Fun With Aunt Jenny
by: Lisa Skye

 

Robin was in the living room Saturday morning when his mom got the phone call. He could tell it wasn’t something good.

When she hung up she came over to him."Honey, that was my work calling. They’re having big problems at one of our other offices, in another state. They need me to go help out and they really want me to leave as soon as possible. Honey, this might mean a promotion, so I really need to do it."

"That’s okay, Mom."

"I’ll probably be gone for two or maybe even three weeks. Um, I’ll see if you can stay with Jenny til I get back."

That’s how he ended up with Aunt Jenny. She was nice, and really pretty, and he liked her a lot - but they really didn’t have anything in common. And his mom had been in such a hurry they forgot his suitcase.

"You know I love you, sweetie," she said, after his mother had left, "but I really don’t know what we’ll do for a whole week, let alone two or three."

"Yeah, I know, Aunt Jenny. The only times it was just you and me is if we were buying my mom a present or something like that." She wasn’t really his aunt, just his mom’s best friend. But he had always called her that.

"We’ll think of something,"she said, giving him a hug. Hmm, you know, we’re about the same size. And he has such nice long hair. Nah, I don’t think he’d go for that.

"What is it, Aunt Jenny? You’ve got an odd look on your face."

She smiled. "Just an odd thought, Robin. I don’t think you’d go for it, and I don’t want you to get mad at me for thinking it."

"Come on, you know I won’t get mad at you."

"Maybe, but like I said, I doubt you would go for it."

"Well now I’m getting curious. Come on, tell me. It can’t be that bad."

"If you really want to know -"

"Yes I do."

"Okay. I was think that you’re about my size so my clothes should fit you, and you have nice long hair, and I bet I could make you into a cute girl. Satisfied?"

"You’re serious?"

"Sure. It would be something to do, and that we could do together. Ever wonder what you’d look like as a girl?"

"People would laugh."

"It’s only you and me here, honey. And I’d never tell anyone. But, hey, I’m not trying to pressure you. I told you it was just an odd thought." Another, slightly less innocent thought passed through her mind. "And believe me, sweetie, I wouldn’t think any less of you for being afraid to get dressed up as a girl."

"Who said anything about being afraid?"

Jenny smiled. It had just been an stray thought, but now she thought it would be fun. And she thought she had him hooked now. "I guess it’s natural for boys to be afraid of their feminine side. A shame, too. I bet I could make you a really cute girl. But like I said, I won’t think any less of you for being afraid to do it."

"I didn’t say I was afraid, Aunt Jenny. I just don’t want people to laugh at me."

"Like I said, honey, it’s just you and me. And I surely wouldn’t laugh at you. You would be such an angel doing this for me. But like I said before, I don’t want to pressure you into doing something, just because I think it would be fun." There, that would make it sound like he was dressing up as a favor to her.

"I guess I am curious about how I’d look as a girl."

"Let’s do it, sweetheart. I’m telling you, you’ll be a doll."

She took him to the bathroom and got him some Nair. As he got in the shower she took away his boy clothes. She brought him a pair of satin panties and bra, and a matching nightie and robe. "These are for when you get done," she said. "And after you wash your hair with that shampoo, wrap your hair in a towel like you’ve seen your mom do."

Robin didn’t really know what to think. While he had never really even thought about dressing up as a girl, somehow the idea seemed appealing. He looked at the silky undies and nightgown as his body hair went down the drain. I just hope I don’t look stupid, he thought. He washed his hair and after drying himself off, wrapped his hair in a towel like he’d seen his mother do. He slipped on the panties, then struggled with the bra. Finally, it seemed to be on right. Then the nightie and gown. Wow, this really feels nice.

He went to the mirror. No way! I kinda look like a girl already! He wasn’t really sure how he felt about that yet. He left the bathroom and found Aunt Jenny. They went to Aunt Jenny’s bedroom and opened her closet. "What shall you wear, Robin," she asked.

"Wow, that one’s pretty," Robin said, pointing at a purple silk dress. Aunt Jenny pulled it out and held it in front of Robin.

