Synopsis:

Robby's Mom always dressed so frumpy and he always wanted her to look pretty. Frustrated with his nagging she challenges him, "if you want me to dress up you dress up." What does Robby do?

Story:

Drawn Together Ch. 1

by

Paula Dillon

Sandy took her fourteen year old son shopping for shoes. It seemed that every time she turned around he needed shoes. She didn’t mind Robby was a good kid. So they both took off dressed in jeans and identical oversized Texas Rangers T-shirts. Robby didn’t realize how much alike they both looked. Together they headed to the local discount shoe store. She found four pair of shoes for him and decided that she could use a pair of flats herself.

The store had this thing about wearing socks or stockings when trying shoes on and she didn’t have any on, she hated those sometime dirty footies they provided, so bought a three pack of knee highs and went back to the ladies shoes section. While she was putting on the knee high’s, Robby had been looking at some of the ladies shoes. He brought her a darling strappy pair of stiletto sandals in a cream color, complete with four inch heels.

“Mom why don’t you try these on I think that they would look very good on you.”

“Son you know I don’t wear heels that often, especially heels that high.”

Robby was always trying to get her to dress more feminine and to some extent it irritated her. It wasn’t that she dressed ratty; she just liked to dress comfortably. He would often sit next to her and point out outfits he thought would look good on her in a J.C. Penny’s or Spiegel’s catalogue. He had a good fashion sense she thought, but since her husband divorced her she just hadn’t felt like dressing up for anyone.

“Mom that is it, you dress more like a boy, than most tomboys I know. I think you are pretty, and should dress that way. Not all the time mom but at least some of the time. You could be mistaken for a boy except for your curves. I can’t remember the last skirt or dress you have worn, and you hardly wear any makeup.”

Sandy was getting frustrated and wanted to object to her son’s taunts, when an idea popped into her head. The store was fairly empty at this time. As a matter of fact, they were the only customers there at the moment. “Ok, I will tell you what. I will buy two pair of shoes that you and I can agree on if you will try a similar pair on for me.”

“What do you mean?”

“I mean I won’t buy em unless you try on a pair just like the ones you want me to buy.”

Robby’s face went a shade of crimson. Sandy knew Robby would never agree to wear these shoes. Although he was small for his age at five feet, 105 lbs and his auburn hair went below his shoulders in a pony tail, he always tried to be so masculine. She knew he never messed with her clothes. When he did the laundry she would see him handle her under things as if he would catch some strange disease from even just touching them.

She nearly had a heart attack when he sat down next to her and he pulled off his shoes and his white crew socks and pulled on a pair of knee highs. She went off and found the exact pair of shoes he had wanted her to try on and returned with them, not believing he would try them on.

“These are just like the ones you want me to try on, in your size.”

They both wore sixes, she in women’s shoes, he in men’s. The pair of shoes she handed him were seven and a half’s. The dear child put them on. She had to help him a little he had obviously never threaded the tiny straps these shoes had before.

Sandy giggled as he tried to stand in them. She had to help him to keep him from breaking his neck. He walked to and fro in them bringing several giggles from her. He then walked over and found another pair that he wanted her to try on and handed them to her. Sandy went and found a similar pair in Robby’s size. She like his taste in styles, except these too had skyscraper heels.

Robby remained standing as Sandy tried on the first pair. She admired his determination and intended to keep her word. He offered her his hand to help her stand, not that she needed it she had gone through the heels phase and was accomplished enough at wearing them, but it was a nice gesture.

“This is how you walk in heels dahling. Take shorter steps and swing your hips a little as you walk,” she said in a seductive voice as she walked back and forth.

Robby tried to copy her, but it was rather comical. She had to catch him as he caught a heel in the carpet. They both had a quiet laugh. He was taking this in a good humor. They both sat down and changed shoes to the second pair. The second pair were patent leather black pump with small satin bows and four inch heels. They were the classic “fuck me” pumps with a pointed toe, but she wouldn’t mention this to Robby. Sandy checked his toes, snug but they fit alright.

Sandy stood and helped her son to stand and demonstrated the walk for him. “Walk mostly on the balls of your feet dear, not heel to toe like boys do.”

She walked gracefully away from him and turned and waited for him. Robby followed walking much better but a little inept still. About the time he reached his mom, a sales leady came from the back, not paying attention to where she was going, almost running into him. He caught himself though and didn’t fall.

“Excuse me ma’am, I am so sorry. Are you ok dear,” she asked looking Robby up and down?

Robby his face in full crimson blush stammered, “I am ok, no problem ma’am.” His throat was so tight in fear that he sounded feminine.

“Are these your first pair of heels dear, and oh I see your mom has a pair just like them. It is so nice to see mothers and daughters dressing alike.”

“Thank you so much dear,” Sandy said, “She just wanted to see just how hard they are to walk in. She was pestering me to get some.”

“Well they look so good on both of you. You both should get them. Well I need to get busy,” the lady said hugging both Sandy and Robby before leaving them.

When they were again alone Robby still a little red faced said, “Mom why did she think I was a girl?”

“I don’t know honey, but we are dressed alike, and your hair is long and in a pony tail. She just saw what she wanted to see.”

They both sat down and changed back into their own shoes. Robby didn’t bother to take off the knee highs; he just put his trainers on.

