Kitty & Teddy, LLC Ch. 06a

Jason started by kissing my bump. I do not know the proper word, but it is the area that used to have a lot of hair. Jason's dry lips kissed that and slowly worked down to the top of my cleft. There was no tongue, even when he reached my clit. Instead, he did his best vacuum cleaner impression. It was very different from the sensations I usually had had in that area. I was so primed I felt I could scream. Jason must have felt the same.

He said, "This is where it gets real for me. Up to now, it has been foreplay. Now we get to bump little heads. I know you like it rough, but I want you to pay attention to me as we fuck. You ought to be seriously tight, but I want you to clamp down on my dick as I start to withdraw. Are you ready?"I was so ready I may have cried.

It did not happen right away. Jason grabbed two pillows, which he put under my ass. Then he spent a moment getting his own position perfect. I wanted his cock so badly, but something in my mind told me that this was a professional at work. He stuck just the tip of his cock in. When he pulled it out, I was just short of screaming. Then he put the head of his cock at the very bottom of my cunt and pulled it up between the lips. When it hit my clit, I whimpered like a puppy. Jason took his time lining up the next move. I could tell he was going in deep on the first thrust, except that he did not. Instead, Jason slapped his forehead and started saying "Fuck" over and over again.

What had I done wrong? Was I not good enough, for some reason? I was starting to cry, when I saw Jason stare at the bed beside me. There, on the top of the sheet, was the contraceptive sponge. We had never gotten around to using it. Oh God, not again. I tried laughing and crying at the same time. It did not work, but at least Jason looked sympathetic. Jason's cock did not.

Then Jason did something I will love forever. He smiled at me. He picked up the box of condoms and he smiled, as if to say that he knew what to do. Then the smile turned a little wicked, as if he was looking forward to doing it, and I got warm all over.

Jason pulled one condom out of the box and started to lecture. I am sure it would have been informative, but I only caught the part about using his cock and balls to move him around. That I could do. Jason cut off in mid sentence, but I was already going to my knees. Two nights before I had given him a blow job. That was then. This was different. Jason was already very ready, I could use my hands and Mistress had had me studying online. I had no more experience, but at least I knew what I wanted to do.

I took as much of him into my mouth as I could, and slowly pulled back, while sucking as hard as I could. At the same time, I used one hand to keep Jason from moving, and the other one on his balls. Jason shuddered for me, which gave me an unbelievable sense of power. I caught a deep breath and went for another long pull. This time I ran my thumbnail from his scrotum up the bottom up his shaft. Jason was gasping for air. This one would do it. Trying not to think about it, I took Jason's cock all the way in and on past my throat. My hand had a hold of his scrotal sack and tugged a little while squeezing the balls, just a little. Jason exploded.

The sensation was like nothing I ever felt. Jason's cum poured out below my throat. The esophagus is not sensitive, but some of the warmth came through. My hand kept Jason from pulling back, while I slowly pulled off his cock, making sure I got every drop. My mind was not really on it. I was thinking of the sense of power I felt when I forced a reaction from Jason.

That was intense. Was this what Mistress felt when she forced me to react? If so, I could see why she was willing to push other people, with nothing for herself. I suddenly understood why Miss Martel had been so ready, at four in the morning. The night before, I had gotten off, but she had not. I liked to be pushed and forced, but so did other people. If I understood Jason correctly, we could do it together. It was as if my whole world had expanded.

Jason, again, brought me back to the world. He dropped to his knees and kissed me. This made me remember the cum in my mouth. Evidently, Jason did not mind. We held and petted each other for a long time. Then Jason pulled back and showed me the sponge. This time there was no mistaking the evil glint in his eye. One for me, but it was Jason's turn.

He gestured for me to get back on the bed. In his hand was the little round sponge. This he folded in half, which let me clearly see that there was a string attached, sort of like a handle. That explained how I would get it back out. It is strange what your mind thinks about, when a man is advancing on your naked body.

Jason was not about to be gentle. The sponge was in his right hand. His left hand thumbed my clit in passing, then spread my inner lips apart. If I thought it was, perhaps, accidental, what Jason did with the sponge was with malice aforethought. He ran the folded edge of the sponge along the top of my clit, then sawed it a couple of times for extra effect. My lower fires had subsided just a bit. Jason's quick byplay threw on the gasoline.

