by John Dylena
The fact that Lisa was one of the most beautiful women he had ever seen made it easier to swallow. And he had heard about how enjoyable it is to be pegged, considering that the prostate is the male g-spot.
Then there was Anne. They had been going out for little over a week, but for some reason she seemed distant and reluctant to go steady with him. So it wasn’t like he’d be cheating on her by doing this; he could say it was part of his job.
Besides, porn stars have SOs, and they still have sex on camera.
“Okay, I’ll do it,” he sighed.
“Yes! Thank you, Mark!” Lisa hugged him. “Don’t worry. I’ll be very gentle with you, and like any other movie, we can cut and stop filming. I’ll give you a safeword, and if you utter it, I’ll immediately stop what I’m doing—no matter what.”
“Come on, Mark. We need to find you a pair of stockings and give you a little makeup.” Becca grabbed his hand and the two women led him away from the group into the makeup room.
“What the fuck, Mark?!” Lisa slammed the door to their bedroom and stormed up to their bed.
“I… I can explain!” he replied, climbing off of the bed and covering his erection.
“Yes, explain to me why you are wearing my stockings and jerking off.” She crossed her arms. Mark opened his mouth to explain, but she waved him off. “Actually, you don’t need to explain. It all makes sense now.”
“What does?”
“My boyfriend is a sissy slut. And you know what happens to sissy sluts?” Lisa turned away from him, walked over to her dresser, and dug through the contents.
“What happens to them?” Mark said, looking over at her.
“They get fucked in the ass,” Lisa replied, pulling out a black leather harness with a flesh-colored dildo attached. He watched with wide eyes as she stepped into the harness, tightened it, and walked up to Mark.
“Bend over, slut!” she commanded, turning him around and pushing him onto the bed.
“And cut!” Ricardo shouted.
Mark let out a huge sigh as he rolled over onto his back.
Lisa handed him a robe and sat down next to him on the bed. “That wasn’t so bad, was it?”
“It’s weird wearing stockings. It’ll be even weirder wearing the full get-up.”
“Oh, you’ll get used to it. In fact, I think you look good in stockings,” Lisa teased.
“That’s it for tonight!” Ricardo shouted. He walked up to Mark and Lisa. “Mark, have you ever been pegged before?”
“No, I haven’t.”
“Then we’ll need to you come quite a bit early tomorrow. Eat a light breakfast and have a liquid lunch. When you get here, we’ll clean out your insides and warm you up with a small plug.”
Lisa could see the frightened look on his face. “Don’t worry, Mark. I’ve pegged lots of guys. The first time is the hardest, but as long as we take it slow, you’ll be fine. Most guys I peg were skeptical or had no interest, but later thanked me for opening their eyes to it. Doesn’t make you gay or anything.”
“Thanks. I hope it’s as enjoyable as you say it is,” he sighed.
The following night, Mark discovered the joy of being pegged. He showed up when he was told to, and after prepping him, there was still plenty of time left, so Lisa offered a warm-up session with Ricardo’s approval.
In her private room, Lisa took Mark slowly and gently with the smallest strap-on they had. Afterward, she plugged him up and kept it there until filming started and she wielded the same one as the night prior. At the end of the night, Mark went home sore, but very satisfied.
“Oh, Mark, before you go…” Ricardo called out to him. “There has been a change in the script.”
“What is it?”
“Butch is out of town for a wedding, so instead of having him show up in the next part, we managed to secure a guest domme. She’ll play a friend of Lisa’s who helps further your feminization. Tomorrow you’ll be dressed in the full outfit and pegged by two ladies! Doesn’t that sound like fun?”
Ricardo slapped him on the back and left, laughing. Mark rubbed his face as he walked back to his car, planning on spending the remainder of his night in his bedroom, drinking himself to sleep.
Anne was waiting for him back at his apartment.
“How was work?” She poured herself a shot of whiskey.
“Fine,” he replied. “Is everything okay? Where’s Zack and Steven?”
