Getting a "girl" ready

“Ok sweetheart it’s 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 slowing 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 **** 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 help 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’s so sweet of him. I just can’t believe he’s 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 want 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 seem strange but we can’t afford for 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 don’t 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’m going to need to do something real quick that you probably won’t like but it’s for the best. We can’t afford anyone noticing your anything but a teenage girl today so we need to hide your most obvious male sign. I’m going to tuck you away so you look convincing and we can better protect your secret ok?” said Amanda.

Bailey wanted to scream inside he didn’t want any of this, but again he had ****. “Ok Mandy whatever you think is best.” said Bailey.

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 bodies 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’s much better. Now you won’t show in your new clothes. Oh and remember you will need to sit to pee when your 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 no where to go. Finally with a sigh he pulled back on his boxers and followed after Amanda.

“Ok 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 on to Bailey’s hairless chest. After few minutes and she was sure the glue had set she used a special concealer that had been in the box with the forms to hide the seems. 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 backwards. “Don’t you think these are a bit big Mandy?” ask an embarrassed Bailey.

“Unfortunately hun they’re 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 don’t want any slips at the picnic do we?” said Amanda.

“You're right Ma…Mommy.” said a red faced Bailey in his aspirated voice still trying to get a handle on his new breasts.

“Okay so next step is getting you dressed Missy.” as she pulled clothes out of the bags and lay them out on the bed. “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 yellow sundress with some cute wedges. What do you say, girlie?” said Megan 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?” ask Bailey.

“Oh, sweetheart it’s 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 your gonna look so cute in it girl. Now one more question before we let you get dressed I got you a couple different color bras and some boyshorts. Which color do you want a got some in black, white, pink, and blue. Which ones do you want?” ask Megan.

“I think I’ll go with blue.” Bailey started to say but was quickly cut off by Amanda.

“No blue won’t 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 a her.

“Ok 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 not like anyone will see.” pleaded Bailey after seeing what he would have to wear.

“I’m afraid not. They wouldn’t sit right under the skort and would give you away.” said Amanda.

“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 sicken by the sight 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.

Bailey fumbled with the lacy pink bra 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. “It’s okay every girl has trouble with there first bra honey.”

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 it and end up in the dress. Once he got it on he was horrified to see that the lace was completely sheer leaving his arms cover by the flimsy lace yet completely 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 into putting on the skort next pulling it up his leg 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 flounce about as he turned to see it from different angles.

“Ok 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 Bailey 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.

“Ok sure. Bailey thank you again for being so willing to do this it really is incredible. I’ll 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 into 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 your doing this willing so no more complaints from you or else my phone and all it videos might just end up in Amanda’s hands. You don’t want that now do you my cute little niece.” said Megan with a threatening laugh.

“Ok 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 witch 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 eye shadow to make his eyes look a little bigger and really pop. Once that was done she began using several coats of a 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 a 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 tu my ips!” cried Bailey as he found he now had trouble speaking properly with his plump new lips.

“Oh that is just to good.” laughed Megan. “I just added a little of Becky’s plumping lip stick don’t worry its 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 to 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 good. I went for a fun but not to slutty 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 didn’t recognize you. Megan you did a fantastic job, you maybe leaned a little more into the stereotype than I would have but I’m sure that will just help her blend in. Ok so all we need to do now is her hair and we can go. Witch is good I don’t want to be late and we are cutting it close. What did you have in mind Megan.” Ask 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 stare on 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 a her. It was so 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 hairbands.

Bailey just wanted to die of embarrassment the pig tails made him looker like a little girl sitting at her mommy’s makeup table. “Pwease no anyting but dis.” whined Bailey.

“No, I think she’s right Megan the pig tails make her look to young. What about a nice French braid. That would look girlie 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 can’t believe that’s my Bailey sitting there.” said Amanda.

“Why don’t you stand up and give us a nice girlie little twirl Bailey.” said Megan giving Bailey a look that just dared him to challenge her.

Not daring to go against Megan at this point Bailey stood and as girlishly as he could gave a twirl showing off the finished product to the two women. He hated every second of it. Everything felt wrong his new tits bounced in there bra while the short skort flounced out almost revealing the little shorts underneath.

“Oh that’s great I think we might just pull this off.” said Amanda proudly before looking down at her watch. “Just in time too, 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’ll see you in the car in a second Bailey. I just can’t tell you how much I appreciate all your doing for me I love you, baby.” Amanda did 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 never an adult man. His hair was cutely tied in its braid making his long blonde hair looked even girlier. Continuing down to his face he was the perfect example of a teen girls 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, they looked plump and kissable with an inviting pink shine from the lip gloss. Down, his eyes traveled coming to 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. 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 everytime 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, were 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 ever have 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 is her voice.

“Yesh, I under… I, like, 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 refresh 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 was completely oblivious to the control her sister now had over him.