Girls' Night Out Ch. 01

DAY 1

His name was Cary and he was willing to admit it, he was not a man's man. Just over 5'6" and with a slight build it had been a struggle at times. He did the usual manly things, played football, (place kicker) went out for the track team, (high jumper), and drank beer, dated girls, and did the usual things one did in high school. He lifted weights but even though he toned he didn't bulk up any. When Cary went to college, he found he could be himself without the hassle one went through in high school. He let his hair grow down to his shoulders, pierced his ears and even tried to grow a moustache, without success. He majored in art and drama and did quite well.

His father died right after he was born so his mother and three older sisters raised him. This meant there wasn't a man in the family. His mom did her best but working a full time job, he was left to his sisters. It was like he was his sisters' little doll they could dress up and care for. They would sometimes bathe him and sprinkle girly smelling powder on him. He remembered wearing his sisters' clothing and thinking nothing of it. They had pajama parties and dressed him up in baby doll nighties, complete with frilly panties. Since he was always around women, he was comfortable with them and was always able to have a girl friend. He lost his virginity in his sophomore year and was told by those girls he was a considerate lover.

After college Cary and his girl friend moved to a small coastal community on the Cape. There he opened up his own art gallery where he sold his artwork and those of local artists. He acted in the community play and led a rather comfortable life. His girl friend became a successful realtor and was known as the realtor you went to if you wanted to sell your house.

Socially they couldn't have asked for a better place. The people were friendly and acceptable to all types of people. There were places to go to for good meals, and bars that catered to all different ages, styles, and taste. They loved it there. No one cared how one looked.

Once a month, Angie, his girl, and her friends would call for a Girls' Night Out. Four or five of them would meet up for drinking, dancing, and just having a great time. Cary thought it was great because Angie would come home a little drunk and then they would have mind-blowing sex. A little alcohol went a long way with her.

One night as Angie and her friend Alexa were leaving to go out, Cary casually remarked, "Hey, I'm jealous. You guys have a great time and I'm left here alone."

The girls laughed. "Silly, it's only for girls!" Angie said as she gave him a kiss. "Don't wait up."

She came home late and right on cue, they fucked their brains out. Sunday morning he woke up to her hand around his cock, stroking it slowly.

"I thought you be worn out after last night," she said with an evil smile. "I guess not."

As she slowly continued, she said, "Alexa and I were talking. You said you would like to join us on our night out. We decided it was ok with one requirement." She started stroking faster, making me groan.

Having got his attention, Cary mumbled, "What's that?"

Angie moved between his legs. "You have to dress like a girl." She punctuated her statement by running her tongue up the length of his shaft.

"What?"

"You heard me. That's the deal." She placed the head of his cock in her mouth.

"Oh, fuck," he moaned.

"What's your answer, babe?" She started sucking harder.

"I, I don't know."

Angie sat up. Her hand began to slide up and down his saliva-covered cock faster. "I need an answer and I want it now!" Her hand moved faster.

Cary's mind was in a jumble. "Yes, yes, Oh God!"

"Yes, to what, babe?" Angie asked with a wicked grin on her face.

"Yes, I will dress as a girl, yes, yes!" With that he exploded, sending his cum all over his chest.

"Then it's a deal, sweetie."

Hearing the car horn, Angie headed out the door. "That's Alexa. We are going shopping. Don't know when we'll be back. Enjoy the your day."

Cary did his usual thing. He went to his shop, talked to the tourists and generally spent a pretty lay backed Sunday. What happened that morning had completely slipped his mind.

The gallery was like many others on the Cape. It was two and half stories high with three floors. It was filled with paintings and prints, mostly sea pictures. It was somewhat successful but he was thinking of branching out. Still with local artists but with more than just paintings. This might bring in a different type of tourist. He realized that women were more his customers than men so he was going to have to think differently if he wanted to cater to them. It was hard to exactly picture what to include if he wanted their business.

The two girls returned around suppertime with a large pizza. Along with the pizza they brought home two large shopping bags. Sitting on the floor eating the pizza, Angie spoke up. "Ok, here's the deal."

Cary looked at her quizzically. "What deal?"

"The deal you agreed to this morning and I am holding you to it. No backing out, buster."

He stood up. "Now wait a minute. That was unfair."

