Chapter 8

On Saturday, I was able to relax and enjoy my work. I was scheduled to give the combo treatment to four teachers, one of whom was my homeroom teacher from last year at the middle school. I had already shaved her and rinsed her pussy thoroughly in preparation for the cunnilingus. We had reached the bedroom when she started to giggle. I asked her what was funny, and she said, “I just had a thought. Bill, what does it feel like to fuck a teacher?”

That question caught me flatfooted. “I have never thought about it, but I can see the humor in the thought. Actually, what I really think about is how much I am going to enjoy a fuck with an adult woman who knows what she wants and can appreciate it when I do a good job. I don’t think about her being a teacher because I want to concentrate on giving my best to the fuck. When I’m here at Jane’s Pleasure Palace, it’s my job to make the woman feel like she has had my best effort and enjoyed something special.

“Believe it or not, I enjoy a good fuck as much as the woman does. If the woman is not satisfied, then I won’t be satisfied, and that would make me feel let down. Does that answer your question?”

“How does that differ from servicing teenaged girls?”

“It is quite different. When fucking a teen, I have to be sure that she gets everything she was looking for, and that can be very difficult because the girl may not know what to expect. That means that I have to work extra hard to overcome any reservations she has about sex while still making the experience physically satisfying to her. So far, I have been successful, but who knows when I will fail.

“That is another advantage to working with adult women. They know that every sexual encounter will not be successful, but they can be realistic about it. They will accept the refund of the money they paid and come back later for another try. Who knows what a teenager will do? That is one of the things that concerns me about sex with teens.

“Now, I have a tight schedule for today, so I would like to get on with the cunnilingus. I know that this is my first time with you for cunnilingus, but it would help if you would tell me if you have done it before and how it turned out.”

“I am a virgin with cunnilingus, so you will have to tell me what to do.”

“Okay, just lie back in the missionary position and spread your legs. I will do the rest.”

What the hell, I smelled a hint of strawberry. Did this woman use a strawberry-flavored douche before showing up here this morning. If so, I appreciated her concern for me. I don’t know whether or not to mention it. I’ll just wait to see what happens later.

I went through my usual routine for cunnilingus because I wanted to break my customer in easily and make her want a repeat performance. When that happens, I might make some minor changes, but today I will stick to the tried and true. She came twice during my treatment, and I remembered from the last time I fucked her that she was very responsive. That made me wonder if I was the one who caused these responses, or would any man achieve the same results. I certainly was not going to ask.

The cunnilingus experience was so intense that she fainted at the end of her second orgasm. However, she did wake up in about 15 minutes, so my schedule was not harmed. Her comment when she woke up was, “My God, Bill, I had no idea that cunnilingus could be like that. You have just won a convert and a regular customer.”

“Thank you for the vote of confidence. I will look forward to my next opportunity to satisfy you. Now, are you ready for the final act in our three-act play of pleasure?”

She giggled at that and told me to do my regular magic. I guess I did, because she had three orgasms—the most that she had ever had at one session of sex with me or any other man. We speculated that the cunnilingus might have made that possible. I didn’t say so, but I really didn’t believe that. Nevertheless, she said that she would be back again soon for another combo session. Fine, that was a very pleasurable way for me to bring in $350.

I left her to sleep some more while I worked on the next combo client. She was kind of wary because this was her first visit to Jane’s Pleasure Palace and had been talked into the visit by a friend who was a regular customer. This woman was no virgin, but this was her first contact with a professional gigolo, which I considered myself to be. Sue always interviewed the first-timers, so I had some idea of what the woman really wanted.

She was a widow and a single parent of a 7-year-old girl. They were living on a combination of insurance money, investments, and her salary. Today, the child was being cared for by a grandmother, so the child was no problem. My thought was that if I worked it right, I might pick up the grandmother, the mother, and the child when she was old enough as regular customers. I certainly was going to try.

The first stage was the shaving. The woman was not so sure that she wanted that, but I pointed out that shaving was a requirement for cunnilingus, so she gave in. Her curiosity about cunnilingus overcame any reservations she had about being shaved.

The shaving was a bit more than routine because the woman had never shaved her pubic area, and it was a mass of hair. I first had to clip away a lot of hair with scissors before I had any hope of using the razor. She was embarrassed at being nude with me, especially since I was sporting an erection that was impossible to ignore. She kept staring at it, but I paid no attention to her doing that.

The orgasm from the finger-fuck during the shaving of her pussy was spectacular. I wondered if she had ever been finger-fucked before. She fainted for almost 15 minutes, and I was tempted to splash her face with water to bring her around. That was not necessary, but it resulted in a radical change in attitude. Apparently, that orgasm was so strong that it made her want more of them and want them immediately. Now, she was fun to work with and not a pain.

I got her dried off and she dried me off, spending considerable time on my cock. I could tell that she was experiencing an epiphany, and I didn’t want to mess that up, so I was very patient with her. I led her to the bedroom and started on the cunnilingus as quickly as possible. Oh, my God! I had not noticed in the shower, but this woman was a squirter. She squirted me in the mouth and on the chin during her first orgasm on the bed, and she did that again during her next two orgasms. Where did all of that fluid come from. It was obviously not urine, so I did not complain, but she was the first squirter that I had ever encountered.

The fucking caused her to squirt both times she climaxed while being fucked, and she completely collapsed at the end of the last orgasm. It was especially intense; I assumed that was because I came at the same time. Oh, well, I would just report the squirting to the housekeeper, and she would take care of the residue. Meanwhile, I would use a different bedroom for this afternoon’s action.

I left her for lunch after she slept for about 20 minutes. She had been told what to do when she woke up from her last orgasm, so I didn’t worry about her. I did check on her after I had finished eating lunch, and she was just waking up. I helped her out of bed, and she said, “I have never had an experience like that. I can hardly wait to tell my mother about it. We will both be here as soon as we can schedule another visit.” I thanked her and left her because it was time for me to greet my next customer.

This person was a real surprise because she was the principal of my high school. She greeted me with a grin as big as I could imagine. “Hello, Bill, I’ll bet that you are surprised to see me here. I’ve heard so much about your prowess with sex from several of the teachers that I had to come by to try you out. I just hope that you can live up to your reputation.”

“Well, Mrs. Gibbs, I will do my best not to disappoint you.” I had become something of a speed-reader, so it took me only seconds to learn all I needed to know about the sex history of my high school principal from Sue’s report. I set it aside and got to work. My cock had sagged a little bit from my initial surprise, but it was returning to full hardness as we spoke.