Itty & Teddy Llc

Author's note: This chapter is not necessary for the mainline story of Sheila and Sean.

Tolkien once said,

"There is a new character in my book, and he is not entirely welcome.

" For this story, that character is CC/Tess. This is mostly her chapter, with more on Jason. I hope you enjoy it. Sheila and Sean will be back with the next installment.

As always, thanks to clairegerm for editing.

Interlude:

Elle Magazine interview (unedited)

Jason:

"Do you know how to tell the difference between a fairy tales and teenager's sex stories? Fairy tales will start, "Once upon a time..." while the sex stories will start, "There we were..." After that there are no noticeable differences.

"There we were, in my hotel room, the teenage Romeo and the blushing virgin. I said, 'Why don't you take off your clothes and get comfortable.'

"Before I could pull off my own shirt, shoes and socks, she was bare naked and kneeling on the floor. She sat back on her heels, with her legs wide apart, showing her bare cunt. She had her arms high behind her back, grasping her own elbows, which pushed out her perfect C cup tits. Her eyes were fastened on my crotch.

"I did not say she was a typical blushing virgin."

Chapter 10(a) –

First Time for Everything

Jason:

My previous year was the stuff of wet dreams and bad fiction. I had obtained a job working for Justin Immons, of Immons Images, a professional photographer. He was shooting publicity pictures, for a long line of expensive call girls. As part of the process the call girls would demonstrate their assets and skills, especially their technique at fellatio. That would be blow jobs if you live in La Jolla.

It turned into a full scale competition, and I was the lucky judge (the winner was Roxanne in Scranton in case you are interested). For more than six months, I was getting the very best blow jobs available in the Midwest and Northeast, and that was not all. After they finished demonstrating job skills for the camera, a lot of the girls wanted to do what they wanted to do. So I have had a lot of experience receiving blow jobs, and a lot of experience pleasing women.

Eventually, the river of call girls dried up, but Justin found another sex related job. This one was for an auction of erotica and erotic paraphernalia. The problem was that it did not come close to working. Justin and Peter, the tech guy, could not come up with a layout that would pass muster. Enter Cynthia, the new Art Director. Justin had to swallow his pride and let someone else take over creative control. That is a very big deal in the art world. Worse, Cynthia was not a photographer; she was a dominatrix. Disaster loomed.

The odd thing was that it worked. Cynthia gave us the theme we needed in the first half hour. Then she took me to her studio. We had a session. I will remember that session to my dying day, and we got a ton of good video. Then suddenly, it was like

Forrest Gump

after the hurricane; everything was easy. Cynthia blended in like bananas on peanut butter. The next day, she started bringing an assistant, CC.

It was not an obvious fit, at least at first glance. CC had no experience and no skills. But, knowing Cynthia as I had come to, it was easy to see. CC was a born submissive. Cynthia said to put her to work, so the professionals, Justin and Peter, stuck her with the other non-professional, me. We did the drag-and-drop work of pulling shots from files and mounting them in the prepared slots. It was tedious and picky work, but not anything that required intelligence. Over time, I sort of got to know CC.

Part of it was easy. CC was about 5'8", but did not come across as tall. She had a slim figure,without being skinny, but also not athletic. Her eys and hair were brown, and neither brought an automatic second look. In fact, nothing about CC brought a second look, unless you had a reason. She was nineteen years old, but could pass for sixteen. I doubted CC went to bars, but she would have trouble getting in, even with an ID. There was an innocence about her, til you looked into her eyes. There was mileage to read in CC's eyes.

I say "I sort of got to know" CC, because she never, ever talked about herself. That is not strong enough. CC almost never said anything, at all. She was as quiet as my favorite comic, Silent Bob. When she went to a restaurant, she would hold up the menu and point. Talking to her was an exercise in reading facial contortions. Often, it was like playing charades, and she would give you a smile when you hit it right. Trust me, that smile was worth the trouble of getting one.

As things moved along, there was less for me and CC to do, because the tedious part was done. The rest was for the Cynthia, Justin and Peter to work out. By Thursday night, even that was getting thin. To give you a benchmark, on Sunday, we were scared shitless that we would not be ready on Saturday. So, Thursday night, we were feeling a bit loose. Cynthia came in with CC, and loose took on a whole new meaning.

