My First Time Out Ch. 01.5

Shayna paced back and forth throughout the entire Suite while she nervously smoked the long thin cigarette. She occasionally stopped and peered into the mirror thinking that all of her hard work had gone to waste for tonight. She was dressed to kill and had no place to go. The red patent platforms with 5” gold colored stiletto spikes. Her long legs encased in sheer white stay-up stockings with frilly lacey fluff at the tops and a thick white seam that ran down the backs. The skin-tight red lycra micro mini skirt fit skin tight. She could hardly move in her nylon halter that covered her bony shoulders. It had ¾ length sleeves and a thick white seam down the back of her arms matching her stocking seams. This was her favorite outfit! Shayna’s eyes were flawlessly colored like an expensive hooker and her “blood-red” lipstick and matching long square-tipped nails were ready for action.

She had only partially dressed-up at home, or practiced certain facets of her makeup. Never before had she been completely shaven, fully dressed, and primped with makeup all at the same time. Being dressed 100% female brought forth sensitivity in her personality and shaped her behavior even more towards femininity.

Her girl cock was confined in the gaffe concealing any suspicion of manhood and her fake silicone hips and breasts purveyed a feminine emergence. In tandem with Shayna’s exterior appearance and a full rehearsal of her ladylike gestures, even her emotions started to change. At this time, Shane’s manly core had been completely removed.

All at once, ideas started coming to her. She had some choices: 1) Order something from room service and when the young stud gets into the room, give him a quick blow job. 2) Call the lock box company and ask for the sumptuous delivery boy. Pull him into the room and molest him. 3) Call an escort service and ask for a tall young hunk to take her to a club.

Shayna thought the first two ideas would not get her out of the room, but didn’t want to spend the extra money on a dating service. If she worked fast, maybe she could possibly accomplish all three choices in one night! With a tippy-toed run Shayna quickly strutted over to the phone and dialed room service.

“Hello, room service may I help you, answered the man?”

Shayna could not get a word out because she was wondering which voice she should use, Shane’s or Shayna’s!

“May I HELP you, blurted the man?”

In a sweet, sexy, well prepared voice Shayna responded, “Ummm, yes, my aaaaaa friend didn’t properly tip the room service boy earlier this evening, and was wondering if he was going to be near this room and aaaauuumm….could swing by………..”

The Room Service man abruptly cut her off and said, “He’s been off work for over an hour, but you can either drop it off at the front desk or catch him tomorrow evening.”

Before Shayna could say anything else, she hung up the phone.

Next, she called the lock box agency and got the answering machine.

‘Thank you for calling SLC Lock Box Service, our office hours are 8 am to 6 pm Monday through’………CLICK!

Shayna dejectedly hung up the phone. It was like getting turned down on a date!!!

Shayna’s least choice now cycled into her ONLY choice. She opened the phone book to the yellow pages looking under “Escort.” Studying the titles, she tried to pick out the company that would best fit her needs.

“Yes, this is the prime choice,” she said aloud.

Not only was the name in bold print, but it impressed her prediction of potential accomplishment. “Both-Ways Escort Service.”

Shayna cleverly planned and practiced what she was going to say. She nervously dialed the phone and cleared her throat.

“Good evening,” the lady receptionist said.

Without hesitation Shayna said, “Yes….hi, I am in town for a few days, and was wondering………”

The receptionist cut her off and said, “Which sex do you prefer hun?”

“Well, I am shemale, and would like a tall dark-haired good-looking gentleman to escort me to a club for dancing and maybe more,” demanded Shayna.

The receptionist said, “Oh, I have the perfect fit for you sweetie. He is $150 per hour, and any extra curricular activities are negotiable; cash only. His name is Franky, and will be there in 15 minutes.”

Shit, 15 minutes! Shayna scampered over to her makeup table to touch up her face and apply another thick, creamy coat of “blood-red” lipstick. Next she looked in the mirror from all angles, making sure everything was perfect. She straightened the white seams that ran down the back of her stockings. She tugged at her skirt and ran her long thin fingers over her crotch feeling no sign of a cock. The dripping sensation was coming back making her panties even more wet! Shayna was soooooo horny, yet filled with anxiety.

