Categories > Original > Drama1 Reviews
Rated for language and cross-dressing. Shaun unintentionally insults his best friend and she makes a bet with him. If she wins he has to let her turn him into a girl for an entire week.
Summary: Shaun loses a bet with his best friend and as a result he has to let her turn him into a girl for an entire week.
Warnings: Language, cross-dressing.
Notes: Inspired by the Madonna song of the same name.
Disclaimer: None needed. It's all mine.
It started out as a bet, a bet I was sure I couldn't lose. I lost. And to Jessica of all people. Jess was, and still is, my best friend. But we fight constantly.
"Girls can wear jeans and cut their hair short and wear shirts and boots and you think that's okay! You think it's okay for a girl to look like a boy."
"Yeah. And apparently you do too." She was wearing torn up jeans, a Black Sabbath tee shirt, and combat boots. Her blond hair was about six inches long and stuck out from her head at odd angles.
"That's not the point."
"Then what IS the point?" I knew what the point was. She had made me watch VELVET GOLDMINE again and I had opened my big mouth and made some stupid comment about Jonathan Rhys Meyers in a dress. The whole gay theme of that movie made me uncomfortable. I had unwanted doubts about my own claim to heterosexuality and didn't need a guy in a dress to make it worse.
"You think it's degrading for a boy to look like a girl."
"I didn't say that." Did I?"
"No, but you implied it. Guys think being a girl is degrading. Well, guys like you anyway. But I think you have a secret, Shaun. I think you'd like to know what it feels like for a girl."
I'd thought about it but I wasn't about to admit it. Especially not to Jess. "That's ridiculous, Jess."
"Then you won't mind making a bet with me, will you?"
Of course not. Jessica had never won a bet. Ever. "What kind of bet?"
"Classes end this week. Next week is the first week of summer vacation. At the end of the week whoever has the highest GPA wins. If I win, you have to be a girl for a week."
"What? Jess, that's-"
"And if you win, I'll be your slave for a whole week."
Well, my apartment COULD use a good cleaning. "Sure," I told her. My grades were ALWAYS better than Jessica's.
A week later when I showed up at Jessica's apartment I was already planning what I would make her do. My GPA was 3.9. There was no way Jess could beat that unless she had a 4.0, which would mean her grade in every class was perfect. Considering Jessica's commitment -- or lack of -- to school, that was highly doubtful. But even the most doubtful of things occasionally can -- and will -- happen.
I had agreed to the bet and couldn't back out of it. But at the same time I couldn't help but wonder if this was going to be Jessica's revenge on me for all of the times I'd won and all of the degrading things I'd made her do.
At 7:00 on Saturday night I went to Jessica's apartment, everything I would need for the next week packed into my backpack. She had decided that we would start Sunday by going to the mall. Therefore, my torture began on Saturday.
The first thing she insisted on doing was showing me exactly how much pain girls went through to wax their legs. Although she wouldn't admit it, I KNOW she had to have done something to make it more painful for me. But when I complained all she said was, "Now you know what it feels like for a girl." Then she added, "But the next thing we're going to do will be good."
YEAH, I thought, IN YOUR OPINION. But I didn't say anything. If a girl could take this, so could I.
But as it turned out, the rest of what Jess had planned wasn't so painful. "Sit there until I'm ready," she said, pointing to her bed. Then she went into the bathroom. I heard her moving around, opening the cabinet under the sink, then the towel cabinet. I guessed that I was probably going to be taking a bath and was proven right when I heard her running water in the huge, old, claw footed bathtub. A few minutes later Jess shouted, "Shaun!
I came, although I would rather have turned around and went in the other direction. "What?"
She pointed. "Bath time."
I didn't complain and this time it wasn't because I could do anything a girl could. After what I had just went through, a bath would be good, even with the kiwi scented bubbles floating on top of the water. Without giving Jess time to leave, I stripped my clothes off. I didn't have anything that she hadn't already seen a thousand times anyway. Letting my clothes fall on the floor, I stepped into the water. It was hot but not so hot I couldn't stand
it and whatever concoction Jess had dumped in the water smelled wonderful. Yes, even guys -- STRAIGHT guys -- can appreciate something that smelled fabulous. I leaned back against the back of the tub and closed my eyes. They were still closed when Jess picked up the clothes I had just discarded and left the room with them. I had, however, opened my eyes when she came back with a pair of pajamas, recognizably her pajamas, and laid them on the counter by the sink.