I said that CC was a submissive. I could tell, but it was not made obvious. That night, Cynthia asked me to give CC pointers on giving head. Heaven knows I was qualified. CC dropped to the floor, in the same pose, including hands behind her back. I opened my pants and let her have Lil J. It was only natural to tell her how to do it as we went along. CC was not skilled, but she was very willing. Once we were done, Cynthia called CC names and told her to assume punishment position. This meant ass in the air and face on the floor, with only the elbows for balance. Even before CC was settled, Cynthia pulled down her workout pants. Naturally, there was nothing under them. Cynthia asked Peter to fuck her in the ass.

It was hot as hell. We have video.

On Friday, we wrapped up the small remainder. The final result was beyond good. I am no professional, but Justin and Peter are. They were both in awe of the way things turned out, particularly the cover shot of yours truly. Soon, the three of them would go off to meet Mr. Richards, at the printer, and do the official turn over. Before they left, Cynthia came up to me, looking very serious. I have a lot of respect for Cynthia. When she is serious, I am too.

She said, "Jason. We have one small piece of unfinished business. I gave Richard and Paul a signed photo of our session, but not you yet. While we are gone, why don't you and CC pick out some possibilities? I still have creative control, so do not go overboard." Cross Cynthia? Not in this lifetime.

Then she turned straight toward me. "You have my permission to take her back to your room and teach her how things are between a man and a woman. If she is not a virgin, in the normal sex meaning, she is close to it. I want you to show her how it is done. Keep some distance. Talk her through it. Explain as you go." Holy fucking shit. She could not be serious. It got worse.

"I just did a session with her, to the point she asked out." It was worse, much,

much

worse. Cynthia paused, but I had gotten that. I had been in one of Cynthia's sessions, but all I did was bondage and suspension. CC was much more submissive than me. If she asked out before the finish, it was getting dangerous, as in police reports and hospitals. I nodded understanding.

Cynthia went on. "She came, I do not know how many times, but not the last time. I want you to coax the last one out of her, using only ordinary means. I know this is a lot to ask, but you have skills. Are you willing to try?" Oh my fucking god.

The worst part was when she said, "you have skills." I respected Cynthia, a lot. That was high praise and she was asking for a favor. I could not say no, but I had never had a virgin, not even in high school. What if I let her down?

Tess:

Have you ever dreamed of being snatched out of your life into something much grander? That happened to me. One day I was a waitress at a greasy spoon diner. The next day I was working for Richards Enterprises and was introduced to my mistress. The next I was given to her. It was like a dream come true.

I am very quiet. Even I think so. Finding the right word can be so difficult. By the time I was old enough for school, everyone tended to avoid me, even the bullies. I guess it is not fun if you cannot get a reaction. I made decent grades in school, because all the tests are in writing, but most of my teachers treated me as if I were slow. After high school, college was not an option. There was no money and no one thought I was good enough anyway.

It goes without saying that I never had a serious boy friend. What might be harder to believe is that no one tried to make me a one night conquest. Not even Ted hit on me, and he claimed every other girl in the class. The weird part is that I would have let them. By my junior year, all it would have taken was, "Let's go fuck." I would have tried anything the guy, or the girl, wanted to do. Instead I went home and read fantasy stories about women who get enslaved by barbarians, but manage to cope through sex. You have heard of Gor, right?

After high school I had to find work. That was easy sometimes. I look good on paper. Some people only want to read the application and see you nod to what they say. I had trouble keeping a job. Sooner or later the owner, or manager, would get tired of me not saying anything and find a reason to fire me. It was pretty harsh. I drifted down to a job waiting tables at a coffee shop on 7th Street. It was working pretty well, because no one wanted to hear about daily specials.

Then it happened. Two guys came in for lunch. They were talking about erotic photography, the kind with handcuffs. I was getting wet just hearing about it. Then they noticed me listening. A few minutes later one of gave me a card saying Richards' Enterprises and told me to call in the morning. When I did, they told me I had been hired at the diner, so I was already late for work.

