Being Tiffany

Heidi K.

  

It started off like any other Saturday. It was a beautiful spring morning, my parents had already left the house to go bargain hunting and I was on the phone with Jody, one of my best friends. She had called to ask a huge favor from me since she was alone for the day. I told her no problem and left for her place wondering what the favor was. I found her waiting for me at the door. She led me into the living room and then explained what she needed.

 

"Tim, first you have to promise to hear me out and not say no right away."

I agreed to listen but now my guard was up.

"As you know, I'm making my own prom dress and it's almost done but I need someone to wear it while I mark the hem line."

"Oh no! Not me! I am not wearing it! Find somebody else," I quickly answered.

She reminded me that I had promised to listen to her so I sat on the couch but I wasn't changing my mind.

"I want to have it finished today and you know, my mom's at work and Teresa is at the mall. I tried calling everyone else but they were either busy or had gone out already. I don't think you know how to hem a dress, so the only solution left is for you to put it on only long enough for me to pin it. Nobody will see you and no one else but us will know. Now what do say? Come on I'm desperate here!"

I thought about it for a little while with Jody's pleading eyes staring at me and then reluctantly announced I would help her.

"Oh thank you," she squealed, and pulled me upstairs to her bedroom. She opened the closet and handed me the red gown then told me she would be waiting for me in the living room as soon as I had stripped off my shorts and t-shirt and slipped into it.

I started to protest but she explained I couldn't wear my clothes under it because it wouldn't hang right so once again she won out. With her returning downstairs I began to strip, regretting ever agreeing to help her. After stepping into the gown, pulling it up and sliding my arms through the short puffy sleeves, I found I could only zip it up part way. It was so long I had to pull it up to walk safely down the steps to the awaiting Jody.

I explained how I couldn't do it up right and she smiled and stepped behind me to finish zipping it up and then tied the sash into a large bow at the back. I was told to stand on the coffee table where she walked around me commenting to herself then left me there alone. She returned with a pair of red satin 2.5inch heeled sling back pumps. I took one look at them and immediately expressed my refusal.

"That wasn't part of the deal", I explained, "You never mentioned you wanted me to wear those."

"But I need you to wear them so I can get the right height for the hem. Come on, you're already in a dress, they're just shoes, they won't bite," she quipped.

Once again I succumbed to her thinking, slid into the shoes and she fastened the straps for me. I found them to be a little tight since I had kept my socks on. I couldn't wait for this whole ordeal to end. She walked around the table once more then began to pin the gown. That's when the situation turned even worse. Teresa had come home early from the mall. She burst into a fit of laughter at the sight before her eyes. I wanted to run and hide but Jody grabbed my arm and reminded me fleeing was futile since I couldn't get out of the dress by myself anyways. So instead I had to remain standing there while Jody painstakingly returned to pinning. While still laughing, Teresa slipped off upstairs.

 

Jody was not quite finished when Teresa returned with a video camera.

"This is too good to miss, I always thought red was your color".

"Oh come on sis, he was good enough to give me a hand, turn off the camera," Jody chimed in my defense.

"Not a chance, he looks too cute in his pretty gown."

As Jody finished her work, I pled with Teresa not to mention this to anyone. Since we both knew I was in no position to barter, an agreement was quickly arrived at. She would keep this and the tape of me in the gown to herself but in exchange I would be at her mercy until Cheryl came home from work.

"It's a deal. Now help me out of this dress."

"Umm…one more thing," added Jody, "I will need you to put it back on after I sew it to make sure it is straight and looks right."

"No way. I wore it for you to pin it, Teresa's home now, she can check it while you wear it."

"Excuse me Tim, but I think you will wear it for Jody," corrected Teresa, "Jody get the sewing machine ready and I'll help Tim."

The two girls helped me off the table and Teresa led me upstairs to Jody's room.

"We are going to have so much fun today Tim. Relax and you might actually enjoy it, I know I will."

With the sash untied and the back unzipped, I stepped out of the dress and removed the shoes while Teresa plugged in a curling iron then ran the dress to Jody and returned promptly.

"Okay Tim, now the fun begins. Sit on the chair at the vanity and remove your socks."

While I removed them, she dug through Jody's drawers and produced a pair of pantyhose and told me to put them on. I started to tug and pull them up when she stopped me and showed me how to roll them up my legs. While I started again, she grabbed the camera to film me. Once that was complete I was instructed to stand up and Teresa produced one of Jody's bras and after I passed my arms through the straps, she fastened the back. A few more pairs of pantyhose were padded into each cup until I was close to the same size as Jody.

