by John Dylena
Devin couldn’t focus. He tried to work and eventually sunk into automation. Time just passed by. He drove home in silence and sat quietly in his apartment. He just laid on his bed unsure of what to do.
He wondered what would happen if he didn’t show up to the meeting tonight. Would Anna make public the knowledge of his stripping and crossdressing? Or would she just keep it to herself and try to find ways to get him to strip and dress up for her.
On the other hand, the pay increase would be really awesome. The perks too.
“I’ll do it,” he said aloud, as if Anna was in the room with him.
Devin got up off of the bed, laid out all of his girls on the bed, and put together an outfit.
There was only one other car in the parking lot. Devin parked his car next to it. Anna didn’t even get out. She just rolled down her window.
“Get in.”
“But—”
“Get in. I’m taking you somewhere else.” She rolled her window back up as Devin climbed in the front seat, his duffel bag on his lap.
They drove in silence. Anna was still in her work clothes: white satin blouse, black pin-striped skirt, dark stockings, and black patent heels. She drove with her heels on, speeding out of the parking lot and down the street. She was fast, but she wasn’t reckless. Anna exhibited great control behind the wheel, efficiently navigating the empty streets until they pulled into a parking lot behind several buildings.
“Where are w—”
“Hush,” Anne said, slinging her purse over her shoulder and heading toward a heavy metal door illuminated by a single yellow light. Devin stayed close to her, occasionally looking around as they walked up to the door. She pulled her keys out and unlocked it.
The door led to a narrow hallway and three steps in Devin realized exactly where they were. Anna had taken him back to the strip club.
“What are we doing here? We’re going to get in trouble!”
“Nonsense. I know the owner. I have a key.”
She led him to the locker room.
“Get dressed. When you’re done, I’ll be waiting for you in the executive room. Don’t take too long.”
Anna went out through the dancer’s exit. Devin could hear the sounds of lights coming on and then the muffled sounds of music. He looked around the locker room and turned on the lights for one of the empty vanities. He unzipped his bag and got dressed.
Anna sat in the executive room as she has done several times before. The perks of both knowing the owner of the club and actually having the money to pay for it. She leaned back in the wide, comfortable chair, her legs spread apart and her eyes on the door. In one hand she held a short, fat glass with her drink of choice, the other rested on the arm rest.
There was music playing and the lights were on their preprogrammed circuit, alternating and changing with the beat of the song. She tapped her fingers while she waited.
Then the door opened and Devin entered the booth.
“Holy. Shit.” Anna said, smiling from ear to ear.
Devin blushed, his cheeks turning as red as Anna’s panties. He had on a blonde wig, white tied off blouse, a gray pin-striped skirt so short it barely covered his ass, dark stockings attached to a garter belt hidden somewhere under that skirt, a red thong with straps that poked out from his skirt onto his hips and matching red platform pumps.
He had bought the heels only last week, when he realized just how much fun he had dressing up. He no longer wanted to just dress like a stripper, he wanted to simply dress up, even if all of the outfits were rather risqué and shouldn’t be worn in public—unless you’re a woman in a certain profession.
His nails and lips were painted the same color red as the thong and heels, and dark eye shadow enhanced his eyes. Devin had on a pearl necklace that more closely resembled a choker and large gold hoop earrings.
“I… I hope you like my outfit.”
“Slut, I love it! Get over here and dance for me.”
“Yes, ma’am!”
Devin wasn’t quite sure what to do next. His body froze for a few moments when he laid his eyes on Anna. She had her gaze fixed on him. It was a predatory gaze, the one a lion gives to a trapped gazelle. It told Devin that he had nowhere to go. He was trapped and that Anna would have her way with him.
He swallowed hard. He wasn’t quite sure how to take this situation. On one hand he was incredibly turned on by all of this; the crossdressing, the stripping, submitting to his boss—not to mention the fact that she had a cock. On the other hand…
At that moment Devin realized that there wasn’t a downside to this. He wasn’t getting blackmailed, he wasn’t being forced to do any of this. He chose to do it all.
