Author's note. I wrote this story some years ago and have now re-written parts of it and tidied up the grammar and punctuation. If you haven't read it before I must warn you that it contains explicit scenes of sexual activity, cross-dressing and just a hint of incest.

 

The Rehearsal

by

Belle Gordon

 

Chapter One.

The instant 14-year-old Christopher DeCoursey walked into my drama class I knew I had found my Juliet.

He moved with grace and poise, without slouching, as most teenagers seem to do. He kept his shoulders back and head erect. He was a little taller than average for his age. He had the classic good looks of a catwalk model; high cheekbones, wide set cornflower blue eyes, full pouting lips, strong white teeth and a long elegant neck. His fair hair was fashionably long, full-bodied, and wavy. His eyebrows arched gracefully, looking suspiciously like they'd been plucked, but they could have been be natural. He was slender, but not thin. He appeared quiet and reserved, almost aloof. He sat quietly at his desk, his hands, with their manicured fingernails, clasped together on the desktop. He didn't talk much, nor horse about with the other boys.

This was my second year teaching drama at The King Henry VII, Grammar School for Boys. I taught part time, three days a week, and as it was the start of a new term this was my first opportunity to meet this class. The headmaster had made it clear at a pre-term staff meeting, that he would like to see some Shakespeare performed this year. The choice of play he would leave to me, but he did not wish to see 'any modern stuff.' The problem, as I had pointed out, with staging plays in an all boys school, especially teenage boys, was finding someone to act the female parts. And so far as I knew all of Mr. Shakespeare's plays featured women. However, as soon as I saw Christopher, I knew that if I could persuade him, the female lead would be cast.

When the boys had taken their seats and settled down I introduced myself, Salvador DiMarco, and they, in turn, told me their names. I announced that the end-of-year school play was to be performed by this class and that it would be staged immediately before the Christmas holidays. I informed them that they would be performing Shakespeare's Romeo and Juliet; the roles would be assigned later. My announcement provoked a mixed reaction; some enthusiasm, some gloom. For the remainder of the lesson we discussed the play and read sections of it.

When the end-of-lesson bell sounded I asked Christopher to please remain behind for a moment. He remained in his seat toward the rear of the classroom and I walked over and perched on the edge of a desk across the aisle from him.

"Do you like acting?" I asked. "I noticed you were very attentive and you seemed very interested during our discussion."

Throughout the period Christopher's eyes had rarely left me. Whenever I had looked in his direction he was watching me. I had tried not to focus on him too much, but I found it very difficult to ignore him. My attention continually returned to the boy. From the moment he had walked into the room I'd been conscious of a sexual attraction for him, and whenever I'd looked at him I felt a stirring in my groin. I'd had to concentrate fully on the lesson otherwise, I was sure; I'd have got an erection.

"I've never done any," he said. His soprano voice had a sweet, piping sound that clearly had not broken.

"Would you like to have a go? I think you would make a perfect Juliet."

He thought for a moment. He didn't immediately protest that he couldn't possibly play a female role, as I had expected, then said, "I don't know. I'm not sure I could learn all the lines. I'm not very good at memorising things."

"Don't worry about that." I said. "If you agree to play the part I'll give you extra tuition to help you learn them. We could practice together in the evenings at my house."

His big blue eyes looked deeply into mine. I felt my knees go weak and my cock twitched into life. Suddenly his eyes dropped and he stared directly at my crutch where my hardening penis was plainly outlined in my trousers. Smiling, knowingly, he looked back to me and said, "OK, Sir, I'll give it a go, if you promise to help me."

"Great!" I said. "If you're free this evening why don't you come to my house and we can start learning the part."

"I'm afraid I can't tonight. You see, my mother's a demonstrator and I have to go and help her."

"What about tomorrow then?"

"Yes, I could come tomorrow."

"Here's where I live." I said. I scribbled my address on a slip of paper and handed it to him. "Do you know where that is?"

"Yes. I live quite near there."

"OK, then come over after you've eaten at about eight o'clock and we'll see how we get on."

He carefully folded the paper and put it into the pocket of his blazer, then picked up his book-bag and turned to leave. Pausing at the door, he turned and looked back at me, then deliberately dropped his eyes and stared at my crutch. After a second or two his eyes slowly lifted and he looked deeply into mine. His face broke into the sweetest smile I'd ever seen. I was smitten.

 

Chapter Two

I didn't have any classes the next day so I spent the time cleaning my house. I'd lived alone since my wife had walked out on me two years previously, when she'd begun an affair with another man. We had been married for less than a year when she'd left me, and in retrospect, we were probably too young and immature to marry when we did. After divorcing Jean I found that the freedom I gained from a bachelor's life suited me; it gave me the liberty to indulge my secret desires.

When I'd finished the house chores I walked to the local supermarket and bought groceries I needed. I also purchased two bottles of white wine and a large bunch of flowers. Returning home I arranged the flowers in vases and set them around the living room. Their fragrance soon filled the air.

After a light lunch I decided I'd take a bath. I filled the tub with hot water, added lavender oil and bubble bath to get the water nice and foamy. Striping off my clothes I walked naked into the bathroom and slid into the water. As I luxuriated in the silky water I felt the tiny, stubbly hairs on my legs, which reminded me I hadn't depilated for a while. I reluctantly left the sensuous warmth of the tub, stepped into the shower stall, and spread the cream over my body. I waited the required time, and then rinsed it off, along with what little body hair I had.

I'd started denuding my body of hair soon after my wife left. I noticed one hot afternoon that my armpits smelt sweaty, and wondered if removing the hair would solve the problem. The trouble with shaving, I soon discovered, was that the hair grew back thicker than ever, but I liked the feeling of my hairless axilla, so I persisted with it.

Then, one afternoon, while idly watching television, a commercial caught my attention. Two women were discussing the smoothness of their legs. One said that because she shaved her legs the hair grew back dark and bristly; the other then explained the benefits of a certain depilatory cream. A light flashed on in my brain and I immediately went out and bought a jar of the stuff. I applied it to my armpits, waited the requisite time, and was amazed at the result. Pretty soon, I was treating my legs, then my arms and chest, then my whole body. The resulting hairless skin felt very sensitive and erotic. Should anyone ask me about my hairlessness, I'd explain I suffered from alopecia, but it was unlikely anyone would.

I'd been treating myself regularly ever since, and now the hair hardly grew at all. Once a month was usually sufficient to keep my body perfectly smooth and hairless. I also began using it on my face to eliminate my beard, although for some reason it didn't seem to work so well here, and on my pubic hair, leaving only a small tuft at the base of my penis.

Returning to the bath, I added more hot water and turned my thoughts to what I should wear this evening for Christopher's visit. I had begun to cross dress again after my wife's departure, something I hadn't done since I was a teenager, and a secret she was unaware off, and now I spent most evenings and weekends dressed en-femme. I usually wore a bra and panties, with either pantyhose or stockings, under a dress or skirt and blouse, but tonight I'd have to be more discrete. I did not want to alarm the boy by being too overtly feminine, but nor could he resist the urge to wear something sexy.

I decided to wear my ankle-length caftan. It was a relic from the hippie sixties that I'd found in a charity shop. It was made from heavy royal blue silk and was richly embroidered with flowers and swirling patterns. The sleeves were voluminous, much like a cartoon wizard's with a contrasting orange silk lining. Twenty-five mother-of-pearl buttons ran from the waist to the military style collar that fastened tightly under the chin. It was extremely comfortable to wear as it hung loosely from the shoulders and left the body un-constricted.

Having decided on the caftan my next problem was underwear. My first impulse was not to wear lingerie in case Christopher somehow saw it. Then I reminded myself that I could wear anything he liked, or nothing at all, under the caftan, and no one would ever know. So I'd go the whole hog and wear the sexiest things I had.

With the bath water cooling and my skin starting to wrinkle, I stepped out and dried off with a large fluffy towel. I dusted my wonderfully smooth body with Christian Dior mimosa talc; I loved the sweet flowery scent. Naked, I padded back to my bedroom, and opened the bottom draw of the dresser. Inside was the feminine underwear I'd accumulation from various sources. Mostly, I'd obtained it by mail order, or from charity shops, but some I'd bought, with heart-thumping excitement in anonymous department stores. I selected my favourite black satin basque with the tiny red roses. Lace trimmed the bra cups, the front panel, and round the bottom edge. I also laid out matching bikini panties, flesh coloured nylon stockings and a full silk slip, also black, with a lacy overlay on the bust.

The sight and feel of feminine lingerie invariably has the same effect on me. My pulse speeds up and my cock hardens to an erection. And now was no exception. I lay back on the bed and draped the lovely clothes over my body and face. Wrapping the panties round my cock I slowly masturbated.

Closing my eyes, I imagined Christopher dressed in the very things I was planning to wear this evening. He was standing with his legs slightly apart and I was kneeling on the floor between them. The panties were pulled down to his thighs and his erect penis stood out before him. Reaching forward, I took his lovely prick in my hands and brought my lips to the swollen head. I opened my mouth wide and took the whole length into my throat. I sucked the hard cock till I heard a groan from his throat and felt hot come spurt into my eager mouth.

Slowly, I realized that the groan had come from my own throat, and the cum in my mouth was my own. My ejaculation was so powerful that sperm covered my face and chest. The fantasy had been so realistic and the orgasm so intense that it took me several minutes to recover.

As I cleaned myself in the bathroom I saw with alarm that I didn't have much time before Christopher's arrival. I threw the soiled panties into the dirty clothes hamper along with the other items of lingerie awaiting washing and headed for the bedroom. I slipped my arms into the shoulder straps of the basque, and with practised ease reached around my back and fastened the hooks and eyes. As always I loved the restrictive feeling of being tightly bound in exotic materials. When the last hook was joined together I tugged the garment down to settle it properly. I took a deep breath, expanding my chest to the fullest, and as I slowly exhaled, felt the elasticated material at the sides hug me in its sensual embrace. Sitting on the bed I rolled the stockings up my legs and fixed them to the four suspenders attached to the bottom edge of the basque. The tug on the stocking tops as I stood produced the beginnings of another erection and I mentally admonished myself for my lack of self-control. Finding a clean pair of panties in the drawer, I pulled them up my legs, tucking my unruly cock back between my legs. The silk slip slid easily over my head and down my body. I adjusted the spaghetti straps on my shoulders making sure they were not twisted.

The bra cups of the basque needed more filling than my small fleshy breasts could provide and I debated whether to insert my breast forms or not. I decided against using them, as Christopher would be sure to notice the swellings in the front of the caftan. Shoes were another problem. I couldn't wear high heels, as they would be clearly seen (and heard) under the hem of the caftan, so I chose a pair of open toed sandals with a one-inch heel. I was a little worried when I looked down and saw my nylon-covered red toenails protruding through the opening in the sandal. I told myself I must keep my feet hidden under the caftan as much as possible. I could have worn men's shoes of course, or slippers, but the risk of discovery added to the excitement and overcame discretion.

The knowledge that I wore sexy, feminine lingerie under the caftan, unbeknownst to Christopher, was a tremendous turn-on. Thinking of it now was making me hard again. It was very uncomfortable with my cock tucked back between my legs, so I raised the front of the caftan and adjusted it so that the elastic waistband of my panties held the erect length against my belly, with the head pushed up under the lower edge of the basque. Much better.

Looking round I checked everything was in order. The wine was chilling in the fridge. Copies of the play were ready to hand, (after all that was what this was all about.) I'd draped red silk scarves over the table lamps, which suffused the room into a warm pink glow. I selected several easy listening CD's and loaded the stereo. Finally, I squirted Anais-Anais cologne behind my ears and at my throat, then sprayed a couple of puffs into the air to add to the scent of the flowers. All was ready. I sat, and waited impatiently, for the knock that would signal my darling's arrival.

Chapter Three

"Is that you, Christopher?" Olivia DeCoursey called hearing the front door bang.

"Yes Mom" he replied. "Where are you?"

"I'm in my bedroom. Come on up."

Throwing his school bag on the floor of the hall he climbed the stairs and entered his mother's bedroom. He loved this room and envied his mother for having it. Whenever he could he would sneak into it and just sit in a chair or on the bed and soak up the atmosphere of femininity and the smells of a woman's bedroom. Often when he was alone he would open drawers one after another and stare in at the contents, breathing in their lovely aromas. He loved to feel her soft clothes and would rub them against his cheek. It made him feel funny inside when he handed the soft and lacy articles. Lately he liked it even more when he discovered that his cock became erect when caressing her silken underwear.

The room was decorated in soft pastels, with a floral wallpaper by Laura Ashley; the floor was covered in a thick-pile white carpet. In the centre was a queen size canopy bed with rich red velvet drapes and pink satin sheets. Along the wall, opposite a large French window that opened onto a balcony, was a huge vanity unit complete with angled mirrors and discrete lighting. An upholstered two-seater stool stood before the vanity and two matching armchairs flanked a large oval table. Several oil paintings and watercolours adorned the walls. A pile of freshly laundered clothes was on the bed. Olivia was standing in the doorway of her walk-in closet putting a dress on a clothes hanger. He noticed it was her special little black velvet cocktail dress that she'd worn last night when they'd visited a friend of hers for dinner. It was one of his favourites and he loved to see her wearing it.