"All's fair in love and war. You agreed and you are not going back on your word, right?" Angie's voice had a sharp edge to it.

Cary thought it over for a moment. "How bad could it be?" He sat back down. "Ok, a deal is a deal. What do I have to do?" he said with a sigh.

Angie reached into the bag and brought out an innocent bottle of body wash. "After supper you are to take a shower. Rub this wash all over your body. Follow the directions. Then we'll tell you more."

"Oh, Cary," Alexa added, "Don't get any on your face, in your hair, or eyes. Just all over your body. Got it?"

Dinner continued on with the usual small talk. Angie told them about the big deal she was closing this week while Alexa complained about the busy week she had coming at her law office. She said her boss was in a real important trial up in Boston and wanted all the paperwork done ASAP. One thing Cary liked about these Sunday pizza dinners was that it was always casual and relaxing before the start of the week. He knew his job wasn't as big as the two girls but he was successful at it.

He picked the empty pizza box and wine glasses and carried them into the kitchen. Coming back to the living room he asked as he sat down. "What's next?"

The two girls stood up and walked over to him. They each took one of his arms. Lifting him up from the chair, they said, "Time for your shower!" They handed him the body wash. "Off you go!"

Cary stripped off his clothes and stepped into the hot shower. The water felt great against his body and quickly steamed up the bathroom. He looked over the bottle. The label was torn but he could still the directions They seemed very simple, lather, rinse, and repeat. He squeezed a dollop out into hands and began to rub it on his legs. He could feel it tingle but it smelled pretty good so he continued. He had stepped back from the water to make sure he followed the directions completely.

He paused for a moment as he looked down at his cock. His pubic hair was never very thick and it was fine blonde hairs anyway. He lathered all around his cock and balls and even up the crack in his ass. It tingled even more. As he enjoyed the feeling, he thought back to the time he was about 10 years old.

His sisters decided to dress him for Halloween. They were going to pass him off as their cousin, His hair was shorter then so they purchased a blonde wig for him. After his shower they powdered him and put on some make-up. Pink satin panties, white over the knee stockings, patent leather Mary Jane shoes and a pink ruffle dress completed the look. Then they went out trick or treating and no one noticed that he wasn't a she.

There were times after that that he stole some of his sister's panties and wore them under his clothing when he went to school. It felt so smooth and soft plus it was a great feeling of being the only one who knew. He even wore a pair under his track shorts!

His sister Bobbi found out his secret. One day she came home early and walked in on him. He was lying on the bed naked with a pair of her silky panties wrapped around his cock. His hand was vigorously stroking it.

"Sorry" she said but she didn't retreat a step.

Cary was so close to cumming but he stopped in mid-stroke.

Bobbi sat on the bed. "Don't stop for me! Keep going." She put her hand on his cock and starting moving up and down. The sight of her hand drove him over the edge and he shot a huge load everywhere. As he cleaned up, Bobbi told him, "That was pretty hot. I wondered where some of my panties went."

Later on some occasions, he would find a pair of her panties folded in with his clean underwear after the laundry was done. It was as if it was their little secret. By the time he went to college, he no longer had the opportunity to wear his sister's undies.

He remembered the feeling of the satin around his cock and the smell of powder. "Maybe this girls' night out thing won't be so bad," he thought.

Absentmindedly, he stepped up into the warm water, rinsed off, and applied the wash to his body. It felt different this time but it still tingled so he continued. Doing his back was a little difficult but using a sponge and a little ingenuity, he got everywhere.

It wasn't until he stepped from the shower that he noticed the change.

"Holy shit!" he exclaimed. "I'm fucking hairless!"

That he was. Whatever was in that rinse removed every bit of his body hair, from his neck to his toes. He couldn't believe how smooth his body felt as he ran his hands down it.

He walked to the bedroom drying the hair on his head. Reaching the door, he heard Alexa say, "Nice bod!"

"What the fuck!" Cary yelled, dropped the towel over his crotch.

The two girls laughed. "Stop it, Cary. We've both seen cocks before. Now drop the towel and let us see."

They moved closer and inspected every inch. Both ran their hands over him, touching him to feel how smooth he was.

"Good job, sweetie," Angie said. "Now every time you shower, you have to use the body wash. At least until next Sunday. Understand?"

Cary nodded.

