Biking Buds Pt. 04

Mark closed the door to his bedroom and sat on the end of his bed, trying to think about how he wanted to handle this. He didn't have to think very long. He knew exactly what he wanted to do next.

He walked over and sat at the vanity. He put a headband around his head to hold his hair back out of the way. He turned on the lights around the mirror and started to brush a warm beige powder on his face.

He pulled out the drawer of eye shadow and looked at his choices. He decided to go with a light pink on his lower lids, with a very light purple near his brows. He used a brown eye brow pencil to shape his brows, then bushed black mascara on his lashes.

Next he brushed some light pink blusher on his cheekbones and blended it up make his face appear thinner. He closed the eye drawer and opened the lipstick drawer. Of course he chose a pink shade for his lips to match his eyes. He sat the lipstick on the vanity, to be applied just before he went back out to the kitchen.

It was more make-up than he usually wore unless he was going out. But this time was different. This time he wanted to look feminine... and pretty.

He pulled the headband off and brushed his hair out. He wasn't really happy with how it looked, so he put a wig cap on and looked at the three wigs on Styrofoam heads in the closet. He chose one of his favorites, a brunette color cut in a shag style with some bangs. He teased the top and back to give it a little body. It wasn't a wig he would normally wear with the dress he had in mind, but he liked it.

He chose a pair of silver dream catcher ear rings that dangled below his pierced lobes. He put faux diamond studs in the second hole in his ear lobes.

He walked into bathroom put his t-shirt, shorts and panties in the hamper. He got a pair of sheer tan control top pantyhose out of a drawer of the chest and sat on the edge of the bed to put them on. He stretched his feet out, admiring how his pretty toe nails looked in the sheer hose. He pulled them up around his waist and made sure there were no wrinkles, then made sure they were tight against his crotch to hold his cock and balls in place.

Next he got his favorite black bra from a drawer. It was one he could almost wear without forms, but for tonight filled the cups with his b-cup silicone forms. He bent over and wiggled the forms and his chest until they were sitting naturally on his chest.

On his way back to the closet to get his dress he stopped and looked at himself in the full length mirror. He liked what he saw. He saw a pretty woman who was sexy, but not slutty. He wondered if Doug would think he was pretty.

The dress was a fairly tight sheath that hugged his round ass and had some folds across the front of the skirt that would hide if he developed a bulge, even though with these hose on there probably wouldn't be a bulge if he got a full on hard-on.

He pulled it over his head and smoothed it down his body. He looked in the mirror and adjusted the fairly low neckline to show as much skin as possible without letting his forms show.

He looked at the shelves of shoes. He had several options, from dress flats to four inch heels. He chose a pair of black open-toe sling back pumps with three inch spike heels.

He went back to the vanity and sat down. He thought about putting gel nails on, but decided to go for the just quick drying polish. His fingernails were fairly long, for a man, and shaped like a woman's. He quickly painted his nails to match his toe nails, then waved his hands to speed the drying process.

He drained the last of the watered down bourbon in his glass, then put his pink lipstick on. He took one last look at himself in the mirror before he took a deep breath and opened the door. Time to introduce Doug to Marsha.

Doug was still sitting at the bar when Marsha walked out of the bedroom. He looked up and looked surprised. A low "Wow" escaped his lips.

Marsha smiled. "I hope that was a good wow," she said.

"Uh, yeah, uh, of course..." Doug stammered. He watched his friend walk out, amazed at how natural he looked in the tight dress and how well he walked in the heels.

Marsha almost laughed at her friend. He was perched on the barstool with his feet on the floor, wearing the t-shirt she had put on him that morning, his pants and underwear on the floor near his feet. His soft cock lay on his thigh. Marsha could see dried cum clinging to the hair on his leg.

"I'm sorry," she said in her low, breathy female voice. "I just left you out here like that. Would you like for me to clean you up and help you with your pants and underwear?"

She came into the kitchen like this was a normal thing, ignoring how Doug was looking at her. She grabbed a soft dish cloth out of a drawer and went to the sink.

"Uh, yeah, that would be great," Doug said.

He watched how Mark moved in the heels, how his ass looked in the tight dress. It was different from how Mark usually moved... he wasn't sure how or why, but it was different. He felt like he should say something, give him a compliment, but wasn't sure how to word it. He wasn't used to telling his best friend that he was pretty!