That day I met Mistress Cynthia. She warned me not to call her that, but I still think it. Mistress knew exactly what I was from the first time we met, even if I did not, yet. She told me about Jason, and how she had tied him up for the picture. I was wet before I even met him. Then I saw the video we took the picture from.

You have probably seen the picture by now. It is a simple upper torso portrait of a bound man, staring at something outside of the frame. It is the expression that gets everyone. There is a mixture of pain, fear, longing and lust, all at once, and all folded into a beatific expression of acceptance. The object he was staring at was a riding crop in Mistress Cynthia's hand. Jason and I walked through the entire scene, frame by frame, from all four angles, looking for the perfect shot. Mistress pulled it out in less than a minute. Even Peter, who does this for a living, does not know how she does it. Mistress is very gifted.

For work, Mistress put me with Jason. We worked at the simple, repetitive but tricky part, while she, Peter and Justin worked on the fancy part. It was nice. Jason and I worked well together. After we were done for the day, Mistress sent me to her friend Francine. It was interesting. Francine had me strip naked, then kneel with my hands behind my head, then went away for a very long time. Mistress told me later that Francine had apologized for being gone so long.

When she finally came back, Francine showed me how to maintain the posture more easily, which I liked a great deal. Then she showed me Second Posture, which is exactly what I needed. I sit on my heels, knees apart, with my hands behind my back holding the elbows. It is very relaxing, yet it gives Mistress easy access to my pussy and my tits. Mistress has gone so far as to bind me in the posture when I am observing her work, though she usually includes a butt plug and dildo or ben wa balls.

That was how I went, in less than a week, from a lonely girl who had never been kissed, to the happy submissive of my Mistress. In my entire life, the only one that had every made me cum was me. Mistress has found all sorts of ways to make me cum, usually involving whipping my pussy in some way. It is so much more satisfying than spanking it myself, which I had done for so long. Perhaps I should explain spanking pussy, since it does not appear to be well understood.

My first sexual experience was at age six. I was in the school parking lot, running, when I hit a short metal pole, right between the legs. I must have passed out, because the next thing I remember was being in the nurse's office, with my skirt up and my panties down. Mrs. Voss was prodding the area between my belly and my cunt, not that I knew what it was called. The bruising was very serious, and it must have already been coloring and swelling. Even then, I can remember that some pokes hurt and others hurt, differently.

The next day, my mother took me to see Dr. Carlson. He had my mother hold me while he examined the area. Again, some of his prodding made me squirm because it hurt, and some of his prodding just made me squirm. There was a difference. This time my hands were held.

This was to become a pattern for the next several days. Every night my mother would hold my arms, while she tested the tenderness of my pelvic area. This is one place where being non-verbal probably helped. Mother would have stopped, if I had said what I was thinking. She might have taken me to a shrink.

In any event, the bruising improved and the probing stopped. Naturally, I started doing it myself. Just probing with fingers was nice. It did not take long to figure out where the sensitive spots were. I can remember wondering why Dr. Carlson and Mother never touched me quite that far down. After a while, I discovered I could get a bit of that mix of pain and pleasure if I hit it with my fingers. Soon I was beating on my pussy lips like a toy drum, literally. I used the sticks from a toy drum. They are sticks about six inches long, with round rubber balls at the end. I still have them.

A while later, I had a discovery. It worked better if there was something in the slot. Fingers soon gave way to other things. I broke my own hymen before I turned eight. It was with the handle of mother's hair brush. The blood scared me, but I was in the bathroom, so I was able to clean it all up. The incident did teach me caution about using anything with even a slight edge.

The whole thing with having the arms held took a lot longer. Tying your own arms is counterproductive for autoerotica. I did not rediscover that, really, til I met Mistress. She has tied me up and whipped my pussy so much better than I ever did by myself. Now one of my fantasies is being tied to a bed, spread wide, with someone drumming Michael Jackson's

Beat It

on my special bump.

Mistress knows me so well. It is funny, I suppose, that I lived 19 years, and never realized I was a submissive with masochistic tenancies. Sean Richards recognized it as soon as he saw me. Mistress not only recognized it, she has been training it. My favorite was the office party. She had me kneel and blow Jason, with everyone watching. Then I was turned over and Peter stuck his big cock in my ass and pounded me out. I must have cum five times. Afterward Mistress told me never to forget that it had been a scene. Scenes are pretend. Life is something else.

