My First Time Out Ch. 01

Chapter 1: The Preparation

Shane, a 24 year old blue-eyed, blonde-haired salesman boarded the airplane enroute to beautiful downtown Salt Lake City, Utah. He had made the trip many times. He always conducted his business in a timely fashion so he could get back to his office making sure not to miss any other business opportunities. But this time was different. It wasn't going to be business at all, (even though he told his boss it was). Shane had this week-long trip planned for months in advance.

As the plane departed from his hometown, he knew he was "free" and could finally be the person he had always dreamed of…….Shayna! The two hour flight gave Shane enough time to go over his check-list. For months he searched the web for the perfect outfits. Lingerie, make-up, wigs, manicure sets, jewelry, breast forms, and all the other accessories necessary to go out dressed as a woman for the first time EVER! Shane discreetly purchased these items on-line and had them shipped to Salt Lake City (where he had rented a lock box for the last six months).

Shane had been nervous about being "passable" as a woman, so he went on a diet taking his weight from 160 pounds to129 pounds. He was a mere flesh and bones. With his height at 5'-8" and his non-muscular but toned body was a sure "pass". Shane subscribed to online make-up lessons and practiced at home after midnight, making sure he wasn't interrupted. These thoughts re-assured his confidence, but he still wouldn't be totally satisfied until he was sure the lingerie, skirts, blouses, and everything else were the correct sizes. One thing was definite, his feet had not shrunk and the three pair of size 10 ladies heels should fit!

* * * * *

As the plane landed, Shane's palms were sweaty and he was filled with anxiety and couldn't wait to deplane. After getting his luggage and renting a white Pontiac convertible, Shane headed to the Marriott in downtown Salt Lake City. The Marriott would be his new home for the next seven nights. It was a beautiful spring Friday afternoon, but he knew spring in this town could be rather cool at night. Shane was happy he ordered the long leather jacket at the last minute and hoped it arrived in his lock box on time.

As he arrived in his room, the bellman (with Mario on his name tag) asked if he needed anything else.

"No thank you sir, but one question. This isn't just an ordinary room that I usually get here, this is the "Executive Suite," stammered Shane!

"I know, we have had many a party up in this Suite. The manager said since the Suite wasn't reserved and you being a good customer, he decided to give you this Suite for the same price as a normal room," replied Mario.

"Well, if its boring on the town tonight, I just might start a party," giggled Shane.

After Mario left, Shane quickly picked up the telephone. He called the lock box manager and ordered them to deliver the packages to the Executive Suite at the Marriot Downtown. Then he dialed room service ordering one bottle of red wine, one bottle of white wine, some beer in a bucket of ice, and a pack of Virginia Slim 100's. Even though Shane didn't smoke, he thought Shayna might want an occasional cigarette. Either to calm her nerves or use it as a prop to facilitate sophistication.

Shane sat back on the king-sized bed looking around the glamorous suite. He viewed the leather couches, the bar with granite counter tops, five different modes for the priceless light fixtures, and a three-way mirrored make-up table with ample lighting. There were mirrors on the ceiling and walls. The large round jacuzzi/shower combination was near the picture window that over looked the city.

Only minutes had passed when room service knocked on the door and a 20 year old dark-haired, well-built stud arrived. The stud wheeled the cart into the room and delivered the goods as ordered.

As Shane signed the check and tipped him, the young stud said, "You expecting company tonite?"

Shane was shuddering inside, but cool on the outside and politely responded, "Ummmm maybe." He really wanted to say, "Why don't you come up here about 10 o'clock and see for yourself!"

Shane opened a cold beer to calm his nerves for his next package. Only seconds later the lock box delivery man arrived with a cart full of boxes and packages. After the deliveryman left, Shane guzzled his beer like it was water and got to work unpacking his "real" clothing and accessories. When Shane finished unpacking and putting things away, he was so happy everything arrived in good shape. Even the long leather coat that he almost forgot to order had arrived. Shane yelped and squealed like an excited little girl.

It was now three o'clock in the afternoon and Shane started the shower that would initiate his transformation. He shaved hair from all his body parts carefully, but left a cute little blonde triangular patch above his 5" cock. With a tweezers, he plucked the tiny hairs from his ass crack making sure his new pussy was shiny. Next he applied hair remover over his entire body. After cleansing off the excess hair remover, he noticed how smooth and stubble free his body parts had become.