"Oh yes," she said, nodding her head. "I think you’ll be adorable in this, honey. Let’s do your hair and make-up. And you know, I even have some perfect lingerie for that dress. Pretty panties, bra, and slip. I even have the perfect heels for it. I hope your feet match mine, too."

Robin really didn’t know what to think. While he had never dressed up in girls clothes before, and really couldn’t even remember ever thinking about it, he had to admit he liked it so far. It felt nice.

"We’ll do your hair and make-up first. Come sit over here, honey." She sat Robin at her make-up table and turned the chair so he couldn’t see. "No peeking til I’m done. Just wait, though - I bet you’ll be a doll." Jenny set Robin’s hair first. Before starting on make-up she plucked Robin’s eyebrows, "just a little", to give them a little shape. She gave him a complete make-over, and as she combed out his hair she was surprised.

Jenny thought he would be cute, but she was only part right. She was adorable. "Oh honey, just wait until you see yourself! But we have to get you changed first." She got out matching purple silk panties and bra, both trimmed with lace, and a really pretty, lacy purple slip. A waist cinching garter belt and some stockings, and purple high heels. She helped Robin change and led her to the mirror.

"Oh my God, is that me?! Aunt Jenny, I’m a babe!"

"Yes you are, sweetie," she said, hugging Robin. "Even better than I expected. That isn’t so bad, is it? Be honest, honey, isn’t this at least a little bit fun?"

"Yeah, I guess. I’d never have believed I could look like this! And - well, you promise you’ll never tell anyone this, Aunt Jenny?"

"Of course, sweetheart."

Robin looked embarrassed as she,"I have to admit, if I’m gonna be honest, this does feel kind of nice. Well, more than a little." Robin smiled, and twirled around. "To be really honest, Aunt Jenny, it feels fantastic!" Robin gave Jenny a hug. "Thanks, but please don’t tell anyone."

"Don’t you worry, honey. I’d never embarrass my ‘niece’!" She stepped back to look her new niece over once again. "You know, Robin, no one could possibly know you aren’t a natural girl. Please let me take you out to dinner like that. Please! I’ll change into something nice and we’ll be two fancy dressed ladies out for dinner. It’ll be fun. Oh, please, Robin! Do it for me."

Robin knew she looked great, and she certainly wasn’t ready to take these clothes off yet! Like Aunt Jenny said, no way anyone can tell. And I do want to. Why not? "Since it seems to mean so much to you, I guess so. But don’t say anything to give it away."

"Oh, thank you so much, honey. I really do appreciate it." You’re not reluctant at all. Hmm, maybe I do have a new niece. I’m sure I can stretch it out for at least a few days. "Let’s find you a purse to go with that dress. Now, Robin works just as well as a girls’ name - unless you’d like to be called something else?"

Robin appeared to think it over. "Maybe I should have a different name. How about - uh - Lisa? Yeah, that’s a pretty name."

"Okay, Lisa it is. We’ll go to a nice place for dinner. Don’t worry, you won’t be out on display. But let’s be honest, honey, you are one cute girl right now. I’m serious." Lisa was blushing. "No one is going to think that you’re anything but a girl. Now let’s pick out a nice dress for me."

At the restaurant Jenny couldn’t believe how much Robin had become Lisa. And Jenny was pretty sure that Lisa liked being a girl. Needs her ears, pierced, she thought with a grin.

"What is it, Aunt Jenny?"

"Oh, I was just thinking it’s a shame your ears aren’t pierced. Most girls your age have pierced ears, and probably about half the boys."

"True." Lisa paused. "Do you think there’s anyplace we can get it done on the way home?"

"Sure, honey. I’m sure they’ll make you even more adorable." Just look at her blush, and I do mean her.

"I think it’ll be neat."

"It’s in the mall. Right next to a lingerie store. How about if I get you a nice silky negligee as a present for being so wonderful tonight? You can wear it tonight. Would you like that, sweetheart?"

"Oh Aunt Jen, you’re such a doll!" Jenny was only half surprised at how enthused Lisa was.

At the mall they quickly got Lisa’s ears done, then went into the lingerie store. Lisa was almost overwhelmed so her aunt help her find a nice silky, lacy nightie with matching panties (and a strapless bra so Lisa wouldn’t be flat). Lisa almost seemed to be lost in wonder.

