The Conspiracy

by "Myer Ottica"


She was handling him, fondling him, running her hands over his body, his legs, pausing to squeeze and caress his erect and pulsing penis at each pass. He was tingling with the most blissful sensations, shivering with pleasure. She was cooing at him.

"You are so gorgeous, so beautiful. Smooth and silky. Such a body. Such a face. So pretty."

She hugged him to her and his penis pressed against the silky-soft material of her pink open-legged panties and her firm breasts in the their silky encasement crushed against his body. She kissed him; on the forehead, on his eye-lids, and his cheeks, on the lips, so delicately they were just whispers.

Her hand encircled his penis again and she squeezed and moved the skin back and forth, slowly, gently.

"It's so tiny and hard," she whispered. "So beautiful."

There was a heat in his loins, a rising heat which was so thrilling.

"I'm going to come," he gasped.

"Oh darling, yes. Come. I want you to. But wait."

She let go of his penis and quickly stepped out of her panties and wrapped them around his penis and started again. Their silky softness, still carried the warmth of her body, raising him to new heights and he felt his legs jelly and his whole body became fluid with a warm flush and he ejaculated into the folds of the intimate garment.

"Oh how wonderful," she breathed, looking down at the creamy, fluid pooled in the pink satin. "I've wanted to do that with you for a long time."

Using a dry section of the panties she wiped him clean. He felt overpowered by the sensations flowing through his body. He watched her remove the panties from his penis. His body was aglow and shivering. Not moving, he watched her cross to the laundry hamper in the corner of the room and drop the panties into it. She flicked her lustrous blonde hair back off her face and opened the drawer of a bureau and took out clean panties and stepped into them. She smiled at him, her blue eyes shining, her pink lips slightly apart. She took a second pair of panties from the drawer and came to him holding them out.

"Put them on," she said in a soft voice.

He stared at them in her hands.

"Your panties?" he said, finding a voice.

"Yes."

He took the panties and stepped into them and drew them up.

"Lovely," she said. "They suit you. That slim, smooth body of yours. You're so lovely. You'd make an adorable girl."

"A girl?" he breathed, looking into her eyes.

"Yes. Let's dress you up and see. My things will fit you I'm sure."

The notion of wearing her clothes, perhaps, even of looking like her was suddenly very seductive but he said nothing and she clearly took his silence as agreement because she took a pretty bra from a drawer. Mesmerized, he allowed her to fit it to him.

This woman, this divine creature whom he called 'Aunt' but who was really his mother's life-long friend. She was the same age as his mother; thirty three. He had worshipped her for years and more so since the onset of puberty.

"Nice fit," she cooed. "But we have to fill you out a bit."

She removed a handful of cotton balls from a jar on the dressing table and pushed them into the bra cups.

"Much better." She smiled at him. "You can wear stockings. I think you'll like them. They're so silky."

She fastened a garter belt around his waist and knelt before him and smoothed sheer stockings up his legs and he nearly swooned. She took out a slip in the same flesh tone as the panties and dropped it over his head and it slithered own his body.

"Oh God," she breathed, "you are going to look just brilliant. How divine."

He was letting her do her thing. He was not objecting. She put a dress on him, a pale blue, short sleeved, short skirted dress with a flaring skirt.

"Sit down here," she directed and he sat, bewildered, on the stool at her dressing table. She took up a brush and comb and played with his hair, He sat silent. When she was done she filled in his lips with a pink lipstick and brushed mascara onto his lashes.

Her proximity, her breasts almost in his face, made him feel short of breath.

She moved away and returned with a pair of white, high heeled pumps and she set them on the floor.

"Slip your feet into these."

He did so.

"Stand up," she said. "They'll feel a little unusual for a moment but you'll get used to them."

He stood in the heels and she moved back from him

"I knew it," she said with excitement. "You're exquisite. Such a perfect girl."

He felt himself blushing. All these compliments...And no one had ever called him a girl before.

"Can I...can I see?"

"Of course." She took his hand and led him, a little unsteadily, across the room to the long mirror.

He was startled by the image in the mirror. She looked a couple of years older than he. She was very feminine and very pretty. He stood staring.