Then he pushed the sponge through my lips, into my cunt. That was not enough He needed to push it in further, which he did, firmly, with three fingers. Coincidentally, his thumb bumped my clit. I was beginning to notice a theme, in which Jason's thumbs bumped my clit, not that this was a problem. As you might guess, this rough use had me ready for more. Instead, Jason picked up the condom, tore open the wrapper, and handed it to me.

This was awkward. I had never held a guy's penis until this week. Jason's prick was my first and still my only. I had only the vaguest idea of what to do. However, these were his instructions, and I am very good at following instructions. I put one hand on Jason's erection, but my eyes were on the rubber. At first, it seemed like there were two equal sides, but that lasted only a moment. Once I figured that out, I was good to go, or so I thought.

Jason said, "Use both hands to get it started. Then, roll it down slowly, to keep from tearing it. Rubbers are supposed to be tight, so tearing it is a real possibility. Also, leave just a bit at the top, for the spunk. It is possible to blow out the end. No pressure."

No pressure. Right. Following his instructions, I rolled out just a bit, then pulled it back, to make a little gap. Then I unrolled it down his shaft. He was not kidding about it being tight. Once I had it in place, I ran my hands down it a couple times, to smooth it, then I ran my fingernail down the middle of his sack. Jason favored me with a grunt, as I lay bank and spread my legs.

Maybe, finally, I could lose my virginity.

Jason:

Once Tess had sucked my first shot off, we hugged and petted for a while. Tess had surprised me with her initiative, and surprised me again with her technique. It was my turn next and I was looking forward to it. I waved her back to the bed. She remounted the pillows and spread her legs. I flashed back to high school and thought what I would have done to get this back then. The thought came to me that Tess probably would have done it, had we hooked up in high school.

Current events had a small sponge in my hand. I folded it in half, according to the pictures in the box. I just needed to insert it, but having Tess spread out was too much temptation. I folded the sponge with my right hand and goosed her with the left, as if by accident, then spread her open. Tess' clit was a hard point, rising about the rest. I used the sponge two or three times on the point, causing her to jerk. I pushed the sponge inside, then gave it the old three finger push and thumbed her clit at the end of it. Still, Tess did not come. Unreal.

It was time to back off and let her cool a moment. So, I backed off and picked up the condom, which I had pulled from the box earlier, tore open the wrapper and handed it to Tess. She gave a tiny whimper of frustration, but took the rubber. Like a lot of guys, I do not like elastics, but I loved this part. Having a girl roll the condom on is just plain cool, especially if she plays with Lil J a bit. Tess is all about following instructions and that is what I told her to do.

For a newbie, Tess did good. She had it right side out and she made a cum reservoir. More importantly, Tess handled Lil J with respect, except for the thumbnail she dragged up the bottom side. I figured that was just getting back for the bumping her clit, accidentally. So, finally, here we were again. The question was how to play it.

With a more experienced girl, I would single stroke her. There is a lot of shock value in a sudden plunge. But, this was a friendly fuck, and I wanted it to be nice. Once again, I parted her lips with my hand, then slipped in Lil J's head and held it there for a second. Tess' breathing got faster, but otherwise she made no sound. Then I slowly pushed Lil J in, to the balls. This took some effort. Tess was literally dripping lubrication, but was also as tight as my fist in the shower.

Once I was fully in, I said, "Well, young Miss, you are no longer a virgin." Tess' whole body blushed at that. "I want you to grip down with your pussy muscles. Try to drag the rubber right off my cock. If you manage it, you get a prize." Holy flaming shit, Batman. I just thought she was tight.

I pulled almost out. "OK. That was excellent. Now, let up a little as I slide in, and grip down when I pull back. Try to catch my rhythm." It may be obvious to most people, but I have met highly priced call girls that did not grasp the simple concept of rhythm. Tess' took to it like a natural, which I guess she was.

