Snowed in with Aunt V Ch. 02

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Aunt V catches Kelly in a dress.
4.2k words
4.55
25.9k
43

Part 2 of the 7 part series

Updated 06/14/2023
Created 01/24/2023
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Kelly took a big gulp of his drink, then set it on the dresser in Madi's room. He started opening drawers, checking the contents. He was happy to find a drawer full of sexy panties! He quickly stripped off his clothes and felt the stirring in his dick as he pulled the nylon bikini briefs up his legs. He so wished he could shave his legs, but was glad that his body hair was very light.

In another drawer he found some bras. His fingers shook as he looked through them. Some of them were from when Madi was just starting to grow tits and had small padded cups that wouldn't hang on his chest like the big D-cup bras he found in his mother's drawer. He picked out a pretty pink bra with lace around the cups and quickly hooked it around his chest and put his arms through the straps.

He looked through other drawers, looking for a full slip or pantyhose. He found some old pantyhose, the cheap kind. He looked through them and found a pair of sheer black hose and tossed them on the bed, just in case he couldn't find any better ones. But he still wasn't finding a full slip. Madi had left behind several half-slips, all white, but no full slips. He would deal with that later. He knew Aunt V had pretty full slips. He started to wish he'd taken the pretty blue one off of her when he was putting her to bed.

Kelly stepped into Madi's walk-in closet and inhaled. The closet smelled like girl, like the fabrics used for dresses and nice blouses and pants. Madi had left behind almost a full rack of dresses. Kelly's fingers were again trembling as he thumbed through them. He gasped with pleasure when he found, near the back of the closet, several of the formal gowns Madi had gotten for various events when she was in high school. It made sense that she wouldn't take them to college with her.

He pulled one of the gowns out, hoping he could fit into it. Madi was not fat, but she was a big girl, an athlete. She played basketball and softball in high school, and now was on the basketball team of a mid-major university. At the same time Kelly was small for a male, always had been. Madi's bra and panties fit him, so why not the dress?

He sat on the bed and put the black pantyhose on first. He had always hated when girls wore panties with pantyhose, but he kept the panties on under the hose. He pulled the hose up and smoothed them over his legs. They weren't bad. They fit him nice and tight and held his rather small package in place, and the hair on his legs was barely noticeable. But they didn't have as much lycra in them as he liked, like the ones Aunt V was wearing.

He unzipped the back-zip dress and stepped into it. It was a strapless dress that fit tight around the chest. It had a built-in underwire that was meant to push the boobs up and together to form a cleavage. Kelly figured out that the dress would look better without the bra, so he took it off and tossed it on the bed. He struggled with the zipper. He knew that when Madi wore the dress Aunt V or one of her friends zipped it for her. But he didn't have someone to zip it for him, so, with the corset-like bodice of the dress down around his waist he zipped it up and then started trying to pull the cups up in place.

The fabric was luxurious, and soft, silky material over the hard stays of the bodice. The corset-like portion of the dress ended just above his hips, giving way to a long, luxurious skirt. When Kelly got the cups in place he reached in and pulled his soft pecs into the cups. He looked in the full length mirror on the closet door and gasped. It looked like he had boobs! He had a cleavage!

He dug around in the boxes in the closet and found the heels that matched the dress. They were sling-back pumps with two inch heels... shoes that would be easy to dance in at the prom or winter formal. Kelly walked back and forth in the bedroom, enjoying the feeling of walking in heels again.

Before the twins were born, when Kelly had a lot of time alone at home, he had often walked around the house in a pair of his mom's pumps or strappy sandals. Sometimes he wore a dress over the slip, bra, panties and hose he took from his mom's hamper or out of her drawer, but usually he pretended the slip was a fancy cocktail dress. This was the first time in his life he had put on an actual evening gown, complete with matching shoes. He felt elegant! Classy! Sexy! Most of all he felt Pretty!

Kelly loved to feel pretty. He was often jealous of the girls at school. They could dress down and wear jeans and a t-shirt like the boys wore. Or they could dress up and put on a nice blouse and some heels and jewelry with the jeans. Or they could go all out and wear a cute dress. All of this just for school!

Boys, on the other hand, were stuck with jeans and a t-shirt. Some times for special occasions they might wear a nice Polo with some khakis. But it was always the same shoes and for jewelry, probably a wrist watch.

