The Holiday Of A Lifetime
by Susan Kershaw
"Bye darling, have a lovely time and I'll see you in two weeks" said Tony's mother as she kissed him goodbye. "Take good care of my baby won't you Sybil he's very precious you know" The two women hugged before saying goodbye and Tony waved to his mother as she drove away, turning his thoughts to the next fortnight which would be spent with his aunt Sybil. Aunt Sybil was his mothers step sister and Tony always felt strangely drawn to her. Some might say she was slightly overweight and some might say she was slightly past her best years but not Tony. He loved the way she was always immaculately dressed in ultra-feminine clothes, always immaculately made up and always smelled of the most exquisite French perfumes. Being a rather prissy and young looking sixteen year old, Tony enjoyed her company because when he was with her he felt free from the pressure to be a typical boy that was always put upon him by his friends.
Now he had a whole fortnight to look forward to and as he entered the lounge his aunt looked up from the sofa in which she sat." There you are darling" she said "I've prepared your room for you. After supper I thought it might be nice to watch a video together, what do you think?" "Sounds fine to me auntie" replied Tony and with that Aunt Sybil arose from her sofa to show Tony to his room. Tony obediently followed his aunt up the stairs, along the corridor and in to the room he would occupy for the next two weeks, but as she pushed open the door, he got a surprise.
"This is a girl's room auntie, I can't stay here"
"Well I know it's not what you're used to poppet, but it's the only room available, and I'm sure you'll get used to it, besides, I won't tell anyone if you don't." This reassured Tony so he reluctantly agreed to bring his things in to the room. "Now you make yourself comfortable while I prepare supper and I'll see you downstairs shortly" said his aunt, closing the door behind her.
Tony sat on the bed and looked around him. The bed he was sitting on had an ornate headboard in white with gold leaf trimmings. The duvet was pink with a frilly valance that reached the soft ,cream carpet. The curtains matched the bedclothes and contrasted with the white nets. It seemed that everything in the room was either pink, white or cream. Over in the corner was a giant walk-in wardrobe with full length mirrors for doors and at the foot of the bed was a girl's dressing table with three adjustable mirrors. The gold leaf trimmings on white matched the bed and the wardrobe. In front of the dressing table nestled a round frilly stool, the type on which a girl would sit to do her make-up. Finally, next to the bed was a small table with a white vase containing fresh pink and white carnations that immediately became the focal point of the room ."Oh well," thought Tony, "At least no-one will know."
After a light supper, Tony sat beside his aunt on her large comfortable sofa, while she sorted through her favourite videos. "How about this one darling It's Shirley Temple." she said "Shirley who?" thought Tony, but rather than make a fuss he agreed to his aunt's choice.
Twenty minutes in to the film Tony had become completely captivated by the little girl he saw before him. Watching her perform "The Good Ship Lollipop" in her cute little dress, bubble cut hairstyle, ankle socks and Mary Jane shoes had an affect on Tony that he did not quite understand and sitting next to his ultra-feminine aunt only exacerbated this feeling, somewhere between deep unease end thrilling exhilaration. "Oh darling, isn't she divine" said his aunt as they both watched, fascinated. Totally immersed in the moment, and being caught off guard, Tony gasped" Yes auntie, who wouldn't want to be just like her?.......
His aunt, surprised, looked quizzically at Tony and said "I'm sorry darling, what did you say?" "Well I only meant" said Tony, suddenly realising that he had unwittingly given away a secret part of himself," that er, well, she does look really gorgeous" "Yes Tony," said his aunt, "but you also said that anyone would like to be like her, does that mean boys as well?" Tony's mind was racing, how was he going to get out of this one? "Well I suppose some boys would auntie" he stammered, wishing immediately he could retract the words. "And would you be one of those boys?" enquired Aunt Sybil."
"Oh come on Tony, yes or no?"
"If I said yes, would you promise not to tell anyone?" pleaded Tony, biting his lip and trying to hold back a flood of tears. "Of course darling, after all, I am already keeping the secret of your sleeping in a girl's room, so why should I not keep this one?" she said as a wave of tenderness swept over her. "In that case yes auntie, I am on of those boys" said Tony, hoping his aunt would not be angry.
After what seemed like an age, Aunt Sybil took Tony's hand in hers and led him upstairs to his bedroom. Opening the wardrobe door his aunt peered in and slowly, without saying a word drew out the most gorgeous dress and held it against Tony. After a few moments thought, aunt Sybil said" I think this should fit you just nicely, don't you Tony?"
Tony was dumbfounded. He stared at the dress. It had a cute little peter pan collar, puffed sleeves and the most exquisitely flared skirt one could ever imagine. It was made of white satin and dotted with red rosebuds all over. The hem of the skirt was finished with red piping and the bodice was tied at the back with a red sash.
"Er, I'm sorry auntie," said Tony," I don't understand, you mean you want me to wear this dress?" "Well you did say you would love to be like Shirley Temple dear, and what could be better than this dress to make you look like her?" replied his aunt. His head swimming, Tony stammered that wearing a dress alone wouldn't make him look like Shirley Temple if he only had boy's clothes to wear with it, but his aunt wouldn't hear of it. Reaching in to his chest of drawers she produced a pair of the frilliest knickers Tony had ever seen, and he gasped at the sight of them . "Here try these, and here's a pair of ankle socks to match" said Aunt Sybil. As Tony stared at all this exquisite femininity, trying to take in all that it meant, Aunt Sybil turned back to the wardrobe and from the base pulled out a pair of red patent leather Mary Jane shoes." Here you are my angel," she said, "the knickers, socks and shoes all match the dress so surely there can be no excuse now can there?"
