Melissa Learns to Dress Properly

All Melissa knew was that she had been rented for the weekend. She arrived not knowing what to expect, much less what was expected of her. All she had been told was that she had commanded a generous fee and that she should behave accordingly. Her entire body had quivered all week in anxious apprehension of what was in store for her. When the day arrived and she made her way up the street to the place, she felt her head swaying. Checking the number of the house, she swallowed hard. Her hand trembled when she rang the doorbell.

The maid opened the door, looked at her, and without a word, led her into the house, directing her to the living room. Stacey was there, sitting down, sipping tea. Without lowering her delicate porcelain cup, she instructed Melissa to undress. No words were minced, no useless words added. Slowly and very bashfully, Melissa undressed completely, revealing her masculine body. Stacey admired her for a while, asking her to turn this way and that, and finally instructing Melissa to bend over all the way. Melissa sensed that Stacey was now taking the closest look possible at the most intimate and secret parts of Melissa's body. She approved what she saw. Instructing the maid to prepare Melissa, Stacey went back to her book as the maid led Melissa out of the room and into the preparation room.

The maid told Melissa to step into the bathtub, brimming with hot water and bath soap. Donning rubber gloves, she rubbed down Melissa completely, from head to toe, back and front. Melissa squirmed when the maid inserted her gloved finger into Melissa's ass, but the maid hardly reassured her, "This is going to be the least of your worries this weekend." Now Melissa was very nervous indeed. But still in the bathtub, the maid proceeded to do her nails, with the most intensely delicate manicure and pedicure imaginable. Melissa could have stayed there all evening, so delicious was the feeling!

"Don't get too comfortable," the maid told her, adding, "we still have a lot to do." And with that she told Melissa to stand up, step out and return to the couch. Melissa was trembling: she could see what was coming next. It was only a matter of time. The preparations said it all. The maid rang a buzzer. A few minutes later, Stacey walked in. The maid stood still. Stacey examined Melissa's clean body. "Proceed," she told the maid. Now Melissa had never had an enema before. It felt so strange and so unusual, yet she knew that with Stacey she really did not have a choice. Melissa was actually feeling quite proud of her masculinity, her erection bobbing up and down. The enema bag filled her to bursting. The applicator was so cleverly designed that no matter the pressure Melissa felt inside her, no water was escaping. Stacey told her to lie on her side. She massaged Melissa's tummy deeply, feeling the water sloshing around inside her. And when Melissa showed that she could not contain herself any more, Stacey asked the maid, ever so crisply, to lead Melissa, enema bag and all, to the toilet to relieve herself. Melissa was embarrassed and self-conscious to no end, but deep inside she felt clean and empty.

The maid led Melissa back into the bathtub, now replenished with fresh, hot water. Safety razor in hand, she shaved Melissa completely from the neck down. Her body was soon smooth and soft. The maid had paid special attention to shaving over and over, in all directions, the scrotum and left nothing in terms of pubic hair all around Melissa's genitalia. Stepping out, the maid led her to a sofa where she painted Melissa's fingernails a bright pink and her toes a bolder shade of pink. All nails then received a thin, white line at the tip to further accent her feminine appearance. Her hair was coiffed carefully. Her entire body was bathed with a scented lotion; giving it a soft shininess that Melissa had never imagined possible.

She stood tall and proud, eager to receive Stacey's admiration. Stacey seemed to have something else on her mind. She walked over to Melissa. Taking her erection in her two hands, she massaged it deeply, almost too perfectly, Melissa thought to herself. Then both hands came off. Melissa sighed. Stacey placed her hands squarely on Melissa's testicles. She squeezed. She fondled. She squeezed harder. She massaged. She squeezed even harder. Melissa was in heaven! Suddenly, she felt the sharpest pain, immediately followed by waves of a joy she had never felt before, ever in her life!

"There, you won't be needing these any more," Stacey spoke softly, without emotion. Melissa raced her hands down. In the place where her testicles had once hung so full and so proud, now there was nothing. Nothing at all. Nothing except the flappy folds of a very clean-shaven scrotum. Melissa understood. Stacey had tucked her testicles, deep into her pelvis! When she finally overcame her surprise, Melissa could feel that her erection was harder than she had ever felt it before.

Stacey led her to the master bedroom, picked out a finely decorated bra and matching panties. Melissa wore them, unsure what to do with her erection. Stacey solved the issue: she simply pulled it out to one side and let it throb into the open air. The garter and stockings added the perfect touch. Melissa saw herself in the mirror out of the corner of her eye. She was stunning and she knew it! She could have masturbated right then and there, such was her joy!

It turns out that Melissa was a closet cross-dresser. While in town on a business trip she had decided, quite bravely, to experience for the first time the happiness of being a woman. She answered a personal ad. One thing led to another and on her next trip she finally accepted the conditions. This had led her to Stacey. It would change her life forever.

Stacey was of course oblivious to this line of thinking. Instead, she was busy picking out a dress for Melissa, finally settling on a colorful one, just slightly revealing her bra, and of just the proper length to cover half her thighs. Melissa was painfully aware of her erection throbbing, but if Stacey noticed it, she made no mention. Sitting down, the maid put on make-up on her face, doing her eyes, checks and finally lips, adding a touch of exquisite perfume. Stacey picked out matching high-heel shoes. Melissa was complete! She was a woman! And a most deliciously attractive one at that!

