A Good Bet

by Lisa Skye

 

Michael lived with his mom in a small apartment - just the two of them. And you could say he had grown into your average twelve year old boy. Well, mostly, that is. Lately though, more and more, he kept wondering what it would be like to be dressed up like a girl - silky panties and bra, sheer nylon stockings, a really silky and lacey slip, and a pretty silk dress. He thought he would make a realistic girl - probably even a cute one!

And it bothered him that he kept thinking about it. He knew it wasn't normal for a boy to want to dress as a girl. But who could he talk to about it? That was the catch. He tried little questions to different people. At a friend's house, when his friend' sister's folded up clothes were sitting on a chair - lacey bras and silk and lace thongs and panties, he asked, "Doesn't it seem weird seeing your sister's sexy underwear like that?"

John looked at him and said, "I never thought of it as her 'sexy underwear' - thanks a lot." He figured asking John if he ever wanted to wear them would be a bad idea.

He asked his mom why boy clothes and girl clothes were so different, and she said that's just the way things happened. And when she asked aren't you glad you don't have to wear frilly dresses and panties, he had to say yes, even if he wasn't glad.

And if she was going out, she might say that men had it easy, just having to throw on a suit. But as she moved around, dressing in her silky lingerie and fancy dress, she didn't seem to be having a bad time. Then she sat at her vanity and worked her magic, turning her already pretty face into a vision of glowing beauty - she didn't enjoy that?

He did often see her clothes around the house, but even though she was a trim and lovely lady, her clothes were still too big for Michael, who was a bit on the small side. So far he had only dreamed of dressing up. His mother had even seen him looking at ads of ladies' or girls' clothes, but thought he was looking at the females themselves. She seem to have no idea, and any little questions he asked just seemed innocent to her.

Then came that wonderful day!

It seemed like any other day. Early August, a nice sunny day. About nine in the morning, Michael had already taken nice long bike ride, and was resting on the porch when he saw the mailman come. He brought in the mail and took it to his mom, and got a soda. He walked back to the living room where his mom was going through the mail. She pulled out a magazine.

"They're talking about Halloween already and it's only August! I sure haven't thought about it yet. How about you, Mikey?"

"Nope, can't say I have." It was true - he may have thought about dressing up, but not for Halloween.

"Let's see, last year you were a pirate, right?"

"Yup, and before that I was cowboy."

"That's what this is saying. It says try something completely different and it should turn out fun."

"Like what?"

"A pirate and a cowboy. Hmmm. I seem to remember a soldier and a cop too."

"Yeah."

"How about a ballerina? Well, that might be too different. Something as a girl though."

"A girl?" Yea, he wanted to shout!

"What's wrong with that? It's just a costume."

"I'm sure I'd look real stupid." He didn't really. And he hoped he'd look good.

"Oh come on now, I'm sure you'd look nice. And not just like a real girl, I bet you'd make a cute girl!"

"I really doubt that."

His mom had been checking him out as they talked. Now she smiled. "Well, I'm so certain that not only will you make a very realistic girl, I'm betting you'll make a cute girl. And I mean a real bet. You let me put some make-up on you, and play with your hair just a little. Then if you can honestly tell me you don't look like a cute girl, you win - something, we'll see. But I'm sure you'll have to agree you see a cute girl looking back in the mirror, and I win a daughter for the rest of the day."

"Okay" he said, "you're on.". Looking back later, he wondered if mom already had a clue, since they never bothered to say what happened if he won. Anyway, he was too thrilled to think about it then. He just followed his mom to her room. She looked at him and pulled what he learned was called a camisole from her dresser. "This will be a little big but will help with the look." He wasn't wearing a shirt them and just pulled it on. His mom smiled at him and sat him at her vanity.

First, she just combed his hair around some. He had light brown hair that comes down a little bit past his shoulders. She showed her satisfaction with a smile and went for make-up. Just a tiny bit of foundation she said, then she put on mascara and eye shadow, a touch of blush and some lipstick. She turned him towards the mirror.

"Oh my God! I'm a babe!" He shouted. Mom laughed.

"I guess you agree that I win the bet. And that means you're my daughter for the day."

"What does that mean?"

"We're going shopping, then lunch, and maybe a movie, with you as my daughter. It'll be fun, no one will know you're a boy."

"They better not."

"You go get washed up - carefully - not messing up your hair or make-up. I'll run to the department store down the street and get you something to wear real quick and then we'll go." She left and he went to wash up.

He couldn't believe this was happening. It was all so sudden. Maybe he didn't answer quick enough the other day when she asked if he was glad he didn't have to wear a dress. But, who cares? This was great! He had to be his mom's daughter all day. Wow!