Tony struggled to think for a second and then said "What about my hair? auntie, it's too short for a girl" "Ah yes," said his aunt "luckily I was an actress before my husband left me so I can help you there," and so saying she turned again to Tony's wardrobe and produced a pretty, soft, blonde wig styled into ringlets just like any little girl would love to have in their hair. Realising there really was no excuse now, Tony took a deep breath and said" "O.k. auntie, I'll do it, but only if you promise not to tell anyone" Aunt Sybil pouted her crimson lips, and putting her forefinger gently to them softly breathed "Mums the word."
Now Tony had given his permission to Aunt Sybil there really was no turning back. His thoughts had drifted away in a reverie but he was brought abruptly back to reality by his aunt's next words. "Come on my sweet, get your clothes off." Thinking about wearing girls' clothes had made Tony forget that he would have to undress first and this unnerved him. Sensing her nephew's hesitancy Aunt Sybil changed her approach slightly. "Look darling," she said, "I can see you are a bit embarrassed about undressing in front of me, but I need to check that you have a girlish enough body to wear these lovely clothes, so I will look away whilst you quickly undress and put your frilly knickers on." Tony did as she said and on turning around again she picked up his clothes and locked them in a drawer saying "I don't think we'll be needing these for a while."
Turning back to Tony, she stared hard at him. "Yes you do have lovely soft skin and your figure is rather girlish so fortunately we don't have to do anything much before we dress you. Put your shoes and socks on darling" she instructed. Tony pulled on the socks and fiddled with the buckles of his shoes before finally getting everything right. Glancing over to the mirror Tony caught sight of himself and marvelled at the delicious feeling that the sight of himself in his undies gave him. "Now poppet," interjected his aunt. "I think before we put your dress on, you ought to wear a petticoat, after all we want your skirt to stand out don't we?" Tony did not feel qualified to argue and so he nodded meekly in agreement. The petticoat she took out of the wardrobe was white with a silken bodice and stiff layers of underskirt. There was a little pink bow right at the top centre. Pulling the petticoat obediently over his head, Tony felt the delicious sensation of the cool silky material around his body. "Now darling," said Aunt Sybil, "I am going to make your face up, so it is extremely important that you do not look in the mirror until you have your dress and wig on. Do you understand?" "Yes auntie" replied Tony meekly and he started to wonder if he had done the right thing in allowing his auntie to dress him up.
The next twenty minutes were spent with Tony sitting at the make-up stool, back to the mirror, drinking in the delicious aromas of the creams, powders and other substances that she applied to his face. The close proximity of his aunt as she put on his make-up had a profound affect on Tony and he felt a stirring in his knickers. Luckily his petticoat helped to conceal any protrusion.
Aunt Sybil made full use of the cosmetics at her disposal. She applied Tony's foundation, eye shadow, mascara, powder, blusher and lipstick with an expert touch and at last pronounced herself happy with the results. "Stand up now sweetie" bade Aunt Sybil "and raise your arms above your head so I can put your dress on." Carefully lowering the dress over his head and shoulders so as not to smudge his make-up, she zipped it up and tied the sash at the back. She then fussed with the skirt to make sure that it stood out properly. As she teased out the skirt, Tony stood still like the good little girl he was becoming. His wig came next and Aunt Sybil brushed out the curls to give as soft a look as possible before tying two red ribbons to either side .Stepping back to inspect her work, she pondered for a moment and said "I know just the thing to finish off your outfit darling" and out of Tony's drawer she produced a pair of pretty little pearl drop earrings which she clipped on to his lobes. A matching pearl necklace followed, along with some white lace gloves and a white patent leather handbag.
"Now close your eyes my angel and take my hand as I lead you over to the mirror. Keep them closed 'till I tell you to open them."
She led the little girl to the mirror and after a moments pause said "Viola. Open them now."
Tony opened his eyes and stared in amazement, unable to utter a sound. There before him stood the prettiest little girl he had ever seen. Even prettier than Shirley Temple herself. Her hair framed a soft feminine face, her beautifully made up eyes stared wide in wonder. Her baby pink lips formed a cupids bow.
This heavenly face sat on top of a slim girl's body enveloped in the sweetest dress imaginable, its soft folds and ruffles accentuated by a short full skirt held out by the most gorgeous of lace petticoats. The red patent Mary Jane shoes perfectly complemented the red rosebuds on the dress and the little ankle socks completed the picture.
Recovering his powers of speech Tony murmured "Auntie, she's beautiful, can she really be me?" "Of course my sweet, who else could she be?" replied Aunt Sybil "She's like a little sister for Shirley Temple don't you think? I know, lets call her Susie Temple-yes, Susie, that's a very pretty name." From that moment on there really was no doubt, Tony had become Susie, at least as far as Aunt Sybil was concerned ."Now come along Susie," said Aunt Sybil, "how about a nice curtsey for your auntie, do you think you could manage that?" "I may have to practise a bit auntie, but I will try if you want me to." replied Tony ."Good girl." said his aunt, "I'll leave you to practise in front of the mirror and when you feel you are ready I'll come back to watch, is that ok?" Tony replied that it would be, so his aunt left the room to allow him to practise.
