by John Dylena
“I hope she gave me the keys for these.” He bent over, pulled out the plug and walked over to his bathroom and tossed it into the sink. As he stood in the bathroom, he felt a warm stream of fluid come out of his asshole. He turned and saw the remainder of the cum flow. He reached for a tissue and cleaned it up.
“I hope that’s the last of that,” he said as he threw the tissue away.
He walked back into his bedroom, removed the bra, and tossed it onto his bed next to the panties. He felt up his body, looking for the seams of the fake breasts and the padding on his hips and butt. Finding one, he tugged at the material and peeled off the falsies like a band-aid.
“Damn good thing I’m completely shaved, otherwise this would’ve seriously hurt.” He tossed the fake breasts onto his bed and pulled off the silicone padding on his waist and butt.
Sean stood naked in his bedroom, still wearing the wig, makeup, jewelry, heels, and cage. Remembering the key ring, he walked back into his living room and dug through his purse. He sat down on the couch, testing all the keys on the cage. None worked, but he was able to remove the high heels.
“I guess this is part of the punishment,” he sighed, walking back into his bedroom.
He tossed the heels and wig onto his bed and returned to the bathroom. Despite the clock reading four-a.m., he climbed into the shower. The hot water washed the makeup off of his face and the stank of sex mixed with perfume from his body. For a long time, he just stood in the shower, letting the water flow. His mind retraced his steps, trying to remember what had happened.
The last thing I remember is waking up on the bench in the park. Before that… there’s nothing. The last thing I can remember before waking up is leaving the strip club. Between then and the taxi, it’s all black.
Cleaned and refreshed, he staggered out of the shower and quickly dried off before falling asleep on his bed, naked.
When he woke the next morning, the sun was shining brightly. His apartment was quiet and his body was sore. His manhood was still caged, but he ignored it.
He threw on a shirt and some shorts and sat in front of his TV the rest of the morning. He was at his kitchen table eating lunch when his doorbell rang.
Remembering Messandra saying something about a package, he eagerly got up and answered the door. A man in a uniform stood in his doorway with a large brown box.
“Package for you, sir,” the man said.
“Thank you,” Sean replied.
The man smiled and nodded as he backed away from the door. “Have a good day!” he said as he walked down the hallway.
Sean closed the door and opened the package as he walked toward his couch. Sitting down, he poured the contents onto the table in front of him. Inside was a pink trifold, his own wallet, a tiny key ring, a large tube of glue, a makeup box, and two DVDs. One of the DVDs was pink with the words ‘play me’ scribbled on them. The other was blank.
He set the items aside and opened his wallet. All his cash and cards were still in there. He opened the pink trifold and found a set of credit and debit cards identical to his own, plus an ID. The picture on the ID was a woman with blonde hair and blue eyes and a big, stupid grin.
Wait a second–that‘s me!
The photo was, in fact, him from the night before. The address on the ID was his own, except the name on the ID was “Serena Sweetlips.” All the cards in the pink billfold had “Serena Sweetlips” on them also. There was no cash, but a strip of paper.
Sean read the text on the paper aloud. “Sean, the cards in this trifold are clones of your own. They are all linked to your bank accounts. Don’t worry; I didn’t keep the information. You can use them next time Serena Sweetlips is out on the town!”
He laughed, putting the paper back in the trifold and tossed it onto the couch. He picked up the key ring with the tiny keys on them and used them to unlock his manhood. He tossed the cage aside and held the pink DVD in his hands. He walked over to his TV and inserted the disc into his player.
What Sean saw was security footage of a nondescript room. After a couple of seconds of inactivity, he saw the door to the room open and watched as three women brought in his body and put it on the table. He watched them shave and dress him. He watched them slide the plug into his butt and put his limp body in front of the screens. The only thing he could hear was his mumbling.