“I want to wait in the car for you while you pay for the shoes mom.”

“Ok dear, take my purse the keys are in there just let me get my wallet out.”

Robby walked away carrying Sandy’s purse over his right shoulder. The sales lady waved at him as he passed. Sandy didn’t know why but she bought both pair of pumps, along with the sandals for her and Robby’s shoes.

“I hope I didn’t make your daughter feel to self-conscious dear but those shoes did look good on her.”

“Yes they did, I am going to surprise her with them I think.” Yes ma’am it will definitely be a surprise Sandy thought.

Tomorrow is Friday, but school is out for a teachers work day and she will have a surprise for him. He wants her to dress up we will see how much he wants her to dress up.

Sandy dropped Robby off at home and went shopping for a few things. She would see how serious he was about her dressing up. She bought a package of three satiny panties his size, a couple of pair of pantyhose, a heavily padded brief, two 32A water bras and small silicone inserts, two pair of low rise fancy styled boot cut jeans a size or two too small in black and stone washed blue, several very girly glittery tops with a scoop necks trimmed in lace all around in lavender, royal blue, and black and a small purse that fit a girl his age. These combos would leave about an inch or two of bare skin between the top and the jeans. They would be fairly girlish outfits but would look good.

She got home; Robby was doing his home work and watching TV at the same time in the living room. She should complain but he was a straight A student at high school. She got the pumps she had bought and carried them with her other purchases down to the living room.

“Robby you have been bugging me for a long time wanting me to dress up nicer for a long while. You just don’t know what it takes for a woman to look nice. So I have a proposition for you. You want me to wear more dresses and skirts and to look nice, you’ll go shopping with me all weekend, and I emphasize ‘All weekend’. One catch though you will wear what I have in these bags.”

“Ok, I will.”

“You better look at what is in the bags before you commit Robby.”

Robby opened the bags and saw the pumps he had worn earlier and the rest of the clothes his mother had bought. His face went red and Sandy was afraid he was going to cry or get angry but the look of determination she was so proud of in him filled his face.

“I said I will mother, I will not go back on my word.”

“I know dear but I just wanted you to know what it’s like for me to dress up. I’m not trying to make fun of you. Well you better try them on and get use to the heels cause we are going power shopping tomorrow.”

Robby started to get up and take the bags up to his room but Sandy stopped him.

“It’s just us girls here this weekend. Besides I know you’ll need my help with some of it so here is as good a place as any. He opened the bags and laid out the things in an organized manner. He was very methodical at his approach. He then stood and stripped down to his shorts. Sandy turned to allow him time to take off his shorts and put on his panties, she wanted to give him a modicum of modesty. She turned and saw a very unladylike bulge in the front of his blue satin bikini panties.

“You’ll need to tuck your stuff between your legs dear if you’re going to be able to wear this stuff Robby.”

It took Robby several minutes to get himself adjusted and his panties pulled tight to keep himself in place. It was amazing he looked like any prepubescent girl of twelve or thirteen, standing there in just her panties.

“Next put the padded brief on dear; to give you some hips.”

He pulled the padded briefs on which further disguised his figure. Sandy helped him with the bra and inserts. The bra fit very snuggly around his chest and looked natural. Mom then gave him instructions on pulling on the pantyhose. Now came the hard part the ladies jeans. He had selected the black jeans. Both pair had intricate designs in a contrasting thread embroidered throughout.

“Mom these jeans are way too small I will never get them on.”

“Sure you will Honey, girls do it all the time. That is how they wear their jeans Robby.”

He couldn’t argue with her. He knew she was right; still it was a five minute struggle to get them on. The jeans fit like a glove, no that isn’t right and skin tight wasn’t even a good description. He felt his butt cheeks part as he at last pulled them that high. He started to try to button the jeans but his Mom stopped him and tucked his underwear beneath the waist band of his jeans. The jeans buttoned and zipped, he looked at the tops. He took the lavender top to go with the black jeans. It fit nicely, but he saw when he raised his arms that he exposed much of his soft tummy for all to see. Lastly came the ‘FM’ pumps.

Sandy couldn’t believe the transformation. Robby looked like a very pretty teenage girl in her Mom’s shoes. He had gorgeous legs for a girl his height. Even his hairless tummy looked girlish. She helped him stand and walked him slowly over to the hall closet. She opened the door to expose a full length mirror and Robby looked at himself.

Robby’s jaw dropped as he looked in the mirror. Sandy removed the scrunchie that held his pony tail and combed out his soft, silky, shiny hair with her fingers over his shoulders. His hair fell to the tops of his faux breasts and enhanced his girlish appearance.

“Now we need to get you comfortable in those heels dear.”

“You get your heels on too, if we are going to do this.”

“Ok, I guess that is fair.”

Sandy went to her room and put on the strappy sandals Robby had picked out for her.”

Together they walked back and forth in their shoes till Robby started to look like he was doing fine in them. Sandy then had him practice sitting, standing in the heels, walk some more, turn, walk, sit knees together crossed at the knee or ankle (never spread eagle). Robby seemed to adapt well. Sandy showed him feminine gestures, brushing his hair back with his hands, folding his hands demurely in his lap and such. It took about two hours before he fit the image he projected.

