Stephanie’s Chance - 2 First Date

Printer-friendly version



Audience Rating: 



Character Age: 

TG Elements: 

TG Themes: 

Other Keywords: 


Stephanie’s Chance - 2
First Date

By Jessica C

I was out of the shower and I was to pat dry. Elle told me that’s how girls dry themselves. I was to wrap the towel around me in girl style. Elle suggests, “Use my robe again, I need to help you with somethings before you get dressed.” I was praying she would tell me I didn’t have to continue to dress as Stephanie or go on the date.

We were back in her room when she showed me the breast forms in the box. I was very upset and protested again. Elle said, “I think Mom is going the extra mile to make sure no one discovers the boy going out tonight. This will look a lot better with your dress.” She pushes me down on her bed and has me lay back so she could put the breast forms in place securely and correctly. She threw a towel over my lap.

“Are you excited to be going out on a date with Brad tonight? I hear it is to Mario’s and then the drive-in.” Haley chimed in, “Plus you got to buy a pretty dress.”

Elle told me, “Please hold your breasts in place and be careful not to move them. It would be bad to see one stuck under your armpit.” Haley giggles and while I thought the image was funny, I wasn’t laughing. Holding them in place, it warmed up and felt like another member of my body. It is the first time I held a breast cupped in my hand and it is supposed to be mine. I think it is one of those oxymoron things.

When it came the time that I could sit up, my sisters already have the satin bra ready to cup my breasts snugly. “We don’t want you infatuated with your own breasts.” ‘I’m thinking, too late.’

Janice enters the room shortly thereafter, “What’s the problem with your cousin doesn’t she know how to dress?”

“She has been pretty much a tomboy and isn’t used to getting dressed up. This will be her first date with a boy so it is an extra big deal.” Staci brought out 3” heels.

“I thought I was to only wear two-inch heels?” I knew someone would come up with a reason to change that.

“You can switch to lower heels or flats for the drive-in if you must. You should wear a nice pair of heels to Mario’s. These are an old yet very pretty pair of mine. I’m hoping they will fit you.”

“Don’t you think they are very pretty with your dress,” Staci asks?

As my feet slipped into the heels and I noticed the difference in height, I smile. I looked into the mirror to see my feet and legs, and my smile grew. Janice commented, “It looks like you made this girl very happy today.”

I ask, “Why did you wait for me to put on the dress?”

“So you would enjoy how beautiful your legs are while you can see them and then again as you look down and then again as you see them in the dress,” Elle says.

I insist Staci and Janice leave the room before I take off my robe. I raise my arms so the dress can be placed on over my head. It feels wonderful sliding down my arms and body. Something tells me, ‘Don’t let others know how much you enjoy this feeling.’ My head is out and I can see and feel it gliding down. I know I don’t have hips like Elle or my younger sister, but I swear I can feel the waist of the dress resting on top of them.

Elle asks, “Now reach back and see if you can zip it up and hook the top.” I did and I was surprised. It took some effort to move my arm and to coordinate my hands in grasping the zipper. But I was able to do both.

“Why is that so important,” I ask?

Elle says, “Sis, you do not ever want to be at the mercy of a boy to help you do that. There might not always be another woman around. Each time you can gain a little confidence in what you can do, that is good.”

“Thank you,” I said. I was hoping Janice did not hear or think it strange that Elle called me Sis. Somehow, down inside it felt good, though again I thought the feeling was wrong. Looking into the mirror and seeing I had cleavage; though it is normal for a teen it shocked me. I was looking very pretty for a girl.

I sat down in front of Elle’s vanity as I’m told to begin my makeup, as Elle took to doing my hair. Staci’s back and guiding me in my makeup even more than Haley. I could see Staci’s style on my face, while it was different and it suited me. I had a pleasant smile on my face thinking we were working together. I had wanted to learn to do makeup, but always thought it would be her face we were working on. Staci winks at me; we have a tendency to know what the other is thinking, so her wink and smile spooked me.

It is 4:45 when the makeup and hair are done and the jewelry’s going on. The dangling clip on earrings look nice, but they hurt. When I stood, I spin around once in place. Janice said, “I thought you said she didn't use to this?”

I cover my actions saying, “I had always dreamed of doing that. I couldn’t help but try.”

Elle said, “We will need to talk about that another time.” Staci hands me my purse open and I check it as best I know. There were things I didn’t want to mention since they were for a real girl.

Elle reminds me, “The makeup you used for tonight is still on the vanity. You should make sure it is in your purse.” I ask about the compact and the little case with the eye makeup. “Very good Steph, you don’t need two of those and the smaller compact is better for your purse and it has a mirror.”