“They went to a party. It’s just you and me here. Tell me about the studio you work at.” She tossed the shot back and poured herself another.
“It’s a small indie studio. I told you this already. What’s bothering you?”
“I start a new job tomorrow, and it’ll be difficult for me to stay in a relationship. I’m sorry Mark, but I’m breaking up with you.” She knocked back the second shot.
His jaw dropped. “What?”
“My job is very demanding, not to mention my schedule is never set in stone. I took a short break to catch up in school, so now I’m at a point where I can start working again.”
“I see,” he replied, dropping his head.
“Mark, you’re a really nice guy and all, it’s just… I felt like something was missing in our relationship, and it was awkward for me. I’m sure you’ll find someone.” She quickly took a third shot of whiskey before walking around the counter and kissing Mark.
“Enjoy that photo. We may not be a couple any more, but if you ever need an itch scratched, call me.”
Mark said nothing as he watched her leave the apartment. She closed the door and he stood in disbelief. When he finally snapped out of it, he grabbed the bottle of whiskey, a glass full of ice, and went to his bedroom.
He woke up the following morning with a terrible hangover and a strong desire to call in sick. As he wallowed in his misery, he was reminded of the wonderful pleasure of being pegged by Lisa.
Is this really happening to me? Am I growing fond of taking it in the butt from a beautiful woman? He sat up on his bed and scratched his head. Tonight, I’m going all the way. Dressed up like a woman and everything. God, I hope no one I know watches this.
Mark sat in his car for over half an hour building up the courage to walk through the front doors. It was weird enough wearing stockings, but tonight he was going to wear the whole thing.
He recalled the outfits that Cole had worn in the pass: short, tight dresses, stockings, high heels, miniskirts, and tied-off blouses.
Am I going to have to wear a mini-skirt and blouse? Like a schoolgirl? He leaned forward and pressed his head to the steering wheel, groaning.
There was a knock on his window, and Mark thought he was going to have a heart attack.
Standing next to his car was Lisa, holding back her laughter.
“Everything okay, Mark?” she said as he rolled down his window.
“Yeah, it’s just…”
“Nerves getting ya?”
“Yeah…”
“Look, Mark, no one is making you do this. You can always back out and no one will blame you. You think Cole was the first guy we hired? We went through ten guys before finding one that stuck around.”
He rolled up the window and got out of the car. “It’s just weird.”
“It’s weird because that is how society labels it and it’s what’s you’ve been conditioned to think. At least give it a chance. You’ll never know if you don’t try it. Besides, you can go back to being an intern when we find a permanent replacement for Cole.”
“You’re right,” Mark said with a nod. “Let’s do this.”
“Good! I’m excited for tonight. I’ve heard good things about our guest domme.” Lisa wrapped her arm around Mark and led him away from the car.
Inside, Lisa kept her arm around Mark as she led him down the hallway to the sound stage where Ricardo, Beatrice, and Becca were waiting for him.
“Okay so tonight we’re starting with Mark all dressed up, makeup, wig, and all. It’ll start with Lisa applying some lip gloss on
Mark, telling him how pretty he is and whatnot, and about how her friend is coming over to have some fun with him.”
“Speaking of which, have we heard from her?” Lisa added.
“Nothing yet,” Ricardo replied, “but she should be here any minute.”
Lisa sighed. “I hope so. I really wanted to chat with her beforehand.”
“Mark: are you ready?” Ricardo asked, putting his hand on the former intern’s back.
“As I’ll ever be,” he sighed.
“Ladies, he’s all yours. Make a woman out of him.”
“Come on, Mark,” the two women said, taking his hands. “This will be fun.”
For the first time since Mark started working in the studio, he saw the inside of wardrobe.
“That’s… quite a lot of clothes,” he said, marveling at the rows. There was an assortment of mini dresses, skirts, blouses; leather and latex pieces, and a wide array of heels in every color and style. On top of the rows of clothing and shoes were wigs of various lengths and hues.