"Hello, sweetheart. Have a good day?" she inquired.

"Yes thanks Mom. Can I help you with that?" He asked starting to fold her clothes without waiting for an answer.

"Well, tell me what you did. How did it go, first day and all."

"Oh, just the usual. Maths, English, History, the usual stuff." She watched him run a lilac, silk half-slip through his hands then rub it against his cheek and smiled to herself.

"You must have done something interesting. What are your teachers like?"

"There're OK, I guess. Mr. DiMarco's nice. He teaches drama and wants me to act in the end of term play. We're going to do Romeo and Juliet."

Looking at Christopher she asked, "What part does he want you to be?"

She noticed the slight blush that spread across his face as he shyly replied "Juliet."

"Oh how wonderful," she said. "You'll be perfect for the part and you'll make a lovely girl."

"That's what Mr. DiMarco said. I told him I wasn't very good at learning lines and he's offered to give me extra tuition after school at his house, if that's alright."

"Yes of course it is. Tell me about him, what he's like?"

"His name is Salvador. He's not very tall, not much taller than I am, and he's quite slim. He has gorgeous long, thick, black hair that he ties in a ponytail. It looks real cool. I wish I had hair like his. His eyes are dark brown, almost black and he has really smooth skin with a great tan. His hands and fingers are long and thin too. I noticed them because he uses them an awful lot gesturing." He paused, considering, "Yeah. He's Ok. I like him."

"He sounds Mediterranean with a name like Salvador DiMarco."

"Yes, he is. He's from somewhere in Italy, but he's lived here for ages."

After a while, he said. "Mum, I'm a bit worried about playing Juliet."

"Why? Afraid of what the other boys will say?"

"No. It's not that. It's, well, I've never pretended to be a girl before. I've never dressed up as one. I don't know how to do it."

"Don't worry about it, dear. I'll help you. You can borrow some of my clothes to practice with if you like."

"Oh Mom, you're so wonderful. I love you so much." He cried throwing his arms round her neck and kissing her face. Olivia's arms encircled him and hugged him tightly to her breasts kissing him on his cheek. Suddenly their lips met and for several moments the kiss was much more that a mother and son kiss. Their passions became suddenly enflamed, and when she felt his hard cock pressing against her stomach she impulsively thrust her tongue deeply into his mouth.

They separated gasping for breath. "Oh darling, we mustn't do this." She said, "It's wrong."

"Why?" He wanted to know. "What's wrong? I love you Mom and I like kissing you. What can be so wrong with that?"

 

Chapter Four

It had been six years since Olivia had divorced her husband. Christopher had been eight.

They had been visiting her mother for a few days when the weather had suddenly turned nasty and blizzards were forecast, so they had returned home early. The house was quiet when they entered which surprised her a little as Roger and his partner were working at home on a big business deal they were trying to swing. She dropped their bags in the hall, told Christopher to make some tea, and had gone up the stairs to change her clothes. The sight that met her when she entered her bedroom took her breath away and left her speechless.

A naked Roger DeCoursey was kneeling on the edge of the bed with his butt in the air. Standing behind him and stroking a huge cock into his arse was the teenage son of her neighbour. At the same time Roger's left hand gripped his business partner's rigid penis, which he was sucking furiously, while his right hand masturbated his own massive pole.

Christopher had followed his mother up the stairs heading for his room when he heard her scream. He quickly ran into the bedroom in time to see the simultaneous orgasms of the three naked men. Such was the intensity of their passion, that they were oblivious to all else but their imminent climaxes. Roger's wanking hand brought his ejaculation erupting onto the bedspread beneath him. Tom Durham, his partner, poured his cum into Roger's mouth filling it to overflowing. He swallowed frantically, but some still escaped and ran in white streams down his chin and neck. Mark, the neighbour's son, growled as he rammed uncontrollably into Roger's distended anus, pumping his load deep into his rectum. At the moment of release Mark's legs went rigid, then gave way and he collapsed to the floor pulling free of Roger's hole. His sperm continued to fountain from his twitching penis, spraying around the room, some of it splattering Christopher's astonished face.

The shock had been too much for Olivia and she had fainted onto the floor. Christopher continued to stare at the homosexual spectacle, not fully understanding what was happening. He could see all the men were naked and were obviously enjoying whatever they were doing. His father and his friend from next door seemed very excited and were still unaware of his presence. The other man lying on the bed opened his eyes and looked directly at him. He smiled as he took his cock from his dad's mouth and waved it at him. "Would you like some, sonny?" he had asked.

The words broke the spell that had rooted Christopher to the spot. It also caused the other two to look up and see the eight year-old boy starting open mouthed at them.

"Christopher!" his dad said, rivulets of cum running down his chin. "What are you doing here?"

Turning, he fled and locked himself in his own room. Catching sight of his reflection in his mirror he saw globs of white semen slowly sliding down his face. Without considering what he was doing he wiped a drop onto the end of his finger and licked it. The taste was strangely comforting and not at all unpleasant. He wiped the remaining sperm from his face and sucked it off his finger, then threw himself onto the bed and cried.

He never saw his father again. He later learned that Olivia had thrown him out of the house and sued for an immediate divorce. She had won a huge, uncontested settlement, which meant that she and Christopher would be comfortable for the rest of their lives.

The shock of finding her husband, whom she had loved, sucking another mans cock while being fucked in the arse by another had almost unhinged her mind. She had been left with deep psychological damage, and never again felt any love or affection towards men. The very thought of being touched by a man made her skin crawl and she wanted to vomit.

Christopher was the one exception in her hatred of men. But she began encouraging him to express his feminine side, and become more womanly. She started treating him like a girl. She stopped buying boy's underwear for him, and bought girls cotton panties and camisole tops instead. He accepted them without comment. Because of his schooling it wasn't possible to dress him in girls' outer clothing, but she did buy white cotton blouses instead of shirts, and women's grey slacks for trousers. They were not too girly looking when worn with his school tie and blazer.

It had also been six years since Olivia had been with a man and the embrace with Christopher, and her reaction to it, had shocked and confused her. Since her divorce she had contented herself with an assortment of vibrators and dildos for sexual satisfaction. As time passed, her dreams and fantasies featured women, and she'd considered having a lesbian affair. But she wasn't sure how to go about it. She had bought contact magazines and marked possible candidates, but had always demurred at the last moment. There was a woman she knew whom she fancied a lot, but was afraid to approach, as she'd be mortified if her feelings were not reciprocated. If she secretly desired a relationship with another woman, why then did kissing Christopher and the feel of his hard cock, turn her on so much?

Chapter Five

"We'll talk about it later," she said quickly regaining her composure, but the feel of his tongue and lips lingered on her mouth. "Go and shower and change your clothes," she said, all business again. "And hang your uniform up properly. I've left clothes out for you. And hurry up, or we'll be late."

"Ok Mom." He turned to leave thinking she was angry with him.

"Chrissie" she said "Don't look so glum. I'm not cross with you. You took me by surprise is all. I need some time to think. There are implications you don't understand."

He hung his school clothes in his wardrobe as directed, striped off his underwear and stepped into his shower. He enjoyed the tingle of the hot water on his skin and the feel of the scented shower gel as he smoothed it onto his hairless soft body. His mother discouraged the use soap preferring shower gels, skin cleansers and conditioning lotions. He washed his hair with shampoo and then conditioner. He dabbed his body dry and powdered himself with talc, then used his hair-drier, brushing out his hair into bouncy waves as it dried. He pulled on the panties she had left out for him. He noticed that they were new; instead of the usual plain white these had small pink roses printed on them. The camisole matched the panties and had a little lace ruffle on the shoulder straps. His top was a blue and white striped cotton tee shirt with three quarter length sleeves, and a scalloped neck, which left the shoulder straps of his camisole visible. He struggled to pull the tight jeans up his legs and over his bottom. He noticed that they were cut in such a way as to cause his behind to round out and protrude prominently. Lastly he slid his feet into his white and pink girls trainers.

"Chrissie, darling you look lovely" his mother said when he descended the stairs.

"My shoulder straps are showing," he complained.

"Don't worry, sweetheart, no one will mind. Now come along we're late."

They hurried out to the car with Christopher carrying the sample case. It was only a short drive to the house they were visiting so they were only a few minutes late when they arrived.

With the settlement from the divorce there was no real need for Olivia to work, but she enjoyed it, especially meeting the women to whom she demonstrated. It also earned her a useful bit of pocket money from the commissions she made on the sales. She sold an expensive line of cosmetics and used Christopher as a model to display the products on. When she'd first started using him he'd asked her why he had to do it, and she'd explained that, because his skin was so beautiful and flawless, his was the perfect face for the product. She also plucked his eyebrows periodically and had had his ears pierced. After a while he came to enjoy it, and he very much liked the attention he received. He soon became an expert at applying makeup and the various techniques involved.

Seated on a stool in the centre of the room, Olivia clipped a nylon cape round his neck and fixed his hair back from his forehead with an 'Alice' band. Covered in this way; seeing only his soft girlish features it was impossible to tell he was a boy. As Olivia worked, applying various foundations, eye shadows, mascaras and lipsticks to Christopher's face, the conversation inevitably became indiscreet and personal. He often found himself blushing at some of the things they said, particularly about sex. They openly discussed the length, width and rigidity of penises, be they their husbands or not. Virility and stamina were always discussed and compared. They were equally candid when it came to masturbation and their fantasies. He was shocked when he first heard his mother admit to regularly using a vibrator.

Dabbing a little powder on his brow, nose and cheeks Oliver finished making up his face. She had brushed his eye lashes with a thick dark mascara, smoothed a grey/blue eye shadow onto his lids, added a little blusher to his cheeks to accentuate his fine bone structure and finally painted his lips with a carmine-red lipstick. She produced a pair of dangly green onyx earrings and pushed the hooks through the holes in his lobes. Removing the band from his hair she brushed it out so that it fell across his forehead and down the sides of his face in soft feminine waves. Satisfied with his look she removed the cape and hung a necklace that matched his earrings round his neck. The effect was stunning. Sitting demurely on the stool with his hands clasped in his lap was what appeared to be a beautiful young girl.

The assembled women broke into spontaneous applause; the demonstration was a huge success. While Olivia was taking orders for the full range of cosmetics she carried, Christopher rose from his seat and wandered round the room to stretch his legs. He needed to use the bathroom so he asked the hostess where it was.

"Top of the stairs and first right, sweetie"

He was eager to see how he looked but didn't hurry. Entering the bathroom he locked the door behind him and turned to stare at the lovely image in the full-length mirror. Christopher was captivated with what he saw. The thing he enjoyed most and the reason he loved modelling for his mother, was to see the results of her work. He sometimes found it hard to believe that the beautiful creature looking back at him was indeed himself. Tonight she had excelled herself with her artistry. He had never looked so ravishing. He was surprised to discover that his little cock had erected and his hand was unconsciously rubbing the front of his jeans. As he continued to stare at his reflection, turning this way and that, he opened the steel button and slid down the zipper. He pushed his hand down the front of his panties and gripped his throbbing penis. He slowly masturbated as he gazed adoringly at the lovely girl facing him. Feeling his climax approaching, he lent toward the mirror and kissed the lips of the beauty staring back at him. As their lips touched on the cold glass, he ejaculated, shooting his spunk against the lovely creature's image. His orgasm was so powerful that he staggered backward, almost falling into the bathtub.

After a while he calmed down enough to clean himself with tissues and to wipe his jism from the mirror. He deliberately left the imprint of his lips on the glass.

Returning to the main room his mother said, "Ah, there you are Chrissie, sit over here so that I can take your make up off."

"Arh, Mom. Can't I leave it on till we get home?"

There were calls of "Yes, let him." "Why not?" "He looks so pretty, it'd be a shame to remove it." from the other women.

"OK then" she agreed. "Get the stuff, we have to leave."

Driving home in the car Olivia turned to her son and said, "Thanks for modelling tonight, Chrissie. The evening's been a great success thanks to you. As a reward I'm going to buy you a present. What would you like?"

"Can I keep the necklace and earrings I'm wearing?" He said without hesitation.

"Of course you can, love." After a while she said, "You know, you really are very pretty. It's a great shame you're not a girl, because then I could buy you lots of jewellery and dainty things. I would love to have a daughter."

"I can pretend to be your daughter, Mommy."

She said nothing, but glanced sideways at him to see if he was serious or teasing. He was staring straight ahead and didn't appear to be joking. She was overwhelmed by his beautiful profile. "I wish." She thought.

