Chapter 7

My next customer was a high school girl named Roberta Wilson. I knew nothing about her, and Jenny showed me her picture so that I would have a reasonable idea of who I was fucking. Like both of the others so far, she had popped for the $250 ride with me. All three girls wanted a sampler before they signed up for a long-term contract, and I did not blame them. Roberta was the third daughter of the richest banker in town, and had no trouble affording the $250 charge.

Roberta too was scheduled to pick me up at 6:30 that evening, and I was ready when she showed up. As with the other two girls, Roberta had her own car, and that made things a bit easier for both of us. We went to dinner in a small Greek restaurant where Roberta drank a little too much ouzo wine. Since she was driving, we had to wait until she had consumed enough coffee to get rid of the tipsiness so that she could drive. That made it impossible for us to take in a movie, but I certainly didn't care, and I doubt that Roberta cared either.

Anyway, once we felt that it was safe for her to drive, Roberta drove us to one of the usual high school parking spots reserved for heavy dates. For what it was worth, I was getting an education in the available make-out spots, and I was filing the information away in my memory for later reference. This was certainly one of the things I needed to know about when I started to do the driving.

Skipping the movie had made us a little early for the usual parking routine, and we were the first ones to arrive. Roberta selected a choice spot and pulled in. We were isolated from anyone else by tall bushes to our sides and front. It would have taken some real effort for someone to get a look at what was going on inside our car, and neither one of us expected that to become a problem. We moved to the back seat and settled in for a few hours of fun and games.

By being early, the pressure to hurry along was removed, and I planned to take advantage of that. We started out with the usual French kissing and had all of our clothes removed in reasonably short order. Roberta's boobs were larger than I was used to seeing, and I set out to find out if the difference in size made any difference in the way I should treat them. I had progressed from French kissing to nibbling on her earlobes and taking little kisses on the side of her neck.

While doing this, I had placed my right hand over her left tit and was rubbing the palm of my hand on her bare nipple while performing a gentle massage on her tit with the fingers and thumb of that hand. This was pretty much what I had done with my other dates, and Roberta responded the same way the other females had. Namely, she loved the feeling I was giving her and had started to moan in her appreciation. That made me feel good and also verified that my general technique was valid for any size boob.

To carry my experimenting even farther, I moved my lips to her unoccupied nipple. At first, I sucked gently on her right nipple as I played with her left tit and nipple with my right hand. However, I wanted to make sure that I did not make either nipple sore, so I switched back and forth between the two. This was going well, and Roberta had increased the volume of her moans and added a few sighs to the mix. Jenny had clued me in on some of the other things that girls liked for a date to do to her nipples.

With that in mind, I gently pushed Roberta back until she was lying on the seat with her nipples pointing more or less straight up. I continued the playing and kissing for a few more minutes and then tried one of Jenny's suggestions. I began to flog her nipple with my tongue; that was not as easy as it sounds, but I kept at it, and finally made it work. Meanwhile, Roberta was carrying on something fierce with her moans and sighs, and that encouraged me to extend my efforts.

My tongue was about to give out from the flogging I was doing, so I pulled my tongue back out of the way and gently bit down on Roberta's nipple. I bit hard enough so that there would be no doubt what I was doing, but I was very careful not to bite hard enough to cause her any real pain. That broke her string of moans and sighs and caused her to emit a little scream of surprise and delight. On top of that, she began to bounce her hips very vigorously, and I realized that she was having an orgasm as a result of me playing with her nipples. That was another very good piece of information to file away in my memory as another way to cause an orgasm.

Once Roberta had completed her orgasm, she grabbed me by the ears and pulled me up enough for an extended French kiss. She then announced, "Dammit, that was the first time I ever had a come just from a man playing with my nipples. I didn't even know that it was possible, but, Billy, you really hit the spot. Do you think that you could do that again?"

"Gee, Roberta, I don't know for sure, but I don't see why not. Do you want me to try again right now, or do you want to continue on with what else I had planned for the night?"

"I guess you are on a roll right now, so I would like to see what else you could do for me. Maybe we could come back to the titty play later if it seems like a good idea."

Well, that was a pretty positive statement as to what she wanted, so I moved as far as I could toward her feet and leaned down to kiss her pussy. I had heard from Jenny that almost every girl wanted to feel cunnilingus at least once, and Jenny agreed with me that most girls would probably appreciate the feelings of cunnilingus before they were fucked, rather than afterwards. Roberta seemed surprised that I was going to touch her pussy with my mouth, but she certainly had no objection.

Roberta's inner pussy lips were rather prominent in the way they stuck out past her outer labia, and that meant that I was going to have to improvise over my usual routine that I had learned from Jenny. What I did was simply to lick first one of her outer lips with my tongue and then lick the other one. This was fairly simple to do, since I was able to push her inner lips out of the way as I licked. It took no more than three licks for her to join in the spirit of the adventure. At first, she giggled a little bit, but I ignored that. By the fifth lick, Roberta was back to moaning and sighing.

At that point, I switched to concentrating on her inner pussy lips, and that nearly drove her wild! She was back to bouncing her hips, and that made it impossible to remain in contact with her pussy. I held her hips down with my hands and used my thumbs to hold her pussy slit open so that I could easily reach far down into the slot. This certainly did something for Roberta, and she began to bounce her hips so vigorously that I simply could not hold them steady. Of necessity, that ended the cunnilingus session, but Roberta was completely satisfied with what she had experienced so far.

By this time, Roberta had enough foreplay that she was well lubricated and in no danger from being injured when I penetrated her with my cock. Roberta made no effort to conceal the fact that she was ready for fucking. She kept urging me to insert my cock. The few seconds it took for me to get lined up with her hole was spent by Roberta in saying, "Fuck me! Fuck me! Fuck me!" If that wasn't a clear invitation, I never heard one!

I was circumcised, and I had no idea whether or not that made any difference in the speed at which I could penetrate a woman. I have my doubts on the subject, but I never heard any real complaints from my customers about how slow I was to penetrate them. Nevertheless, Roberta grabbed my cock with her right hand and use the fingers of her left hand to spread her pussy lips. She had me lined up in a very short time and began to chant, "Push it in! Push it in! Push it in!"

Well, I guess I am used to taking orders from women, so I began to push as soon as I felt myself come into alignment with Roberta's cunt. I knew that she was not a virgin, so I did not expect a very tight vagina. However, her cunt was much looser than I expected, so I had to move around and experiment a little bit to make sure that I was lined up to rub against her G-spot. As I said before, I take pride in rubbing against a customer's G-spot, so I made certain that I found Roberta's.