by John Dylena
Completely.
He frowned. Never once in his life had he shaved his body. From the neck down he was covered, but fortunately the hair was thin and sparse. Unlike his brother who he jokingly called the wolf man.
Shaving would come later, he decided. Trying to ignore the growing arousal at the thought of being as silky smooth as his ex girlfriends, Devin put on some more of the other clothes.
He put the matching pink bra back on and on top of that he donned a white fishnet top. He put the shimmering pink wig on and then lastly put on the heels.
He fumbled with the tiny buckles that wrapped around his ankles, then wobbled as if walking on stilts as he stepped in front of the mirror. Devin hadn’t had this much trouble keeping balance since he tried to surf one summer while his family rented a beach house.
“Holy shit how do they do it?!” He thought aloud, looking at his reflection and down at his own feet.
When he finally gained some semblance of balance, Devin turned his body to look at his profile. His legs looked amazing—even with the hair—and the platform stripper heels boosted his ass just enough to be noticeable. The heels forced him to stand out straight and push his chest out.
Devin was pleased with his look. There was some inherent femininity, and with some work, he could look convincingly female.
Satisfied, he turned back toward his bed to strip, only he stopped mid-stride. He was still very aroused and his cock was rock hard and held against his belly by the waistband of his panties.
An idea came into his head. An idea that latched on and couldn’t shake free. He turned back toward the mirror and took a deep breath.
Biting his lip, he rubbed his body as he slowly moved his body, trying to mimic some of the movements he’d see the strippers do.
His body got hotter and hotter as he danced. Devin let his mouth hang open a little bit, moaning even as he bounced and gyrated.
“Oh fuck yes,” he moaned, closing his eyes. When he opened them he discovered that his hands were around his cock and slowly stroking.
He didn’t stop himself.
Instead, he stared at his reflection and watched the girly boy jerk herself off and moan. It felt so strange, so surreal.
His hand moved faster and faster. His hips buckled and he moaned loudly as cum shot out of his dick onto the mirror and floor.
It kept coming.
Strings of hot, sticky cum shout out. Devin wobbled in his heels, barely keeping balance as the orgasm washed over him. His head swam and his eyes fogged over as the most intense orgasm he has ever had came to an end.
Devin’s heart pounded. For several long seconds he just stood there staring blankly at his reflection. He blinked, then looked down at his hands in disbelief. It felt like a dream. Like he woke up to find someone had taken control of his body while he slumbered then came to just as the intruder finished.
But it wasn’t a dream. No one took control of his body. It was all him. This terrified him, but just as much, it filled him with curiosity and awe. These new feelings and desires were wonderful. Never had he felt so good, so sexy; never had he had such a powerful orgasm from masturbation. Would it always feel this way? Would he be able to control himself up on the stage?
Even though he would be fully exposing himself, if he ejaculated while on stage, he would face some severe consequences.
Even if he didn’t go up and dance, he needed to do this again. But first: he needed to clean up the strings of cum on the mirror and floor.
Almost every day after work, Devin would come home and practice. It became more than just trying to be good at stripping for the extra cash. He found pleasure in it. There was something about it that just made him feel so good. He ended up buying an assortment of additional clothes, from various “costumes” to items he can mix and match; still only having one pair of heels.
He didn’t wait to shave either. After work that Saturday, he stopped at a store on the way home and bought some razors and shaving cream, and after a long, hot bath he went to work on removing his body hair. It was an arduous task, one that he walked away from with more than a few nicks and cuts.
The result was surreal.
For almost an hour, Devin just sat on his bed and gently stroked his legs. The smoothness was foreign, erotic. There was an awkwardness when he put on pants and a shirt. The way the fabric rubbed his skin was strange. It took some getting used to, the hardest part he realized was the fact that his arms were visible. What if someone said something to him at work? What would he say to defend shaving his arms?
But no one said anything that Monday. Then he just stopped worrying about it.
It almost became a ritual. On the days where Devin didn’t go to the gym, he would come back to his apartment, change out of his work clothes and put on one of his now many stripper outfits. Every day he tried a different combination until he found one he liked. Then he would sit down at his vanity and practice putting on makeup. On the weekends he would paint his nails.
Once he was dressed, he would walk about his apartment in the clear platform heels. Devin would exaggerate his stride, sway his hips side to side; walk one foot in front of the other with his arms to the side and his chest up and out. It was difficult at first walking in the high heels, many times he would stumble and occasionally fall. But the more Devin practiced, the easier and more natural his movements became.
There were some evenings where he spent the entire rest of the day dressed. Almost immediately when he got home he would change out of his clothes and into one of his stripper outfits. It was almost like a switch. The moment he finished getting ready, he became some other person. Not Devin, but a woman. A flat-chested woman with some bonus parts. He did by a pair of false breasts, and there was one night where he not only glued them to his chest, but he even debated going out in public. The moment was fleeting, and in the end he decided to stay indoors and practice his moves.