“Serena… air-headed bimbo…”
Sean covered his mouth in shock. The footage cut out after his body collapsed. After a couple of seconds of static, the picture returned. This time he was sitting on a bed talking to a woman. He listened to the words that came out of his mouth.
“I’m, like, an air-headed bimbo! Duh!”
He watched the woman leave and two large men enter the room. Then he watched as “Serena” eagerly got on her knees to pleasure the men.
Sean wanted to stop the video, or fast-forward, but he couldn’t. He was watching a train wreck, and he couldn’t tear his eyes away.
“Serena” passed out and the two men left. After a couple of seconds, the camera switched to a different view. The woman had the camera trained on her.
“Hello, Sean,” the woman said to the camera. “As you can see, you were submitted to a series of punishments,” she used air-quotes for the last word, “which is fitting, as you deserved to be punished.
“My name is Mistress Messandra. I am a professional dominatrix, and thus have a variety of resources at my disposal. You called me an air-headed bimbo. You should never insult strangers, especially when you don’t know what they’re capable of, so I taught you a lesson. Consider the clothes and pads a gift. For I know it would be a lie for you to say that you didn’t enjoy any of it.”
She was right. Sean quickly paused the video and rested his head in his hands. His mind went back to the cab ride and the payment the driver got from him. Not looking at the screen, he resumed the video.
“Included in the package is another DVD. On it are some goodies, as well as a single track. Listen to that track and Serena Sweetlips will reappear—only temporarily, as permanently turning you into a bimbo wouldn’t be as much fun. Au revoir!”
The video ended, and blackness filled the TV screen. Sean remained seated and stared blankly at the TV. Shock, confusion and fear filled his mind.
After some time, he stood up and went straight to the bedroom. He threw open the door and reached for the pink dress that was still on his bed. Sean held it in his hands, hell bent on destroying the items.
But he couldn’t. He just stood there, the dress in his hands, his fingers rubbing the soft fabric.
All his hatred and anger vanished. His plan to get rid of the items faded away, replaced by curiosity. The curiosity turned into longing, and after a couple of minutes, he made up his mind.
Sean set the dress down, removed his clothes, and reached for the tub of glue. He applied a thin layer to the silicone breasts and pads and placed them on his chest and hips. Once dry, he put on the bra and panties, zipped up the dress, slipped on the heels, and donned the wig. He dolled up his face with the makeup and decorated his body with the jewelry.
With the dress-up complete, he sat down at his computer, put on his headphones, played the track, and closed his eyes.
“My name is Serena, and I am an air-headed bimbo,” he giggled.
OFFICE ENTERTAINER
The air was thick and heavy in the club. It was hazy; a sticky mixture of heat, sweat, smoke, and sex. The room was dimly lit, the only lights were the stream of round bulbs that lined the raised platforms were the dancers danced. The music was loud and deep, its pulsating rhythms guiding the dancers in their movements. Their hips swayed and their bodies gyrated to the beats and tempos.
The crowd had their eyes on the dancers, either up on one of the many stages or on their laps. Bouncers casually walked the floor, their eyes on the patrons waiting to spring into action at a moment’s notice. The booths were dimly lit, making it near impossible to make out the features of those sitting in the next bo
oth over. Only when a dancer mounted a patron did the lighting shift, illuminating the lap dance.
Devin sat alone in one of the booths. His hands cradled a tall pint of cold beer and his eyes moved about the club. His gaze would linger on one of the dancers and would trace her curves from head to toe before moving on to the next one.
One of the waitresses moved into his line of sight and remained there. One arm held a round tray tucked under her shoulder, the other rested on her cocked-out hip. She had brown hair pulled back in a messy ponytail with green eyes and tan skin. Her outfit was a black cut-off t-shirt and miniskirt, stockings and heels.
She smirked. “Why hello Devin! Didn’t know you were coming in tonight.” She took her hand off of her hip and placed it on the table as she leaned forward. “Don’t you usually come in on Friday’s?”