Girls could put on make-up and paint their nails. Boys- no make-up, no nail polish.

One of the things Kelly envied most about girls was wearing dresses, although most girls didn't wear them except on special occasions. The thing he envied second most was the nails. And then the make-up.

Just recently a girl at school, a friend of his, came to school wearing a pair of boy-style jeans and a sports team t-shirt she'd probably borrowed from her brother. But she had just a hint of shadow on her eyes, just a hint of blusher on her cheeks, and a pale pink lipstick on her lips. Her hair was pulled back in a ponytail, and she wore dream-catcher earrings that dangled from her pierced lobes. Of course, her fingernails and toe nails were painted a pink that was just a few shades darker then her lipstick, and she wore cute sandals with a one-inch heel. Kelly both loved her and hated her that day. And later, towards the end of his senior year, he told her so, and why!

But tonight, walking around in Madi's sexy dress and sexy heels, with the slit in the side of the dress revealing his leg all the way up to mid-thigh, he felt PRETTY. Even without make-up and dangly earrings and painted nails, he felt pretty.

He drained his drink and walked down the hallway to the bar to mix himself another one. He wasn't worried about Aunt V waking up and surprising him. But still he tiptoed up the other hallway to her open door to listen to her breathing. He'd heard that breathing before. When his mom had imbibed a bit too much at a party. He knew she was out for the night.

He walked back to the living area and felt the need to walk outside. He opened the big front door. It was still snowing, even harder now than when he and Aunt V came home earlier. He looked at the clock. Was that less than two hours ago? It was cold, but he wanted to be outside. He went back to the bar where Aunt V had left her purse. He took one of her 120 cigarettes and a lighter and stepped back out on the front porch. He made sure the door was unlocked before he closed it. He stood on the porch shivering in his sleeveless dress and heels. But he still felt elegant as he puffed on the long thin cigarette.

When he was done smoking, Kelly went back in the house, grabbed his drink and headed back to Madi's closet. She had so many cute and pretty dresses he didn't want to limit himself to wearing just the one. This was probably the only night he'd have this freedom, so he wanted to take full advantage of it.

He shimmied out of the gown and laid it on the bed. He put the bra back on and went back into the closet. He picked out a dress Madi might have worn to school. It was a pullover tank dress- the top was built like a tank top with wide straps over the shoulders. There was a light elastic band around the waist to separate the top from the skirt. The skirt flared out and reached almost to his knees.

He decided the heels weren't a good fit for this dress, so he went back in the closet and looked through the shoes Madi had left behind. My goodness, how many dresses and shoes did this girl have? He found a pair of flat sandals. The straps that went over his toes and stretched up to the straps around his ankle had different colors of beads on them. He liked the look! Well, except for that his toe nails weren't painted, and he knew Madi would never wear these shoes with reinforced toe black pantyhose. But he didn't want to take the pantyhose off, so he didn't.

He didn't feel elegant, but he felt cute and pretty! Again he walked around the house, enjoying the freedom that he would have only tonight. Madi was supposed to be here tomorrow, and Aunt V wouldn't drink too much and crash so early in the evening ever night. He thought about taking another of Aunt V's cigs and going out on the front porch again. But it was cold, and he wasn't really a smoker. So he refilled his drink and just walked around the house.

Back to Madi's closet to look at her dresses again. As he was moving the hangers to look at each one he found THE dress. It was made of a soft, silky material. Kelly wasn't sure what it was, but he knew it would feel good against his skin. The dress was a typical dress that Madi might have worn to school, or on a date, or just about anywhere that she wanted to be dressier than jeans, but not too dressy. It was light colored, but had a multi-color pattern of random size stripes and swirls.

Kelly didn't know why, but he knew he had to wear this dress. He went back to the bed and pulled the dress he was wearing over his head and tossed it on the bed, then pulled the new dress over his head. He smoothed it down, then went to the full-length mirror. He smiled when he saw his reflection. He twirled around, watching in the mirror how the skirt swirled around his legs. He wished it didn't have the cap sleeves that showed glimpses of his hairy arm pits when he moved. He so wished he could shave his armpits!