"I'm pretty," he heard himself say in a voice, not his own.

"You are beautiful. I'm so proud. If I had a daughter I'd want her to look just like you."

He was still standing before the mirror, his eyes roaming back and forth over the reflection. His long, silky light brown hair had been combed and teased into a fluffy, feminine style. His breasts. His narrow waist. The skirt about three inches above his knees. His legs, smooth and shiny. His feet in high heels. His eyes and lips looked so different. Without realizing it he smiled and the girl in the mirror smiled back.

His Aunt Carol moved up and stood beside him, still just in a bra and panties.

"You must like her," she whispered. "She's exciting you."

He had not been aware he had an erection. But now he could feel it and see the evidence where it poked at the skirt.

"We'd better get it down I think," she said and for the second time she slipped off her panties and leaned across him and lifted the skirt and took hold of him beneath panties and brought him to a climax and all the time he watched her doing it, not to him but to the girl in the mirror, watched her open-mouthed, thrilling to her attentions, loving it, loving her, loving the girl in the mirror.

A little over an hour earlier, at around nine a.m., she had come, unannounced, into the bathroom where he was taking a shower, dressed just a her bra and panties. Astonished, he had tried to turn his back on her, not to be seen.

"Oh it's okay, honey," she had said. "I don't mind you seeing me like this. And I've seen you lots of time. I used to bath you when you were little. Remember?"

She had turned away from him and began to brush her hair in front of the bathroom mirror. With the hot water flowing over his body he had allowed himself to steal a glance and then to watch. Her pert fanny wrapped in pink satin and lace. The cleavage he could see in the mirror as she leaned forward, brushing. Inevitably he had begun to come erect. She had caught his eyes with hers when she looked up and she smiled and he knew he had been seen. She put down her hairbrush and turned to him.

"Oh Billy, does my body excite you? I'm so flattered." She was mocking him - or teasing him - with her eyes, leaning back again the vanity. He had seen the dark circles of her nipples under the bra and the triangle of darker hair at the base of her tummy through the thin material.

"Are you finished?" she asked.

He had nodded.

She had taken a bath towel from the rack and held it open for him and he had stepped out of the recess and she wrapped the towel around him and began to dry him off. His erected had stayed. The towel brushed against it from time to time. And then, she had toweled it and his balls and taken his hand and led him from the bathroom. And then...

He was a month past his thirteenth birthday and he had known her all his life. She was blonde and sexy and youthful. She was about two inches taller and he was five feet two.

"Leave them on," she said. "You can be my daughter for the day,"

She had replaced her second pair of panties and, still smiling, was more matter-of-fact.

"Leave them on?"

"Sure."

"But we were going to a movie."

"Girls can go to movies as well as boys," she mocked.

"You mean...?"

"Sure. Why not?"

"But people will..."

"What?"

"...know."

"How will they know?"

"I can't act like a girl."

"Of course you can. How much acting does it take? Just be yourself." She smiled. "Go on. You know how lovely you look. You know you like it. Don't you?"

"Well I..."

"Don't you?"

"I don't know. I..."

"Don't you?"

"Yes. Okay, I like it."

"Well then?"

"Are you sure?"

"Absolutely. Now I'm going to get dressed. Want to watch me?"

"Yes."

She dressed, slowly, as seductively as a stripper removes her clothes, commenting as she went.

"Garter belt - stockings."

He thrilled as she drew them up her legs.

"Slip."

He felt it slither down her body.

"A little low necked top so you can see my cleavage. Wouldn't you like to have cleavage?"

Yes, he thought. Oh yes.

"Short skirt to show off my legs but not so short as you can see my stocking tops. Except, maybe, a glimpse when I'm sitting down."

And mine, he thought. MY stockings tops. He was hot from blushing all over.

"High heels to slim my calves and ankles."

He was standing there, feeling the arch of his feet, elevated by three inch heels.

She turned to him and flashed a smile.

"How do I look?"

"Beautiful."

"Oh thank you...er...Jenny."

"Jenny?"

"Sure, You like Jenny for a name?"

"I guess."