Marsha soaked the rag in warm water, then wrung it out. She didn't look at Doug's face as she walked back around the bar to where he was perched on the stool. She grabbed his soft dick and rubbed the warm cloth over it, wiping away the dried cum around the tip and his sensitive head. She held his dick while she rubbed the cloth on his thigh, scrubbing the dried cum from his hair. She liked the feel of a soft dick in her hand. And in her mouth. But not right now.

She felt Doug's dick begin to grow just a little. She smiled as she put the rag on the bar and knelt in front of him. This time she didn't shove her face in his crotch and take his cock into her mouth. She held his briefs and let him put his feet through the leg holes. She pulled them up his legs.

"Stand up," she said. He did, and she pulled the briefs up around his waist. This time she made no pretense... she held the elastic waistband with one hand and reached the other down inside his briefs to adjust his cock and balls into what she knew from experience was a more comfortable position.

She reached for the shorts and repeated the procedure with them... well, except for adjusting his cock and balls. She was at eye level with his crotch and noted with satisfaction that the bulge in his briefs was definitely growing. When she pulled his shorts up into place she gently patted his bulge.

"There ya go." She looked up at him and smiled. "Is that better?" she asked as she stood up.

"Yeah. Thanks," he said. "Uh, Mark, um, can we talk some more?"

She smiled at him. "Of course we can, sweetie," she said. "But first, please call me Marsha. Would you like another drink? I'm going to make myself a cup of ginger tea."

"Uh, sure, uh... Marsha. Uh, I don't need any more bourbon. A cup of coffee sounds good, though, if it's not too much trouble."

"No trouble at all, hon," she said. She already had the Keurig heating for her tea, but she made his coffee first.

The buzz from the bourbon had worn off and she was more nervous now than she had been earlier. But she wanted to act like it was a normal thing for her to hang out in a dress with her best friend.

"So, I'm guessing you want to know a lot more about what you see before you," she laughed as she put his coffee on the bar.

"Uh, yeah," he said, emphasizing the yeah. "I've known you for over three years and I've never seen this side of you. And I'm thinking it's not something new."

Marsha laughed as she pulled her bar stool around the bar so she was facing Doug. She put one foot on the rung of the bar stool and crossed her legs like a woman would. She was showing Doug a lot of skin, and she saw him glance down at her legs.

"Not new at all," she told him. "Ok. I'm going to give you the condensed version first. Then you can ask questions if you want to."

Doug nodded. "Fair enough."

"But first... do you think I'm pretty?" Marsha asked.

Doug blushed. "Uh, well, you know, yeah, I guess so. I mean, if I didn't know you're a, you know..."

"A guy in a dress?" Marsha laughed.

"Well, yeah," Doug laughed. "If I didn't know that... I mean, you've got some seriously good legs, and, um, well, your ass in that dress, well..."

"Good enough," Marsha laughed. "I didn't mean to embarrass you. I just wanted an honest opinion about how I look. Girls love compliments, you know."

Doug laughed. "Okay, then. Yes, you are very pretty. And in that dress, very sexy. I was trying to say that if I saw you out in a club in that dress and didn't know, I'd probably be hitting on you."

"Aww, you're sweet," Marsha said. "Okay, back to the story of how I came to be sitting before you in a cocktail dress and high heels."

"It started when I was young," she said. "I always loved wearing my sister's dresses. I don't know why, but I felt comfortable in a dress. As I got older I was told that I couldn't wear dresses, because, you know, boys don't wear dresses. That made me want to wear them even more. Sometimes I even wished I was a girl so I could wear a dress if I wanted to."

Doug was nodding and sipping on his coffee.

"As I got older I kept wanting to wear my sister's clothes. I loved wearing her bras!" Marsha continued.

She saw the puzzled look on his face. "Her training bras fit tight on my chest," she explained. "Just having the bra on made me feel more like a girl."

Doug laughed and nodded. "I see."

"Anyway, I managed to sneak a couple of her training bras into my room before mom got rid of them. I wore them in my room and sometimes even around the house under a t-shirt," Marsha told him.

"So, where...when... how did you learn to do all this?" Doug asked, motioning with his hand to encompass Marsha's body.

"I'm getting that that," Marsha laughed. She drained her tea cup. "Ok, two cups of ginger tea is enough. Do you want any more coffee?"

