Getting a Girl Ready

"Ok sweetheart it is time to get up. I let you sleep as long as I could but we have to get a move on Megan will be here any minute," said Amanda as she gently woke Bailey. Then as if on cue the doorbell rang announcing Megan's return. Amanda quickly left the room to go help her sister inside. Bailey slowly sat up rubbing the sleep out of his eyes as the reality of his situation settled back in on him.

He was trapped by that bitch Megan. She had forced this embarrassing situation on him. He couldn't believe what he was going to have to do. He was going to be a laughing stock. Sure he was a little on the small side but he was still a man. But he didn't have a choice; he couldn't risk Megan sharing what she knew. So he would have to play along for now. Hopefully, this would all be over soon and he could figure his way out of Megan's blackmailing.

The Best sisters now sat in the kitchen after Amanda had helped her in with her bags. "Okay, sis I know this is gonna be weird today seeing your boyfriend like this but just remember this was his idea. He just wants to show you his support and be there for you just like you were for him," said Megan. "I know it is so sweet of him. I just cannot believe he is willing to go through all this for me," said Amanda as they heard Bailey making his way to the bathroom in the hall.

"Ok while he's in there I need to show you something. I did some research last night to try and find ways to help Bailey be convincing. I know the last thing either of you wants is for him to be found out. I think I found something that you should do to help him out. It's called tucking. Here take a look at this video. I know it seems strange but we can't afford any slip-ups today right?" said Megan as she handed Amanda her phone.

Bailey had just finished using the bathroom when Amanda quietly walked in. "Ok Bailey we do not have a lot of time so we need to get you ready. I just want you to know how much I appreciate you doing this for me baby. Now I am going to need to do something real quick that you probably will not like but it is for the best. We cannot afford anyone to notice anything odd and only see a teenage girl today so we need to hide your most obvious male sign. I am going to tuck you away so you look convincing and we can better protect your secret okay?" said Amanda.

Bailey wanted to scream he didn't want any of this, but again he had little choice. "Ok Mandy, whatever you think is best." Quickly with Bailey standing there, Amanda went to work following the helpful video. She first worked his balls until they popped back up into his body's natural cavity and then after wrapping his shaft in some tissue securely taped it tightly back between his legs leaving Bailey with a flat smooth groin area. "There we go that is much better. Now you will not show in your new clothes.

Oh and remember you will need to sit to pee when you're like that just like all the other girls. Now follow me we still have lots more to do to get you ready," said Amanda as she rose up and made her way out of the bathroom. Bailey wanted to throw up. This was just wrong; he looked down at his crotch in shock. It didn't hurt but it just felt wrong and uncomfortable. He just wanted to run but he knew he had nowhere to go.

Finally, with a sigh, he pulled back on his boxers and followed Mandy into their bedroom. Inside he saw Megan holding a box and smirking at him. "Okay so first things first Bailey, you need to lay down on the bed so we can get your new breast ready before we move on to clothes," said Megan taking charge as they all met in the bedroom.

Not wanting to cross her this early on Bailey did as she asked. Once he was laying down Megan began carefully placing the rather realistic-looking breast forms onto Bailey's hairless chest. After a few minutes, she was sure the glue had set, then used a special concealer that had been in the box with the forms to hide the seams. The finished product was rather impressive to all but the most expert eye it now looked as though Bailey had a nice set of natural c-cups breasts.

Bailey didn't like this at all. Looking down he was shocked they looked so real and looked huge from his perspective. Sitting up he was once again in for a surprise as the weight of them caught him off guard almost sending him toppling backward. "Don't you think these are a bit big Mandy?" asked an embarrassed Bailey.

"Unfortunately hun, they are all we have with such short notice. Plus they will help draw attention away from your face and help you fit in more. Oh and remember you need to start calling me Mommy, not Mandy and make sure you use the softer girl voice we worked on last night. We do not want any slips at the picnic do we?" said Amanda.

"Your right Ma...Mommy" said a red-faced Bailey in his aspirated voice still trying to get a handle on his new breasts.