"Okay then Jenny it is."

She turned to the dressing table and began adding items of jewelry. He turned back to the mirror. The girl - Jenny - was still there. Except he knew the girl was him. And suddenly, inexplicably, irrationally, he felt a wave of pure happiness and excitement passage through his body and he smiled again.

"Can I...wear some jewelry?"

"Of course. Come over here."

She clipped a pair of earrings to his ears, added a bracelet and a ring. She spent another few minutes playing with his hair and then sprayed it with a light lacquer to hold the style. She dabbed a perfume - Chloe - behind his ears. She took out a small blue leather purse with a gold chain and put a lipstick into it and placed the chain over his shoulder.

She stood directly in front of him, examining, smiling.

"You don't look old enough to be my mother," he said.

"Okay then you're my niece. Just call me Aunt Carol as usual."

Niece. Daughter. Girl. She. Her. Female, Feminine. It didn't matter now. They all sounded extravagantly appealing.

She looked at her watch.

"We can go now. We can have a bite to eat before the movie."

Go! Oh God! His knees jellied.

"Uh...are you sure?"

"Yep. Oh wait. Walk back and forth for me."

He did so. She gave him some pointers on walking in heels. He improved.

She giggled. "You're perfect."

Quaking, he followed her out the front door of the house.

He had arrived at her house the evening before, dropped there by his mother who was going east for four days to visit her sick mother. Carol Turner lived only a couple of blocks from their house in Newtown. In the few minutes they had together before she left and while Billy was exploring the bed room, Carol and Billy's mother kissed passionately.

"I'll miss you," Carol said.

"It's only four days."

"I know. I'll miss you anyway."

"What do you plan to do with him?"

"It's time."

"I know. Be gentle though."

"You know I will."

"Yes. He's ready I'm sure. I'm sure he'll be interested. Maybe even keen."

"She, darling. Think of her as she."

"Yes. Oh Carol!"

They kissed again.

"I want to fuck you," Claire Bailey said.

"I know. It's only four days."

Claire laughed. "I just said that."

"Go now."

Claire called good-bye to Billy who came to the door to kiss her.

"I love you Billy," his mother said, kissing him on the lips in a most unmotherly fashion. "You're so pretty."

And he was. Billy Bailey had the cherubic, androgynous face of an angel, framed by shoulder length hair, kept silken and gleaming by at least three shampoos a week and a daily brushing. The style he usually wore was unisex but it was just as easy to turn it into a girl style, as Carol had proven, with some back combing to give a little extra bounce and fullness. He had flawless skin, the color of whipped cream, almost eyes, full lips and a pert nose. His eyebrows, plucked regularly since he was eight, were finely arched. His narrow shoulders sloped gently to extend into slim arms and end with small hands and long, slender fingers. His body was straight, his tummy flat and his hips and buttocks nicely rounded. His legs were slender with shapely calves and slim ankles.

Everyone acknowledged he was pretty - not handsome, pretty - and some came right out and said he was much too pretty to be a boy. There was an element in Billy which caused him to believe this. He was very vain; this trait had been developed and encouraged by his mother who taught him, carefully, the benefits of daily personal grooming. he almost never passed by a mirror without checking how he looked.

Claire Bailey also encouraged in him an interest in clothes and fashion. Not boy clothes, female clothes. He shopped with her and was invited to comment on what she bought and wore - even to be her dresser.

In short, having detected this spark of femininity in her son, Claire determined not just to allow this element to develop but to aid this development in every way she could.

By the time he was thirteen Billy was well versed in all things feminine. All that was needed then was to seduce him into the cross-over phase. Claire and Carol had decided that the way to achieve that goal was to appeal to his vanity - to turn him on to his own sex-appeal.

A dress, makeup, high heels, lunch and a movie. That's all it took. By the time they were driving home Billy was the happiest he could ever remember being. Disregarding his vanity - he had, after all been very pleased with the way he looked - the touch of satin and silk against his body, the sensuous flow of a skirt around his thighs, was heady stuff. He loved it.

But Carol wasn't finished yet. Not by a long shot. She had three days - and nights - left.

