J and Silent T
Chapter 2: Back to School

Copyright© 2013 by PocketRocket

Erotica Sex Story: Chapter 2: Back to School - He was a teenage Romeo. She was a blushing virgin. Oops. That's misleading. This is not your usual first time story. For one thing, she is a submissive. No BDSM. The subject does come up, but this story is about lots of vanilla sex. Not a true stand alone. It ties into the end of "[K]itten & [T]eddy Bear." Jason is from "A Study in Foreplay." CC/Tess is from "New Hire Orientation."

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   Consensual   First   Safe Sex   Oral Sex   Sex Toys  

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 tagline 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. Still, 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.

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 were pulled back. By the time he actually entered me, I was about ready to scream.

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 not have thought of it. In my imaginings and few practical experiences, nothing in my pussy could feel anything. It was like a light going on.

Suddenly, things made sense. They called gay lovers "Partners". Even het couples use that term. 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 said I should try to peel the rubber off his dick. That gave me an image to work with. We did it again. And again, only this time I lost it in an orgasm, which caused other problems. My feet slipped off the bed.

Jason worked with that. He grabbed my legs and put my ankles on his shoulders and 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 strokes 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 the bottom of my clit and rub the back of my space with the tip of his cock. He was breathing hard and so was I for that matter. I could see that he was concentrating on holding back his climax while mine built. Good. This time, 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 his full 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. Jason pulled out, then dropped to his knees and collapsed on top of me while everything went warm and mellow. Mistress said it many times but never before had I understood: 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 nightstand 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 leaned against 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, I wondered why I had not thought to suggest it. I washed Jason. When he washed me, it was another new experience. Under the circumstances, I think Jason might have tried to make something happen. Still, it was nice. 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 interesting 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)

.

.

.

Lips: Sensitive

Ears: Not particularly sensitive

Nape of neck: Highly sensitive

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

.

.

.

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 liked attention paid to his back, buttocks, shoulders, and the nape of the neck. After 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. Next, 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. I was thinking about Mistress doing something mundane while I was 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.

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 pulled 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 close to 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.

Jason moved his fingers forward and scratched at the roof of my pussy. Holy shit, again. That was my G-spot. 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. She 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 had learned a great deal about anal sex. I can find a prostate under 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-spot then trilled her clit with my tongue. 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. It was intensely flattering. It would have felt better, but I had an itch that had not been scratched, yet. Also, Tess 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 three foot long 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. Time for some personal gratification.

I told Tess my evil scheme, "Tess, that is the end of my list. However, I noticed a couple of things that suggest a 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 usually flippant 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, while 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 observe her reaction.

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 also interested in how this turned out. It was not going to be easy. The huge dildo was easily as large as my wrist and three feet long. We needed it up my ass. Jason was patient, so I was surprised how soon that massive thing slid into my chute. Once it was started, Jason kept twisting it back and forth as he worked it further in. That actually took longer than getting me open far enough to accept it.

Jason said the dildo was supposed to be filling and he was not kidding. I felt incredibly full. All the twisting of the dildo 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 rolled over. As I had done most of my life, my fingers started tapping on my bump. That felt really good, 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. Jason, with yet another condom on his fingers, was reaching for my cunt. This time, the palm was down instead of up. From the moment he touched my lower lips, it was different. From the moment 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 Johnson 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 prompted. 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 what guys are like where you are from. In my part of southern California, the slow fuck is the standard of skill. It 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.

I began 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. "This chair is against the desk. It 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. I gasped, "Exactly that. Can you do it again?" Tess could not do it again on the first try, but she found it faster the second 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 before she drifted back far enough to try again. I said, "Good. Now stop. Notice where you are positioned. Try to do the same thing, backward." This took longer. Eventually, Tess noticed she had undone her first move and did it again. 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..."

 
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