Chapter 11

I showed up for my appointment with Ruth Jackson the next morning right on time. It had been a couple of hours since my quickie with Jenny, so I felt ready and willing to give Ruth the royal fucking that she wanted and deserved. Ruth met me at the door wearing only a light robe which she shucked the moment the front door was closed. I picked it up for her and carried it into to bedroom where I dropped it on a convenient chair.

Ruth had become fond of disrobing me herself, so I stood beside the bed while she took care of that detail. She sat on the side of the bed as she remove my pants by pulling them to the floor for me to step out of. As had now become our custom, Ruth remained bending over and took my cock directly into her mouth. This was not a big deal: it was more like a kiss of greeting than a serious sex act. Ruth had no intention of giving me a blow job at that point; it was just something that she thought was fun. Hell, I was all for whatever she wanted to do: the woman was a paying customer!

Ruth held that position for only a few seconds; it was just long enough for her to feel me in full contact with her tongue. She pulled away and lay down on the bed on her back. "Billy, there is something that I want to try after our regular sex games, and I hope that you will like it."

"Ruth, I will like anything you want to do, you know that. Just tell me what you have in mind, and I will go along to the best of my ability." Ruth smiled at that statement, and I knew that I had a happy customer just waiting for my services to begin.

I lay down beside her and began our usual routine of French kissing and me playing with her tits and nipples. We had done this so often that she knew as well as I did what was coming next, and she could hardly wait. I kissed my way down her body until I reached her pussy, which she kept shaved for me strictly because I liked it that way. Ruth always shaved her pussy just minutes before our date, and it was always as smooth as the proverbial baby's ass when I got around to playing with it.

I placed a kiss on her slit, and I could already taste her pussy juices. I moved to between her spread legs and began licking her pussy lips. Ruth had already started to moan in anticipation of the pleasure that she knew was coming before my first lick. Eventually, I moved to her clit and caused her first orgasm of the day. I penetrated her cunt just as she came back to Earth, and began to stroke slowly at first, but I rapidly increased my speed to the rate that I knew was most pleasurable to Ruth.

Ruth had her customary two orgasms before I came just at the end of her second come. I had learned to time that almost exactly because that was the way she enjoyed it the most. We stayed in contact as my cock began to go limp. I don't know exactly how that felt to Ruth, but she certainly seemed to enjoy the sensations that produced. I rolled off her, and we rested a few minutes.

I always had to fight the tendency of my cock to swell during that time because I knew what was coming. Once she had recovered enough strength, Ruth moved so that she could take my flaccid cock into her mouth. Apparently, she liked the taste of our combined juices because she carefully used her mouth to clean me before continuing on into a full blow job which she sustained until I came again.

All of this was the result of a steady learning process that grew from our first encounter. We would often laugh at how we had progressed to our current state of affairs with our routine being so much different from where it had started. Such a light conversation was going on now, but Ruth caught me by surprise when she said that now was when she was ready to tell me of her next experiment.

"Billy, what do you know about anal sex?"

"Not very much beyond what I have seen on the internet. Truthfully, it never appealed to me, and the subject has never come up during one of my dates. Why do you ask?"

"I was talking to one of the girls recently, and she said how much she enjoyed it. She praised it so much that I have been thinking about trying it for several days. Do you think that you could give it a try for me to see if I like it."

"Okay, I'll give it a shot since you specifically asked for it, but I do want to take a shower the moment we finish. Will you agree to that?"

"Sure, I may even join you in the shower." With that, Ruth moved to her hands and knees in what looked like the classic doggie position. Her anus was deeply recessed between her ass cheeks, and it looked like I was going to have a problem reaching it. I had Ruth lower her shoulders to the mattress, and that did give me a better angle, but it still didn't do what I wanted.

I complained that I still could not reach her for more than an inch or so of penetration, but I had an idea. "Roll over onto your back and pull your legs up to your ears, or as close as you can come to that. I know what it can do for normal fucking in that position, and it might work for what you want."

We fiddled around a little bit and wound up putting a pillow under the small of Ruth's back to get the best possible angle. This combination did put her anus into a much better angle for me, so I liberally coated my cock and her asshole with the KY Jelly that Ruth had provided. I got into position and pushed my cock head against her anus, but I could not get enough pressure to force my way in. I told Ruth that she had to relax more and not tense up until I had penetrated her. We tried again, but to no avail.

Then I remembered something that I had seen on the internet. I called a halt long enough for me to fetch another towel to use to clean up afterward. When I got back, I coated the first finger of my left hand with KY and used that to force penetration. I managed to get my finger in, but Ruth found it to be quite painful. "Ruth, if one of my fingers hurts, imagine how much more pain there will be with my cock in there."

"Okay, you have a point. Keep on with your finger, and let me see if I can relax enough for it to quit hurting. We will need at least two fingers, though, to come close to the size of your cock."

I resumed with moving my finger around her anus and into her colon past the sphincter in a kind of finger-fucking motion. I used up nearly half a tube of KY before Ruth called a halt to the effort. "Dammit, no matter what you did, it still hurt with just that one finger. I guess that I will just have to give up on anal sex. But, now that I am in this position, do you think that I could have one more regular fuck?"

Man, was I relieved that was over! In answer, I wiped off my cock as best I could and moved up to align with her pussy hole. This time, I slipped right in without any hangup, and I started the fuck without a pause. Ruth was still holding her knees up around her ears, so I had to hold my body almost horizontally to give her the full fucking stroke. Even at this unaccustomed angle, I still rubbed against her G-spot, but I couldn't quite reach to bump her clit with my pubic bone.

By this many fucks, I was in no hurry to come, so I was able to pump Ruth through two more orgasms before I came. This time, my jets were pretty damned weak, but she did feel the jizz entering her tunnel, so she even had a very minor orgasm when I finally came. This was more orgasms that Ruth was used to in one session, so she decided that she was adequately compensated for not getting her anal sex that she had so anticipated. Personally, I was happy to give her the extra regular fucks to be able to avoid the anal sex. I was going to have Jenny add a clause to the contract forbidding anal sex from now on.

We were resting after the last fuck when I asked Ruth about changing our schedule to evening visits. I explained my reason for the change, and she readily agreed to giving it a try. Anything was better than giving me up and missing those wonderful orgasms that I caused. I did tell her that the new schedule would not start until school began in a few weeks.

All of my older clients were willing to make the change in schedule. In fact, some of them actually preferred the change. One woman could not make the change because her husband was home every night, so I offered a ruse to get around him. I suggested that she tell him of arranging a "night out with the girls" for the days when we normally met, and she could pick me up in her car. We could go to one of the regular teen parking spots, and I could fuck her there. She found that to be a thrilling alternative to sex in bed, and that's what we agreed to try.