At bedtime Carol had no trouble in getting him to wear a long, silken nightgown to bed. And no trouble in getting him to share her bed with her. Whereupon she proceeded to introduce Jenny to the delights of woman to woman sex - sex without penetration. One of the things Claire most loved about Carol was her large clitoris, only a little less than an inch long when she was aroused. Given that Jenny was only a little over two inches fully erect, Carol had no difficulty convincing Jenny to think of his penis in rather different terms than he had done before. And when she set up the position for them and when she took him into her mouth and he took her into his he was in such a state of heavenly bliss he could not imagine making love any other way, Considering he had only discovered masturbation a month or so before and had probably only pleasured himself in this way six or seven times, three orgasms in one day at the hands and mouth of a woman he adored, seemingly as a reward for wearing a dress, which was in itself a pleasurable enough activity, had a profound effect.

So when he awoke the next morning. wearing a girl's nightgown, with his new lover snuggled against his back and holding and gently manipulating his "clitoris" and when, seeing him awake, she whispered in his ear; "Would you like to wear a dress again today?" he had no hesitation in replying.

"Oh yes please."

William Bailey was born out of wedlock. He would never know his father, who in fact, was a one night stand Claire had picked up in an exclusive down-town bar expressly for the purpose of trying to conceive.

At the time Claire was living with Sandra Capriccio and the pair had hoped for a girl-child and were, at first, disappointed in the beautiful boy baby who was presented to Claire on the morning after a seven hour labor. But a baby is a baby and lovable in any form and when Claire and Sandra took the child home they dressed it in pink and in dresses for the first four years of it's life. Claire named the baby William because it was the first name she thought of but they called it Billie and even spelled it this way until pre-school when the thought of continuing to raise the child as a girl was just too outrageous and Billie became Billy and gave in, crying, to pants and shirts.

About this time Claire and Sandra decided to separate, amicably enough, and Carol always a friend but not until now a lover, consoled her friend, firstly on the divan but later in bed. She never became a live-in lover but she became a "steady".

By the time Billy was ten, sweet and delicate and gorgeous and quite feminine, really, the idea of him growing into bearded manhood was more than Claire could bear. Months of torment followed as Claire and Carol devised their plan.

On the second day of his conversion Jenny, joyously embracing the experience, was wrapped and unwrapped in a bewildering diversity of Carol's dresses. skirts, blouses, jackets, coats, sweaters and, of course, underwear. With each outfit Carol explained where and when it might be worn and for what occasion such and such might be suitable. Jenny already had a feeling for some of this.

Twice during the day Jenny produced an erection and Carol ministered to him so that he would be saved the embarrassment of the small tent-like projection spoiling the line of his skirts.

That night Carol took him to her bed again.

On the third day Jenny was exhaustingly instructed in deportment, makeup and hair. It was never going to be enough but it was a start. Carol kept him in tight lycra panties all day so although an erection threatened, it could not come to attention.

It was permitted to stand free that night in bed.

On the fourth day Jenny and Carol rose early and dressed for the day. Carol had Jenny choose his own outfit, a pink linen, sleeveless mini-dress with a matching bolero jacket which he wore with white sheer stockings and pink high-heeled pumps. Together they went shopping.

Carol insisted Jenny should talk with sales clerks and waitresses and slowly the shy, pretty young lady opened up.

The first thing they bought was a divine, clingy little white jersey dress with a short skirt, cap sleeves and a shallow scooped neckline.

Admiring it Jenny said: "That will look great on you."

Carol said: "Oh it's not for me, darling. It's for you."

Jenny stared at her.

"For me. You're buying a dress for me?"

"Uh huh."

"But...how...when will I wear it? Will you keep it for me so I can wear it when I visit?"

"Darling girl, you won't have to leave it my place. You can take it home with you. And there will be others like it."

Perplexed, Jenny continued to stare.

"Sweetheart your Mommy knows what we're doing. We're preparing you to meet her tonight when she gets back. When she can meet you as her gorgeous daughter for the first time."

"Mother?"

"Absolutely."