Becca browsed through the dresses. “Don’t worry, Mark. Everything is thoroughly cleaned and washed after it’s been worn. Let’s get you dressed.”
Mark sat in a chair and anxiously watched the two women mix and match outfits, wigs, and shoes. His mouth went dry and his throat clenched up when they finally decided on an outfit.
“It’s a good thing you’re not all that hairy, otherwise you would’ve had to shave before coming tonight,” Becca said, holding out the clothes.
“Nothing too trashy or slutty, but still very sexy,” Beatrice said, inspecting the dress. It was dark red and made of a stretchy fabric that would cling to his body, showing off every curve. It had a low neckline that would’ve put any cleavage he had on display.
“Since you’re already thin, there won’t be any need for a corset. Unless you want more defined curves?” The two women waited for his reply.
“No, no. I’m good.”
The two women pouted. “Cole never wanted to wear a corset either,” Becca lamented. “Someday…” she added wistfully.
“Okay, Mark, step into that changing room over there and strip out of your clothes. We’ll hand you your outfit piece by piece. Once you’re dressed, we’ll do makeup.”
Inside the changing room, Mark’s hands trembled. They took his clothes as he stripped out of them, and he stood naked with the black lace panties in his hands.
Lisa’s words echoed in his head. Give it a chance.
Swallowing hard, he summoned the courage and stepped into the delicate underwear. He slowly pulled them up his legs until they gently caressed his groin.
Huh, these are… strangely comfortable, he thought, looking at himself in the mirror. It’s almost like I’m wearing nothing at all. They’re so light and delicate.
“Time’s a-wasting, Mark,” Becca called out. “Chop, chop!”
He quietly sighed as he clasped the bra behind his back and picked up the first rolled up stocking and pulled it up his leg. It gently caressed his skin, showing off his calves and toned thighs.
Mark stared at his stocking-clad leg until there was a knock on the changing room door and a reminder of the deadline. He quickly pulled on the second stocking before sliding into the heels and stepping into the dress, shimmying it up his body.
“Umm, I can’t zip up the back,” he shouted.
“Are you otherwise dressed?” Becca replied.
“Yes.”
“Then open the door and come on out.”
Mark reached for the knob, but an overwhelming sense of embarrassment kept his hand from turning it.
“What’s the matter, Mark?” Beatrice said after a moment.
“I… I can’t do it.”
“Don’t be afraid. We’re not going to laugh or make fun of you. If we thought it was weird or gross, we wouldn’t work here. Come on out. I’m sure you look great.”
Mark took a couple of deep breaths and closed his eyes as he opened the changing room door. He stepped out in the main room, his hands together in front of him and his eyes on the ground.
His face was the color of his dress.
“Oh, wow, Mark! That outfit looks great on you. And once your makeup is all done, you’ll look even better.”
“Think so?” he asked, loosening up. “It just feels so… weird.”
“Everything is weird the first time you do it. Don’t worry.”
The two women grabbed his hands, led him through the door, and sat him down in the makeup chair.
“Let’s keep it a surprise,” Becca said, turning his chair away from the mirror.
The two women silently nodded and got to work on Mark’s face. When they finished and added the brunette wig, Mark’s transformation was complete.
“Not a hint of your old self visible. Ready for the big reveal?”
“Yes,” he replied, his voice trembling.
It was nerve-wracking watching them go to town on his face. They held nothing back and used every item in their arsenal to make him into a good-looking woman.
“I think this is our best work yet,” Beatrice said, turning Mark’s chair back toward the mirror.
“Holy shit,” Mark said, covering his mouth in shock. “I… I can’t believe that’s me! I look so feminine!”
“Come, Mark.” Becca stuck out her hand. “Let’s show the rest of the crew the new you.”
He took a deep breath and the two women held his hands as they opened the door and led him out of the makeup room. Over by the lounge area of the sound stage, the rest of the crew, including both Ricardo and Marie, were gathered and chatting.
The sound of high heels on the concrete floor stopped the conversations and all eyes turned to Mark.