Mom was quickly back. She brought him silky panties, a padded bra, a girls' top and a purse. Michael changed and put his stuff in the purse, along with the lipstick he was wearing and the perfume his mom sprayed on him.

As they were getting ready to go though the door, his mom smiled at him and touched his arm. "You are adorable, Michelle," she said. "Just relax and I'm sure we'll both have fun."

They started driving towards the mall, and Michael/Michelle guessed his/her silent acceptance was correctly taken as a sign he/she was okay with being a girl.

"So, given any thought to Halloween?"

"To be honest. I had completely forgot about Halloween!"

"But that's how you ended up in make-up in the first place. When we were talking about girl costumes."

"Oh yeah."

"Well, I've proven you make a cute girl, so we'd need a cute costume. Maybe like a princess or bride." Michael/Michelle wisely kept quiet.

A few minutes later they pulled into the mall. First stop was a dress store. Looking openly through the dresses was a new thrill and Michelle quickly won out over Michael. When asked, mom said "Of course we're buying dresses - that's the purpose of shopping!" Michelle got several dresses, as well as a few skirts and blouse.

Then they went to a lingerie store for panties, bra and slips, and nighties. "Only the finest for my new daughter." They made a trip to the car to take most things out, after Michelle changed into one of her new dresses. Time for lunch.

They picked a nice little restaurant and were seated. While looking at the menus, mom asked, "Having a good time?"

Her smile gave away any other answer. "Thanks Mom!" she said. "This is great!"

"We have a while before the movie starts. Want to get out hair and nails done?"

"Really? That would be so cool!" She was feeling brave, and caught up in the moment. "How about getting my ears pierced?"

"Sure, sweetie. That would look nice."

Michelle felt like a princess as they headed into the movie. Long pink nails now graced her fingertips, and her hair was a lovely cascade of soft brown curls. Small pink hearts dangled from her newly pierced ears and were the same shade of pink as her lipstick. A pretty pink silk dress hugged her new curves and swished when she moved. It was all just so lovely!

And her mom was acting like everything was normal! There was a wedding in the movie and when Michelle gushed on about how lovely the bride was, and how beautiful the gown was, her mom just agreed, smiling. "I bet you would make a lovely bride, Michelle," she said. Michelle just blushed, silently agreeing.

During the ride home, mostly what they talked about was the wonderful clothes in the movie, including the wedding gown and bridesmaids' gowns, and also at a big fancy dress party before the day of the wedding.

At home it took a while to get Michelle's new clothes put away. It was around 6:30 when they got home, and close to 8:00 o'clock by the time things were put away. They decided to order pizza and just laze around watching Saturday night crime shows. They changed into matching silk nightgowns and robes they had just bought and settled in to wait on the pizza. Soon it arrived, and as the delivery guy looked at Michelle and her mom in their nighties while Michelle's mom paid for the pizza, his eyes got big and all he managed was a "Wow!"

Michelle's mom giggled out a "thank you" as she paid him, while Michelle blushed brightly. After he left, mom couldn't resist saying, "See, he thinks you're a babe too!" which just made Michelle blush even more, but it did make her feel good.

"Mom, why does that make me feel good? I mean, obviously he was complimenting us on looking good, but still, he's a boy! I have to admit that dressing up like this feels nice, and it's fun fooling everyone into thinking I'm a girl. But I'm still a boy. And I still only like girls. Why does having a boy think I'm pretty make me feel good?"

Her mom just melted at the confused look on Michelle's face. Reaching out to give her a big hug she said, "Oh honey, it means you're human." She gave Michelle a kiss on her forehead. "He complimented us on being pretty, and let's face it, you know you deserve it. Hearing someone say it feels nice. If he had complimented you on making a good move in a game, say, or maybe for drawing a good picture, it wouldn't seem so odd because they're normal to you. Being a girl - excuse me - being a pretty girl is new to you. At the stores today it was mainly other girls seeing you, but here it was just one guy by himself.. And, lets face it," she started giggling, "we're also dressed a little sexier than we were at the mall!"

Michelle had to laugh too. "I guess you're right."

"Of course I'm right. I'm the Mom!" And they laughed some more. Michelle didn't feel odd anymore. Just a girl watching television with her mom.

In the morning it felt so nice waking up in a silk nightgown and panties. But should she change back to boy clothes before going to breakfast? She decided to go down dressed as she was.

"Oh goody, I get my lovely daughter for another day!" Her mom gave her a big hug and kiss. "Good morning, honey."

"Good morning, mom. I wasn't really sure if it was okay to come down like this or not, but I figured at worst you'd just make me go change. Besides, I still have polish on my fingernails and toenails."