Sandy went to her room and got a lipstick, mascara, eyebrow pencil, compact, clear and pink nail polishes, blush, tampons, a wallet, which she put some cash in, tissues, tweezers, nail file, gum, earrings, necklace, bracelet, watch, rings and a perfume. She grabbed the purse she had bought him and they went into the kitchen. She went to work on his face. Ten minutes later and he had very light makeup on (powder, blush, mascara, eyebrow pencil, and lipstick). She then worked on filing his nails, they were a little ratty for a girl but not overly so, but longer than most boys nails for sure. She then put on a coat of clear polish, two coats of pink in a shade to match his lips and a clear topcoat. This was fun for her she missed not having a daughter to do this with. She put her rings on him they were a little loose on his fingers, the pearl tennis bracelet, watch, a string of faux pearls around his throat and pearl drop earrings on his ears.

Sandy couldn’t believe her eyes. Her jaw hung open. Robby was not just pretty he was gorgeous.

“What is wrong Momma?”

His voice sounded even more feminine now.

“Nothing dear, you’re just so incredibly lovely.”

“Stop teasing me Mom. I look like a guy trying to look like a girl don’t I?”

“No you don’t dear, come look.” She took his hand and led him to a mirror.

He looked at himself. He even pinched himself, but the vision didn’t go away. His eyes started to water and his lip began to tremble.

“Don’t cry, Robby I can take this off and we can forget about this silly dare dear. I am so sorry. I didn’t want it to go this far, I never believed that you would agree to it.”

“That’s ok Mom. I just wanted you to look as good as other mom’s I know. You are so pretty; I just wanted the other kids to be jealous of me. It’s just I never thought I could be so pretty myself.”

“Well you just clean your face off, and take those clothes off. I will take them back. You are too important to me to hurt you like this.”

“No Mom, we made a deal, I will go shopping with you dressed like this, and you will dress up for me a couple of times a week.”

“You don’t have to do this dear, I will dress up more often.”

“No Mom, I want to show you how serious I am about all this. You are too pretty to hide in your baggy shirts and pants all the time. I will dress up for you occasionally, I saw how much fun you had doing it and you will dress up for me occasionally. I think you wished I was your daughter instead of your son. I can be that daughter for you occasionally. Ok.”

Robby brought tears to her eyes. They hugged really tight and had a good cry there in the hall.

“I love you Robby no matter what. The clothes don’t make any difference in that dear. I am glad to have you as my son.”

“I thank God everyday that you’re my mom. I see so many of the kids around me whose parents don’t care for them. I know you love me. I never have to wonder with you Mom.”

“Well then can I roll your hair before you go to sleep dear, and comb it out in the morning?

“Yes Mom, almost anything for you.”

“Then let me get you ready for your bath. Wash and condition your hair then come to my bedroom.” Sandy said reaching under his top to unhook his bra.

They went to his room and she helped peel him out of his jeans. “Shave your legs and arm pits too Robby.”

“I don’t have any razors yet I don’t shave at all.”

Sandy didn’t realize that, she went to her bath and got him a new razor.

“Be careful dear try not to nick yourself, slow smooth strokes she demonstrated in the air.”

He went to his bath and she to her bedroom. She got her rollers out and thought about what Robby had said to her. She had forgotten her years of growing up. He was right, she promised herself to be the kind of mother he deserved. Robby had made her proud. She got her rollers out. She would probably need them all for his long hair.

Fifteen minutes later he was skipping into her room in panties and bra. Sandy just had to smile. She got out a setting gel and worked it into his hair as she rolled it on her rollers. She explained as best she could what she was doing and he paid attention as she worked. It didn’t take too long till she was putting a hair net over his rollers.

“Now when you get up in the morning I will comb it out for you and we will see what we have. How are your feet dear?”

“They’re kinda tender but I can live with em.”

“Off to bed girl, we have a big day tomorrow.”

Robby gave her a big hug and a kiss on her cheek,

Sandy awoke to the smell of coffee brewing and breakfast cooking. It was only seven thirty. Robby usually didn’t get up this early on a weekend. She got her robe on and headed downstairs. Sandy peeked around the corner and Robby was busy at work, he wore her apron while he cooked and was fully dressed, jewelry and all, in his blue stone washed jeans and black top wearing his heels. It wasn’t unusual for him to cook she had taught him that much, but to be dressed as a girl with his hair in curlers made Sandy giggle.

Rob looked up and saw Sandy and smiled. “Oh hi Mom, good morning,” he said and skipped over to her and gave her a hug, before returning to finish their breakfast.

Sandy set the table, and poured a coffee for herself, as Robby brought the plates with omelets for them.

“You seem quite chipper this morning.”

“I am excited about you getting you some nice clothes, Mom.”

“I can tell, but the shops don’t open till ten dear and it isn’t even eight yet.”

“I also wanted to see if I could get it all on by myself.”

He did indeed have it all on. He had even done his own makeup and not a half bad job. “You haven’t done this type thing before have you?”

“No Mom, I haven’t.”

“Well you sure picked it up all right. I want to redo your mascara and blush but not a bad first job for anybody.”

As they ate Sandy told Robby what they would do and where they would go. There was a new Mall on the other side of town where neither of them would be recognized, yet had some of her favorite stores. Robby wouldn’t have to try on any clothes because it would take forever to get in and out of those pants.

