Chapter 1
In all of our years together, she had never looked at me that way.
Her face was tightly drawn together in concentration and her freckled cheeks were slightly flushed. She wrinkled her short nose slightly -- a habit when she gets excited -- and with her lips slightly apart she was biting her lower lip. Her straight, light red hair was swaying slightly, casting soft shadows over her face. There was a small flash now and again as the small key that she wore on the short gold chain I had given her caught the light. She wore no make-up which highlighted her dimples.
Mostly, though, it was her eyes that looked different. A bright blue, they had always been arresting. Now, though, there were something else in them, something I had never seen. There was focus, to be sure. But her pupils were dilated wide. They paradoxically at once invited me to enter her and displayed her own outwardly facing excitement. They showed vulnerability and strength at once. There was something almost primal in them. She was like a predator who has locked in on her prey with a single focus.
She was looking down at me as I lay on my back, straight into my eyes. She wore a translucent white teddy. She had full, C-cup breasts and I could easily make out her hard nipples underneath. Her chest rose and fell quickly, her breathing shallow, excited, rapid. I was naked, waiting.
My cock was rock-hard. I don't remember that it got that hard, even when I was younger. One reason for this was certainly the thought of what we were about to do. It was, we both knew, a step forward that could not be undone. Another reason was certainly the well-oiled dildo that she had strapped against her mons, the tip of which pressed gently against my asshole. Mostly, though, it was her eyes boring down into me, framed between my upturned legs.
"Are you ready?" she breathed. I was unsure if it was really a question but I nodded.
She was so beautiful. And as I turned my head to the side, noticing again the camera with its unblinking eye pointing straight at us, she tilted her hips forward.
I never would have imagined that I would have found myself in this situation, with a woman fucking my ass. But then, neither would I have ever guessed that my wife -- my sweet, beautiful, innocent wife -- had it in her to do the fucking.
Chapter 2
Sally and I had met thirteen years before at a party. I remember that party vividly, mostly because she largely ignored me.
The party was in a large but run-down apartment in the Upper West Side. I barely knew the host, but it was a Friday night and the friend of a friend or some such person did and suggested that we drop in. It was a hot and muggy day, one of those truly miserable days that also made the City reek. Why not, I thought.
At that time I was an MBA student at Columbia Business School. Like many of my classmates, I lived modestly but in expectation of many giant paydays down the road. This was my fourth year in New York. I had graduated Harvard as a history major and then worked two years for a consulting company. I was about to begin my second, and last year, in the MBA program.
I didn't have much of a life in New York. I lived in a bubble and spent nearly all my time on my schoolwork. That summer I also interned with a small venture capital fund. I tried hard to find the time to socialize after work but the hours were long and I was largely exhausted when I finished. Perhaps I was also a little depressed. Day in and out we looked for ways so that rich people could use their money to become richer. I was unsure if this was the way that I wanted to spend the rest of my life. There are, of course, many other things that one could do with an MBA but I was also unsure if any of them would be any better.
And, if I am being completely honest with myself, I was a jerk. In fact, I was a jerk for as long as I could remember. I grew up comfortably, if not extravagantly. We lived in Westchester in an affluent suburb of New York. My father worked in finance and my mother was a doctor. They weren't home a lot but they did buy me and my sister lots of stuff to keep us busy or, as I now realize was more likely, to mitigate their own guilt. I went to a local prep school, which was full of privileged whites very much like me, with a few token and instantly recognizable diversity students. This was the kind of school that was meant to keep people out rather than bring people in. As I remember it, there was a more or less even balance of boys and girls.
Everyone played sports I took up lacrosse. I was built for it. At 6 feet and 180 pounds, I had broad shoulders and was muscular. I was both quick and fast and they played me at wing. I looked good out there in my uniform and with my stick, often able to knock my opponents to the turf. Looking good is not the same as playing well, though, and I was actually a pretty mediocre player.
I fell in with the jocks. This helped my self-esteem. To be with a group of privileged, arrogant, testosterone-fueled guys meant never having to admit your mediocrity. We were the royalty of the school, at least in our own eyes. We walked through that place like we owned it, especially during our last couple of years of high school. Academically I also did well, although I sometimes felt the pressure to tamp it down in order not to embarrass the other guys. I wanted to fit in.
Among high school boys there is so much ridiculous talk that it is hard to know what is true. If my friends were to be believed, they were getting it all the time. My own experience was different. I was awkward around girls. When I was together with my friends we would talk about girls like objects, ranking their looks and talking about what they might do in bed. I was completely comfortable talking like this and often was the one with the sharpest, most offensive (in retrospect) things to say. During my junior year four of us, led by a senior, planted a hidden camera in the girls' locker room. We posted some of the footage on the Internet. Thank goodness it was discovered quickly and taken down, although they never discovered who did it. I was not the ringleader but I did get a rush. Thinking about this today is painful.
When I was talking one-on-one with a girl, though, I was just awkward. My sister and some of the girls in my classes were not objects but real people who surprisingly did not idolize me. It was hard for me to ask a girl out. She is the one who should be asking me.