"Well, we can take that off easily enough if you really want, but I hope if you do it's just to change colors. I do so love having a daughter around for a change, and I hope you stay dressed up for a while. But don't you feel any pressure to stay a girl - if you want to put back on your boy clothes, that's up to you."

Michelle said with a grin, "I still have lots of new clothes I haven't worn yet."

Mom answered with her own smile, "And there's plenty of stores with new pretty clothes waiting!"

With that out of the way, they had a nice breakfast and talked about nothing in particular. There was mention in the morning paper of renovations that had just been finished at a nearby zoo.

"What do you think, Michelle? Haven't been to the zoo in a while."

"Yeah, that sounds fun. Oh! I can wear that cute leopard print dress!"

Laughing, her mom replied, "You're definitely getting a 'girl' attitude about things."

"You know," Michelle said, "girl clothes don't just feel better, they're funner too. Boy clothes are sooo boring."

"I always thought so," her mom agreed.

Getting dressed, Michelle had leopard print panties and bra to match the dress, with a black silk and lace camisole and half-slip to go in between. Tan two and a half inch wedge sandals finished her outfit, with a matching purse slung on her shoulder.

It was a beautiful day outside. The sun was shining and it was warm without being hot, with a tiny breeze - just enough to cool without messing up your hair. The zoo did look nice. Lots of habitat-style exhibits instead of just animals in cages. Michelle especially loved the big cats, while her mom liked the giraffes best. Both got big laughs at the antics of the penguins.

After a lunch of hot dogs and potato chips they started out with the various bird exhibits. As they walked along, it was obvious Michelle was completely at ease, apparently forgetting all about her nervousness at being caught. As she was gushing on about how pretty the hummingbirds were it struck her mom that it was a shame they hadn't discovered this side of her child before. Michael was a happy child but as Michelle there seemed to be an extra carefree element.

They were going by the raptors now - birds of prey. "You know what I always wondered?" Michelle asked.

"What's that, honey?"

"Most birds just have like sticks for legs, but these guys -" she pointed at a bald eagle, "they look like they're wearing pants, like knickers, then the stick legs at the bottom." With no answer to give, her mom just smiled and shook her head.

They stopped to get sodas, and stepping around the corner of the kiosk Michelle once again showed how comfortable she now felt. Seeing a girl from her class walking up, without thinking she said "Hi, Linda."

As Linda stopped and looked at her with a confused look, she heard her mom softly say, "oh Michelle."

Whether or not Linda heard her, something clicked in her brain.

"Oh my god - Michael!"

Suddenly reality hit. Hard. His name was really Michael, and he was a boy. He was standing in front of a girl from his class and he was dressed up a girl. He was wearing panties and a bra, stockings and wedgie sandals, a half-slip and camisole, and make-up and perfume. His hair was styled, he was carrying a purse and his ears were pierced.

Any second now his life was going to end. Time seemed to stretch out as all kinds of thoughts raced through his brain. Now he could see Linda was going to speak again and a million nasty things flashed through his mind as he imagined what she was about to say.

"You are so cute! Where did you find that dress?"

"Huh?"

"At Lidden's, dear, " his mom quickly jumped in.

"I love it! Michelle, is that what your mom called you?"

"Uh huh," he managed.

"Cool! Do you do this often? Dress up like this, I mean."

"I swear, yesterday was the first time I ever wore a dress in my life. I guess things kinda got out of hand." He was looking down, toes dragging through the sand.

"Really? You were never even a girl at Halloween?"

"Nope."

"That's how it all started," his mom said.

"Yeah. Then we made a bet about if I'd look realistic enough, and things ended up getting carried away. Please don't tell anyone."

"Why should I tell anyone? And I really do think you look great. You can hang out with me anytime."

"You don't think I'm really weird or something for wearing girls' clothes?"

"I don't care. Maybe I'm weird too." She smiled and gave Michael's arm a little squeeze.

Somehow that seemed to set the world back in place.

"Thank you," Michelle said, and she gave Linda a hug.

Their moms hadn't talked in a while and were chatting. Linda said to them, "Can us two go walk through those gardens while you two talk?", while pointing at a nearby area.

"Sure," the moms said. "We'll rest here."

Linda took Michelle's hand in hers and they headed to the gardens. Michelle had always thought Linda was one of the cutest girls in the class, now here she was walking along holding hands with her. Cool!

Linda looked around them, making sure no one was near, and spoke quietly. "Maybe I am getting really weird or something. I have to be honest with you - when you hugged me that felt really nice. And I mean the kind of nice like some really cute guy was hugging me. I know you're really a guy, but right now, like I said, you look like a really cute girl. And I really enjoyed the hug."