“For the most part Robby you have a pretty good fashion sense. I might adjust it to my age styling, but I will promise to give your picks serious consideration. I might reject some, but I will explain why instead of just giving you an outright rejection. There might be some room for negotiation.”

“That is acceptable. I just want you to look as pretty as I know you are.”

“Ok Hun, let me get my shower and get dressed while you clean up here. Then I will fix your hair and makeup. You don’t mind cleaning up here do you?”

“No Mom, I am glad to help.”

Twenty five minutes later Sandy was dressed and doing her makeup. It had been a long time since she had used a lot of makeup and she wanted to look nice for her son. She made a note that she would need more makeup since she would have to be doing this more. She just hadn’t felt like doing it after Dave had moved out with his secretary. She felt old and frumpy, even though she was only thirty six. She took care of herself but she just didn’t dress up or makeup anymore. She just didn’t feel it was important anymore. At least he had the decency to leave before she inherited her Granddad’s estate and didn’t have to share any of that money with him, she giggled. Good thing he isn’t here to see his son right now that would really chap his ass.

“Ok Robby, come on in.”

“Mother, I thought you were going to dress nice.” Robby said a little exasperated, after seeing his Mom.

“I have dressed so it’s easy to change clothes dear. If I had dressed like you are it would take twenty minutes just getting in and out of those pants. This way I can try on more of the clothes we pick out. I did wear the sandals you picked out. I chose those pants for you hoping you would reject the idea, but you’re made of sterner stuff than that. Now sit!” she said in mock sternness.

“Oh!” Robby said.

“Take your earrings off Robby, You have lots of gorgeous hair, I am going to give you a big Do.”

Sandy took out the rollers and started back combing and teasing his hair. She could tell when she wound up pulling his hair to much as he would wince and give a little whimper, but he bore it stoically. She must have used half a can of hair spray as she added her final touches. She then turned him to the side and cleaned the eye makeup and blusher off his face. She curled his lashes and added two coats of mascara.

“Blusher should be added with a brush from the ear forward and should add just the hint of color, not shouting it, other than that I would give you a B+ for your earlier efforts.”

Robby beamed a smile at his mom.

She finished her job, replaced his earrings and asked him to close his eyes and to turn to the mirror. She told him to take a deep breath count to three and then open them and look at himself.

“Whooooa Mom! This is the kinda look that would be great on you.” Robby said turning his head left and right.

Sandy looked in the mirror as Robby turned his head back and forth. “You know something, for special occasions you are right, but my hair is way too short for it now, but there are other styles I could wear till mine can grow out some more. Go get your purse dear and let’s get ready to go we have lots of shopping to do.”

Robby looked so sexy as he walked away, he should have been born a girl Sandy thought. They met at the stairs and descended carefully down to the first floor. Robby was so giddy and wasn’t paying attention to where he was going as he opened the front door and stepped right into a girl who was fixing to knock on the door. Sandy had reached out and caught Robby by the collar of his top and Robby’s and the girl’s arms went around each other in a hug, to keep each other from falling over.

There were apologies muttered and Robby said, “Tiffany?” and the girl just stared.

“Come on inside Dear, It is Tiffany I presume?”

“Yes it is. Mrs. Davis?”

Robby a little slow on his feet realized that he didn’t look like he was suppose to look, and said, “Oh shit and started to rush to his room.”

“Running won’t do any good dear. The cat is or soon will be out of the bag.”

Tiffany just stood there starring and finally headed where Sandy directed. Robby followed everyone into the living room.

“Tiffany it’s nice to meet you and you are probably wondering about Robby. I take it you know each other?” Sandy said as she directed everyone to sit. “Well let me explain please. Yes this is the Robby you know.” Sandy went on and told her everything. “You see Robby just wanted me to dress nicer and I foolishly dared him to dress that way if he wanted me to dress up so much. He took up my dare and we were headed to the mall when he ran into you. He doesn’t generally do this sort of thing.”

Robby had been on the verge of bawling for the fifteen minutes that his Mom had been talking. He had sat there ladylike hands in his lap. Tiffany just looked at him with a smile on her face. After Sandy had finished Tiffany got up and sat on Robby’s lap and gave him a big hug and comforted him.

“Robby don’t cry, I think it’s so wonderful. I respect what you are willing to do for your Mom. Don’t worry dear; I am not going to hurt you by saying anything. You look so incredible I am in awe.”

Sandy checked out Tiffany as she comforted Robby. She was about two inches taller than Robby and had a very mature figure for a thirteen or fourteen year old girl. She was a real doll. She appeared to be enjoying comforting Robby, a bit too much possibly.

Tiffany released her hug on Robby and stood. Robby had raccoon eyes. She looked Robby up and down, “I love your outfit and your FM heels.”

“FM heels?”

Tiffany blushed and held her hands to her cheeks and looked at Sandy.

“You opened that can of worms dear, you explain it.”

She whispered in his ear. Robby turned red and he fanned himself.

Sandy looked at her son and said, “Let’s get you cleaned up dear,” and led her son to her room.

Tiffany followed as they left. Sandy took a wet wipe and cleaned away the makeup and set about reapplying it. It took just a few minutes and Robby looked as good as before.

“Mrs. Davis, may I go with ya’ll. I could stand to pick up some things, myself.”

