St. Clair Ladies Circle: Beginnings

I Become A Woman

(Author's Note: I Become A Woman is the true name of this chapter. Since Literotica's protocols do not permit long titles, I shortened the title used by Literotica.

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My name is Valerie. Well, my en femme name is Valerie. For the past two years I've lived as a woman—dressed as woman, presented myself to the world as one, think like one. This started nearly three years ago. My wife and I belong to an exclusive sex club known as THE ESTATE. We use our membership for me to indulge in my fetish for crossdressing. My wife did not approve of this fetish, but went along with it, especially if I restricted it to our visits to THE ESTATE. As I became more accomplished at make-up, deportment, and fashion we began indulging in more and more of the activities at THE ESTATE for couples like us. Naomi and I were befriended by Helga and Marvin (en femme Thelma) St. Clair. Helga had devised an elaborate ritual for Thelma's defloration, and some dozen others had since gone through it and were members of a special clique at THE ESTATE. Inevitably, the time came for me to complete my role as a woman—to lost my anal virginity to a man!

The man chosen to perform this rite was

This was an elaborate bridal shower with all the transvestite husbands that William had deflowered, dressed as bridesmaids, and their wives dressed as matrons of honor. Each bridesmaid told her own experience with William, each ending with the revelation they had never been able to perform with women as a man again. At this point, Helga, the dean of the matrons, informed me that I didn't have to go through with this, citing THE ESTATE's rules against rape. Although we no longer were on THE ESTATE's premises, the St. Clairs abided by most of its rules even off-premises. Helga then informed Naomi that none of the bridesmaids who had been deflowered by William had ever been a husband again in the biblical way, and that she should consider this before we went any further.

Both Naomi and I were apprehensive. We knew most of the bridesmaids were living their lives away from THE ESTATE as women. We thought this was just their personal choices. Now we were informed that the experience with William was so traumatic that they had been "womanized:" turned into sissies so thoroughly that they never could function as men sexually, or even at work or socially. For most of them, they were so financially comfortable it took very little to change their lifestyle to accommodate their changed status. For the others, some continued the masquerade of being men, while others made the adjustment to female jobs, or being female in their former lines of work, although at different firms and usually in different cities, or even states. THE ESTATE's connections and membership, not just the clique of William-womanized sissies, made this adjustment quite easy.

"In for a dime, in for a dollar" I thought. Naomi agreed, reading my mind. The shower then proceeded to the unwrapping of gifts. There were the usual boudoir gifts: baby doll nighties, thongs, sleeping gowns of various lengths and colors, lingerie, oils and gels. But it was Helga and her spouse's gift I found most ominous: five paid sessions with a marriage counselor!

"We like you and Naomi," she explained. "We would hate to see your marriage break up. And that has happened to most of William's turnouts. What you see here," she turned and waved her hand at the assemblage, "are those who have adjusted to their situation. Of course, there is always the chance that you will be the first to survive and continue to function manfully."

Naomi and I looked at each other, the anxiety showing on each of our faces. We nodded to each other, this also signaling acceptance to the group. With some fanfare, William was introduced, brought in through the hallway leading to the bedroom. I could see why he was chosen. Tall, well-built, very handsome, he was every woman's—and sissy's—dream. He was wearing dark pants, a starched white shirt, a cravat, and a smoking jacket. He strode into the room, a cross between a smirk and a sneer on his face. All the bridesmaids looked at him, then away, nearly all blushing. Only a look from Helga and two or three of the other matrons brought the smirking sneer into a leering smile. William was still an employee of THE ESTATE, while the rest of us were members and guest. Even away from THE ESTATE, rank and place must be respected!

Helga assumed responsibility for the rite at this point, like the chief witch of a coven. Given that there were thirteen of us present, this somehow fit.

"Valerie, this is William, your husband for this night. William, this is Valerie, who you will make a woman this night. Valerie, William, show your acceptance of this nuptial by kissing."

This was the substitute for the marriage ceremony. I was not sure what to do. I had never kissed a man before, although I had kissed Naomi when she dressed as a man for various occasions. William was not uncertain at all. He stepped forward and took me in his arms like I was a rag doll and lifted me bodily into him as he took my upper lip between his and sucked. Before I knew what was happening his tongue was inside my mouth, one of his hands was pressing my back between the shoulder blades and the other was on my ass, pushing me into him.