"Good, now for the next step. We bought you some new underwear." Angie handed him a light blue satin camisole and matching tap pants. She then pointed to some articles on the bed. "You are to wear these under your clothing. Don't worry; I'll help you in the morning by picking out the right ones. Understand?'

Cary nodded again.

"You are rub this lotion on your body twice a day. It will keep your skin soft.

It was late as Angie and he climbed into bed, Angie smiled and said, "You look cute, sweetie."

"It feels really good, babe."

She reached over and grabbed his cock. Rubbing it through the satin made it grow quickly. "I can see you really like it!" She pulled the pants aside and mounted him. "God, you feel so big! I think I'm going to like this more than I thought."

***

DAY 2

"Baby, you all done with your shower?" Angie yelled from the bedroom.

Cary had lathered, rinsed and just finished putting lotion on. "All done."

"Good" Angie replied. "Come in here."

He walked in naked.

"Sit on the bed sweetie. Here put on these stockings." She handed him a pair of thigh high nude stockings. "Here I'll put the first one on you." She kneeled down and picked up his foot. Rolling the stocking up, she put it over his toes. She unrolled up his leg, stopping high on his thigh. "Now you do it?"

Cary copied what she did and it was done quickly.

"Nice. You're a pro at it." She pointed to the underwear on the bed. It was a pink set, just like last night. "You can wear those under your clothes. See you in the kitchen." She kissed him on the cheek and headed downstairs.

He liked the feel of the stockings on his legs and between the rinse and the lotion, they went on easily. He put on panties, again loving the feeling to his cock. Quickly he finished dressing and hurried down to the kitchen.

As he entered the kitchen, he saw Angie holding a pair of hi-heels.

"Wait a minute, I'm not wearing those to work. No way," he said holding up his hands.

Angie shook her head. "Of course not but if you want to go out with the girls, you got to wear them. If you want to say no, then its over."

Cary thought for a moment. He really wanted to go out. "Well ok."

"Sit down," Angie pushing him back in a chair. "They are only two inch heels. Good place to start. You'll wear them around the house when you're home. Every chance you get. Now stand up."

He did what he was told.

"Now walk around."

Cary began to walk, slowly at first. He felt like he was walking on his tiptoes. With each step, he felt a little more confident.

"You know, you walk like you did this before," Angie laughed.

He began to turn around. Suddenly he stumbled and lost his balance. Only by grabbing the kitchen counter did he prevent himself from falling. Embarrassed, he smiled. "Not as easy as I thought. How do you girls do it?"

"Practice, plenty of practice," she said. "Look, I got to go. Keep practicing till you go to work. You'll get it. Love you."

Cary kept walking around the house. Upstairs and down, he walked. There were a number of times he almost fell, ass over head, but he caught himself. When he looked at the clock, he realized he had been walking for almost 90 minutes. He sat down and removed the shoes. Upon standing he almost fell. It felt so different.

"This may be the hardest part."

Cary sat behind the desk at his gallery eating his lunch. He was absentmindedly rubbing his leg, feeling the stocking against his smooth leg. As he moved in his chair, the satiny panties moved against his cock. It all felt so good.

He wondered about what was going on. "I'm not gay. I've always liked girls, not even bi. Sex with Angie is amazing. I'm not like Bruce Jenner. I don't feel like I'm in the wrong body. I do like the feel of these things under my clothes though." He rubbed his hands down his chest, feeling the softness of the camisole.

He stood up and walked over a mirror hanging on the wall. He looked himself over. He raised his hands in front of him. His hands had long delicate looking fingers. "Not man hands," he sighed. "And dainty feet."

"Just how far is Angie going to take this?" he thought. "More importantly was how far was he going to let her?"

He got in just a few minutes before Angie but he had already changed into his heels by the time she entered the door.

"Hey sweetie, how was your day?" she said. "I got Chinese."

Despite the unusualness of Cary wearing heels and wearing woman's underwear, the meal went on as normal. Small talk about works, friends, and the town gossip was covered. It was as if nothing had changed.

Angie stood up to clear the table. "I got this, you go shower. Don't forget to use the wash and shave, sweetie."

Cary headed towards the bathroom; the clicking of his heels was plainly heard. "Hey, Angie, do you think I could use that wash on my face?"

She thought for a moment and then said, "Only where you shave. Try it. I don't think it will hurt."