Michelle smiled and shook her head. "What can I say about weird? Like you just said, I'm really a guy but I'm all decked out as a girl. And whether you believe me or not, I only like girls, so hugging one of the cutest girls in my class obviously felt nice to me! Not that that was the point of the hug, it was really a thank you hug."

They were walking through a topiary garden, the shrubs shaped into all kinds of animals. At the moment it seemed to be just the two of them.

"Can I ask you a really big favor?" Linda whispered.

"Sure."

"Would you kiss me?"

Michelle's surprise was obvious.

"It's okay if you don't want to."

"Are you kidding?" Michelle quickly proved she did want to kiss Linda.

They walked around the garden some more, still holding hands, chatting about everything. Every now and again they'd make sure no one could see them and kiss again. Soon they headed back to their mothers.

As they walked up to their moms, their moms smiled at them.

"I can see you two are getting along real good, " Linda's mom said. Then she winked and added, " Better fix your lipstick, girls!"

The two blushed and quickly fixed their lipstick.

 

The four of them stayed together for the rest of the afternoon. As they neared the zoo exit they decided to stop together for a meal. Linda begged for Michelle to be allowed to ride with her.

"I must say that you do look very sweet, Michelle," Linda's mom said as they drove along to the restaurant. "And I can tell that your mom is really enjoying having a daughter."

They all had to laugh when Linda added "I'm really enjoying her being her mom's daughter, too!"

"So how long will you be 'Michelle'?"

"I really don't know. This all just kind of happened."

Linda whispered in her ear. "I hope you stay like this for at least a while. I can't really say why, but for some reason I really like you like this. I always thought you were nice, but somehow being a cute girl makes you super nice! I don't know. Like I said, maybe I'm just getting weird."

Michelle whispered back. "If you're getting weird then I guess that means I'm even weirder! And you know what? I don't mind!"

They both giggled. "And to be completely honest, I was really starting to enjoy being a girl even before you showed up. Of course, now it's really really nice!" She gave Linda's hand a squeeze, and gave her a light kiss on her cheek.

The restaurant was nice without being too fancy. It didn't take long for their orders to arrive, and soon their talk mostly died down as everyone was enjoying the food.

"Hey!" Linda suddenly said, turning to Michelle. "Do you have any for plans tomorrow night?" Michelle shook her head and Linda turned to their moms. "Would it be alright if she went with me to my cousin Sheila's wedding?" Quickly facing Michelle again, "If you'd want to go that is," she said, with a very hopeful look.

She could see her mom nodding yes, so Michelle said, "I'd love to."

Linda's mom said, "It sounds okay to me."

"Do you have any other dresses, Michelle? We look about the same size, you could always borrow something from me."

Blushing, she answered. "Mom got me a few things. She was getting carried away with having a daughter."

Michelle's mom smiled. "I have an idea," she said. "After dinner we all head back to my house. Us moms can chat while the girls pick out Michelle's outfit for the wedding."

Linda's mom said, "Sounds good to me."

Not surprisingly, Michelle's room looked mostly like a boy's room. However, on the desk now were a few bits of make-up and jewelry. Opening the closet wide, there were a couple dresses, skirts, and blouses. Linda moved in for a closer look.

She quickly picked out the dress Michelle hoped she'd pick - the lovely pink silk dress she wore for her mother-daughter day. Light pink silk, it came down to about just above the knees, cape sleeves and a not too deep v-neck.

"Wow, this is really pretty! And the dress I'll be wearing is sky blue, so we'll match up nicely. Do you think we'd be going too far if we slow dance at the reception?"

Both of them laughed, and Michelle answered, "I don't know - well, actually it probably would be going a little bit too far - but it sure sounds nice!" Both girls had the same pleasant thought of their two silken-clad bodies gently caressing as they slow danced.

They hung the dress back up before indulging in a little more kissing. This time they remembered to check their lipstick before going back to their moms.

Linda told her mom how pretty the dress was, and how it would match hers. They decided what time Michelle needed to be ready tomorrow and made all their plans. Michelle blushed as Linda gave her a goodbye kiss.

"Well," said Michelle's mom, "that was sure a fun day. And my little girl has a date!" Michelle blushed. "Do you want to get your hair and nails done for the wedding?"

"That would be great. Thanks, Mom!" she said, giving her mom a big hug. She went upstairs to change into a nightgown before settling in to watch some TV. Thinking over the last days, she thought, "Things sure can change quick!"

Just a few days ago she had been wondering how it would feel to be all dressed up as a girl. Now she was not only all dressed up, but about to change into a silky nightgown to watch TV with her mom. And tomorrow she'd be going to a wedding wearing a really pretty pink silk dress, and going as another girl's date!

That bet with her mom was the best bet she ever made!

  

  

  

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