On Friday nights he would visit the strip club and sit in the same booth. Not only because it gave him a good view of the stage, but also because it was a part of Jessica’s route. She was friendly—though he wasn’t sure if she was genuinely friendly or just doing it for the tips—and nice. She told him about the girls up on the stage and how for a short time she danced too, until she had (as she put it) a “career ending injury”. She couldn’t dance anymore, but she could still wait tables.
When the night finally came, Devin was a nervous wreck. He practiced his movements many times the night before so while he knew he was ready, he was still scared as hell. All night that night he surveyed the crowd. The second he saw someone he knew, he would hit the big red cancel button. No way in hell was he going to go up on the stage if he was going to be recognized.
The first half of the night was a regular night. The ladies danced, Devin watched. He didn’t know that Jessica also worked Wednesday nights.
“No… you’re shitting me,” she laughed. She immediately stopped when she saw him sink further into the booth. He looked very much afraid and anxious. “Oh, shit. You really are going to do it?”
“Yeah,” he replied, his voice barely audible.
Jessica watched him reach out and grab his small duffel bag and push it under the table. She looked around real quick then signaled to one of the other waitresses. “Oi! Becca! Cover me for a sec okay?”
She didn’t even wait for a response from her coworker. She sat down in the booth and scooted over next to Devin. “Hey, I think it’s awesome that you’re going to do this. It’s very brave of you and I am actually super excited to see you do it.”
Devin felt a lot better. She put her hand on his shoulder and rubbed it. “Tell you what, how about I take my break and walk you backstage? The other guys will be heading back there now, so if you’re going to do it, now is the time.”
Jessica stood up and extended her hand. Devin hesitated. He took several deep breaths.
“Come on Devin, live a little,” she said with a wink.
Devin took her
hand and followed her backstage.
“Wow! Killer job with your makeup!” Jessica said returning backstage. After taking him here initially, she gave him a little pep talk then had to return to the club floor. She promised that she’d be rooting for him before giving him a quick kiss on the cheek and leaving him to get dressed with the other men. They were in various stages of getting ready, and they all gave Devin cold, competitive stares. He watched them as they sized him up, one even letting out a little chuckle.
Devin smirked then got dressed. He was still nervous and afraid, but it had moved to the back. A new feeling had taken over. These other guys weren’t just fellow dancers, they were his competition. They were all fighting for the same thing: the love and attention—and money—from the crowd. Whoever was picked as crowd favorite would go home with the bonus pot, in addition to the tips he earned.
There were three other dancers in addition to Devin. Four dancers for three poles. No one was allowed to hog a pole, but Devin had prepared for that situation anyway. The announcer called out their names, and Devin took a deep breath before following the other three out.
When he finally returned backstage, it was with the bedazzled rhinestone tiara on his head, a couple hundred dollars in tips, and a six-hundred dollar prize. Some of that money was Jessica’s. She more than happily slipped a bill into his g-string when he squatted down in front of her and stuck out his ass like he had seen the other dancers do.
The other guys were jealous and upset, one of them—the guy who had the crown last month—said somethings that cut, but Devin just ignored him. It helped that Jessica was there when he said the things. She chewed him out more than Devin ever could. She gave him a hug before saying goodbye. The other guys had already left and Devin changed back in the quiet of the locker room.
He was glowing when he walked into his apartment. He was grinning like an idiot as he showered the sweat, makeup, and body glitter off. He was still smiling when he climbed into bed.
Then everything changed when he walked into work the following morning.
For close to an hour, it was like any other workday. Devin would arrive when he normally did, and grab some coffee and perhaps a donut or muffin in the break room if there were any. He’d enjoy the mini breakfast in the few minutes he had, as he tended to arrive ten or so minutes early. From there he would smile and greet his coworkers as he made his way to his desk. He would turn on the computer, clock in, and begin his day.
It was like any other day. Devin sorted through some emails, work on some reports, maybe sneak onto his phone for a few minutes.
“Devin.”
Anna’s voice chimed in on the intercom on his phone. He hesitated for a moment, thinking he was caught browsing on his phone.
“Yes?” He said, picking up the phone.
“You busy at this moment?” Her tone was serious, professional. It was all he’s ever known about her. Anna’s always already there when he gets to work in the morning, and she’s always the last one to leave. She isn’t rude; she’ll say “good morning”, even make small talk on the rare occasion. It happened once to Devin, on one of the Saturday mornings that she had him come in on. It was just the two of them, and once they got things covered, they had some down time and they just started chatting. She wasn’t awkward or cold, in fact, she kept the conversation going and kept it interesting. Until they had to get back to work.
“No, I’m free.”
“Good. Come by my office. There is something we need to discuss.”
She hung up. Devin thought for a moment. He traced his steps back and tried to figure out if there was something work-related that he missed. Nothing was late or overdue, he had no major projects. He had been performing well, though.
He smiled. Maybe Anna was going to offer a promotion or raise. It had been a while since anyone got any kind of reward, other than the usual year-end bonuses. Not once did it occur to him that Anna wanted to discuss something not work related. She never discussed things that weren’t related to work, even when someone managed to get some small talk, she kept things vague and short. The most anyone knew was her age, that she had two younger siblings, and is apparently single.