Now it was time for a jucuzzi bubble bath with feminine fragrances and oils. He poured himself a glass of wine in an expensive crystal glass. Shane felt sooooo feminine that his face, legs, chest, and underarms were polished. He ran his foot up and down the slippery legs. His hands rubbed his clean- shaven, and now soft chest. His face felt velvety to the touch. An hour in the tub felt like heaven, but Shane knew he still had work to do to complete his craving transformation.

As Shane got out of the tub, he refilled his glass of wine, and wrapped one huge towel around his clean-shaven body and another towel was tied around his scalp. He danced over to the dresser where he had previously laid out his sexy lingerie. His garments were in the order he planned to wear them (each day a different set), and picked up the stretchy, lacey red garter skirt with the attached G-string and garter straps.

As he pulled the G-string up his silky legs, he felt stimulation. He could also fee the chills running up and down his spine. The touch of satin and lace running up his long smooth legs was a turn on. By the time he wriggled the g-string over his ball sac, his cock was at full attention. There was no way this cock would fit into the G-string pouch, but then he remembered the black padded gaffe.

It was a special gaffe designed to show smoothness in the front and not publicize a bulge. Also, it had special hip and butt pads built into it with a unique silicone-like fabric. It's the same material used in modern breast enhancers.

He tucked most of his male parts into the g-string pouch. Next Shane squirmed into the gaffe. It was perfect, fabricating a slight butt and hip jiggle, as well as feminine curves. After all, Shane was so skinny he needed extra hip and ass.

At that point he unpacked the latest model silicone breast enhancers. They were satiny and felt like jelly. The latest model fake breasts had self-adhesive backing allowing him to go bra-less if he chose. They would produce a B cup and would be a definite fit on his lean body. The taut, life-like dark nipples jutted out almost a half-inch!

Shane laid on his back on the bed and looked into the ceiling mirror. He carefully positioned his new breasts. It took only five minutes for the adhesive to dry, but it seemed like he been there for hours. He felt for his bra, but remembered he left it on the dresser in the other room. He was afraid that his new breasts would fall off from lack of support.

Shane walked gingerly as he held his new breasts with both hands like it was a new-born baby. Each step made him more confident. As he walked past the make-up table, he slowly took his hands away from his chest. His new breasts felt heavy and awkward at first. Then he watched his 'life-like' tits jiggle and bounce as he lightly jumped up and down.

After Shane got more familiar with them, he massaged and kneaded his tits. He played with his nipples by rolling the stiff buds between his thumb and forefinger. He even flicked and tweaked them.

THIS WAS THE TURNING POINT. Shane would now call himself SHAYNA…. AND….. HER!!!!!!!!!!!!!!!!!

She hooked her new red satin Victoria Secret bra in the front and slung it around so the cups were under her breasts. Then she pulled the straps over her shoulders and found it to fit tightly and add support on her new breasts. This special bra had gel built into the cups that added almost an extra size. It was a great choice for the first night out. The thicker material would not let her fake half-inch long perky nipples protrude through a tight top (as she planned to wear).

Shayna's next decision was stockings. She couldn't decide between two pair of white. She was acting more like a woman and couldn't make a decision. Should she attach the garters to stockings or wear the stay-up pair. As she sipped on her glass of white wine, she decided to detach the garter straps from the garter skirt. She decided on the sheer white, back seamed stay-up stockings with frilly and fluffy lace at the top.

As she seductively pulled each stocking up her smooth leg, the same sensation hit her, but this time her girl-cock couldn't swell or rise because the gaffe was performing its job. She could already feel pre-cum secreting into her satin G-string.

Shayna gingerly adjusted the thicker white seam that ran up the back of her legs. As she looked in the mirror, she made sure both seams were perfectly straight and centered.

Shayna's next plan was to do her makeup sitting down in front of the well-lit three-way mirror. She pulled out a black head-band and put it on her eyes. Then pulled it down in the back close to the nap of her neck. At this point she gradually pulled the front of it up towards her hairline little by little, each time stretching her scalp back. This process tightened her forehead, and raised her eyebrows. It even made her eyes bigger. It was tight and uncomfortable, but she knew this was an important accessory to beauty.

