P.A. for a Daybysusanxdresser©
The gates swung closed behind Charles as he slowly drove his car up the sweeping driveway. Even though he was looking forward to the erotic delights which were in store for him that day, the cares of the world seemed to weigh heavily on his shoulders.
As he drove up to the garage he mused about the dullness of the life which seemed to stretch endlessly before him. Even though he held a senior position at the office, one of the youngest executives ever to reach that level in the firm, he was still not satisfied. He had to put up with the furtive fumblings he attracted in the senior executives' wash room as the old queens tried to regain their long lost youth. The married old queens were the worst. Having long ago subordinated their gay longings to conform with the grey anonymity of corporate respectability, their sex lives were now barren as the sexual desire of the marital bed had long disappeared. Now they returned to their first love and seemed to consider Charles with his youth and effeminate looks, as fair game.
Not that his personal love life, or lack of one, offered much better. A life of trailing night after night through gay bars and bathhouses in the apparently fruitlessly searching for the beautiful young man of his dreams. And night after night returning home alone in disappointment to go to bed with only his masturbatory fantasies for company.
Days such as today seemed to be the only high point of his week. For a few hours he could drop the masculine façade he had to adopt in the office. As Mistress's personal assistant he could luxuriate in his feminine persona, savouring the erotic pleasure of his natural submissiveness by being under Mistress's total control, and fulfilling his desire to please her every whim.
And then there was Nicole. The most lovely, beautiful, gorgeous Nicole. As he parked his car in Mistress's garage and walked round to the front door he could feel the first stirrings of his hardness developing in its silken cocoon at the thought of his weekly dalliance with Nicole.
Without even waiting for him to ring the doorbell, someone inside the house pressed a switch and the door swung open. Charles stepped into the small brightly lit hallway and heard the soft click of the door as it closed behind him. There was no escape now, his life was at Mistress's disposal for the remainder of the day.
Turning to his right he entered the room which Mistress used as her office and stopped just inside the doorway. As usual Mistress was seated in her armchair at the far corner opposite him. A small side table on her left held a tall glass of white wine and a riding crop.
Mistress herself was wearing a long black silk wrap. Her shoulder length black hair was brushed back from her face. A pair of black lycra gloves encasing her hands. From his previous visits, Charles knew that they were probably Mistress's favourite style of evening gloves which reached almost to her shoulders.
Mistress nodded in welcome. At that, Charles laid his document case on the desk beside him and crossed the room to stand before her. Although Mistress sat impassively, he knew she was closely studying him from under those magnificent long black eyelashes.
Apparently satisfied with what she saw, Mistress nodded and Charles removed his jacket, placing it on a hanger and then slipped his feet out off his moccasins. Holding his gaze, Mistress settled lower in her armchair. He removed his tie and undid the top button of his shirt before undoing his belt and letting his pants sink to the floor. Stepping out of the heap of fallen pants he stood before Mistress, his elegant long legs encased in black nylon stockings. Mistress made his wear stockings made from a blend of nylon and lycra as their clinging tightness emphasised the beauty of his legs. She nodded to her right and he crossed over and picked up a pair of red high heels which Mistress had selected for him to wear that day.
Charles slipped the shoes on and after a few teetering steps to get used to the heels, resumed his place before Mistress. As he unbuttoned his shirt he could sense Mistress already stripping him with her gaze. Letting his shirt fall beside his pants he now stood resplendent before Mistress wearing a red padded bra and matching silk panties. The red garters which emerged from his elasticated pantie legs to hold up his stockings, indicated a matching garter belt. Indeed, Mistress had chosen this outfit for him.
For what seemed an eternity he stood before Mistress as she drank in the beauty of his lingerie clad effeminate body. Charles was extremely proud of his physique, his fine bone structure and smooth milky skin, which many sissyboy lovers told him was like touching silk as they caressed him. His natural A cup titties which the sissyboys lovingly fondled before they got down to the serious business of fondling his throbbing erection and until he shot his hot sticky cum into their ever welcoming hand. The height of the heels only serving to further emphasise the elegance of his sculpted calves encased in their tight black stockings. Above all he was immensely proud of his cock which now in its full state of erotic, ecstatic hardness, pressed against his silk panties, displaying his excitement.
