Orange

“I like the orange one,” he said sifting through her panty drawer.

“Really?” she asked with raised eyebrows.  “I don’t think that it will, uh, flatter you.”

“Oh well, I still want the orange one.  I promise I won’t stretch it out.”

            He looked at her with puppy dog eyes and she grudgingly slapped the orange satin garment into his hands.

            “I am of course going to be needing the matching g-string and a few pairs of socks for padding too,” he told her in a very matter of fact manner.

            “Yeah, of course.  What was I thinking?” she sarcastically grumbled.  “You and your fucking ass floss obsession… Geez…”

            “Well your full coverage stuff is all so boring.  Sorry.”

            “You’re just lucky you’ll look so goddamn cute in it or I’d make you buy your own.”

            “Pssh, like I could afford that!  It’s not like I do this everyday or anything.  What if I don’t like it?”

            “Then we won’t have to do it again.  This was your idea, not mine.  I’m just along for the ride.”  She dug around the drawer and after finding the orange panties, she flung them on the bed where they landed next to a black and purple, corset-top dress with matching mini-jacket and a strappy pair of size eleven fuck-me pumps.  “So now that we have all of that taken care of, where do you wanna begin?”

            “Um… I don’t know… What do you think?” he asked innocently.

            “I think that if you want to be able to pull off wearing that you’ll have to get all of your hair… here, here and here,” she said pointing to his arms, legs and underarms.  “And if you really want to get into it you can get, uh, everywhere else in between too if you catch my drift.  How far do you want to go with this?”

            “As far as I can without doing anything permanent,” he said calmly.  “Now how exactly does Nair work?  Does it hurt?”

            “No, it doesn’t hurt, and it works pretty well, but it smells horrible.”

            “Let’s do that then, sounds better than trying to shave.”

            “Alrighty,” she sighed, fishing the Nair out from the back of the bathroom cupboard.  “But you are on your own for this part.  Take this and spread it over everything you are getting rid of, but don’t rub it in!  Leave it on for like five to eight minutes and then wipe it off with a washcloth in the shower.”

            “Sounds easy enough.  I guess I will be seeing you in five to eight minutes then,” he said taking the bottle from her hand.

            “Eh, it will take a while to apply.  Plus you will want to try and smell as little like that as you possibly can afterwards.  I bet I’ll see you in about twenty,” she laughed.

            He shut the door and she began to search through her things to find any items that would aid in the unconventional transformation.  A pair of tweezers, a few crappy makeup kits, some hair accessories and some cheap jewelry was all she could muster up.  A few moments later he came out of the bathroom all silky smooth.  He had a nice body and the towel was just barely wrapped around his waist.

            “Mmmm… If we weren’t both so into this kinky role reversal thing, I’d fuck you silly right now,” she said, biting her lower lip.

            “Well, I mean… if you really want to…”

            “It’s okay.  I can be good and wait.  I’ve never got to do this before and I want it to be something different.  And if it ends up not working out we can always just do things the good old-fashioned way,” she smiled.

            “Alright.  Well, I’ve taken care of the whole hair thing.  Now what?” he asked looking at the floor, slightly embarrassed.

            “I’m going to pluck your eyebrows,” she said with an evil grin, snapping a pair of tweezers in his general direction.

            “No you’re not.”

            “Aww, why not?” she whined.

            “Because after everything is all said and done, I’d still kinda like to look like a guy, thanks,” he said dryly.

            “Fine, fine.  No eyebrows,” she pouted.  “I found these bracelets and stuff that you can wear with your outfit.  Look, these match!”

            He raised an unplucked eyebrow at her.

            “I wanna dress up like a chick, but I’m not a fag, Janae.”

            “Okay, okay… Let’s see… How about you try on your little ensemble and we can do your makeup when you’re done?”

            “Alright,” he said gathering up the pile of feminine fabrics from the bed and heading into the bathroom again.

            About five minutes later he emerged.  The dress cut off just above the knee and his shoulders were just a bit snug at the top.  The mini-jacket covered up his muscular arms nicely, and his new, lopsided breasts were made large enough to make his shoulders look a bit smaller.  It was a good thing she wore such a large bra size.

            “So, your boobs are kinda lumpy and crooked, but once we fix that I think you’ll like it.  Did you wanna go conservative or French whore with the makeup?”

            “Hmmm… You only live once.  Let’s go high class whore,” he laughed.

            She applied everything with great skill and gave him full, bright red lips.  The foundation covered up traces of stubble and evened out his skin tone.  He flinched a bit with the eyeliner and even more with the mascara.  After a bit of lavender eye shadow to set off the purple in the dress, she was finished and handed him the mirror.

            “Holy crap,” he said staring at his perfect lips in the reflection.  “I’m not gonna lie, this is already starting to turn me on.”

            She rubbed her hand along the front of the dress and felt him nice and stiff underneath.

            “God that’s nice,” she said softly, looking into his gorgeous brown eyes that were currently sporting supermodel eyelashes.