Sandy looked to her son, who nodded. “Call me Sandy, Tiffany. If it’s ok with your Mom, it’s ok with me.”

“It’s just my Dad. Mom passed away years ago. May I use your phone?”

“Sure dear. It’s over there by my bed.” Sandy said pointing.

“Dad this is Tiff, Robby’s cousin and Mrs. Davis are going to the Mall can I go with them? Ok Dad here is Mrs. Davis”

“Yes this is Robby’s Mom. His cousin Marci and I are going to the mall clothing shopping. No he is out of town right now; they just sorta traded places for the weekend.” Sandy thought for a second and put her hand over the mouthpiece of the phone. “He wants to know if you want to spend the weekend here. It’s ok with me, as long as there is no monkey business between you two.”

The kids looked at each other and shook their heads.

“Ok we will be there in ten minutes John. No problem,” Sandy said. “Tiff he wants you to pick up some of your things and get some money from him. So let’s get rolling. Make sure you get something decent to sleep in, if you know what I mean.”

“He will probably sneak out of the house and go fishing if I know him, and I do. I hope it’s ok with you Robby?”

“I think I am Marci now, at least for this weekend. It’s ok with me I guess.”

Sandy looked down at Tiffany’s feet, “What size shoe do you wear?”

“A six ma’am.”

“I have a pair of FM heels just like Marci is wearing if you would like?”

“I would love it Sandy, if we can bring them along and I could change after we leave my home. I am afraid dad wouldn’t understand.”

“No problem.” Sandy said as she handed the shoes to Tiffany. “Let’s get a move on the Mall is calling.”

It was a short drive to Tiffany’s home. The three of them went into her house. Sandy felt herself flush when she met Tiffany’s Dad, John. He was a real hunk, Tiffany would probably say. Sandy thought he was such a handsome fellow.

“Hello I am John Thomas, Tiffany’s Dad.”

“I am Sandy Davis and this is Marci Duncan my niece.”

“Well it’s nice to meet two charming ladies.”

“Come on Marci help me pack.”

Tiffany pulled Robby with her leaving Sandy with her Dad. In her room she had Robby pick out some outfits while she got her lingerie and sleep shirts. She also smuggled a baby doll into her suitcase not sure if she would wear it. She liked Robby. She liked him much more than he knew, but she liked Marci also. She had stumbled on the perfect guy for her. She didn’t understand her feelings, but she was sure she didn’t want this person to get away from her, and here she was getting to spend the whole weekend close to him. She went to her closet and selected a white chiffon blouse and a black Mini-skirt that came to her mid thigh. She got a camisole and pantyhose out of her drawer and started to strip. She saw Robby looking at her in the mirror. He wasn’t looking at her with lust in his eyes but confusion. He really was a nice guy. His was tongue tied as she pulled on her hose and camisole. She finished dressing.

“Go to the bathroom for a minute or two. It is just the next door down. I will be packed by the time you finish.”

Robby did as he was told. He needed to use the facilities anyway. It took him considerably longer than two minutes to relieve himself. He liked Tiff. He had always been afraid to speak to her and here she shows up at his home as he is dressed like a teenage girl. He checked his face like his Mom told him to, whenever he went to the restroom dressed as a girl and touched up his makeup. When he came out he heard his Mom say.

“And if you want John, Tiffany can spend Sunday with us too, and I will see to it she gets to school.”

“I really appreciate that Sandy; it’s so rare I get to spend time alone. I love my daughter but sometimes I need to get away.”

“Ok girls lets get away. I would like to hit the mall by noon.”

John handed his daughter a wad of cash which she put in her purse, and then they headed to Sandy’s car. Tiffany’s suitcase went in the trunk and they all piled in the front seat.

“No, he isn’t seeing another woman Sandy. He will be on Toledo Bend fishing before the sun goes down. He is a big bass fisherman.”

“I wasn’t going to ask that Tiffany.”

“No, but you were wondering it.”

Both the girls were giggling and Robby was wondering if they were aliens. Tiffany slipped off her flats and slipped on Sandy’s heels.

They reached the Mall about noon so they headed to a restaurant at the mall. The waiter held the chairs for all three of them. Robby felt at ease in his role and it showed. They talked about what they would do this weekend. It sounded like it was two days of shopping, and Sunday for relaxing. Tiffany counted the money her Dad had given her twelve twenty dollar bills.

“Dad must really have needed to get away, he gave me over two hundred to shop with. Plus my own money I can see a lot of new clothes coming my way. He is really glad when I find other girls to hang with, he is afraid to leave me alone and I am not into that fishing bit. I am sorry Sandy if I spoiled any plans you had with your daughter, I mean niece.”

“That is ok Tiffany; Marci doesn’t seem to mind do you?”

“No I don’t, I like you Tiffany. I just never had much of a chance to speak with you. It was a big surprise when I ran into you. Why were you coming over?”

“Cause to be truthful, I really like Robby and I felt he liked me too, but I figured you were too afraid to talk to me. I see him as a neat guy, who isn’t afraid to take a stand for things he believes in, but a little afraid or shy of girls. I think Marci can really help him there.”

“While we are being truthful I think Dad likes you too Sandy.”

“Why would you say that?”

“Well Dad aint nevah let me out of his sight for three days before girl, and I saw the way he was lookin at ya. He is probably afraid there is a Mr. Davis. Is there?”