"What the hell is that?" I asked her. I already had a pretty good idea. Jessica and I are very close to the same size. I had to be a girl for a week. That meant I had to get clothes from somewhere. That somewhere was going to be Jessica's closet. Fucking great.
"Pajamas. You need something to sleep in, don't you?"
"They're pink." I was NOT wearing PINK.
"Girls wear pink."
"I'm not a girl."
"For the next week, you are."
What the hell? It wasn't like anyone was going to see me wearing them. Besides, I was enjoying the bath too much to ruin it by arguing with Jess. LET HER HAVE HER MOMENT I thought. But I was well aware that a supposedly heterosexual male -- like myself -- should have put up more of a fight about wearing pink silk pajamas.
I didn't have much time to torture myself over it because she opened a box I had only just noticed, mixed the contents of a tube and bottle then sat down on the edge of the bathtub behind me, her legs submerged in the water up to her knees. I wondered what she had in store for me now but didn't have time to ask.
"This," Jess said, "is hair dye." Meaning the little bottle of foul smelling liquid.
"Why? If I don't do something to you, everyone you meet will be able to tell that you're... Well, that you're you dressed in my clothes. You don't want that, do you?"
She had a good point. I DID NOT need to get caught cross-dressing. "Fine."
I was then subjected to nearly an hour of that detestable smell while Jess turned my naturally blond hair black.
"All right," she said finally. "I think we're done." Jess got up, dried her legs, and said, "When you get dressed, come in and help me pull the bed out." I would be sleeping on her couch, which folded out into a bed.
"Yeah, whatever," I told her. Jess left. I got out and dried off. Then I looked at the pajamas again. I didn't want to put them on but if I was going to have to wear Jessica's clothes 24/7 this week...well, best to get used to it while it was just me and Jess. I put them on and was amazed. They were silky and so...soft, not at all what I thought they would be like. And I didn't want to admit it, especially not to Jess, but it felt good.
Falling asleep that night was a chore. I was terrified of what the following week would bring, afraid that, somehow or other, Jess would discover my attraction to members of the same sex, something I hadn't fully admitted to myself until recently. It was almost dawn when I fell asleep.
On Sunday morning Jess shook me awake long before I was ready. "Oh, good," she said when I opened my eyes. "Breakfast is in the kitchen. I've laid out clothes for you on my bed. But eat first. Then we'll do your make up and then you can get dressed."
"God, Jess." I rubbed my eyes. "What time is it?"
"9:30. Time for you to be awake."
Like hell it was. When I didn't have class I slept until noon or after. But I got up.
Jessica's idea of making breakfast was to sit a bowl, spoon, and box of cereal on the table. I didn't care. I ate and was dragged off to the bedroom for make up.
"Be very still," Jessica said. She picked up and eyeliner pencil. After the eyeliner came light purple eye shadow. Then she picked up some kind of pink sparkly stuff in a round, flat container.
"Candy flavored lip gloss."
"Oh." I waited until she had put it on me and turned her back. Then I licked my lips. They tasted sugary sweet, like candy. I got dressed without protesting -- lavender t-shirt and faded jeans with holes in the knees.
"Now," Jess said when I was dressed, "don't you look like a girl?" She opened the closet so I could look in the mirror on the door. "Well?"
I looked in the mirror and a hot girl looked back at me. Completely flat-chested but hot just the same. "That's me?"
"Yup." She sounded proud.
"Wow," I said, amazed.
"Come on, Shauna. Let's go to the mall."
"Well, I obviously can't call you Shaun when you look like that."
It was noon when we got to the mall so we went to the food court first. As we were standing in line at THE PIZZA PLACE I heard someone call, "Jess!"
Jessica turned around and I saw her smile. "Hey, Robby," she said.