"You like this store, Lisa?"

She pulled her aunt close and whispered in her ear,"I never knew being a girl was so much fun!" She gave Jenny a big hug. Jenny hugged her niece and went to pay for her new lingerie.

On the drive home she finally decided to push her luck a little. "Honey, would you like to go back to the mall for some more shopping tomorrow? I’d be just thrilled to buy Lisa some outfits if she’s going to stick around. We can both get make-overs at the salon first, then go shopping. What do you say Lisa?"

"You mean it? Really?"

"Of course."

"Wow. I guess I shouldn’t be saying this but that really sounds like fun."

"There’s nothing wrong with having fun, honey."

When they got back to Jenny’s place, they settled in to watch a little television before bed. Lisa in her pretty new nightie, and Jenny changed into a nice silky nightie too. Wow, what a change a day makes, Jenny thought, gazing at her new niece in her pretty silk and lace nightie snuggled against her watching television, just like a real girl.

In the morning they picked their outfits for shopping. Lisa insisted that they match, at least some. They wore matching pleated skirts, violet for Lisa and pink for Jenny, with lacy white silk blouses. Lisa made sure she had open-toe heels so her painted toenails showed. Jenny fixed her hair and make-up for her, and they were off to the mall.

First stop was the salon. First, Lisa got her hair styled nice, so it framed her face nicely.

"Wow, I love it! This looks great!"

"Thanks, hon. Would you like your eyebrows done? They could use a little shaping."

"Okay," Lisa said without even thinking, and most of her eyebrows were soon plucked out. Next, came the make-over. They gave her a fabulous make-up job. When they were finished and she saw herself, Lisa was speechless. Is that really me?

Jenny had finished and came over. "Wow, Lisa, you are really beautiful! Maybe we should enter you in a beauty pageant," she said with a grin.

"I hate to sound conceited, but looking like this I just might win," Lisa responded with a happy smile.

"Well come on, beauty queen, and let’s do some shopping."

As they walked out of the salon, Lisa moved close and whispered to her aunt. "Aunt Jenny, is there something wrong with me? I like this. I mean, I really, really like this. You know, being all dressed up this way."

"Oh honey, no. You’re dressed in nothing but silky clothes, and how can that feel but nice? And even if we both know you’re not really a girl, you sure look better than about ninety-nine percent of them right now. So you’re having fun with it - where’s the problem?" She smiled at her niece.

"Well, in that case...I want the silkiest, laciest dress we can find in this mall!" She smiled at Jenny. "If we’re going to have fun, we might as well have the most fun we can!"

"It’s a deal, sweetie. We’ll find the prettiest, most feminine dress here - and of course, some matching lingerie."

"Of course!" Lisa said with a laugh.

The search was on for the prettiest dress they could find. Of course, they made plenty of other purchases along the way. Jenny couldn’t get over how much Lisa was getting into it. She seemed as happy as any real teenaged girl shopping for clothes. And she seemed to have very feminine tastes - she wanted everything silky and lacy. And Jenny was happy to go along.

She even got Lisa a jewelry box that Lisa thought was cute. When you opened the lid a little ballerina popped up. Then, of course, Lisa needed some jewelry to go in the box.

Finally they found a dress fit for a princess. Silk and lacy and pink. The skirt was several tiers of transparent pink silk with a lace hem. The sleeves were puffy and sheer, with lace at the wrists. The bodice was tight-fitting, with lace at the bust. It was beautiful and they both just looked at each other without saying a word.

"Lisa," Jenny said, after thinking a moment, "you want to look your very best in this dress, don’t you?"

"Oh yes!"

"Come along then, we need to go somewhere. I think for this dress we should get you a corset. It’ll give you a little less waist and a little more cleavage. What do you think?"

"I hope they have a pink one to match the dress!"

They did. Also some cute pink panties, stockings for the garters on the corset, a lacy pink slip, and then a cute pink nightie, just for fun. Lisa wore the corset as they left the store. After Jenny laced her in she had a great figure.

