by John Dylena
“I know what pegging is.” He looked away from her.
“Well? What do you think? I could peg you, and you could even wear my lingerie while we do it. I can get you a wig, even do your makeup!”
“I… I don’t know, Erica. I mean, this,” he said as he motioned to his body, “was really just a fluke. Before tonight I never thought about cross-dressing.”
“Well, I’ve been gone long enough. If you really didn’t like it, you would’ve changed out of it by now.”
Stephen frowned. She’s right. I could’ve changed out of it the moment I put it on. But no, after the panties I put on the stockings, then I put on the teddy.
“Besides, no matter what you say, I know you like it.” Erica smiled as she pointed down to Stephen’s rigid cock. It poked out of the top of her thong. The tiny patch of fabric on the front held his balls.
His face turned bright red as tried to cover his erection. Erica grinned as she stepped toward him. She circled around him and he backed into the counter of the vanity. He was only an inch or two taller than her, but when she wore her heels she towered over him.
Stephen moaned as she slid her finger along the underside of his cock and it twitched at her touch. Erica pressed her body against his as she reached over and opened one of the drawers of the vanity and pulled out a tube of lipstick.
His lips quivered, but he voiced no protest as he watched her slowly remove the bullet-shaped cap and twist the base. The rose-colored makeup came into view and he watched as she brought it to his lips and dragged the waxy surface across them.
A chill went up Stephen’s spine and he shuddered. He closed his eyes as his body writhed under Erica’s. Her breasts pressed against his chest and she rubbed her smooth legs against his stockings. His knuckles turned white as they gripped the edge of the countertop.
Her lips twisted into a satisfied smirk as she put the tube away. Erica kept her hand on Stephen’s chest as she moved away from him and reached for the wooden chest atop her vanity. He watched her dig through her collection of earrings until she produced two gold clip-ons. Rhinestones dangled beneath the clips and he winced as she attached them to his ears.
The weight was foreign and he shook his head slightly, feeling the pair tug on his lobes. Just like the lipstick, he could think of no argument to defy her. He wondered how much further she was going to take this and why he wasn’t protesting against it.
No matter how hard he tried to think of a reason to get her to stop, Stephen couldn’t find one. Every idea slipped through his fingers like a cloud, and his dick would throb. He was incredibly turned on by all of this, more so than when he first started dating Erica.
The lipstick and earrings were only the tip of the iceberg.
She went onto to decorate the rest of his face, using a light, airy foundation to hide the facial hair just starting to grow back and smoky eye shadow for a subtle, yet sultry look. She brushed through his eyelashes, enhancing them with an application of lacquer, and swiped them gently with her thumb to remove the excess mascara.
Erica finally broke the silence. “Up onto the counter.” Her voice wasn’t soft and comforting, but it wasn’t harsh and commanding either. It was stern. There was no doubt, no hesitation, just the order.
Stephen nodded as he silently climbed up onto the counter. The marble surface was cold upon his bare ass and he grimaced as the thong rode up into his crack. Erica took his hands and placed them on his thighs, spreading his fingers apart.
She stepped away momentarily and returned with a bottle of red nail polish, quietly humming to herself as she coated his nails in the crimson shade. Once she was finished with the tenth finger, she blew on them.
“I’ll be right back,” she said as she twisted the cap back on. “Do not move and do not look at your reflection, understand?”
Stephen nodded and his eyes went back to the shiny coat of paint on his nails. He marveled at how feminine they made his hands look and lifted them up to his painted lips and blew gently on them.
“Close your eyes,” he heard her say. He looked over at the doorway and watched Erica poke her head in.
He smiled as he closed his eyes. He could hear her walking toward him, and a moment later, he felt a shoe slide onto his foot. It was a little bit small, and from the way his foot bent, he knew exactly what it was.
“Keep them closed.”
He wanted so badly to open them and to see the high heels she placed on his feet, to see how they shaped his legs and how feminine they made them look combined with the stockings.
