by John Dylena
After a while, he pulled away, and he once again whispered into my ear.
“I want to fuck that ass of yours. I want to fuck your little boipussy and take away your virginity.”
“Please… please, fuck me,” I replied breathlessly. “I want your cock in my boipussy.”
He pulled off my blindfold and kissed me. Then he lifted me up off of the bed and removed my cuffs. Then he sat on the edge of the bed, and I knew what to do.
I climbed onto his lap like a stripper at a club and draped my arms over his shoulders. I brought my lips to his and kissed him as I lowered myself onto him. I moaned loudly and he grunted as his cock eased into my ass. I took it slow, and the little pain that there was vanished as he filled me. Monica’s cock was a thousand times better than the dildo I had. There was a warmth to it that only heightened the pleasure.
Monica grabbed my hips and started moving them back and forth and up and down as his cock slid in and out. After a little while of this grinding, Monica wrapped his arms around my waist, and in one fluid motion, he turned me around and dropped me onto my back on the bed. He stood at the foot of it, and I lifted my legs up.
I threw my arms back over my head and closed my eyes me as he thrust in and out of my ass, fucking me like a porn star. He bent forward and brought his lips to my nipples, and I held his head there as he kissed and sucked on them.
He straightened up and grabbed my cock and jerked me off at the same rate he was pushing into me. My moans came faster and faster, shorter and shorter as I came closer and closer to cumming.
“Oh! Oh! I’m going to cum!” I shouted.
“Me too! Almost there!”
His thrusts became wild, and then I felt it. Monica pushed his cock as far into me as he could, and then I felt the heat from his cum inside of me. I felt it fill me, and it pushed me over the edge. I opened my eyes and moaned loudly as streaks of white-hot cum erupted out of my cock and landed all over my body, oozing down onto my lower abdomen.
Monica eventually pulled out and wobbled backwards. I could see cum dripping off of his dick as he stood there, breathless and exhausted. I was too tired to speak. I couldn’t even form a sentence. After a moment, he climbed back onto the bed and licked some of the cum off of me and kissed me. We kissed long and hard, and then we just cuddled for a while.
I ended up falling asleep next to him.
In the morning, we showered, had breakfast, and I said my goodbyes. It was strange seeing him in his normal male mode. It almost felt like he was a totally different person than the hot crossdresser I’d had passionate, kinky sex with the night before. I could say the same for myself, though. I felt like a totally different person than I was last night.
I wasn’t sure when I would see him again. I didn’t know when his work would bring him down here, or if I would ever get the chance to go up to visit him. All I knew was when I got back to my apartment, I realized I still had his room key.
[Me]: Hey, so I still have your room key…
[Monica]: Oh? Is that so? Well, I am checking out tomorrow… so maybe you should come on by before then and stay awhile. ;)
[Monica]: Maybe bring that pink skirt of yours and crop top and those slutty pink heels.
[Me]: Only if you promise to tie me up again and blindfold me.
[Monica]: Deal. Come by again tonight. I’ve got work and stuff to do.
[Me]: I’ll see you then!
[Monica]: Bye! *kiss*
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UPGRADED
Cody could never forget the smell of a casino; an odd mix of cigarette smoke and alcohol, topped off with desperation. Folks sat around the machines and risked their hard-earned money hoping, and sometimes praying, that the odds were in their favor that night.
Gambling was a cruel mistress. She lured you in with the promise of big money and kept you seated until your pockets were empty and your hopes dashed. She didn't suck you dry all at once; it was a slow, drawn out process that involved many small wins paired with slightly bigger losses.
You knew you were in Vegas when you stepped through the casino doors and walking toward you was an Elvis impersonator. It was the seventy-fifth anniversary of his death, and yet people still worshiped and bowed to the immortal King of Rock.
Cody shot the man a glance as he watched him go down the short set of stairs to the doors that he just walked through. He paid Cody no mind. His head was down and his eyes were forward. In his hand, he carried a small leather bag containing his personal belongings, but what Cody kept his eyes on was the impersonator’s face. The older, pudgy man was worn out, his weary face serving as the evidence of long hours spent singing and dancing.
Tonight is the night. Everything is going to change.
He kept his hands in his pockets as he maneuvered through the sea of slot machines and card and roulette tables. It was a Friday night, and the casino was packed. Even with the advanced technology in the present day, casinos hadn’t changed much, with the exception of the patrons.
Cybernetics had evolved to a point to where they were no longer just for people who had lost a limb or two from an accident, but for anyone with the bank account large enough. Of course, certain cybernetic implants were banned at a casino—things like eyes with zoom capabilities or anything that could improve your odds at a table or slot.
“Excuse me,” Cody said as he stepped around a waitress. He eyed her breasts as she turned to face him. The woman wore a skin tight red latex dress with matching latex boots. His eyes moved up from her plump bust to her face, and he returned the faint smile she gave him. The waitress’ makeup was heavily applied, not to mask imperfections, but because it was the dress code. In his mind he tried to picture her without the cosmetics and he wondered if bright green was her natural eye color.