Devin’s eyes went from hers down to her breasts briefly. He blushed. “Hi Jessica.”
Her smirk widened into a mischievous smile and Devin shriveled up under her gaze. She knew why he was here tonight. He knew that she knew. Tonight was a special night. A night that happens only once a month at this club.
Last month, Devin was too nervous to partake in the special night. He just sat in the back and watched with a mixture of jealousy and fear as a handful of men worked the stage and the poles dressed as women. Only, they made no attempt to hide their manhood. At first their cocks were neatly tucked away in their panties, the bulges were obvious and as they danced and feasted off of the palpable lust of the crowd that hooted and hollered and stuffed bills into their clothes, their cocks grew hard.
Devin watched with awe as the dancers moved with rock-hard erections. Some of them had breast forms, others chose to remain flat-chested. No matter which option they chose, all the dancers were convincingly feminine with expertly applied makeup and wigs. They all walked away with some serious cash. Even though Devin had a nice job and made a good amount of money, he could always use a little extra spending cash. His computer had some obsolete parts and the money he could make from going up and dancing would not only pay for replacements, but he would still have some left over.
He started visiting the club more often, becoming a regular. He studied the dancers, their movements and techniques. He saw how they manipulated the crowd and catered to the big spenders. If he was to not only compete with other dancers, but to make some money doing so, Devin would have to really develop some skills.
It was nerve wracking, opening that very first package. He bought the items the same night. Devin stayed up well past his normal bed time that night browsing online for some clothes and shoes. Nothing was provided. The box was waiting for him in the office at his apartment complex. He was extremely nervous when he ordered the items, even though he knew the contents would be masked by the Amazon logo. Devin said nothing as he grabbed the box and ran to his apartment after work that day.
His fingers trembled as he tore open the box and removed the contents onto his round kitchen table. There was a bright, almost neon, pink wig, some stockings, panties, bras, a minidress, microskirt and tied-off blouse. Lastly were the shoes: a pair of six inch, clear platform strappy heels. In addition to the clothes and wig, there was some costume jewelry and a basic makeup kit. The jewelry was clip-on earrings, some bracelets a body chain and even a clip-on belly button piercing.
Devin was thin, but he wasn’t girly. He had an almost athletic build with some muscle tone. He had brown hair and eyes, little body hair and almost no scruff. His attempts at growing facial hair would be rewarded with a borderline-creepy mustache, some chin hair and patchy growth on his cheeks. After several failed attempts during high school and college, Devin decided it was never meant to be and shaved every morning.
An overwhelming fear washed over him as he stared at the items on the kitchen table in his apartment. Never before in his life had he ever worn women’s clothing, yet after one night of watching men dressed as women strip and dance—which he didn’t realize was scheduled for that night—he returned home with the full intention to do so the following month and even bought the clothes. The realization of what he done didn’t sink in until this very moment, the package arrived and his purchases there in front of him.
He stood up and backed away from his table, rubbing his face and mumbling to himself. Devin paced about his apartment, eyes occasionally darting to his kitchen table then looking away as if he gazed upon something forbidden and taboo. He felt ashamed and confused, yet turned on and excited. There was a growing fascination welling up inside him as he remembered the men up on that stage and how convincingly feminine they were—even with their cocks exposed and their lack of breasts.
Devin remembered how turned on he was.
His body remembered first, his cock hardening slightly in his jeans as he moved into the kitchen toward the fridge. It caused him to stop mid-stride and look down at the growing bulge. A warmth followed, which burned hotter as the memories came into his mind’s eye. He remembered the rush when he imagined what it must be like to look that sexy; to be up on that stage and in the eyes of the crowd, your only job to arouse and entertain.
There was one dancer in particular that Devin remembered vividly, mostly because near the end of the man’s dance, Devin could’ve sworn he saw precum drip out of the man’s cock. The man was stunningly beautiful, even though he chose to not wear forms. His body was thin and feminine, he had curves and an ass; legs that made Devin drool and piercing eyes. That dancer could’ve made even the most straight guy question his sexuality.
