Chapter 1: First Time for Everything

Interlude: Elle Magazine interview (unedited)

Elle:

Describe your wildest night of sex.

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."

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 hired to do the camera work for a series of car shows. On the side, 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 Reading, PA). For more than six months, I was getting the very best professional blow-jobs available in the Midwest and Northeast. That was not all. After they finished demonstrating their job skills for the camera, a lot of the girls wanted to do what they wanted to do. So, I also have a lot of experience pleasing women.

Eventually, the river of call girls dried up. Not to worry. Justin found another sex-related job. This one was for an auction of erotica and erotic paraphernalia. It sounded great when we took the job but did not come close to working out. 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, it worked. In the first half hour, Cynthia gave us the theme we needed. Once Justin and Peter were working, 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. Knowing Cynthia as I had come to, it was easy for me 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. We are about the same age. CC is about 5'8", but did not come across as tall. She has a slim figure, without being skinny, but also not athletic. Her eyes and hair are 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 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 all the trouble.

As things moved along, there was less for me and CC to do. The tedious part was done and 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 done by 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, legs apart, sitting on her heels, hands high 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 turnover. 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.

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. All I had done in one of Cynthia's sessions was bondage and suspension. I would remember for the rest of my life. 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?

Christine:

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 boyfriend. 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 him or any of them. By my junior year, all it would have taken was, "Let's go fuck." I would have tried anything the guy or 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 harsh. I drifted down to a job waiting tables at a coffee shop on 7th Street. It was working 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. 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 the first time we met, even if I did not, yet. She told me about Jason and how she tied him up for the picture. I was wet before I met him, then I saw the source videos.

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. His expression is what 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, just inches outside of the shot. Jason and I walked through the entire scene, moment by moment, frame by frame, from all four angles, looking for the perfect shot. We spent hours. Peter spent half a day. Mistress pulled it out in less than a minute. Peter does this for a living but he 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, mine at least, 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. 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 restrained.

It would 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 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 literally beating on my pussy lips like a toy drum. I used actual toy drum stick. They are about six inches long, with round rubber balls at the end and 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 hairbrush. The blood scared me but I was in the bathroom, so I was able to clean it all up. The incident taught 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, which 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. 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, as 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 just a touch of my teeth 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 her ankles.

I had Tess stand. When I picked up the towel, it was not soaked but there was a sizable damp spot. I took a deep whiff of the hormonal smell, then passed the towel to Tess. She looked puzzled as she inhaled.

I said, "That is the smell of female arousal. Since it is very fresh, it is also very light and subtle. It will get funky with time. Train your nose for it, and you will be in on some secrets." Tess' eyes got very wide and she stuck the towel back under her nose. She may be quiet as a snitch in prison, but she is not stupid.

Standing flat footed in front of me, Tess was too tall to see over, barely. I am about 5'11", so that put her about 5'7". I would have guessed shorter. Tess was the same height as Cynthia, who could seem ten feet tall. The mind plays tricks on us sometimes. In any event, height does not matter when you are lying down. I sat down in the chair and pulled Tess over, to stand in front of me.

I reached out and cupped one of her tits. Tess had a nice rack, probably C cup. They were firm, round, only slightly sagging, with a nice ski slope point. The aureoles were pink and somewhat small, but the nipples were the size of pencil erasers, and just as hard. I took one nipple in my mouth and sucked on it. This brought more squirming. I grabbed both her ass cheeks and pulled her as close as she could come. That got me a small gasp, followed by a little kitten mewl.

If there was ever any doubt, that ended it. Tess liked it rough. I added teeth to the suction on her nipple. Tess squirmed some more. I pinched the other one, and she gasped. It took everything I had, to stop there, but I had made promises. I stood and, in one motion, shoved my pants down to my ankles. Tess stared at my cock, then looked up, and I had to tell her no. Instead, I motioned her to the bed. Tess literally ran.

I grabbed her Walgreen's bag. Inside were contraceptive sponges. Obviously, those went inside, but beyond that, I had no clue. I ripped open the box and pulled out the directions. What the fuck? Tess was looking at me with a blank expression. She was as clueless as I was. Fortunately, there were pictures. Guys like pictures: run water on it; knead it til it was all wet; fold it in half; push it all the way in. Groo understand.

I forced myself not to run to the bathroom. Once there I started water running. Then I tried to open the wrapper, the important word being "tried". I tugged, pulled, twisted, jerked and swore at the bag. It would not open. Finally, I took one corner in my teeth and pulled. That dumped the sponge out into the sink. I invented new swear words, but least it had not landed in the toilet.

When I made it back to the bedroom, I found Tess trying to get the wrapper off one of the condoms. Having been in exactly the same predicament dozens of times, I had to snort a laugh. Tess looked up at me, like a kid caught trying to clean up a mess. Then her eyes went to Lil J. I looked down, and sure enough, my cock was no longer at attention. The expression on Tess' face was tragic. Nothing less describes it.

I broke up. I fell down on the bed, laughing so hard it hurt. Tess looked at me oddly, then her lips twitched, then giggled. Finally, she started laughing too. We laughed a long time. After a while, I reached for her, and she came over, still laughing. She lay down, close but not touching. That made it my move, so I reached out and stroked her tits. After a few moments, Tess reached out to touch my face. Eventually the chuckles died enough to talk.