Nowadays, changing eye color was as easy as applying eye drops. Matching eye color to outfits had been a popular trend for years now, and the laboratories behind the color changing drops were constantly trying to expand the color palette available. The newest color was his least favorite: jet black. Seeing men and women with eyes that matched their pupils was unnerving. Cody’s own eyes were brown, as dark as his hair, and he rarely changed them.
Right behind the waitress was her robot. Thin, sleek, and basic, the machine carried the drink tray in one of its many arms, furnished with built-in gyroscopes to prevent any of the beverages from spilling. Robots like these were everywhere in all sorts of industries and professions. Until the day where the machines looked and acted like the sexy waitresses that served the drinks, the cute blonde in the latex outfit didn’t have to worry about losing her job.
I wonder how much she makes a night? He looked back at her over his shoulder as he continued down the walkway in between the machines. She was bent over, and Cody could see the bottom of her ass and the thong that she wore under the latex. His attention moved from her to the sounds of someone winning a jackpot a couple rows over.
The lights on the machine lit up, and all eyes went to the elderly lady who just won a million dollars. Several big men in suits sprinted past him and stood next to the feeble woman. The crowd that had gathered around her made way for the pit boss, a tall blonde woman in a stylish skirt suit and heels. He’d always see her wandering around the floor during the many times he’d gambled here.
She silently walked up to the senior citizen and inspected the machine. Even with the constantly updating security, men and women skilled enough were still sometimes able to fool the machines. Those that were caught might ended up working for the casino as spotters to prevent tampering; they were the lucky ones. Some casinos were still owned and operated by the mob. If someone were caught cheating there, the unlucky soul never left the casino intact; limbs broken, fingers cut off, and in the worst cases, death. Bodies were never found, of course, but there were rumors.
Cody watched as the pit boss smiled and shook the old lady’s hand. The seven-foot-tall thugs in
suits escorted her away from the machine and off the floor. She would be taken into one of the back rooms where the casino would directly deposit her winnings into her bank account, then she would be escorted back to wherever it was she called home.
Every night he stepped foot into this, or any other casino, Cody wished he could be the one walking away with the big money prize. But tonight was different. Tonight, it was all on the line.
Broke and desperate, he had taken a loan out from the mob. The money paid off all of his bills, but now he had nothing left. His job barely paid him anything, and he spent what little money he had on lottery tickets. Nothing had paid off and now he found himself in the casino, hoping and praying that Lady Luck would finally smile on him.
He just had to win enough to pay off the mob. All he needed was ten grand. Easy enough, right?
He forced a laugh and sat down at his “lucky” machine. In the year and a half that he’d been living in Las Vegas, this specific machine was the reason he kept gambling. Every so often, he would walk away with an extra thousand or so in his pocket, but with every win there were losses. Only once had he gambled away everything, but even after recovering from bankruptcy, he still couldn’t stay away.
The difference between then and now was self-control. He would set a limit when he walked through those doors, and the second he reached it, he would get up and leave.
Cody smiled to himself as he started the ritual. He rubbed his hands together and placed them on the machine.
“I need it tonight more than ever,” he whispered to the machine. He had been on a streak of bad luck. Six nights now he’d walked away empty handed. As he sat down, he hoped seven would be his lucky number.
“Drink?”
Cody turned to the source of the smooth female voice behind him. The dark-skinned waitress in a similar latex outfit to the one he saw earlier stood behind him, her digital pad in her hand.
“Rum and coke,” he replied with a smile.
“Be right back,” the woman said with a nod. He waited for her to return before he slipped any money into the machine. Her tablet scanned his card and he pressed his thumb to the bright blue screen. With his identity verified, the woman handed him the ice cold drink and he took a sip as he inserted his card into the machine.
“Son of a bitch!” he yelled as he leaned back in the stained chair. His voice was barely audible in the cacophony of machines and chatter. He slouched, his arms falling to his sides as he eyed the screen in front of him. He was down to less than a dollar. Fortunately, it wasn’t all he had left.
Before arriving at the casino, he had taken money out of his bank account and stashed it away. That way, he wouldn’t gamble everything.
“I should’ve cashed out when I got to five grand,” he muttered to himself. “Half is better than nothing.” But now he didn’t even have that. Cody had only a thousand dollars to his name and he needed nine more to satisfy the mob.
There’s no other way. They’re going to fucking kill me. His eyes moved away from the blank screen to the ceiling. He sat there, silent and still, the cigarette smoke from the man sitting next to him filled his nostrils.
“Sir, are you done with this machine?”
He sat up and turned around. The security guard hovered behind him.
“Sir, if you’re not going to play, I’m going to have to ask you to leave.”
Cody looked away from the guard to the robot behind him. The chrome plated automaton carried an automatic weapon loaded with non-lethal rounds. It stared at him through eyes made of small LED lights.
“Yes, I’m done. I’ll be going now.” He sat up and rubbed his face. The slot machine spat out his empty card and Cody slid out of the chair. He nodded to the guard and staggered away, his hopes dashed and his fears realized.
On his way out of the casino, he spotted the vibrant movie poster advertising an upcoming superhero flick. Cody stopped and stared at the ad and his face lit up. An idea filled his head and the metaphorical light bulb shone bright.