“Was, he left both of us about eight years ago. He divorced me and married his secretary, and yes John ferreted that fact out. Maybe we can trade kids some weekend.”

“Nope, where Marci goes, I go.”

“Don’t I get a say in this?”

“You can say yes,” they both chimed in giggling.

“But really, Robby could use some male influence in his life.”

“Ok girls let’s head to the ladies room, Marci, you need to be sure you sit to take care of your business and roll off some TP no matter what you do dear.”

The three of them headed to the ladies room. They had to wait in queue as the stalls were all occupied, but they got their opportunity to go. The girls let Marci go first. He didn’t need to go as bad but still took this opportunity to empty his bladder. Either the jeans were stretching or he was shrinking under the pressure, or he was just getting better at pulling up the pants but he was getting faster. Still his Mom and Tiffany had beat him out. Robby powdered his nose, forehead and cheek, and repaired his lipstick.

Leaving the restaurant they headed to one of the major stores in the Mall. The first department they came to off the main concourse was the cosmetics. Sandy and Tiffany seemed really excited to be be there and together they moved between counter to counter looking at the samples and charts. Robby saw a chair near one of the displays and sat for a minute. The heels while nice in appearance but were hell on his feet, so he welcomed a chance to sit.

“Hello Sugar, I see you are next.” A lady said to him. “My, what lovely hair and skin you have, it’s nice being young. Well lets get started Sugar. My name is Nancy; I am a makeup and skin care coordinator.”

“I am Marci ma’am.” Robby said rather sheepishly.

“Don’t be shy sugar. It is good seeing girls your age checking out skin care and makeup. Now let me start with our skin care.”

Nancy was really attractive and about twenty-five, Robby thought. She took some kinda makeup wipe and started cleaning off his makeup and went from one potion to another cleansing, toning, and moisturizing his skin. He saw his Mom and Tiffany looking for him, when they saw him he mouthed the word help, but they just smiled at him and watched. Nancy explained what the products were for and how to use them. The skin care felt really good he could feel his skin tingle and get tight but not uncomfortably so. Then she started with the makeup. Sandy paid close attention as Nancy made Robby up.

“You have such lovely skin Sugar, and you need to be careful not to clog your pores with too much makeup. Our base is lighter than most and is real good for young girls. We don’t want you to have an acne outbreak because of your makeup. Your powder was a little dark for your skin dear, this will compliment your natural skin tone and hair color better Sugar. I know your Mom over there, probably wouldn’t let you use this much makeup but we are going to give you the works, just for today.” Nancy said as she went to work selecting colors and blending them on Robby’s face. “I just love your eyes girl they are so expressive, now close them as I use this eye liner on your lids.”

Robby felt a wet brush of sorts trace his lids just behind the lashes both lower and upper.

“Okay open your eyes Sugar. Now I am going to curl you lashes and add some mascara. Now your Mom may not let you use much eye shadow but we will use it today just so you can see how to use it. Use a lighter color here and here then overlay and blend in a darker color like this. It deepens your eyes and makes them more alluring, Sugar. My, my you are such a cutie. Now we take this lip pencil, this color takes your normal auburn hair color and compliments it. Now I trace the outside of your lip and this gives you the illusion of fuller lips. Now your lipstick will be just a shade or two lighter. When possible Sugar, use a brush for your lipstick. I know it’s not always practical but you get a better finish. Just fill in the middle don’t cover the lip pencil dear. Like your Mom use to say stay inside the lines dear. Now you can add a clear gloss for really luscious lips or you can go with just what you have on, either way you’re a real knockout Sugar. Oh I forgot your blush. Take a brush like this get just a little color, we aren’t out to paint your cheeks, we just want to add a hint of color. Start at the ear and brush to and swish it toward the corner of the eye. Voila let me get a picture girl, my bosses like to see the results I get.” She got a Polaroid out and took Robby’s picture. “Now look in this mirror and tell me what you think.”

Robby turned to the mirror indicated and a wow formed on his lips but no sound came out. Robby was mesmerized by what he saw.

“Is it that good Sugar, or are you just lost for words?”

“Oh yes, excuse me Nancy. I love what you did. I can honestly say I ain’t nevah looked this good. What do you think Mom? Tiff?”

“Marci you are lovely, that is a little more makeup than I am comfortable with at your age, but you would look lovely for a special occasion or such. Tiffany what do you think?”

“I am jealous that my sister looks better than I do.”

They each took turns getting made over, Nancy was a master at makeup and sales. Sandy bought a complete set of makeup and just the skin care, lipsticks, compacts, and blushers for Robby and Tiffany.

“You didn’t have to buy all that for me,” Tiffany said.

“Well I couldn’t buy it for one of my daughters and not the other could I?”

Tiffany liked the sound of a woman calling her, her daughter. She was taking a real shinning to Sandy.

“Thank you Mom,” Tiffany said as she hugged Sandy. “I love you Sis,” as she hugged Robby.

Tiffany’s words affected Sandy and Robby; it brought all three of them closer together.

Just past the makeup in this store was the lingerie. Robby would never have been caught dead in this section before, but with encouragement from Sandy and Tiffany he became less self-conscious and actually started liking being here. Two-thirds of the shopping went to Mom, but Tiffany got Robby’s assistance in making a selection or two. Robby got over his embarrassment when Tiffany brought a bra and panty set to him for his opinion. Sandy made a few purchases even for Robby, a couple of sleep shirts, a couple more bras and more panties, on the sly.