"Okay you can sit back down. Now, unfortunately we don't have much time before Jody will be finished so this will have to be quick."

She started with a little eye shadow, black eye liner and mascara, then added a little blush to my cheeks and finished off with bright red lipstick. Next she gathered up a few strands of hair and grabbed the curling iron forming a ringlet in front of my left ear. When she did the other side she got me to hold then release the iron while she filmed.

We heard Jody yell she was ready and Teresa called back she would be there in a minute. Before she left, she fastened the rest of my hair into a small tight bun and told me to put the shoes back on. She came back with the dress and filmed me stepping into it, putting my arms through the sleeves and doing the zipper up as far as I could get it then Teresa finished closing me in and we made our way downstairs. Jody was astonished when I walked into the living room and stepped up on the table once again.

"You look so pretty," she squealed, "Looks like you are already to go to the prom!"

"Not quite sis but I know what would help finish the look. Keep him there."

Teresa ran back upstairs and I stood on the table while Jody inspected her handiwork, smiling the entire time.

Teresa eventually returned with the camera and a red satin handbag with pretty lace handles Jody had made and passed it to me.

"There, now he is all dolled up and ready. Smile Tim like you're enjoying it," snickered Teresa while filming me standing there and holding the girlie bag.

 

Once again I was helped off the table and led upstairs while Teresa filmed me walking, carrying the satin bag. I couldn't wait to get out of the gown and get changed.

"I see you noticed your clothes aren't there anymore," added Teresa when she saw me glance over at the bed. "Remember our deal, you're mine for the day. Right now you have two choices, you can continue to wear the gown or you can change into something a little more comfortable."

That was an easy decision, I just wanted out of the prom dress. After telling her my decision she gladly helped me out of it, hung it up and returned from the closet with what was to be my new outfit. I pulled the short black spandex skirt up and donned the red top, while Teresa filmed and Jody giggled. The top had long sleeves with the cuffs and neck trimmed in marabou feathers. To finish off the look Jody provided a pair of 3 inch black patent pumps.

"Now I have time to finish what I started. Jody, you polish his nails and I'll do his hair."

While doing my hair, Teresa got a little more footage consisting of me painting one of my now bright red nails and holding the curling iron again. Once the girls had finished, Teresa went off to her mother's room and brought back a pair of old clip-on earrings. They consisted of five small black stones that dangled straight down from my ears.

"Wow! Look at him Teresa," exclaimed Jody, "It's hard to tell he's not really a girl."

Unfortunately I had to agree as I looked in the mirror and a pretty girl stared back at me.

"Okay Tim, you can get up now so I can film you walking around."

The girls stood beside each other coaching me while I walked. After that I was taught how to sit properly and then instructed to strike various poses.

"You know Teresa, he's far too pretty to be called Tim. What do you think?"

"I couldn't agree more. In fact I kinda think he looks like a Tiffany."

"Tiffany!! Teresa, that's perfect. How do you like your new name Tim, I mean, Tiffany?"

I didn't say anything at first but Teresa had me say to the camera, "Hi my name is Tiffany. Do you think I'm pretty?" which caused the girls to break into a fit of laughter.

"Hey Jody, we've got another hour before we have to change Tiffany back, what do you say we have a light lunch and some lemonade out back?" asked Teresa.

"Sounds like a great idea sis, I'll start making the lemonade."

I immediately voiced my disapproval even though a privacy fence enclosed the yard. But again Teresa brought up the deal so I was helpless. Lunch was a small fruit salad as none of us were that hungry and Jody handed me my drink with a straw in it so I wouldn't leave lipstick marks on the glass. The girls chatted and complimented me on how good I looked but I ate and drank in silence waiting for time to hurry up.

"Okay Jody, I think poor Tiffany has had enough and she's been such a good girl all day, it's time she changes back to Tim. You clear the table and I'll help her, that is if she wants to change back."

"Of course I want to change back," I said trying not to be too loud and jumped up from the table and moved just a little too quickly in the heels and wobbled slightly.

"Slow down girl," laughed Teresa, "We wouldn't want you to fall and break a nail or even worse, a heel!"

 

Teresa filmed me while I stepped out of the heels, undressed down to my undies and bra then finally put the camera down for the last time. My hair was straightened back to my boy style while I removed the nail polish. Make-up was removed then she undid the bra and fetched my clothes. I was back to Tim with only 10 minutes to go before Cheryl arrived from work. I headed for home after making them promise again not to tell anyone of what I went through. I had a hard time getting to sleep that night as my mind kept replaying everything that happened that day. The rest of the week went on as usual with nothing being said about Saturday's events.