"Next some cute pink heels, then we can go try on the dress."

"Aunt Jenny, you’re the greatest!" Lisa said, giving her a big hug. "This is so much fun! I never would have thought so, either. Hmm, Aunt Jen, that dress is really gorgeous. Where can we go that I can wear it?"

"We’ll come up with something, sweetie. Here’s the shoe store." They found some nice pink heels, and also some others. Now they were ready to try on the dress.

Fresh from a make-over, wearing the corset and her cute new pink high heels, Lisa was an absolute dream in the pink silk dress. It was as if the dress was made for her. The tight bodice hugged her now quite shapely curves, lace at her cleavage. The tiered skirts with lace-edged slits revealed Lisa’s shapely silk covered legs perched on four inch pink high heels. Her curly hair tumbled onto her bare shoulders, and at the end of the long puffy sheer sleeves ending in lace, her fingernails matched the pink of the dress. A darling little angel.

"Oh, Lisa, we’ll definitely have to take you out somewhere. Just look at you!" In fact, she had to talk Lisa out of wearing the dress home. Reluctantly she changed back into her skirt and blouse and they headed home.

A little later that evening, just after dinner, Jenny got a call from a friend of hers. "Hmm, how about tomorrow night? I have someone you and your daughter can meet. She’s just about Kimberly’s age. They might have fun. Okay, Sandy, bye."

"Well, Lisa, now you have somewhere to wear your new dress."

"Ooh, where Aunt Jenny?"

"That was Sandy, a friend of mine. She has a daughter, Kimberly, who’s your age. Well, Kimberly loves to get all dressed up - in fact, she is a beauty queen - and she wanted to have a fancy dinner. So tomorrow night you can wear your lovely new dress. Not sure what I’ll wear, though."

"Cool! Will we go back to the salon? I want to look this good again."

"We’ll see, honey," Jenny answered with a smile. Wow, she’s a girl, she really is. What will her mom say?

The next day Lisa couldn’t wait for the dinner so she could wear her new dress. "Tell you what, honey, if you want the time to go by you have to keep busy. You can help me clean the house. That’ll make time go by quicker."

"That’s no fun," Lisa said with a mock pout.

"Come with me, sweetie, and I think I can make it a little funner for you." She took Lisa by the hand and led her to her room. She dug in the closet for a minute. "Here, we go. I wore this to a costume party last year. A very nice and sexy french maid’s outfit."

A short silky black dress, with layers of silky, lacy petticoats. And four inch stiletto heels. Black silk stockings. And of course, a frilly apron and cap.

"What do you think, Lisa? Will this make cleaning any funner?"

"But Aunty, where’s my feather duster?" She smiled as Jenny pulled one from the closet. Soon a very cute little maid was dusting the house, petticoats rustling as she pranced happily along on her stiletto heels. In no time at all it seemed, the house was clean and it was time to get ready for dinner.

While her aunt was doing a very nice job on her make-up and hair, Lisa asked, "Do they know, Aunt Jenny? You know, about me?"

"I haven’t told them. That’s up to you. But you look completely like a teenage girl, honey, no doubt about it. A cute one, I might add."

"I guess we’ll just see what happens."

Judging by their initial reactions, they didn’t guess. The four of them were sitting in the living room, all in beautiful dresses. Dinner wouldn’t be for another hour or so.

"Have you ever been in pageants, Lisa?" Kimberly asked. "I bet you’d do well. And that dress is gorgeous!"

Lisa blushed. "No, I never have."

"Ever thought about it? I really mean it - I think you’d do well."

Lisa blushed again. "Uh, I think there’s something I should tell you. Um..." She looked at her aunt.

"My friend had to go out of town suddenly for work, and so she left Lisa with me. We were wondering what we could do and I had an idea. It did work out fine." Jenny and Lisa smiled at each other. "You see, my friend dropped off her son Robin." She waited just a second for them to catch on.

"Oh my god," Kimberly said, "you’re a boy? No way! You’re too cute."

Lisa blushed and nodded. No one seems upset, she thought. So far so good.

"This is so cool," Kimberly said. "Uh, Lisa, do you still like girls?"