Alone in his room Tony started practising his curtsey but each time, as he dropped towards the floor, he realised that he was allowing his knickers to show as his skirt flew upward. Much as the sight of his frilly panties was very pleasing to Tony, he really wanted to curtsey properly for his aunt and so he spent the next hour perfecting his technique. At last, when he was really sure he could do it properly he called downstairs to Aunt Sybil. "I'm ready now auntie, can you come up please?" His aunt entered the room and sitting on the bed, she watched as her nephew took hold of the hem of his skirt, bent his knees and dropped slowly to the floor in a perfect curtsey. Aunt Sybil clapped her hands in delight and smiled warmly at him. As she hugged Tony to her ample bosom she said "That's beautiful Susie, you really are a doll you know." Tony thanked his aunt for the compliment before repeating the action. "You know darling" said Aunt Sybil," I'll let you in to a little secret. I've always wanted a daughter like you but unfortunately it never happened for me, but if you could be my niece it would really make me happy" Tony wasn't sure if he wanted to be a girl all the time but he loved his aunt and he did want to make her happy so after a few moments thought he said "Well I'm not sure if I want to be a girl forever auntie but if it makes you happy then I am willing to be your niece for the rest of the holiday, how would that be?" Aunt Sybil smiled warmly again, gave Tony a lingering kiss on his painted lips and said "Thank you darling, you really are wonderful, we're going to have such a lovely time, and of course, we wont tell anyone, will we?"
By now it was starting to get late so Aunt Sybil said" Come on Susie, it's time for bed, I'll see if I can find a nightie for you" She searched through Tony's wardrobe and pulled out a beautiful, see-through baby doll in lemon with matching panties. Both had white lace edging. Tony was reluctant to take his dress off but looking at the nightie he realised it might not be such a sacrifice after all. Before he could undress, his aunt called him over towards her. Tony couldn't imagine what she might want, but dutifully did her bidding. "Now Susie, you've been a very good girl today, so I'd like to give you a reward, take your knickers off and give them to me please" Wondering what his reward could be, Tony slid down his panties and stepped out of them before passing the gorgeous frillies to his aunt. Pulling up a stool she sat down and ordered Tony to stand next to her. "Now my pretty, I want you to look in the mirror and relax, o.k?" "Yes auntie" replied Tony, still wondering what was going to happen. Lifting the hem of his skirt, Aunt Sybil took the knickers in her hand, wrapped them around his erect symbol and slowly began to massage the feminised boy. "That's it darling," she cooed, "Relax and enjoy your pretty clothes." Tony took a long look in the mirror and shuddered with pleasure as the pretty little girl looked back at him.
Soon after, Tony was in his nightie being tucked up in his bed by Aunt Sybil, and after a kiss goodnight he snuggled down to a well deserved sleep.
* * * * * * * * * * * * * * * *
When Tony awoke next morning, his first thought was that the previous night must have been a dream, but a glance down at his nightie told him otherwise. He could hear his aunt moving about downstairs so plucking up his courage he ventured out of his bedroom and went downstairs to see her. "Good morning darling" she cried as she saw him standing in the door of the kitchen. "My, don't you look lovely in your nightie, and your panties look sooooo fetching." Realising his micro-length nightie exposed his knickers for all the world to see, Tony blushed, but his aunt put him at his ease. "It's o.k. darling, we're all girls together here, there's no need to be embarrassed." she said, and Tony relaxed ."I'll make some breakfast, my angel and then I need to have a talk with you."
Over breakfast Aunt Sybil told Tony that she had to go out the shops that morning but would be back by lunchtime and so Tony would have to amuse himself for a few hours." I'll get you dressed first poppet, and then I'll go, but don't worry' I'll be back as soon as I can." she said as she led him to the bathroom to get freshened up for the day. Once nicely cleaned and scrubbed, Tony followed Aunt Sybil in to his bedroom to get dressed. She selected a pretty blue dress from his wardrobe with a fitted bodice, Peter Pan collar and puff sleeves. The skirt was very full with a sewn in petticoat, the lace hem of which peeked out from under the skirt. "Do you like this one darling?" she asked Tony, and getting a shy nod of the head in response she laid it out on his bed ready for use. "Now your undies my angel" she said as she searched through Tony's chest of drawers. A pair of white frilly knickers were first to emerge followed by a silky white camisole top with thin shoulder straps. A pair of knee length white socks and a pair of pale blue Mary Jane shoes followed soon after. Aunt Sybil turned her back so that Tony could slip in to his undies and once in his vest and knickers she helped him on with his shoes and socks. Tony was now ready to put his dress on so Aunt Sybil took it off the hanger and unzipped the back for Tony to step into. Before allowing him to see himself in the mirror, Aunt Sybil put on his wig and tied two blue ribbons in his curls to match his dress, commenting that it shouldn't be long before his own hair was long enough to be styled in to a suitable fashion for her little lady. "But auntie" said Tony quizzically, "I thought I was only going to be a girl for a couple of weeks Wasn't I?" "Oh yes replied Aunt Sybil rather too quickly, "Sorry darling, I forgot."
Turning her attention back to his dress, she flounced out his skirt and brushed his locks before turning him toward the mirror. Once again, Tony stared into the mirror in amazement. He was shocked, but secretly delighted at his appearance. "Oh isn't she pretty" cooed Aunt Sybil as Tony turned from side to side to check his look ."You know darling, from the look on your face I'd say you prefer being a girl to being a boy." "Oh auntie please don't tease" said Tony, looking to the floor. "Sorry petal" she replied, "I'll behave myself, I promise. It's just that you look so lovely, I get carried away sometimes and I want to take you in my arms and smother you in kisses." Tony had to admit to himself that that would not be an unpleasant experience.
Soon after Tony was kissing Aunt Sybil goodbye in the hallway "See you in a couple of hours my sweet, be a good girl for me won't you" she said as she bustled out of the door. "I will auntie" replied Tony and he returned to the living room to finish watching the Shirley Temple video.