I started stroking, long and slow. Tess was having trouble keeping her feet on the bed, so I put an ankle on each shoulder. This gave me her thighs to use as leverage, so I started banging harder. As I had asked, Tess was gripping and releasing Lil J with each stroke. I started to pick up the pace. After about four or five more strokes, I felt a spasm run through Tess, and she missed a clench. One orgasm. I thrust especially hard the next time, and she was back in synch.

I reached down and jerked a pillow out. This dropped Tess' down a bit, so that I was rubbing her clit more often, and sliding Lil J's head along the back side of her vagina. That was very good for me, and it must have been for Tess as well. Two strokes bought me another orgasm. I was getting close, so I focused on getting maximum friction. It was not easy, because Tess was literally dripping lubrication. I went up on my toes and came down hard. Our pelvic bones met with a jar.

That did it. Tess cried out and her whole body bucked. The massive surge through her pussy shot me off. I was all I could do to stay up on my feet long enough to pull out, then I dropped to my knees and flopped on top of her. Words fail me.

After a while I noticed Tess was running her fingers through my hair. That was nice. I struggled up onto the bed and fell down beside her. Tess smiled shyly at me, radiating happiness like a light house. I kissed her gently and told her she was very special. What a rush. I was limp as canned pasta and the night was still young.

Then I slept.

Interlude: Elle Magazine interview (unedited)

Elle: You say you respect Cynthia. Why is that?

Jason: There is an early 90's gangster movie. The movie sucks, but I always remembered the tag line from the poster. "You only respect what you fear."

Cynthia is a lovely person, when she steps out of her persona, which is most of the time these days. However, I would never cross her on purpose. When she asked me to show her personal submissive how the other side lived, I was not going to say no, and I sure as hell was going to do my best job. Getting a nice fuck was beside the point. I even did some research, which turned out to be useful.

Chapter 10(b) – Back to School

CC:

In my readings, I had noticed that teasing and frustration play a big part in kink. That is Mistress' area and she is expert at it. What I did not realize was that it applied to regular sex. We did not plan it, but twice Jason and I had been right on the edge of coupling and had been pulled back. By the time he actually entered me, I was about ready to scream. Then he did enter me.

How can one describe the difference between a piece of rubber covered plastic and a rubber covered man? It should be sufficient to say that there was one. Jason pushed in his full length and held it there while he told me what he wanted. The idea of squeezing was not new to me. It was all over my reading, but I would have not have thought of it, unless he told. In all my imaginings and my few experiences, the thing in my pussy could not feel anything. It was like a light going on in my head.

Suddenly, things made sense. They called gay lovers "Partners". Even het couples use that term sometimes. Sex was something you did together. Mistress' game playing was much more one person doing to the other. I had a sudden tear in my eye, thinking how she had pushed me to make this discovery. I would have been willing to serve her forever, and never known, what? Friendship?

That was it. Jason was my friend. Just then, my friend pushed deep into me again, forcing his way against my clenched pussy muscles. The feeling was intense. I unclenched and then bore down again. Jason had said I should try to peel the rubber off his dick. That gave me a visual image to work on. We did it again. And again, only this time I lost it in an orgasm, which caused other problems as my feet slipped off the bed.

Jason worked with that. He grabbed my legs and put my ankles on his shoulders. Then he put his hands on my thighs to generate leverage. Another phrase, that had been just words, was "pussy pounder". That was what Jason did to me, not quickly, but hard and all the way down. The slap of his thighs against mine sent extra waves of sensation. Only a few stokes later, I came again. This one was bigger.

Jason went with the flow again. He jerked out a pillow, so I was a bit lower to him. This let him slide his shaft across my clit and rub the back of my space with the tip of his cock. He was breathing hard, so was I for that matter, and I could see that he was concentrating on holding back his climax, while mine built. My climax was going to dwarf the others.

I put all my attention into following his rhythm. It was hard. I did not have much attention left to spare. It could not go on long, and it did not. Jason broke the rhythm to get up on his toes. Then he dropped down on me from that height. My legs slipped off his shoulders, spreading wide. His dick went all the way in as usual, but this time we also met, bone to bone.

I saw stars. I think I screamed; someone did. Jason went rigid, then jerked. Everything was electric and shiny and then mellowed into something warm. Jason pulled out, then dropped to his knees and collapsed on top of me. Mistress said it many times, but never before had I understood, my stars and heavens.