Next they hit the Misses Coordinates. Tiff and Robby dug in selecting outfits for Sandy to try on. She let them have their head. Each of them would pull a blouse or skirt or such and hold it up to the other as they dug through rack after rack. Sandy was amazed at Robby’s fashion sense he must have gone through catalogue after catalogue checking out clothes he thought would look good on his Mom to be able to make such brilliant selections. Tiffany was assisting but she even bowed to Robby’s advice. Together they handed Sandy a huge pile of clothes to try on. Their choices were younger looking, smart, sexy and a little too short for her tastes but she tried them on. Not a single pair of slacks or a plain T shirt or blouse. Everything was soft, silky, full of color and simply gorgeous. She didn’t keep anything above mid thigh, but there were plenty of skirts between mid thigh and the knee. She even felt younger as she tried the clothes on.

The girls were enjoying the fashion show that Sandy was putting on. Tiffany brought Robby back into the fitting room and made Sandy try on some of the shorter skirts she had rejected. Feeling a little self conscious she put them on and was persuaded to keep one or two of the mini-skirts, but most of the clothes she tried on looked good on her. Sandy did have some awesome legs as Robby put it and she still had a young figure. They made her keep on one of the shorter outfits and a silky blouse, and packed her frumpy comfortable clothes in a bag.

Hitting the racks again she was finally rewarded with some slacks and shorts, they were nothing like her favorite clothes though. Some were even like the clothes she had gotten Robby in. She guessed what was good for the goose was good for the gander. She found herself getting caught up in their enthusiasm. It was becoming difficult to realize that one of the girls was a friend of her son, the other was her son and not her own girls.

They then hit the misses dresses. Robby was really showing bright here. The dresses he picked were really quite nice, and flattered her appearance. Her son was important enough for her to give all this a try. Tiffany not having a mom, hadn’t had an opportunity like this either and was really into it to. She might be able to help Tiffany out with mother like duties. There were a few questions she would like to ask her.

After four hours of Sandy, Sandy, Sandy, shopping. Sandy maneuvered the girls to the 5’s, 7’s, and 9’s sections for Tiffany. Robby showed a good eye here too as he helped select stuff for Tiffany. Tiffany gave as good as she got though and dared Robby to try some of her selections out. Robby looked trapped and finally relented. His first change into a short skirt and blouse took a while, but his subsequent changes came rapid fire. One blouse Tiff chose was a white chiffon blouse with puffy long sleeves for him was buttoned up the back. Tiffany helped him dress in that one. Sandy told Robby to set that blouse aside and a black mini-skirt he had tried earlier and went off to get a camisole that would flatter him and the blouse. When Sandy got back the kids were fawning over some other clothes. She handed the camisole to Tiffany and whispered in her ear.

Robby came out in that blouse, camisole and skirt, next.

“Leave that combination on Robby I like that on you.” Sandy said.

The sales lady pulled all the tags. Robby came out with four blouses, three skirts, two shorts, a pair of slacks with a flat front, that zipped up the back. Tiffany really came out big, Sandy bought her some really nice clothes too. About twice what Robby got but these were her everyday clothes. Tiffany gave her a big hug when Sandy paid. They made a quick trip out to the Buick and hit the mall again.

Robby was slowing down and walking more gingerly than either Sandy or Tiffany, but he didn’t complain. Some of that was the skirt he was wearing, but the heels had to be giving him a pain. They talked to Robby about wearing a skirt and how to move about in one. He paid close attention to what they were saying. Sandy led them to a different restaurant and the girls were glad to have a seat.

“These heels are hell on my feet Robby, I can just imagine how your feet feel,” Tiffany complained.

“Yes my feet hurt also, but I was determined to carry through on my part. Mom I know this may be strange but I like wearing some of these clothes. I don’t understand it.”

“Women’s clothes for the most part are made to feel good; they seduce the wearer and the looker. Unfortunately the heels just make you look good, and they don’t really feel all that good.”

“But does it make me gay because I like wearing these clothes.”

“Not at all Robby, you did it originally to gain my compliance in dressing better. Do you like girls, would you rather make out with a girl or a boy?”

“I don’t think I could make out with a boy Mom, I am really turned on by a nicely dressed girl. I know I wouldn’t want to dress this way all the time, but it has been nice today, and I think I could hang with it for this weekend.”

“Thank you, I like you both ways Robby, it would be nice if I could have a sister sometimes, and a boyfriend most of the time. Would you be my boyfriend Robby, please?”

Robby blushed and leaned over as if to whisper into her ear and kissed it. Tiffany hugged Robby and giggled.

“Well you are right about one thing Robby, John expects Marci to spend the weekend with Tiffany, not Robby so you will have to tough it out.”

“I figured that out Mom, its ok Tiffany has been pretty cool about it, and I like her. I am pretty cool about the clothes too; I know I need them if I am going to spend the next two days this way. I think I might like doing this at different times too.”

“Robby I know I shouldn’t have done this to you, but I want you to know how proud I am of you. The way you have withstood this and stuck to your guns is inspiring. I know it’s unusual for guys your age to be into fashion, but you should really consider a career in fashion. I think you would excel in it. Think about taking tailoring and fashion next year at high school but remember it won’t make you popular with the guys.”