 

"Tim, phone call for you, I think it's Jody," I heard my mom yell the following Saturday morning. I crawled out of bed and stumbled down the hall to the phone. It was in fact Jody and she wanted me to come over to her place as soon as possible because she had something she wanted to show me. I told her I'd be over shortly. After showering and dressing I told my mom where I was going and headed down the street. Teresa answered the door and ushered me into the living room where Jody was already seated.

"Ok Jody, go ahead and show him now"

Jody smiled while she turned on the TV and VCR. On the screen was some of the footage Teresa shot the previous week but all dialogue was dubbed over with music except the part where I say my new name and asked if I was pretty. It started with me rolling the pantyhose up, and then curling my hair while wearing a bra and make-up after which I was in heels putting on a prom gown. Next came the part of me walking through the house carrying the satin handbag then I was changing into a skirt and girlie top, painting my nails and walking and posing for the camera. It looked like I had done it all on my own accord.

"So, what did you think," asked Teresa. "We thought it turned out very well and yes, we both thought you were pretty," giggled Jody.

I sat in silence taking it all in. If anyone saw this, I would never live it down.

"Remember your promises," I stammered, "No one is to see this."

"Oh but Tim," Teresa interjected, "the deal was I would keep the tape of you in the gown to myself, but nothing about you in a skirt and heels."

"She's right you know," added Jody, "we talked about it and came up with a new deal. You will be Tiffany again for today in exchange for the tape. We did not make any copies. If you choose not to become her or fail to do as we ask then our classmates see the tape. So, is it a deal?"

What could I do? I couldn't let anyone see it. I had no choice so I agreed to become Tiffany again.

"I can't wait to get started," squealed Jody, "Teresa has your outfit all ready to go."

 

I trudged upstairs wondering what they had planned for me today. Upon reaching Jody's bedroom Teresa handed me a pair of pink panties and matching bra with pantyhose for stuffing. Along with that she gave me a straight black skirt and pink peasant top and told me to change in the bathroom. I stripped off all my boy clothes and slowly changed into the outfit I was given. I struggled with the bra for a while until I decided to do it up in front, spin it around and then put my arms through the straps then inserted and adjusted the pantyhose. After zipping up the skirt and donning the top, I made my way back to Jody's room. I hated to admit it but I kind of liked the feel of the panties. I entered the room and found both had changed and were waiting for me. Teresa also sported a skirt but hers was white and she chose a red top and wore white high heels. Jody was wearing capri style jeans also with a pink top but it had a large white daisy on the front and on her feet were bright blue low-heeled slides. Altogether it looked rather cute. For a brief moment I wished I were wearing that outfit instead.

"Oh good, you're done. Sit down and we'll do your hair and make-up. Jody you can do his nails, both fingers and toes this time. Here, use this shade of pink, it'll match the lip gloss Tiffany will be wearing."

The girls worked their magic and once again a pretty girl stared back at me in the mirror.

Jody left the room and returned a short time later with the same clip-on dangling earrings I wore last time and a pair of black mules with a 2.5inch block heel.

"I chose these so you can show off your pretty painted toes Tiffany."

The earrings were clipped into place and I slid my feet into the mules, which I found to be more comfortable than the pumps I sported a week ago. Teresa slipped away and returned with her black leather tote bag. From it she produced her perfume, which was dabbed on my neck and wrists, then she scooped up all the make-up they had used and placed it into the bag.

"There now you smell as pretty as you look and you can carry this since it doesn't match my outfit," said Teresa as I was handed the shoulder bag. "Everybody ready now? Let's get going."

"What do you mean lets get going? What have you got planned?"

"Why the mall of course Tiffany," added Jody, "We didn't go to all this work for nothing."

"NO WAY! I am not going to be seen in the mall like this. This whole thing was to be kept secret."

"Ah, but you see Tiffany," explained Teresa, "You misunderstood. The deal for today was you would do as we ask in exchange for the tape. The deal for last week included secrecy, not this week."

"You know she's right, so if you don't come to the mall, the class sees you changing yourself into a pretty girl. I'm sure the other boys would understand and the girls wouldn't tease you too much." "Oh I'm sure they'd understand Jody. Hey, maybe even one of them would ask Tiffany to the prom," Teresa quipped then turned to face me, "Come on Tiff, no one is going to recognize you and we won't do anything to single you out, we promise."

Once again I had been had so I did the only thing I could do, I slung the tote on my shoulder and made my way to Teresa's car.