            “But we are going to do that other thing that we talked about first,” she said taking her hand off his cock.  She threw the shoes at his feet and stood up.  “Here practice walking in these while I go and get ready.  I don’t want you falling on your ass in public.”  She left for the other room, when she forgot something and turned around.  “Oh, and think of a good name for yourself.  Johnny isn’t exactly the hottest chick name.”

            “Yeah, thanks,” he said, fastening the straps on the fuck me pumps.

***

            The pumps were killing his feet as they walked though the mall.  She held his hand and he held her purse as they walked along, passersby giving them strange looks but not completely surprised.  It was the Bay Area after all.

            His hair was pushed up into a kind of stylized poof with the help of a purple headband and they fixed his chest before they left so that it looked somewhat believable.  They weren’t there to shop; they were there to let him see how it would feel.  He didn’t know any of these people, and never would, so he didn’t care what they thought, but he did want to see how they would react. 

            Some people didn’t really notice, but some pointed and giggled.  A few winked at him and a few even winked at her.  She was kind of enjoying the fact that in a few hours she was going to be in complete control of this person that so many people couldn’t keep their eyes off of, and he was loving the attention.

            “Are we almost done fulfilling your attention whore fantasy?” she asked him in a lyrical tone.

            “Almost,” he said.  “Let’s, like, go into some fucked up store like Abercrombie or Sports Authority and see if we can make some really conservative people uncomfortable!”

            “Okay,” she replied gleefully.  “Oooh, we could go into Ann Taylor and make old ladies cringe!”

            “Sounds like a plan,” he agreed.  “But remember, you said you’d buy me dinner, and I’m not a cheap date.”

            “Of course you’re not sweetie,” she said mockingly. “Of course not.”

            After about three hours of just walking around people watching, they left the mall and sat down to eat at a quiet restaurant.  The waiter was kind of a dick, so they took their dessert to go and only left him a one dollar tip.  When they got back in the car, she ran her hand up his thigh, underneath the skirt.

            “I can’t wait to rip that off of you when we get back to my place, sweetie,” she said in a cautiously seductive voice.  She could hear him swallow hard and he couldn’t think to respond to her with anything more than a meek little “Okay.”  She kept her hand on his leg and put the car into gear.

***

            “So what’s your name, sugar?” she said from the bed, a vast array of toys in several shapes and sizes spread out on the comforter.

            “Uh, Julie,” he said softly.

            “Well, Julie, you look like a nice girl,” she said with all the confidence she could muster.  “You haven’t done this kind of thing before, have you?”

            “No, sir.  I haven’t”

            “Then let me tell you how this is going to work.  For the rest of the evening you are going to be my cheap little whore.  You are going to do what I say, when I say it, and if you are good, the money will be left on the nightstand and you can collect it on the way out when we’re through.”

            He stood there in silence, not exactly sure what to make of all that, but could feel himself starting to stand at full attention beneath the orange satin.

            “Do you understand, Julie?” she said sternly.

            “Yes, sir.  I understand perfectly.”

            “Good.  Then you can start by taking those clothes off.”

            He started to shimmy out of the jacket when she stopped him.

            “No, not like that,” she said with mock frustration.  “Slowly.”

            He peeled the jacket off the rest of the way and unlaced the corset-top with a great vigor.  She watched the dress slide off the rest of his smooth body and motioned for him to come closer.

            “Leave the shoes on,” she commanded.  “I like how they look.”

            “Ugh, but they hurt so bad and—“

            “Excuse me?  But were you just disobeying me?  I said leave the fucking shoes on and get over here.”

            “Yes, sir,” he said somewhat wearily.

            She grabbed him by the waist and pulled him over to the edge of the bed.  She ran her hands down his curveless body and spanked him lightly on the bottom.  She smirked a bit and he couldn’t stop staring at the ceiling.

            From the pile of bedroom toys she found what appeared to be a brand new strap-on and removed it from its packaging.  She slid it over her hips and liberally applied some strawberry flavored lube.

            “You are horribly naughty, and I can just tell that you want it badly,” she said in a deep sexy voice.  “Now get over here and suck this cock.”

            “Uh…”

            “I wasn’t asking, Julie.  Get down on your fucking knees and get ready for me.”

            “But… I…” he drifted off, slowly dropping to his knees, slightly confused and unsure of himself.  “I mean, it’s not like you can feel it… Do I really have to—“

            And with that she grabbed the back of his head and shoved all six inches of the strawberry flavored latex down his throat.  He gagged and coughed and tears welled up in his eyes, but he eventually took it without complaining.

            “Look at me while you’re sucking my cock, Julie.  I like it like that,” she added softly, forcing him to bob up and down on her newly acquired phallus.

            His eyes moved up to stare into hers as red lipstick was smeared all over the instrument.  She ran her fingers through his hair and yanked him off of her as the fake cock came out of his mouth with a soft pop. He wiped the saliva from his mouth and rubbed his sore jaws.

            “That really wasn’t necessary,” he said.  “And it was pretty demeaning.”

            “Welcome to the wonderful world of sex as a woman, Julie,” she said emphasizing the last word to remind him to stay in character.  “Now let’s take off those sexy undergarments and let the real fun begin.  Get the lights.”

