Scene 8

“Isn’t this a little much? Or a lot much!?” Jackson was looking in the standing mirror his sister had in her flat. After spending longer than he thought was possible shopping they came back here to get him ready for his date. His sister was blowing it way out of proportion, but he felt helpless to stop her. Every objection he voiced she had a rebuttal for and after what she thought was too many she had threatened him with sending a photo of them together to their father. “You keep this up little sis and I will send a photo of us to our dear ol Dad, I bet he would be very accepting of you. Or I could tell him it is a photo of me with my good friend about to hit the club and ask him what he thinks of Jacqueline? Wouldn’t you like to know if Dad thinks you're pretty?”

So his objections stopped, and he let his sister do her thing. Madison put his hair up in hot curlers, making him help. Then she had him roll some tan stay up stockings up his legs with a patterned welt at the top. Just as before feeling the material on his smooth shaven legs felt sensual, it made him wonder why girls didn’t wear them more often with how great they felt coming on or when he rubbed his legs together. Though he couldn’t keep doing that or he was sure his tucked backed dick would show in the lacy black panties he had to wear.

“I have never had a girl wear stockings on a date with me.” He started to object again when Madison gave him a hard look before breaking off into laughter.

“Maybe they didn’t think you were worth it, but Jacquiline is the type of girl that loves feeling sexy and considering how she demanded this boy be her boyfriend, she is definitely the type to make it worth his while.”

“I don’t want to make anything worth anyone’s while!” He felt her slap the side of his thigh lightly.

“Jacqueline, I know you are a ditzy girl, but you need to stop this nonsense and remember who you are. You love feeling pretty and sexy. You love wearing dresses, stockings and heels.” Madison then leaned closer, talking in a softer voice. “The girlier you are the less chance anyone has to see through your disguise. Now tell me what you love.”

Walking around dressed up like a girl was bad enough, but the idea of people looking at him and calling him a freak was much scarier. “I love looking pretty and feeling sexy and… and want my boyfriend’s full attention on me.” He knew the voice was his own, but the husky voice saying those words caused a small twitch in his panties.

“Yeah you do, and with my help he won't be able to take his eyes off you or keep his hands to himself.”

“I don’t…” Jackson stopped his objection when his sister slapped the side of his thigh again.

Soon he had on a black asymmetrical dress with white around the edges. It didn’t go very far down his legs, but it was enough that if he was careful he was pretty sure no one would see the tops of the stockings, though he wasn’t sure if that would hold true when he sat down. His makeup was done up to be a dramatic night time look, his lips felt puffy from something Madison had put on his lips before adding lipstick, his eyelashes were long and dark from the mascara. The mascara along with the reddish eyeshadow made his eyes feel heavier, but nearly as heavy as his ears felt with the gold double hoop earrings that now hung from them. The gold earrings were paired with a gold and pearl bracelet and the last thing to go on was a pair of three inch pointed toe heels with a thin strap. He wasn’t even sure how girls handled the tiny straps on their heels now that he was experiencing life with longer nails.

“You look hot girl, your boy won't know what hit him.” He stood there looking at himself in the mirror not sure where he went and how he was replaced with this smoking hot girl. Hardly taking notice that his sister had changed into a brown leather mini-skirt with a tight three quarter sleeved forest green blouse that had a plunging neckline.

“If Linc touches me he will learn quick who will hit him.” This time he felt his sister slap him on the ass, much harder than she did when she hit his thigh earlier. It caused him to jump slightly in surprise.

“If he wants to be a little amorous you need to let him, you are a couple and need to look like you are together. Remember the point of tonight is for some coworkers to see you out with him, so they know you are taken. If you learn to relax a little you might even have some fun, or get lucky.” Madison gave her feminized brother a wink in the mirror, before slapping his ass one last time as she saw the scowl on his much prettier face. “A ditzy girl like you smiles, always remember to smile little sis.”

Jackson turned away from the mirror looking at his sister. “Maddy, I can’t do this. The mall was one thing, and I think I am going to hyperventilate at the idea of having to work like this… but a date! Looking like this! I just can’t!”

“You can, I know you can. You are dressed up sexily and that gives a girl more confidence. Close your eyes and tell yourself that it gives you confidence.” Jackson looked at his older sister giving her a pleading look, but when she didn’t budge he did as she said. “I am confident, I can go on this date, wearing sexy clothes makes me feel confident and because I’m wearing them now I am confident.” Opening his eyes he gave a small shake of his head. “It isn’t working.”

“Of course it isn’t, you are trying to be Jackson dressed up in drag instead of being Jacquline ready to go out on a date with a boy she likes. You need to be Jacquline, tell yourself that is who you are. Now go ahead and close your eyes and say that again five times.” Again he did as his sister told him, wondering why he was being so compliant for her, he was normally trying to take command, ignoring her as she tried to tell him what to do, but dressed like this he felt so much more timid… and afraid. Afraid someone was going to see through him, worried that he liked the feel of some of the clothes he was wearing. Not the corset or heels by any means, but the woman's clothes were so much softer and he shouldn’t be enjoying it.

When he was done repeating the lines he still didn’t feel any different, but when he opened his eyes his sister was standing in front of him holding out a small glass of water in one hand and two pills in the other. “If that doesn’t work you can try taking a Xanax, take one now and…” Madison stopped talking as her brother threw back both pills and drained the glass of water, leaving a lipstick stain behind.

“Or you can take both… okay, well by the time we get there you won't be worried I bet”

“Good, because I’m freaking out now Maddy.”