Amused at seeing the blush come to Bailey's pale cheeks Megan started to pull clothes from a bag she brought. "Okay, so the next step is getting you dressed Missy. I was able to put together two outfits from what Becky left at home so I'll let you choose. You can either wear this cute top with a skort and sneakers or I have this pretty blue sundress with some cute wedges. What do you say girlie?" she said with a glint of mischief in her eyes.

Bailey looked over his choices, none of them good in his eyes. The sundress was obviously a no go he wasn't gonna be caught dead in a dress. But his other option wasn't much better. It was some lacy pink top and what looked to him like a short blue skirt. But Megan called it a skort. "What's a skort?" asked Bailey.

"Oh sweetheart it is a pair of shorts that are made to look like a skirt," said Amanda. "Ok, I guess I'll do that one then at least I get to wear sneakers with it," said, Bailey. "Great choice, you're gonna look so cute in it girl. Now one more question before we let you get dressed. I got you a couple of different color bras and some boyshorts. Which color do you want, I got some in black, white, pink, and blue. Which ones do you want?" asked Megan. "I think I'll go with black," Bailey started to say but was quickly cut off by Amanda.

"No black will not work honey, it clashes with your top. I think she should wear pink so her bra straps blend in more," said Amanda. Bailey all the while just burning inside as he heard his girlfriend call him her. "Okay pink it is, for our darling girl," snickered Megan. "Well if it has to be pink at least I get to wear boyshorts for a minute there I thought you were going to make me wear panties," the words dying on his tongue as Megan handed him his new underwear.

There was nothing "boy" about these shorts; they were some pink lacy affair. "Can't I just wear my boxers, it's not like anyone will see," pleaded Bailey after seeing what he would have to wear. "Afraid not. They would not sit right under the skort and would give you away," Amanda said holding up the blue pleated skort. "Now Hurry it up. This was your idea after all and we don't have time to waste. I'll turn around for a minute while you get them on," said Megan.

Defeated and ashamed Bailey pulled the offending garment up his now smooth legs. They were smooth lace in a pink floral pattern with a cute little bow in the front to top it off. They tightly cradled his flat crotch and didn't quite cover his butt. He was mortified and sickened by the sight and a little aroused by the feeling of the soft garment but didn't have long to think about it as Megan turned back around.

"Ok girl, let's get this show on the road, bra next," stated a bemused Megan handing over Bailey's first bra. Bailey fumbled with the lacy pink garment for a minute. He had plenty of experience taking one of these off but no idea how to get it on. Amanda came to his rescue and helped him do up the clasp, while Megan sat on the bed crossing her leg at the knee watching his struggle. "It's okay, every girl has trouble with her first bra honey."

Every second seemed to raise Bailey's embarrassment, and Megan's glee, and she just couldn't help, but tease him. Bailey just cringed inside at being once again spoken to like a girl before thanking her and moving on to the next item. He gently pulled on the pink top noticing how delicate it seemed and not wanting to damage the blouse and end up having to wear the dress instead. Once he got it on he was horrified to see that the lace was completely sheer leaving his arms covered by the flimsy lace yet leaving him feeling like he was on display.

Only having a darker pink lining over his torso that stopped just above his new tits. It was also completely off the shoulder leaving everything above his tits completely uncovered. Just wanting to get this over with he moved straight to putting on the skort next pulling it up his legs and then fighting his way into the shockingly tight little shorts inside that once on just barely hid his new panties. Finally fastening the skort at the side he was absolutely dismayed by how short it was. It only went to mid-thigh as the pleated skirt flounced about as he turned to see it from different angles.

"Okay, Bailey enough quaking get on your socks and shoes so we can move this along we don't have much time left. Amanda why don't you go get ready now and I'll help my niece get finished dressing and do her makeup. Then you can help me with her hair," said Megan as she saw Bailey getting ready to complain. "Okay sure. Bailey thank you again for being so willing to do this. It really is incredible. I will be right back," said Amanda as she hurried out of the room to get herself ready.

