Being Helpful is Good

by Lisa Skye

 

Sam was in his bedroom, just hanging out. It was Saturday morning, middle of the summer. He was leafing through a magazine, but not really reading much. The radio was on, but he wasn't really listening much. Sam was thirteen, and just hanging around, not really doing anything, seemed to be his main hobby these days.

He decided he could use something to drink, even if it meant getting his lazy butt off the bed. He got up and left the room, down the hall and down the steps. As he walked through the living room his mom said, "Oh there you are. I was just about to come up. Are you doing anything right now?"

"Nah, just hanging out. I just came down for a soda."

"Well, can I ask you a big favor?" she said with a grin.

"Uh oh, what now?" Sam was a good kid even if he liked just hanging around doing nothing, and was always ready to help out his single mom. However, his mom most definitely had a very odd sense of humor.

"I'm hemming Janine from next door's dress, and it's hard to make sure I have it straight unless it's being worn. You're just her size, and it would be a really big help if you put it on for me. I promise I won't tell anyone."

"Oh mom, I'd look ridiculous!"

"It's not like you'll be walking around in public - just you and me here. And it would really help me out a lot."

"You better not laugh!"

"I promise. Let's go to my room for the dress." His mom's room was down the hall from his, so up the stairs they went. As they entered her room Sam noticed the flowery smell. She opened her closet and pulled out a silky green dress. "Isn't it pretty?" his mom asked. Sam had to admit it was a pretty dress.

She hung it on a hook on her closet door and went to her clothes drawers. She pulled out a slip and a pair of panties.

"What are they for?" Sam asked, sure he already knew.

"The dress won't hang right without them."

"Do I really need to?"

"What's the big deal? They're only clothes. They won't bite. You may even admit they feel nice once you have them on."

A moment later he was wearing his mom's silk panties and stepping into the slip. His mom adjusted the straps and said, "See, that didn't hurt!" He managed a smile and she helped him into the dress.

As she zipped the dress up and Sam was all covered in silk, he thought, this does feel kind of nice, but I'm not admitting it.

It took a little while for her to get it all pinned, and by the time she was done, she could tell her son was not minding the clothes he was wearing at all. While it would be some easy fun to tease him a little bit, she did think he looked so cute she wondered if she could get him to stay in a dress.

"I'm almost done, honey. That wasn't too bad was it? Girl clothes aren't too terrible, are they?" She gave him a little pat on his behind. She was guessing he didn't want to admit it felt nice, but he didn't want to lie and say it didn't.

She stood up and carefully helped him out of the dress. Sam's mother was a small lady, and her clothes seemed to fit him nicely. As she hung Janine's dress back up she said, "A little later I'll need you to wear it again after I finish sewing so I can check it. I have a dress very close to this one you can wear until I finish sewing. Okay?"

Sam merely nodded and his mom got a dress from her closet. This one was also silk, but blue. It'll match your blues eyes, she told him. Sam smiled at her comment but was playing it safe by staying quiet. Then he surprised himself by asking, "How come you didn't have me wear a bra?"

His mom answered truthfully. "It wouldn't really matter for the hem, and I figured you'd really fight wearing a bra." She smiled and added, "I'll get you one if you want."

"No, no," Sam quickly said. "I just wanted to make sure everything would be right. I mean, Janine does wear a bra."

"When we check it out after I'm done sewing we'll have you in a bra, then everything should look right. Hmm, we should probably try some heels too. I think you'll fit in my shoes."

Sam didn't say anything, just headed back to his room. He couldn't believe he pretty much just volunteered to wear a bra! These girl clothes were messing with his head. They did feel nice though. And if he wore heels, he'd probably need pantyhose or stockings. He wondered what they would feel like. In his room he sat down carefully so he didn't wrinkle up his dress.

Downstairs his mother was just wondering if she'd have to fight with Sam to wear stockings so heels would fit. She smiled as she figured there would be no problem. Just as he easily agreed to another dress while she sewed this one, she was guessing he'd easily agree to stockings. Soon she finished sewing and headed back upstairs. She called to Sam and headed for her room. She already had a bra and thigh high stockings out as Sam walked in.

She unzipped the dress he had on and helped him out of it. Lowering the top of the slip, she soon had him in his bra, and adjusted all straps. She put small pads in, saying "You're too young to be any bigger," with a grin.

Sam was already feeling braver. "Don't pick on me because I'm underdeveloped," he quipped, sticking out his tongue.

His mom giggled, then showed him how to put on the stockings. They felt so nice he couldn't help saying so. Then back into the slip, and mom again helped with the dress. After zipping him into it, they found her heels slipped right on.

