tagTransgender & CrossdressersThe Intimate Escort

The Intimate Escort


Jillian Graham stepped from her shower, pulled off her shower cap and rubbed peach scented lotion over her wet body from her feet to her neck. Then she took a towel and wiped the condensation off of her full-length mirror and surveyed herself. She took in her dark brown skin; her tall, lean frame and long, sexy legs; her tight, round buttocks and flat stomach; and her soft, ripe breasts. She turned to the side and marveled at how her taut ass jutted out - a terrific little bubble-butt. She turned again and checked out the rear view over her shoulder. Her back was smooth and narrowed to a tiny waist that flared into that round ass and sexy thighs which led to perfect calves - with just a hint of coiled muscle from her constant workouts - before tapering to slim, shapely ankles.

She completed her circle by turning back to face herself again. She cupped her breasts in her hands. They were soft and natural with dark aureoles and nipples, a perfect C-cup. She ran her fingers over her dark nipples before pinching and rolling them between her thumbs and forefingers until they grew hard. She closed her eyes and pulled her taut nipples, luxuriating in her pleasure. On impulse she squirted a generous portion of the peach lotion into her hands and rubbed it between her ass-cheeks. The lotion felt cool and slick as she smoothed it over her anus. Then she slowly inserted her middle finger into her rosebud. She had taken an enema before her shower and was completely clean. Her middle finger felt so good that she soon added a second finger, pleased with how tightly her anal ring held her fingers inside. She slowly slid her fingers in and out, brushing them against her special spot, pleasing herself. Better save it for the client, she thought and reluctantly removed her fingers.

She opened her eyes and looked between her thighs and saw the evidence that put to lie to her womanly perfection. Nestled between her thighs was her prick, which - even in her aroused state - was very, very small. It was no more than two inches long and her tiny balls – shriveled and shrunken by years of female hormone therapy – were the size of grapes. She knew that the removal of her genitals would be the final step in her transformation to complete womanhood but she felt ambivalent about her clitty - as she referred to it – but many of her clients loved it. Despite her genitals small size, they still gave her pleasure and she was reluctant to make any changes just yet. She had the money to pay for the operation but she couldn't bring herself to that final commitment. Maybe if she ever found the right man to settle down with, and he wanted her to have a vagina, she would schedule the surgery. In the meantime, she enjoyed her life as a beautiful, highly paid transsexual escort to the fullest, feeling that she had the best of all possible worlds.

She went into her bedroom to complete her preparations for the evening. She painted her finger and toe nails a red so dark it was almost burgundy in color. When the polish was dry, she put a dab of expensive French perfume behind each ear and just above her magnificent cleavage. Next she put on lipstick that matched her nail polish. Finally, she sat in front of her lighted mirror and applied a bit of coppery eye shadow to accentuate her eyes. She surveyed her face and was pleased. She had an oval shaped face with full, sensuous lips; a slightly up-turned pug nose; gorgeous high cheekbones; and deep, chocolate-brown eyes with naturally long lashes. Her hair - cut in a bob for the summer - was soft and straight. She kept her hair a rich copper color that complemented and accented her dark complexion. Jillian was naturally beautiful and didn't need to gild the lily, so her philosophy towards makeup was "less is more." Jillian smiled at her reflection and arose to dress for her client.

Jillian and her client had first corresponded through e-mails. Later, they had had long telephone conversations to get to know each other and to plan their date so she knew how her client wanted her to dress. She put on a garter belt and dark stockings. Next came a pair of French-cut panties and a thin bra, which held her perfect tits aloft and allowed her nipples to show. A delicate slip finished off her lingerie. She assayed her visage and was pleased with the ensemble. Everything except her stockings was silk and a dusky rose-red that was extremely sexy. She twirled and smiled with delight as the shimmering slip swayed and danced on her flawless figure. Finally, she slipped into a low-cut black mini-dress and black shoes with five-inch high stiletto heels that emphasized her excellent legs. The dress had thin shoulder straps and a fine mesh design above the bodice that drew the eye to her splendid cleavage; the waist was narrow and the skirt was slit to give a glimpse of thigh when she moved or sat. Jillian appraised her image a final time and was extremely pleased with the figure she cut. She grabbed her keys and a black leather clutch-purse and headed out for her date.