When the video was finished, Tony wandered round the house admiring his reflection each time he passed a mirror, and generally trying to fully appreciate all that had happened in the last twenty-four hours. Slightly bored,(if it is possible for a boy in a dress to be bored)he wandered in to the lounge and on the coffee table he noticed a letter. Idly picking up the letter he started to read, and what he read made his heart leap:-
As you know ,I am going away for a year to be with my new husband who has to go abroad for his job. I know it will be hard on Tony but since his father died I have not been able to find a man to make me happy until now. He and Tony do not get on very well so I would like you to look after him for me as I know you love him as much as I do. It would probably be better if he wasn't given the news all in one go, so I suggest that we tell him it is only for a fortnight and then you can break it gently to him while he is with you. He is a sensitive little flower, but I am sure that with tact and diplomacy and your undoubted love and kindness you will be able to make him feel safe and secure. As you also know, for some time now I have been finding girl's underwear in his room .I think he must have "borrowed" them from his cousins when they have stayed here. I haven't discussed it with him but I think that he secretly likes feminine things and as an ultra-feminine lady yourself, I think you are perfectly suited to look after him. If anyone can deal with this side of his nature I am sure it is you. Please take care of him and tell him how much I love him.
Your ever loving step sister,
Tony stared at the letter, scarcely able to believe his eyes. "So it was a trick" he thought. "I'm to live here as a girl until my mother comes back. I can't believe it" and he sank down in Aunt Sybil's sofa in shock. Lost in his thoughts, his mind reeled as he took in the reality of his situation, and losing all track of time he sat there dazed and confused……………………
"Coo-ee darling, I'm back."………..Aunt Sybil's tinkling voice brought Tony sharply back to the present. She stood in the doorway with her arms full of shopping bags of every description as Tony stood up with the letter in his hand. "I've got some lovely presents for you my precious………..oh." She dropped the shopping to the floor as she realised that Tony had read the letter.
"Auntie you lied to me" said Tony, his voice trembling. "Why?" "It's for the best my darling" she replied. "If you had known before you came here you might have refused to come, and your mother and I didn't want to risk that. We both love you so much that the thought of you going somewhere else was unbearable."
Put this way, it suddenly didn't seem so bad to Tony. After all, it was done because his mother and aunt loved him, and he did so love them too. "I do like staying here auntie. It was just such a shock to find out the way I did, that's all, but I think I can get used to the idea as long as there are no more shocks to come." said Tony.
Aunt Sybil sat down on the sofa and bade Tony to come over to her. "Sit on my lap darling" she said. Tony did as she said and she cradled him in her arms. Kissing him tenderly she sought to reassure her nephew. "Listen honey, I want you to know that while you are here with me you are completely free to do or be anything you want. You can be a little girl, a teenage miss, or maybe a schoolgirl. Perhaps you'd like to be my maid or possibly wear a nurse's uniform." Tony felt a stirring in his knickers. "You can even be a boy if you really want." she went on. The stirring in Tony's knickers subsided a little.
"The point is, my sweet, you are totally in charge of your own destiny. All you have to do is decide." said Aunt Sybil, stroking his hair. As far as Tony was concerned there was no real decision to be made. "I have decided auntie. I want to stay here as your niece if you'll have me." he said with as much decisiveness as he could muster. "Oh darling, bless you, " said Aunt Sybil as she hugged Tony tightly.
Tony felt the stirring in his knickers again.
* * * * * * * * * * * * * * * *
Over lunch, Aunt Sybil told Tony of her plans for him. "We'll have a lovely two weeks together my angel and after that your education can begin in earnest." It was obvious from the look on Tony's face that he didn't quite understand, so Aunt Sybil went on to explain. "You see my darling, if you want to be a proper girl you will have to learn the art of being feminine so I will need to teach you such things as deportment, beauty therapy, dressmaking and all the other skills that make a complete female." Sensing some apprehension on Tony's part she sought to reassure him. "Don't worry my precious, I'm an excellent teacher and I'm sure you will be a willing pupil. By the time I'm finished with you no-one will ever have any reason to think anything other than that you are a beautiful girl." Tony relaxed a little at this news but still found the thought of it all both daunting and exciting at the same time.
"But first to more immediate pleasures." said Aunt Sybil." A nice bubble bath for you young lady, and then we can have some frilly fun together. How does that sound?" I'll leave it to you dear reader to guess how that sounded to Tony.
Aunt Sybil ran the bath and added some scented oils to the water, and by the time Tony entered the bathroom everything was ready for him. He slipped off his dress and stepped out of his shoes and socks but still baulked at taking his knickers off in front of his aunt. "Oh you silly goose" said Aunt Sybil, and before Tony could realise she gave a quick tug on his panties and they slithered down around his ankles. "There, that didn't hurt did it?" she said ."You really must learn not to be so shy in front of me my sweet. Alone in this house together we can be totally relaxed in each others company." Tony could see the logic in what she had to say so he resolved to try and be a bit less inhibited in future." Before you get in the bath darling, I would like you to use this cream all over. It's a depilatory cream and it will help to keep your skin free from any unwanted hair." He did as she had instructed before slipping in to the luxurious foam. "While you are in the bath honey, I will go and prepare your room" said Aunt Sybil. "I'll see you when you get out. I've left some things for you to put on and don't forget to dust yourself down with talcum powder will you" "No auntie" replied Tony and he lay back to luxuriate in his surroundings.