She took off her bra and powdered blush on her chest to blend the color of her skin and fake breasts. She dusted blush from her chest to her shoulders and neck.

Her clean-shaven face was smooth, but decided to use beard cover to anyway. The creamy substance would help preserve her smooth look. In case she had a longer evening than expected, the beard cover would prevent a five o'clock shadow.

Using a tweezers, Shayna plucked her eyebrows one by one causing excruciating pain. It was time to take a break.

After her break, she looked in the mirror using a soft, sexy, higher pitched voice that she practiced at home, "Shayna baby, even without makeup, you are gorgeous, but lets get back to work to turn you into that skinny little fuck-slut-whore you yearn to become!"

Shayna squealed with delight and repeated it over and over again, each time holding some syllables longer creating a sexy voice.

She repeated this annunciating her words, "Shhhhhhaaaaaynaaa, the sleeeeeeazy little fuck-slut whooooooooooore!! Shhhhhaaayna, the fucK-sluT whorrrrrrrre, letsssss get back to worrrrrrrK."

And so she did, applying a darker foundation than her normal skin color. She applied powder with a brush taking off the shine, and complemented it with rose blush on her cheeks. When she inspected her work in the mirror, there wasn't a hint of any lines or makeup shadow.

Shayna picked up her new false eyelashes that were pre-painted jet black. She decided to trim them a little because on her first night out, she didn't want to look like a Las Vegas showgirl. After all, she had four more pair in her make-up bag.

After the glue dried her eyelashes enough, Shayna batted her eyes in the mirror, then winked and said, "seeeeeeeeexy Shaaaaaaaayna!"

Extra jet-black liquid eyeliner was used to cover some of the excess glue. She combed out her bottom lashes and applied three coats of black mascara matching the top lashes. Again she drew a line with liquid eyeliner on the bottom lid to a little farther out than the corner of her eye. Now a little extra swoosh up giving her a "whore-like" look. With steady hands, she painted her thin brows dark brown. She positioned the thin pencil a little higher up than her normal brow-line.

Using a combination of charcoal and lavender eyeshadows, she coated her upper lids until they were filled in perfectly. It took three coats to blend and color her eyes properly. At the corner of each eye she flared the charcoal/lavender paint upwards matching the flare in her eyeliner. Finally, a light sprinkling of gold glitter was applied on her wet painted eyes.

The extra flare of eyeliner and eyeshadow almost made her bedroom eyes say, "COME FUCK ME!"

It was now getting very hot under the lights and she didn't want any melting or running of her makeup. Shayna had to get away for a minute, but before she got up, she took one more glance at her treated face in the mirror.

Shayna shrieked, "WOW, what a lecherous little SLUT!!"

At her jewelry box she decided to put on her three inch gold hoop earrings. Naturally her ears were pierced six months ago. They felt heavy at first, but after looking at this exquisite little fuck-slut in the mirror, she no longer felt the weight. Instead she felt the dangling and swinging of her newly purchased jewelry.

Then one ring on each finger of the right hand. The same on the left hand, except for her ring finger. She didn't want to scare any gorgeous hunks away this evening.

Shayna turned in the mirror and looked from every angle. Something was missing, but before that thought ended, she already knew.

"My lips and my hair," she mouthed silently.

Shayna strutted back to the makeup table. With dark red lip liner, she penciled in full pouty lips. Then she coated them with a thick, creamy, "blood-red" lipstick. A very fuckable combination!

To top things off, she dug into a wig box and picked the "hair" she ordered online five months ago. It was her favorite and still in perfect shape. A blonde wig pre-pinned up (by the factory) in the back and curly at the top. It had one seductive tendril spiraling down each side of her pretty face. The curl went past her ears and sensually onto each shoulder. She made sure her there wasn't any hair covering the gold hoop earrings. In front, the three-inch straight cut bangs were perfect, stopping just above her raised eyebrows.

As Shayna turned sideways, the three-way mirror allowed her to reveal her long smooth kissable neck. She felt so pretty, yet so trashy.

As she looked in the mirror she squealed loudly, "SHAYNA BABY, DO ME RIGHT NOW, mmmmmmmmmmmmmmmmm YEAH!"

The lights in the city were starting to come on, as the sun was setting over the snow-capped mountains. Shayna knew she had a minute or two to relax. She lit a cigarette, and poured herself her third glass of wine. Shayna took a weak drag off the long thin cigarette and seductively blew out the smoke upwards.