She drove to the Ritz-Carleton Hotel and was seated at a cozy, romantic corner table in their most opulent restaurant ten minutes early for her date. She ordered a glass of cranberry juice – she rarely drank alcohol when on business – and waited, facing the entrance, for her client to show up. At precisely five minutes before their meeting time her client, Patrick Morrison, spoke to the hostess and was led to their table. As he approached, Jillian noted that Patrick looked exactly like the pictures he had e-mailed her. So many of her clients played games, or were ashamed of booking an escort, and sent other people's pictures. When it came to looks, Patrick had nothing to be ashamed of - he was a good-looking white guy in his mid-forties who was tall and athletic without being bulky. He moved with an effortless, masculine grace that bespoke his background as a basketball and tennis player. His features were keen and handsome, topped with penetrating blue eyes and well-styled salt and pepper hair. He wore an impeccably tailored charcoal gray suit; an immaculate pale gray shirt with silver and onyx cufflinks; a luxuriant silk tie with indigo, silver and black stripes; black socks and hand-made black leather loafers. He oozed confidence, power and wealth.

As he was led to their table, Patrick was also assessing Jillian. God, he thought, she's everything I want. She was beautiful, classy, feminine and sultry in a Continental manner. He thought of her as a very exotic and wondrous creature and she fascinated him. Patrick had secretly been intrigued by she-males for years. Until now, he had never acted on his desires. He had gone through a messy divorce six months earlier and was forced to examine who he was and how he lived. He had come to the conclusion that it was time to explore and expand his sexual identity. He felt that he had to concentrate on what pleased him and not to conform to what was expected of him. Now he was ready to cut loose sexually and experiment a little. He visited many transsexual websites and perused nearly a hundred professional escorts in his city before selecting Jillian for his first encounter. He wanted his first encounter to be with a drop-dead gorgeous she-male. He wasn't interested in someone who was "fully functional." He wasn't interested in a transsexual dominatrix – although Jillian could perform that role when requested to do so. Jillian was just what he wanted, completely feminine and far more than just "passable."

"Good evening, Patrick," Jillian said, rising, smiling and extending her hand when he reached their table.

He took her hand gently in his, bowed and kissed the back of it lightly.

"Good evening, Jillian," he said straightening up and holding her hand in both of his. "I must say, you are so radiantly beautiful that I am the luckiest man on earth to be your companion for the evening."

Jillian was momentarily overcome. Usually clients complimented her but weren't nearly as eloquent or sincere in their praise.

"Thank, you, Patrick," she said, softly squeezing his hand and smiling into his eyes. "I feel exactly the same way. I can't imagine having a more handsome or elegant date."

"Thank you, Jillian, every word is true."

They sat and the hostess took Patrick's drink order and gracefully departed.

"Well, I guess we should get the business aspect of this out of the way first," Patrick said, taking and envelope and a folded piece of paper out of his suit pocket and sliding them across the table to Jillian.

She checked the unsealed envelope first. It held her fee and a very generous tip, which she thanked him for. Next, she opened and read the folded piece of paper, which was Patrick's negative HIV/AIDS test result from earlier in the day. She slid both items into her purse and took out and passed her test results to him, which he read and passed back to her. That out of the way, they relaxed and made small talk until the waiter brought their drinks, her juice and a vodka martini for him. They sipped their drinks and continued chatting as they perused the menu. They ordered oysters on the half-shell for him and salmon sushi for her as appetizers; garlic and rosemary encrusted lamb chops with asparagus and pilaf for his entrée and grilled red snapper with sweet potato soufflé and wilted baby spinach and leeks for her. Then Patrick paused and looked her in the eye.

"Jillian, tonight is very special for me," he said. "I know you have rules about drinking with clients but I was wondering if you would share a bottle of champagne with me?"

She considered very carefully and then answered.

"Certainly, Patrick, some bubbly would be very nice."

"Excellent," he said passing their menus to the waiter. "We'll have a bottle of the rosè Perrier Jouet, the 2005 vintage."

"Wonderful choice, sir, I'll bring it right out," the waiter said as he glided away.

"You certainly know how to spoil a girl, Patrick," Jillian said.

