The Ballad of Tiffany Renee

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A young crossdresser's first time out and the fun she has.
1.4k words
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Chapter 1

I have always loved pretty things, for as far back as I can remember. Silky, soft clothing on a woman looks so beautiful, and feels so good. Even as a child, I loved the feel of satin, silk, and nylon brushing across my skin.

One of my earliest memories was of an Aunt of mine putting a pair of pantyhose on me and telling me to go show my mom how pretty I was. I loved the feeling of the nylon on my legs, and instantly fell in love with feeling pretty. I showed my mom, and she did say that I was pretty, but that was just humoring a three year old. I was hooked on the experience!

For years, off and on, I would get a pair of my mom's hose and wear them. It wasn't until I was nine or ten that I discovered the thrill of wearing panties and dresses, as well. Bras, heels, and makeup came later, adding to the experience. It finally got to the point that I wanted to be dressed as a girl, and be accepted as a pretty girl, but I was scared to death of being caught. I wanted to be treated like a pretty girl, more so than anything else in the world.

The summer of my eighteenth year, I decided to change the situation: I was going to go out as a pretty girl. Tiffany Renee was born!

I got my courage up, and planned a trip to the local theater to catch a movie. I got everything I needed gathered up and waited for the right night to come.

The perfect night arrived. My little brother and sister were spending a few weeks out of town with relatives. My mom started working her night rotations, and Dad's job kept him out of town most of the week. Like I said, perfect!

Chapter 2

About three p.m. on a Friday afternoon, I took a long hot bath, shaving off all my body hair. After drying off and powdering my self, I sat on mom's bed in front of her vanity and painted my fingernails and toenails a deep, dark red.

Then, I got the clothes out. First came the panty girdle, which held everything tucked up inside of me, then my mom's 36 D cup black lacey bra. I next put on my dark, coffee colored pantyhose, then the black lacy panties (that matched the bra) over the hose. I'm sorry, but wearing my panties on the outside of my hose made me feel sexy, still does!

I was getting real excited now, but the panty girdle held everything in place, so I still had the smooth outline, and the appearance wasn't ruined. Next came the hip pads, stuffed between the hose and girdle, to help give me a girly shape. Now was the fun part. Like I said, I did prepare a bit before hand, so I got my bra padding ready. They were 4 heavy-duty water balloons, stuffing one balloon within another, creating a pair of double walled balloons. These I filled with warm water, tied them real well, and stuffed them within the bra. I now had my own titties!! Making sure they were level, I slipped into my mom's shortest black slip.

Now the real fun part. I got my sisters red mini-dress out with these little black polka dots, and slid it over my now feminized body. On her, it was baggy and knee length, but on me it hugged every curve and came to eight inches above my knees. It was short sleeved, and the neckline was ruffled and elastic, so i could wear it on or off shoulder. The skirt part was slightly pleated and had some flair to it. I fell in love with it the moment I saw it!

Next came the shoes. Lord, how I loved those things! An aunt of mine gave them to me to give to my mom, but I was a naughty girl and kept them for myself! They were red, with four inch spike heels, opened toed with straps that came up from around the back of the heels, wrapped around the ankle, and fastened with a little gold buckle. The perfect 'fuck me!' shoes! I had been practicing walking in them so I had that part down pat! The short skirt, high heels, and hip pads gave a killer swing to my walk!

I sat at the mirror and did my makeup, making sure to highlight the lashes, cheekbones, and then applying lipstick in the same shade as my nails. I got out the final piece of the puzzle: my mom's long wavy platinum wig! It came down to halfway down my back! Clip on hoop earrings, dangle bracelets, a silver necklace, and silver chain belt finished it off. Time to look in the mirror.

WOW!! I was hot! I looked just like a eighteen year old tease, but a hottie, nonetheless! After a few glasses of dad's wine to calm my nerves, I gathered up my red purse and out the front door I went!

Chapter 3

Gawd, I was so nervous! I planned on walking to the theater, which was about a half a mile away, so I left in plenty of time. I got a lot of honks, a few 'Hey babe's', and whistles on the way. I loved it! Then, I froze.

A cop car! He drove by, then pulled over and asked if I needed a ride. Cool! Even a cop noticed me as a girl! He asked where I was going, and I told him to the movies. He got out, came around to the other side and opened the passenger door and told me to hop in, he'd take me! Lordy, I was nervous, but elated at the same time! Thank goodness for the wine!

As he pulled away, he asked me my name. "Tiffany Renee" I told him. His was Kyle, and he asked me my age, where I went to school, and did I have a boyfriend.

"Well, hon, I'm eighteen, and my daddy doesn't let me date yet, so I don't have a boyfriend yet, but a lot of guys are interested!"

"I'll bet, " he replied, with a little gleam in his eyes. "but I don't blame your daddy, a fox like you, the guys would do anything to get into your panties!"

I blushed big time. I didn't expect this, a cop hitting on me. "Oh, I wouldn't let them, I'm a good girl! I do what ever my daddy tells me to."

"I'm sure you are," he replied with a wink. This was too much; this cop was actually flirting with me!

Since the movies weren't due to start for a while, we went ahead and continued his patrol. We chatted and laughed, and I was really getting into it, after all, a cute cop was hitting on me. He complemented me on my looks, my dress, and told me I was a very pretty girl. I could have melted right there, the very words I always wanted to hear.

"So, why are you out by yourself? I'm sure your daddy wouldn't approve his sweet thing walking outside late by herself."

"Mom and Dad are out of town for the weekend, so I got kinda bored at home all alone," I said with a wink. He looked a little uncomfortable for a second or so.

"Well, I hope your weekend gets better," he said as he reached over to pat my leg, as he had a few times before. This time, he left it there for a few minutes. Then I realized how much of my luscious thighs were showing.

You see, a dress that comes to eight inches above the knees when standing has a bad habit of riding up when seated in a car, and four inch heels don't help much, either. I had my ankles crossed and knees together and to one side, but that side was toward him. He couldn't see my panties, but it was close.

Finally, we got to the theater, and he reluctantly removed his hand, asking me what time the movie got out. After telling him, he got out, opened my door and took my hand and helped me out. After thanking him, I turned to the box office and suddenly felt a pinch. He pinched my rump! I turned and gave him a smile and a wink, which immediately turned him red and he bent at the wait a bit.

"I'll see you later," I said, as I strutted into the theater.

"You bet you sweet cheeks you will," I heard him say as he got back in the car and pulled off. And he was right, but I had some fun inside to take care of first!

To be continued...

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6 Comments
AnonymousAnonymousalmost 13 years ago
Awesome story!

This was an awesome story! I wished you would have continued the story, though. Keep writing!

livinnsinptwnlivinnsinptwnover 14 years ago
Exciting

I can't wait for the second part. This. Was a great beginning I'm actually flustered.

AnonymousAnonymousover 19 years ago
MORE!!

great beggining can't wait for more, please give us more

Flintstone54Flintstone54over 19 years ago
A CD Wonders ???

I was just wondering why you gave her such large breast??? A "B" or "C" cup is a lot less to attract xtra attention...MY neighbour was 18,'N she was a 38DDD,she said they were a pain in the back.Thats why when I told her I was a closet "CD','N asked her for help to come out 'N play some,she told me NOT too go too big.I usually wear an "A" cup ... BUT in cooler weather,I wear a "B" or "C" cup under sweatshirts & coats.I like too have something noticeable under my top.

Kary_MKary_Mover 19 years ago
Really nice

Really nice start to a good story line. Keep it up dear. Kary_M

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