            She wrapped her arms around him and took off the bra, ignoring the rolled up socks tumbling to the floor.  She tossed it to the ground and slid the panties off of him exposing him, rock hard.  She ran a finger across his crotch.  It was her lucky day.  He had used the Nair there too.

            “Very nice there, Julie.  Now get on the edge of the bed.”

            She pulled him back to the edge as she stood up over him and spread his legs apart, rubbing his backside with soft hands.  She grabbed the bottle of lube and reapplied it to the strap-on, and a bit on to him.

            “Mmmm, it looks nice and tight back here, missy.  You haven’t done this before, have you?”

            “No, sir, but I’ve always been kinda curious to try it,” he said in his best innocent voice.

            “Well don’t you worry about a thing.  I’ll be gentle.”

            And with that she slid a finger inside of him.  He clenched up tight and she could barely get it out.

            “Shhh, don’t worry sweetie.  I’m an expert.  I won’t let you get hurt.”

            “You promise?” he asked her honestly, not as a scared little girl, but a nervous young man.

            “I promise,” she said, spreading him apart as far as she could.  She let some lube drip out directly from the bottle onto him and the cold liquid made him flinch a bit.  She put the tip of the strap-on right in position and before he could say another word she slid it inside of him as he shuddered.

            The pressure inside of him was something that he had never experienced before, and he felt rather peculiar as she started to move it back and forth inside of him.  A sinking feeling in his stomach came and went as she grabbed him by the hips and began to thrust herself into him.  She could sense his apprehension and started to creep around the front of him while he was distracted by the faux cock in his ass.

            She reached around and wrapped her fingers around his cock, stroking it in time with the undulation of her hips.  He moaned loudly as she rammed it into him while playing with the tip of his steel manhood.  She knew he was probably about to cum, but she wasn’t ready for him yet.

            “Alright, darling.  Just one more thing and then you can have your precious orgasm,” she told him very casually while sliding the strap-on out of him gently. 

            She rummaged through her pile of fun accessories in the dark as he moved to the middle of the bed.  He never imagined it could feel like this.  She let out a sign of pleasure as she found what she was looking for and in the small trace of moonlight coming through the window he saw what looked like a giant toy with two heads and his eyes got rather wide.

            “Don’t be scared, sweetie.  You aren’t the only one who likes it up there.  We are going to have a little contest to see who can get whom off first.  Loser cleans up,” she smiled, winking at him in the dark.

            She took off the strap-on and gave them each a nice amount of lube to prepare themselves for the brutal new toy they were about to share. 

            “Now you get over on this side, and I’ll get over on that side.  Put your ass up against mine and I’ll put it between us.  It should slide right into you since we have you all nice and warmed up,” she giggled.  “This is just a tiny bit bigger than the last thing you had in there, but you’re a good girl, so I think you can take it.”

            She heard him swallow nervously and she backed herself into him.  After a little more lube she slid the tip into him and positioned the other tip right at her tight hole. 

            “When you’re ready, you just go right on ahead and push yourself into me.  Don’t worry, the part in the middle is super thick, so we won’t be losing anything.  And when it’s nice and deep inside of you, you can start touching yourself, as will I.  You aren’t allowed to cum until I do though, so pace yourself.”

            He stayed still on the bed, bent over with the tip of a giant toy inside of him.  He couldn’t seem to move at all, so it came to somewhat of a surprise to him as she took the initiative and began to press against him, causing the toy to force its way in, ripping him apart just a bit.  He cried out and started to stroke himself to ease the pain.

            “That’s it, Julie.  Take it all in.  Fuck yourself hard.  I know I will be.”

            Eventually they got a nice rhythm going and the sound of flesh pounding against flesh and heavy panting was all that could be heard.  She rubbed herself like she never had before and he stroked himself so hard he thought it might just fall off. 

            “Oh my God,” she cried out, “I’m going to cum!  Do it with me, please!”

            “I’ll try,” he panted. “I’ll try!”

            And as their hips moved in time with one another and the neighbors upstairs complained about the noise, they each hit climax, their chests heaving and their pain subsiding.

            “Jesus that was good,” she told him, turning around and removing the toy from within them.  It felt absolutely amazing as she took it out and their bodies convulsed ever so slightly. 

            She got up to get everything cleaned and put away and almost fell over from the dizzying ecstasy that her body had just endured.  He lay back as she moved everything around him and just stared at the ceiling, thinking about what just happened, completely forgetting that he was still wearing the uncomfortable shoes.

            She turned on the lights and brought him a warm washcloth to wipe all of the makeup off of his face and when he was all clean she wrapped her arms around his neck and kissed him passionately.

            “So how did the whole girl experience work out for you, huh?” she said looking him dead in the eyes.

            He looked at the shoes he still had on for some reason, looked at the box of toys pushed to the floor and looked into her gray-blue eyes.  “Well, it was fun, excruciating, and most importantly, a giant pain in the ass.”

            They both looked at each other and laughed and went to bed thinking of the night that neither of them would ever forget.