Janice is sent down first to tell Mom that I am ready and to see if Brad is here. I just heard a car pull up to the front of the house. I so want to back out. I’m afraid of me being with Brad. I’m comfortable that he wouldn't get abusive or try to embarrass me. We were the best of friends since we were little. It was more about our past friendship being so close. I was six when I first kissed Brad saying boys were closer than a girl with a boy. Brad said I was not to kiss him first ever again and especially around others. I was nine or ten when he brought a panty a cousin. That started me feeling more like a girl around him. I was eleven and Brad was fourteen when our close friendship became more involved. It is a secret I have kept well-hidden; I had hoped it might have been in my past.

Mom wants me downstairs so she'll be able to enjoy seeing me before I left. I slowly walk down the stairs and my mother enjoys seeing me as a girl, I could tell. “You look very nice Honey.” She gave me a handkerchief for my purse. I thank her and give a little hug like my sisters always did with her.


Brad knocks and waits till the door is opened. I am glad he looked around before he said anything. “So is this Stephanie,” he guessed? I let Elle introduce everyone. Brad seems to know Staci is more than a friend but he does not ask. I felt like a lamb going out with a wolf, but then again I did not pull back.

We were walking down the sidewalk when Brad gave me a small kiss to the cheek as he said, “You look great. I like your perfume as well.” When he opened the door to the backseat I took a breath and remember to slow down and sit first. I sweep the skirt underneath me and kept my legs together as I sit and turned to bring them into the car. Kari turned around and comments, “You look very beautiful tonight. I appreciate you dressing up to go out to eat. I do like dressing up. I am Kari and this is Jake.”

I gently say, “My name is Stephanie; I am a cousin to Elle and Haley.”

Kari said, “But you already know Brad and are comfortable going to the drive-in with him?” I sensed that Brad mentioned he already knew me. Instead of moving over I let Brad go around the car and let him move to me if he decides to. We’re on our way and I wanted the conversation to change if it would. Kari and Jake go to the same university as Brad. Jake is a junior and Kari is a sophomore.

Jake said, “Brad was going to bring a friend named Steven, but when he saw you he changed his mind. I guess when he saw you he changed everyone’s mind. A penny for your thoughts,” Jake said?

I said, “Nothing goes for a penny anymore plus I’m not ready to share quite yet.”

Jake is the one who made the reservations to Mario’s. We have a nice table with no waiting. One waitress takes our drink orders. Kari suggests, “Stephanie, let’s go and freshen up.” I slowly stood up and followed Kari. I was nervous about our need to go to the bathroom. I wanted to wait until we were ready to eat. I only wanted to go to the women’s room once tonight. I rather not go to the drive-in at all. I wash my hands, check my hair and makeup going slow enough not to rush Kari.

I couldn’t help but check out her makeup, outfit, and hair. She’s truly a beautiful woman and way more mature than me. We got into small talk and she asks me if I’d considered going to Brad’s university. “If I went there it would have to be for me. I would need to know better what it offered me.”

Kari says, “I don’t have any little sisters; I’d be happy to host you for a weekend and show you around as a girl. It would not be the same as Brad would. You’d be free to see him but not depending on him.”

I thanked her, “That is very nice of you. Tonight, I would just like to get to know you as well as be with Brad.”

Kari asks, “If we get a little involved at the drive-in will you and Brad be okay with that? I had sensed Brad knows you enough to be close.”

“You and Jake hopefully won’t be worrying about us,” I told her.


We were back to the table, an appetizer had been ordered and was there with the drinks. Kari encourages me to order a lobster tail like her, saying it should be small enough to manage. I had only had it once and not at a fancy restaurant. Brad monopolizes, the talk about what he had done this past semester as well as on his summer internship and how his studies were going. I insinuate he’s neglectful as well as self-centered.

The touch of his hand on mine felt nice. I wish Mario’s would last the night as I was safe there but it didn’t. We were to the drive-in, the College Center Star-Lite Drive-in near Easton with time to settle in. It was nice that Jake drove a good size Lincoln. Jake looks back as if to ask if we will be okay. I hear Kari say, “We girls have already talked and she’s comfortable.” With a smaller voice, she said, “I’m not quite sure she’s ready for Brad but that’s their problem.”

Brad took his time before he finally nibbled on my ear, “I’m glad to hear you’re comfortable but I plan to take it slow and we’ll see how the night goes.” I really try to watch the movie and talk a little. I’m impressed that Brad has grown and is not quite the person I knew. He has matured and for now, I like him better.

His first caressing kiss and his touch of my waist remind I am still attracted to him. We do go slowly and it is mostly kissing and his hands gliding over me as the first movie ends. I reach the back of my dress, to re-hook it. I noticed it had become a little loose. We step out of the car and Kari suggests we stretch our legs. “It will be easier if we take off our pantyhose before they get back to the car.” She smiles at me, “Are you willing?”

