Auntie's Soiree Sissy
Gordon Woollenfall felt palpitations hammering beneath his white shirt and tie as his mother fussed his shoulder length hair into perfect neatness. "Make a big effort, Gordon, and smile at Auntie Mabel when she speaks to you. You are to listen to everything she says with wrapt attention, and sit up straight with your hands together in your lap."
The elevator stopped at the seventh floor and the doors opened silently onto a marble hallway. "Let Auntie kiss you, Gordon, and above all," whispered his mother, propelling her son and his wheeled suitcase towards the oak door of the penthouse, "you must do whatever she asks, understand?"
"Yes, mama." Gordon couldn't remember his aunt, but he had a picture of cosmetic surgery and expensive couture. When the door opened and the maid was thrust to one side, he could adjust his view of her from the real thing.
"Amanda... my da-a-a-ahling! How fabulous to see you after all these years. You haven't lost your dimple, honey, and your hair! Ohhh, how exquisite!" Great Aunt Mabel was a lot older than his mother, with platinum hair in a cloud like shape, more lipstick than he had ever seen on one woman, and a fortune in strings of pearls. As Aunt Mabel hugged, her face was planted so far over her niece's shoulder that she could take in her son in a single glance of lust.
"Diamonds and pearls!" she exclaimed, "so this... is Gordon."
She dislocated herself from the boy's mother so that she could descend fully onto the eighteen-year-old in his neat, white shirt and grey trousers. Her hands cupped his chin as if to lift him from the carpet. "What a peach! A blossom! Amanda, sweetheart, he will do nicely... I mean... he will be a credit to you while you are away."
Gordon spent the next half an hour sitting in the middle of one settee, his hands in his lap, while his mother and Great Aunt Mabel sat on the other and viewed him as they caught up on family history and discussed to his mother's three-month business trip in China. All too soon, his mother was wrapping him in a final embrace, and he was left alone with his aunt.
His suitcase disappeared, and the youth was shown to his bedroom, where his personal maid had laid out a fresh shirt and shorts. He was soon to find that all his new shirts were sweetly decorated with lace or dainty frills, and many of them were short sleeved, with soft little puffs at the shoulders. Some of them buttoned down his back, for his maid to fasten up.
He wished he could find his suitcase. It had his underwear, which he would rather have worn than the little silk panties he was put into.
Great Aunt Mabel took the earliest opportunity to get her hands on her nephew. "Gordon, my precious, come and sit beside me while I tell you some wonderfully good news."
The youth would have loved to shield his nose from the wreaths of perfume that filled it, but both his hands were held in the lap of his aunt.
"You look terribly sweet this evening, precious," she said, her beauty spots moving towards her jeweled earrings as she smiled, "which is very important to your Auntie Mabel, because I want you to be a success for me, the way your dear mother would want it. You do want to please your dear mama, don't you darling?"
Gordon had to take a scented breath in order to speak. "Yes, Auntie". His shirt had already been changed three times since his mother had gone two or three hours before, and the one he was in at the moment was in a soft, cream silk embroidered with little flowers and it... buttoned across the girls' way. His very short shorts were elasticated into a little frill at the top of each leg.
"I have kept my special news until now, darling, so that, if you want to weep a few little tears of joy, Auntie Mabel is here to give you my deepest and most loving cuddles." She cupped Gordon's chin in a spread of nail-varnished fingers, and held his gaze with her deep hazel eyes. "You are to be my personal assistant and cherub when I hold my soirees in the drawing room." Her lips, already very thick and gleaming with crimson lipstick, seemed to quiver and slacken with emotions as she let her information sink into her nephew's small male brain. "And since my guests will all be ladies who love to surround themselves with feminine beauty, I will of course need to dress you in suitably soft and delicate feminine fashions." Her lips spread into the widest smile yet as she clicked her fingers for the maid to approach. "This means that we must start with girls' lingerie."