Anna knew that he knew this and she grinned and spread her legs.
“Come on Devin, dance for me,” she said in a calm, but commanding voice.
He bowed slightly, then sauntered over to her has he had seen the lap dancers do. He also climbed onto her lap in the same manner, placing his hands on her shoulders and straddling her hips. He kept his eyes on hers and she stared up at him with a look of victory. He tried to ignore the growing bulge underneath her skirt. He tried to ignore his hardening cock, even as it easily pushed down the small patch of fabric on the front of his thong and lifted up the front of tiny pin-striped miniskirt.
“Enjoying this, are we?” She purred. She took a sip of her drink and caressed his balls with her other hand.
Devin moaned as he rolled his hips around to the music, gently squeezing her shoulders as he moved in closer to her. His cock twitched from her touch, and she giggled as little dollops of shiny clear precum oozed out of his tip.
She hiked up her own skirt, bunching it up at her waist to expose her own panties and cock. It was bigger than this. Thicker. Longer. Juicier. He wondered what it tasted like. He wondered what it was like to be on his knees in front of her, his lips around that thick cock of hers.
He leaned forward, brought his hand down to her dick and kissed her as he gently stroked it. It was strange handling a cock attached to a woman, but he handled it just like how he handled his own.
“Eager little slut aren’t you?” Anna said in between kisses. She reached down and gently squeezed his balls, causing him to moan. “I want that ass of yours.”
Devin straightened up and turned around. He put his hands on his hips and looked back at her over his shoulder as he bobbed and swayed, squatted and stuck his ass out at her. He let out a little yelp when she playfully smacked his ass.
“Look at that cute ass of yours. So round, so pretty.” She squeezed it with both hands then quickly grabbed onto his hips and pulled him onto her lap.
Devin didn’t break stride. He put her hands on her thighs and grinded his ass against her cock. It felt strangely wonderful. His own cock was stiff as a board and more precum oozed out as he rubbed his girly ass against Anna’s dick.
“Oh fuck I want that cute ass of yours!” Anna groaned.
Devin turned up the dial on his movements, grinding against her faster and harder. He wanted her too. He wanted her more than she wanted him. He tried not to show how hot he was for her, but he failed.
His face was as red as tomatoes and he bit his lip as he looked back at her. He nodded meekly.
“There’s a bottle of lube in my purse,” she said pointing to her black leather designer purse.
Devin walked over to it and found the bottle right away. It didn’t bother him that she had obviously planned for this to happened. In the back of his mind, he wanted it to.
It was a pink bottle and the thick liquid inside it was clear. He squeezed a good amount onto his hands and set the bottle on the small table next to the chair. He stood in front of her, hip cocked out to the side with a smirk on his face as he rubbed his hands together, spreading the lube onto this palms before kneeling in front of her.
He kept his eyes on her cock as he coated it with lube with both hands, slathering the thick gel onto every inch of it.
When it w
as thoroughly coated, he wiped this hands off and with his eyes locked on Anna’s, he straddled her legs, pulled aside the thin strap of his thong, and lowered himself onto her.
“Oh fuck!” He moaned, as the pleasure filled him.
Anna grunted and grinned as she took his hips in her hands and guided him further down. Slowly and carefully, he took more and more of her dick in him until it all vanished inside of him.
“God that feels good,” she said. “Your pussy is so tight. It’s delectable.”
“It feels amazing,” he said, still getting used to the fullness.
“Well don’t stop now,” she said, smacking his ass. Ride that cock like a cowgirl.”
Devin tipped his imaginary hat at her then gyrated his hips.
He stopped referencing his stripper knowledge, and moved on to what he’d seen in porn.