After a nice soak in the bath, Tony got out and dried himself with a large, fluffy pink towel and dusted himself with some scented talcum powder from a glass jar by the bath. His smooth skin tingled sensuously as he applied the talc with a powder puff from the jar. Next he put on the things his aunt had left for him. First, a pair of white nylon briefs, silky across the buttocks, with a pretty lace panel at the front. Two pretty pink bows decorated either side. Then he put on the negligee that Aunt Sybil had left which was also white and silky and trimmed with white lace. This left a pair of pink fluffy mules which Tony slipped on his feet before making his way to his room. On entering the room Tony found Aunt Sybil with masses of shopping bags on the bed which she was busily putting away in the appropriate places. Casting an approving eye over Tony's appearance, Aunt Sybil explained to him what she was doing. "I'll let you in to a little secret my petal" she said. "Once I knew you were definitely coming to stay with me I rushed out and ordered some girly things for you. Here, let me show you what you have so far. First, your lingerie." Pulling open the top drawer of his chest of drawers, Aunt Sybil noticed Tony gasp as his eyes fell on a dazzling array of panties. "The top drawer is for your knickers my sweet, you can look through them at your leisure. The next drawer down is for petticoats, the one after that suspender belts and stockings, and the bottom drawer is for your bras" "I haven't got anything to put in my bras auntie" said Tony, slightly mystified as to why his aunt should buy him such garments. "Oh don't worry darling" his aunt replied, "I've also got you some falsies. Once you have learned to use them no-one will ever know the difference. Besides you will soon be growing your own breasts." "But auntie, I can't grow breasts, I'm a boy" protested Tony. "Where there's a will there's a way." said his aunt enigmatically.
Next Aunt Sybil turned her attention to his outer wear. Flinging open his wardrobe door she said "This should be enough to keep you going for a while." And Tony went weak at the knees as he feasted his eyes on a wardrobe stuffed full of skirts, blouses and dresses of every description, ranging from pretty summer frocks to slinky evening wear. At the bottom of the wardrobe were at least a dozen pairs of shoes that ranged from Mary Janes through to dainty kitten heels and strappy stilettos. Not quite able to take in all this heady excitement, Tony was by now almost speechless as Aunt Sybil moved on to the next stunning revelation. "Your dressing table is ready for you too darling" she said as Tony moved his gaze to a fabulous array of cosmetics laid out on the surface. Foundation, mascara, eyeliner, powders and lipsticks lay there awaiting his use. Finally, around the room were several wigs on stands each styled in the most gorgeously feminine fashion.
When Tony had regained his powers of speech he flung his arms round Aunt Sybil saying" Thank you auntie, you must really love me to go to all this trouble." and he kissed her painted lips tenderly. "Steady on darling, you'll get me all excited." said his aunt. Tony wasn't sure what she meant by this remark, but for his part the close proximity of his aunt gave him a feeling he rather liked.
Aunt Sybil patted Tony on the bottom and said" Come on Susie, let's get you properly dressed. We'll start by painting your nails." She picked up a bottle of nail varnish from the dressing table and ten minutes later Tony was marvelling at how pretty his hands and feet had become with just a touch of colour. Next she made up his face. She took her time with this, taking care to explain to her pupil the importance of paying attention to detail. First came the foundation, which she explained must be applied evenly and blended in to avoid patchiness. Then came the eye shadow and again Aunt Sybil showed Tony how to apply it carefully and how to mix the colours to get the right look. Eyeliner and mascara were next. "Start from the centre of the eyelid darling, and work outwards. This will make your eyes look further apart." she told him. Powder, rouge and lipstick followed and now Tony was ready to put on his wig, All the wigs were top quality and made with real hair to give the most natural look possible. Aunt Sybil chose a chestnut brown, shoulder length wig styled in soft waves and when Tony saw himself in the mirror he nearly fainted with delight. "Here darling, you can have these as a gift from me. I used to wear them when I was your age but they will look better on you now." said Aunt Sybil, and she presented him with a heart shaped locket on a thin gold chain which she placed round his neck. Then she put a pretty charm bracelet, again in gold on his wrist and attached a dainty pair of earrings to his ears that matched the bracelet with two tiny ballerinas dangling from them.
The rest of the day was devoted to Tony's education. Aunt Sybil showed him how to put on a suspender belt and how to attach his stockings to them. She explained the difference between briefs and french knickers and about the different materials used to make them. All afternoon Tony listened eagerly as Aunt Sybil imparted her considerable knowledge of how to be as feminine as possible. The session ended with a lesson on how to put on a bra and how to make his falsies look realistic.
Tony loved his falsies. They were extremely natural looking in flesh colour with pert nipples. They were filled with a fluid that gave them a realistic bounce. Attached to his chest and nestled in the cups of his bra it was difficult to detect that they were not real.
Tony also loved the various images that the fabulous outfits allowed him to create. He loved being a little girl, but he also loved being a teenage miss. He particularly enjoyed being a glamour model and becoming a sex kitten in sheer stockings, cocktail dress and strappy stilettos. "Oh auntie" said Tony, "Isn't it wonderful, I wish it could go on forever." "There's no reason why it can't, my precious" replied Aunt Sybil. "As long as the two of us are here together there is nothing anyone can do to stop us doing whatever we want." Overcome with happiness Tony hugged his aunt who returned his affection with interest.