I am only a few inches shorter than him, and with heels that made us equal in height. My build was about the same, although he had a much better developed upper body. I probably could have broken the clinch, but for some reason I submitted. Submitted! I just opened my mouth and let his tongue have its way. As he pressed his body into mine, I threw my arms around his neck and kissed him back. In the background I heard applause. William began grinding against me, letting me know the size of his member. For the first time that night I knew fear. If what I felt against my own pubic area was real, I was going to be split in two!

I released my hold on William letting my hands drift to his chest. I pushed gently, and he broke the kiss. I looked around at the others, shamefaced. Naomi looked at me with a mixture of shock and surprise. The other matrons smiled knowingly, as did the bridesmaids. I stepped back from William, and waited.

Helga came up and kissed me on the cheek. "I see we won't have some scared bride tonight." Naomi then came up and kissed me fully on the lips, further smearing my lipstick. She broke the kiss and smiled at me, giving me her blessing.

"Valerie," Helga began, pulling Naomi away. "You should show your husband how much you plan to enjoy this night. That smoking jacket looks awfully uncomfortable. Why don't you help him remove it?"

I unfastened the sash at his waist, then moved behind him to take the jacket off of him. One of the bridesmaids took it from me.

"Now, Valerie," Helga continued, "help William with his shirt and cravat."

I came around and faced William who had already undone the cravat. I unbuttoned his shirt, not really believing the red-lacquered fingers that was undoing a man's shirt belonged to me. When I reached his pants, I stopped.

"Go on, Valerie," Helga encouraged.

William stood there, his hands on his waist just above his pants tops. The smirk-sneer had returned, looking somewhat comical with my lipstick on his lips. I unfastened his belt and started to pull the shirttails from his pants.

"No, Valerie," Helga chuckled, "Don't pull his shirt out, pull his pants down!" The room tittered with laughter.

I unzipped his pants and pulled his pants down, dropping to my knees to finish the job. William wasn't wearing underwear, and as I pushed his pants down his legs revealed was the monster that was to deflower me. It hung down like the proverbial third leg! At this point, Naomi stepped up behind me, placing her hand on my shoulder.

"This is what you wanted, Valerie. To be a complete woman for this weekend. Well, this is your wedding night, and your husband stands before you. Do you remember what I did for you on our wedding night? Now you're the bride."

On our wedding night, Naomi had stripped me when we were in the bedroom, then, kneeling before me as I was before William, gave me a slow and loving blow job, in effect worshipping my cock. Of course, she had given me blow jobs before, and my cock was no stranger to her cunt. But it was the ultimate of submission the way she did it. And Naomi was not the submissive type!

I looked around the room, sensing expectation in the air. I looked up at William. His grin was back to the smirk-sneer. From my position, he looked large and ominous, standing over me. I looked back at his cock, when I felt a hand on my left shoulder, and its arm across the top of my shoulders.

"Just put the palm of your hand underneath the head, honey, and bring it to your mouth."

I did as instructed. As soon as I touched it, it jumped as if alive. The term "trouser snake" immediately came to mind. I slowly lifted my hand, bringing the head to my face. It looked angry, being all purplish with its one eye.

"Kiss it, Valerie," my wife instructed.

I did, leaving a large lipstick print along the top.

"Now stick out your tongue and run it along the outline of the lipstick print you just made."

Again I followed my wife's instruction.

"Now slide your tongue along the slit from top to bottom." I did so. "As you slide your tongue along the underside of the head, open your mouth and take as much of him inside as you can."

Again, I followed Naomi's instruction. William is big, nearly as big around as the proverbial soft drink can. I was only able to get about half the head in, when the room burst in applause. I then felt two strong hands—masculine hands—grip my head firmly. The cock in my mouth began to grow, pushing my jaws apart until they ache.

"Easy, William," I heard Helga say. "Remember, she's a virgin to cocksucking too."

I felt William back away. By now his cock was fully rigid and pointing straight from his crotch to my mouth.

