charlie boy,charlie girl (part 1)

charlie's angel

Charlie had a desire. Charlie had a dream. His daily life was getting to him. Long days at the office, a less than stellar sex life a home was bringing him down. He always knew he was different, even special. In his line of work, he had to be dominant, he had to call the shots. Charlie was a partner in a big lawfirm. Responsibilities were sometimes overwhelming.

Being five foot seven, a dark haired brunette with blue eyes made him something of a 'pretty boy'. He did his best to act the part of an A-typical alpha male, but it felt wrong, all wrong. He did not lack for money, beautiful women, fast cars or nice vacations, or even a few nice homes. The problem, for Charlie, was that in his mind, coveted women, lusted to be like them. When he was intimate with them, he secretly pretended it was him being penetrated by a male. He imagined constantly what it would be like, to be them. His mind often wondered what it was like to feel a long, thick hard cock pulsing and throbbing inside him. No, Charlie did not consider himself homosexual, because he did not see himself as a man.

Socially, he applied himself to a man's world, constrained to the rules and regulations, dictates and obligations he knew where what he was supposed to do. That did not mean he had to be happy about it. His bread and butter was his workplace, he feared being poor and destitute, if anyone found out his secret desires. Charlie played a good game, he had to. He finally paid off his student loans, drove a high-end sports car. financially,life was good. Good, but not enough. He often perused wigs and dress websites on his smart phone in his spare time. He daydreamed what he would look like as a female. When he was aroused to the point he could no longer take it, he would masturbate, feeling unfulfilled after the fact. Even when he was being intimate with a woman, the only way he could cum, was to pretend he was them. Sometimes he thought he was broken, sometimes he didn't care.

One day, one of his clients came to see him. A very attractive female. Charlie, in his usual manner was graceful and pleasant in his greetings. His eyes subcontiously scanned her from head to toe, taking in her femininity. She was a relitively new client, and had only been in the office once or twice before. Her shoulder length blonde hair had a slight natural curve to it.Full bodied, with a bounce to it. her radiant green eyes sparkled like emeralds. When she smiled, her perfectly aligned teeth,white and radiant, reminded him of toothpaste commercials, they were that perfect.. She had all the right curves in all the right places. Charlie's mind drooled and lusted to be her.

She smiled faintly as Charlie motioned her to sit down in the leather chair in front of his desk. she did so, crossing her legs, tanned and smooth,soft and silky. Charlie was glad he seated himself, so he could hide his growing erection. He was both embarrased and upset at the same time,that his desires interupted his professionalism. He was human after all, its bound to happen sometime, right? He cleared his mind of impure thought and focused on his client's need.
"Mrs. Grendle? Is that correct?" he queried calmly
"Yes,thas me, Tabitha Grendle" She replied with what sounded like a slight sweedish accent. Charlie felt his hardon turn to granite, straining against his dress pants. He always thought accents were erotic, especially European accents.
"How can we help you today?" he asked her.
"I...have..problem.." She replied,searching for the right words in english.
"Well, let's see if we can help you out of it then," he tried to sound both consoling and sophistocated at the same time.
She was quiet and comtemplative, almost sheepish. She suddenly blushed as she removed some papers from her loius vitton handbag. she silently handed them over for Charlie to examine. As he read them a puzzling look crossed his face. He looked up at Tabitha, then down at the papers,then back to her.
"Oh...i...see" he stammered gracelessly. if his boner was any harder, he would have drilled through the desktop. Tabitha blushed profusely and hid her face in her hands,sobbing softly.
"There,there" Charlie said,half rising to console her,while stil hiding his aching stiffy.
"We...We can deal with this" he continued," Leave this to me, i will deal with it personally."
"You...you will fix?" She asked, her mood brightening significantly. Those emerald eyes sparkling again.
"Most certainly." Charlie declared. what the rest of the world did not know, and neither did he until just now, was that Tabitha was not completely female. She was born a male, but her family wanted a daughter, and raised her as female. At a very early age, she was administered hormone replacement therapy. Charlie would have never guessed she was ever a male.
"If i have any further questions, i will contact you, ok?" He asked in a calming manner.
"ok. thank you,thank you." she said, kissing him softly on the cheek, grabbing her handbag, and wiggle-assed out of his office. Charlie's mind drooled even more now.
his sexual horizons just widened. he poured over the papers she had handed him again. Birth cirtificate, copy of drivers licence, will from her now-deceased husband,marriage license.............his mind started wandering...trying to remember her sitting in front of him, conjuring up the mental image of her..but naked...he could feel the subsiding hardon returning. her 'manhood' must be small and useles after all the hormones..

Later on that evening, his attentions were turned to websearches and terms used for women with penises...funtanari, shemale,hermaphrodite, sissy........sissy....the word called to him hypnotically..most of the words he found led to one porn site or another. the thought of being a sissy intrigued him. In his mind he knew he would probably never get a sex reassigment surgery, even though he could afford it. His sexual proclivities just evolved from cross dressing to being a sissy. He felt the desire bloom like a rose in the hot July sun. Hours passed as his research continued...forced feminization...sissy...echoing inside his head.He felt weird, he felt giddy..like a...schoolgirl? Isn't that how the saying goes? a wave of tingles washed over his whole body as he viewed image after image of beautiful sissies all dressed up, in various comprimising poses. Some of them were by themselves, some were doggy style, a dominant male penetrating them. The sissies' all dripping a clear fluid almost syrup like in consistancy , from their small and useless genitals. Charlie felt a pulse in his penis as he automatically ejaculated some pre-cum, much like the lovlies he was looking at.
He expanded his search to include videos, hearing their feminine voices moaning as they were being sexed by the well-hung males, was too much for Charlie to bear. He had to masturbate, he had to masturbate..now. No sooner did he remove his manhood from his underwear, his shaft began to throb,pulse and go soft..he struggled to make it hard again but found it difficult. After several minutes of struggling, he managed to get it semihard enough to dribble out some cum in a weak ejaculation. His anal orifice began twitching, opening and closing,spasming....'oh God', he thought "am i..a..sissy?" his groin pulsed in response, as if confirming it...
(to be continued)