Gordon thought he had died of a heart attack. He certainly couldn't remember what happened next, and only began to realise where he was when the cool air of the sitting room told him that he was quite naked and half-lying, half-sitting across Aunt Mabel's lap, sinking into the magenta taffeta of her evening gown. He wasn't quite naked: his legs were in women's nylons, pulled tight to his waist with garters of ruched elastic. His small penis was stretched into an ache of erect sweetness as he realised that his chest was dressed in the two pretty mounds of a lilac satin brassiere.
"Pass me the silk pantalettes, Corinne," he heard from above his hair. "I shall hold them over his nose while you slip him into his pretty little blouse."
The next thing Gordon knew, he was floating into a dream of soft silk and girlie lace, heavy with a delicious perfume that made his whole body want to become feminine. The liquid caress of soft silk slipped up his arms and clustered round his shoulders and neck, and his blouse gave him a powerful feminine feeling in his eager penis. He found the pantalettes slithering up his face, then spreading over his hair, until they descended over his head, enveloping his hair and face in their cream silk feminine prettiness. The heavenly pantaletts ensured that the sweetness of the satin bloomers gave him an overwhelming desire to be more feminine as they were slithered up his stockings, until his precious places were snugly encased in their delicious coolness. More cool satin followed, in the form of satin lined shorts threaded over his feet and slid exquisitely up his legs, nestling over his bloomers, and fastening in buttons down each of his hips. Ohhh the pleasure as slender feminine fingers delivered his stiffened member from a frilled opening in his bloomers and another in his shorts, so that it stood upright above his Aunt's lap in the cool, soft air of the sitting room. Now the excited member was being dressed itself by Corrine's expert fingers, and buttoned tightly up its front in the smoothest of glossy pink satin lined with white silk. His penis reached higher, and filled its penis dress tightly, swelling it with blissful stiffness.
"Put his hair into ringlets, Corinne," he heard as the silk pantalettes were slid off his head, "and touch his darling features with the nicest of girlish blushes and shades. My, how the ladies are going to love him this evening."
To Gordon, it was an overwhelming experience, this blushing sweetness inside his bloomers and... the satin lined shorts in sable velvet that he found himself wearing. He wore a little gilet to match, and a bow of satin lined velvet was fastened into his hair as long feminine ringlets dangled and bounced around his blushing cheeks.
"I know you will melt softly into the maternal embrace of each of my friends, Gordon, my honeypot. When ladies hug you to their bosoms, pet, be sure to turn that heavenly pink lipstick of yours towards the lips of the lady who holds you. She will want to kiss you and kiss you, my precious. And when her eager fingers seek out that darling satin clitty dress, you may push and push your little stiffness into the palm of her glove. That way, each lady will want to hold you again and again and again. Won't that be lovely, sweetheart?"
"Y-Yes, Auntie Mabel." Gordon gasped, too overwhelmed by his newly discovered femininity to form a clear picture of what his aunt had in mind. He had to wait until after dinner to get the 'first hand' experience as it were. He sat on his satin covered stool in the middle of the circle of elegant, smartly dressed ladies, to be admired, complimented and invited to sit on one soft, silk or acetate lap after another. He soon discovered that his satin clitty dress was the centre of attention for the ladies, and that it could become even tighter than he could have ever imagined, each of the ladies squealing with pleasure as she brought him off.
The peeny dress was easily unbuttoned when it became squidgy with ejaculated jism, and replaced with another pretty dress, in silk, satin or chiffon, for the ladies to fondle with all the enthusiasm of their bottomless, lustful desires. And as Gordon's mama had declared, above all, he was to do as Great Aunt Mabel said, so his lips turned upwards for kiss after sensuous kiss, while his penis thrust appreciatively into the palm of each lady's kid or satin glove. Aunt Mabel was very pleased, knowing that, unlike her guests who came and went, she could play with her youthful nephew tonight and every night as he wriggled in her bed dressed in more silk lingerie and a pretty babydoll nightie.