"Thank you, it's the least I can do. After all, you're about to help me live out a long-time fantasy and satisfy my curiosity about something I've wondered about for quite a while."

"Ah, yes, your fantasy. You've told me the details of what you want to do but you've never said why you want to make love to a girl like me."

"To be honest, I don't know why," Patrick answered, blushing slightly. "I'm not gay and, as I told you, I'm not really interested in being with someone like you who has a functioning penis. What I do know is that I've always wondered what it would be like to be with someone like you. Maybe it's a male thing. Maybe I want to conquer a weaker, feminine male. I really haven't pondered the why and wherefore but I do know I'm turned on by the thought of being with you and pleasing you."

"Well, a straight man wanting to be with a transsexual is not unusual," Jillian said, "but most such men are very interested in functioning equipment. Most, in fact, want to either suck a cock or be fucked by a cock or both. But they desire the chance to experience a penis that's attached to a feminine form rather than a masculine form. I believe they rationalize that by doing it with a she-male they aren't really 'doing it with another man,' therefore minimizing their level of discomfort. Eliminating the traditional ideas and images of masculinity from the equation allows them to avoid facing up to either the feminine or gay aspect of their personality."

"Yes," Patrick said quietly, "I can see that. Society's strict gender codes prohibit acting on what very well may be perfectly natural desires. I think, in my case, it's a fascination with exotic beauty. I'm much more fascinated by your femininity and loveliness than your gender. I don't mean to brag, but I've had my fair share of female lovers over the years - and I've had anal sex with a few of them - but I'm enthralled by the thought of making love with you, of driving you wild and then fucking you. Why is that? Why does the idea turn me on so? I don't know. But I do know it's precisely what I want to do. You're extremely beautiful and I want to possess you."

"Thank you for the compliment and your honesty. Who knows why we do some of the things we do sexually? The key to good sex is to free ourselves, to express ourselves completely. It's always good to spice up our sex lives and keep things interesting and fresh for ourselves. Maybe you're turned on by the whole concept of 'the other who is similar.' It could be that you see me as feminine and passive, and 'conquering' someone like that turns you on. Hell, maybe you're tired of pussy and just want something different. But, whatever the reason, here we are. I promise to make your first time with a t-girl very, very special and memorable."

"Thank you, Jillian, I appreciate both your professional insight and candor."

The waiter returned and poured their champagne. They toasted and drank. From that point on the conversation was light and playful. They both flirted and laughed and enjoyed each other's company and a fine meal. At the end, they shared and lingered over a dessert of chocolate covered strawberries topped with whipped cream flavored with hazelnut liqueur. While Patrick paid the bill, Jillian slipped away to the lady's room and called her bodyguard.

Her bodyguard was seated a few tables away from her and Patrick. He answered his cell on the first ring.

"Hello," Jillian said. "We will be in room 713. I will slip away and call you in two hours. If you don't hear from me knock on the door and pretend you have the wrong room number. If I don't answer the door or you can't see me, then something will be wrong and you will know what to do."

"Yes, ma'am," was the bodyguard's reply. He was a tall muscular man in his early thirties. He had served in the Israeli military and was very well trained. He was also trustworthy and very discreet, which is why Jillian used him with almost every client.

She returned to the table and Patrick had paid the bill. He took her hand and led her through the lobby to the elevators. Once the doors closed, and they were alone and out of other people's sight, Patrick took Jillian into his arms and gently kissed her lips. She slipped her tongue past his lips and kissed him back deeply. Their first kiss was not only highly erotic, it was intimate, which was why Jillian vetted her clients and went through such a lengthy interview process with all of them. Jillian offered not just sex but intimacy to each of her clients. It was something that 99% of sex professionals couldn't or didn't do. It made her unique and allowed her to charge select clients a thousand dollars per session. Jillian knew that people, especially men, yearned for sex but they hungered for intimacy even more.

Patrick was holding her securely in his arms and returning her kiss with equal passion when the bell rang and doors opened on his floor. They broke apart and walked to his suite with his hand on her splendid bottom and hers around his waist. He unlocked the door and stepped back to allow her to enter first. She had been in many such rooms so she wasn't impressed by the view or the décor and she headed straight for the bedroom. He closed and locked the door and followed her.