Charles was a devoted lover of all things feminine. All his life he had luxuriated in the soft silkiness of lingerie. As a small child he wore Mummy's silky panties under his boy's outer wear, and then as he grew older Mummy bought him his own lingerie, starting with soft silky panties and then gradually extending into slips, bras, stockings and garter belts, until he had a lingerie collection that any real girl would have died for.
He also wore ladies outwear, loving the erotic pleasures of wearing skirts and blouses. The sensation of a silky slip brushing against his stockinged legs as he walked was particularly erotic. With the advent of unisex clothes Charles was in heaven. The masculine cuts of ladies slacks, jackets and blouses allowed him to dress completely in feminine attire without his secret being discovered. His wardrobe now contained no male clothes, even his shoes were purchased from ladies wear shops.
At last Mistress nodded her satisfaction and Charles turned round so she could inspect him from behind. After what seemed another eternity he heard the tap of mistress's riding crop on the table.
As he turned to face Mistress he gasped in surprise at the sight which greeted him. Mistress had opened her wrap to reveal she was wearing all black - bustier, stockings and heels. But what surprise him most of all was what her gloved hands were fondling and caressing between her legs.
From her crotch emerged the most beautiful lifelike dildo Charles had ever seen. He had seen many of Mistress's dildos and on each visit so far his soft butt had experienced the erotic pleasures they provided. But this was something different. As a frequent visitor to gay bath houses and pool parties, his experience of male cock was second to none. But what emerged from Mistress's crotch was far better than any male member he had yet seen.
It was long and straight with pronounced veins, ending in the most exquisitely formed knob. At the other end, nestling against Mistress's crotch, was a soft sac which Charles surmised contained two stones as he preferred to call them. Still locking his eyes with her gaze, Mistress began to rub the dildo in her gloved hands, occasionally moving one hand to fondle the sac at the base of the dildo. From experience Charles knew that the harness holding the dildo in place would also hold another dildo of similar size which would be inside Mistress's pussyhole and a smaller dildo which would be up her butt. As she teased him by masturbating he knew that she was also giving herself vaginal and anal pleasure.
Charles could feel his own cock getting even stiffer in his panties as he watched her. The strong elastic in the waist and legs of his panties held tight against the pressure of his hardness against the silky material and emphasised the form of his exquisite knob. Even showing the little slit in his knob was which anytime now would secrete its precum, making a dark stain where it dampened his panties.
As his excitement intensified he yearned to fondle his knob and hardness through their soft silk cocoon. However, he knew this would incur Mistress's displeasure, perhaps even resulting in being banished from her sissyboy harem. He lived for these weekly sessions with Mistress, luxuriating in being in her total control. He also knew that there were many sissyboys who would love to take his place. Instead, he satisfied his sexual yearnings by alternately clenching and unclenching his butt muscles. That morning he had pressed a maternity size sanitary pad tightly against his pink rosebud, and each time he tightened his muscles, he could feel the pad entering further up inside him. The girlish sensation of the sanitary pad made the pleasure even more erotic.
As she masturbated Mistress's gaze had now moved to focus on his pantied hardness. Charles felt the dampness of his panties against his knob, knowing that the dark patch caused by the precum was exciting Mistress too. Finally Mistress gasped and gave an involuntary jerk. Obviously the dildo in her pussyhole had done its work, bringing her to orgasm.
Mistress rose and took up her riding crop. Leading Charles to the desk she pointed to the intray holding that week's mail. For the rest of the morning he busied himself with Mistress's correspondence. Mistress had already written her comments on the original letters and printed out emails to allow Charles to construct his replies. Many of the letters were to her domina colleagues discussing the merits of their respective sissyboys and offering ideas as to what further training in feminisation their charges required. The emails were mainly to the lingerie boutiques Mistress dealt with, advising the owners about the sissyboys who would be shopping that week and the garments they were to be supplied with. This was how Charles obtained the lingerie set he was currently wearing, and his cock hardened in his panties as he typed the instructions. He just yearned to see these sissyboys in the lingerie Mistress was ordering for them.