It was still early, so a bulk of the workforce hadn’t arrived yet. Devin gets there early so he could leave early. He figures Anna just sleeps here. That she has one of those foldaway beds in her office somewhere and a closet too. Her office was big enough for it and she did have a couch.
“Close the door and have a seat.”
Devin nodded and as he sat, Anna pushed a button on her desk that turned the blinds, blocking the view to the office. When he looked back at her after taking a glance at the blinds, Devin’s heart sank.
She was grinning.
It wasn’t a normal smile, one that meant she had very good news to share with him. It was a mischievous smile. She knew something that pleased her greatly. It was at that moment that Devin realized what it was that had Anna grinning like The Joker from Batman. His fears were realized moments later when she brought out her phone and handed it to him.
On the screen were pictures of him stripping.
The color from his face vanished and he was as still as a statue. Anna walked around her large, polished wood desk and took the phone from Devin. She set it aside as she sat on the edge and crossed her legs.
“Devin,” she paused. “Devin, look at me.”
Her voice wasn’t harsh or cruel, nor was it mocking. It was motherly. She sounded exactly like his mother when she caught him misbehaving. He was sure the next words out of her mouth would be “you’re fired.”
He was right… sort of.
“You’re not fired,” Anna said. She picked up her phone again and swiped through the pictures. She looked very pleased. “You make such a pretty girl. I couldn’t believe that it was you up on that stage. Now I see why you have no hair on your arms.”
Devin blushed and her comment made him try to hide his arms out of embarrassment.
“You moved so gracefully, so sexually. It really turned me on.”
Devin’s eyes widened but he kept his gaze on the ground between them.
“That was your first time doing it, yes? You weren’t up there last month if I recall correctly.”
“Yes, ma’am.” Devin replied weakly. He was so embarrassed. He made fists with his hands and squeezed so tightly his knuckles turned white. Then he released them and fidgeted. He tried to keep his gaze away from his boss. He looked at the ground between them, at his lap, over at the door to her office. Anything but her.
“Devin, look at me.”
He slowly raised his head and his gaze. He wanted to look away from her as if she was Medusa and he would be turned to stone upon laying eyes on her. He followed her body up to her face. His eyes glanced over her stiletto pumps, her legs encased in nylons, the black pin-striped skirt that rode up on her thighs. She spread her legs as his eyes traveled up her body.
She was wearing stockings. Devin swallowed hard and his face turned bright red when he laid his eyes on the lacy tops and the thin straps that disappeared further up her skirt. He could barely make out her panties in the darkness. They were red lace.
There was something else there. Something that he wasn’t quite sure of and decided it was just his eyes playing tricks on him.
As briefly as she opened her legs, she closed them again and Devin lifted his gaze to her eyes. Anna had one eyebrow arched and the corner of her dark red lips was curved into a satisfied smirk.
“Devin, how would you like a promotion?”
He opened his mouth to speak, but no words came out. He closed his mouth, blinked a couple times then opened again. “What?”
Anna uncrossed her legs and recrossed them. “A promotion.” She showed no signs of annoyance or impatience. A true professional.
“What is the job?”
“My personal assistant. But in order to get the job, you have to pass the exam.” Her smile widened. “Your pay will be significantly improve
d, and you’ll get full benefits, plus… more.”
“What… what will I have to do?”
“Dance.” She slid off the desk and sauntered toward him. She exaggerated the movements of her hips and hiked up her skirt. “I want you to move like you did up on that stage last night. Except you won’t be doing it for a crowd, you’ll be doing it for me.”
She continued pulling up her skirt. The tops of her stockings and the garters that held them up were fully exposed. Devin’s heart beat faster and faster. His body grew warm and he squeezed the armrests of the chair. He squirmed as his cock hardened in his pants.
Then he saw it.
“And when you’re done dancing me and getting me all hot and bothered, you’ll pleasure me.”
Anna pulled her skirt up over her red lace panties. Devin was expecting a normal woman’s crotch. If anything, he would’ve been surprised if there was some hair down there. But what he got something completely unexpected.
A cock.
There it was, tucked away in her panties in such a way that no one would ever suspect that Anna had something extra. Devin was frozen in shock. He just sat there and stared at it as she hooked her fingers into the waist band of her panties and pulled them down as he had seen the strippers do on stage. She let it hang there for a few moments before pulling her panties back up and letting her skirt fall.
She straightened out her skirt as she backed away from Devin and leaned against her desk. “Did I make myself clear?”
Devin stared blankly ahead. “Yes ma’am.”
“Then return here tonight at midnight and bring whatever outfit you think will satisfy me the most. I’ll wait for you in the parking lot.” She walked behind her desk and sat back down. “You may get back to work.”
She pushed a button on her desk and the blinds opened. Devin stood and walked out of the office. He tried to not show the fear, confusion, and sheer arousal on his face. He also didn’t want it to look like he was just fired. To anyone who asked, he just told them it was a simple meeting, and that she had more work she wanted him to do.