Since there’s no way I can pay them off, I guess my only other option is to hide. Looks like Chelsea is going to have to visit for a while.
He drove back to his apartment in silence. His electric car made little noise, but the music from the casino was stuck in his head. Cody ignored the repetitive beats and thought about the plan, one so crazy that it just might work.
A week ago, he had received a message from the mob that told him the deadline to pay back the loan was tomorrow. He was supposed to meet the collector at a predetermined location at the set time. Cody recognized the address. It was a bar just outside the Strip—the same bar where he’d taken out the loan.
“I have just under twenty four hours to disappear,” he said to himself as he unlocked the door to his apartment with his thumb print and retinal scan. No one had followed him, but he still locked the door right behind him, just to be safe.
Cody held his breath as he waved his hand over the light switch. The lights flickered on and he let out a sigh of relief when he saw no signs of tampering. Of course, his apartment was cluttered to begin with, but there was a method to his madness.
Cody took off his clothes and tossed them onto the ground as he made his way to his bathroom. The lights automatically turned on when he entered and he inspected his arms and legs in the bright white light. He frowned. Most of his body hair had grown back since the last time he shaved. He had once read about a procedure that would permanently remove the hair follicles on his body, but shaving wasn’t a chore to him, and besides that, the procedure was expensive.
Behind him, cosmetics were strewn across the marble counter top and his favorite wig rested atop a mannequin’s head. The hairs that made up the wig were synthetic and colorless, but all it took were several drops of the desired dye and the strands became vibrant and lifelike.
The wig wasn’t the only thing that could change colors. He searched through the small glass vials until he found the one he was looking for.
The size of a nail polish bottle, Cody held up the eye drops to the light. The sticker on the front read “ice blue” and there was a picture of a glacier behind it. He shook the bottle next to his ear and smiled when he heard the sounds of liquid sloshing.
He considered the bright blue drops, but then he remembered that there was another color that he wanted to try out.
On the counter mixed in with the other free samples was an unopened bottle of eye color that he had almost forgotten all about. Cody looked away from the stash to the vanity mirror. He leaned forward and looked closely at his own eyes. They were a dark brown, rich like the color of forest soil. He set the bottle down and picked up the newly discovered one. The liquid contents were clear, just like every other one, but the label depicted an eye with a copper-brown color.
Returning the bottle to the makeup pile, he searched the drawers for the pink razor. Using sound waves, the razor painlessly removed what little hair had grown back on his arms and legs. It hummed liked a subwoofer when he turned it on.
As he shaved his legs, Cody’s mind drifted back to when he first started crossdressing. It all started with simple curiosity. In high school, the girls would often wear pantyhose or leggings in addition to skirts. At the dances, they would wear short dresses and high heels. He wondered what it felt like to wear those clothes, and as he surfed the internet looking for scantily clad women to masturbate to, his urge to wear the sexy lingerie that porn stars and adult models wore steadily grew.
He had no sisters, so the only women’s clothes he could wear were his mother’s. Unfortunately, none of the outfits he wanted to wear were in her closet. No high heels, stockings, or anything close to being sexy. His mother was a plain woman, and his parents were quiet, private people. They never went to parties, nor did they ever dress up. But one day, he received a pair of skin-colored pantyhose in the mail, addressed to his non-existent wife.
It was the package that changed his life.
The pantyhose caressed his skin and
he jerked himself off by rubbing his swollen dick though the silky hose. He screamed as he stained the pantyhose with his sticky white cum and the urge to crossdress became a fetish.
After dropping out of college at the beginning of his senior year, Cody had a falling out with his parents. He got in trouble too often, and they decided he was on his own.
Being kicked out of the house ended up being the best thing that ever happened to him. He bounced around from job to job until he finally settled in Las Vegas at the age of twenty-six, where he nabbed a job as a busboy at a casino restaurant. Most of the money he made went to bills and rent, and he saved a portion of what little he had left.
He used that money to purchase clothes, and now more than half his closet was filled with dresses, skirts, blouses, and coats. His dresser was stuffed with lingerie; bras and panties in an assortment of colors, plus stockings, garter belts, and two corsets. Cody owned several pairs of high heels, from simple pumps to platform heels, to thigh-high boots. Most of his feminine adventures remained in his apartment, and it was only in the last couple of months that he finally braved the outside world en femme.
Night after night leading up to the first outing he practiced his makeup. He tried out samples of all the different eye colors until he found one that he liked. The wig was the most expensive item. It would’ve been cheaper to buy one made with lesser quality hairs or one that already had a color, but Cody wanted to splurge.
With his eyes colored that icy blue and his hair a silvery blonde, he had dolled himself up to the best of his ability and visited a gay bar. He had no intention of walking away with a date for the night; he just wanted to mingle.
For a long time, the wig was the most expensive item he purchased, until one drunk night, after winning a thousand dollars at his favorite casino, Cody decided to buy a voice changer. It covered his Adam’s apple like a skin-colored bandage and it successfully gave him the voice of a woman. He was going to return it, but once he tried it out, he decided to keep it. That voice changer was going to come in handy now that he had a very good reason to hide his identity.