen opened the door so quickly that I thought that she must have been standing by the door waiting for me. She was wearing a sundress and nondescript house shoes, but her hair was fixed nicely and she was wearing some makeup, so she was pleasant to look at. She had already paid Jenny the $250 fee, so there was nothing left to slow me down.

I was a little taller than Helen, and I had no trouble gathering her into my arms for a kiss. She was a little surprised at my action, but was in no way reluctant to move into the spirit of the game. Helen returned my kiss, and we shifted into a French kiss before breaking contact. I could tell that Helen was a bit nervous, and I was not surprised, because this was her first experience with a gigolo.

I took her hand and led her to the sofa where we both sat down very close together. My recent visits to the back seat of cars with a girl had given me plenty of experience to follow through with Helen. I simply treated her as another one of my high school "dates." I put my arm over her shoulders and drew her close for another kiss. This seemed to fit with what she expected, and she melted into my arms as if we were long-lost lovers.

I held her and kissed her for a few minutes without making any other moves. However, before long, Helen had taken my hand and placed it against her breast. That was when I discovered that she was not wearing a bra. It was easy to rub the palm of my hand over her projecting nipple as I gently massaged her tit with my fingers and thumb. This went on for a few minutes until Helen decided to stand up.