He immediately started trying to figure out a way to get this dress hidden in his bag to take home with him. It obviously wasn't one that Madi wore often. After all, she didn't take it with her when she went away to college.

Kelly walked around the house. He went to the bar and refilled his glass again. He loved how the dress moved, how the skirt brushed against his legs when he walked. He loved how he felt wearing the dress. And he hated Madi because she could wear this dress any time she wanted, but she left it behind, basically discarded it, and he could only wear it because his aunt had enjoyed a little too much holiday cheer.

Kelly wasn't a drinker, so the alcohol he had consumed was having an effect on him. He was hating his cousin. He was hating his lot in life, to be a boy who so loved the soft, feminine, pretty clothes she could wear. He hated that she could also choose to wear the very clothes he'd had on when he arrived- jeans and a t-shirt and athletic shoes.

He went back to the bedroom and sat on the edge of the bed. He knew he should put all the pretty dresses back in the closet, and the pretty bra and panties and hose back in the drawer. He knew he should put his boring cotton underwear back on, and a pair of the shorts he would sleep in, and get in bed to sleep off this nice buzz he was feeling. He was going to make himself get up and do all of that. In just a minute. He took a sip from his half full glass and set it back on the coaster on the dresser.

* * * * * * * * * * * * * * * * * * * * * * * * * * * *

Kelly rolled over in bed, trying to open his eyes. He got them open and looked around. Where was he? He looked more as he stretched. Oh, yeah. Madi's room. She wasn't home for the holidays yet, so Aunt V had told him to crash in her bed. He lay back and smiled as he remembered helping her take her boots off, how he had sniffed her musty feet and looked directly at her dark triangle of hair under her semi-sheer pantyhose, how he'd leaned over to inhale the musky scent coming from the crotch of her hose.

He remembered going to Madi's room and looking through her drawers and in her closet, and trying on her cute dresses and shoes. And then he sat up in bed, eyes wide open and looked down at himself. He was still wearing that last dress, and the bra and panties and pantyhose!

He jumped out of bed and looked around. He was no longer wearing the pretty sandals. The other dressed were no longer draped across the foot of the bed. Had he put them up? The last think he remembered was sitting on the side of the bed, sipping his drink and trying to make himself put Madi's things away and put his own clothes back on. But he obviously hadn't done that last part. So had he done the first part?

He looked at the dresser. His half empty glass was gone. In its place was a small pitcher of ice water and a clean glass. The comforter on the bed was pulled back and had been spread over him as he slept. He walked to the closet. The two dresses he'd left on the bed were hanging near the door, and the sexy heels and pretty sandals were set neatly on the floor under them. And on the end of the bed lay a coral colored t-shirt, obviously a woman's shirt with an applique of clouds on the front, and a pair of matching pajama pants.

He realized that Aunt V had come into the room while he slept, that she had seen him sleeping in the dress and hose. He realized that she must have taken the sandals off of his feet and put them and the dresses away, and she had taken his glass to the kitchen. And she had left him the t-shirt and pants to put on when he woke up.

He looked for his clothes, the ones he'd taken off when he changed into Madi's things. He looked on the floor, where he knew he left them. He looked on the bed. He looked under the bed. They weren't there. And his bag containing the rest of his clothes was in the den, where he originally thought he'd be sleeping. To get to his bag he would have to walk up the hallway and pass the kitchen.

He poured himself a glass of water, then walked to the bedroom door to listen. He could hear the faint sound of a tv. His only hope was that Aunt V was in her bedroom watching tv. But... she could be in the kitchen, sitting at the bar having coffee and watching the little tv there. Or she could be in the living room on the couch, watching the big tv there. Either way he would have to walk past her to get to his bag.

With trembling fingers he pulled the dress... THE dress... over his head and dropped it on the bed. He unhooked the bra and dropped it on top of the dress, then pushed the pantyhose down his legs and sat down to take them off. As he sat on the edge of the bed with the pantyhose still bunched around his knees, he considered that he should just leave them on. He loved wearing pantyhose. Aunt V knew he was wearing them when he went to sleep. Why not just leave them on and enjoy them? But he couldn't do that. He pushed them down his legs and pulled them off of his feet.