Back in his bedroom, he shed his outer clothing and sat at his vanity unit. "I do like your pretty undies." Olivia observed, as she began the job of removing his make up, and then cleansing his skin with Ponds cold cream. She reminded him not to forget to apply moisturising cream to his hands and arms before she left. Sitting in his panties and camisole he completed his beauty treatment.

That finished, he walked from his room and entered his mother's without knocking. She was just slipping her nightie over her head and he had a momentary view of her naked body before it was obscured. He could still see her prominent nipples and dark bush through the gauzy material. As her head emerged from the top of the nightdress she was slightly surprised to see him there.

"Hello darling." She said. "What do you want?"

"Mummy, can I kiss you again, like we did before."

She thought for several moments wondering where the harm was in kissing her son. Ok, it was a little more intimate than was appropriate, but if it didn't go any further it surely couldn't be wrong. "Alright then, but only the one. I told you before that we shouldn't really do it."

Opening her arms she encircled him. He raised his lips to hers and they came together in a soft lingering kiss. Slowly they sank backward together onto the bed their kiss becoming more ardent. It felt wonderful to feel lips against hers again after all the years of abstinence and to feel the weight of a body lying on top of her. Abandoning her previous good intentions, she pushed her tongue into his mouth and them accepted his into hers, sucking it deep into her mouth. Their bodies began to move against each other and she could feel his erection pressing into her pussy. Even with the cotton of his panties and silk of her nightie between them she could still feel the heat of his cock at it pressed against her moistening crack. Their kisses became more passionate. She could feel the friction of his thrusting cock hammering against her sensitive clit. Her love juices flowed copiously from her cunt. Suddenly he stiffened and she knew he had come. Her own orgasm followed immediately. Slowly they relaxed and their hungry mouths parted. He became aware of wetness in the front of his panties and his mother smiling at him.

"Now, off you go to bed, my darling Chrissie, and change your panties."

"Thanks Mom. That was wonderful." His legs were shaking as he left. "'Night 'night."

As soon as the door closed, Olivia opened her bedside drawer and grabbed her largest vibrator. Switching it on she rammed it hard up her aching cunt and swooned as orgasm after orgasm swept over her.

Chapter Six

The sudden ringing of the doorbell made me jump. I went quickly to let Christopher in. On the way to the door I glanced down and was pleased to see that my feet couldn't be seen under the caftan. I checked my appearance in the mirror that hung in the hall and was satisfied with what I saw. I'd refrained from using any make up but had pinched my cheeks to put some colour into them and bitten my lips together so they looked nice and red. I had carefully washed and set my hair so that it hung to my shoulders framing my face in thick black swathes. I noticed that my hand was trembling slightly with anticipation as I reached to draw back the door latch. I involuntarily gasped as the door opened and I beheld him standing on the step. He was even more beautiful than I remembered.

"Come in Christopher, it's lovely to see you."

"Thank you Mr. DiMarco." He stepped over the threshold and held his hand out for me to shake. I took his slender fingers in mine and the touch of his soft skin sent an electric tingle up my arm and down into my groin.

"If we are going to be studying together you must call me Salvador, or Sal as my friends call me. What do your friends call you?"

"I don't have any friends around here but Mummy calls me Chrissie"

I ushered him into my softly lit drawing room and asked him to sit down. I walked through to the kitchen and returned with the wine and two glasses.

"A glass of wine before we get started, Chrissie?"

"I don't think I should" he said, "I'm only fourteen."

"It won't do you any harm and I won't tell if you don't." I said pouring out two measures.

He had seated himself on the edge of a chair and turned slightly sideways. He had crossed his legs at the knees as a woman would and his intertwined fingers supported his knee. He was dressed in his school uniform and I asked if he'd like to take his blazer off. He uncrossed his legs and stood keeping his knees together. He turned his back to me and waited for me to remove it. As I did so, I noticed how narrow and delicate his shoulders were. I suggested he remove his tie also. His shirt was made from polyester and cotton and was loose fitting. The full sleeves were buttoned at the cuffs, and I noticed that the front buttons were on the opposite side to a man's shirt; there were also darts in the front to accommodate a bust. Sitting again in the same manner and keeping his knees together he raised the glass to his lips and took a tiny sip.

Sitting across from him, and being careful to keep my feet out of sight, I raised my glass and said "Cheers." We chatted while we drank our wine and relaxed. I discovered that Chrissie and his divorced mother had only recently moved to this area, and that this was his first term at the school. I explained that I'd only been at the school a short while, and that I too was fairly new around here. Like his mother I was also divorced and that, no, I didn't have a girl friend.

Pouring a second glass of wine I suggested we start reading the play. It went quite well. I'd marked all the lines spoken by Juliet and I read the others. After a couple of hours of reading, we had finished the first bottle of wine and started the second. Chrissie asked if he could use the bathroom. I could have directed him to the downstairs toilet but I wanted him to use my personal en-suite bathroom.

"It's upstairs," I said. "Come on I'll show you, I need to go myself."

I stood and led the way from the room. Christopher was a little tipsy by now and as he followed me up the stairs he stumbled, tripping on a riser. Instinctively he reached forward to save himself, and his hands grabbed my hips. I quickly turned and helped him to his feet.

"You ok?" I asked. Chrissie nodded his head and giggled. "Here take my hand I don't want you falling down the stairs. Your mother wouldn't be very pleased."

I took his soft warm hand and again felt the shocking reaction in my groin. My cock, which had been semi hard the whole time we'd been together, now came back to full erection. We walked slowly up the stairs, hand in hand, into my bedroom and then to the bathroom. I had deliberately left panties and a bra hanging on the shower rail and the laundry basket open. There were several items of make up, moisturising cream and a jar of hair remover prominent on the shelf below the mirror. In the bedroom I'd carefully left my wardrobe door ajar, where hung several dresses and skirts along with my suits. At the foot of the bed I'd left a pair of high heels.

After five minutes when he hadn't emerged, I knocked gently on the door and asked if everything was all right. When he emerged, I said he should wait so that I could help him down the stairs again. Entering the bathroom I immediately saw that the laundry basket had been disturbed and the panties were not as I'd left them. I raised the front of my caftan, lowered my panties and emptied my bladder. After I'd finished peeing I carefully arranged my cock in the most comfortable position I could, and resisted the desire to stroke myself. Before leaving the bathroom, I quietly removed the key from the lock and put my eye to the keyhole. Christopher was sitting on the bed leafing through a mail order lingerie catalogue that I'd left on my bedside cabinet. I smiled to myself and quickly opened the door. Chrissie guiltily dropped the catalogue and stood up. I noticed he'd been studying the page that advertised bustiers, basques and corsets.

As we descended the stairs, I put my right arm across his shoulders and my hand gently stroked his upper arm. Chrissie's left arm encircled my waist and rested on my hip. I was sure he could feel my suspenders under the caftan. When we reached the bottom I said it was time he went home. I didn't want his mother forbidding him to come again because I'd kept him late.

I held the blazer for him to slip his arms in, and then he turned and faced me.

"Thank you for coming Chrissie," I said. "I think we did well this evening. I'll see you in class tomorrow."

"Thank you Sal." He replied. "I enjoyed it. You are a very nice man."

He stepped forward and gently pressed his lips to mine, then turned and left. I was so surprised by the gesture that I didn't respond. The electricity from his kiss made my lips tingle and almost made me faint. I had to reach forward to the door to prevent myself from falling. After several minutes I felt the wetness in my panties and realized I had spontaneously ejaculated.

 

Chapter Seven

Olivia was sitting in her white, lace negligee painting her toenails a scarlet red when Christopher walked in.

"Hi Mom." he called cheerfully.

"You sound in a good mood. Did you have a nice evening? Come and sit by me and tell me all about it."

He removed his jacket and plonked himself down beside her on the sofa stretching his legs out and raising his arms above his head. "Yeah, Mom, it was great. He's such a nice man. I really like him. He told me to call him Sal whenever we were alone together, but not in school of course. We got on really well reading the play. He thinks I'll be brilliant as Juliet."

"And so do I, dear. What's he like at home? What's his house like?" she wanted to know.

"Oh he is so gentle and kind. He gave me a glass of wine when I arrived and was very considerate and attentive to me. He didn't get cross when I made mistakes or lose his patience. He has a beautiful house with lots of lovely furniture and things. He was wearing this really weird thing made from silk. He said it was a caftan when I asked him what it was. It's really cool. I wouldn't mind owning one myself."

"Is he married?"

"He's divorced and he said he didn't have a girlfriend. But the funny thing was, there were lots of women's clothes lying about in his bedroom and high-heeled shoes and things. And in his bathroom there were panties and a bra on the shower rail and the hamper was full of undies. I don't understand it."

"Perhaps they're his." She casually remarked.

"You mean…?"

"It's quite possible," she said. "A lot of men like wearing women's clothes, especially their underwear. They are called transvestites or crossdressers. Are you going to his house again?"

"We have another drama class tomorrow and I told him I had to help you tomorrow evening so he asked me to come over the next night. If that's alright?"

"I know." She said. "Why don't we ask him here for supper and I can meet this special man of yours."

"Oh yes. I'd love you to meet him. I sure you'll like him."

"That's settled then. Now give me a nice kiss and off you go to bed."

That night Christopher DeCoursey dreamed of Salvador DiMarco and woke the next morning to find a large damp stain on the bed sheet.

 

Chapter Eight

It was school policy that all teaching staff must wear their academic gowns whenever they were within the school bounds. Some of the other teachers grumbled about wearing them but it suited me. It meant I could wear more feminine clothes without drawing undue attention to myself. Today, as I was teaching Christopher's class I was especially careful with my dress. I wore an embroidered peach-silk blouse, ladies slacks and a sports jacket. The addition of a necktie made the blouse appear sufficiently masculine to avoid comment.

I announced to the class that Christopher would be playing Juliet, and that the other roles would be assigned to whomever I thought could act the part. No one volunteered to play the leading man; either because they didn't feel confident enough, or, as was more likely, they were too shy and macho to play the role of another boy's lover. So, for the sake of the production, I agreed to act the part. I had planned all along to play Romeo to Christopher's Juliet but I had to make it appear as though I had no alternative.

"Now that you all know which parts you'll be playing, start learning your lines. We only have three months of rehearsals before our grand performance at Christmas."

Just then the bell sounded and the usual stampede for the door ensued. I was perched on the corner of my desk as I watched Christopher mince down the aisle toward me.

"Hi" he breathed in his sexy, soprano voice. "Mommy said to give you this." He handed over a letter. He fluttered his long lashes and my cock responded.

I opened the letter with some trepidation fearing that she had somehow divined my wicked intentions towards her son.

"My Dear Mr. DiMarco,

Christopher has told me so much about you. In fact he talks about you all the time and how you are helping him to become Juliet. I would very much like to meet you, so perhaps you would come to supper tomorrow evening at say, 7:30. Please dress in whatever you feel most comfortable.

Yours, Olivia DeCoursey."

"Tell your mother thank you, and I'd be delighted to come to supper."

Christopher's beautiful face lit up with pleasure when I accepted the invitation and I felt my cock twitch. He seemed to know the exact moment; for it was then that he glanced down at my crutch. He smiled knowingly as he walked out.

I pondered the last sentence of Olivia's letter. Could she possibly know of my weakness for cross-dressing? I'd left enough clues about my house for Christopher to see and if he'd told his mother she was smart enough to put two and two together. Or was she just being polite, and it was her way of telling me to dress informally. The more I thought about it the more convinced I became that she knew, or suspected. One wouldn't phrase a sentence like that if you just wanted to say dress casually.

As that was my last class for the day I decided I'd drive over and visit an old friend. When I had worked at my previous school I had befriended a woman who ran a second-hand clothes shop for a charity. She knew I taught drama and had supplied me with clothes for the various productions I had put on. This was a very useful arrangement because it meant I could obtain lots of female clothing without raising any suspicions. She always put aside the more unusual and outlandish outfits because she knew her customers wouldn't buy them and they might be useful to me. That was how I'd acquired the caftan.

"Hello, Mrs Pettigrew, how are you." I said as I entered her cluttered shop. "Haven't seen you for a while."

"Mr DiMarco. How nice to see you. How have you been?"

"Great, Mrs Pettigrew. I'm at a new school now a little bit away from here. Still teaching drama though. That's why I'm here."

"I see, I suppose you want some costumes for a play you're putting on."

"Correct." I said. "I'm staging a modern-day dress version of Chekhov's 'The Three Sisters' and I need something for my leading ladies." I lied. "I was thinking of something like the smart power-dressed business executive would wear to a board meeting."

"Mr. DiMarco you're in luck. Just this morning a woman brought in a lot of stuff that I'm sure is exactly what you're looking for. In fact it's still in the back. Come on through and I'll show you."

She led me through a curtained doorway into her store and sorting room. The place was piled high with bulging black plastic bags and racks of hanging garments. Just then the bell over her entrance sounded as another customer entered.

"They're on that end rack." She said pointing. "Have a look round and see what you can find then give me a shout." With that she ducked back through the curtain leaving me alone in a crossdressers Aladdin's cave.