Did I really just think that? Am I really that turned on by the fact that she is dressing me up as a woman?
His body answered that question as a heat flowed through him and his cock twitched. Precum had been slowly oozing out of it ever since he first put on her panties. When he decided to put on her stockings and teddy, he was afraid that he would be so turned on by it that he would have a hands-free orgasm.
He’d kept a lid on it so far, but he knew the moment he—or Erica—touched it, he’d explode.
Her second surprise was even more obvious. The long hair of the wig tickled his shoulders, back and neck. Erica only had the one wig. It was blonde with layered and wavy hair. Once she finished adjusting it, she gave him the order to open his eyes.
Erica took his hands and helped him down off of the counter top. The heels that she gave him were the black ones that she’d had on earlier in the evening, but his attention was quickly torn away from his footwear when she turned him around and showed him his new look.
“What do you think?
“I… I can’t believe that’s me. I look so feminine.”
“Come on, Stephanie, I think it’s time we experiment at little further.”
Stephen’s face turned bright red at the sound of his feminized name. Not since he was in elementary school had he been called Stephanie. Back then, his classmates would all call each other girl’s names to tease one another. Stephen was called a girl more often than the rest because of this thin frame.
Erica took him by the hand and led him out of the bathroom. He followed behind her, walking in slow, deliberate steps. She turned around and took his other hand, walking backwards as she directed him on how to walk in high heels.
She walked into the bed and sat down, spreading her legs as she looked up at him. “I want you to take off my pants and pleasure me.”
Stephen hesitated for a moment and Erica raised an eyebrow. “Well? My pussy isn’t going to lick itself, you know. Chop, chop, Stephanie!”
Erica poked at his chest with her toe and he obeyed her command. She smirked as he pulled off her tight gym shorts, revealing her black cotton panties. He tried to remember the last time he gave her oral. Must not have been very good at it if I can’t remember the last time I did it. He heard her giggle as he pulled her panties down past her knees and off of her legs.
He knelt down in front of her and she watched him as he parted her pink lips with his left hand. She was already wet.
“Ooh!” she yelped as he buried his head in between her legs, wrapping his arm around her right leg and covering her tender flesh in countless kisses.
Stephen parted her outer lips and lifted up her tiny clit hood with his fingers, giving his tongue access to the sensitive pearl beneath it. Erica responded to his exploration with a drawn out moan as she fell back onto the sheets so hard the bed shook.
He smiled from in between her legs, his tongue flicking back and forth. His fingers moved to her inner lips, tenderly pulling them apart and fully exposing Erica’s pussy.
“Oh god, yes!” Erica cried out, writhing on the bed as Stephen kept up his assault with his tongue. “D-Don’t stop!” She squeezed his head with her thighs, holding it in place as he brought her closer and closer to sensual bliss.
Her strong legs muffled his hearing, but he could still make out the sound of her scream as she arched her back and filled his mouth with her juices. She relaxed her still-quivering legs, releasing
him from her grip. He fell back onto his heels and wiped her sweet-smelling liquid from his face.
Erica stared up at the ceiling as her chest rose and fell quickly. Her heart raced and she gasped for air. It had been quite some time since she’d had an orgasm like that, and as tired as her body was, she wasn’t ready to call it a night just yet.
There was still one more thing she had to do.
“Up… up onto the bed, Stephanie,” she commanded as she rolled off of the queen-sized mattress. “Hands and knees, and no peeking.”
Stephen crawled up onto the bed as he was told and anxiously awaited for Erica to return to him. He didn’t need to look back to know what was coming. Erica was digging around for her strap-on. He knew she had one—in fact, he had stumbled upon it months ago. She told him that she had got it back when she was dating one of her exes, but never got around to getting rid of it.
Looks like she’s finally going to get to use it, Stephen thought as he bit his lip. He jerked forward and grimaced at the cold application of lube. Erica was very thorough and generous, which involved her fingers sliding into his bum.