I said, "I guess we were taking it a bit too seriously. What'cha think?" Tess started laughing again. To distract her, I started to get serious about stroking her tits. "You know that you have outstanding tits, right? I know they are not huge, like Mistress Cynthia's, but even she will tell you that bigger is not always better. Come here."

We shifted a bit closer. I asked, "Has anyone ever paid much attention to your tits, naked I mean? Like this?" I put both hands on her left breast and squeezed it gently, like I was checking the ripeness of a tomato. Tess shivered. I rolled Tess onto her back, so that I could more easily reach them both. With one hand, I held it in place, while I ran the tip of my finger around the outside of her aureole. Just as I hoped, her nipple stood up.

Now that I had its attention, I gave the nipple a bath, then I blew it dry. Of course, I did not want the other one to feel left out, so I started over on the right side. This could go on for an hour, and I had done that before, but I had a point to make. So, after five minutes of worship, I sat back and looked at Tess squarely. "You have always had them pinched and whipped, haven't you? Sometimes a little tenderness is nice too. Now, let's see what that had done down lower."

I did not need to look. The aroma of arousal was clear in the air. The question was how best to push her over the edge. I told Tess, "I am going to work further down, though not all the way down yet. While I am doing that, use your hands on your breasts, like I have been doing. Meanwhile, I will be doing this." I blew a raspberry on her navel. Tess rewarded me with a startled squeak, then slapped me on the top of my head. Cynthia had said we were supposed to have fun, which reminded me of something.

I reached down and ran one finger through Tess' cleft. She jerked in response, but that was not the point. I wanted to compare tastes with my sample from earlier. So I held my finger high, then stuck it slowly into my mouth. Tess watched, wide eyed. It was not enough to make a clear decision, so I scooped up another fingerful and offered it to Tess. She took my finger, then smiled at me. I think I detected a trace of knowing smirk in that smile. Even so, fuck this slow foreplay, I am going muff diving.

There are a lot of ways to eat pussy, but my favorite is kneeling by the bed, with her heels on my back. It gives me complete access, and I can use my hands many different ways. When I slipped off the bed, Tess seemed to understand where I was going, because she slid into the perfect position. If she was going to be helpful, I would give her the full course. First a little kissing.

Tess had shaved her pubic hair, so there was none to play with, but I put my lips on the spot anyway. Slowly, I worked my way down that final inch, to the top of her slit. Then I lowered my nose to bump her clit. It seems weird, but I have had very good luck with this approach. Tess' clit was being very cooperative, so I gave it some lip and applied suction. That really got a reaction. This was another thing I could do for an hour and had done before. This was not the time. It was not like I needed to get her ready.

There were so many options at this point. I could roll her clit between two fingers. I could give her the old Triple Jack and One (three fingers and the thumb) fuck. I could turn us both over and eat her bottom up. That was all good, but I wanted to get my own rocks off. So I gave Tess one good lick—she did taste subtly different—and stood to start the main event.

I 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 swear, Tess had a tear in her eye.

It took a couple of pillows to get Tess' pussy into exactly the right place. I positioned myself between her legs and took a deep breath. I gave Tess just the tip of my cock, then pulled it out. I used my hand to start the tip of Lil J at the bottom of her cunt, and pulled it slowly up, between the folds, til Lil J popped up over her clit. Tess whimpered, which was like a screaming fit from most girls. Perfect. I was lined up to do a one-thrust, when I spotted something on the bed. Fuck.

La Jolla moment. How the hell could I be so stupid? My hand banged my forehead hard enough to hurt. I had wet the contraceptive sponge, but never inserted it. For that matter, Lil J did not have his raincoat. Worse, Tess looked confused and hurt.

Eventually, I wound down. Saying "Fuck" repeatedly gets old after a while. When I managed to gather my wits, I pointed at the sponge. Tess followed my finger, then her mouth opened into a silent, "Oh." She looked embarrassed, probably for what she had been thinking. I did not blame her. I would have felt pretty rejected myself. Was there anything else that was going to keep me from measuring her pussy?

I had heard of coitus interuptus, but this was my first experience with the reality. Lil J was sagging to half cocked, and Tess was looking a lot less primed than a minute before. Still, I had to acknowledge an irony. We were naked, willing and in a suitable place, but both of us were frustrated. Back to foreplay.

I reached out and picked the sponge and the box of condoms. Most of my sexual experience came from fucking call girls. That is a situation where a condom is a requirement, or a deal breaker, depending on how you look at it. I had learned that condoms can be sexy as hell, done right. It was time to teach Tess about how to roll on a rubber.

I must have looked evil, or something, because Tess got wide eyed again. I was learning to read a lot from Tess' eyes. This expression said that she was not sure what was coming next, but she liked her chances. I looked straight into those eyes as I pulled a wrapped condom from the box and tore it open. Lil J had been here before, and he was up and eager again. I held the rubber out and Tess reluctantly took it.

I said, "This is a condom. They are 90% effective as birth control and also effective preventing STDs. Most guys do not like them, so you need to learn how to make them work for you. Generally, the best way is to blow the guy first, to get his load depleted, then suck him again, to get him up. Lil J is already up, so we will go to phase two. First, reach out and take my cock. I am like any other guy; where my dick goes, I will follow. Get me positioned where it is convenient for you to use both hands. Feel free to stroke my balls and my cock in the process. Oh, shit."