Kitty & Teddy, LLC Ch. 06a

Then came the KY. Jason put a cold dab right in the middle of the star. I could not help jerking. Mistress would have been very unhappy. The thought of a good lashing made me feel warm, in a conflicted sort of way. Jason just pressed gently til he penetrated my anus, while I tried to relax it. Once he was in, I pushed against the invasion. I had only served Mistress a couple of days, but I knew that much.

Like much of this whole process, Jason left me wanting more. His condom covered fingers caressed the wall of my colon. I did not get much from that, except one spot, which was very nice. When he pulled his fingers back and circled my open rim, that was a different story. I was just beginning to get off, when he stepped back and wrote down his notes. Next up was the search for my G spot. I was already dripping in anticipation.

The exploration of my pussy was just as orderly and clinical as the rest. Jason changed condoms, used more KY. Then, he had me lie back and hold my knees as closet my body as possible. This let him get a finger as deep as he could reach. Holy shit. He called it the A zone, clear in the back by the cervix. Now I understood Mistress' love affair with her foot long dildo.

Then Jason moved his fingers forward and scratched at the roof of my pussy. Holy shit, again. That was my G spot, and Jason said it was big and smooth, which meant I was really turned on. I could have told him that. Jason used the thumb of his other hand to press on my anus, while still scratching at the G spot, then gave my clit a flutter with his tongue, back and forth very fast.

I lost it. I screamed so hard I was hoarse afterward. I must have lost consciousness for a moment, because Jason was suddenly over at the closet, pulling toys out of a gym bag. He said that he had noticed something earlier, and wanted to try an experiment.

Should I be worried? I hoped so.

Jason:

When Cynthia asked me to show Tess the ropes, I did some looking around. You would be surprised what is available. In an ordinary bookstore I found a book with a checklist of erogenous zones. I figured that I could justify myself if I covered most of the things in the book. Plus, some of the places were new to me. For example, who thinks of wrists as a key erotic point? None of the call girls that trained me did. Yet, a little lick and nibble sent Tess right off.

I had to constantly remind myself to stop getting Tess worked up and get on with the list. It was not easy. Tess is a sexy girl, with all of the usual sensitivities. Like I had with her feet earlier, I had to move on before I, we, were really involved. It was a great way of building tension though.

A number of the erogenous zones are on the back. My favorites are at the top and bottom of the spine. Tess was a girl after my own heart. I told her that we needed to trade ass massages. Tess was perfectly willing, but, again, there was no time.

Given all the distractions, I did well to finish the checklist in an hour. I do not know how it was for Tess, but it was an experience I would not forget. It was stimulating, frustrating and oddly comforting. Then we moved on the main points.

Working closely with Justin, who is openly gay, I have learned a great deal about anal sex. I can find a prostate in just about any conditions. Women do not have prostates, as such, but there is supposed to be a sensitive area in the same place. Sure enough, Tess gave me a deep reaction only in one place. Her rim was another story, as it usually is. I was beginning to get a wicked idea.

Moving to the front, I changed gloves, and mapped out the vagina. Probing close to Tess cervix was entertaining, but not surprising. She reacted quite well to having her A zone stroked. I would have tried for penetration of the cervix, but she was still using the sponge. I may be many things, but stupid is hopefully not one of them. I needed to get this on the list. Giving a half-assed report to Cynthia struck me as really, really dumb. Still it could wait a bit, because Tess was really wired.

Just how wired became evident when I looked for the G spot. It can be very small and hard to find. Not then with Tess. Her G spot was a noticeable bump, nicely smooth. When I say noticeable, I could feel it, but Tess practically jerked sway. This was too good to pass up. I thumbed her asshole while stroking the G spotthen trilled her clit. Boom goes the dynamite.

I have had louder reactions, but not often, and those girls were screamers to start with. Tess is quiet as a mouse at a cat show. I was intensely flattered. I would have felt better, but I had an itch too, and it had not been scratched yet. Tess also passed out, which gave me a minute to collect my thoughts.

Stimulation and frustration seemed to be the theme for the evening, often as much for Tess as for me. Still, nothing lasts forever. We had reached the end of my list, but I wanted to try a couple of other things. This led me to my wicked idea. The best part is that I thought Tess would agree, even if I told her what I intended.