I say, “I’m not wanting to but I’ll probably have trouble saying ‘No’.” She opens my door suggesting I get in and get ready. She is up in the front seat and her pantyhose and panties are soon off. I saw the yellow satin panties go to the driver’s side. I feel vulnerable as my pantyhose come off.

I’ve tried to please Brad and I thought I had. I knew he was happy with how I treated him. Now he's gently pushing for more as I fight my emotions. Brad knew he moved me earlier and that I’d be willing if he pushed for it. We had been intimate before but he had never gone inside of me. I didn’t know what it would feel like. I didn’t expect to like it as I did. It was neither cheap nor was it with the love of my life. Yet he was my first and that made it special.

Brad, I sense is bisexual and now I’m not sure about me. He pushes himself into me and I know tonight I’m a woman, his woman. I can feel him inside and something is causing sensations that I had never had before. It’s kind of like… I’d prefer to be fully a woman. I don’t understand how I know that but I’m pretty sure, this isn't it. Brad took his time like he was going out of his way to please me. I sensed when he was creaming me by the heat and warmth of him inside of me. I did not expect the explosion of my feelings. My senses going off my measuring scales as they were.

Jake and Kari had been very content in being vocal in enjoying their passion. I guess Kari is amused with my joy. We’re all glad there were no cars next to us.

Somehow I did not sweat but as Kari says, I’m a glow and very warm in the face. I didn’t worry about the pantyhose but I did get my panties back on and make sure my dress was back right. After the drive-in, we stop for a drink and some small talk. I hurried to a stall in the women’s bathroom to slip on my pantyhose before we return home. My drink is a small glass of wine. I’m surprised they served me. Brad whispered, “It is nice you don’t look your age.”


I didn’t worry about the time when I got home as I was happy my mother would not be awake. Elle’s at the top of the stairs and I tell her I’m glad mother is not awake. She laughs, “Believe what you want. Did you have a good time?”

Elle wasn’t insinuating anything; she didn’t have to. “You know don’t you?” I don’t know why I asked or said that.

Elle says, “Don’t say anything right now unless you’ve been hurt. Go take a shower and get ready for bed. If you want, Steph’s welcome to be with me or you can sleep on your own.” I went and did as she said. I used a shower cap so I didn’t need to worry about wet hair. She had placed a nightgown on my bed; my pajamas were there too. I knew the choice was mine.

I put on the nightgown with a panty and made my way to Elle not sure about where I’d sleep. Elle had been working on her computer but shut it off to give me her full attention. I was never so pleased to have her as my sister. She sat up against her headboard. I nuzzled in under her arm. I had seen Haley with her before and I was happy it was my turn.

“Were you Stephanie tonight?” She knew how I was dressed, the question was not about that.

“Did you think I would be?”

“I only knew it was to be your decision if it were a good night and it seemed to be so. But that didn’t mean you would be Steph.”

“I don’t understand it, Elle. Will mother know? What am I to tell her?” I didn’t dare look Elle in the eyes but I was content to be with her.

“It is okay that you don’t. Hopefully, you know I can’t tell you all you would like. I know Mother is proud and loved you tonight. I think she wondered about what we helped you to do. I’m sure she hoped it would be a simple date as she first intended. What she knows or thinks you’ll find out from her. What you tell her, will be up to you. …It is better you don’t tell her something than to lie about it to her.”

“Elle, I didn’t even think I like Brad anymore. It’s just we’ve always been close. First, we were just two close friends growing up.” I knew I was close to saying more than she wanted to hear.

“You don’t need to tell me unless you want to. All I want to know is did you enjoy the night?”

I wasn’t sure what I wanted to say, I only manage a sound, “Mm-hmm.” I wanted to cry but there was only the water in my eyes, I didn’t cry. My head was now in her lap and she was stroking my hair.

“Do you love Staci,” she asks?

“Yes, but I’m not sure if she’ll love me anymore.”

Elle’s pretty sure, “She still loves you and she will always be one of your best friends. You will need to take it a day at a time. She wants to meet Stephanie. She might be wondering if she loves Steph or even needs to.” We didn’t talk forever, nor do I remember much. She left a half hour after I did.


I woke in Elle’s bed, though she was already awake and up. Mother came to get me up, saying it was now 9:00 a.m. She sat on the bed next to me. “You looked very beautiful last night when you went on your date. I hope you are not angry with me for pushing you out. Somehow I thought you needed to get through last night and I felt there was no way around it.”

I’m not sure what she meant and neither of us went there. “I think Staci is hoping to see you today, so you might want to find another dress or outfit to wear.”

“You made it hard on Stephanie not to stay around.” I stared at her.

Mother says, “She can leave any time you want her gone; I just made it possible for her to stay awhile. If need be, I’ll take responsibility for her to be out of here. If that is what needs to happen.” I knew she was seeking to be supportive. “Staci cares about you a lot and I’m sure, like your sisters, she’ll go the extra mile for you.”