I turned to look. The first thought I had when I saw him was OH, GOD HE'S HOT.
The Thought terrified me but it was the truth. He was beautiful, about 6' tall, long light brown hair, beautiful blue-green eyes. He wore a black Skid Row tee shirt and tight black leather pants that looked painted on. If I ever had any doubts about liking guys, they were gone. I still thought girls were hot too but I was instantly in lust over this guy
and it scared the hell out of me.
"Robby, I'd like you to meet my cousin Shauna," Jess said. "Shauna, this is Robby from my American Literature class."
"Nice to meet you," I told him.
He smiled and the attraction grew stronger. "My pleasure," he murmured. His voice was not unlike the purr of a cat -- a large DANGEROUS cat -- and so incredibly sexy. The guy -- Robby -- got in line with us and said, "I think I'll buy lunch today."
"Shauna and I are going shopping after lunch."
"Why don't you come with us?"
No! God, no! I wanted him. To the average straight guy, meaning me although apparently I was NOT so straight, that was a scary thought. I wanted him gone.
"Sure. I'd love to."
"But on one condition."
Oh, good. Maybe he would go away after all.
"What condition?" Jess asked.
He smiled. At me. "I'll go with you but only if Shauna goes out with me tomorrow night."
No fucking way. I opened my mouth to tell him this but Jess cut me off.
"Of course she will, won't you, Shauna?"
Oh, how I hated her. I didn't like the whole idea of this bet but going out with another guy? Was she insane? "Fine," I told her, surprising myself.
But despite any thoughts to the contrary, I really did want to go.
And the rest of the day? It was HELL! Robby hung around until 7:00pm. I must have stared at him the whole time.
"I hate you, Jess," I said when we got back to her apartment.
"No, you don't. You love me." She seemed totally unconcerned, probably because she knew she was right. "But look on the bright side, darling."
I hated it when she called me that.
"Now you know what it feels like for a girl."
Jess insisted on helping me get ready for what she called The Big Date. To tell the truth, I think I could have done better without her. It was nearly the same ritual as Saturday night, without the hair dye, of course. It was also nearly the same fight.
"I am NOT wearing that, Jess," I told her when she showed me what she thought I should wear.
"Oh, come on, Shaun. You'll look wonderful in it."
I didn't care. She wanted me to wear a dress and that was pushing it too far. "No."
"No way." I could hold out indefinitely as long as she didn't use the puppy dog eyes.
"Shaun..." Puppy dog eyes.
"Oh, all right. I'll put it on but if I don't like it, it comes off."
Jess smiled and left, leaving me to get into the offensive thing on my own. I picked it up and looked at it. It wasn't that ugly. On a girl maybe. It was black with three-inch wide straps to hold it up and fastened in the back with a row of round black buttons going from waist to neck. When I had it on, it came to a little above my knees. Jess, when she came back with a pair of shoes, buttoned up the back. It was tight but not unbearably tight.
I started for the closet to look in the mirror but Jess said, "Hold on. Shoes first." I sat down on her bed and put on the shoes she handed me, black patent leather Mary Janes with three inch soles. They made me taller, which was good. I had felt SO short when standing next to Robby in the mall. 5' 6" was nothing compared to 6' 2".
The door bell rang moments after I had put the shoes on and Jess all but forced me into the living room, not giving me a chance to decided if I wanted to wear a dress or not. I was wearing it regardless.
"Sit down," Jess said. When I was sitting, she opened the door.
My first thoughts when I saw Robby were similar to the last time, even though he was dressed differently now. He wore leather pants again, which Jess had explained was his usual attire, and a black fishnet shirt with a black t-shirt over it and the same combat boots he had worn the day before.
We went out for dinner, some French restaurant that, while not expensive, was not exactly on a fast food level. Everything in the restaurant was written in French, from the menus to the business hours. I didn't know a word of French but Robby spoke it fluently.
After dinner we went to a movie, completely English this time. And completely boring. Fortunately, or unfortunately depending on how you looked at it, Robby noticed and said, "Do you want to go back to my apartment? I have more interesting movies there."