He leaned forward and kissed her again, and she squeezed and smacked his ass as he bounded on her thick cock. It felt so good and he mentally cursed himself for not buying a dildo before. The thought had came into his mind in the month that he practiced his stripping and dancing, but he just couldn’t bring himself to actually buy the sex toy.
Now, he didn’t need it. Not when he had the real deal. Even better that it belonged to the beauty that is his boss.
“You want to cum, don’t you slut?” she said, tracing the head of his cock with her finger.
“Y-Yes, ma’am!” He replied, still bouncing and grinding.
“Turn around.”
With her cock still in him, Devin rotated one hundred and eighty degrees. Anna sat up and hugged his body. Her breasts pressed against his back and she brought her lips to his ear.
“If you can make me cum, you’ll get the job. Then I’ll let you cum.”
Devin wiggled his butt and pushed back against her. Whatever he was doing was working. Anna moaned and groaned and soon enough, he felt her cock twitch and his eyes widened and he felt her explode inside him.
“Oh yes! Yes!” she screamed as her cum filled him.
She was still pumping him full when she wrapped her hand around his dick and jerked him off.
Devin didn’t last long with the combination of her dick and cum filling him, and her hand stroking him. The pleasure washed over him like a tsunami and his eyes rolled back into his head as he swam in erotic bliss.
Cum oozed out of his dick, coating it, Anna’s hand and the floor in front of them.
He was still in a daze when she released his softening cock and brought her hand to his mouth. He instinctively licked and cleaned the cum off of her hand and fingers, savoring the warm, salty taste.
She helped him off of her, and cum dripped out of his ass when she pulled out of him. Devin stood there, his knees wobbling as her ejaculate dripped down his legs.
“Bend over,” she said.
He did, and he felt her slide a plug up into his ass. The flared tip kept it and her cum lodged in him.
She grabbed a couple of the cleaning wipes and wiped his legs and ass clean. Then she cleaned off her own body and tidied herself up. She shut down the booth and escorted Devin back to the locker.
“No, you’re staying dressed like that.” She said as he reached for his clothes.
Devin whimpered, but didn’t disobey. He put his clothes in his duffel bag, and followed her out of the back door of the strip club and into the cold night air, still dressed as a stripper.
“When you return to your apartment, you may change out of those clothes and remove the plug.” She said as they drove back to the office. “Tomorrow you’ll begin as my assistant. You can arrive at the time your normally do only…”
She turned toward him and smiled.
“You must wear that thong, garter belt, and stockings under those clothes of yours.”
Devin opened his mouth to protest, but stopped. All he could do was blush and say: “Yes, ma’am.”
“That’s my girl,” Anna said, speeding off into the night, her hand caressing Devin’s thigh.
TORN APART PART 1:
SPRING CLEANING
Brian rubbed his face with his hands and groaned. “No! No… this can’t be happening!” He sat on the edge of the couch and stared at the TV, hoping, praying—begging, even—that there was some kind of mistake and the call would get reversed.
But much to his dismay it was clear that his team had lost, and because of it, he had lost the bet with Lee, his roommate.
Lee, on the other hand, was ecstatic. His team was the underdog in all of this, and not only had he placed a bet with Brian, but he also had money riding on this game. He had correctly guessed the score and came out of this five thousand dollars richer.
“Yes! I guess this fucking apartment is finally going to get cleaned,” Lee cheered as he finished off his beer. He crumpled up the can and tossed it toward the recycle bin. It landed on top of the overflowing bin and rolled off onto the ground next to the handful of others.
Brian and Lee had been best friends since they’d first met in high school. They’d got along swimmingly despite their different looks, personalities and tastes. Lee was a typical jock. He was tall, strong, and had a great body, which he maintained by working out every single day. He was a smooth talker and had no shortage of ladies.
Brian, on the other hand, was almost the opposite. He was thin, scrawny, and introverted. He was a geek who often hung out in his room working on his computer or playing games. He was shy, and despite Lee’s many attempts, he had yet to go on more than one date with a girl.