She had him turn slowly, and walk around a bit. Everything looked even and good. And Sam was just too cute, his mom thought. Could she get him to let her make him up?

"Thank you so much, honey. You have been a really big help." Sam was looking at himself in the full length mirror on her closet door. She smiled as he turned to check himself out from all angles. "And you probably don't want to hear me say it, but you do look adorable right now."

"I can't believe how much I look like a girl. All that's missing is make-up and I'd probably be a cute chick." Sam sounded amazed.

"I'm very good with make-up, in case you haven't noticed," mom joked

"People would really laugh."

"Just you and me here, honey.".

"You think it's alright?"

"Why not? I think it'll be fun. Let's see how pretty we can make you!"

"Okay!"

It felt nice as his mom gave him a makeover. Brushes tickled his face as she went to work. The only thing he didn't like was when she plucked a few eyebrow hairs. His hair wasn't that long but his mom combed it around some, and when he looked in the mirror finally, he was amazed.

"Mom! I'm a babe!"

His mom laughed. "Yes, you came out looking even better than I thought."

"This is kind of cool. Pretty weird, I guess, but somehow it still seems cool."

"It would be nice to have a daughter around sometimes," mom said smiling.

"Hey, I didn't say I was gonna keep dressing up like this!"

"Oh, sorry, I thought that's what you meant. Don't you think the clothes feel nice?"

"Yeah, but -"

"Don't you think it's cool that you can look like a really cute girl, a babe as you said?"

"Yeah, but-"

"I don't see any problem then. Even your name works if you're dressed as a girl."

"That's the problem. I'm a boy. If I'm dressed up as a girl, people will call me names and laugh at me." He seemed to be getting a little worked up and his mom thought she could figure it out.

She gave Sam a big hug, then held him out a little. "Well, let's see. Right now you're wearing what we both agree is a very pretty dress, appropriate lingerie, and make-up. I don't hear any name calling or laughing, do you?"

"No," Sam said, and managed a smile.

Mom smiled too, and gave her new daughter another hug. "That's better. Pretty ladies like us look even better smiling. Now, do you think I can have my cute daughter visit sometimes?"

"You mean it's really okay for me to be dressed up like this? Like a girl"

Hugging her new daughter again, she said "It's perfectly alright. I do miss having a girl to dress up pretty sometimes, as much as I love you. Now I get to have both! I think right now we'll get you out of Janine's dress - you can wear the one you had on before."

Another quick hug and they changed Sam's dress. They added a necklace and bracelet set, and mom said, "It's a shame you don't have pierced ears. I have a cute set that would go nice with that dress."

"Does it hurt much?"

"Getting your ears pierced? A momentary sting I guess. Why, you want to get them pierced?"

Sam suddenly got defensive. "You're the one who brought it up."

"Oh honey, don't worry. I think it would be nice if you did. Hmm, think you feel brave enough to go to the mall? We can go to Carverson Mall, that's a little farther away."

Sam's eyes got real big. "Are you serious? Go out looking like this?"

"You look like a cute girl, and yes I mean go out like that. We could get your ears pierced, and do a little shopping."

"Shopping?"

"Sure, for clothes for Samantha. Your own undies and a few blouses and skirts, maybe a dress or two."

"Wow. Um, a nightgown?" he asked sheepishly.

His mom gave him a big hug. "Of course we'll get you a pretty nightgown or two! Let me do your nails, and then find you a purse." Soon Sam's nails were painted the same shade of pink as his lips. As his mom was putting on the polish, he found both his nervousness and his excitement growing.

Sam's mom handed him a purse and said, "Now look in the mirror and tell me you see anything other than a pretty young lady." Sam had to admit that all he could see was a girl. Off to the mall.

It was a little more than a half hour drive to get there, but it was doubtful they'd see anyone they knew. Even in the closer mall they might not see anyone, but Sam could feel a little safer at this one.

They entered through one of the larger stores. As they reached the front of the store where you entered the mall, they passed by the cosmetics counters. A perfume lady was there and they both accepted a spritz. Sam blushed as the lady went on about what a cute daughter his mom had.

First stop was the jewelry store, and Sam was soon sporting cute heart earrings. The quick sting was definitely worth it. Soon he could wear dangly earrings! Mom saw a heart bracelet, and she had to get it to match Sam's earrings.

As they left the store, Sam's mom asked "Where to next? Anything you especially want?" As her new daughter started to blush she quickly added "It's okay, honey. You don't have to be embarrassed." Leaning a little closer so only Sam could hear, she said "You can be as girly and feminine as you want. Remember, I'm loving having a daughter to dress up!"