I quickly found the things she had referred to. There were four woman's business suits in charcoal grey, beige, maroon and powder blue. They were all similarly styled with slight variations in the cut, the lapels and the details. The jackets had tailored waists and fastened with either two or three buttons. Each suit was matched with both a skirt and a pair of pants. Looking quickly round to check Mrs Pettigrew was still busy I slipped off my sports coat and put on the maroon jacket. I was thrilled to find it fitted to perfection. The woman who had donated them must have been quite large, because even though I had a small frame and was slightly built, I was still bigger than most women. The jackets and skirts were fully lined but the slacks had waists designed for a woman's shape. I realized I would have to do something to reduce my waist measurement if they were to fit properly.

Just then I spotted the very thing I needed. In the corner of the room, where she put aside the more bizarre items, was an old-fashioned waist cincher. The type used to create the desirable hourglass figure that Victorian women strove to achieve. I picked it up and examined it. The pre-formed whalebone stays were covered in black silk. There was a row of hooks-and-eyes down the front and criss-cross lacing at the back. One placed the garment around ones waist and fastened the hooks-and-eyes, before presumably, ones maid pulled the lacing together at the back. I could see it would be possible to attain an extremely narrow waist with it.

Mrs Pettigrew returned and surprised me as I was looking through similar foundation garments. "Well" she asked, "find anything useful?"

"They are perfect. Exactly what I was looking for." I said, referring to the suits. "Unfortunately a couple of the sisters are little too big for them so I was looking for something like this." He said, holding up a long-line bustier corset, with lightly padded underwired cups, hook-and-eye front fastening and body controlling sides.

"Take whatever you find that's useful," she said, "I shall never sell them anyway. Now, you will probably want blouses and slips to complete the outfits" She quickly found four of each. "Anything else?"

"Yes, there is one scene where the girls are in their bedroom at night and I think they should be wearing nighties and negligees." I lied again. It was starting to become easy.

"Mr. DiMarco!" she exclaimed, clapping her hands together, "it's definitely your lucky day. The woman who has just in here, brought in a box full of lingerie. There are definitely nightdresses and negligees, as well as bras, panties the lots of other stuff. Of course you won't want the knickers and things but if you give me a few minutes I'll sort through it for what you want."

"No need Mrs Pettigrew" I quickly said, seizing the opportunity, "I haven't the time to wait. I'll take the lot and sort it myself when I get home. I'll throw out whatever I don't want. And I'll take the four suits, blouses and slips. Oh, and these too." he said, holding up the corset, waist cincher and a pink panty girdle.

"What about shoes?" she asked, always keen to make an extra sale. "I've a nice selection in the front."

Carrying the suits and the other things I followed her into the shop and dumped the clothes onto the box of underwear on the counter.

"What size?" she asked from her knees, sorting through a pile of footwear.

"Seven." I said, hoping she didn't realize that it was my shoe size.

She found four pairs in size seven. Two pair were court shoes with three-inch heels, one in black patent leather, the other a light grey. A pair of strappy sandals with tiny silver buckles on the ankle strap and a four-inch heel, and a pair of dark brown oxfords with a two-inch heel. "That's all I can find in your size." She said rising to her feet.

I gave her my credit card and while she processed the transaction I carried the stuff out to my car and piled it into the boot. I was delighted to see that she had only charged me for the suits, blouses and shoes; and these at a fraction of the cost of new. I drove off feeling extremely pleased with myself.

On my way home I stopped at the Pharmacy we used when we were married and where my ex-wife had bought her contraceptive pills. For some reason I still carried an old repeat prescription of hers in my wallet and I was able to purchase a three-month supply. The bored clerk only glanced at the drug to be prescribed and the doctor's signature. If he'd checked he'd have seen it was way out of date, but I was gambling on him not noticing.

I unloaded the stuff from the car and spent the next couple of hours happily trying on the clothes I'd bought. As I'd thought, the jackets fitted perfectly but the pants were loose on his hips and too snug round the waist. The skirts were a better fit, but I couldn't show up for the first time at Christopher's wearing one. I tried the waist cincher. It wasn't very broad, only nine inches, but I still had great difficulty lacing the back together. Then I had an idea. With a tape I measured the waist of the pants: twenty-four inches. I then fastened the front of the waist cincher and adjusted the lacing at the back until it was a little less than twenty-four inches. When I wrapped it around my middle again I was just able to pull the two edges together and fasten the hooks-and-eyes. When I tried the pants on again the waistband was just loose enough to easily pull up the zip at the back and fasten the button.

 

Chapter Nine

I rose late the next morning. I ate a leisurely breakfast, or more accurately brunch, then did a little shopping in the afternoon buying a bottle of wine and a box of chocolate to bring as a gift. I was in a constant state of excitement, much like a child who can't wait for Christmas. I kept checking my watch only to find it was only two minutes since the last check. I couldn't believe how the time was dragging. At about four o'clock I started my bath. I poured in extra oil and bubble and luxuriated in the heavenly scented water. My skin was still smooth and hairless so there was no need to do any removal. I shampooed my hair twice and conditioned it. Feeling beautifully clean on the outside I decided to clean myself on the inside too. I got my enema kit from the cupboard and mixed a solution of herbs and salts with warm water and filled the bag. I hung it from the shower rail then lay on my back with a cushion under my hips and my legs in the air. I sucked the nozzle to lubricate it then inserted into my anus. I pushed it in about three inches then turn on the tap. The warm fluid emptied from the bag and filled my rectum. I lay on the floor for about five minutes till the pressure became too much to bear, when I was forced to void my bowel in the toilet bowl. I repeated the procedure this time adding a violet perfume to the liquid.

I next turned my attention to my hair. I wound large rollers in the front and at the sides to give it some body and undercurl. I blow-dried it, at the same time using a curling brush to form it nicely around my face. When it was dry I removed the rollers and brushed it out again. I was pleased with the effect. My hair was thick and shiny; it covered my brow in a heavy fringe, and framed my face at the sides in a passable pageboy style. I wished I could get it properly cut and styled by a professional hairdresser.

Satisfied with my hair I sat on my vanity stool, lifted first one, then the other foot up and painted my toenails a brilliant red. My fingernails I shaped with an emery board and applied a clear varnish to them. I was afraid to paint them the same colour as my toes.

At seven o'clock I began dressing. This was always the most exciting and enjoyable part. Firstly I laid out on the bed all the things I was going to wear. I'd decided on the maroon suit. I would have preferred the powder blue, but for the same reason I could not wear a skirt, I could not wear blue either. It was a little too obviously female. I chose a lavender silk blouse with a Peter Pan collar, baggy sleeves and four-inch tight fitting cuffs. The buttons at the wrists were padded but a flap of material hid the ones down the front. I selected a white camisole with delicate embroidery across the front and tiny pink roses where the straps joined the body, and a lacy white bra with matching high cut panties. I pondered whether to wear tights or stockings. I planed on wearing the brown oxfords, so whatever I chose would have to be dark. I could not risk tan or shear tones being seen. As it transpired, I had no dark coloured tights, only dark brown stockings, so it would have to be a garter belt. In the box of things I'd bought from Mrs Pettigrew I found one that was just perfect. It was satin in lilac and blue, with a lace front panel and dainty bows where the suspender tabs joined belt.

When everything was ready I began to dress. First was the waist nipper. I got it on much easier this time and it felt reasonably comfortable. Then came the garter belt. I clipped it together at the front then slid it round so the clasp was at the back. Sitting on the stool I rolled the stockings up my smooth legs and hooked them to the suspenders. I stood and adjusted the seams, and then the tension on the garter tabs so that they were nice and taught. My cock was beginning to thicken as I stood and admired my nylon-clad legs. Fixing the bra in the same way as the garter belt I swivelled it round my chest and pushed my arms into the shoulder straps. I made sure they weren't twisted and were at the right adjustment. When I settled my breast-like pecs into the bra cups I was surprised to find that there seemed to be much more fleshy tissue. I was almost a size bigger. A side effect of cincher was that it pushed up my breast flesh and I gained a convincing cleavage. I slipped the camisole over my head and smoothed it over my bra. Holding my panties up to ensure I had them the right way round, I stepped into them and pulled them up my legs. My penis was semi-hard but I was determined not to masturbate. I pushed my testicles up into the space in my pelvic bone and tucked my cock back between my legs. Pulling the panties up snugly, I was pleased to see a feminine mound and not a bulging crutch. The blouse was next and my shaking fingers had trouble with all the little buttons. Lastly I pulled on the pants, tucked in my blouse, pulled up the zip and fastened the button at the back. I would have to pee sitting down, I thought, as there was no fly. They were flat across the front.

Standing before my mirror I slipped on the jacket and inspected myself. I looked and felt sensational, but unfortunately, much too feminine. I thought for a moment, and then knotted a man's plain red necktie under the collar of my blouse. It did the trick. I looked sufficiently androgynous to be either man or woman. I fastened the two buttons on the jacket, which helped to conceal his bust, but accentuated my shapely waist. It was a pity I had to hide my bosom because I was quite proud of my new curves. I slipped my feet into my shoes and walked round a bit getting the feel of them. I was well used to walking in heels but new shoes always take a bit of getting used to.

There was still something missing. Oh yes, I know. I returned to my bedroom and dabbed a little Poeme perfume on my wrists, behind my ears and at my throat. Now I was perfect.

At last I was ready; one final check in the mirror. All OK. I collected my car keys, the wine and the chocolates, and then with mounting excitement I left to visit my darling Chrissie and his mum.

 

Chapter Ten

"Come on Chrissie, time to get up. We've a lot to do today."

He struggled out of bed and padded barefoot to the bathroom, relieved himself and showered. Tying one of his mother's old pink cotton bathrobes loosely round his waist he went down to a breakfast of cereal and toast.

"What's the hurry?" he wanted to know.

"You know I have an important demonstration this afternoon. And we have to shop and get ready for this evening. I want everything to be perfect for Mr DiMarco."

His heart skipped a beat when he remembered that Sal was coming to supper. He quickly finished his breakfast then ran up the stairs to prepare for the demo. He dressed in his tight jeans, a tee shirt and trainers. Olivia made his sit at her dressing table while she brushed and combed his hair, sprayed mousse on it and styled it in soft curls. Looking closely at his face she decided his eyebrows needed a little attention. Taking her tweezers she plucked and shaped his brows into a perfect arc.

Satisfied that his flawless face was the perfect canvas for her paints and powders, she told him to collect the sample bag and get in the car. "Oh, and bring your earrings and necklace" she called as an afterthought.

They called at a supermarket on their way and bought what food they would need for the meal, just salads, cold chicken and fresh crunchy bread. She didn't intend to spend hours cooking.

The demonstration was huge success. She surpassed herself with her make-up skills making Christopher look more beautiful that she had ever seen him. He received lots of praise from the customers, and more than one compliment was tinged with envy.

It took longer that normal to take the orders, so they were running late as they hurried back to the house to prepare. She had forgotten to clean the make-up from Christopher's face and he was happy to leave it on.

The next hour was a whirlwind of activity as they prepared the meal, laid the table with her best silver cutlery and Royal Worcester china. Spotless white damask napkins in antique silver rings were put out together with crystal wineglasses. They tidied the drawing room, placed scented candles here and there, and lit them. With half an hour before he was due to arrive the house was ready.

She told Christopher to go and change his clothes into what she had left out. This was a pink silk blouse, with a long pointy collar and bouffant sleeves. On impulse he removed his camisole and panties and wore it next to his bare skin. The sensation was thrilling. He left it unbuttoned almost to his navel so that his necklace could be clearly seen on his hairless chest. Also clearly visible through the gauzy material were his dark nipples. The pants were of turquoise satin, skin tight and flared at the ankles. The figure hugging material clearly accentuated his perfect globes and his shapely thighs. Without his panties his genitals were blatantly emphasised. Around his waist he tied a three-inch wide sash, whose ends hung down the outside of his right leg. On his feet were embroidered Arabic sandals.

Olivia had chosen a twenties style flappers dress with a drop waist. The white filmy material was translucent and it was obvious she had shunned her bra. Her firm breasts were clearly visible topped with her prominent dark nipples. They swayed and bounced gently when she moved. Also visible were the thin strings of her thong panties and the tiny triangle at the front covering her pussy. Around her neck she'd hung three strings of pearls that framed and accentuated her breasts. She was barelegged and wore a pair of heels, so high Christopher didn't know how she walked in them.

When they met in the sitting room they were both stunned by the others appearance. They stared at each other in silent admiration for several seconds before Christopher blurted. "My God, Mum. You look sensational."

"You like?" she asked, doing a twirl that set her breasts dancing under the dress. "You don't look so bad yourself. But those pants are awfully tight, and very revealing" she said, eyeing his bulging crutch. "You'll have to change them, I didn't realize they were so small. And Chrissie, you still have your make-up on. What will Mr DiMarco think if he sees you looking like that? You must remove it at once."