The next few moments were a bit fuzzy. I was gasping for breath. Jason looked like he had run a race. Sweat covered both of us. Jason fought his way to his feet, just long enough to collapse beside me. He had an insane grin and I reached out to pull him close. He stroked my hair and told me I was special. It was all very something.

I lay there, holding Jason, for I do not know how long. I think I must have dozed off, because I became aware of Jason being asleep. The clock on the night stand said 11:00 PM. That really was not late, so I expected Jason would wake up shortly and we could do more things, together.

That was an odd thing. I had not been "together" with anyone for a very long time. Not since Amy Garcia moved away in second grade. So this was my first time being together with a guy. I was not sure I understood what it meant. One thing was clear. I was going to remember my time with Jason. Did this make us friends?

I was only beginning to think of what to do next, when Jason started to stir. It was just as well. The moment had passed and this would be an uncomfortable way to sleep. I brushed the hair out of his face,

and stroked his cheek. He smiled, then rolled over on his back. I was not sure what to expect, but what he said made perfect sense. "Come on. This room has a great shower and we need it right now. Then we can get back to making a report for Mistress Cynthia.

We half held each other up as we moved into the bathroom. Jason was smart enough to grab a towel on the way past. Once we were under the water, it made me wonder why I had not thought of it. I washed Jason, then he washed me, which was another new experience. Under the circumstances, I think Jason might have tried to make something happen, but we were still logy from our. I particularly liked when Jason shampooed and conditioned my hair.

This is not to say that nothing went on. I took my time washing Jason's lovely cock. He claims it is only average sized, but it is plenty for me. I also got to shampoo his hair. Jason has the prettiest wavy black hair. After we were out and toweled off, he let me brush it out as he used the blow drier. Then he did the same for me. I could tell he felt recovered when he used the brush on my ass, to tell me he was finished.

What came next was, in some ways, the most fun thing of the night. Jason had me lay on the bed. He pulled out a book, pen and a pad of paper. I swear. He started checking my erogenous zones. We had already established that I could get off on foot worship.

Breasts: Sensitive, particularly the underside.

Nipples: Sensitive (need you ask?)

Aureoles: Very sensitive

Back of elbow: sensitive and a bit ticklish

Armpits: (armpits?) Sensitive

Wrists: Very sensitive

Navel: Somewhat insensitive

Back of knee: Sensitive

Inner thigh: Sensitive (we almost stopped there. Jason liked stroking my thighs)

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Lips: Sensitive

Ears: Not particularly sensitive

Nape of neck: Highly sensitive

Scalp: Sensitive (this might explain my reaction to the shampoo)

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The basic checklist took over an hour. By the time it was finished I was ready to climb on Jason and do a couple of positions I had seen online. He told me I was just getting me primed for the main event: probing the anus and looking for my G spot. He had an idea about where to find that one.

Jason confided that he particularly like his back side, buttocks, shoulders and the nape of the neck. With a couple of passes, I was in complete agreement. I promised him a tongue bath later. He accepted, and claimed he would hold me to it if he had to take a rain check. Ears are supposed to be a big one, but they did not do much for me. The one that surprised us both was my wrists. It took only a couple of licks, a blow and fingertips dragged down my forearm, to have my heart pounding. Jason's lessons on kissing were pure artistry. He promised to take me out, so we could do it in a theater. For some reason that made me blush all over. Then we studied my pussy and my ass.

This was both very clinical and very sexy at the same time. We started with my backside. Jason stacked all the pillows under me, to push my butt in the air. Then he ran his hands over my glutes. I smiled a bit at the incongruity. I learned the name of the ass muscles from Mistress, at the gym, doing a workout with Martha. Now I was thinking about Mistress doing something mundane, in a setting very like her studio, in some ways. Jason commented that he would love to trade ass massages, when we had the time.

For the moment, we had other things to do. Jason rolled a rubber over two of his fingers, then applied a dab of KY. Mistress had used a couple of numbered spreaders in my ass, so I had an idea of what was coming. That did not count on Jason. Instead of pushing his fingers into my pucker, he licked it. That was a new sensation. Then he ran his tongue around the rim several times. I was all goose flesh and shivering.