Once in the bedroom, he took her into his arms and they kissed again. He delighted in her soft, warm body pressing against him. He caught the scent of her exquisite perfume as he bent forward and traced kisses along her throat. His lips traveled down to her cleavage as his hands slid from her back to fondle her ample ass. God, he thought, her ass is a wonder. It's so tight and shapely, so firm and inviting. He slipped her dress straps off her shoulders, unzipped it and it fell to the floor. She stepped out of the dress and her shoes. He unclasped her bra down allowing him access to her breasts, which he attacked hungrily. He concentrated on experiencing his senses to the fullest. He delighted in the warmth of her smooth, soft flesh in his hands, the exquisite scent of her perfume in his nostrils and the delightful way her nipples grew hard in his mouth and on his tongue. He alternated licking and sucking her pert buds, then gently biting them before pulling them with his teeth.

Jillian was enjoying the pleasure of Patrick worshipping her body but she was also firmly in control and aware of everything around her. She decided that now was the time to subtly takeover and to direct him. She stepped away from him, moved behind him and slid his jacket off and hung it neatly on a chair. Then she took off his tie, shirt and undershirt and dropped them on the floor. Patrick stepped out of his shoes and quickly bent and pulled his socks off. He stood before her in his boxer shorts with his hardon straining against the fabric. Jillian ran her hands over his nipples then she pinched and pulled his nipples firmly. He moaned and she leaned forward and licked first one nipple then the other before biting them hard. She stepped back and coolly surveyed him. He stood with a loopy grin on his face and a very obvious hardon struggling against his underpants. She stepped to him, looked into his eyes, pulled his face down and kissed him fiercely. She broke off their kiss and pushed him onto the bed before jumping on top of him.

She lie on top of him, kissing him roughly and running her hands over his rangy arms and muscular chest as he caressed her thighs and ass and back before concentrating on her breasts. Jillian slid her hands over his hard cock through his underpants, happy at the feel of its length and thickness. She rolled over and he came to rest on top of her. He kissed her mouth; her throat; and down the deep crevice of her cleavage down to her nipples again. He clasped her breasts and sucked her nipples fiercely before licking his way down to her thighs. He paused to undo her stockings and pull them and her garter belt off. Next he kissed his way down her fantastic legs to her feet. He kissed and licked the bottom of her foot until her reached her toes, which he sucked and licked. Jillian concentrated on enjoying the experience and not giggling when his tongue tickled her. Patrick luxuriated in the slightly sweaty smell and the smooth softness of her toes in his mouth. Patrick switched feet and kissed, licked and nibbled her other foot and toes. While he performed his ministrations, Jillian regarded him with a look of tenderness. He was proving to be quite the compliant, generous and pleasing lover.

"Take off your underwear," she suddenly commanded.

Patrick pulled his boxers off and his rampant cock jutted out proudly. It was circumcised and a little over seven inches long and around two inches thick. Jillian smiled because his dick was just the right size, not too long or overly thick but definitely substantial. His pubic hair was a neatly trimmed mixed-gray patch and his balls were shaved.

"You have a very nice looking dick, Patrick," Jillian said.

"Thank you," he replied, beaming with pride.

"Now, take my panties off - with your teeth," she ordered.

"Yes, ma'am!"

Jillian rolled over onto her stomach then knelt with her ass in the air, her legs spread and her head resting on her arms. Patrick kissed his way up her thighs and captured the waistband of her panties with his teeth and tugged until he had pulled them down to her knees.

"Lick my ass, Patrick, make my asshole nice and wet," she said. "Worship my ass."

Her ass was flawless, two ebony globes of velvety flesh, which Patrick starred at in rapt adoration before setting about his task. He started by gliding his strong hands along the back of her legs from her calves to her thighs before kneading her full buttocks. He stroked her cheeks before pressing his lips against her smooth skin. He kissed each cheek dozens of times before licking and sucking them. Then he parted her cheeks and ran his tongue up her crack, tickling the sides of each sphere. His lips and tongue made slow, sweet love to her whole ass. Just when Jillian thought he would never get there, she felt his warm, wet tongue brush against her tiny hole. A sexy low moan escaped her lips as his tongue lovingly circled her rosebud. She moaned blissfully and eagerly pressed her ass back against his face, giving him total access to her favorite place to be licked.

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