Most of this time Mistress sat in her armchair sipping her glass of wine, fondling her dildo, and gazing longingly at Charles through those long eyelashes. Occasionally she would walk over to the desk and look over his shoulder at the screen, the dildo swaying proudly before her, and the loose robe flowing behind in response to her movements. Usually she would nod in approval at what Charles had written but sometimes she would tap at a word or phrase on the screen to indicate that it was to be changed.
As on previous visits Mistress never spoke, preferring to gesture with her riding crop to communicate her instructions. As Mistress stood behind him she would gently caress his back with the tip of the riding crop. Charles's soft girlish skin tingled with erotic pleasure at the touch. She would then move in such a way that her robe brushed against his skin which was even more erotic. This time, however, she also stood alongside him with one foot placed on a small stool so she could display the dildo in its full majestic hardness.
Mistress knew how to tease. She stood so close that Charles could feel the sensation of her dildo on his skin. As Mistress read the responses on the screen she fondled the dildo with one hand, while with the other she ran the tip of her riding crop around his neck and shoulders. When she reached under his chin she used the riding crop to gently guide his head until he was looking up at her. Still fondling her dildo she smiled down on him. The knob of the dildo was so close to his face that he could almost kiss it.
The thought of being asked to give Mistress a blow job flashed through his mind. Instead, Mistress took his hand in her gloved hand and laid it on the shaft of the dildo. Lost in erotic ecstasy Charles fondled the latex shaft and knob. It felt warm and springy to his touch. His hand then moved to the sac, holding it the palm of his cupped hand as he loved to do with sissyboys. As his trembling fingers closed round the sac he could feel the two ovoid stones it contained. Rubbing the stones between his fingers, Charles could feel the throbbing hardness of own cock in his panties.
At last Mistress's correspondence was finished. The letters had been written and the emails had been sent. Now he wondered, how would Mistress rate his performance today. He always tried to do his best and to date Mistress had always been satisfied, even boasting to her domina colleagues of his prowess.
A bell rang. Charles looked up at Mistress who nodded. He rose from the desk and went out into the hallway and down the corridor to a small pantry. Here he found Nicole arranging a tray with coffee cups and sandwiches. Today Nicole was dressed in a short black silky French maid's uniform with white trim. Her legs were encased in black fishnet stockings and she had black moccasins on her feet. But what excited Charles most was the way she had done her hair that morning. Her long light straw coloured hair was tightly drawn back into a ponytail and held in place with a black silk ribbon. The tightness emphasised the beauty of her facial bone structure contained in her soft milky white skin.
As he entered the pantry Nicole gazed admiringly at his proudly erect cock straining at his panties. Leaning over to gently kiss his cheek, she allowed the back of her hand to gently caress his silken encased hardness.
"We are an excited sissyboy today, aren't we?" she cooed into his ear.
Charles was so engrossed in her erotic loveliness that he could only gasp, "You always excite me you gorgeously, beautiful girl".
The kissed some more. At last he recovered sufficiently to ask, "What panties are you wearing today?"
"Thought you would never ask. You're such a naughty sissyboy to keep a girl waiting in suspense like that."
Taking a few steps back Nicole shyly lifted the hem of her dress to reveal her white silky panties. Charles gazed in rapture at the sight which met his eyes. Nicole was wearing the full brief style of panties which she favoured, and a matching white garter belt held up her stockings. But it was what was inside these panties that most excited him. Pressing against the silk panties was the most magnificent hardness, the tightness of the elastic in the legs of her panties preventing it escaping. Charles gave her an appealing look to which she nodded in reply.
Standing in front of her Charles tenderly fondled her warm throbbing hardness, gently squeezing it in the way he knew she loved. His hand fondled the length of her shaft until he reached her knob. She gasped with erotic pleasure as he gently caressed the hot knob through its pantied silkiness and soon he could feel the hot sticky dampness of Nicole's precum. In response Nicole leaned over to kiss Charles' lips and gently fondled his own pantied balls and cock.