“No fucking way!” Lisa said, running up to Mark. She put her hands on his shoulders and smiled. “Mark, you look amazing.” Everyone else walked up behind Lisa and joined in on complimenting Mark.
“Oh, right, let me introduce you to our guest domme.” Ricardo said, squeezing through the crowd and placing his hand on Mark’s shoulder. “Mark, this is Lady—”
“Anne?!”
A redheaded woman dressed in a shiny black leather outfit stepped through the crowd. She extended her hand and they both froze when they saw each other.
“Mark?!”
“Oh, this is perfect,” Lisa laughed. She watched Mark and Anne stare dumbfounded at each other. “Please tell me you used to be a couple.”
“We, uh—we were. Until yesterday,” Mark said, pulling his gaze away from his ex. “This is why you broke up with me? ‘Cause you’re a domme?”
“Yes. I’s difficult for me to maintain a healthy relationship with someone while I’m working as a domme. I’m still new to this whole thing, and I’m not experienced enough to keep my two lives separate.”
“How long have you been doing this?”
“Almost two years now. I first discovered this part of me freshman year. Took me a while to realize what I am and when I did, I sought professional advice. I became an apprentice to another domme, and for the past year and a half, she’s mentored me and taught me everything she knows. Instead of starting out on my own, she told me to do some collabs with other dommes to build a network and learn from others.”
“She contacted me, and I eagerly accepted her offer. I know and highly respect the woman she trained under.” Lisa said. “But this… this is priceless.”
“So, Mark…” Anne folded her arms. “Have you always been a crossdresser?”
“No, today is actually my first time.” He looked down at his own outfit, inspecting his heels and adjusting the hem of his dress.
“I hope this won’t be the last,” Anne purred. “I like seeing you in a dress. Turns me on.”
Mark’s face turned bright red as Anne placed her hand on his cheek.
“This is great!” Ricardo cheered. “It’ll make the film more authentic. All right, ladies and gentlemen; let’s get to work!”
“Oh my, you look like such a
slut,” Lisa said, applying a coat of gloss to Mark’s lips.
He sat on the bed in front of her, hands together on his lap, looking away from the blonde woman. She had changed out of her business attire into a corset, thong, and thigh-high leather boots.
Mark looked over to the bed where the strap-on harness waited.
“Pucker those lips for me,” Lisa commanded. “Good girl. I have a surprise for you tonight.”
“What is it, Mistress?” Mark asked, his voice soft and feminine.
“You remember Anne? My friend from work?”
“I do, Mistress.”
“Well, I told her about how I found you in my stockings and how I dressed you up like the slut you are. She’s on her way over and she can’t wait to fuck you. You like that, don’t you?”
“I do, Mistress.”
“Can’t wait to have another cock inside you? Tell me how bad you want another cock.”
“I want another cock inside me,” he begged.
“It’s a shame her boyfriend is out of town on work, otherwise she would’ve brought him along and you could’ve tasted a real cock.”
“Hello? I’m here,” Anne said, walking in through the door.
“Hello, Anne!” Lisa said, hugging her friend.
“Oh my god! Is this him?” Anne pointed to Mark.
“Her, Anne. That’s no man. She’s my personal slut and her name is Malinda.” She turned to Mark. “Ain’t that right?”
“Yes, Mistress. I’m not a man. I’m woman and a slut,” Mark, replied.
“Ready to have some fun?” Lisa asked, stepping into her harness.
“Am I ever!” Anne removed her heavy coat, revealing her skin-tight leather outfit and bright pink strap-on.
“Onto the bed, slut! Hands and knees,” Lisa commanded.
Mark silently obeyed and he climbed onto the bed. He didn’t look back as Lisa lubed up his asshole.
“Anne, since you’re the guest, how would you like to fuck my slut’s pussy?”
“Why, I’d love to!” Anne replied, taking the lube from Lisa and prepping her bright pink cock. “Thank you, Lisa.”
Lisa nodded as she climbed onto the bed and moved in front of Mark. “Well, what are you waiting for?”