"Arh Mum, I'm sure he won't mind." Just then the doorbell rang. "Too late now anyway." He said and went to answer it.

 

Chapter Eleven

My heart was beating much faster than normal as I pressed the bell. I heard it buzz inside and almost immediately the door opened. I at first didn't recognize the lovely vision that stood before me. My mouth fell open in surprise and wonder, then it hit me, this incredibly beautiful creature was Christopher DeCoursey. With the wine in one hand and the chocolates in the other I could only stare.

In his sweet treble voice Chrissie breathed "Hello, Sal. Great to see you." He lent forward and kissed me on the lips. "Come in and meet Mummy."

He relieved me of my gifts, and I followed the apparition in a daze, my eyes fixed on the rolling buttocks as they moved sinuously together beneath the clinging material. The taste of his lipstick on my lips was intoxicating and a heady perfume filled my nostrils. Chrissie's mother was waiting in the drawing room and stood as we entered. She walked toward me with her hand out.

"Hello, Mr DiMarco. It's very nice to meet you. I'm Olivia, Chrissie's mother."

I took her warm hand and pressed my lips to the backs of her fingers. "The pleasure is all mine Olivia, and please call me Sal."

"Please sit down, Sal." She indicated a chair; somewhat flustered by my old fashioned gesture. "Would you like a glass of wine?" I nodded. "Chrissie darling," she said, "please serve the wine."

She sat opposite and examined me closely, scrutinising my clothes. I was sure she recognized immediately that they were a woman's garments. She looked at my shoes and my stocking covered ankles. Then at my pants, which were clearly made without a fly, then at the feminine blouse and my womanly hair do.

"That's a very nice suit, Sal, I love the colour." She said. Then after a pause, "It's very warm in here, don't you think? Perhaps you'd like to remove your jacket?"

"Chrissie, dear, take Sal's jacket and hang it up for him please." She said as Christopher arrived with a tray and glasses of wine. "And please, take off your tie too, we're very informal here."

I had little choice but to do as she said. I stood, removed my tie and let my jacket slip down my arms. There was no hiding the fact now. She had quickly exposed me as the crossdresser I was. I took a deep breath, squared my shoulders and defiantly pushed out my bust, which I'd tried to conceal under the silk blouse. I sat down again crossing my legs at the knee in a lady-like manner. The leg of my pants rode up my calf revealing my stockings and high heels.

She looked at me again, nodding in approval. "Very nice." She said. "That's a lovely blouse, Sally."

I blushed, partly from the compliment, and partly because she had called me by my private femme name.

Now that we both knew where we stood we relaxed, chatted and drank our wine. I wasn't sure whether Christopher knew of my transvestism or not. He made no comment on my clothing and seemed to accept it as perfectly normal that I was dressed as I was. He sat on the floor with his legs folded under him by his mother's chair and I couldn't keep my eyes off him. I saw now that as well as full facial make-up he was wearing long dangly earrings and a matching necklace hung at his throat. His silk shirt gapped open revealing his smooth boyish torso and pink nipples, and the skin-tight pants outlined his every curve and bulge.

My cock was hardening painfully squashed as it was between my legs. I would have to find someway of easing it soon or I would be in agony. My chance came after an hour or so when Olivia announced that it was time to eat, and would I like to use the bathroom. As soon as I was inside the room I dropped my pants and panties then sighed with relief, as my tortured prick was release from its confinement. I adjusted it, as I had done on previous occasions, by pushing the head up under my suspender belt and trapping the shaft with the panty elastic. Replacing my pants, I could clearly see the outline of my erection inside the flat front, but could do nothing about it. I hoped the others wouldn't notice. I brushed my hair, pinched my cheeks and bit my lips, before returning to find them sitting at the table in the dining room.

During the meal I kept my napkin across my lap successfully hiding the telltale bulge. As we were finishing the salad and chicken the telephone rang. Olivia excused herself and went to answer it. She was gone some five minutes and when she returned she was ashen, trembling and tears were running down her cheeks.

"Mummy, what's the matter?" Christopher asked with concern.

"It's my mother, your granny," she said. "She's been taken ill and is in hospital. We shall have to go to her at once. She has no one else to look after her. We must leave right away."

"But Mummy. I can't leave. I have school and the play to rehearse."

"You have to. You can't stay here on your own. You're too young."

"Could I make a suggestion?" I said. They both looked at me. "Christopher could come and stay with me. I have lots of room and I'm sure he wouldn't be any bother. That way he wouldn't miss any schooling and I could look after him."

"Well…" she said, not quite sure of the wisdom of my suggestion.

"Oh yes, Mummy. That's a wonderful idea. Do let me stay with Sal. We could practice the play together too."

She thought for a moment considering the proposed arrangement then came to a decision. "OK. You can stay with Sal. Go and pack a bag while I have a chat with him."

My heart sang with joy. The prospect of having this darling boy living in my house was exciting in the extreme. Making sure to keep any emotion from my face and voice, I said to Chrissie's departing back. "Just bring your school uniform and whatever books you need for classes. I have everything else. I've even got spare clothes you can borrow. Besides, we can always come back for anything I don't have."

"Sally you will take care of him won't you." She said. "He's only fourteen and very susceptible. He's a very sensitive child; so do be careful how you behave with him. He is confused enough about his sexually as it is, so please be kind and considerate with him. Indulge him if he appears overly feminine, it's in his nature. I hope you understand?"

"Don't worry, Olivia. I shall look after him as if he were my own son."

"OK. I'll trust you. I must go and pack." She said leaving him sitting at the table.

While they were gone I cleared the table and put the plates and cutlery in the dishwasher. I'd finished tidying the room and was blowing out the candles when Christopher came in carrying his hold-all. A few minutes later Olivia entered. She had changed into a smart business suit very similar to the one I wore but with a skirt. She wore the collar of her blouse outside her jacket and open at the throat. I could see her lacy bra through the material. Christopher held my jacket for me and I arranged the collar of my blouse in the same way.

"Goodbye darling. Give Mummy a kiss." She took his head in her hands and brought her lips hard onto Christopher's. He threw his arms around her neck and kissed her equally hard in return. The kiss lasted longer than I thought it should have between a mother and her son. Turning to me she held her hand out. I took it. Suddenly she stepped forward, wrapped her arms around my shoulders and embraced me. I felt her soft breasts press against mine. Then she kissed me on both cheeks and said. "Goodbye Sal. Remember what I said. I'll phone later."

Chrissie and I stood together at the door and waved as she drove off. I quickly checked the house ensuring all the windows were securely closed and the gas and electricity were turned off. I locked the door and walked to the car where my delicious Christopher was waiting.

Chapter Twelve

On the way to my house I announced. "There are certain ground rules we must establish before we start living together. The first is that we respect each other's privacy at all times. That means never entering my bedroom without first knocking. I shall of course accord you the same courtesy. You must keep your room tidy at all times. You will have to share my bathroom but we will try to use it at separate times. But if we do find ourselves in there together, I won't have a problem with that. After all we are both men. OK so far?"

"Yes Sal. No problems."

"Secondly you will have to undertake certain chores around the house to help towards your keep. Do you know how to do laundry?"

"Oh yes, I often do it at home, and ironing. Mummy sometime gets me to hand-wash her delicate things."

"Excellent. From now on the laundry is your responsibility. Can you cook?"

"A little bit. Mummy has taught me a few dishes."

"Ok. We'll share the cooking duties. I'll do any shopping and buy groceries when we need anything and you can clean the house. I don't know how long your Mom will be away, but if we each do our bit we should be able to get along all right. Are you happy with that?"

"Yes Sal, I want to help whenever I can."

Just then we pulled into the driveway of my house and I switched off the engine. The night was dark and quiet. My nearest neighbours were some distance away and I rarely saw them. Chrissie followed me into the house carrying his bag. I led him straight up the stairs and showed him to his room. It had been the previous owner's teenage daughter's room and was decorated to suit her tastes in pastels with lots of pinks, mauves and silver. I'd bought the house furnished and hadn't got round to changing it, so it was pretty much as she'd left it. She'd even left a Barbie doll on the dressing table.

"I'll get some sheets and make up your bed. You can unpack your things and hang them in the closet."

It was after eleven o'clock by the time the bed was made up with satin sheets and pillowcases. "It's getting late," I said. "I think we should turn in. As it's Sunday tomorrow, we'll have a lazy day and maybe read some lines. How does that sound?"

"Good idea."

I hung my suit with the others in the closet, put my blouse in the laundry basket and removed the waist cincher. I was standing in my bra, panties and suspenders when there was a soft knock on the door. "Just a minute" I called. I quickly pulled my caftan over my head and said, "Come in."

Chrissie stuck his head round the door and said, "Sal, I forgot to bring my pyjamas, have you got something I could borrow?"

I pretended to think for a moment then said, "I don't have any peejay's but I think I have something that will do. I'll bring it to your room in a minute."

When the door closed, I went to the box of things I'd bought from Mrs Pettigrew. I remembered seeing a rather sumptuous nightie amongst the other stuff. I dug it out together with the matching panties. The knee-length nightdress was periwinkle blue with an enticing tie under the bust keeping it together at the front. Lace, bordered the plunging neckline and the hem. The front fell open to reveal the matching g-string. I held the confection of lace and frills against myself to gauge the affect. The panties were a mere wisp of nylon and would be visible through the gossamer material of the nightie. I had looked forward to wearing it myself but was prepared to sacrifice it for the greater good.

I tapped on his door and entered when invited. Chrissie was sitting on his bed, a towel wrapped round his waist, reading a copy of 'Cosmopolitan' magazine.

"This is the best I can do," I said handing him the nightie. "Have you worn one of these before?" He shook his head negatively. "I think you'll find it very comfortable. Would you like me to help you with it?"

"Err. I think so." He said. "I'm not sure how they go."

I passed him the panties. "Stand up and put these on." He modestly turned his back to me and dropped the towel. The sight of his superb cheeks as he bent forward and put his feet into panties gave me an instant erection. I held my breath as Chrissie slowly worked the wispy garment up his thighs and settled it round his waist. The thin thong nestled between his buttocks and when he turned the lacy triangle at the front barely covered his little cock and balls. I held the nightie open for him to push his arms into, and then tied the broad ribbon in a big floppy bow at the front. I couldn't resist smoothing it down his body. Chrissie hadn't yet removed his make-up or earrings, and the image of this achingly beautiful boy, had my throbbing cock dripping pre-cum into my own panties.

"Does it look Ok?" he asked, holding it out at either side with the tips of his forefinger and thumb and slowly rotating. "It feels nice."

I found I could hardly speak. My throat had gone suddenly dry. "It's lovely," I croaked. "It suits you perfectly." I couldn't resist adding, "You really are the prettiest boy I know." Chrissie blushed, and gave me a look of coy innocence from under his fluttering eyelashes.

I was besotted. "Now, you'd better remove your make up and earrings. You'll find some cleanser and moisturizer in my bathroom you can use." We walked together from the room to the bathroom, my arm around the boy's slender shoulders.

Whilst Chrissie was busy in the bathroom, I quickly stripped off my caftan and lingerie and put on my own nightgown: a full-length mint green satin sheath. It was cut low in the front, designed to expose a goodly portion of breast, and had thin, string shoulder straps. The bust was decorated with a lace overlay. I slid into my bed and waited, my erect penis forming a pyramid under the sheets. I couldn't resist wrapping the satin nightie round it and slowly stroking myself as visions of Chrissie, in his nightie floated through his mind.

After what seemed an age, but was only five minutes, the bathroom door opened and Chrissie walked in. He was rubbing moisturising cream into his hands and arms. He looked at me, as I lay propped up on my pillows, the top of my nightie and most of my breasts exposed above the sheet. His eyes glanced down to the prominent mound in the centre of the bed then back up to my chest.

"Good night, Sal" he said and started for the door.

"Don't I get a good night kiss?" I asked. Chrissie turned and came to the side of the bed, bent at the waist and touched his lips to mine then started to rise. "No, not like that," I whispered "Kiss me like you kissed your mother."

This time Chrissie took my face between his two soft hands and crushed his lips hard against mine. I felt his tongue tracing the insides of my lips and touching my teeth. I was breathing hard through my nose, and as his kiss continued I realised I was masturbating furiously. When I felt his hot wet tongue probe into my mouth and start to fuck in and out, I came with an explosion of sperm that soaked my nightie and the sheet. Gradually my pumping hand slowed and his passionate kiss ended.

Straightening up, he flipped his head to the side to move the wayward lock of hair that fallen over his face. His earrings shook, and he quietly said "Good night, Sal." He smiled his adorable smile, then turned to leave. Just then he was in silhouette, and I saw his erect penis tenting his panties and nightie. I opened my mouth to reply but no sound came out.