Suddenly, KNOCK-KNOCK. Shayna daintily walked towards the door with her arms straight down her sides, palms facing down, and fingernails pointing towards the ceiling. Her arms moved delicately with each tiptoe step. Her skinny ass swayed back and forth like it was advertising for a nice thick, hard, cock to be crammed into her virgin slit.

She watched her tits jiggle as she passed by the mirrors, and her strut became more confident. Shayna had nasty thoughts of becoming a trained fuck-slut during the evening.

Before opening the door, she decided to examine her prize through the security peep hole. Almost gasping outloud, Shayna covered her mouth with both hands as she looked down at the floor. She blinked, then peered once again through the hole and still couldn’t believe her eyes. Standing outside her door was a dark-haired, half-balding, 5’-6” 200 pound, 40 year old man!!!!!!!! Moreover, he wasn’t even cute!

Then, KNOCK, KNOCK, KNOCK! Thoughts raced through Shayna’s cloudy mind. She could either answer the door, or just stand there silent and hope this nerd would go away. She thought about the consequences of each alternative. If she let him in and they went out clubbing, she could get to the bar and ditch him. Or she could not answer the door and spend the rest of the night in her room alone.

Shayna knew she wanted to go out on the town, but decided she could not be seen with this twit. She could only imagine getting glares from everyone as if SHE was the hooker, and HE was the customer. After that quick illusion, Shayna adamantly decided NOT to answer the door.

Shayna stood quietly trying to take slow deep breaths without making a sound. It seemed like hours had passed in complete silence. She did not want to go face to face with him. She only had to withstand one more set of KNOCKS before the nerd finally gave up and left.

After a few minutes, Shayna’s feelings changed from scared and nervous to discouraged, then mad. She wanted to call the escort service and give them a piece of her mind. She walked over to the phonebook to re-look up the number. While scrambling through the E’s for Escort, her eye caught the attention of something peculiar that happened to be listed under the Entertainment section.

Adult Bookstore, Clothing & Tattoo Parlor-----State Street---Salt Lake City----and the phone number. Shayna knew this was her night out, and nothing would stand in her way! It was within walking distance, but she decided to take a taxi instead.

Before calling a taxi, Shayna needed to build up a little more courage, so she poured herself a glass of wine and had a cigarette. She was consumed by thoughts of getting “noticed” as a man. Even worse, getting picked up by the police (for some unknown or far-fetched reason) and being hauled off to jail! She knew these thoughts were unrealistic when she looked into the mirror.

There stood a skinny, ravishing, sluttily dressed, blonde staring back at her. Her long leather jacket would cover up everything except for the “come-fuck-me” platforms, the whore-like painted face, and the seductive blonde hair pinned up in the back. She then primped her hair making sure it was still in place and smiled at herself in the full-length mirror.

When Shayna ordered the taxi, she instructed it to pick her up at the side entrance of the hotel because of discreet reasons. One more spray of perfume and a touching up of the lips. She picked up her red leather purse and literally threw a small makeup bag, perfume, lipstick, loose cash, room key, cigarettes and a lighter into it. The taxi arrived as she walked out the side exit door of the hotel.

“Great timing,” she mumbled to herself.

After Shayna gave the instructions to where she was going, there was no more conversation during the five-minute taxi ride. Upon arriving at her destination, she rummaged through her purse for a $10 bill. The taxi driver exchanged the cash for a business card enabling a return trip to the hotel. Before getting out of the taxi, Shayna examined the small biker crowd hanging out by the front door. Men and women alike, some sleazy, some hard-core, but what else should she have expected?

Shayna opened the taxi door, slung her long legs out making sure her knees stayed together like a lady. Her bright, shiny, red patent platforms reached the pavement in unison. With her feet close together, she stood up like a professional. She adjusted the leather jacket tie string and cavorted through the crowd towards the front door.

As her gold spiked heels clicked on the pavement, all eyes were on Shayna, but she was afraid to make eye contact. She stayed focused straight ahead almost giving her a disposition of a stuck-up bitch. There was some faint whistling coupled with soft murmurs and sexual subtleties.

One guy said, ”Hey ba’aby, wanna get lucky.”

“Daddy’s right here waitin’,” murmured another man.

As Shayna entered the front door, she veered to the right into the adult bookstore side. She subconsciously thought she wanted to get accustomed to the environment minus conversation. She felt overly dressed and out of place at first. Shayna knew she was on a mission and did not want to be denied.