"Oh yeah," Lisa said with a grin. "I never did this - dressing up as a girl - until Aunt Jenny brought it up. But I have to admit, I am having fun!"

Sandy said, "I never would have guessed. You are a little doll!" She tactfully ignored Lisa’s blushing. "Kimberly is right. Maybe you could do well in a pageant. You know, I don’t think the rules actually say contestants have to be female. It’s just assumed that they will be."

"What do you think, Lisa?" Aunt Jenny asked. "Would you like to try it? Might be fun?"

"Are you serious? I don’t know about that. People would know, I’m sure."

"You’d get to wear lots of silky, lacy dresses and gowns."

"Well, that would be nice," Lisa said, smiling.

"I thought you’d like that part, sweetie."

"Come with me tomorrow, Lisa, and watch the pageant I’m in. See what you think. This is a finals round, ten girls left. We’ll be doing fancy gowns and fancy dresses. Pretty girls dressed up in silk and lace. Don’t you want to watch that?"

Lisa grinned. "Well, since it seems to mean so much to you, okay." She and Aunt Jenny exchanged smiles. "Is it okay, Aunt Jen?"

"No problem, honey."

The talk turned to other things and soon dinner was ready. As they ate the talk slowly drifted back to pageants and pretty clothes. Kimberly said, "Going in a pageant sounded like fun because I’ve always loved dressing up." She smiled at Lisa. "Have you always liked dressing up like this, Lisa?"

"Saturday was the first time I ever wore girl’s clothes, or ever really thought about it. But I have to admit I do love it. It feels so nice! It’s weird, I guess, but that’s how it is."

"I don’t think it’s weird," Kimberly said, "I think it’s great. Well, I guess I can’t honestly say it’s normal, but I do think it’s great. And you look fantastic!"

"It was my idea, " Jenny said, "But I doubt either of us thought it would go this far. Of course, I just adore my pretty new niece. Such a doll!"

"Hey, Lisa! Would you like to come see my gowns? I have lots of really nice dresses." They got up and she took Lisa’s hand to lead her to her room. "This is so cool. I never got to show a boy - sorry, Lisa - my pretty clothes!"

Kimberly had two large walk-in closets in her room, both filled with dresses and gowns. Lisa was awestruck. It was as if she had entered a beautiful new world. "You look just perfect in that pink dress, Lisa. But maybe another time when you come over, and we’re not already dressed so nice, you can try on some of them and we can have our own little pageant."

"Wow, I think I’d like that." She had a thought that she didn’t say out loud, but it still made her blush.

"What is it, Lisa? I see there’s more. Don’t be shy."

"Um, I was wondering if you had pretty slips and all to go with them," she managed to say.

Kimberly said, "Look. That’s what these drawers are." Lisa saw drawers full of silky, lacy lingerie. Kimberly saw her eyes get bigger and smiled. "Tell you what - I’ll show you mine if you show me yours," she said with a big grin.

"Uh, my what?"

"You’re undies, silly," Kimberly said. "Are you wearing pretty lingerie?" Lisa nodded. "Well, I’ll show you mine if you show me yours. We can help each other with our dresses. What do you say?"

"Okay. But you first."

"I’ll take off my dress and then you take off yours. We’ll both be in slips, okay?"

"Okay." Lisa helped Kimberly off with her dress, a cute dark green silk dress. Underneath she was wearing a slip the same shade of green, with lots of lace at the hem and bust. She blushed slightly when Lisa gave a little whistle. Then she helped Lisa take off her gorgeous pink dress, showing off her cute pink slip.

"Pretty, Lisa." Lisa smiled at her, then leaned over and kissed her on the cheek. Kimberly hugged her and said, "You’re so sweet, Lisa. You’ll have fun tomorrow. Most of the girls are nice, and everyone is dressed up pretty."

"How should I dress? I don’t really have a lot of dresses," Lisa said.

"I can lend you something! Let’s look. And you’re in your slip now so you can try on what ever we pick."

They tried a few dresses and were soon satisfied. They helped each other put back on their dinner dresses and went back downstairs. Soon it was time for Jenny and Lisa to leave.