 

Chapter Thirteen

I had been up for over an hour when Christopher walked into the kitchen. He was still wearing his nightie, his hair was tousled and he was rubbing sleep from his eyes. My cock began to stir as I glazed lovingly at his innocent appearance. He seemed unconcerned with the way he looked as he padded on bare feet to the table and sat. "Good morning, Chrissie," I said, putting aside the newspaper I'd been reading. "Do you want some breakfast?"

"Just some orange juice and cereal will be fine."

We chatted while he ate, then when he'd finished I handed him a small round box. It contained the contraceptive pills. I'd removed them from the bubble wrap they'd been supplied in so that he wouldn't know exactly what they were. "Chrissie," I began, "I want you to take one of these tablets every morning from now on. Boys of your age are prone to acne, and these are an old herbal remedy that will stop you getting it. It would be a terrible shame to have your lovely skin spoiled by awful spots."

He took it without hesitation. "Thanks, Sal. I've was dreading getting it. Some of the guys in school have it, and a couple are really bad cases; they look awful. I'll start taking them now."

"Good boy. And one other thing. I think you should let your hair grow. Juliet will look a lot more convincing with real hair rather than a wig. Later, when it's longer, we'll go to a hair stylist and get it cut nicely."

"Ok, great. I'd love to have long hair like yours, Sal,"

"Now, I've got to go out for a while, to get some things and check your house is ok. Why don't you have a nice relaxing bath and wash you hair, then when I get back we could read some lines."

I drove directly to his house and let myself in. I checked around the downstairs rooms for any signs of a forced entry then went up the stairs to explore. I was dying to see Olivia's bedroom. The first room I entered was obviously Christopher's. I straitened his untidy bed and picked his clothes up from the floor. I pulled open a drawer to put them in and was surprised to see it filled with girl's underwear. The other drawers contained normal boy's stuff as well as blouses and tops.

The room across the landing was Olivia's and I entered with mounting excitement. I always get a thrill from secretly entering a woman's bedroom: to see her personal and private things and to trespass into her intimate world. I stood in the centre of the room and slowly looked all round soaking up the smells, the colours, the textures, and the feel of her feminine domain.

I moved over to the walk-in closet and opened the double doors. Her dresses, skirts, suits and coats were hung neatly on rails. Her many pairs of shoes were lined up on the floor. A stack of drawers contained her accessories; belts, scarves, and handbags, others held jumpers and blouses, tee shirts, and cardigans. Her wardrobe was extensive, and her taste excellent. Many of the items had designer labels and were clearly very expensive.

Leaving the doors to the closet open, I seated myself at her large dressing table. My eyes roamed over the huge assortment of jars, bottles, tubes, aerosol cans and boxes scattered over the surface. There was an incredible selection of cosmetics of every brand and for every purpose. I wondered why she needed so much, before I remembered she used them for her demos. Along with all this stuff were hair rollers, bobby pins, combs, brushes and jewellery. The shear jumble of things was in complete contrast to her otherwise apparent orderliness.

One at a time I opened the drawers of her vanity unit, and discovered her lingerie. Each drawer contained a different article: panties in one, bras in another, stockings and tights in a third. I found her camisoles, slips and petticoats in another, and her more exotic pieces, her bustiers, basques and girdles together in yet another. The sight and feel of her intimate underwear had brought my cock to rigid erection. With trembling hands I reached into a drawer and withdrew a double handful of her flimsy, lacy panties. With my face buried in the silky material, I inhaled deeply, breathing in the heady aroma.

Almost in frenzy, I tore off my clothes, throwing them to the floor, and returned to the vanity seat. Forcing myself to calm down I carefully selected her prettiest bra and panty set. Checking the labels, I was delighted to find we were nearly the same size, except in the bust. Without any enhancement I could just about fill a 36A, but Olivia was a full 36C. I unhurriedly put on her bra, and then filled the cups with some of her spare panties to make up the difference in cup size. I pulled her panties up my legs and settled my rampant manhood in the usual manner with the head protruding from the top. I chose a pair of shear tights, then changed my mind, put them back, and sorted out the sexiest garter belt she owned. I fastened it round my waist and smoothed on a pair of flesh tone nylons. As I stood to clip the suspenders my cock was leaking pre-cum into her panties.

Returning to her closet I tried several pairs of shoes till I found the ones I like, silver sandals with a 3 inch stiletto heel. For the next two hours I tried on every dress she owned as well as her skirts and tops. I posed before her full-length mirror. I minced up and down the room with the exaggerated gait of a catwalk model crossing my feet as I walked. I swished round in her skirts and dresses loving the effect I created.

All this time my cock was painfully hard, but I was determined not to give myself any relief. I knew that once I came the thrill would be gone, or at least it would not be as intense, and I wanted to continue savouring the experience of wearing her things for as long as possible.

At the end of my fashion show I returned her clothes to their hangers and replaced them in the closet in their correct places. I'd put several outfits I particularly liked to one side. I also selected her prettiest lingerie and several pairs of shoes. I carefully folded the dresses and packed everything into a suitcase I found in a cupboard under the stairs.

With a feeling of regret I finally redressed in my own clothes, keeping her lingerie on underneath my shirt and trousers. It would have been wonderful to wear one of her dresses back to my house, but I was afraid to risk it, even though on a Sunday morning there were few people about. I checked to make sure everything was in order, locked the house and left.

 

Chapter Fourteen

When I got back home I found Christopher in his jeans and tee shirt lounging in front of the TV. His hair was freshly washed and he was still blow-drying it as I walked through the lounge and headed up the stairs. In my room I unpacked the case and stowed the things away. Stripping off my outer clothing I debated with myself whether to keep the lingerie on or not; decided not, and removed them. I slipped the caftan over my naked body then went back down the stairs.

"Ready to get started?" I said picking up a copy of Romeo and Juliet. We read the parts to each other for a couple of hours before I stopped him saying, "It's no good, Chrissie. You don't seem to be getting into the role properly."

He looked disappointed "I'm sorry. What am I doing wrong?"

"You are just reading the lines. You're not being Juliet. You have to become her, to think like her, to behave like she would. You have to become more feminine or you will never be successful in the part."

"What can I do about it? I'm not a girl. I don't know how to act like one or think like one. I don't know how to be feminine. I really want to be good in the part. You must help me."

I pretended to give the matter some deep thought. "I know," I said, clicking my fingers as inspiration hit me. "We could start by dressing you as a girl. When you're wearing the right clothes I'm sure you'll feel more like Juliet."

"Oh I'm not sure, Sal. Do you think it will help? I've never worn girls' clothes before. I'm not even sure how to put them on. Anyway I'm shy and I'll be embarrassed." He said in his most modest way.

"You will soon have to start wearing them, but on this first occasion, if it'll make you feel any easier, I'll dress up as well. I'll help you with your clothes and you can help me with mine. What do you say?"

"Well, OK." He reluctantly agreed.

My heart leapt with joy as I led him to my bedroom. "Undress while I find something for you to wear." I went to my dresser and collected the things I'd previously selected for him. When I turned he was sitting on the edge of the bed still fully clothed. "Come on," I said "no need to be modest."

"Will undress as well?"

"If you really want me to, I will" I hedged, fully intending to.

"Yes. I do." He said simply.

He stood and I took the hem of his tee shirt and pulled it over his head. I knelt down and removed his trainers, and then still on my knees; I undid his jeans and slid them, together with his underwear, down his legs. He stepped out of them and I started hungrily at his smooth naked cock and balls swaying just inches from my face. Resisting the urge to grab his hips and suck his inviting penis into my mouth, I stood and undid the buttons of my caftan. Standing squarely in front of him I wriggled my arms out of the sleeves into the caftan then, with a shrug of my shoulders, let it fall round my feet. I watched his eyes as they were drawn magnetically to my semi-hard cock and aching balls. His mouth dropped open in wonder as he watched it swell and rise up into full rigid attention. He stared as it twitched and throbbed, and a bead of pre-cum appeared on the head.

Acting as if it were perfectly normal to be naked with a massive erection, I picked up Olivia's pretty baby blue lace bra and told him to turn around. I put his arms through the straps then clipped it together in the middle of his back. "This is your bra," I told him, "girls wear them to support their breasts. Unfortunately, as you don't have any yet, you'll have to wear these false ones." I showed him my breast forms." They're very realistic as you can see. They look and feel exactly like real breasts." I inserted one into each cup of his bra then adjusted the straps to the correct length.

"Now you have to help me with my bra." I handed him my own scarlet underwired 'WonderBra', and turned my back to him. I held my arms down for the bra straps then felt his fingers on my back struggling with the clasp. He eventually got it closed and I turned back to face him. I adjusted my fleshy pecs into cups and with the aid of M. Gossard's 'WonderBra' technology produced a convincing cleavage. His eyes moved from my chest to my rearing penis.

"Next we need a suspender belt to keep our stockings up." I said. "We always put these on before our panties so that we can go to the bathroom without having to undo our stockings." I'd chosen one of Olivia's delicate, lacy specimens for him and I again went behind him and clipped it together. I was excited to see he was starting to get hard. "Now mine." I said, giving him my garter belt, also in red. I turned so that he could pass it round my waist between my bobbing cock and my stomach. He managed the hooks and eyes easily this time.

"Pay attention now Chrissie, and I'll show you how to put your nylons on. Do the same as I do and you'll have no trouble."

I sat on the side of the bed and gathered the stocking into a ring. I put it over my toe; pulled it round my heel then slowly drew it up my calf and thigh. I stretched out my leg running my hands up its length to make sure there were no wrinkles.

"Watch carefully. This is how to clip the suspender to the top of the stocking."

I repeated the procedure with the other leg then told him to put on his own. He managed to pull up the stockings but had difficulty fastening them. I stood behind him and reached round to help him. I nearly came as my cock pressed into the crack of his arse cheeks. I thought he hadn't noticed my intimate touch against his rear till I felt him push back slightly and wiggle his arse against me. I deliberately fumbled with his garter tabs 'accidentally' fondling his stiffening cock at the same time.

Kneeling at his feet I held the satin and lace panties, which matched Olivia's bra, for him to step into. I saw him shiver and goose bumps appear as I slowly eased them up his legs and settled them round his waist and buttocks. I noticed with pleasure that his cock had grown fully hard and the head was peeping from the top of the elasticated waist. I gave it a gentle squeeze through the filmy panties and said, "It seems that you like wearing girls clothes after all." He blushed and tried to hide the evidence of his body's betrayal behind his hands. "Don't be embarrassed, Chrissie. It's nice that you like to wear pretty things. As you can see, they have the same effect on me. Now please help me with my panties."

It was pure bliss, letting this divine creature, dressed so sexily in his mother's lingerie; pull the sheer silk panties up my legs. He carefully avoided any contact with my rampant penis but left the shining head sticking up from the waistband. After my mornings indulgence with Olivia's clothes my balls were aching for release and the slightest friction would have made me come. The silky caress of the panties on my shaft was exquisite torture and I wondered how much longer I would last before I exploded.

Taking a white silk full-slip, I gathered it up and lowered it over his head. It slid smoothly down his body moulding itself to his curves. I adjusted the shoulder straps to the correct length. Without being asked he picked up my red slip and helped me on with it.

With the petticoat now covering his body he seemed to relax. He kept glancing at his reflection in the mirror, turning this way and that to admire his curvaceous body. His erection was also prominent tenting the front of his panties and slip. He made no attempt at concealing it. I gave him a pair of Olivia's shoes with moderately high heels and pushed my feet into the sandals I worn earlier.

"How do you like it so far?" I asked him. "Do you think you will like being a girl?

His reply surprised and delighted me. "Oh Sal. I love it. I love the feel of the soft silky clothes and the way they make me look. I wish I could wear them all the time."

"Well I'm pleased you feel that way. I love wearing sexy lingerie too. Now, let's find you a nice dress to wear."

"What about make-up, Sal?" He asked.

"Excellent idea," I said, "but I don't have much of a selection. Only a couple of lipsticks and some eye shadow. And Chrissie, whenever I'm dressed in women's clothes you must call me Sally."

"Ok, Sally. I have lots of cosmetics in my room, and I know how to use them. Hang on a minute, I'll get them."

He swished off, the susurration of his stocking clad legs tantalizingly audible. I wondered why he had make-up with him; it was not the normal thing a young boy travelled with. He was back in a jiffy and I watched in admiration as he sat before my dressing table mirror, applying foundation, eye shadow, mascara, and lipstick. In a matter of minutes he had transformed his face from a pale mask into a thing of beauty.

"How…" I began.

"You're forgetting, Mummy is a cosmetics demonstrator. She taught me how to do it, and she uses me as a model. Would you like me to make up your face too?" he asked.

I nodded and we exchanged places. He quickly went to work using different colours and shades from his own. "Your complexion is much darker than mine, so you need a different treatment. A lighter eye shadow to bring out your brown eyes, a deeper shade of red on your lips and a pinker blusher." When he'd finished with the paints he took my hairbrush, released my ponytail and quickly brushed my hair into a more feminine style. "There you are, Sally. Now you look more like a woman." He was right. The simple application of a little colour to my eyes and lips, as well as the restyled hair, and I looked like an attractive female: but not nearly as attractive as he did.