She slid off of the bar stool, being careful to make sure her tight skirt stayed down around her thighs. She rinsed the two cups and left them in the sink.

"Uh, no, no more coffee," Doug said. "How about a beer? You got any beer?"

Marsha laughed. "I have beer," she said. She went to the refrigerator. She had to bend over to get Doug a beer off of the bottom shelf.

Doug smiled when he saw that the way she bent to get the beer was the way a woman would... knees and feet together, knees bent.

Marsha grabbed a bottle of White Zin for herself and returned to the bar. She saw Doug shaking his head and smiling.

"What's amusing you?" she asked as she put a straw in his beer and set it on the bar in front of him.

"I'm just still a little amazed," he said. "You walk in those heels just like a woman."

"Better than some," she said. "I've had a lot of practice. The only thing I loved better than wearing my sister's panties, bras and dresses was wearing my mom's heels. Every chance I got I was walking around the house in my sister's bra and dress and mom's heels."

She got a wine glass out of the cabinet and sat back down and crossed her legs again.

"So, there was this girl who lived down the street... Yvonne... and she and I were best friends. We talked about everything. I think she sometimes thought of me as a girlfriend. So when we were in high school I told her how I liked to wear dresses and high heels. I don't know why. But somehow I knew I could tell her."

"Wait a minute," Doug said. "Yvonne? Isn't she that f... um, chubby woman you hang out with sometimes?"

Marsha laughed. "Yes, same girl, now woman. And yes, she is heavy."

"So you've been friends with her since you were kids?" Doug asked.

Marsha nodded. "Anyway, she felt sorry for me because I felt bad that I couldn't wear dresses and heels and make-up all the time, and I was a little depressed. I cried and told her I just wanted to be pretty, just once. So she helped me dress up and put make-up on me and fixed my hair... it was a lot longer than it is now... and I was so happy that I looked pretty."

"And ever since then we've been more like girlfriends than... I don't know, a guy and girl who are friends. We went to the same college and stayed friends, then we both ended up here after college and we're still friends. In college she helped me get to know some other guys who like to dress up, and she taught me how to do make-up, just everything two girls who grew up together might do."

Doug nodded and sipped on his beer.

"So, I have to ask," he said. "Um, I'm not sure how to ask, but... well, earlier, when you, um, sucked me. You were pretty blunt about wanting to."

Marsha blushed. "Well, I was kind of in the moment, and we had enjoyed a fair amount of Crown," she said. "So you asked if I really wanted to and, well, I did. So I said so."

Doug nodded. "I'm just curious, though. I'm curious if you've wanted to do that before. To me, I mean. I figure that wasn't your first time to do it."

"You're right. It wasn't my first time to suck a dick," Marsha said. "When I was in college there were other guys who liked to dress up. Growing up I thought I was the only guy who liked to do that. But I'm not. So, anyway, I met these guys in college who are like me and most of us were curious about sex. So we experimented with each other, and I learned that I really like to suck dick."

"But I hadn't sucked a dick since not long after I got my job. Long story, real life got in the way. I still like to dress up and go out, but mostly I dress up around the house."

"Now, to answer your question... no. I had never thought about sucking your dick until that first night you came home from the hospital and I had to help you piss before you went to bed."

Doug cocked his head sideways. "Why then? If you stopped doing it so long ago."

Marsha shrugged. "I'm not sure. When I knelt down to pull your pants down, and your dick was right there in my face and I could even smell you, and, I don't know, I just got an urge to suck you. So when I told you earlier that I scooped your cum from the shower up and put it in my mouth to see what it tasted like, it was the truth. I did that because I didn't think I'd get another chance to taste it."

"That's crazy," Doug said. "All these years we've spent a lot of time together. We've even showered together after we tried racquetball. And you never wanted to suck me until this week?"

Marsha nodded. "Yeah. Well, full disclosure, when we first started hanging out I'm pretty sure I checked out your package in those biking shorts you wear. But to think I would ever suck your cock? I didn't."

"Are you sorry you did?" Doug asked.

Marsha shook her head. "Not at all. And to be honest, I will again if you let me."

Doug shook his head. "You know, my first inclination is to say no, I won't. I mean, even dressed like that, I know you're a dude. But I also know if I don't bust a nut pretty much every day I get, um, pretty needy."