Sam shyly said, "I want to find a pretty, silky nightgown."

"I know just the store. It'll be handy for a few more things too." She took Sam by the hand and they walked a bit through the mall, eyeing things as they went. Finally they reached the store, Lacey's Lingerie. No one else was in the store, which made Sam happy, but he was surprised when the saleslady saw his mom and said "Linda, how nice to see you. And who is this little angel you have with you?"

"Hi Sandra. This is my lovely daughter, Samantha." Sam blushed.

"Awww, what a cutie! So what brings you here today, Linda?" Sandra made no mention of the fact that she knew Linda had a son named Sam.

"Samantha wants a pretty, silky nightgown while we're out shopping, and after she finds one or two she likes, we'll probably get a few other things too."

"Sounds like a plan," Sandra said. She turned towards Sam. "Are you looking for long nightgowns, or short ones, hon?"

Sam managed a smile, and feeling a little braver said "Maybe one of each!"

Sandra led them to the nightwear. "Longer ones down here, and shorter ones and baby-dolls down there," she said pointing. Sam started looking through the long gowns, and soon found one that was his favorite. Peach colored, cutely accented with lace, with a matching robe and panties. Then he managed to find a baby-doll that was a perfect match.

Sandra and Linda were finding the right bras for Sam. Sandra had shown Linda a pair of breast forms that they would fit when Sam came over. That would help to really feel like a girl, especially glued on. Sam came over to show off her nightgowns, and found out what was going on. "Will they look real?" was the only question.

Before long Samantha stepped out of a dressing room, wearing a new bra that she now needed, and also wearing a very big smile! They then picked out some nice silk panties that matched Sam's new bras, and a few slips.

"Okay, where to next?" said mom.

"How about some cute dresses?" Samantha asked.

"Sounds good to me," mom said. "Right this way."

They found a shop catering to teen girls in just a minute. Samantha's eyes widened taking in all the great choices. She barely got inside the store before she grabbed a dress and said "I have to have this one , mom!" It was the twin of Janine's dress, the one that started everything, but in peach. "It would even look good with Janine's dress - shame we can't wear them together." Her smile faded a little.

To help bring her smile back, mom said, "If you did, Janine would be jealous because you'd look cuter!" They picked out one more dress, then a few skirts and blouses. They also found some shoes she liked in the back of the store. Three-inch wedge sandals and two-inch pumps. A nice day's haul!

On the ride home they talked about what they bought, what they saw and liked but didn't buy, things they saw that they'd like to get some day, and even what they saw but would never buy. Sam's mom was loving very minute of bonding with her new daughter. Sam seemed to have lost the nervousness of being dressed up, and by the time they got home she felt totally calm and normal.

They gathered up all Samantha's new clothes and headed into the house. Being careful not to drop anything, they weren't watching behind so they didn't see Janine approaching. Just as they got in the house she walked up and rang the bell. Putting all their purchases down, they went to the door, still acting as if it was normal for Sam to be Samantha.

"Hi Mrs. Parker. I saw you coming in and thought I'd see how my dress was coming along." Janine said.

Sam suddenly realized the reality of the situation, and was amazed Janine didn't seem to recognize him as she said hi to him. He managed to a soft "Hi" back.

Janine's eye was caught by the peach dress that matched hers. "Cool!" she said, "This matches mine. I bet it would look great with both dresses together."

Without thinking, mom said, "That's what Samantha said." She realized what she'd done as Janine's eyes grew.

"Sam?" Janine looked closer. "Oh my god! It is you!" Sam really started to cringe, afraid of nasty words about to follow. "I can't believe what a cute girl you make!" Sam's face changed to a look of disbelief, with a slight blush. "I'm not kidding, you make a really cute girl." Janine looked to Sam's mom for support.

"I may be the mom, but I definitely agree. You're adorable." Sam blushed even more.

"And I bet we'd both look great in our matching dresses. Hey! You could go to my cousin's wedding with me - that's what I bought the dress for. We'd look fantastic!"

"Oh that sounds fun," said mom.

"Hello? Aren't you two missing something?"

"It's okay if I bring a guest," Janine said.

Sam looked at Janine, then looked at his mom. Both just smiled. "Fine, I'll say it - I'm a boy!" He turned to Janine. "Look, I'm really glad that you didn't freak out and call me names and stuff, but be serious."