Nicole was actually the most beautiful young man. Like Charles she was a sissyboy, but whereas Charles had the androgynous looks with which he could pass as a boy or a girl with equal ease, Nicole's natural feminine looks, smooth milky skin, and slim willowy body gave her a more feminine appearance than many real girls. Her natural sissyboy titties adequately filled an A cup. Standing au naturel with her cock pulled back between her legs she looked every inch a girl. Lesbians often fussed over her and told her that she was more feminine than may a real girl. Mistress loved effeminate submissive sissyboys and, having fallen in love with Nicole's girlishness on their first encounter, gave her a position as her personal maid.
Even when Nicole was at school she lived in her feminine persona at every opportunity. Mummy had called her "my darling little girl" and had indulged her feminine desires. After leaving school she had lived almost full time as a girl only adopting her male persona when attending gay venues where her cock and butt were always welcome. Even when she attended gay parties as a girl the other sissyboys couldn't keep their hands off her cock and she often ended up in bed with several of the guests.
And what a cock she had. Charles thought he was well hung compared to other sissyboys but Nicole's was even longer by over an inch. They had often compared cocks and agreed that it was being completely smooth that made their cocks appear longer than many hairy cocks.
For what seemed hours the two sissyboys were lost in the erotic rapture of their love, fondling and kissing until they felt the dampness of each other's pre cum through their panties.
Finally Nicole said,
"Has Mistress showed you her new toy yet?"
"Yes. It's gorgeously lifelike. It fact it's better than a lot of real cocks I've seen and fondled. But somehow it looks familiar. When did she get it."
"It only arrived yesterday morning. I was with her when it arrived and she let me fondle it.
"No naughty boy, she didn't. She wore for the first time today especially for your erotic delight."
She leaned over and said in a conspiratorial whisper, "It should be familiar to you. It's a latex model of Rocky Hardman's cock. He had it modelled for a limited edition and Mistress got it through one of her girlfriends."
Rocky Hardman's cock! So that was why it was so familiar. Rocky Hardman was every sissyboy's masturbatory inspiration and delight. His full frontal photographs showing his majestic cock regularly appeared in gay magazines and calendars, and he was the star of many gay movies. Charles was an avid collector of gay iconography and had many of Rocky Hardman's photographs in his collection, to which he often masturbated. And to think he had just fondled a latex replica of Rocky Hardman's cock. Wouldn't the other sissyboys be green with envy when he told them. He could imagine a whole new repertoire of masturbatory fantasies opening up.
"You had better go before the coffee cools, and Mistress will really be upset with you", Nicole broke into his reverie.
Charles carried the tray back to Mistress's room and placed it on a small table. As she sat down Mistress gestured for him to sit alongside her. Charles poured their coffee and offered her the plate of sandwiches. They ate lunch in silence. After a few minutes he gradually felt a sensation against his thigh. It was Mistress rubbing her stockinged thigh against his. The sensation moved down to his calf and then he felt Mistress's shoe nudging his. Mistress was playing footsy with him!
One of Mistress gloved hand disappeared under the table and soon Charles could feel the palm of her hand caressing his stockinged knee. Knowing the eventual destination of Mistress's hand he opened his legs to allow her free access The hand gradually moved in a circular motion caressing along his thigh until Mistress reached her target. The back of her hand brushed the hardness of his pantied cock and then her fingers massaged his knob. The hand gradually worked its way down his shaft to his crotch and he winced as Mistress gently squeezed his stones.
As her hand played with his stones, Charles could feel her middle finger prodding the thickness of his sanitary pad where it entered his pink rosebud. Mistress required all her sissboys to wear thick sanitary pads in their panties at all times, considering that it was an essential part of their feminisation. Like Nicole, Charles had been a regular user of sanitary pads long before he was introduced to Mistress, so his feminisation was already well advanced when he fell under her control.
Mistress dropped her other hand under the table and from the ecstatic look on her face he realised that she was masturbating herself as she fondled his cock and stones. Several times he thought she was going to let him cum. But just as he felt the juice rising up his shaft, she squeezed his knob to prevent the cum exploding into his panties.