Marsha laughed. "Well, I'm not going to dress like this for you every day. You want me to dress like this you're probably going to have to take me out for dinner first."

Doug smiled and cocked his head. "Well, you never know."

Marsha smiled. "Nice to know the possibility is there. Now, I need to get us something to eat. We've done a lot of drinking since that breakfast this morning."

Marsha stood up and kicked off her heels. She moved her half empty wine glass to the counter by the stove, and got Doug another beer without asking if he wanted one.

Doug watched her move around the kitchen and smiled. The more he looked at her, the more he saw Marsha and the less he saw Mark.

"I've always loved when a woman is all dressed up and kicks her heels off and cooks and stuff in her stocking feet," he said. "Reminds me of my mom."

Marsha smiled at him. "It feels as sexy as it looks," she told him.

"You know," Doug said. "There was one time... probably a year or so ago. We'd gone around the lake and it was really hot. We drank most of our water. So we stopped at that little place with the outdoor picnic tables on the east side of the lake to get a beer."

"Yeah, and?" Marsha said without turning to look at him.

"Well, it was kind of windy. We talked about it. There were a lot of windsurfers out that day, and we had to ride against the wind across the dam. You remember when I'm talking about?" Doug asked.

"Yeah, I think I do. I mean, we stopped off there for a beer a few times. But I think I remember that really windy day," Marsha said.

She turned and put two plates on the bar and sat down close to Doug so she could feed him.

"I really hate having to do this," Doug said as Marsha held the fork for him.

"I know, sweetie," she said. "Just a few more days."

She was alternating giving Doug bites and taking bites for herself with the same fork. Doug didn't seem to notice they were sharing a fork.

"You've been calling me sweetie and dear and hon ever since you changed clothes," Doug said.

Marsha nodded. "Yeah, it's just a habit when I go into girl-mode. Want me to stop?"

Doug shrugged. "Nah, it's no big deal. I just wondered if you noticed that you did that."

"I know I do," she said. "So, was there a point to the story about the ride around the lake on the windy day?"

"Oh, yeah. I forgot. Anyway, some of your hair had come out of your pony tail and was hanging down the side of your face. You know, like women sometimes do, only I think they do it on purpose."

Marsha nodded. "Yeah, they do. I probably just didn't notice it."

"I don't think it hung down your face until you took your helmet off," Doug said. "Anyway, I remember looking at the lake, and I had to look past you, and the sun was coming through the trees and there were some shadows on your face, and I distinctly remember thinking, holy crap, if he was a girl he'd be pretty."

Marsha sat back and looked at him. "You really thought I was pretty then? All sweaty and no make-up and in biking clothes?"

Doug nodded and laughed. "Yeah. I don't know why that just came back to me, but I do remember as plain as we're sitting here that I had that thought when we were sitting there drinking our beer. You were smiling about something, and I thought that."

"Well, that's interesting," Marsha said. "And thank you. Now that you know about me, you know I like to be pretty."

When they were finished eating Marsha took the dishes to the sink. "I'll rinse these and put them in the dishwasher after I get out of this dress," she said to no one in particular. She knew Doug didn't care when or if she did the dishes.

"Um, Marsha," Doug said. "Uh, I don't know if you want to change clothes first, but I've had two cups of coffee and two beers in the last few hours and, uh..."

"And you need to piss," Marsha laughed.

"Yes, I do. But I can probably wait for you to change if you want to."

"Why do I need to change?" Marsha asked. "Are you going to piss on me?"

Doug laughed. "Well, no. I just thought... I don't know why."

"Come on," Marsha said, leading the way to the bathroom. "You want to sit or stand?"

"Stand, please," Doug said as he stood in front of the toilet.

Marsha was more at ease handling his dick now. She stood beside him and pushed his shorts down around his thighs. She grabbed his soft shaft and pointed the tip toward the toilet.

Doug spread his legs and tried to relax. It was hard enough to piss when his best friend was holding his dick. Now his best friend looked and smelled like one of his sexiest dates and was holding his dick. He hoped he could finish peeing without it getting hard.

Marsha held his dick until the stream slowed and became drips. She shook it a few times to get the droplets off, then wrapped her fingers around it and jacked up and down a few times.

Doug leaned over and pushed his ass back against Marsha.