Janine took his hands in hers, smiling at the nail polish. Sam just shrugged. "I don't see anything to freak out about, except maybe how good you look, and surely nothing to call you names about. Well, do you mind if I call you Samantha some? It does seem more fitting," she said with a smile.

"No, not at all. You don't think it's weird that I'm dressed up like a girl?"

"I can hardly claim it's normal, I guess. But that doesn't have to mean that it's anything bad, Samantha. I don't think anything is wrong with how you look or how you're dressed. I like it! And I am serious about the wedding. And I am serious that we'd look great. See, you smiled, you agree we'd look great!" Sam just smiled and shook his head.

"Okay, maybe we'd look great in our matching dresses, but I still can't see it for real. Would your mom allow this, not to mention mine?"

"I think she would."

"And I will, of course," said Sam's mom.

"Well, what will people there say?"

"They'll probably say we're gorgeous! Who's going to tell them you're a boy? Go stand in front of a mirror. Tell me you're not cuter than at least half the girls in our class. I can see you agree."

"Still, I don't know."

Janine thought it a good idea to change the subject some. "I'm curious. How long have you been dressing up?"

"Today was the first time I ever wore a dress. Honest."

Mom spoke up. "I was hemming your dress and it helps if it's being worn. I drafted Sam to help, and I guess I kept pushing to add things to create the daughter I never had. I never meant to cause you any trouble, honey," she said, reaching out to Samantha.

"Wow, one day and you look like this? And I can guess by your reactions that you like how the silky clothes feel. Well, just imagine how it will feel, both of us in silky dresses, dancing together. Still don't want to go to the wedding?"

"I never said that I didn't want to go. It's just, I don't know, too quick?"

"It's a couple days away so you don't have to decide anything yet. Think about it?"

"You bet!"

"One thing though - if you chicken out on me, you still have to wear the matching dress with me!" They all laughed, calming things even more. "And I'm guessing if you went through all that you obviously did, you intend to stay being Samantha, at least for right now, right?"

"Yeah, why?"

"Is it okay if I stay a while? I'm sure we can find something to do."

"Sure!" Samantha said quickly. "What would you like to do?"

Mom spoke up first. "These new clothes need to get put away first. Why not put them in the spare room? We can slowly fix it up nice as Samantha's room."

"Okay." Between the three of them they carried everything to the spare room, now Samantha's room. Sam blushed when Janine saw his panties and bras and slips. As they put away the dresses, Janine said, "It is a perfect match. We'll look fantastic when we're both wearing our dresses!"

"I have an idea," said Sam's mom. "Come over tonight for a fitting of your hemmed dress, and Samantha will be wearing hers."

"Cool! And Samantha, I have a nice silky dress the same shade as your other dress, the blue one, so I'll wear that over. That way we can change after the fitting so we don't wear our nice dresses for long, but we'll match - this time the color, not the dress."

"Won't your mom want to come over to see you in the dress?" asked Samantha.

"I didn't think about it, but probably."

Sam's mom looked at her. "Would you be okay with that, honey?"

"I guess I'll have to be."

"I'll go have a talk with her now." The girls watched her leave the room. As soon as she was gone, Janine stepped closer to Samantha.

"I'm serious, I really like you like this. I bet this will sound really weird, but can I kiss you?"

"You really want to? Janine, you're like the cutest girl in school! You can kiss me anytime!" She apparently did want to, and didn't want to waste any time. Samantha finally managed a "Wow!"

"Wow is right!" said Janine. "I sure never kissed another girl like that before." Sam looked about to speak up so Janine quickly continued. "Yes, I know you're not really a girl. But look in the mirror and tell me you see anything but a really cute girl! And I guess I better add," Janine gave a big smile, "you also felt like all girl! And you better also already realize I am in no way insulting you, more like complimenting. Now quick before your mom comes back, let's have another kiss."

Their lips had barely met when they heard Sam's mom's heels in the hallway, and quickly separated.

"I explained everything," she said as she came through the door. "Janine's mother doesn't have a problem with anything." She smiled as she continued. "She even suggested that she and I get dressed up nice, too."

Janine said, "That'll be fun - everybody all dressed up." She looked to Sam, and she smiled, agreeing.

"Not sure what I'm going to wear, " Sam's mom said, heading towards her own room.

Janine held Samantha by the waist. "Well, after tonight maybe you'll be more used to people seeing you as a girl. Just relax and everything will be fine." She smiled and added, "And later tonight, while laying in bed in one of your new silky nightgowns, think about you and me slow dancing, both wearing silky dresses and lingerie!"

Sam grabbed a kiss before speaking. "You're mean!" she said. They both giggled.

  

  

  

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