On the ride home they talked. "You know Aunt Jen, this is kinda weird. Right now I’m not sure if I’m more excited about seeing a bunch of really pretty girls all dressed, or about seeing their pretty clothes." Jenny laughed along with Lisa.

The day at the beauty pageant was a blast. Lisa was thrilled by all the gorgeous clothes, and just as much by the beautiful girls. When she met them after the show they all seemed pretty nice. And Lisa was happy that all their chatting was about the shows, and clothes, and not about boys. Nobody seemed to suspect there was anything different about Lisa, or at least they didn’t say anything.

Not surprisingly, she dreamed that night of walking down the runway in her crown, wearing a beautiful white silk and lace gown.

The next day, Wednesday, they didn’t have any plans. While watching the television Lisa talked about the pageant, and all the dresses and gowns. How fun it seemed. Jenny said, "I"ll tell you what, honey. I don’t have a closet filled like Kimberly’s, but I have some really nice clothes. You can put on a fashion show for me."

Lisa had a fabulous fashion show! She went through Jenny’s closet and soon had her aunt joining in. They even changed their make-up several times. Lisa was already getting pretty good at it.

She was sitting in a slip at the vanity, face cleaned and ready for new make-up to match the dress she would put on next. As she was putting on mascara she stopped and looked in the mirror, then turned to her aunt. She started to say something but stopped and said, "No, let me finish this first." Turning back to the mirror she finished doing her eyes, then some blush and lipstick. She fluffed her hair out a little and smiled at the pretty girl looking back from the mirror. Then she turned back to her aunt.

"Okay, look at me Aunt Jenny." Lisa crossed her legs and smoothed out the lacy hem of her slip.

"Honey, you are one cute girl."

Lisa smiled and only blushed the tiniest bit. "Right. So how can I ever go back to being a boy? And what will my mom say?"

"I really don’t know. I wasn’t thinking ahead. I guess we have about a week or so to think about it."

"Yeah. So for now I won’t think about it either. Hand me the dress, Aunt Jenny." Her aunt helped her into it and she stepped up to the big mirror. And for now, I’m a babe!

But Lisa’s mom was actually on her way back, temporarily. She had already straightened out most of the problems, and was coming back for a day off to spend with her son. She had to go back for another week or so to settle some things. There was even talk of promoting her and putting her in charge out there. She wasn’t sure though. What would her son think about moving, where he wouldn’t even know anyone?

It was late when she got in, and since she wanted to surprise them she hadn’t called, so she decided to go home and go to bed. She’d see them in the morning.

Thursday morning Aunt Jenny realized they had never picked up the suitcase that had been forgotten in the beginning. "We’d better go get it so whenever your mom does come home she doesn’t wonder why it’s there. Janis said she’d be gone at least a week and it’s almost been that long."

"Yeah, I guess we better get it. Hey, can I borrow that light green dress?" They got dressed for the drive over and Jenny let her niece borrow the green silk dress and a slip that matched it nicely. She had green panties and bra of her own that matched nicely that her aunt had bought her. Also her own were the stockings and heels, and cute dangling earrings in her pierced ears. It was the first time she was a girl in her own house.

Janis walked by her sons room and noticed the suitcase. So what’s he been wearing the last couple days? Just then she heard the front door opening. She heard Jenny speak first and she stopped.

"Is there anything you want to get besides the suitcase, Lisa?"

Lisa?

"I don’t think so."

Sounds kind of like Robin, but like a girl.

"I have an idea," Lisa said. "Why don’t we leave it here with a note saying I don’t need it because I’m a girl now?"

Janis stepped into the hall. Jenny must be in the living room still. Janis saw a girl with her back to her, long curly hair on the shoulders of her pretty green silk dress. Waving her hands as she spoke again, Janis saw long red fingernails on the girl’s hands that matched the red toenails under stockings she saw looking down at the girl’s high heels.

"Being here really makes me wonder what Mom will think or say." Lisa turned around to go get the suitcase.

And saw her mom.

"She’d say you’re a doll, sweetheart. And I’d be happy to have a daughter."

 

 

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© 2001 by Lisa Skye. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.