Once again my big mouth decided to function without my brain's permission and I said yes. Immediately after I wondered why. I was so STUPID. I knew why Robby wanted to go back to his apartment. The movie was just an excuse. I had used the same excuse -- or one like it -- many times to get girls back to my own apartment. If Robby tried anything, he was going to have a big surprise.
But I had underestimated Robby. He wasn't like that at all. When we went back to his apartment we watched QUEEN OF THE DAMNED. As we were sitting on his couch in front of the television I felt his arm come around. I tensed up at first but when he left it there and didn't do anything further I let myself relax against him.
And to my surprise it felt good to relax against Robby and let him hold me. I hadn't been held like this for a long time. I was so tired and Robby was warm. And I fell asleep.
I woke up what must have been hours later when Robby moved. "Shh," he whispered. "It's okay. Go back to sleep." I curled up against him again and closed my eyes, not really awake enough to realize what I was doing. Before I fell asleep again I SWEAR I heard him call me Shaun.
Jess was waiting when I got back to her apartment around noon the next day. "Well," she asked when I came in. "What happened?"
"We went to a French restaurant and then to a movie, which was really boring so we went back to his apartment and watched QUEEN OF THE DAMNED. I fell asleep and we went to McDonalds for lunch then came back here."You slept with him?"
Why had I told her that? "Yes."
"That IS all you did, right?"
"I think if anything else had happened Robby would have had a big surprise." I wasn't about to tell her he had kissed me, much less that I had liked it.
"I suppose so."
I went into her bedroom to get out of that horrible dress and fond that she had already laid out clothes for me to put on. Thank God it was just jeans and a tee shirt. I wasn't sure how many more dresses I could take.
"You're going out with him again though, aren't you?"
Yes. Definitely. But I had to tread carefully so Jess wouldn't know how much I liked Robby. She was too damn perceptive. "Maybe."
"Tomorrow night." Tomorrow was Wednesday. I had three days, counting Wednesday, until this stupid bet would be over. But there was also a downside to that. I had three days to be with Robby. I was pretty sure he wouldn't take it well if I suddenly said I was Shaun, not Shauna.
"Oh, good. I get to dress you again."
"I am not wearing a dress again."
"Where are you going?"
"The aquarium and out to eat."
"Oh. I suppose you could wear jeans then." She was silent, something rare for Jess. Then she said, "Hey! I thought you hated the aquarium."
I did. But I liked Robby. So, unable to think of a suitable reply, I just shrugged.
Jess smiled but didn't say anything.
When Wednesday night came I was looking forward to seeing Robby instead of dreading it like I had Monday night. Part of that could have been contributed to wearing jeans, a Rolling Stones tee shirt, and flip-flops, which was more like something I would normally wear. The only difference was the make-up and that the jeans were Jessica's.
Robby, when he got there, was wearing leather pants (big surprise) but they looked like red snakeskin this time. With them he wore a long sleeved black shirt that said CLASS OF 2001 on the front and had the signatures of his senior class on the back. And of course the usual boots.
We went to the aquarium, a rather boring place without Robby. I was paying more attention to him than to the fish and liked the feel of my hand in his and the occasional kiss when no one was looking better than the octopus and seahorse.
After the aquarium we ended up at McDonalds again. It ended all too soon. I would have been happy to prolong that night for eternity. But all things must come to an end.
Jess was waiting for me when I got back to her apartment. "Well?" she asked.
"You are a sadistic bitch," I told her, sitting next to her on the couch. "But I love you anyway." That was NOT what I had started to say.
Or the response I had anticipated.
"Now, care to explain that?"
Absolutely not. If I explained that statement to Jess I would have to admit that I liked Robby. Jess would have a field day with that.
"Can't or won't?"
"Because I can't." Great answer.
"You like him, don't you?"
"You know who."
I did. She was talking about Robby. "No I don't."
"Robby, you idiot. You like him, don't you?"
"Of course. What's wrong with that? You like him too."
"I mean as more than a friend."
"I..." What was I supposed to say to that? And how had she guessed? "How..."