“Like that, don’t you?” Erica cooed in his ear from behind him. “There are a lot of guys who enjoy pegging. The prostate is the male g-spot, after all.”
A chill ran up his spine as her fingers rubbed in prostate and he had to bite his lip to stop a moan from escaping his lips. Erica squeezed his ass as she continued fingering him, coating his insides with enough lube to allow for easy entry.
He took a couple deep breaths as she lined up behind him and grabbed his hips. “Are you ready, Stephanie?” she purred. “Don’t worry, I’ll go slow.”
Here it comes. Stephen moaned as she pressed the head of her cock against his ass and pushed in slowly. Erica kept her word as she moved gently in and out of him, letting her strap-on fall out of him before putting it back in.
“You all right?”
“Yeah, I am,” he grunted.
“Going to go a little bit deeper and faster.”
Erica readjusted her position and slid the cock back into his ass, pushing further and further until she buried the entire thing inside of him. Stephen moaned as the ridged toy rubbed against his insides, stimulating his prostate much more than her fingers ever did.
“You good?”
“Yep,” he grunted once more, trying not to show how turned on he was from all of this. Precum oozed out of his cock as Erica began rhythmic thrusts, moving faster and faster and pushing harder and harder.
There was pain at first, and Stephen opened his mouth ready to tell her to stop. It wasn’t an excruciating “stop there is something really wrong” pain. It was the same kind of pain a woman gets when she pops her cherry. It had faded away by the time Erica really started going, and the pain that followed was something of his own creation: his subconscious crying out, telling him to stop.
This isn’t right! it told him. A straight guy shouldn’t enjoy getting fucked in the ass by his girlfriend. But there was no denying the pleasure that filled him.
And from the amount of force Erica was putting behind her thrusts, she knew that he was enjoying it. He fell forward onto his elbows as Erica buried her cock inside of him.
His jaw hung slack as he tried his hardest to stop himself from moaning at the insurmountable pleasure that came from being penetrated. He felt so full and vulnerable in ways he had never experienced before. Part of him even felt complete. He bit on his hand, stifling the cry that came when she slapped his ass.
Erica spanked him again and he moaned into the sheets. How could this be happening to him? The night before, he was an ordinary guy with a smoking hot girlfriend. They had regular, vanilla sex like most couples; the kinkiest they ever got was when they used handcuffs one night after a Halloween party.
But now Stephen was dressed head to toe like a woman, wearing his girlfriend’s lingerie, her makeup, her wig, her jewelry, and her high heels. He was on his hands and knees, face pressed against the sheets of their bed, getting fucked in the ass by Erica.
It was the most turned on he had ever been.
His knuckles turned white from gripping the sheets as she slapped his ass a third time. Stephen stood on the precipice. He was moments away from arguably the best orgasm of his entire life.
As if sensing his closeness, Erica reached round and grabbed his cock. She stroked it and Stephen’s eyes rolled into the back of his head as his cum burst out of his throbbing tip. His head swam and all his nerve endings fired off at once as the orgasm that had been building up since he first put on Erica’s panties swept over him like a tsunami.
It filled him from the tips of his toes to his painted fingernails. Erica continued fucking him for a moment more until she joined him. With her cock in him as deep as it could go, she fell onto his back and let her arms dangle off of him.
They stayed connected for another minute before Erica found the strength to pull out of him. Stephen fell onto his sides, panting. He looked up at her and smiled.
“You made quite a mess, Stephanie,” she said, pointing to the large pool of cum on the sheets.
“Yeah… we should change them before we go to bed.”
“We? What is this we?” Erica winked as she unfastened the harness and removed the double-ended dildo. She tossed it aside and rolled off of the bed. “I’m going to take a nice long shower. If you hurry up, change the sheets and undress, you can join me.”
Stephen awoke the following morning to find the bed empty and Erica gone. He frowned, knowing she wouldn’t be back until late tonight. He doubted she’d have the energy to repeat what they’d done.