So I went and grabbed Big Johnson, one of those clear pick double dildos. When I turned back around, Tess was alert. She was also drumming her fingers on her pelvic ridge. It was one more thing to add to the notes. Then I told Tess my evil scheme, knowing she could not refuse.

"Tess, that is the end of my list. However, I noticed a couple of things that suggest a possible combination you would like." I held up the dildo. "This is what it looks like. It is designed to be, um, very filling, if you know what I mean. I want to fill your ass while I probe your front. Are you game?" At that point I held up two fingers.

Tess blushed when she saw the dildo, and kept getting redder as I went along. That did not stop her from agreeing. Oddly, considering my usual nature, I was completely serious about this one. I have heard, from several girls, that doing two guys at once makes both the front and back feel different. Tess had a sensitive spot in her colon and the bottom of her vagina, opposite her G spot, was also sensitive. That spot and the one in her colon were separated by only a thin wall of tissue. I wanted to stretch that tissue and see what her reaction was.

Tess:

Jason's idea made sense, which was a bit weird, because I did not expect it to. I would have done whatever he wanted, but I was interested in how this turned out, too. It was not going to be easy. The double dildo was easily as large as my wrist, and we needed it in my back side. I turned over and Jason worked my ass patiently. In less time than I thought possible, he was sliding that massive thing into my chute. Once he had it started, he kept twisting it back and forth as he worked it further in. That actually took longer than getting me open enough to accept it

Jason had not been kidding. I felt incredibly full. From the amount sticking out, Jason had managed to get at least a foot of it inside. All the twistings of the dildo had added another new experience to my list. As he had all along, Jason made dutiful notes on his pad. In spite of my huge orgasm, I was getting hot again.

While Jason was making notes, I had rolled over. Then, as I had done most of my life, my fingers started tapping on my bump. That felt really good too, though not different than usual. I looked up to see Jason staring at my hands. I blushed. After being naked with him for hours, that was embarrassing. I must be from another planet, like Miss Martel says.

I did not have time to worry about it, because Jason used yet another condom on his fingers, and was reaching for my cunt. This time, the palm was down instead of up. From the moment he touched my lips, it was different. When his fingers started sliding over the inside of my pussy, I knew why Jason had wanted to try this. I felt tight as a drum and his fingers made me vibrate. It made me want to melt.

I pulled Jason close and said, "Fuck me. Slow."

Jason:

Tess' reaction to the dildo was interesting, but not as interesting as her reaction to having it fed into her ass. As I expected, she was fairly relaxed, so getting Big Johnson started was not difficult. The problem was keeping him moving. Cunts are self lubricating, but asses are not. Rather than use massive amounts of Anal Eze, I took it slow, twisting Big Johnson back and forth, with constant inward pressure. Eventually I managed about ten inches to a foot. Tess seemed to enjoy the process, no doubt getting a lot of sensation from the twisting. It was also hot as hell to watch.

Once I had Big Johson in as far as I was willing to push, I rolled Tess over and gloved my fingers with another condom. I could tell right away that the experiment was a success. Tess twitched and quivered quite nicely when I ran my fingers up the bottom side of her cavity. Then something shocking happened. For the first time all evening, in fact the first time all week, Tess spoke without being asked. She asked me for a slow fuck

What could I say? In a way, it felt unfair, because she had had her itch scratched, quite spectacularly, while I was still frustrated. On the other hand, Mistress Cynthia would not take refusal kindly. The real clincher was the challenge. I do not know about what guys are like where you are from. In my part of southern California, the slow fuck is the standard of skill. I asked whether you were good enough to bring a girl, without pounding her. So, I reached for the condom box.

I have mentioned, several times, that call girls like variety from what their clients ask to do. One of the things call girls ask for is sex sitting up, rather than laying down. I have had sex on dining table chairs, secretary chairs, boxes in storage rooms, even a stack of Samsonite luggage (I made a mental note to introduce Wilma and Tess). For slow, comfortable sex nothing beats a skewered lap dance. It was time to make coffee.