Shayna watched every delicate gesture in the mirror. She learned to move slower portraying a more feminine approach. She practiced different mannerisms as she held the cigarette. She cocked her wrist at certain angles and extended her fingertips toward the ceiling. She knew her body language would play an important part of the evening. A drag off the cigarette from the corner of her mouth proposed a different message than a drag from the center of her lips.

Then she looked at the red paint that was on the end of the cigarette. She quickly took a sip of her wine, wanting to see the lipstick smudge on the crystal glass. The sensation was coming back and her girlcock was trying to work its way through the gaffe! More fluids were leaking, just like a girl! When she put her hand to her crotch there was no sign of a cock. It was still smooth and flat.

Shayna looked at the clock. She briskly stashed out her partially smoked cigarette, and decided she should eat some food. After ordering shrimp cocktail and large bottled water she attentively asked room service to leave the cart outside her door. While eating her shrimp cocktail, again Shayna watched every move in the mirror. She practiced her posture and dinner mannerisms.

Every bite she practiced something different ranging from cute and petite, to sexy and slutty. She got a little lascivious on the last bite. Holding the tiny fork upside down, she stretched her tongue outward and started flicking the prawn. Then she tongued it, kissed it, and sucked it like it was a curled up little cock. She even went to the extreme of making noises and talking to it.

In her sexiest voice she said, "Mmmm baaaaaaaby, I want to eat you up! Shayna wants you in her hunnnnngry mouth. Pleeeeeeeeeeeze, pretty pleeeeeeeeeeze, give it to Shaaayna. Uh hmmmmmmmmmmmmmmmm. Oh soooooooooooooooooooooooooo yummy!"

It was time to get dressed for her hot night on the town. She clasped her bra, and readjusted the cups pushing her fake tits together and up trying to produce cleavage. She pulled out a red lycra micro mini skirt. The skirt didn't have any buttons or zippers on it. The material was just stretchy enough to fit over her hips and ass. After she slipped it on, she ran her hands around her curvy hips. It didn't seem to fit smoothly. The tight fabric seemed lumpy caused by her garter skirt underneath.

She hastily removed the garter skirt allowing the size 8 micro mini skirt to fit skin tight around her fake hips and ass. It looked astonishing next to her flat stomach. The skirt was not quite long enough to cover the frilly, fluffy stocking tops, but that just added sexual request.

Her top was a tight white nylon (partially see through) halter that would cover her bra straps and shoulders. The ¾ length sleeves had a thicker white seam down the back side of each arm matching her stocking seams. It was so tight Shayna struggled while putting it on, but finally succeeded. She knew it was the perfect choice. The top brought to light a tint of her red satin bra and showed some cleavage.

It fit snugly over her shoulders and arms. It barely covered the bottom of her breasts exposing most of her skinny rib cage and flat firm stomach. Shayna was soooooooo horny, she could feel her fluids leaking even more. She was dripping like a faucet!

The shoes were an easy choice. It was a no-brainer that Shayna chose the shiny red patent platforms that fashioned two ankle cuffs. A petite gold buckle would fasten the each ankle cuff. The bright red platforms were 2" at the toe and the gold stiletto spikes that accented the ankle buckles were five inches tall.

Six months ago, Shayna had purchased two-inch heels and practiced at home, but now she had the feeling she was on stilts. She knew she would need to practice balance and walking. The training would be worth the extra work because the "come-fuck-me" pumps made her already long legs longer. When she walked, her ass wriggled, stockings swished, and her steps became daintier.

The next 30 minutes Shayna versed her strut around the Suite. Keeping an eye on the mirrors, she sucked in her stomach and tilted her shoulders back. She even turned on some music and rehearsed dancing. Shayna became more confident with each step.

With her legs straight, Shayna bent over her makeup chair to briefly check her painted face. With the help of the back mirror, she noticed that her skirt was hiked up in back exposing half of her taut little ass! She even stayed in that position as she prepared to put on the last item, pressed fingernails.

Shayna ordered seven sets of fingernails that were all pre-painted in different colors. She grinned with the thought that she wouldn't have to mess with polish. The choice for tonight was shiny red, matching her "blood-red" lipstick.