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xoxo,

Clover

ONE NIGHT ONLY

Man's First Time with a Femboy

CHAPTER 1

It was trivia night at the Taproom! Jeremy’s favorite. Except he wasn’t going out as Jeremy. He was going out as Jocelyn!

His best friend Andrea was sitting on the couch next to him as they applied makeup to their faces and complained about the night’s theme: music through the decades. Jocelyn and Andrea loved music, but for trivia? They would much rather get questions about hunky actors or high-end fashion labels like Yves Saint Laurant and Prada. Or Chanel. Jocelyn once got her hands on a Birkin but had to sell it to cover her rent, which was over three months late at the time, but never mind that. She paid her rent and bought two new bags. One Gucci and the other was a Bottega Veneta. She was even planning on using the Gucci bag tonight. It was tiny, black, and perfect in every way.

“Do you think we should study?”

“I am not studying for trivia,” Andrea chided as she ran a bright red Clinique lipstick over her lips. Their Red-Handed shade, to be exact. Jocelyn was partial to YSL’s Lale’s Red and pulled it out of her makeup bag to apply it to her lips. They were both wearing short, slutty dresses and heels so tall they would make most people stumble and fall, but these girls were experts. They’d spent countless hours pacing back and forth up the sidewalk in heels, pretending like they were models, but who was looking for models in Ridgewood?

Not that they were interested in modeling.

Jocelyn had a wonderful career as a paralegal, and Andrea was a nurse. They saved up their money and took trips to Chicago for shopping sprees, especially whenever they heard about a good sale going on up there. They once went to a sample sale that happened at five o’clock in the morning. It was at this dingy warehouse on the outskirts of the city, but it was packed with designer labels. Andrea and Jocelyn spent their rent money that morning, but it was totally worth it. They walked out of there with two huge bags each.

As a matter of fact, the dress Jocelyn was wearing tonight came from that sample sale. It was a red Versace turtleneck minidress that she absolutely adored. It was sexy and comfy, and she was wearing it with a pair of Jimmy Choo pumps. People often told her that her money problems would go away if she stopped buying designer clothes, but she absolutely refused to listen.

Andrea was wearing a Ramy Brook sequined minidress with a pair of Larroudé strappy pumps that made Jocelyn ooze with envy. Sometimes she thought about taking two outfits to the club with her just so that she could change halfway through the night, but it became too much of a hassle the one time she tried.

The girls finished their makeup. For a pop of color, Andrea threw her things into her green Tory Burch bag. Both their purses had gold chains, and Jocelyn needed to document the moment with a picture before they left for trivia night.

“Smile for the camera, bitch.”

“Who are you calling a bitch, bitch?” Andrea laughed as she stood next to Jocelyn and smiled. They pressed their faces together and took several more pictures. “I hope there are some cute guys there tonight. Your girl needs to get laid.”

“We always hope there’ll be cute guys, but there never are,” Jocelyn said in her feminine voice. Nobody ever questioned her when she went out as a woman. She’d spent countless hours mastering the voice and mannerisms of a woman. She was even petite enough that she could shop in the women’s department, so she looked just like a woman when she put on her designer labels and dolled up her face with makeup. “But what do you expect? It’s the Taproom.”

“Just because it’s the Taproom doesn’t mean there can’t be cute boys! Don’t you know how desperate I am for some dick?”

“Clearly, you’re quite desperate,” Jocelyn said with a laugh.

Andrea frowned. “You act like I’m the only one.”

Jocelyn shrugged as she pulled out her compact to check her face. If they were going to take forever getting out of the door, she could at least make sure that she looked cute. “I might want a man, but I’m not afraid of pleasing myself with a toy.”

“Gross! TMI!”

“You’re the one talking about finding a man to bend you over the couch and do you hard!”

“Who said anything about bending me over a couch?” Andrea asked in a high voice, her cheeks red with blush. “I never said anything close to that!”

“I can see it in your eyes,” Jocelyn said to her friend, but the truth was she longed to have a man of her own. There were some guys in her life who would come over to satisfy her needs if she called them in the wee hours of the night, but she wanted a man who would make her heart stir. One who would stay to keep her warm throughout the night instead of the ones who only wanted a booty call. She didn’t know when or if one would arrive, but she was hopeful that the right guy would come eventually.

“Whatever. Are you ready to leave?”

“Yeah,” said Jocelyn. “Are we taking a taxi?”

“Uh, yes! I want to drink.”

“Me too. I need something strong.”

“You and me both,” Andrea said as they stepped out the door.

 
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