The dress I'd chosen for him was one of him mother's I'd brought back with me. I'd worn it this morning and knew it looked good. It was a chocolate floral, silk chiffon sleeveless dress with a sweetheart neckline, frilly hem and a seven-inch split in the back of the skirt. It fell to just above his knees and was slightly gathered in the back with a small bow detail. Stooping down I held the dress open for him. He steadied himself with his hand on my shoulder as he carefully stepped into it. I worked it up over his hips and torso, and then put his arms through the shoulder straps. I adjusted the fitting round his false bust, and at his waist, and then drew the zip up the back, finally pressing the popper closed at the top. It fitted him to perfection, and the colour complimented his make-up. I gazed in awe at the most gorgeous young woman I'd ever seen.

"Now please help me with my dress, darling." I said, a lump of desire in my throat. He held the dress for me as I had done for him, and then zipped me up. As I turned to face him, I heard a gasp and his hand flew to his mouth in surprise.

" Sally. That's Mummy's little black cocktail dress."

"I know. I borrowed it this morning." I said, "When I saw it I just had to wear it. You don't mind do you?"

"Oh no. It's my favourite of all her dresses and I love to see her wearing it."

"Well how do I look?" I did a twirl for him. "Do I look as good as your mummy?"

"Oh, you look lovely, Sally. Just like a woman. I wouldn't know you were a man. Do I look OK?" he asked.

"Good enough to eat."

We stood side by side and examined each other and ourselves in the large mirror on the wall. My cock was so hard it hurt and was pushing out the front of my dress. I could see that Chrissie was in a similar state too.

"It's a pity about this though," I said, reaching across to grip his rod. "It spoils the line of your dress. A beautiful young woman shouldn't have a big cock sticking out like this. We shall have to do something about it."

"I don't understand why it's happening. Wearing these lovely clothes just makes it stick up like this." He said. "What can I do about it?"

"Don't worry Chrissie, it happens to me too," I said, indicating the enormous bulge at the front of my dress. "I have a guaranteed cure for it, though. Would you like me to do it to you?"

He nodded his head so I took his hand and led him to the bed. Pushing him gently he lay on his back with his feet on the floor. "Just relax, darling." I murmured. Kneeling between his legs I rubbed my hands up and down his nylon-covered thighs, slowly pushing the skirt of his dress and slip up till they were about his waist. His prick stood up vertically and pulsed as I gently pulled his panties down to his thighs. It wasn't a very big cock, maybe four inches, but it was rock hard. Taking the base of his penis between my thumb and the first two fingers I stroked him up and down a few times. I could hear his breath coming faster with his approaching orgasm. I told myself to hurry or I'd be too late. Leaning forward I took his beautiful cock into my mouth and sucked him in. It wasn't difficult to take the entire length in and I found that if I let his penis slip down my throat I could take his ball sack in as well. I raised my head gripping his hard tube tightly with my lips, and then swallowed the whole thing again. In a very short time, as I caressed his thighs and buttocks, I felt him tense and his hips begin to thrust up and down. With a loud groan he came, firing his delicious sperm deep into my throat. I swallowed eagerly, gulping down the surprisingly large quantity of semen. I kept him in my mouth, sucking till I'd milked the last drops of the sweet elixir from him and he'd withered to his normal flaccid state.

I remained kneeling between his legs, caressing and kissing his thighs, in particular the erotic band of white flesh above the tops of his stockings. Slowly he regained his composure, sat up on his elbows, and looked down at me. "Arh Sally, that was fantastic," he sighed, "I've never felt anything like that before. It was the most amazing experience I've ever had. Can I do the same for you in return?"

"You can if you'd like to."

"Oh Sally, I'd love to, but I don't know how. Will you tell me what to do?"

"Of course I will, my darling little boy girl." I said, almost exploding at the thought of instructing this sweet virgin in the art of fellatio. "First of all pull up your panties, tuck your pretty little cock away, and straighten your dress. Get your lipstick and re-do your lips, make them really red and thick."

Whilst he repaired his make-up I settled myself on the edge of the bed, lying back on by elbows so that I could watch him. "Now, while I sit here, get on your knees and kiss my feet." He looked puzzled for a second but did as I said. "Kiss my toes and the instep." I instructed. "Lift my feet in turn and kiss my high heels, lick them, and suck them as far into your mouth as you can. Good. Now kiss my ankles and my calves, rub and caress my legs. Work your way up to my knees, kiss and lick them, the front and the backs. Very good. Push you hands up under my skirt and fondle my thighs."

The feel of his lips and hands on my legs was driving me wild. I took several deep breaths in an effort to calm down. "Slowly push my skirt up so that you can see the bare skin above my nylons." I told him. "Kiss and lick all over it, don't miss anywhere. Ah, yes, your lips feel wonderful. Kiss my suspenders. Take the elastic tab in your teeth and snap them against the bare skin." He hesitated for a moment then did as I said. "Do it to each one. Arh, it stings so nicely."

Time to move on, I thought, I wasn't going to last much longer. "When I raise myself up push my skirt up round my waist, and pull the backs of my panties down over my arse cheeks." I thrust my hips upward to allow him to do so. He managed to get my tight skirt up sufficiently to grab the back of my panties and pull them down. "No, not the front, leave my cock covered for the moment."

He instinctively nuzzled my crutch. "Yes, that's good. Kiss my balls, and lick them. Rub your nose and cheeks against the underside of my cock and lick along its length." He was a natural student, following my instructions to the letter. "Now take the elastic waistband of my panties in your teeth and slowly pull them down to release my penis."

He tucked the band underneath my balls to stop it slipping up again without being told. "Now feast your eyes on my cock." I said. "I'll bet you've never seen one as big as this before."

My weapon glowed with heat and Chrissie could see the veins pulsing as blood surged along it. "You must hurry now. I am very near to coming." I croaked. "Take my balls in your left hand and gently squeeze them. Ahhh, not to hard. Grip the base of my prick with your right hand and squeeze as hard as you can." I was hoping this would delay my orgasm a little. "Kiss the head of my cock. Yes! That's it. Lick your tongue round the crown. Ahh! Open your mouth and take the head in. Arh, yes! Open as wide as you can and get as much into your mouth as you can. Wonderful! Your mouth is so hot. Now swirl your tongue round and round the head at the same time sucking it. Wriggle your tongue into the eye. Mmm, yes, yes that's good." I knew I couldn't last much longer. "Now pump my shaft with your right hand and squeeze my balls with the other." I gasped, barely able to hold back. "Arh yes, yes. I'm nearly there. When I come you must swallow it all. It is a crime to waste any man's seed. You mustn't loose a drop. Yes, Oh yes, keep sucking and wanking me. Arrrrhhhhhh. I'm cooooommmming. Drink. Drink my precious one. Swallow all of my cum. My cream is shooting into your adorable mouth. Suck. Suck me dry."

Despite his best efforts, he was unable to swallow all of my cum. I poured gallons into his mouth and throat, firing shot after shot into him. It spilt from the sides of his mouth and ran down his nose. It trickled down his chin and dripped into his cleavage. As he valiantly gulped down my outpourings the taste stirred a long forgotten memory in his mind. He suddenly remembered standing before his mirror as a child and seeing white stuff streaked across his face. He'd wiped it off with his finger and put it in his mouth; the taste had been the same.

After a long while, my copious discharged ceased and I lay back shattered and dranined. "Chrissie that was fantastic." I sighed in utter contentment. "You are fantastic. That's the best blowjob I ever had. Thank you, my angel. Come here."

He crawled on to the bed and lay beside me. I put my arms around him and gazed into his eyes, my heart bursting with love. My sperm covered his chin and lips and I couldn't resist the urge to lick him clean. The taste of my cum mixed with his lipstick was a heady cocktail. I pushed my tongue into his mouth and licked up the spunk that coated his tongue and teeth in a sticky film.

We remained like this for a long time. Kissing and cuddling, perfectly contend and relaxed, till finally and reluctantly we go up, straitened our clothes and went back down the stairs.

We spent the remainder of the day en-femme. It was so thrilling to be together dressed as two women. I taught Chrissie how to walk, sit and stand and encouraged him to use feminine mannerisms. He was a natural and quickly picked up the tricks. By bedtime he was behaving as though he had been born a girl. His performance as Juliet improved too.

Later after I had removed my make-up, changed into my nightie and slid into bed, Chrissie came to my room and asked. "Can I kiss you goodnight, Sally?"

For answer I held up the sheet as an invitation for him to enter the bed. He slid in beside me and immediately began kissing me. As our lips crushed together and our tongues fenced with each other, I felt his hand enfold my erection. I reached for his cock and found that it too was hard. Kissing passionately we masturbated each other to a satisfying orgasm.

 

Chapter Fifteen

Olivia phoned every few days but the news was not good. Her mother was diagnosed with terminal cancer and needed constant care and attention. She had been discharged from the hospital and was living out her final days at her home. She didn't know when she would return, she said, because she couldn't leave her mother's bedside. I assured her that Christopher was well, was attending school each day and was slowly becoming the complete Juliet. He was not being any trouble. In fact we were living together very comfortably and enjoying each other. Olivia was too distracted to pick-up on this reference. I continued teaching for three days per week and directing the play.

Each evening, as soon as Christopher arrived home from school, he'd shower and swap his uniform for female clothing. He couldn't wait to slip into his soft, silky feminine garb. If I had been teaching that day I'd do the same, otherwise I'd wait for him so that we could change together. Weekends we spent pampering ourselves, with long perfumed baths; we massaged each other with exotic oils, styled each other's hair, gave one another manicures and practiced the latest make-up techniques. We lounged in silken lingerie and dressed in our feminine finery from morning to night. I raided Olivia's wardrobe again and brought most of her clothes to my house. Christopher particularly loved wearing his mother's dresses, especially the black cocktail number as it made him feel closer to her. Whenever it was necessary to go out, we always wore lingerie under our masculine exteriors.

Christopher was now totally convincing as a woman and I eventually persuaded him it was time to make his first public appearance fully dressed. He made me promise that we'd only go somewhere there'd be no chance of being recognized. He was very nervous at first, but after we had casually sauntered, hand-in-hand, around a park and strolled along the high street looking into shop windows, he relaxed. When he was satisfied that no one was starting or pointing at him, and that every policeman he saw was not about to arrest him, he began to enjoy the experience. We had lunch in a pub then walked round a department store. He still wasn't confident enough to buy clothes but he did buy a lipstick from the cosmetics department. The woman at the counter even advised him on which colour suited him the best. He came away babbling with excitement; the woman had not suspected a thing and had assumed he was a girl.

I didn't attempt to pass during these daytime outings. I was afraid that next to Christopher I would have looked too obviously male, although he assured me I didn't. I did however; wear the androgynous suits and blouses whenever we went out together in the evenings. After a play or the cinema we often dined in candle lit restaurants. With my hair loose and my feminine suits anyone seeing us would assume we were two girlfriends out together for the evening. I easily passed in these situations.

The play was progressing well. I talked with the headmaster and obtained his permission for the pupils to attend school in their costumes on rehearsal days. Some of them were very good and it was obvious that the boys had put a lot of effort into creating an authentic period costume. But some were awful. The two boys playing Lady Montague and Lady Capulet looked like a couple of pantomime dames, and the guy playing Juliet's nurse appeared in a modern white lab coat and an apron with a big red cross on the bib.

I'd put a lot of thought into Juliet's dress. I'd visited Mrs Pettigrew again and found a long dress that had been made for a bridesmaid. With some careful alteration and the addition of several layers of stiff taffeta petticoats, a headdress and veil, I'd created a suitable Elizabethan dress.

For myself as Romeo, I'd visited a theatrical costumier and purchased a pair of bottle green, velvet knickerbockers and a sleeveless leather doublet. Mrs Pettigrew had also supplied a gorgeous white silk blouse with a lace jabot, balloon sleeves and lace cuffs.

The first day that we attended school in our costumes, Christopher was very nervous. Although he had ventured out many times en-femme, it had always been to places where he was not known. This time the whole class and most of the school would know who he was. I helped him choose his underwear and to dress. On this first occasion he forewent a bra and garter belt and opted for a fuscia, charmeuse classic cut camisole and tap panties. I insisted be wear the lingerie, as it would help him to feel more feminine. He wore neither tights nor stockings and refused to wear heels till he was more confident.

I, on the other hand, had no such inhibitions. I wore my sexiest bra, panties, and suspender belt with two pair of sheer stocking. The blouse, doublet and knickerbockers successfully concealed any evidence of my feminine lingerie. To stand in front of a class of teenage boys with raging hormones, and know that they were unaware I wore sexy undies, was extremely thrilling. I'd also found a pair of women's shoes with a chunky two-inch heal and a large silver buckle on the front that were perfect for the part.