By now it was getting late, so Aunt Sybil suggested that Tony select a nightie from his drawer and get ready for bed. He chose a silky black baby doll with matching panties and quickly changed in to it, checking his look in the mirror as he put it on. Satisfied with the image before him, he clambered in to bed to settle down to sleep, but before he could pull the duvet over him his aunt approached for a goodnight kiss. As she planted her lips tenderly on his, her fingers tiptoed their down to the front of Tony's panties. Gently caressing the silky material she could feel a hard bulge underneath, so knowing Tony would not object, she slipped her hand inside and took hold of the only part of Tony that was still male. Skilfully massaging the bulge in Tony's knickers, Aunt Sybil brought the boy to a thunderous climax. By the time she had closed the door, an exhausted Tony was fast asleep.
* * * * * * * * * * * * * * * * * *
Refreshed after a lovely sleep and ready to face a new day, Tony arose the next morning to find his aunt busily preparing for the day's activities ."I have a special treat for you today my angel." she trilled as she gave him his breakfast ."We are going to town, so you will need to look your best." After your bath I will see you in your bedroom to help you get dressed." she went on. A wave of apprehension swept over Tony at this news ."I don't know if I can manage that auntie" he said," I've never been out as a girl before." "Don't worry my sweetheart" said Aunt Sybil, squeezing his hand reassuringly, "I'll look after you, just leave everything to me. You'll be fine, I promise you." Now completely in awe of his aunt's powers of reason, Tony thought for a moment and decided that if his aunt said it would be o.k. then it must be. "O.k. auntie" he said eventually, "I'll see you upstairs." "Good girl." said Aunt Sybil.
Tony lay in the bath contemplating what lay in store for him that day. Having decided that it was best just to have an open mind and wait to see how things would turn out, he slipped out of the bath and dried and dusted himself with talcum powder before putting on his negligee and slippers and making his way to his bedroom ."I'll help you dress today darling" said Aunt Sybil. "We want you to look right for your first adventure out, don't we?"
First she put a wispy peach coloured suspender belt on him and fastened it around his waist. To the suspenders she attached a pair of sheer, flesh coloured stockings with lacy tops, taking care to smooth them up his legs so as to look as snug as possible. Next came his panties, a delightful confection of nylon and lace that perfectly matched his suspender belt. These were followed by a lacy peach bra that when filled with his falsies looked absolutely dreamy on him. Finally a matching slip with a deep lace frill across the bust was pulled over his head and fluttered down prettily to his mid thighs. Tony looked at himself in the mirror and was pleased to see that a realistic looking cleavage had appeared at the top of his petticoat.
Although Tony was now quite competent at putting on his make-up, it was mutually decided that today Aunt Sybil would do it just to make absolutely sure that his look would be beyond question. Sitting himdown in front of the mirror, Aunt Sybil began the process of feminising her nephew's face. Drawing on her considerable well of expertise she beavered away at the task of bringing out his beauty. She was very careful to apply just the right amount of make-up to make him look pretty, but not so much that he would look tarty.
Tony didn't really want this process to end. He loved being made up by his aunt and relished the stirring in his knickers that he always felt when she was close to him.
When she was satisfied with his look, she turned her attention to his outer wear. It was decided that as they were going shopping in town, it was important not to overdress, so between them they chose a pleated tartan skirt and a plain white silk blouse to achieve the affect they wanted. When Tony had the blouse on, Aunt Sybil did up the buttons at the front for him leaving the top two undone so as to expose enough cleavage to look interesting but not enough to make her nephew look common. Next she fitted his skirt which fluttered prettily around his thighs stopping two inches above his knees. A pair of black court shoes with three inch heels completed the ensemble.
Before Tony was allowed to look in the mirror, his aunt reminded him that there were still one or two finishing touches to make, the first being the placement of his wig. A shoulder length straight blonde wig was selected for him and carefully fitted to his head. With his earrings, necklace and charm bracelet in place, and a spritz of perfume from an atomiser Tony was now ready to look in the mirror. What he saw again took his breath away. There looking back at him from the mirror, stood a beautiful teenage girl, exquisitely dressed and looking good enough to eat. Her pretty face was framed by a ravishing head of hair. Her soft breasts moved gently with her breathing. Her peach lingerie could just be made out under her silk blouse. She had a sexy pair of legs that were shown off to full affect by sheer stockings that gave them a tantalising sheen. "She's stunning auntie" whispered Tony in a state of ecstasy ."When can we go out?" "Patience my darling" replied Aunt Sybil." We're almost there" as she produced a black wool jacket from his wardrobe and a black leather shoulder bag for his essentials. Studying her nephew for a few seconds more, Aunt Sybil suddenly had an idea. She reached in to the wardrobe again and pulled out a black beret which she perched on his head giving him a decidedly French image. A black silk scarf with silver flecks added to the frenchness. "Perfect" said Aunt Sybil, and looking in the mirror Tony had to agree. "Now my poppet, you stay here and sort out some things for your handbag while I go and get ready" she said as she left the room.
While Tony busied himself gathering his girly essentials, Aunt Sybil went to her room to get dressed. As usual she was already immaculately dressed so she only needed to change her skirt and blouse. Slipping out of them she cut a stunning figure in her co-ordinated black lingerie. Her voluptuous figure, carefully coiffured hair and expertly applied make-up made her look like a goddess. At least, Tony would have thought so had he been lucky enough to feast his eyes on this magnificent sight. Aunt Sybil slipped in to a black petticoat that matched the rest of her lingerie before putting on a silk blouse in aquamarine and a snug fitting black pencil skirt. She slipped on a pair of four inch stiletto court shoes, a three quarter length camel coat and a silk scarf and she was ready.