As a result, while my friends were talking about the vast amounts of sex they were getting, I had limited experience. I wouldn't admit this to my friends, of course. My first dating experience occurred when I was a senior. I screwed up the courage to ask a cute classmate out on a date; we had both recently turned eighteen. She was fun and funny, although shy. After a couple of dates we kissed. After another couple of dates I suggested that she give me a handjob, which she did reluctantly. After that she never called me back. I told my friends that she was an easy lay.
Harvard teemed with diversity and student activism in a way that was completely foreign to me. Every ethnic, racial, religious, sexual, artistic, and oenophilic group imaginable banded together to fight for...something or other. There were protests, marches, and a bewildering number of sensitivity-awareness sessions, most dealing with issues of race, gender and sexuality. It was an incredible ferment of ideas and idealism.
At least that is what I was told. My first year I was assigned to a quad. Two other guys who were just like me. The fourth was a Latino from L.A. who was getting a full financial ride. He was nice enough but it was the three of us quickly bonded. We made fun of Emil a little (we skipped the sensitivity training) and went his own way. Our little group quickly located the other little groups that were just like ours. It was very easy for us to recreate for ourselves the prep school environment in which we were comfortable. I did well enough academically, but my focus was really on building the networks that help me to get ahead.
I dated some throughout college, mainly girls from our same social set. They were nice girls -- "good girls," really -- with whom it was easy to find common ground and get along with. I lost my virginity freshman year to one. It was after a party and, tipsy, we stumbled back to her dorm room. She was more experienced than I was and she took the lead. I'm pretty sure that we used a condom, which she supplied. I'm also pretty sure that she didn't come. It was uncomfortable enough that the next morning and later, the few times that our paths crossed around campus, we pretended not to see each other. Still, I wish I remembered her name.
During college I had only one serious girlfriend, Lisa, who was in my class. She was from Deerfield, Michigan. Tall and blond with blue eyes and not many curves, we were drawn together more by the mutual overlapping of our friend groups than by any deliberate effort on either of our parts. It was fun. We spent most weekends together our junior year and would sometimes get together during the week to fool around. Lisa, like many of the women I hung out with, was not very sexually dynamic. It took a long time to warm her up and even then she remained reserved. I'm not sure if during the whole year she had more than a half-dozen orgasms with me, which made me feel even more insecure than I already was around women. It is me, not you, she would say. But as a man trying to find his sexual footing it was hard to believe that it had nothing to do with me.
As I think back, these certainly were not great sexual experiences. We did not often have intercourse. It seemed like it was too big a deal for the payoff. We were afraid of the risk of pregnancy even with the condom, which we always fumbled while we tried to put it on. We each had roommates and we were afraid of getting caught. We both enjoyed how it felt and I almost always came (there were a few times when I had had too much to drink that night) but Linda often felt frustrated. So instead we spent more of our time making out.
I learned a lot in those make out sessions, both with Lisa and with the few other girls I later saw my senior year. Linda and I would make out for hours, mainly kissing and necking. We would sit for hours kissing, our hands caressing each other's (usually at least partly clad) bodies. I learned to lightly wet and soften my lips when kissing and to use my tongue sparingly, more to tease than anything else. I would hold her head gently between my hands and graze her lips with mine, flicking my tongue into her mouth so only the tips of our tongues meet, and then draw back. We would do that repeatedly until she wanted more. Our kissing would become increasingly passionate as I would run my hands down her body, just grazing her hardening nipples and moistening pussy.
And that is also how I learned about patience. It just took a long time to get Lisa aroused. Only after a good amount of time kissing and teasing her with my fingertips would I tug her pants off or, better, slide my hand up her dress. Then the manual stimulation would begin. Through trial and error I learned a technique that I would later find called "orgasmic massage." I would use some lube -- spit would work but I preferred the store-bought water-based kind -- and run my fingers over her pussy. I would not penetrate her; just tease her, with different speeds and pressures in different parts. I most enjoyed holding her pussy lips open to help expose her clit and with the barest pressure circling it with my lubed finger. I usually did this for about thirty minutes but once I maintained manual pressure for a full hour. After that she couldn't wait to fuck.
Most of the time, though, that would be followed by a lengthy head session. I never rushed. While I was playing with her clit with my fingers I would also begin to lick at her breasts. I would wet her nipples with my tongue and then blow over them, teasing. I would kiss her whole breast with an occasional, random sharp flick of my tongue at her nipple before bringing my whole mouth down her tit, sucking. When she had enough of that I would begin to kiss down her belly; over her mons; right to her inner thigh. My mouth would linger there a little while before moving to the other thigh, being sure as I transferred to let my nose quickly touch her swelling pussy. Only after I ran my tongue up the crease between her lips and her leg would I begin to lick her.
Cunnilingus, I have grown to believe, is an art form. It is a little like playing an instrument. Each woman reacts differently to technique. It drives one woman crazy when you suck her pussy lips while another could barely care. This woman loves hard pressure on her clit, that one's clit is so sensitive that I restrain myself to letting her feel my hot breath on it. With a new woman, I try different things, trying to take measure and adjust according to how she reacts. Like most of the women I fooled around with, Lisa did not react very much. She told me that since her clit was sensitive she most enjoyed when I ran my tongue up and down her slit. I have no reason not to believe her -- I would do this for twenty to thirty minutes at a time and she never encouraged me to stop. But I would have liked to have had more of a response.