“I know Mom, I already have a hard time because I am so small and I like my hair long, but mostly I try to stay invisible. When I do that I don’t have as much trouble. I do draw pictures Mom. I have a lot at home you haven’t seen. I will show you when we get home. Tiffany I like you but I don’t think I would ever have gotten the nerve to speak to you. I always thought about how pretty you are. Why me?”

“You were always nice to me Robby. When you meet me you look me in the eye, not starring at my chest or legs. I never felt you were trying to get in my panties,” Tiffany giggled and turned red before continuing to speak, “You are a nice guy and believe me there are a few girls out there that want you, so I just made my move. I kinda liked that you would go to this sort of extreme for your Mom, she is very pretty.”

“My clothes aren’t that bad, Tiffany.”

“It is not bad for a grand mother or for some of the time, but you live all the time dressed in cutesy stuff Mom. You never dressed nice, at least not since Dad left. I know he took out a lot of your spirit Mom; he ripped out my heart too. He hasn’t seen you or me in six years. You are beautiful Mom get out there and shine. I would wear sack cloth shirts and pants if it got you to dress up.”

“He is right Sandy, your as beautiful as my mom was, you need to look as young and sexy as you can be.”

They finished eating and made a trip to the ladies room, and then hit the mall again they hit shoe stores next. Sandy found some moderate heels between two and three quarter inch heels to three inch heels she bought quite a few of these matching them to what she remembered of the clothes she bought. She found one style that matched for all three of them a blue satin sling back with a three inch heel. She also got Robby a pair of Mary Jane flats for him.

Robby began to notice that since dinner Tiffany was always so close to him, touching him, looking at him, and talking to him. Their little show and tell session had amazed Robby and he was glad for Tiffany’s company.

“Honey while we are at the mall and dressed up can I get a portrait of you like this? I just can’t believe how beautiful you are,” Sandy asked.

“I guess Mom as long as I can get one of you like you are.”

“Tiffany, we can get a portrait of you for your Dad too.”

“Yes Ma’am, I think Dad would really love that.”

The photographer did a lot of walk in business and we didn’t have long to wait. They did three individual shots, Robby and Sandy, Tiffany and Sandy, Robby and Tiffany and then a group shot. They were told that the proofs would be ready for selection on Monday.

The last stop at the mall was at a piercing boutique. Tiffany egged Robby to get his ears pierced. He relented to a single piercing but wound up with two gold ball studs in each ear. Sandy had never had her ears pierced so she got a single piercing. They were told to leave those studs in for at least two weeks before changing them and had to have a stud in full time for a month before they could go without earrings. Tiffany bought a bunch of new earrings.

Eight hours at the mall began to show on Robby so they decided to head on home. The trunk and back seat were full of bags. Everything was dumped in the living room for sorting except for Tiffany’s suitcase which went into the guest room. Robby plopped down on the couch exhausted but Tiffany made him stand and sit like a lady.

He finally got a chance to kick off his heels though Tiff sat on one side of him and Sandy the other and they sorted through their bags. They had another fashion show as they tried on all their purchases. They changed their clothes right there in the living room. Robby was treated no differently than any girl and changed his clothes right there where they were.

He didn’t blush as Sandy and Tiffany undressed and tried on their things. Tiffany was big chested for a fourteen year old a 34C all most as big as Sandy who was a 36D. Robby looked scrawny next to them. He tried on the few clothes he had gotten and modeled them for the girls. He finished with the satin sleep shirt. Tiffany got one of her night gowns on as Sandy did the same.

Tiffany had Robby sit on the floor in front of her and proceeded to brush his hair out. His Mom got the nail polish they had used on his fingers and did his toe nails. Tiffany started to work his hair into a French braid. Robby then painted his mom’s and Tiffany’s toes. They cleaned their makeup off and taught Robby how to use his skin care products. Robby had to promise to use them three times a day regardless of whether he looked like a boy or a girl.

Over three bowls of mint chocolate chip ice cream they watched the late Friday movie, Never Been Kissed, cuddled together on the couch. It was like a real sleep over.

“Promise me that you won’t engage in any Monkey business and I will leave you two alone.” Sandy said.

“We won’t, Sandy.”

“I promise Mom.”

Tiffany cuddled close to Robby as the Late, Late movie started. Robby never had, had his arm around a girl before but it felt good. They both got a little bored with the movie and started a petting session. Tiffany slid on Robby’s lap and they started a tongue hockey session. She ground her breasts into his chest, but he kept his hands in safe areas like her waist and back. She leaned back and looked into Robby’s eyes and moved one of his hands to her hip.

“We aren’t going to screw but we can feel each other a little Robby. I love the feel of your satin sleep shirt. Just hold me now.”

Robby caressed her all over. Her nightgown was layers and layers of soft silky nylon. It was very uncomfortable in his panties, but he made no effort. She was purring in his ear as he drifted off to sleep.

Sandy checked on the two kids about two hours later and they were both asleep in each others arms Tiffany on Robby’s lap and her head on his chest. She covered them with an afghan and cut the TV and lights off. She left the bathroom door cracked and its light on before she retired.

(to be continued)

Notes:

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