Before leaving the house, Aunt Sybil turned to Tony to offer some reassurance. "Now darling you will be completely safe with me while we are out so just relax and enjoy yourself and let me do all the talking. You look lovely, you really do, so let's have a good time shall we?" With these comforting words resounding in his ears, Tony took hold of Aunt Sybil's arm and aunt and niece stepped out in to the big wide world.
As the two "girls" clip clopped along the street, Tony's senses were tingling with excitement. He had a wonderful feeling of freedom that wearing a skirt had given him and he was acutely aware of his lingerie as he walked, something he had never experienced in boys clothes. He was also aware of how his breasts bounced gently up and down as he walked and the click clack of his heels on the pavement could not help but remind him of his femininity.
It was not long before they reached town and the two of them soon found themselves in a large department store. They had a lovely time trying on different fragrances at the perfume counter before moving on to the lingerie department. Aunt Sybil treated Tony to some new stockings and after canvassing his opinion bought some panties for herself. Tony couldn't help wondering what the panties might look like with Aunt Sybil wearing them but he kept that thought to himself.
After a couple of hours browsing the store, aunt and niece decided to have a cup of coffee before moving on. The two of them chatted happily over coffee before Aunt Sybil arose and said "Come on darling, a quick trip to the ladies and then we can go." Before Tony had time to realise what was happening, she had grabbed his hand and was steering the pretty boy toward the powder room. "Now remember your training dear" She whispered in his ear as they entered, so realising he had no choice but to obey his aunt's instruction, Tony walked in to the cubicle as casually as he could and after locking the door, lifted his skirt, pulled down his knickers and sat down to relieve himself. On leaving the cubicle Tony noticed that two other women had entered the powder room so he had to force himself to act as naturally as possible. After washing his hands he checked his make-up in the mirror, patted his hair and looked over to his aunt who gave him a secret wink. As they left she squeezed his hand and whispered "Well done darling."
Tony's confidence was now sky high and he left the department store in a state of near euphoria, eager to find out where his aunt would take him next. He didn't have to wait long. A short walk from the department store was a beauty salon and before he knew it he was standing in the reception area as his aunt conversed with the girl on the counter. "I would like to have my nieces ears pierced please" Aunt Sybil told the girl. "She is on holiday here from France and doesn't speak a word of English so I will have to speak on her behalf." The girl led Tony to a chair and realising what was happening he removed his clip on earrings. She froze his lobes and pierced his ears and even if he had wanted to, Tony was unable to protest. Aunt Sybil chose a dainty pair of gold earrings in the shape of two love hearts and the girl duly fitted them to his ears. As he moved his head from side to side they dangled prettily from his ears and not for the first time Tony gasped at his appearance. A profound change was taking place in Tony's psyche. Tony was fading away and, slowly but surely Susie was replacing him.
Aunt Sybil paid the cashier and the two of them left the salon to begin their walk home. They walked across the park and along several side streets before turning in to the main road that led to Aunt Sybil's house. This route took them past a building site. A fact that Tony became acutely aware of as a chorus of wolf whistles from the builders reached his ears. Even with Aunt Sybil by his side, Tony felt vulnerable as they walked past. Unconsciously he quickened his pace but Aunt Sybil slowed him down again saying "It's o.k. darling, they're only admiring your beauty, you should take it as a compliment". Even though this was a comforting thought, Tony was still eager to get past the builders as he hadn't experienced all this attention before. Unfortunately, just as they were getting away, a gust of wind lifted his skirt and exposed his stocking tops setting off another wave of wolf whistles. Tony wanted to run away but Aunt Sybil held on to his hand and forced him to act in a dignified manner. "A girl must learn to deal with the attentions of admiring men." she reminded him. Realising the sense in what she was saying, Tony calmed down and resumed his previous demeanour.
The rest of the walk was uneventful and the two girls arrived home tired but happy both having had a lovely day. Dinner was a joyous affair that evening as aunt and niece pored over the events of the day, discussing the delights of the lingerie department and chortling with glee at the memory of Tony exposing his stocking tops to all the men on the building site. Tony really enjoyed being a girl now and told his aunt so. What he didn't tell her was that the more he was in her company, the more he felt attracted to her. To Tony, she had become an icon of all that was beautiful and desirable in a woman. He longed to tell her of his feelings but out of shyness he decided to keep them to himself.
Aunt Sybil had a long standing engagement with the local women's circle that evening and told Tony over dinner that she would be out until 10:00pm.,so once more, Tony would have to amuse himself for a few hours. Kissing her niece goodbye, Aunt Sybil stepped out of the front door looking like a million dollars in a smart business suit that consisted of a tight, knee length black pencil skirt and a bolero style jacket with a peplum waist. Under the jacket she wore a white silk blouse with a low cut top. Her usual sheer stockings and high heels perfectly complemented the rest of her outfit. "Be a good girl" she told Tony. "I'll see you when I get back."
To pass the time, Tony decided to do the washing up so slipping on one of his aunt's pinafores and a pair of rubber gloves he busied himself in the kitchen. When the washing up was done he dusted the lounge with a feather duster and plumped up the cushions on the sofa to settle down in front of the TV for the evening. Unfortunately for Tony it was a boring evening for television so after ten minutes of channel hopping he decided to turn it off and go upstairs to try on some of his outfits. Entering his bedroom, Tony took off his skirt and blouse, followed by his petticoat and turned to look at himself in the mirror. He was rather pleased with what he saw. His figure was satisfyingly girlish and in his co-ordinated lingerie and high heels he really did look sexy. It was at this point that curiosity got the better of Tony and against his better judgement he sneaked out of his room and made his way to Aunt Sybil's.