 

We walked around the mall for what seemed like hours, looking at various women's fashions and accessories. The girls chatted away about usual girl talk but I stayed pretty much silent waiting for someone to point out the boy masquerading as a girl but it never happened. Instead I began to smile and enjoy walking around in heels. I found the noise my shoes made intoxicating as they impacted the hard floors then slapped my heel as each foot lifted. I couldn't believe it. I was actually enjoying being Tiffany. Eventually the shopping machines decided it was time to take a break and sit down for a while. We ended up at the food court and I held the seats while the girls ordered and returned with fries and drinks. They continued to chat about different articles they had looked at in the stores and to the delight of the others, I found myself chiming in the odd opinion now and then. With everything finished, Jody had dug out her lipstick and compact to freshen up her look and I passed the tote to Teresa so she could do the same. While stuffing her tools back into her purse she announced she would like to try on one of the pairs of sandals again. Teresa nodded in agreement, replaced her stuff and the tote was given back to me. Then I went for it, I dug through the tote, produced the lip-gloss and Teresa's compact and redid mine almost as expertly as they had while the girls looked in astonishment. For some unknown reason I could feel a small amount of pride well up in me after completing the feat.

"I thought it would look more natural if I did mine as well, you know, I don't want to stick out right?" I stammered hoping they would accept it as a good reason for my surprising act.

"Yeah, makes sense I guess. We better hurry if you want to try those shoes on Jody," added Teresa as she gathered up the garbage and deposited it into the can.

We went back to one of the many shoe stores and Jody tried on the sandals and hummed and hawed about which of the six colors she liked best with us putting our two cents in when all of a sudden Teresa gasped.

"Oh my God we're late! We have to go now!"

Suddenly we were all very much aware of the time, Jody removed the slides and replaced them with her own shoes and we practically ran from the store leaving a very bewildered clerk to pick up the remains. We dashed to the car and Teresa raced through town and pulled into the driveway in an almost screeching halt.

 

It didn't matter though as Cheryl's car was already there.

"What do we do now? I can't be seen like this."

"Relax, maybe we can sneak you in and get you changed. We might be lucky and she might be napping in her room or out in the backyard. Jody and I will go in first and if it looks clear, follow."

It wasn't much of a plan, but it was all we had. The girls entered the house, took a quick look around then motioned for me to go in. We made it to the stairs when Cheryl called to us to halt right there and get in the living room. She was seated quietly in the corner of the room out of sight and in her hand was the videotape. I stood there frozen in my tracks shaking. I was about to be seen by my friend's mother all decked out like one of the girls and almost in tears. It took both girls to grab my arms and drag me towards the room and guide me over to the couch where without even thinking, I smoothed my skirt as I sat under Cheryl's watching eyes.

"You three have some explaining to do. I have already viewed the tape but now I would like to hear your side of this quaint little tale."

Jody explained everything from the beginning right up through today's events while Teresa and I agreed along with her.

"I see, now Tim, or Tiffany, if I may call you that, any thoughts of your own about this?"

"Well, I have to admit I was extremely uncomfortable about the whole thing until at sometime during the mall trip I began to like wearing heels and talking girl stuff. You haven't told my parents yet have you?"

"No dear. I thought I would get the whole story first. So if I understand correctly, you now enjoy dressing and acting like a girl?"

"Yes ma'am, its kind of fun being Tiffany" I stammered.

"Well although I find this a little shocking, Tiffany is welcome here any time she wishes to show herself. I still have a few items yet to mention. Number one; here's the video tape, I believe you kept your end of the bargain."

As I reached out for the tape she continued the list.

"Number two; the next time you girls wish to borrow any of my things, like those earrings, ask first. Number three; in answer to your question, yes, I do think you are pretty. Lastly, I promised Jody and Teresa I would take them out for dinner and a movie and you are welcome to come along under two conditions. The first one being your parents allow it the second being you wear the outfit you wore on tape. I think you looked really cute in the red top," a smile broke over her face as she stated the last condition.

I jumped up and practically ran to the phone and got the approval I wanted, without of course mentioning anything about being Tiffany.

"My parents agreed to let me go, but can I wear these shoes instead of the stockings and pumps. I find these more comfortable and can I borrow these earrings Cheryl?"

With Cheryl's approval the three of us made our way upstairs so I could change my clothes and make-up.

 

That night Jody offered the use of her clothing whenever I wanted. It was an offer I took her up on many, many times.

  

  

  

*********************************************
© 2003 by Heidi K. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.