Tonight I am supposed to go with Jason and not pretend.

Jason:

There we were, in a nice hotel room, her naked and me down to my shorts and jeans. I was wondering what to do when I noticed a Walgreen's bag. When in doubt, look for something unusual. With CC's eyes tracking every move, I went and picked up the bag. Inside were exactly the kind of thing you would get for your first real sex: contraceptive sponges, spermicidal gel, sexual lubricant and condoms. The condoms I understood intimately, pardon the pun. Call girls are serious about protection. I was glad to see, thank you Cynthia, that these were in my size.

It occurred to me that figuring out how to use the other might be fun, but not as a first thing. Contraceptive gel tastes worse than shit, and I know from experience. So, if I was going to eat that lovely bare pussy, we would do that first. In fact, we could do a lot of exploring, first.

I said, "CC, please get a towel, better yet a lot of towels. We are going to explore your erogenous zones." CC's eyes got very wide. Then she jumped up and ran to the bathroom.

The first thing to decide was where to play doctor. When I thought of it in those terms, the bed seemed inappropriate. My room had a couple of arm chairs, and the rug was thick. I was more than willing to kneel for something like this. I pushed back the coffee table to make room.

CC returned with an arm full of towels. I doubled up one of the big ones and laid it on the chair cushion, hanging off the front. CC caught my idea immediately, and sat down on the towel, with her legs up over the arms. It was a perfect pussy eating position. In fact, it surprised me that none of the call girls had suggested it. CC seemed to like it very much. I had only been in it for seconds, and there was already a drop of honey oozing from her cunt.

I said, "CC, has anyone ever licked your cunt before?" I did not expect an answer, but I got one.

"Tess."

That one word was so out of place I stopped short. "You want me to call you 'Tess'?" CC, that is Tess, nodded vigorously. "That means something, doesn't it?" Again, she nodded. I looked a question at her, and she finally answered.

"Truly Scrumptious"

How appropriate. "We shall see." I reached out one finger and picked up her drop of dew. Holding it for her to see, I tasted it with my tongue. Every woman tastes different, and Tess tasted rather fresh. I held the finger out to her, and she took the whole thing in her mouth. Lil J, my cock, jerked in recognition. Tess smirked knowingly.

I said, "Not bad. We will have to resample in a while, and see if it is different. For now, I will see how much we can get, before we go to the source." Tess' eyes got very wide, as she correctly read my meaning. Her pussy would be the last thing I tried.

Tess' knees were up, over the chair arms. The angle was awkward, so I stretched one leg out. Tess giggled, but I do not think it was from tickling. We could try that later. Instead, I stroked her calf several times, up to the back of her knee. That brought a different reaction. Then I lightly stroked the back of her knee, which brought a small gasp. That deserved a comment.

"Tess, I know that when your Mistress services you, she prefers silence. That does not apply here. Let me hear you. It tells me that I am doing something right. In most cases, when a girl is with a guy, the guy wants to hear her reactions. Gasps and moans are a good thing, a long as they are real." I could see that this was news to her, but she nodded understanding.

I stroked the back of her knee again, which brought a jerk. I asked, "Do you like that?" as I continued to stroke her lower leg. Tess did not say anything, but she is very good at nonverbal communication. So I pulled her foot to my mouth and sucked on her pinkie toe, then ran my tongue over the webbing between the toes.

Foot worship is not a big deal for me, but I can hum the tune and dance a few steps. From her reactions, I thought it was a bit more to Tess. To test my theory, I ran my tongue across her arch, then put a touch of tooth on her heel. Tess was still making no noise, but her squirming was speaking loudly. This was worth looking into, but later. I would pass Tess' reactions on to Cynthia. For the moment, I needed to look above the ankle.

I had Tess stand. When I picked up the towel, I found it was not soaked, but there was sizable damp spot, which smelled hormonal. I took a deep whiff, then passed the towel to Tess, miming for her to do the same. She looked puzzled as she inhaled.