Stephanie’s Chance - 1

Printer-friendly version


Audience Rating: 



Character Age: 

TG Elements: 

TG Themes: 

Other Keywords: 


Stephanie’s Chance

By JessicaC

My sister Elle wouldn’t let me go with her to her college for a long weekend last year as she did with my sister Haley. Last year she said it would never happen but it now looks like I might get a chance.

The holidays are rough for me at home, because I’m the only guy in our house. Dad divorced mom when I was a kid. When we lost the farm and we moved to town. He had become a traveling salesman and one time he traveled away and never came back. We have been limping along financially ever since. Mom is finally a registered nurse making a decent income but with my two sisters in college, I’ve already been told I’d have to wait until Elle is through at the university. Because as a counselor and therapist she will need at least a master’s degree it would mean I will need to wait at least three years to wait.

I heard the doorbell ring, but I’m upstairs so I didn’t go to get answer the door. I heard Mom say, “Hello, come on in. It is nice to see you again.” Shortly after that Mom called upstairs, “Steve come down and say hello to Brad, he’s home from college.” Brad Street hadn’t been home all summer and we hadn’t been close friends for two years. But we use to be very close and we did a lot together even though he was three years older than me. He knew even after we weren’t so close, I had trouble saying no to doing things with him.

“Hey Sprout, it’s good to see you,” he said as I made my way down the stairs. “I asked your Mom if I could take you to the Drive-in over at College Center.”

I barked back, “It’s not a date so you should have waited to ask me.”

Brad chuckles, “Well, it could be a date that would save me the price of a ticket though it would cost me the price of a nice meal. If I have a date, we could go with Jake and Kari. Jake said it is date night at the drive-in and the date gets in for a dollar.”

“No way, if it’s like their last date night the date has to wear a pink bracelet. I’m not going to be a boy wearing a… pink bracelet.”

I didn’t know Elle had come down the stairs behind me. “Hey Mom, would it be alright if we helped dress little brother so he didn’t look like a boy on his date?”

“No way, you fucking b***h!” I knew I was in trouble as soon as I exploded, but even I wouldn’t have guessed what came next.

“Hold on right there Steven John Hammond! You just won yourself a punishment that fits the crime, that is if Brad will still take you?” My mother said. “Elle, why don’t you see if Haley wants to go shopping with you two?”

“Mr. Street are you open to taking Stephanie to the drive-in tonight?” Brad waited to see if my mother was serious before saying, “Yes.”

“There is no way I am going to do that Mom!” I said actually stomping my foot down.

“Elle take Stephanie with you upstairs to the shower and show her which hair care products she’s to use. Your brother’s long hair will finally be appropriate. Then make sure she knows which hair product to use on her legs and arms and to make sure she washes her hands really well.”

Elle took a hold of my hand and when I resisted she whispered, “If I were you, I would come without any argument and hope mother changes her mind and is open to another punishment.” It was humbling to follow my sister up the stairs. But what she said made sense. I’m pretty sure when things cool down Mom will let me go as Steven.


My mother says, “Brad, I know you have a good sense of humor so I hope this will be okay; otherwise he’s grounded and going nowhere.” She paused to see Brad laugh again and say it will be fine. “Would you like to pick up your date around seven or seven-thirty?”

“Well actually, if we're going with Jake and Kari, we were going to stop and get something to eat. If it would be possible, I should pick him up by 5:00 p.m.”

“Please, remember for tonight, it’s Stephanie and ‘she’. I don’t want her embarrassed and made fun of. If she doesn’t go, he will be grounded through the holidays plus a week. We’ll even go the extra mile on our side to make her look presentable.”

Brad said, “I will appreciate that since I wouldn’t want to embarrass Jake and Kari.” Mom later told Elle, he left with a big smile on his face, thinking it would be funny.


Mom is soon upstairs checking on me. I’m in the shower and I had finished shampooing my hair. “Make sure you use your sisters’ shampoo and conditioner twice.” She pauses, waiting for me to confirm I would. Then she asks, “Have you taken care of your legs and arms yet?” She waits again, guessing the answer.