Shayna pretended to look at magazines, but was really exploring the place with one eye. There was a video tape section, a lingerie section, and a bondage section. In the back there appeared to be an ample number of peep show booths.

After a short time, she got up enough nerve to check out the tattoo and piercing side. Upon entering, she noticed the walls were plastered with photographs and warning signs. Shayna was overwhelmed with the various tattoo designs; moreover, she was interested in the different body parts that COULD be tattooed. She had always been curious about tattoos and body piercings, but still maintained her opinion that too many of either ruined beauty.

A young kid (that didn’t look a day over 15) was working the counter and asked, “Whatchou interested in blondie?”

Trying not to respond like a bitch, Shayna said, “Just looking, thank you.”

The cocky kid said, “Do you have any tattoos or piercings other than the large hoops through your ears?”

Shayna fidgeted with her ears and giggled her reply, “Ummmm, nooooo.”

“Well a nice pair of diamond studs would look very appealing on your upper ear. They’re on sale for $99,” touted the kid.

With more assuredness, Shayna said, “I was thinking of maybe getting a small tattoo instead.”

The kid then escorted her into another small room in the back, and informed her of the tattoo/piercing sale.

The kid confidently said, “Pay for one, get the other half price!”

As he walked away he turned his head and said, “My boss will be here to see you in a sec…..He’s gonna LOVE ya……you are one fiiiiiine dudette!”

Shayna looked around the small room at the different sized needles and the array of colored dyes. She felt woozy and tepid so she unbelted the long leather jacket tie. The leather jacket was now open in the front revealing the skin and bones of her flat stomach.

As the door creaked, Shayna snapped her head around to see. At that point their eyes met. Her baby blues and his deep brown eyes focused on each other. Standing in front of her was a 6’-3” 205 pound curly dark-haired, well-tanned hunk! His upper body formed a “V” from his waist to his shoulders!

Shayna could tell he was neat and tidy by his attire. His hair was tightly groomed and was clean-shaven except for the short-haired goatee, mustache combination. His partially unbuttoned Hawaiian shirt evidenced his buff pectoral muscles. Trying not to stare, Shayna flashed her eyes up and down his body (using the quick once-over look). His arms and legs appeared muscular and the bulge in his crotch made her girl cock twitch.

As if breaking her trance, he said, “Hi there beautiful, my name is Dominique, the owner.”

Shayna could feel a lump forming in her throat and was nervous about speaking.

As alluring as possible, she choked, “Hi! Shayna.”

Gawking at her exposed mid-section, Dominique said, “I suppose you want a tattoo on your little stomach…..correct?”

Shayna shook her head no, but pointed around behind to her ass!

“Well sweetie, you’re going to have to take your long coat off so I can inspect,” Dominique ordered.

Shayna set her purse down on the table and the gentleman helped her slip out of the long leather jacket. Then Dominique opened a fresh box of Cuban Cigars and stoked one.

With aplomb Shayna said, “I guess it’s OK for me to smoke?”

As Dominique sparked the long thin Virginia Slim for her, Shayna put on her most tempting act. She sat on the high table and crossed her legs attractively. She leaned sideways bracing herself with one hand on the table. With her chin cocked sideways and down towards her shoulder, she dangled her foot into circles. The 5” long stiletto gold spike was only inches from his crotch.

Her bedroom eyes gazed at him as she answered small talk questions. She made sure she smiled and showed him her impeccable white teeth. As she smoked her cigarette and blew the smoke seductively upwards, she hinged her ankle up and down. It was as if she was directing his cock with her spiked heel, like an orchestra leader would use his baton.

Shayna ran her fingers seductively down her curly spiraling tendril, then primped the back of her hair. She teased his bulge without touching it. Her facial expressions were sexy. She moved her shoulders in slow motion as if he was massaging them with his eyes. She mouthed words toward him silently. She licked her lips as she stared at his bulge. She even simulated jacking him off with her feet. Shayna was not going to let this fine specimen get away!

After Shayna extinguished her cigarette, Dominique asked her in detail about the tattoo. She explained that she wanted a small, bright red pair of lips just below her tailbone, but above her ass crack. Also, underneath and partially around the lips in small letters she wanted the word “COCKSUCKER!!”

Dominique violently toked on his stogie, shook his head and said, “Wow Shayna. That is arrogantly slutty! I believe we can arrange that.”