Cary took his shower, using the wash. When he finished, he applied the lotion. His body's smoothness felt great. He headed to the bedroom where he found Angie. Next to her was a paper bag.

"Are you ready for the next step?" she asked.

"In for a penny..."

"Ok, here goes." She pulled from the bag something that appeared to be a bra but instead was a pair of fake breasts. She showed them to him. They looked real, right down to the nipples and areolas.

He said nothing, too stunned for words.

Before he could speak, she moved towards him. She sprinkled some baby powder over his chest and back. The smell stirred some old memories. "Here, lift your arms up."

He did as he told as she slid them over his head. It was like putting on a pair of football shoulder pads. Sort of. Pulling them into place, she stepped back. "There."

"They're, they're huge! And heavy too," Cary stammered.

Angie adjusted them on his chest. "Alexa said they are D cups. She got them from a friend. As for being heavy, now you know what we girls go though." She cupped them in her hands. "They feel real." She moved her hands from side to side. "Wow, they even move like real ones. I understand when they warm up they feel better."

"Great!" Cary exclaimed, "When am I suppose to wear them? I'm not going out wearing them."

"Don't worry. Just around the house," she said with a smile. "For now," she added softly.

She reached into the bag again. Cary stepped back.

"Relax, Silly. Here," and she handed him a baby doll nightie. "You sleep in this tonight. It has a g-string to go with it but I don't think you are ready for that. Wear these." She gave him a pair of satin panties. "Get dressed and come downstairs. We can cuddle on the couch."

Later that night Angie called Alexa. "Oh my God! You wouldn't believe how he looks. With the nightie, the boobs, they overflowed the top, and that long hair; we are over half way there. And he hasn't said no yet. Oh, he is enjoying it. Last night his cock was bigger and harder than usual. After I get off the phone with you, I'm going to fuck him. Ok, so we are still a go for Wednesday afternoon. See you a little after 12. Love ya."

Angie tiptoed up the stairs and into the bedroom. In the soft light from the hallway, she could see Cary lying there on his back. She moved to the side of the bed. She could make out the outline of his semi-erect cock in his satin panties. She reached out and began to stroke it, rubbing the material around it. It began to grow as Cary moaned.

She licked her lips. Bending down, she wanted to feel him grow in her mouth. Angie put her mouth over the tip and began to suck. His cock responded immediately. It grew in her mouth as she moved up and down the shaft. It filled her mouth as his cock became harder and bigger than before.

"Oh baby!" he groaned.

Her pussy was wet, so wet she felt it drip a drop onto the sheets. She wanted his big cock in her. She straddled him, driving his cock into her waiting pussy. She had never felt full. When she had him in her completely, she shuddered from her first orgasm.

Overwhelmed by the lust, Angie began to move up and down his length. Orgasm after orgasm shook her body, each one getting stronger. Leaning forward she grasped his breasts, fondling each one.

Sweat dripped from her on to Cary's breasts as Angie's orgasm grew. When she came it felt like no other she had ever had. She screamed in delight as it swept over her. Her pussy spasmed around Cary's cock causing it to erupt. He slammed into her lifting her off the bed but still imbedded in her.

Completely spent, Angie collapsed onto Cary. As she recovered she thought, "This is going better than I ever imagined!"

***

DAY 3

"Hey you are getting the hang of it, sweetie," Angie said sipping her morning tea.

Cary had just finished his shower and was coming down the stairs to the kitchen. He was dressed in his made tailored shirt, which covered up his "new" breasts, panties, stockings, and of course, heels.

"You know it is hard enough to walk in these things but these boobs throw my balance off," he said with a laugh.

"You are doing really well though," Angie replied. "Look I know it might be hard but if you wore flats or sneakers, you will be comfortable. Then you'll walk like a guy. With heels, you'll have to think about walking."

"I guess so." He sat down at the table. "I got some questions."

Angie set her cup down. "Ask away."

"Ok, here goes. Where did you get this stuff? And so far except for underwear and these shoes, what am I going to wear? Can't go out like this."

"No, you can't." Angie smiled. "First Alexa knows a trans so she got some stuff from them. Second I grabbed some of your clothing Sunday and using it as a guide, we bought some things. You are about my size so it won't present too big of a problem. Which brings me to the next step.'