“No mother, I don’t want too. Please don’t make me do that,” my voice raised as I said it.

“If we’re going to have an argument you know who will win.” She pauses again, “I want you to call me or your sister when you’re finished to make sure everything is satisfactory, do you hear me?”

I pause before I resign to answer, “Yes, mother I understand.”

I knew my mother went and talked to my sisters but I couldn’t hear what they were talking about


Mother said, “Elle and Haley, I don’t want you to be too rough on your brother, but we are going through with this.”

“I want you to find some clothes for Stephanie to go shopping in, I’ll have some money for you to take her shopping. I hope it is enough to purchase an outfit that allows her to look like an attractive young woman. She’ll need some nice shoes. Brad is taking her out to eat with his friends Jess and Kari. You will need to go the extra mile to make Stephanie look like a real girl.” She said to Elle, ‘Once you had told me, he would have made a prettier girl, now prove it please.”

“Mom, we’ve got two outfits for her to choose from,” Haley says. “He’s going to need to wear a pair of my panties and a bra if she’s to look convincing just for shopping for clothes.”

Elle says, “Mom, I think I should call his girlfriend Staci and tell her what’s going on. If she learns it from someone else and she will, it would be bad news for Steven.”

Haley perks up, “Elle, I think she will see it as being cute. She’s already said with his hair he already looks the part sometimes, when she’s seen him from the back or side. She’s said before the next ‘crossover day’ she’s going to pout until he gives into his dressing the part.”

Mom left the room, “Let me go downstairs before you call. I approve but I don’t want him to see me as being any part of that. It will also allow the outfit to be used again if Staci wants.”


Elle called Staci, “Staci, I wanted to call you; Steve exploded today with his mouth and got himself in trouble. Yes, he’s going to be grounded for a while if he doesn’t cooperate with our Mom’s punishment for him.”

I didn’t know who she was talking to on the phone when I call from the bathroom and ask her to check my arms and legs.

Elle only told me, “You need to do a better job. Use the hair removal cream on your legs this time. I heard you raised your voice to Mom again. You are so close to getting in even more trouble. I recommend you go around the rest of the day like you’re walking on eggshells and not talk back.”

She handed me her robe that I’m to wear until after I am dry. “Don’t dry your hair completely; we’ll need to do something to it so you’re not recognizable.”

Elle stopped back at the bathroom after she was off the phone. “Stephanie, I know you’ve gotten into my clothes in the past. I haven’t ever told anyone; so please don’t give me a hard time. I won’t say anything unless you get difficult. Do we understand each other?”

“I can explain; I am not whatever you’re thinking,” I remarked.

She says, “I don’t want to hear anything or get into a discussion about it. I just want to know if you understand me and will cooperate.”

My room was closed as Elle called me into her room where she and Haley were waiting. Haley took me by my hand over to Elle’s bed, saying, “We have two outfits for you to choose from, along with a pair of Elle’s shoes.”

I looked and the shoes have a two-inch heel. “I can’t wear that I'm not used to heels.” I saw Elle’s eyebrow rise.

Haley said, “You are more likely to remember to walk with shorter steps like a girl if you’re wearing heels.”

I looked at both outfits and both were very nice if you’re a girl. One was too girly; I suspect they kind of picked out what I was to wear. When I saw the light green bra I wanted to scream but thought the better of it. Haley spoke up, “It looks like the little sister has resigned herself to what is going to happen.”

I said, “I am just cooperating in the hope this stops before I have to go to the drive-in tonight or else I’m staying home.”

Haley left the room and Elle turned her back telling me to put on the panties. Haley’s bra was something else and I appreciated Elle’s help in joining the hooks. “You know there is an easier way don’t you?” My sister used two matching pairs of footies in each bra cup to give my chest the desired look. The blouse was white linen with crocheted flowers on it. I noticed the green bra showed through noticeably. “Yes, it shows and no you are not changing, live with it.”

“Haley, you can come back in and help us now.” Haley had a package of pantyhose so I protested. “You two don’t always wear stockings, why should I have too?”

