Chapter 1

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Ma/Ma, Consensual, Romantic, BiSexual, Heterosexual, FemaleDom, First, Anal Sex, Sex Toys, BBW, Slow, Transformation, .

Desc: Sex Story: Chapter 1 - Casimir wants nothing so much as a relationship with a woman. The problem is that all of his sexual experience so far has been with men. Then he sees an interesting personal ad in the paper. The woman implies that she's looking for anal sex. Now THAT Casimir knows a few things about. But there could be trouble ahead...

1974. Nixon had resigned on a hot August day. Rockefeller would become Vice President that winter (and just a few years later he was destined to expire in a highly compromising position with a young female staffer). Vietnam was still simmering on the back burner, and policy makers expected that the American-supported regime could hold on for the foreseeable future (President Thieu would ultimately prove more adept at running a liquor store than a country). The Arab oil embargo was just beginning to fade into the recent past, yet gasoline remained at a painfully high seventy cents a gallon. New York City went bankrupt, and its feisty little grey-haired mayor defiantly proclaimed that it was still the Big Apple. And that's where I lived at the time, Noo Yawk, Noo Yawk, and I was lonely and horny, though not necessarily in that order.

At 26, I was still a virgin, a "technical virgin," that is. What this means is that I had never been with a woman in that particular way. I liked women all right, could very easily have loved them, but they terrified me. I was afraid of not doing the right thing with them, of being rejected, laughed at, falling flat on my face, failing.

I wasn't really a virgin in every sense of the word. I had been with men a number of times. I didn't really consider myself homosexual (or, in the contemporary usage, "gay"). Admittedly I very much enjoyed being the passive partner in anal intercourse, and even found it moderately satisfying switching roles. There was something profoundly sensual about a dick sliding into my ass, penetrating deeply, moving in and out. That powerful moment when the guy bending over me would gently part my ass cheeks with his hands, then his vaselined dick would first touch, then push against my asshole (sounds more true-to-life than anal sphincter, doesn't it?), and it would dimple inward, then open. Now the magic, the clash of cymbals, as the head of the dick popped past the outer, then the inner ring of muscle, then, meeting no further resistance, slid smoothly upwards, penetrating deeply... up into my very guts. It even got so I found the faintly pungent residual shit-smell afterwards a turn-on. Yes, I liked taking it in the ass, up the ass, but... I didn't much care for men otherwise. I liked women, I loved them, I loved their touch and their smell and their curves and their softness and their femininity.

How I longed to cuddle against a round, soft body after we had both had our fill of each other. How I wanted to rest my head on her breasts at that moment, then fall asleep. How I craved having her nice round ass to caress as I woke up next to her. What a jarring contrast with the reality I had settled for -- a man, a hairy, sweaty stranger uncorking his slimy, dripping, limp cock from my ass and walking out the door. I was sick of this coarse, stripped-down version of lust. I wanted a woman, a special woman to love and be loved by.

I had just about given up. I was just plain too shy, too scared, too awkward and fumbling, too socially inept to get a girlfriend. Then there was the guilt, the thought that having been penetrated by men had somehow contaminated me, made me less of a man myself, made me unworthy of loving and being loved. Even the thought of approaching a woman made me break out into a cold sweat. Then I saw her ad.

Gentleman, gentle man, special man sought for a deep and intimate relationship, for a very special kind of love. If you have ever read Norman Mailer's story, "The Time of Her Time," and been moved by it, you might well be the one. You are likewise special in all other ways. You are a seeker, driven to explore the hidden paths.

What impelled me to read the personals in the "Town Crier" on that one particular day? I wasn't in the habit of doing so, generally finding female-seeking-male personal ads tedious, or at best grimly amusing -- mostly women looking for a perfect mate, not to mention the fulfillment of all their other assorted fantasies as well (the fairy tale theory of life). Yet this ad caught my eye.

Yep, I had read Mailer's notorious tale, part of his "Advertisements For Myself" collection of early writings. It was quite a departure for him, and possibly the first mention of anal sex in mainstream literature. That was in the late '50s, and the lit'ry establishment had been quite scandalized. I found the story provocative and a huge turn-on when I read it as a teenager. Imagine, an experienced stud and cocksman goes through his entire bag of tricks to bring a "frigid" woman to orgasm, but nothing works... nothing, until he tries, fighting her initial reluctance, tries to fuck her in the ass. He gets it in, against her furious resistance, and despite the pain this brings her to an explosive climax, the first of her entire life, if we are to believe the narrative.

(Nothing there about the special relaxation techniques needed for painless and pleasurable anal penetration. That might have been too much for an Eisenhower-era readership to stomach, or just maybe the great author himself was clueless.)

The story might have been a liberating breakthrough, the dawn of a new era of freedom when written, but now in the enlightened mid-70s, sodomy was no longer such a big deal. The story was not even all that well done, but then I didn't much care for anything Mailer wrote after "The Naked and the Dead," and I hadn't much cared for that either.

I wasn't at all sure I wanted to respond. It's not as if the woman in the ad were offering a simple, "starter" relationship that an inexperienced boob like me could handle. This was about kinky sex, with all the additional layers of complexity that implies. And how many years had it been since I had tried for any kind of relationship at all with a woman? What could I offer this one? Yeah, I knew a thing or two about ass fucking, learned firsthand, both as a top and a bottom. So what if it was with men? Were women all that different? For that matter, could that particular portion of a woman's anatomy where she shits be all that different than a man's? What the hell. I sat down in front of a borrowed typewriter and began to pound the keys.