The maid photographed her in all feminine poses. Melissa was smiling from deep down inside. She was swooning. She felt almost in love with herself. Stacey spoke softly again, and quite matter of factly, "Sweetie, tonight we are going out to dinner and a party. There will be all women there. All eyes will be upon you. Make me proud."

Melissa could not have wished it better! She wanted to kiss Stacey a million times! She wanted to thank her with a gratitude that transcended words! she was ready and eager to please Stacey. No matter what Stacey could ask for, Melissa would outdo all expectations! She knew it! She was a woman! She was ready to be taken as only a woman can be taken!

"One more thing," Stacey mentioned, almost in passing. Melissa knew that anything Stacey could ask for, she would do. Stacey continued, still very softly. "We must make love before I ready myself for the party." Melissa thought she was going to faint! She was in ecstasy!

Her delight would not last long. Stacey asked her to kneel on the floor. Melissa obeyed. Stacey asked her to raise her dress. Melissa complied. Stacey asked her to drop her panties. Melissa was not quite sure anymore. It did not matter to Stacey. Very businesslike, she went over to the dresser, opened the second drawer and seemed to be staring for the longest time at its contents. She made up her mind. Turning around, Melissa almost fainted. In Stacey's hand was a strap-on dildo. It was relatively small, very thin, aggressively textured and rippled. The maid handed Stacey a fresh set of batteries. Stacey dropped her panties on the floor, raised her skirt just enough to reveal her almost bald pube and the maid helped her strap it on tight. Melissa could hear the noise as the vibrating dildo was turned on. She clenched her teeth. The maid applied a generous amount of lubricant all over Melissa's virgin ass. It felt cold. Stacey did not seem to be aware of any discomfort, physical or mental, that Melissa was having.

She stood behind Melissa. It was the point of no return. Melissa was trembling; her mind was spinning. Stacey pressed. At first Melissa was aware of the tip of the dildo pressing against her virgin ass. Stacey pressed just a bit harder. It was just hard enough for Melissa to feel it trying to make its entrance, but not hard enough to actually enter. Stacey seemed to know exactly how to master the technique. Melissa was going out of her mind. Stacey pressed just a trifle harder. The tip entered! Melissa had never ever felt so aroused! She knew that her erection was wildly bobbing. She was desperate. She tried to push back and take it all in. Stacey was too good for this. She knew just how to withdraw, keeping the pressure all along. Slowly, very slowly, excruciatingly slowly Stacey mercifully continued to press. The strap-on dildo was making its way in! Melissa could feel it! She could feel each ridge as it entered her. She was welcoming it! If Melissa had known how to dilate her ass, she would have done so eagerly!

Stacey was very good at this, extremely good, Melissa realized! When the penetration was complete, Stacey altered her pace. She would enter very slowly. Once inside, she would complete the penetration very quickly, holding it inside just a second, and then withdraw, at first quickly, but the last inch at a snail's pace. Her testicles, now safely tucked deep in her pelvis were feeling the brunt of the dildo moving in and out. It was the best testicular stimulation Melissa had ever felt! Over and over, Melissa felt her joy of being taken as a woman. In the fog of her mind she was vaguely aware that Stacey was also having her own delights from the vibrator actively stimulating her clit. Melissa was in heaven!

Melissa was vaguely aware that Stacey was entering her climax. It was slow, powerful, and Stacey was quite noisy about it, moaning, groaning, and finally screaming. Just as Melissa was about to have her very first anal orgasm, Stacey pulled out.

Melissa was in tears.

It had been so close!

Stacey was oblivious. She stood up. Instructing Melissa to put her panties back on and straighten her dress, she told Melissa to follow her. Melissa, dressed as the most beautiful woman, her ass still throbbing with the after-glow of her near-orgasm felt happy. She had almost climaxed as a woman, that was all that mattered now! She stood admiring Stacey as she undressed. Her tiny breasts were crowned with equally small nipples, now dark and hard like cherry pits. Her tall, very thin body looked so perfect!

Melissa was happy she was a woman for Stacey this weekend!

Stacey stepped into the shower. She bathed, dressed impeccably, with all the accouterments of a refined woman. Melissa admired her, wanting to be like Stacey tonight and every night! Purses on their hands, they made their way to the door, arm in arm.

Suddenly, Stacey stopped in her tracks. For the first time, she laughed. Kissing Melissa lightly, also for the first time, she exclaimed, "I am so excited I almost forgot something!" Melissa laughed timidly, not quite knowing what they had forgotten. Stacey solved the question with her action, as she always did. Leading Melissa back into the master bedroom she opened the drawer in the dresser. Inside Melissa saw the largest collection imaginable of strap-on dildos, of varying sizes, textures, shapes and types. Suddenly Melissa understood what Stacey was telling her through the haze of her mind. "Sweetest Melissa darling, pick out the one you want used on you. After all, the women tonight will want to try you out."

Melissa swallowed hard, closed her eyes, and picked out anyone, not knowing which.

And with this they laughed and walked out, hand in hand, two beautiful women into the night.