Tess, as I had taught her, wanted to put the condom on herself. I was good with that. She threw in a twist, by sucking my balls, both at once. She did give Lil J a quick kiss, to lubricate the rubber. Once she had smoothed it on, I held out my hand. She looked puzzled when I pulled her to her feet, but that was cool. I took her to the desk, pulled out and reversed the chair and sat down. Tess' face showed understanding. She climbed on with no hesitation. Then came the lecture.

"Tess, you have chosen the ultimate position of control." Her eyes widened at that. Control is why so many call girls like the position. "The chair is against the desk, and will not move back. Cross your legs behind me and put your arms around my back. Good. Pull yourself forward with your legs. Excellent.

"Now, you have control. Everything, from here on, is at your pace, your discretion, your choice. If you want, you can hold me close and milk Lil J with your cunt muscles. They are plenty strong enough." As I hoped, she tried her cunt muscles then. Wowser. Lil J jumped to attention at her request. "You can push back and slide forward." Again she tried. Again, it was a good thing, but not what I was looking for. I wanted coffee, which meant we needed to grind.

"The other thing you can try is called "grinding." It involves rolling your pelvis forward and then rolling it back" Tess did not understand, but she kept trying things. Eventually, she hit the right combination, and I gasped. "Exactly that. Can you do it again?" Tess could not do it again on the first try, but she found it faster this time. "That was it again. Keep trying."

This time Tess knew what she had done, but she had not undone it. It took her a moment, but she drifted back far enough to try again. "Good. Now stop. Notice where you are positioned, then do the same thing backwards." This took longer. Eventually, Tess noticed she had undone her first move and did it again. Then she settled back and rolled again. "That's not quite it, but you are getting close. Do it again, aaahhhh, now undo it. Not quite. Do it. Now undo it. That was it. Now, aaahhh, keep it up. You set the pace, I am going to..."

Lil J popped his cork and I heaved up into her. Tess followed my orgasm with one of her own. We held each other close for a moment, then Tess bounced up and down as if to say "I did it", though she never said a word. The bouncing woke Lil J up. My orgasm had been nice, but not Earth shaking. The upside was, it looked like I was good for a double dip. Given the amount of foreplay, I should not have been surprised.

I calmed Tess down and we untangled. This was purely for clean up, because Lil J was already interested. I peeled of the old rubber and grabbed towel. I had intended to just wipe down and suit up, but Tess held out her hand. She wanted to wipe Lil J, so I handed the towel to her.

As hand jobs go, it was not much. However, it was a technique to remember, since Lil J was still very sensitive and the towel is rough. By the time Tess finished wiping him down, with a quick check of my balls, Lil J was up again. Tess gave him a nice wet kiss, and rolled on another raincoat. This time I grabbed a pillow to sit on.

As we were repositioning I said, "That was good, for starters. Now we can work on contractions. Start grinding again, only this time, pay attention to when you clench my cock and when you release. You can also change the pace, to draw things out."

Oops. I may have created a monster, right then. I could see the light go on in Tess' eyes, then a wicked look crossed her face. Oh shit. This was going to be a long ride.

Tess:

Getting fitted with that monster dildo was an experience. Once it was in, just moving around caused all sorts of sensations. When I told Jason I wanted as slow fuck, he looked conflicted. I could understand that. I had just gotten off, but he had not. Still, Jason was willing. He pulled me to my feet, though I had no idea why. When he pulled out a chair and sat down on the front edge, I understood. After a little positioning, we were settled. I was in Jason's lap with my arms and legs around him. It was very cozy.

I could see why this was good for a slow fuck. First, it was hard for either of us to move, particularly Jason. There was no way he could thrust. Second, it was comfortable. We could just sit, with me impaled, and neck if we wanted. Somewhere along the way, Jason mentioned that you could do this on the floor, but he would have to sit lotus style and his legs were not up for a long fuck. I put on my list of things to try. By then, Jason was ready to give his lecture.

I will not repeat it here, but I did my best to memorize it. This is a good thing. I have had many occasions to be grateful for the education. It came as a shock to find out, months later, that Mistress did not practice Jason's technique. Every time Jason and I met, for years after, we would try variations, even when I was very gravid.