Dominique suspected there was not much fat on this skinny slut’s body, and especially next to her tailbone. Even though her prescription was possible, she would experience tormenting pain. They would also need Dominique’s specialist for this process. He explained this to Shayna and assured her that it would be safe, but verrrrrrrry painful!

“Sir Dominique? I have one thing to confess and must be honest with you,” exclaimed Shayna. I am a shemale.”

Dominique laughed in disbelief and told her not to be afraid of getting her pussy fucked.

He said, “Shayna, we’re going to give you art work, we’re not going to fuck you!”

Trying to plead her honest case, Shayna said, “No really, I have a COCK.”

The look on Shayna’s scared face told him that she just might be telling the truth.

“Prove it,” he blurted loudly.

Shayna slowly pulled up her skirt and showed him the hip and ass silicone pads. With both hands, she dug her long fingernails into the top of her gaffe and g-string. She toiled it down past her triangulated blonde patch displaying the base of her girl cock. Her panty pouch was saturated from endless leaking fluids and made her short blonde pubic hair glisten.

“See, happy now,” she passionately said?

Dominique shook his head with approval.

Then with embarrassment, Shayna exclaimed, “You know, this is my first time out dressed as a lady.”

“No way,” Dominique replied in disbelief.

“No, it’s the truth, and I had nowhere to go tonight. I wanted to go clubbing, but didn’t have an ID card for ummm, you know, a woman,” pleaded Shayna.

Dominique said, “Well, I’m very pleased you stopped by.”

As Shayna wrenched the tight gaffe back into position, Dominique wrapped his muscular arms around her waist and his chest muscles were impending into her fake tits. She could feel the singe that this hard-body was generating throughout her nucleus.

As he held her chin up with his thumb and forefinger, he whispered in her ear, “It’s alright baby, I have a few shemale friends, but the reason I didn’t believe you is because you’re immaculate. From your pretty face to your petite body, and the manner you carry yourself with sex appeal. You’re a first class goddess! I’m not bi-sexual, but would treasure the idea of dating you,” Dominique stated.

At the same time Dominique lightly kissed her on the cheek, Shayna had tingly sensations up and down her spine.

She wrapped her thin fingers around his brawny neck, kissed him on the lips and said, “Thank you sir!”

Dominique left the room then returned with the tattoo-specialist named Gus. Gus had a measly body, greasy hair, and beady eyes. Evidently Dominique had explained to Gus all the facts about Shayna (the shemale). Dominique also must have told him the proximity of her tattoo, because as Dominique introduced Gus to Shayna, Gus instantly had suggestions about the position of her tattoo.

Gus actually talked Shayna into moving the bright red lips up above her tailbone. Unwaveringly he gloated about his artwork ability and told Shayna the small red lips would be a “come-on” just above a pair of low rider jeans. Gus promised her the word “COCKSUCKER” would be basted on much lower and be concealed, as long as she wore clothes. Shayna loved the ideas and concurred immediately.

Dominique pulled out a bottle of vodka from the freezer and poured a straight shot for Shayna.

“Follow my instructions dear, and the pain won’t be quite so bad,” he explained as he handed the short glass to her.

Shayna didn’t drink much hard liquor and never straight shots, but downed the pain killing vodka anyway. Then she had one more shot before Gus and Dominique positioned her on the table.

The top of the table was about even with Shayna’s waist. They bent her face down over the floor-bolted table. Her head extended past the other end allowing some freedom, opposed to her face being buried in the table.

With her legs straight and slightly spread, Gus strapped both ankles as well as both thighs to the solid steel table legs. Another strap was placed around her waist. The last strap was laid over her back just below her shoulder blades. The straps were cinched so tight that her flat stomach and fake breasts were compressed against the table. Shayna could feel her girl cock rubbing against the edge of the table. Gus asked her if she was able to breathe.

In between her abbreviated breaths, Shayna nodded her head and grunted, “Uh huhh.”

“Sorry Shayna, we have to do this to make sure you don’t move during the process. You know how proud I am of my artwork, and don’t want to fuck up your lips; HOWEVER, I would LOVE to fuck your real lips,” Gus said with a dirty laugh.

As Gus prepared for the procedure, Dominique pulled up a short stool and sat down by her head. He was now eye level with her.

Dominique soothingly uttered, “Now listen Shayna, we’re going to try to get through this without pain killers, OK?”