As he pushed open the door, Tony's eyes fell on the department store bag containing Aunt Sybil's panties which were lying on the bed. He had a vague feeling that he shouldn't be doing it but the urge to try them on was overwhelming and by now he was in the grip of a compulsion that was irresistible. Opening the bag Tony feasted his eyes on the heavenly sight of the black satin and lace of which they were made. Before realising it, Tony had slipped off his own knickers and was drawing Aunt Sybil's up his stockinged legs. As they settled in to place Tony felt the delicious thrill of wearing his aunt's panties for the first time. The idea of wearing such an intimate garment belonging to the woman he worshipped sent Tony in to a rapture of delight. As though in a dream, Tony stood outside of himself as he opened his aunt's lingerie drawer and began removing her panties and spreading them out over her bed. He lost all track of time as he tried them on one by one and revelled in the gloriously erotic sensations that coursed through his body. His heart raced as he continued to subsume himself in the delights of his aunt's underwear. Never had he experienced such erotic pleasure and as his excitement rose and rose he became lost in a world of his own.
"TONY!!!!!...........................suddenly Tony was shaken out of his reverie "What's the meaning of this?" said his aunt, standing in the doorway. Tony stood stock still. The meaning was all too obvious. His only remaining male part was proudly protruding from the top of his knickers.(or rather her knickers)
"I…….er………er" stammered Tony as he finally came to his senses ."Why are you wearing my panties?" demanded his aunt as reality came seeping back in to Tony's consciousness. "I want an explanation for this my boy" said his aunt sternly and Tony suddenly realised that she was not referring to him in the feminine any more. "I'm sorry auntie, I got carried away" said the trembling boy. "I didn't realise….""You didn't realise? I'll help you realise" said his aunt. "Bend over my knee" she commanded as she grabbed the boy who was still wearing her panties and forced him over her lap. She raised her hand over his benickered bottom and began to spank him saying........."I"…………smack……….."MUST"…………smack…………"NOT"………….smack………."WEAR"…………smack…………"AUNTIE"………..smack…….."SYBIL'S"………….smack…………"PANTIES"…………smack………WITHOUT"………smack……….."HER"…………smack…………"PERMISSION" "Now what did I say?" she asked Tony. "I must not wear your panties without your permission" answered Tony, his eyes brimming with tears. "That's correct" she said "Now go to your room until I tell you to come out" she said and Tony ran to his room sobbing.
It seemed to Tony that his world had come crashing down around him. Only a few hours before he had been having a wonderful experience, walking around town enjoying his new found femininity with the aunt he adored and now here he was lying on his bed in disgrace with his bottom stinging painfully. How could life be so cruel?
Tony's confidence had been dented now and he lay on the bed in his lingerie feeling sorry for himself and wondering what was in store for a petticoated boy at the mercy of his aunt.
Just as his misery was about to engulf him completely, there was a tap on the door. "Susie" said his aunt softly, "Can I come in?" "Of course auntie" replied Tony, and Aunt Sybil slowly pushed open the door. In came the familiar figure of Aunt Sybil, only this time, instead of her usual attire she was standing in front of Tony in just her lingerie. What she was wearing stunned Tony. Under a see- through negligee she wore a satin and lace bra in burgundy red that made her breasts look even more voluptuous than usual. A matching suspender belt held up a pair of ultra sheer black stockings. Her feet were pressed in to a pair of black fluffy mules. Best of all, she wore a pair of gorgeous French knickers that accentuated her curvy hips to perfection. With her glossy lips and painted nails perfectly matching the colour of her undies she looked like a vision from heaven.
"Are you alright darling?" she enquired as she tiptoed over to Tony's bed ."Well I'm still very upset auntie" said Tony. "I'm really sorry I wore your knickers, I'll never do it again I promise." Aunt Sybil smiled to herself ."Sweetheart" she said lifting his chin with her hand," I don't mind you wearing my panties, it's just the fact that you did it behind my back that upset me." "You mean that if I had asked your permission first it would have been o.k?" asked Tony incredulously. "Of course my darling" replied the vision from heaven. "In fact, to be perfectly honest I feel rather flattered that you like wearing my undies. It shows you find me attractive." "I do, I do." said Tony, flinging his arms around her neck. "You are beautiful" "And so are you my angel" said Aunt Sybil as she pouted her lips and planted an affectionate kiss on his. Tony held on to his aunt and unconsciously opened his mouth slightly, inviting Aunt Sybil to hold her kiss for longer than usual. He almost fainted with delight when she responded in the way he had hoped. Their tongues met, and they both lingered in the moment of their first sexual kiss. Tony felt his aunt's hand move down over his body and sighed inwardly as she slipped it inside his panties and took hold of his only remaining male part. Aunt Sybil manoeuvred Tony on to his back and at the same time unclipped her bra, allowing her magnificent breasts to cascade down in to his face. Although young and naïve, Tony allowed his natural impulses to take over and began sucking contentedly on her erect nipples. With the skill of an expert, Aunt Sybil removed Tony's panties before removing her own and slowly lowered herself down on to his throbbing erection. Niece and aunt both moaned with pleasure as the former slid up and down inside the latter. Their hands roamed freely over each others bodies and their tongues explored new and exciting territories as they lingered in the joy of each other. As the erotic sensations started to become almost unbearable for the two lovers, Aunt Sybil wrapped her stockinged legs around Tony as he turned her on her back and pumped away furiously inside her. No longer able to hold back, he climaxed in to her beautiful body causing them both to groan with ecstasy.
That night, as they snuggled together in their nighties, they both knew that their lives would never be the same again.
To be continued.
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