After the initial teasing and joshing caused by their self-conscious embarrassment the class settled down, and the rehearsal went well. I noticed with a pang of jealousy that several of the boys were paying rather too much attention to Christopher. In fact, Benvolio was openly flirting with him.

After this first occasion the class became more relaxed and accustomed to wearing stage clothes. Christopher began wearing his full femme underwear of bra, panties, suspenders, stockings, and his breast forms. He began using a little cosmetic too, just a dab of blusher and lipstick at first but soon progressing to full facial make up. His hair was growing longer and one weekend we drove out of town and found an unisex hairdresser who cut and permed it into a very feminine style. He looked more beautiful each week. During rehearsals, when we were not on stage we would often exchange knowing looks. We each felt an exquisite thrill with the knowledge of what we secretly wore beneath our costumes, and that both our cocks were erect.

 

Chapter Sixteen

About a month after he had moved in with me I judged the moment had arrived for the next big step in his seduction. We slept together regularly and engaged in mutual masturbation and fellatio but I had not yet fucked him.

One evening, after supper we reclined together on the sofa watching television. I wore my pink satin, sheath nightie and Chrissie wore his mother's white lacy negligee. I slid my arm round his shoulder and nuzzled his ear. We started kissing. I pulled the ribbons that tied his negligee together under his bust and exposed his naked torso. I kissed his neck and chest and marvelled at his little budding breasts with their prominent, sensitive nipples. I kissed and sucked the delicate morsels then trailed kisses down across his stomach to his now rearing prick. I took it into my mouth and sucked it. I bobbed my head up and down his shaft and fondled his balls. He lay back on the couch spreading his legs wide. I slid to the floor between his open thighs and went to work on the rigid cock. My mouth left his cock to the attention of my stroking hand and moved to his scrotum. Taking it into my mouth I rolled the two hard nuts around with my tongue. His hips had begun to thrust up and down in an instinctive fucking motion. I let his testicles slip from my mouth and worked my tongue down between his legs till I found his sensitive little pink hole. I started licking his rosette and inserting my tongue. I felt him tense at the first touch but then he relaxed as I forced my tongue further into him. I tongue-fucked him till I heard his groans of pleasure and he was thoroughly lubricated. Gradually I began inserting my fingers into his anus, first one then a second. He was incredibly tight and I knew I would not be able to fuck him without a certain amount of pain.

When I reckoned he was loose enough I reached for the tube of KY jelly I'd left handy. I squeezed a long worm into his hole and worked it in with my fingers. I hitched my nightdress up round my waist and liberally covered my throbbing cock, then moved forward to press the head of my tool against his virgin pussy. I heard his sharp intake of breath as I pushed against him and felt the resistance of his sphincter.

"Relax, honey." I whispered, "Don't fight it. Just let it happen." I pushed harder and felt a slight give in his ring. I maintained a steady pressure and slowly the head of my cock breached his anal portal. He stifled a cry as the widest part of my cock-head entered him. I let my weight carry me forward till the full length of my shaft was buried in his rectum.

"That's good, sweetheart," I encouraged, "The worst is over; now it only gets better." Slowly and gently I began withdrawing till only the head remained inside him then I eased forward again. I repeated the strokes, gradually building up the momentum. I felt his arse begin to move to meet my forward thrusts and whimpers of pleasure escaped his lips. I increased the speed of my lunges and his legs lifted into the air allowing me deeper penetration of his depths.

"Yes. Faster." He suddenly cried. I obliged, building up the speed of my thrusts till I was pistoning in and out of his eager anus. "Arh, yes, Sally. That's so good. Fuck me Sally, fuck me hard."

As I pounded in and out of his tight little hole I reached behind my head, pulled my nightie off, and threw it to the floor. Now freed from all constraints I really began to move, fucking him in earnest. There was a constant stream of invective from him as he urged me on to harder and greater efforts. As with his natural talent for female mimicry he accepted the role of virgin bride with alacrity and enthusiasm. Despite my desire to continue fucking him indefinitely, the rising pressure of my approaching climax couldn't be denied any longer. My boiling sperm rushed up from my aching balls and jetted from the head of my cock deep into his bowels. I screamed with the release and buried myself in him to the hilt, shuddering and convulsing. As my spunk pumped into him I felt his rectal muscles gripping and releasing my shaft. His legs scissored round my waist trying to pull me even deeper into him, and not wanting me to stop.

It took several minutes for my breathing to return to normal. My cock collapsed and slithered from his pussy trailing cum. I rolled off him and lay on my back at his side. I noticed his stomach and chest were covered with the sticky white mess of his own ejaculation. "Wow. Chrissie," I managed to gasp. "That was fantastic. The best fuck I ever had. I hope I didn't hurt you."

"It hurt a little at first but later it was wonderful. I've never felt anything so good. Now I'm a complete woman. Oh. Thank you, Sally." He threw his arms round my neck and covered my face with kisses.

After that first time there was no stopping us. Our lovemaking became more and more wild. Chrissie sometimes fucked me, but much preferred the woman's role. We became insatiable for each other. We fucked before we arose in the morning, at lunchtime, in the evenings and during the night. Sometimes five or six times a day. Nor did we confine our fucking to the bedroom or the house; we would do it in the car, parked in lay-bys, in darkened cinemas, behind trees in the park, once even in the classroom at school during a break. The risk of exposure added to the excitement.

 

Chapter Seventeen

I'd been worried for some time about how things would work out when Olivia returned as she inevitably would. I had no idea how she would feel about her son's transformation into her daughter. Chrissie didn't seem too concerned. When I broached the subject, he just shrugged and said she wouldn't mind. I was not so sure. We both spoke to her regularly and kept her up to date on the plays progress and Christopher's schooling. Her mother's health continued to fail and it was only a matter of time before she died. Olivia hoped to arrange for nursing care so that she'd be able to leave her bedside long enough to attend the play.

Four days before the performance she died. Olivia phoned to say that she wouldn't be able to make it after all. There were the funeral arrangements to be made and the burial to attend, the reading of her will and the usual legal details to be settled. But she wished us good luck and told us to 'break a leg.'

The one and only performance of my production of Romeo and Juliet, by William Shakespeare, staring Salvador DiMarco as Romeo, and Christopher DeCoursey as Juliet, was a greater success than I had dared to hope. Everyone remembered his lines and got their cues right. No one corpsed or froze up and the acting though not great was adequate. We received three curtain calls after the final scene, and then in front of a packed hall the headmaster presented Juliet with a bouquet of flowers. I did not know who was the more embarrassed, the head' handing flowers to a boy dressed as a girl, or Christopher receiving them from the school's authority figure knowing he wore sexy lingerie under his dress.

He made a short speech thanking the cast for all the effort they had put into the production, for the leading man and leading lady for their fine performances, and he especially thanked me for staging the whole show. He would not have been so fulsome with his praise had he known that Romeo was wearing a black satin, lace trimmed basque, high cut bikini panties and nylon stockings underneath his costume. He wished us all a happy Christmas and hoped we had an enjoyable holiday.

Chrissie and I dressed up that evening to celebrate our success. I'd given Christopher a beautiful bra, panty and suspender set from Victoria's Secret as a Christmas present. His growing breasts nicely filled the 34B bra cups and his nipples dimpled the flimsy lace covering. Over them he wore his mother's black velvet cocktail dress, honey coloured, fifteen denier nylons and a pair of my three-inch heeled black court shoes. He took extra care with his hair, make-up and nails. He put in gold hoop earrings and borrowed Olivia's three-stand pearl necklace. He looked especially desirable tonight. I wore my powder-blue suit with the skirt and a yellow silk blouse. I left four buttons undone so that the front gaped to reveal tantalizing glimpses of my by lacy black bra. Chrissie hung the gold necklace round my neck that was his Christmas present to me.

I'd bought a bottle of champagne on our way home and when everything was ready I opened it, poured two glasses of the fizzy liquid and toasted my love's good health. We sipped the sparkling wine looking into each other eyes. I took the glass from his manicured hand and placed it with mine on the side table. I moved closer and took him in my arms, "Happy Christmas, my darling," I whispered, then pressed my lips on his in a soft, tender loving kiss. Our bodies pressed together and I felt his soft breasts against mine. Our kiss became more passionate and our tongues danced together.

It was at this moment that Olivia walked in.

We jumped apart when the door suddenly opened. "Oh! I'm so sorry, Sally. I didn't mean to barge in on you," she said, flustered. "I should have knocked. If I'd know you had such pretty company I would not have disturbed you." She obviously recognized me, and was not at all surprised that I was cross-dressed, but she didn't seem to know her own son. Considering the changes he'd undergone since she had left three months ago, it was not really surprising.

"Olivia!" I said, straightening my jacket and blouse. "How lovely to see you again. I didn't expect to see you till after the holiday. I was terribly sorry to hear of your mother's death."

"Yes it was sad, but for the best. She suffered a lot towards the end. I managed to settle her estate and get her affairs in order before the lawyers disappeared for the holiday, so I was able to get home sooner. Where's Christopher?"

She had glanced at him several times, and I could see from her look that she thought she should know who it was. "Mummy, don't you recognize me?" he said taking a step forward.

Her hand flew to her mouth and she gasped in shock. "Christopher. Chrissie. Is it really you?"

"Yes Mummy, it's me. Do you like my new image?" he enquired. He took her in his arms hugged her and kissed her pale lips leaving a smudge of lipstick behind.

"Oh, yes darling." She said holding him at arms-length. "You're beautiful. You are such a lovely young woman. You quite take my breath away."

"Have some champers, Olivia," I said pouring another glass. "It seems we have a lot to talk about."

Chapter Eighteen

After the initial shock of seeing her son transmogrified into a daughter, she quickly accepted the fact. She always knew he had a strong feminine side to his character, she explained, in fact she had been encouraging him to express it more for the last year or so. She dreaded the onset of puberty, she said, when his voice would break and he'd start growing body hair and shaving. (I made a mental note to tell her about the hormone pills that he was taking.) She had been buying girls' jeans and tops as well as underwear for him for a long while now. She had taught him the art of make-up and loved to use him as a model for her demonstrations. She always talked with him about intimate female subjects and whenever she was with her girl friends, he would be included in their conversations. Ever since the awful experience with her ex-husband and his perverted friends, she had wished he were the daughter she longed for, and not her son. Now it appeared he had become what she had always wanted.

"Chrissie, I hope you don't hate me for wanting a daughter instead of a son." She admitted, after her lengthy explanation. "It's a secret I've had all these years, but I do love you and want us to be fiends."

"Oh, Mummy. Of course I don't hate you. It's what I want too. Sally has shown me the joys of being a woman, and my dearest wish is to become one completely. If only it were possible."

Olivia looked thoughtful for a while, and then said. "It may be possible. I've never told you this before, but your grandmother was an extremely wealthy woman; wealthier, even than I suspected."

Her late husband had been a financial genius who had made a fortune on the world's stock markets. He had established a huge portfolio of shares and with the profits had bought property. He owned office blocks, warehouses, shopping malls, residential houses and apartment buildings, all earning rents. He owned properties all over the country and abroad, including a vast estate in the Scottish highlands. When he'd died suddenly from a heart attack, she took over running the business. Although, as she explained during the long hours Olivia sat at her bedside, it didn't require much work, because Arthur Cavendish had set things up in such a way that she only had to attend board meetings once a month and sign the occasional document.

"And as I'm her sole heir I've inherited the lot. All I have to do is to continue attending the board meetings. We could sell up here and move to the estate in Scotland. There's a big old house, with dozens of rooms and a couple of old retainers who help out in the house and the grounds. No one will know us. You could start a new life as a woman and my daughter. What do you say?"

Chrissie clapped his hands in excitement. "Oh Mummy, it sounds the perfect solution." He hesitated as the implications went through his mind. "But what about Sally? I couldn't leave him, and what about my schooling? What about your work too? There seems to be so many problems."

"Don't you understand? I'm a rich woman now, a millionaire. A multi-millionaire even. I'm not sure how much I'm worth, but I never need to work again. As for Sally, he could come and live with us. I could engage him as your private tutor or should I say your governess." She winked at me, acknowledging my transvestism with her joke. "What about it Sally? Would you be willing to sell your house and come and live with us?"

"Definitely." I said. "I'd leave in the morning. There's nothing to keep me here, and I have no ties. I'll resign my job as soon as I can. There's nothing more I'd love, than to be Chrissie's governess and tutor. I could also be your companion and confidante too. The idea of a new start and a new life in Scotland is very appealing."

"It's settled then." She declared. "Fill up the glasses, Sally, and let's drink a toast to our new future together."

The end

(Or the beginning?)

 

Thank you for taking the time to read this story. I hope you enjoyed it. If you did, or even if you didn't, I would appreciate your feedback and encouragement. I can be contacted at belle.gordon@excite.com or leave a review on the website. If you would like to re-produce all, or part of it, please ask my permission. Till the next time. B.G.

  

  

  

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