“You haven’t tanned your legs properly,” Haley commented. “Those white sticks you call legs to shout ‘boy’ out loud.” I let Haley show me how to roll the stocking portion and guide them up my legs. I had worn pantyhose before but with my smooth legs and no hair, it feels very different. Both sisters caught me smiling as I put them on. The skirt is a glimmering gold and gave little here and there as it snuggles my body. The short skirt along with the heels would remind me to take smaller steps. Without either sister telling me, I took a few steps and turned around to see how it felt.

“Come over here young lady and sit down; I’ll do your hair and our sister will do your makeup,” Elle said. Haley told me, “Watch how I do your makeup, you need to know in case you need to do a repair on your own. Remember if you need to go to the girls’ room, a girl usually checks her hair and freshens her lips and makeup, when she’s done.”

I was surprised how easily she covered up my blemishes with a little concealer. She didn’t use much of a foundation but it did do the job of evening out the tone of my skin. She did one part of my eyes and then outlined my lips to give my eye makeup time to dry. The blush made it look like I had higher cheekbones and a not so round of a face. She said, ‘You don’t need much mascara and your complexion is very good. You know your eyelashes should have been on a girl.

I said, “Don’t make it sound like I’m a girl because I’m not.”

“Don’t get defensive, we didn’t say you are.”

Elle had to tease me, “I don’t know, I think Steph’s a pretty girl in her own right. Mom should like her youngest daughter.”

“I’m not a girl, stop saying that.”

Elle told me to calm down, “Calm down or you will wreck your makeup by causing lines.”

Elle was already done with my hair as I had been concentrating on Haley doing my makeup. My hair looked gorgeous and made me look way too much like a girl. I said, “Where did those bangs come from? And you shaped my hair. What am I to do when Mom says I don’t need to go?”

Elle said, “After your date with your boyfriend your bangs can be cut and your hair can be restyled for Steve.” I look in the mirror again, only half hoping she is right. Right now, I enjoy seeing a pretty girl who had little resemblance to me. She definitely could have been one of my mom’s daughters. Elle spoke up saying, “As far as anyone else is concerned you’re a cousin on mom’s side of the family.”

“If Crystal had a younger sister, Steph could be that sister,” Haley chimed in saying. She hands me a purse with a shoulder strap. “Boys carrying a purse tend to look like they’re carrying a loaf of bread like a football.” They take me downstairs to show me to our mother. Mom thinks I look cute. I am hoping that would be enough, but it isn’t.

Elle asks me to speak with a girl’s voice. “Not so high or forced, speak softly and casually move your hands.” She has me introduce myself as Steph, as well as to respond as if I like a skirt or dress as well as ‘thank you’. They got me to the voice they liked and excuse us from Mom saying, “We were on our way to a mall.” I protested but both Mom and Elle warned me to stop.

The mall we were going to was far enough away yet not terribly far. There was a shopping center in between and two malls closer in other directions. They convinced me we were safe from being seen. I protest, “There are none far enough to suit me.”

Elle and Haley talk to me all the way there so I would continue to use the same feminine voice. When we got there Haley told me, “Don’t speak unless you really have too.”


We looked at several women’s stores before heading to JC Penney’s. I then heard a familiar voice, “Elle and Haley wait up; I thought that was you.” It’s my girlfriend Staci and I’m cringing as I continue to look away towards Penney’s. I felt a hand on my arm. “You might as well turn around; I heard you got yourself in trouble with your Mom.”

I close my eyes as I turned around like it would protect me somehow. “Wow, don’t you look especially nice for shopping. What are you looking for; I would be pleased to help.” Finally, I open my eyes to face the music of losing my girlfriend or being laughed at. “You know I’d be more upset when I learned about it from others. We’d have been through a lot. You are lucky Elle called me.”

“Yes, I’d like to put my hands around her neck and thank the life out of her.” I looked at Elle wishing my stare would do the job. My sister always seems to have the edge as she stared back with a smile and raised an eyebrow.

“She also knows you have to go out with your former boyfriend,” Elle simply states. I looked at Staci.

Staci says, “If you kiss him or do anything more than hold his hand; I don’t want to hear about it. Come crossover day at school you will cooperate with me. Times like today it better not be more than this once.” Staci stood there, “Unless I’m the master mind do you understand?”