In a complete daze Jenny followed Carol around the Mall, trying to make sense of what he had just learned. His mother was going to see him as a girl. He was both awed and thrilled by the idea. He really had no idea how his mother could know to expect to see him that night. Unless...

In a dreamworld the ideas wandered around in his head for the rest of the day as they completed their purchases for his first and only complete outfit of female attire. After the dress came gorgeously sexy, high heeled, strappy sandals; a pair of sheer white stockings, no more than a whisper of material; a heavenly white lace and lycra panty-girdle and a matching padded bra; a divine silk-satin mini-slip with delicate lace edging. They bought a gold bracelet watch, a single strand gold neck chain and a pair of gold hoop earrings which would need his ears to be pierced, which he briefly puzzled about.

Until after a light lunch when Carol wheeled him into a lavishly appointed beauty salon where for the next three hours he was pampered, plucked and preened to emerge with hair a shade lighter, framing his face in a gentle inward curve, with a full make-over which left him dazzled - and aroused - by his own beauty, with the hooped earrings dangling from pierced ears (and instructions on how to care for them), with porcelain nails one inch long and glowing in rich pink, wafting along on an aroma of Dioressence and womanhood, with a smile on his face which may well have become permanent.

"And now he was a she.."

They returned to Carol's house where final preparations were undertaken. He was stripped naked whereupon the erection which had been threatening all day sprang to vigorous life.

"Darling let me help you one last time,"' Carol offered and went on her knees and took his "clitoris" into her divine mouth.

When she was done he was glowing and tears threatened to spill from his eyes. She dabbed them away carefully.

Trembling at the very notion of it he dressed in the bra, the panty-girdle, the stockings - oh! heaven - the sensuous slip and the oh, so sexy shoes. Still disbelieving, he consulted the mirror for an opinion and the mirror told him he was - perfect. And in his mind he aid to himself for the first time...I'm a girl.

The phone rang at precisely seven fifteen and Carol reported to him that Claire was home and anxiously waiting. They drove there in under five minutes.

Claire Bailey answered the door and stood, mouth agape, gasping.

"Oh my God!" was all she could say.

"I wont come in," Carol said. "I think you two should have time alone. I'll see you tomorrow."

Before Claire could catch her breath to protest, Carol was gone. Claire continued to stand at the door staring.

"Can I...can I come in?" Jenny asked.

"Oh! Oh! Of course, darling. I'm sorry. I was spellbound."

They entered the house. Jenny thought her mother looked a little tired, frazzled. She was also clearly nervous. Claire picked up a cigarette and it.

"Did you...have a nice time...Jenny?"

"Oh Mommy it was lovely."

Claire waved the cigarette distractedly.

"Oh God! I feel so dowdy. So inadequate."

Jenny put down her new white leather handbag. In it were her shade of lipstick and eyeshadow, mascara and blusher. And Carol's parting gift...a calf length, sheer white nightgown with tiny white bikini panties.

She stepped up to her mother. In the high heels she was about equal height. She put her arms around the older woman and pulled her gently to her and kissed her gently on the lips.

Claire began to soften and et out a gentle moan. Then suddenly she stiffened and broke the kiss.

"Oh God! Jenny I can't..."

"Can't what Mother?"

Jenny kissed her again. Claire squirmed for a moment then gave in.

Jenny lowered her right hand and gathered up her mother's skirt until she could reach beneath it and slipped her hand down inside her panties and cupped her hand over the triangle at her crotch and maneuvered her index finger into the cleft and moved it back and forth very gently.

Claire moaned.

Jenny said, very softly: "Go to the bedroom and get undressed and get into bed."

Obediently Claire left the room.

Jenny undressed quickly and put on the bikini panties and the diaphanous nightgown. She went to the bedroom and stood for a moment in the half light at the door. She caught her mother's eyes.

"Isn't this what you wanted Mother?" she said.

Claire did not answer but watched Jenny with warm eyes from over the covers.

Jenny crossed the room.

"You only like girls don't you Mommy?"

Claire's eyes answered for her but she gave an almost imperceptible nod.

"I'm a girl," Jenny said, and slid in beside her mother.

The End

© 1997 "Myer Ottica" & Michelle Johnson