As soon as she heard Amanda's door shut she let Bailey. "So how do you like your outfit? Pink is definitely your color girl. Now get on those socks and shoes and come have a seat so I can get your makeup done. Oh and make sure you start acting more the part you really need to sell that 'you're doing this willing' so no more complaints from you or else my phone and that video might just end up in my little sister's hands.

You don't want that now do you, my cute little niece," said Megan with a threatening laugh. "Okay you win Megan, let's just get this over with I don't want to wear this stuff any longer than I have to," said Bailey as he sat down and pulled on the socks which it turned out weren't normal socks at all but thigh high stockings made to look like socks. Something a guy might imagine on a cute little school girl. He then quickly slipped on a pair of pink converse sneakers.

While he hated more pink at least they weren't heels. Finally dressed he went and had a seat at Amanda's vanity to let Megan do his makeup. "Please Megan just help me here there's no way I'm going to fool anyone like this," said a worried Bailey. "Oh don't worry once I'm done no one will see you as the little perv that you are. All they'll see is the cute little blonde ditz we want them to see.

Now be still," said an irritated Megan as she began applying makeup. She started by applying a light coat of concealer to hide any blemishes and to get rid of the dark circles under his eyes. Next, she worked to apply some eyeliner and soft pink eyeshadow to make his eyes look a little bigger and really pop.

Once that was done she began using several coats of high-volume mascara to give him nice big bold lashes. She decided he was missing some color and noticed his empty ears. Reaching into the bag of Becky's things she had brought she pulled out and clipped some pink flower earrings on each ear. Happy with her work so far she worked to finish her canvas with his lips. She was really looking forward to this part.

She had found some interesting lipstick when she was going through her daughter's things. It had lip plumper in it supposedly giving anyone who used it nice kissable lips in no time. She applied a generous amount of the pink lipstick before going over it with a shiny pink strawberry-flavored lip gloss to seal them and give his lips a nice kissable shine.

Suddenly Bailey began to feel a tingle in his lips it started small and grew stronger before it stopped leaving them feeling a little numb. He quickly brought his hand up to feel his lips finding them much bigger than expected. "Wa dud you do u my ips!" cried Bailey as he found he now had trouble speaking properly with his plump new lips.

"Oh that is just too good," laughed Megan. "I just added a little of Becky's plumping lipstick don't worry it's only temporary but it makes your lips so kissable and cute. And hey as an added bonus I will help make sure you don't get too chatty. I'm sure If you try hard you can make your words come out normally but it will require you to put in more effort so it will add to your cover as a little airhead. No more big words for our little girl.

Ok, you should be good to go now, girl. You actually turned out surprisingly well. I went for a fun but not too sluty look. I know you usually prefer your girls a little trashier but I didn't want you to reflect poorly on my sister. Ok now when Amanda gets back we can get your hair done and then you too can get on the road and remember no more complaints.

Just then Amanda reentered the room wearing a pretty summer dress in a blue floral pattern. "Oh my! Bailey, I almost did not recognize you. Megan, you did a fantastic job, you maybe leaned a little more into the stereotype than I would have but I am sure that will just help her blend in. Okay, so all we need to do now is her hair and we can go. Which is good. I do not want to be late and we are cutting it close.

What did you have in mind Megan?" asked Amanda who was now all business as she was getting nervous about making a good impression on her boss and securing her promotion. Bailey just stared dejectedly. He had hoped when Amanda saw him she would object to how Megan was making him look, but she hadn't. She had just taken it in stride and kept referring to him as her. It was beyond emasculating.

"Well I was thinking maybe some cute little pigtails," Megan said as she finished brushing out Bailey's just more than shoulder-length wavy blonde hair before pulling some to each side and securing them into pigtails with hair bands. Bailey just wanted to die of embarrassment at this point and they hadn't even left the apartment, the pigtails made him look like a little girl sitting at her mommy's makeup table. "Pwease no anyting but this," whined Bailey.