The technique is very simple, though it was not obvious to me. I moved around, and eventually hit on one phase of it. As soon as I did, Jason brought it to my attention. After much more trial and error, I had the first half down. The second half did not take nearly as long, though we were interrupted by Jason having an orgasm. Fortunately, it was a small one.

I was so excited, I jumped up and down. This is not easy, when your legs are crossed behind another person's back. I managed, and managed to restart Jason's erection. At the time, it did not surprise me, since I was getting used to my own multiple orgasms. Now, I understand how unusual such things are for men.

In any event, Jason shot a wad, so we needed to change condoms. I had a vision of doing this bare. We could stay, linked up, and neck for a while, while Jason recovered. As I said, it was very cozy, and for once, I looked down on a tall guy. But, back to Jason.

When he shot off, Jason maintained a bit of an erection. My jumping had put some starch in what had been sagging. As I felt Jason's cock swell inside me, I felt a surge of power. I had not understood when Jason had talked about control. After the first orgasm, it made perfect sense. I decided to see how long I could make Jason go. Of course we could not, so we undid the snarl.

Jason walked over to the trash and peeled off the condom. Then he picked up a towel, but I wanted to do that. I held out my hand and Jason took the hint. It was very different from the other times I held his cock. The texture of the towel clearly stimulated him. That was another thing for my growing file of things to explore further.

With both of us now practiced, resuming the position did not take long. This time, Jason added a pillow, which made sense. I climbed on and settled in. It was amazing how quickly I had gotten used to having that huge dildo sticking a foot out of my ass, but bumping the chair a few times reminded me it was there. I was ready to go quickly, but I did not really want to. I wanted to build for a big climax, which suggested something. Since I had control, I could play a game with Jason.

The game was simple. If Jason loses interest, I lose and I need to apologize, probably with a blow job. If he came quickly, I lost again, but no apology needed. If I could keep him up, but not climaxed, we both won, provided he eventually finished. I set my target on five minutes. There was a clock by the bed, which I could see in the mirror.

Who knew sex was a competitive sport?

Jason:

It did not take a rocket scientist to figure out what Tess had in mind. As I said, she was in control and she clearly wanted to stretch out the process. Good enough. Under the circumstances, we were both ready for a long haul. My goal was to make her come first, but not too soon.

I had an advantage. I could see the bedside clock, but Tess had her back to it. I decided to let Tess have her way for a while, maybe four or five minutes, then I would do my best to bring her off. This, of course, was easier said than done. Big Johnson had made Tess' cunt the tightest I had ever been in. That was before Tess' pussy started milking me. Also, grinding is not difficult and Tess was mastering it quickly.

Tess may have anticipated me, or she could have come to the same place by a different route, or something else. For whatever reason, things started slowly. One minute went by easily. We were getting settled in. Tess was still trying to find a rhythm. I told her to consider timing her grinds with pussy clenches, to milk Lil J.

Minute two was spent on Tess trying to synchronize her pelvis and her pussy. At about a minute and 45 seconds, she hit one just right, which dragged a grunt out of me. First blood to the challenger. I may have said that out loud, because Tess smiled. It was a nice smile, but there was just a touch of in-your-face mixed in there. This was getting serious.

Minute three made me reconsider the serious part. Tess had seemed to be getting the rhythm down, when she stopped grinding. Instead, she concentrated on milking Lil J. This was nice, but I could do it for quite a while. We were almost to the start of minute four before it occurred to me that Tess might be going slow on purpose. Milking the clock, so to speak.

Almost spot on the top of minute four, Tess changed tactics again. This time, Tess dropped the milking and went with just grinding. There was not any doubt, now, that she was taking it slowly on purpose. Tess may be submissive, but she has a top-from-the-bottom streak.

Her change was so close to the minute that I wondered if I were speaking aloud. I have always talked to myself, and sometimes people have picked up on things I did not intend to say aloud. I would have to watch that. Then I found out I was wrong.

Almost exactly at four minutes, Tess started kissing me. She did not play around. This was some serious tongue diving, mixed with lips sucking and an occasional nibble. I have gotten girls to come doing nothing else. Two could play at that. My arms had been around Tess, but they were available to go elsewhere. I dropped them to her ass and gave a big squeeze. That got me a reaction, though Tess made no sound. More important it got me a moment to gather my defenses.