“You can do less freaking out and more repairing your lipstick like I showed you. Here is your purse with everything you will need tonight.” Taking the purse from her, Jackson noticed for the first time how his sister was dressed up wearing stiletto heels an inch taller than his own heels, making her slightly taller than him.

“You going somewhere?” She smiled, turning him back to the mirror so he could see them both standing side by side again.

“Of course, I will be at the same bar, keeping an eye on my little sister. You can take some selfies with your man and I will take a few other photos so you can have something to put on your desk at work. That… and might also feel the need to take a strapping young man home with me. Can’t have my little sister be the only one getting lucky.”

Ignoring her teasing, Jackson opened the little clutch purse, seeing much more than he expected in there. Lipstick, mascara, a compact, tissues, a few condoms, a twenty dollar bill and his keys. Pulling out a condom he held it between two fingers, giving his sister a serious look. “I won't be needing these.”

“You don’t want to use protection, that is your call, I would have given you a travel size mouthwash, but I forgot to get one while we were out.”

“Maddy, I don't need mouthwash!” Madison rocked her head back and snickered.

“I’m not big on the taste of cum, but more power to you little sis.” He glowered at her some more before stuffing the condom back into the purse, snapping it shut in a huff. Forgetting the purpose of opening it was to fix his lips. He hated that they looked so plump and kissable, if he was dating the girl in the mirror he would like to do just that and much more. Linc better be on his best behavior he thought as he opened the purse back up.

When Lincoln opened the door he wasn’t sure what he was expecting, but it was definitely not to see two smoking hot women on the other side. Both looked like they were ready for a night out on the town, he instantly felt his member twitch, awakening to the sight of the sexy ladies. He had always had a crush on Madison from the first moment he met her, when she texted him from Jackson’s phone earlier he thought he was about to get his wish. Till she told him how he would be going out with Jackson in drag instead. Sure he looked pretty as a girl, but that didn’t matter, it was still Jackson. That thought went out the window seeing the vixen next to Madison. He ran his eyes up and down the sexy girl twice, opening his mouth to say something, but his mind gave him nothing to work with.

“Cat got your tongue? Or were you just thinking how you want to use it when you kiss Jacqueline here?”

“There will be none of that.” Jackson said, adding a light laugh to the end as he blinked his heavy eyes, a small smile coming to his face as he pressed his stocking covered legs together. The pills he had been given were doing exactly what his sister said they would. The idea of Linc kissing him was funnier than frightening.

“Relax sis, I told you the two of you need to look like a couple. So, I better be seeing at least a little kissing if you want to sell this act. Unless of course you want to go back to being single. Some men in your office would love that I'm sure and we can go check out men together tonight instead.”

It took a few seconds, but Lincoln pulled himself out of his daze. Jackson did look sexy as heck and he would never guess this person to be male, but he knew better and all this boyfriend BS wasn't his idea. “That sounds like a good plan, the two of you go out and have a good time. I will just stay home and not spend the money that I can’t really afford to spend and watch tv.”

“Oh no, I spent so long getting ready for this date.” Jackson paused to get his thoughts in order. “If I have to go out looking like this, then you are coming too.” Lincoln ran his eyes up his friend’s legs one more time, hating himself a little for being attracted.

“You heard your girl lover boy, grab whatever it is you need to grab and we can head out.”

“Why is he acting like that?” Madison gave a lopsided grin to her brother.

“Because SHE.” Madison paused looking her brother's friend in the eye. “Took two Xanax instead of one. So it would be best if my little sister didn’t have any **** tonight.”

“I’m going to a bar and I can’t drink? That is so unfair.” Jackson looked at his friend; he wasn't nearly as dressed up. Wearing dark jeans, the dress shoes he should wear to work more than he did and crisp ironed dark blue shirt with gray suspenders. Jackson wished he could have spent so little time getting ready, Linc was so lucky. A smile crossed his lips and a slight giggle at the word lucky before an idea struck him. Linc had to be his boyfriend, so he could just steal his drinks if he wasn’t allowed to get his own.

“Why are you smiling so much?” Lincoln asked his feminized friend.

“Because you are going to buy me a drink tonight because I’m a girl or I’m just going to take yours.” Lincoln nodded slowly, looking over to Madison, happy to be having the chance to look at her.

“This is what I’m working with?” Madison shrugged, then pulled him out of the doorway and into the hall. Reaching past him to close the apartment door.

“What can I say, your girlfriend is a bit of a ditz, well I can say that and tell you to make sure any of your coworkers know the two of you are a couple at a glance. No scratch that, everyone, no telling who is a friend of who and how rumor spreads.”

“I really don’t want any rumors about me.” He glanced back at the now closed apartment door, he didn’t need anything inside, but he wished going back inside was an option.

“That can’t be true, from what Jacqueline is telling me this secretary job won't last long and wouldn’t it benefit you if she spread rumors about how amazing a boyfriend you were and maybe giving little hints of your prowess in the bedroom?

Lincoln took a few seconds to ponder that, an improved reputation around the office was a much better sell then the threat. Jackson wanted to join the sales team, he should have led with that proposal. He teetered his head back and forth a second mulling that over, knowing the threat was still the only real reason he was still doing this. The offer just made it easier to swallow. “Sure, why not.” Lincoln took Jackson by the hand, looking him over for a third time. Trying to convince himself that there was nothing wrong with going out with such a pretty girl. Dick or no dick under the skirt the way this person looked he would have to be gay not to feel attracted to the beauty.