Gentle gentlewoman,

Relationships between two seekers of beauty and hidden meaning are rare and precious jewels. Mailer might well have hit upon something -- that just possibly the path to the Fundamental passes through the Fundament. His character, though, didn't have a clue. He forced his way in, causing pain and violation. The woman was quite within her rights to dismiss the accidental bringer of her pleasure, to kick his butt, actually. Done properly, the act brings exaltation and intense pleasure to the woman (no pain! no pain!).

I'm offering more, much more than mere fulfillment of your cherished fantasy. Mutual appreciation and enjoyment of a particular variation or act is not in itself, unfortunately, sufficient basis for a sustained relationship. Note, therefore, that there is substance to me far above and beyond any fetishes and/or preferences I might be partial to. Yes, there is life after sex.

Certainly I did go on a couple of pages about my interests and so-called accomplishments. Candle-lit dinners, midnight walks along the beach, cuddling in front of a fireplace in a mountain cabin... all the embellishments women allegedly fall for, "purple prose" straight out of the women's section of the supermarket tabloids. I always could write, even if my Junior High English teacher thought otherwise. I figured the woman would get maybe 30 or 40 responses, about half of them illiterate or just plain moronic, and most of the rest not quite on the mark. I gave myself at least a fighting chance of getting a reply.

The letter came. It was on expensive, linen-weave stationery lightly scented with jasmine. She was Amelia Gilbert (she pronounced it "Zhil-behr," with the accent on the second syllable), a Belgian businesswoman representing a European investment syndicate. Age indeterminate, but hints that it might be somewhere in the 30s. No photo accompanied the note, but my imagination pictured her as a stately and dignified woman, immensely sure of herself, proud in her bearing... somewhat resembling the cover photograph on Stephen Vizinczey's classic, "In Praise of Older Women."

My turn to tell about myself. She requested a recent picture and a short bio ("curriculum vitae," she called it). So I sent her a shot taken at one of those photo-booth places that used to be in every mall and game arcade. (The pictures came out in a wet strip looking like they were taken by a morgue photographer, but, hey, they were cheap.) I've always looked younger than my age, and back then I still looked pretty much like a teenager. Maybe she'd get a charge out of "robbing the cradle." And I constructed an intricate and wonderful word-picture of myself. Even then I'd led quite an interesting life, and if I didn't have money and status to show for it, I was smart, had something of a sense of humor, and even a thin veneer of "kultcher." Yeah, I looked much better on paper than in person. Put me in front of a woman, a real live woman, and I'd become a sweating, stuttering, clumsy idiot.

For some reason she wanted to meet me. What now? How the bloody hell did I get myself into this mess? Still, after all that effort, I wasn't about to turn chickenshit and run. I'd forever be wondering what I'd missed out on. And where could I run to anyway?

So I dressed up for the evening. Blazer with tie was fashionable at the time, but just the thought of it made me want to puke (my rebellious years were not quite behind me). I dug out a smelly, beat-up field jacket that had seen better days on the back of a Bulgarian army corporal and a grease-stained pair of Levis with only a few holes. Hey, I had showered and brushed my teeth (and even girded my loins in clean Jockey shorts). What more could any reasonable woman expect? Giftwrapping maybe?

On sudden impulse, I laid out a coupla bucks for a small bunch of assorted wildflowers on the way over. Seemed like the sort of thing I ought to do, and not too tough on the budget.

I saw her seated at a table in the outdoor cafe where we had agreed to meet. She looked like I might have expected -- brunette, somewhere in her late 20s, attractive, but not exceptionally so. My palms were sweaty. I took a deep breath, and hesitantly walked up to her. "Amelia? No? Sorry." Bzzzt. El wrongo.

A waiter motioned to me. "The lady at the far table thinks you might have lost your way." In the distance, at a table hardly visible from the street, a woman raised her index finger. I walked over. It was a long walk.

"Sit." It was a command. Her soft voice could not disguise the iron underneath. She might have been in her late 30s or possibly even a bit older, but it was like having a cinderblock smashed into my face. A stunner. Tall and and pale blonde, almost albino. Wearing a broad-brimmed hat and a classically-cut feminine business suit. A lady. A statuesque woman, stately, shapely in a manner no longer fashionable... what used to be called "voluptuous." Buxom and large-hipped, very, very curvy hips from what I could see, but her smile, oh, her enigmatic all-knowing smile (would she ever smile for me alone?). And the eyes. Deep, blue-green bottomless eyes. Eyes a man could drown in. I drowned.

She entranced me. A classic beauty, a knockout, a class act. And it frightened me. 'This woman is way out of my league. What could she possibly want with me? And what-the-hell am I doing here, anyhow?'

Lacking anything better to do, I pulled out a rickety wicker-back wooden chair across the table from her, almost knocking it over in the process, and just stood there, panting and goggle-eyed. "So, here I am. Yes, here I am. Uh... Amelia, what a striking name. Amelia, my name is uh... my name is Casimir. Uh... you know me from my letter. I hope."

"Indeed here you stand. You cannot do otherwise. Casimir, ah, my young aspiring paramour-candidate. So grand an entrance. Let us hope your nervousness does not spoil the occasion. I have ordered tea for the both of us. Sit."

The hand clenching the back of my chair was shaking, and she touched me there. A spark passed from her fingertips to the back of my hand, and a flood of warmth washed over me. All anxiety and fear slowly drained away. I felt a deep sense of calm, of relief, and yes, destiny. Wearily I unfolded into the chair. One by one, the flowers silently tumbled to the floor.

For the rest of this story, you need to Log In or Register