“Yes and I’m sorry,” I said. “I didn’t mean to and I don’t want to do this. You have to believe me.”

Staci said, “Don’t pout, you don’t want to ruin your makeup. You know you make a pretty convincing girl. Your voice even suits you.” Elle and Haley talk with Staci and we’re soon in Penney’s looking at dresses. “Are we going to get her measured or are we going to just go by what she’s already wearing?”

Elle said, “The skirt and blouse are from when I got chunky; she appears to be a size eighth. Not bad for a boy ready to go into eleventh grade.”

I bet with the right exercise and a good diet she could soon be down to a size six,” Haley teased.

I struggled to keep my voice, “Quit that I’m not…” A girl walked over to look at clothes where we were.

Staci looked at some dresses, pulling several out and holding them in front of me. “Tell me which one you would like?”

“They look pretty enough for you or my sisters,” I told her. Elle took a hold of me and pulled me to a mirror. Staci put a dress back up in front of me, “Now, I’ll ask, does the pretty girl in the mirror like this dress?”

“It’s pretty,” I answered.

“Does that mean you think this one suits you more? I agree though the other one goes with your makeup better. I thought you might have expensive tastes.”

“The second dress is, in fact, my favorite of any I had seen. But I would sacrifice the look for a little more length,” I said

Elle walked me over to the changing rooms, “Please go in and try it on and don’t make any fuss about it. If you have any trouble I’m willing to help.” I was torn between being angry and wanting to cry as I went into a woman’s changing room.

I wasn’t sure if I was to put the dress on over my head or to try stepping into it. I decided to place it on over my head. I had to start my hands and arms while the top of the dress was coming over my face. The dress felt wonderful as it slipped over me. Now, I’m getting angry with myself for the beautiful feelings I was having.

I had the dress on and zipped up inches from the top but couldn’t get it further or hooked. “Sis, I need your help.”

I heard Elle reply, “Crystal’s not here only your cousins, so I’m coming in to help.” She opened the door just enough to get through it. With no trouble, my dress was zipped and hooked. “Stephanie, my friend Janice is here so remember you’re our cousin.”

Elle combed my hair into place before I stepped out of the changing room. I received a number of ous and ahs as I went over to the mirror. I turned around and waited for the others to speak. Staci said, “So do you like how pretty it is on you?”

“I can’t believe it looks so good.” I smoothed down the skirt of the dress and fixed a bra strap that showed just a little.

Janice spoke up, “It looks very pretty on you. How long are you staying, before you go back to Denver?”

Haley spoke up, “She just got here Thursday night, don’t rush her.”

“I’m going back as early as Monday,” I said.

Staci said, “That’s good maybe we can do something together tomorrow night since Steven is gone.” Hearing Steven was gone Stephanie raised her eyebrows.


We were home and not even sitting down when Elle asked, “Mom, when is Cousin Stephanie going home to Denver and Steven coming back?”

Mom saw Staci and Elle’s good friend Janice, “Her Mom had called and said it would probably be next weekend at the earliest.” I could hear Staci behind me, saying, “Yes!”

“Don’t get ahead of yourselves; she needs to focus on getting ready to go out tonight.”

Staci pushed my new dress in front of me to show my Mom. “Yes that is very pretty and it should be very nice for their dinner out.” Mom looked to Staci, “Do you think it will be okay for Steph to wear it and go out on a date tonight?”

Staci said with a relatively calm voice, “O yes, she will look very pretty; I just pity the other girl. I heard she and this Brad person were close before. I’m just glad Stephanie will be around longer. So we can become friends and play a little dress up. Maybe I could show her around the area.

Elle nudges me, “Let’s get upstairs, you need a shower, a change to make sure you are ready to go out.” Mom and others complimented how well I walked upstairs. Mom gave Haley a small box of things I was to put on after my shower.

To be continued…

If you liked this post, you can leave a comment and/or a kudos!
Click the Thumbs Up! button below to leave the author a kudos:
237 users have voted.

And please, remember to comment, too! Thanks. 
This story is 3720 words long.