"Place your left hand around the shaft, just in back of the head." This time the voice was of one of the bridesmaids. I did as instructed. "Now just work the head. Lick it, suck on the tip, kiss it. Whatever you feel comfortable doing."

I did everything. There was now a general murmur in the room. Everyone was offering her suggestions, while a few made snide comments about this not being my first time sucking cock. Without warning, William grabbed my head so that my jaw opened wide, stuffed as much of himself into my mouth as was possible, and came.

And I mean came! One second my mouth was full of cock, the next full of cum! "Just swallow!" a chorus of voices said. I did. I nearly choked. Cum coated my lips and chin, and had dripped to the bodice of the corset, and was dripping onto the skirt of my outfit. William just stood there, cum steadily coming out of his cock.

"Well done, Valerie," I heard Helga say among the din. "If you don't mind, we'll let the other ladies finish him.

I was pulled away, to be replaced by Thelma. She practically jumped into the spot I had just vacated and swallowed William's spurting cock. No cum escaped her lips, but after a minute or two, another bridesmaid rather unceremoniously pulled her away and replaced her. There were five bridesmaids altogether, and each took her turn at William's cock. I watched in amazement, for William never seemed truly drained. As I looked around at the other matrons, I noted a look both of longing and of satisfaction as they watched their husbands suck cock. When they were finished, there were six sissies with cum over their faces: cheeks, lips, mouths, chins, noses.

Helga then stepped up to Thelma and French kissed her. She then looked at Naomi. Naomi stepped over to me and pulled me to my feet, then Frenched me, tasting William in my mouth. When she broke the kiss, all the matrons and bridesmaids applauded again.

"Welcome to the club, Naomi," Helga smiled. "Not every wife can kiss her husband once she has seen him suck a cock. Especially when the cum of that cock is in her mouth. Matrons, you may kiss your husbands!"

With this, the other four women Frenched their bridesmaid-husbands. William was now in full glory, his cock standing its full ten inches pointing upward. Somehow while his cock was being sucked by the others he managed to step out of his pants and shoes, and stood there bare except for his socks. The matrons and bridesmaids then looked at me, then at William, then at Helga. She nodded to William, who took my hand and led me into the room from which he had entered. It was large; I later learned it had been a rather spacious den in the St. Clair's large house, and had been converted into a sex chamber where special ladies like me are made into women. All of the bridesmaids had been deflowered there. In the center of the room was a large four-poster bed of some dark polished wood. It had once been a canopied bed, but the canopy had been removed so that all could see the proceedings. For my defloration was not to be a private event. No way! I was to have my ass reamed while 18 eyes watched, and at least six cameras recorded it from various angles. The bed was also on a dais, with three steps leading to it, while there were a series of loveseats forming a semi-circle around the sides and foot of the dais.

William led me to the foot of the bed, then turned me to face him as he unlaced the corset. As he unlaced me, the bridesmaids each took one of the loveseats while their wives procured camcorders or activated the other video equipment in the room. When he was finished, he roughly pushed the material away from me and kissed me again. As he did so, he pulled the strings at the back of the skirts and they all fluttered to the floor. I just stood there as he undid the garters then threw the corset into a corner of the room. I stood there: wig on my head, garland headpiece, stockings and heels. My cock had shriveled so that I did not even think of it.

William then pushed me up the steps of the dais onto the bed. The mattress on the bed was not flat, but had been especially made so that my ass was on a rise while the rest of me sloped toward the headboard. William positioned me so that I was on my back, my legs splayed, my asshole exposed. He then sat on the edge of the bed and removed the rest of his clothing. As he did so, I took in the scene around me: three matrons with camcorders, one at each side, and one at the foot; their spouses dressed as bridesmaids sitting in back of them on loveseats. My wife was in a loveseat at the left side of the bed, right in line with my hips. The fourth matron I did not notice, but she was making sure that the other video recording equipment was functioning properly.

"Naomi," Helga intoned. "Do you consent to this act?" Naomi nodded. "Then you must prepare Valerie." She then produced a large tube of KY lubricant and handed it to Naomi.

Naomi climbed onto the bed and applied a finger tip of lubricant to my asshole.