He always blamed it on the type of girls Lee hooked him up with. Lee was a partier, something he picked up while in a frat at college, and even some three years after they’d both graduated, Lee still loved to throw house parties. The women that Lee hooked Brian up with were the same ones that went to his parties: loud, slutty party girls who were looking for a hook up rather than a relationship, especially with a nerdy, shy guy like Brian.
No, the only woman he ever wanted was Leah, and she was Lee’s girlfriend. She was different from all of the other girls that Lee knew and dated. She was smart, confident, funny, witty, and most of all, geeky. Brian had the chance to go out with her before Lee started dating her, but something had happened on that night and he couldn’t make it to the date.
A couple nights later, Lee came home and introduced his new girlfriend to Brian. When Leah walked through the door, he just sighed and returned to his room. Try as he might, Lee couldn’t get him to come out and for days. Brian wallowed until he finally accepted it and just chose to ignore it.
It was always awkward whenever she came by. Brian simply avoided her, choosing not to talk to her when she hung out or saying as little as possible when he had no other choice but to chat.
After three months of dating, she had finally gotten the hint and communication between the two of them had all but stopped. Lee didn’t care. He and Leah were happy and the sex was great. He had all but given up on Brian as well and no longer tried to hook him up.
Now Brian sat on the edge of the couch, a pit in his stomach and all hope lost. I can’t believe it. I… I lost, and now I have to go through with it. I have to—
“Oh, I cannot wait to see this. You dressed up head to toe like French maid, cleaning every inch of this place.” Lee laughed as he headed toward the kitchen, returning moments later with another cold beer. “Sexy lingerie, high heels, wig, makeup and all!”
Leading up to the big game, things had gotten tense between the two roommates. It had all culminated in a heated argument and they’d begun bickering all the time, both of them refusing to do any chores. Lee had started drinking more and more and everything became a competition between them.
The stakes of this bet started out small with petty wagers and grew and grew until it reached the point that it was at now. It was another argument over cleaning the apartment that changed the stakes one final time.
Brian had suggested that the loser pay for a cleaning service, but Lee, having just downed another be
er, suggested something else.
“How about… the loser is the maid!” he slurred. “Like, whoever loses has to dress up like one and like, clean the entire apartment.”
Brian shook his head. “Like, one of us would have to wear a dress?”
“Nah, man! Like everything. High heels, stockings, panties, makeup, a wig, earrings… everything.”
“Dude, no,” Brian had replied, walking away from his drunk roommate.
“What’s the matter? Are you chicken? Afraid you’ll lose, Brian—no, Bri… Brianna?”
Lee laughed so hard beer sloshed out of his can. Then he went on to do his best imitation of Brian as his maid, including a mock female voice.
“Oh, Master Lee, I’m so glad I could be your maid. What else can I do to serve you, my master?”
“You know what, Lee? Fine! I accept your fucking terms. Loser fully dresses up as a maid, cleans the apartment and serves the winner.”
Lee smiled and nodded. “Oh, yeah. It’s on… Brianna!”
Just you wait, Lee. My team is favored to win. You’ll be the one dressed up, I’ll be calling you some chick name and you’ll call me Master!
Days leading up to the big game, Brian had hoped that Lee had forgotten all about the deal since he made it when he drunk. But the morning of the game, Lee handed him a feather duster and said he should start practicing.
“Oh, that one!” Lee said, pointing to the image on the computer screen. “Yeah, that’s the one I want you to wear.”
Brian rolled his eyes and sighed as he brought up the costume and scrolled through the additional images. “Dude, this is ridiculous! Look at how slutty it is.”
“I know, man. That’s the point of the costume! It wouldn’t be sexy if the outfit went past your knees and covered your entire torso.”
Brian closely examined each view of the costume. It was a simple strapless black dress with short sleeves and a short skirt. The dress was lined with white ruffles and came with a matching apron, petticoat, and elbow-length gloves. It also came with a headdress lined with white lace.