"I've known for a while, Shaun. Not that you like Robby of course but that you're bisexual."
I cringed. I DID NOT like that word applied to me. But that was what I was. "Oh, fuck."
I just shook my head. I had suspected that I might like guys for a while and I had known for sure when I first met Robby but I had never applied a word to it.
"Shaun? Hey, are you okay?"
I nodded, but no, I wasn't okay. I hadn't cried in forever and now I was fighting back tears.
"Shaun? Come on. You're scaring me." I could hear Jess but she sounded so far away. "Shaun!" I didn't see her hand move but I felt her slap me.
"God, Jess! What was that for?"
"That's better. You were freaking out."
"I was?" I touched my face where she had slapped me. It fucking hurt!
"Yes, Shaun." She sighed. "I'm sorry I said that. I don't think you were ready for it."
Jess was apologizing? That was something few people ever heard. "It's okay. You were right. I am." It felt good to say that. I was so relieved that I didn't have to worry about Jess figuring it out on her own anymore. She already had.
"Are you all right now?" Jess reached up to touch my face. When her hand came away wet I realized I was crying. It seemed this was the night for rare things. "What's wrong, Shaun?"
"I want Robby," I told her.
"You want me to call him and see if he'll come over?" She reached for the phone.
"No." I grabbed her hand. "I mean I want him when this whole stupid bet is over."
"You'll have him, Shaun. I promise."
"How? What am I supposed to do? Walk up to him and say, 'hey I'm that girl you've been going out with but I'm really a...bisexual guy dressed in my best friend's clothing?"
"You won't have to. He already knows."
"WHAT?" To say I was shocked would be a gross understatement.
"I'm so sorry, Shaun. I didn't think- No. Maybe I'd better start at the beginning." She handed me several tissues from the box beside the couch. "Robby and I have several classes together. For one of them we had to do a project. And he came over here. When we took a break he was looking at your senior picture and he said he thought you were hot. I was pretty sure that you liked guys so I came up with the bet and talked him into going along with it. Robby was against it from the start."
"Fuck, Jess. Why?" I was really crying now. She had been my best friend, closer than a sister, since preschool. How could she do something like this? And why would she?
"I don't know. I guess I thought it was a good idea at the time. I didn't know it would go this far, that it would hurt you so much."
I had to get out of there before I really broke down. "I'll see you later, Jess," I said. Then I left.
I walked for a long time, a couple of hours at least. I wanted to go home. Not home to my apartment but home to where my mom and dad were. But that was so far away. And without my keys, which were in my backpack at Jessica's and I was NOT going back there, I couldn't even go back to apartment. So I walked and finally ended up sitting down on one of the swings in the park. I shivered. It might be May, almost June, but it was cold and rain, the rain that had completely soaked me, made the cold worse. I'd get out of it if I could but without my keys I didn't go home or back to my apartment. And I wasn't going back to Jess's apartment long enough to get my keys.
I wiped my face with my sleeve again, ridding it of the water and tears. Gravel crunched under foot on the playground behind me, heading my way. "Go away," I murmured, thinking Jess had come to find me.
"I can't do that." It was Robby. "If I leave you here you're going to catch pneumonia."
"Shaun. Come on."
I turned to look at him as he wrapped his leather jacket around me.
"It's okay. I know all about it. Jess told you, didn't she?"
I nodded, not trusting myself enough to speak.
"Let's go then." Robby held out his hand. I reached out and placed my hand in his. His fingers were warm when they closed around mine. I let him lead me to the car.
It was only when he pulled out of the parking lot and turned away from Jess's apartment that I relaxed. "Where are we going?"
"Back to my place. Unless want me to take you back to Jess."
"No." That was the last place I wanted to go.
When we got to Robby's apartment he found a t-shirt and a pair of pajama pants I could wear, although both were slightly too big. I dried off, left Jess's wet clothes in the bathtub, and put on dry clothes. Then I got into bed beside Robby. As I drifted off to sleep in his arms I knew that eventually I would forgive Jess. I always did. And one day far in the future Jess and I would look back on this and laugh at how Robby and I got together. But it would take a long time to get to that point.