He rolled over in the bed and stared up at the ceiling, recalling the events of the night before. He bit his lip and squirmed as he remembered the way the lingerie had felt on his body, how the stockings caressed his legs and the heels shaped his ass. He remembered the taste of lipstick and the weight of the earrings.
But most importantly, he remembered the sensation of being pegged.
Stephen’s body warmed and his dick created a tent in the sheets. But his daydreaming ended prematurely when he heard the door to his apartment open. Moments later, Erica entered the bedroom carrying several shopping bags.
“Aren’t you supposed to be at work?” he said, sitting up and eyeing the bags.
Erica smiled. “It was supposed to be a surprise, and the reason why I bought that lingerie you ended up in. Over the past week I closed several major deals and brought in a ton of cash to the firm. Because of it, they awarded me with a week’s paid vacation.”
She set the bags down and sat on the edge of the bed next to him.
“I was going to tell you last night, but we had that fight, and I went down to the gym and… well… you know what happened.”
Stephen’s face turned bright red. “Yeah. How could I forget?”
Erica stood up and returned to her collection of bags. “Well, when I woke up this morning, I just had to go shopping.”
“What did you buy?” he asked, trying to peer into the bags.
“Lingerie, shoes, makeup, jewelry… and some costumes for you!”
“Costumes for me…?”
Stephen trailed off as Erica pulled out a white blouse and pink plaid microskirt. “I even bought some cute pink heels and white stockings to go with it.”
She tossed the items onto the bed.
“Well, hurry up and get out of bed, Stephanie! I got lots of stuff for you to try on, and we don’t have all day!”
Stephen sighed as he threw the sheets off of himself and climbed out of bed.
“But before you start dressing up, you need to shower and shave.” Erica handed him a pink razor and shaving crème and pushed him toward the bathroom. “Oh, and from now on, you must address me as Mistress. Understand?”
He laughed a little as he looked down at the items in his hand and back at his eager and excited girlfriend. It had been a long time since he’d seen her this genuinely happy. As weird as it was, he could
n’t deny how excited he was to try on all the outfits she had for him.
“Yes, Mistress,” he said with a smile.
NOWHERE TO HIDE
The door slammed shut and Joshua held his breath. He remained still, frozen, his eyes wide as he stared at his reflection in the mirror and listened. There was a man’s and a woman’s voice coming from outside the bathroom. They were laughing, then they were kissing.
Will, Joshua’s roommate, and his girlfriend Nicole were not supposed to be there. They were supposed to be on the road leading up to the mountain for their extended weekend ski trip. Four nights and five days they said they would be gone, only now they were in the apartment, unannounced, and from the sounds of it, here to stay.
Joshua’s hand shook and the golden tube of dark red lipstick fell from his fingers into the white porcelain sink. He tore his eyes away from his own and looked back over his shoulder at the bathroom door.
“Hey, Josh! You here?” Will shouted from the living room.
Please leave. Please leave. Please leave. Josh squeezed the edge of the sink and prayed that they would step out long enough for him to change.
He looked back up at his reflection. He had just finished applying the crimson red color to his lips when they had arrived. His normally modest eyelashes were now vibrant, long, and as black as night. The neutral eye shadow he had spread across his lids had a sparkle to it, and his skin was smooth, soft, and hair-free.
Around his neck was a pearl necklace, an impulse buy he’d made at a tourist trap gift shop the last time he went to the beach. It had been a hot summer, and when a friend of theirs couldn’t make it, Josh filled in and stayed at the beach house with Will and Nicole. The pearls were cheap, but from a distance they looked fancy. In his mind they were opulent; something a celebrity would wear walking down the red carpet.
His gold, disc-shaped earrings reflected in the light of the bathroom. They were only clip-ons—he had no interest in actually piercing his ears. Each was the size of a poker chip, with a Grecian design etched onto the surface.