It made Devin question his.
It’s not that Devin never before in his life had a gay moment, in fact in college he had a one night stand with another guy. They were both drunk and hooked up after a party. When they both sobered up in the morning, they both admitted to the other that they weren’t actually gay, that they only really had a curiosity. Devin had a couple girlfriends since, and while he was open to dating another guy, he just never found one that he could see himself in a relationship with.
Seeing that man dressed convincingly as a woman made Devin wonder what it would be like to be on the other end of that. To be the feminine male that makes both women and men horny and lustful. He wondered what it would be like to date another guy—or woman—dressed as a woman. Devin had a submissive nature, something which one of his ex-girlfriends cultivated further after a couple nights of attempted kinky sex. His ex didn’t like it as much as she thought she word, Devin on the other hand, loved it.
Devin stood in the kitchen next to the refrigerator drinking his beer with his eyes locked on the table. His mind raced, debating between sending all the items back or following through with his plan. He was in such deep thought, that he didn’t realize his beer was empty until he held it up to his lips for almost thirty seconds.
He tossed the bottle in the recycling as he walked out of the kitchen past the table and toward his bedroom. He stopped when he spotted his computer and remembered why he decided to do this in the first place.
Spending money, he thought. But is it really worth it?
He tried to sit at his computer and play some video games, but it wasn’t long before he was reminded of his sub-optimal system; the slow load times, the laggy game play, the ugly, gray-ed out environments.
Devin let out a heavy sigh and turned off his computer after only ten minutes of gaming. He leaned back in his chair and looked up at the ceiling.
He was lost in thought for who knows how long. It was the beeping of his phone that brought him back to reality. He had gotten a text from his boss.
Anna was really something. She was tall—well, Devin was in actuality shorter than average—beautiful and smart. She had dark brown hair and beautiful blue eyes. Older than him by almost ten years yet she barely looked a year older than he. Her skin was soft and smooth, blemish free and lightly tan. As beautiful as she was, she was also fierce and strict, ruthless but occasionally light-hearted and funny.
She had a wit sharper than a blade, and co
mbined with the rest of her assets, made her a formidable corporate powerhouse. She rose quickly and with her at the helm, steered the company into success and profit.
She was telling him to come in tomorrow.
Devin threw his head back and groaned, tossing his phone onto the bed. He hated coming in on Saturdays. Then again, he would be getting overtime for it.
He walked back out into the kitchen and after staring at the items for a few minutes, decided to follow through with the plan.
He took the clothes back into his bedroom and tried them on one by one.
The bras had big empty cups and were tricky to put on. The panties he got in three different types: thong, bikini, and boyshort. Devin blushed as he put them on and looked at his reflection in the mirror. He tried to keep his cock tucked in. The more he played with it, the harder he became.
The harder he became, the more aroused he was.
Devin bit his lip as he looked at his reflection. There, standing before him was a guy in a pair of hot pink panties with his cock poking out of the top. He placed his hands on his belly and they slowly slid toward his now throbbing cock. He tilted his head back as he gently rubbed the underside of his cock through the thin, delicate fabric of his new panties.
His phone buzzed again.
Devin shook his head and walked over to his bed. Another text from Anna. He still needed to come in, only it would be an hour later.
Devin sighed as he quickly typed a response and tossed his phone back on his bed.
He looked back at his mirror, down at his now mostly flaccid dick, then at the bed.
He still had several more items to try on.
Keeping the hot pink panties on, Devin pulled on a pair of white fishnet stockings with a scalloped lace top. A strip of silicone lined the inside of the lace, making it so that they would stay up on his legs.
Devin frowned at his legs. Despite how sexy they looked and how strangely comfortable and arousing the stockings were, the image was ultimately tarnished by the hairs on his legs poking though. If he was going to go through with this, he would have to be completely smooth.