"She's gonna need a helluva lot more than that, sweetie," one of the bridesmaids quipped, followed by tittering.

"Use it all, dear," said Helga in a tone that quieted the room.

I next felt a nozzle enter my ass then a copious amount of lubricant. The nozzle was removed and I saw my wife sit down shamefaced. William strutted around the bed like Achilles dragging Hector's body around the walls of Troy. As he came to Naomi he stood there, his giant cock pointing at her.

"Use the remainder of the lube on him," Helga commanded.

Naomi did so, greasing up William from the tip of his cock to his pubic hairs. I thought he was going to cum again. When she had thoroughly lubed him from balls to pee hole, he turned to me, climbing on the bed and positioning himself between my legs. He placed his hands on my hips, pressing his cock against my hole. He then snapped his hips and the head was inside me. He snapped his hips a second time and it breached my sphincter.

"Aieee!" I cried. The pain was unbearable, yet I bore it. Or rather William bored me. He moved his hands up my body to my waist and snapped his hips again. I kept screaming, seeing nothing through the pain. What I tell you now is from viewing the videos of that night. William kept snapping his hips, each time sending another inch or two into me until his balls were against my ass. William then lay down on me, his arms framing my head. Once he had settled into position, he began a long withdrawal until only the head was inside my sphincter, then a long push inside until his balls kissed my ass again. In and out, in and out for fully ten minutes. I just lay there like a rag doll, being ravished.

The video cameras that was overhead or at a distance—I'm still not sure where they were located—showed a woman in a garland headpiece, stockings and heels, being fucked by a man. The cameras at my hips had the same view as my wife: one long, thick cock going in and coming out, the lubricant becoming mixed with feces, and blood. The one at the foot of the bed gave a bedbug's eye view of my ass being reamed.

One of the cameras concentrated on Naomi's face. She was horrified at what was happening to me, yet either powerless or unwilling to intervene. Another camera concentrated on my face, taking in every grunt, grimace, yell, blanche or other facial contortion. I must have yelled or moaned or groaned during the entire defloration. Other cameras panned the matrons and bridesmaids, whose expressions ran the gamut from sympathy to gloating. After the initial onslaught, two of the bridesmaids approached the bed from either side, taking my legs and bending them so that my knees were at my chest. They then sort of rolled me on my back so that my ass was more upturned. At this point, William covered my mouth with his and began pistoning in and out of me faster.

The pain was excruciating, bringing me out of my delirium. I now realized the kiss was not affection, just his muzzling my mouth with his. As he began this more rapid second assault, I instinctively grabbed the sides of his body to brace myself. This elicited another round of applause. The applause spurred him on and soon he was sliding in and out of me rapidly. After what turned out to be another fifteen minutes, he stiffened on top of me and came … and came … and came!

He lay on top of me for a full five minutes, pumping shot after shot of cum into me. When he became less turgid—he never actually became soft—he pulled out of me with an audible "plop." The room burst into applause as William swung to the right side of the bed. A bridesmaid came up and began washing his cock. An extended view of my extended hole with the mixture of cum and cream flowing out was video recorded.

William, cock cleaned and rampant, stood at the side of the bed, arms folded triumphantly, looking down at his cockmanship. He and all the rest knew that I was not to be the lady who remained a man. My hole was now permanently widened; anyone who viewed me naked from the rear would know I had been fucked in the ass by one helluva cock! As I lay limp on the nuptial bed, they all knew I would never function as a man with a woman again. I was a William turn-out. I had been womanized!

The two bridesmaids who had held my legs then escorted me to the adjoining bathroom, where one prepared a bath and the other removed my soiled stockings, shoes, wig and headpiece, then helped me into the bath. As they washed me, Helga and Naomi came in to watch and to talk.

"I'm sorry it was so rough on you, Valerie," she sympathized. "It's clear you're not going to be the first survivor of William. Too bad." The bridesmaids finished washing me, and were now drying me. "Still, you and Naomi should try to have sex as man-and-wife tonight. I strongly advise you do so. … But I also suggest you don't get your hopes up too high. Thelma screamed like that when William first fucked her. So did Antoinette, Hermione, and Karen. It comes with the territory."