"No, I think she's right Megan the pigtails make her look too young. What about a nice French braid? That would look girly enough to keep in character but be less hassle to deal with," said Amanda. "Oh that's a great idea, give me just a second," said Megan as she went to work taking Bailey's hair down and then braiding his hair into a single traditional French braid. Leaving the end of the braid hanging slightly over his shoulder after tying off the braid with a pink hair tie.

"Oh, she just looks adorable. I cannot believe that is my Bailey sitting there," said Amanda clasping her hands together with a beaming smile on her face. "Why don't you stand up and give us a nice girly little twirl Bailey," said Megan giving Bailey a look that just dared him to challenge her. Not willing to take that dare to go against Megan at this point. Bailey stood and as girlishly as he could give a twirl showed off the finished product to the two women. He hated every second of it.

Everything felt wrong his new tits bounced in the bra while the short skort flounced out almost revealing the little shorts underneath. "Oh that is great I think we might just pull this off," said Amanda proudly before looking down at her watch. "Just in time, we need to head out. Megan thanks for all your help." "No problem sis. Why don't you go grab your purse and Bailey can meet you at the car? I see one more thing I need to touch up on her makeup but she won't take but a sec," said Megan.

"Ok sounds great I will see you in the car in a second Bailey. I just cannot tell you how much I appreciate all you are doing for me. I love you, baby," Amanda said as she left the two alone and headed for the car. As Amanda left Bailey took advantage of his first free moment to walk over to the full-length mirror on the back of the door and take a look at himself.

What he saw sent a wave of emotions through him, shame and embarrassment foremost but then a little thread of relief mixed in because seeing himself for the first time made him realize he might just be able to get through this without being found out. When he looked in that mirror he didn't see himself in drag, no what he saw to his utter shame was a hot little teenage girl that might have passed as his sister but was never an adult man.

His hair was cutely tied in its braid making his long blonde hair look even girlier. Continuing down to his face he was the perfect example of a teen girl's idea of sexy. Pink eye shadow that matched his outfit and long fluttering lashes covered in mascara. He was aghast when he saw his lips looking plump and kissable with an inviting pink shine from the lip gloss.

Down his eyes traveled coming to a stop on his lacy floral pink top. It just screamed girly-girl. Not to mention his lacy pink bra straps in plain view just adding to his embarrassment. The blouse clung to the C-cup breasts and while he knew the large tits were fake, they didn't appear to be. Moving on to his lower half he cringed when he saw the effect the little skort had when combined with the over-the-knee stockings.

He had been happy at first to have the extra coverage on his legs but now realized that was a mistake. The effect of them together just drew more attention to how short the skort was drawing everyone's eyes to the flesh that was still exposed on his lower to mid-thigh. He hated the way the skirt seemed to flounce and shift around every time he moved making him super self-conscious and worried about exposing the surprisingly small shorts underneath.

The only part of this get-up he was thankful for was the sneakers. While he hated the pink color he was happy to not be stuck in something girlier like heels. Sighing Bailey began walking to follow after Amanda before he was quickly blocked by Megan. "Oh no we need to have a little chat bitch.

Now listen and listen well you better do your absolute best to convince every last person today that you are just the sweetest little blonde bimbo they have ever met. Today is going to go perfectly for Amanda or so help me I will ruin you. Do you understand?" Megan said with unbridled venom in her voice. "Yesh I under... I like to get it ok? I'll make sure mommy's day goes super," said Bailey in the best impression he could do of the blonde airhead he appeared to be.

"That's great girl, just keep that up and you'll be fine. I bet the boys will just eat you up. Oh here's your purse I put a couple of essentials in there as well as some of your lip gloss so you can freshen up as the day goes on, in fact, you should probably make sure to check your makeup in the little mirror I put in there as well every so often. You wouldn't want it to get messed up and give away your boyish features underneath," said Megan as she placed a little pink leather purse on Bailey's

shoulder.

"Now get your ass out to that car. I'll lock the door behind me after I clean up." Finally free of his torturer Bailey made his way out to the car and after one last thought of running away got in the passenger seat next to the women he loved, the women he had cheated on, and the women who were completely oblivious to the control her sister now had over him.