He reached for the t-shirt and pants Aunt V left on the bed for him. He held them, looking at them, and gulped down the water. He took a deep breath and put the t-shirt on. As he pulled it down and smoothed it over his torso he noticed that it was much softer than his own t-shirts. He glanced up at the mirror on the closet door and smiled just a little. It was just a t-shirt. But with the V-neck and the pretty clouds it looked feminine. He took another deep breath and refilled his water glass. He sat back on the bed and gulped most of the cold liquid down. Kelly had never had a hangover before and didn't understand why he was so thirsty this morning. He set the glass down and reached for the pants. He held them up and looked at them. They had some light swirls of color that matched the applique on the shirt. They had an elastic waist. And Kelly noticed that they did not have the opening in front, like men's pajamas had. These were definitely women's pants!

He pulled the pants on and stood to pulled them up around his waist and looked in the mirror. And smiled. It was pants and a t-shirt. But he looked slightly feminine... maybe even pretty. But he couldn't hide out in Madi's bedroom all day. He would eventually have to go to the other room, to face his aunt. That wouldn't be so hard, would it? After all, she had seen him in the dress and pantyhose. She had probably (he still wasn't for sure what all had happened) taken the pretty sandals off of his hosed feet. And she left the pretty pajama set on the bed for him. So she wouldn't be shocked or even surprised when he walked into the kitchen wearing them.

Kelly picked up the water pitcher and glass and headed for the door. But he stopped just short of actually stepping out into the hallway. His hands were shaking. His stomach felt a little queasy. Kelly wasn't sure if that was from the fear of appearing in front of his aunt wearing her pajamas or from the alcohol he had consumed last night, or a little of both.

He took a deep breath and stepped into the hall, out of protection of the bedroom. He slowly walked toward the kitchen wondering what Aunt V would say to him. He listened closely to make sure there was no one else there.

Aunt V looked up and smiled when she heard him. She was sitting at the bar with a cup of coffee, looking at her phone.

"Well, hello, sleepyhead!" she said brightly. "I was beginning to wonder if you were going to sleep all day!"

"What time is it?" he asked, his voice rough.

"It's after 9," she told him. "Are you a coffee drinker? I just made a fresh pot."

"No, thank you," he told her, his voice starting to smooth out some. "Um, do you have any orange juice?"

She stood up from the bar stool and stepped to the refrigerator. Kelly put the empty water pitcher and glass on the counter near the sink. He noticed that his aunt was wearing pajamas that were very similar to the ones he had on.

Aunt V grabbed the glass and filled it with orange juice. She noticed that her nephew had not looked her in the face since he entered the room.

Kelly took a sip of the juice, then drank most of it down. "Thank you," he said. "And thank you for the water you left for me."

Aunt V smiled. "You're welcome, dear. Um, Kelly? How do you like the pajamas?"

He blushed and still didn't look at her. 'They're great and I love them!!!' he wanted to yell. "Um, they're fine," he said. "Thank you for leaving them out for me. I couldn't find my clothes. I thought I left them in there where I slept, but..."

"I put them in the hamper," she told him. "I thought you might like those better for lounging around this morning."

"Thank you," he said again as he started to walk towards the den to get his bag.

"Where're ya goin'?" V asked him.

"Um, I thought I'd grab my bag for when...." he didn't finish. For when what? He wasn't sure.

Aunt V set the orange juice on the bar, then sat back on her stool with her coffee. And asked Kelly that very question. "For when what, dear?" she asked softly. "For when you feel like you need to get dressed for the day?"

"Um, yeah, something like that," Kelly answered. He had stopped walking, but still had his back to his aunt. He thought about it and realized that he wasn't that uncomfortable talking with his aunt while wearing her very feminine pajamas.

"Why don't you come sit down and let's talk for a bit," Aunt V said softly.

"Do I have to, Aunt V?"

"Of course you don't have to. But think you should. Are you feeling embarrassed? If you are, that's ok. I'm a little embarrassed about how I acted last night, too."

Kelly's head and shoulders slumped. Suddenly all that had happened came rushing back to him. The drinks, walking around in his cousin's dresses and wearing her underwear, passing out fully dressed in a dress and bra and hose and panties, his aunt coming in and making him comfortable as he slept, and putting away the clothes he had been wearing, and leaving the pretty pajamas for him, and....

It was too much. He didn't want to cry. But he couldn't stop it.

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