My mother tries not to but she looked at my figure, especially my breasts. “I understand you’re interested as a mom to see and make sure I’m alright. Last night brought new feelings.”

“I am glad you understand that I care and that I’m here for you.” My mother is different than I expected. “If I could help brush out your hair sometime I would like that.” She smiles, “So how did it feel to be kissed by Bradley? It might not have been the first time, but last night it was Steph on a date with him.”

“I’m not in love with him and it might be our first and last date. But, yes it felt nice. It is not him who concerns me as much as being Stephanie, and liking it,” I told her.

“I hope Elle told you for me, to take one day at a time.”

I joked, “How many days do I have?”


I look up and Staci has come to Elle’s door and is automatically turning around. “Staci, please don’t leave.”

Mother hands me Elle’s robe. “Put this on and get up then.”

Staci had a pleasant smile, and as soon as my mother was out of sight she gave me a kiss. Our lips meeting is very nice but feels different. Staci’s happy, “I love you very much; I hope that didn’t change last night for you. It is the first time I kissed a boy with traces of lipstick.”

As we went down the hall to the stairs; Haley comes out of the bathroom. “It looks like he got you more than once.” I turned my head and glared at Haley. She looks to Staci and knew what I was thinking. Haley knew she spoke up without thinking.

Staci asks my Mom, “Can I take Steph out shopping?” I knew my mother had spent more yesterday than she anticipated. So I anticipate the answer to be ‘No’ and yet I didn’t want to disappoint Staci.

“Mother is it okay if I spend some of my savings?” My mother tells me, “Yes but you are to spend wisely. You can use up to $10 of your money. But you don’t need to spend even twenty-five dollars if you don’t have to, except for Staci.”

Staci has gotten out the yogurt and a spoon for me, “Go for it girl, eat up and then get dressed.”

I quickly change and come down thinking I was ready. Staci sent me back up, “I’m not taking a boy dressed poorly as a girl. Steph, a girl can’t throw on clothes like a boy and expect she’ll pass. When you dress as a girl you need to be smart about what works with your body. You looked very pretty and all girly yesterday.”

My mother says, “She will need to get dressed again on her own or with her sisters or my help. However, you might go up with her and help select what would work for her, if you’re willing.”

Staci patted my buns, saying, “Get up there and show me what we have to select from.”

She had selected several things for me to choose from. After I selected a cami, a blouse to go over it and a skirt she remarked. “See that, you have a good sense of fashion if you think about it. The same is true as Steven, but he usually doesn’t make the effort. It is easier for a girl to look good as we have more options and colors to select from. What you picked out is going to be very flattering.”

Staci waits for me to get dressed before she came back into my room and helps me to do my makeup and hair. This time, she is the one after me to learn to brush out my own hair. She helped with much of it, as I learn more. She tweezes a few more hairs out of my eyebrows.


We go over to Staci’s house as she wants to change into something better to go along with what I chose to wear. “Don’t say anything to my folks until they do. Then just say hello.”

Mrs. Miller quickly greeted me, “Hello, are you and Staci going shopping? You can call me Pam or Mrs. Miller if you like.” She stood there quietly hoping I would introduce myself.

I finally said, “Hi Mrs. Miller, I’m Stephanie, Elle and Haley’s, cousin. Yes, we’re going to go shopping. She just decided to change what she was wearing.”

Mrs. Miller starts to speak, “I thought she was going to go shopping with her boyfriend Steven…” I could see it dawn on her who I was. Mr. Miller came in from outside and she said, “Dear this is a new friend of Staci’s her name is Stephanie.” Mr. Miller looked up said hello and went on wherever he was going.

“Did my daughter teach you how to use makeup? I can see a little of her style. You make a very pretty girl. Though I’ll be truthful, it seems more than a little strange to me, no offense.”

Staci came out to the kitchen, “I see you met her Mom, what you think? Stephanie’s aunt says she would be here a whole week before she goes back and Steven comes home?”

“I think Steven is already getting an eye opener where he is.” Her Mom surprises us, “Is it okay if I take you two out shopping?


Initially, it’s awkward going shopping with Staci and her mother, but as Staci hints, “It might be cheaper this way as Mom tends to buy some of what we choose to get.” She’s even understanding of us both sitting in the second row of seats. Though she said, “You are to behave like two girls shopping instead of being with a date.”

“So Stephanie, what caused you to decide to dress as a girl? You must have had your mother’s permission and your sisters help to look natural and pretty as a girl.”

Staci spoke first, “Mama, it was just that there is a changeover day or two at school each year. I got Stephanie to promise to dress as a girl. He bet me that he wouldn’t look like a girl.”

Mrs. Miller said, “I can see that you lost the bet, Stephanie. You seem to be taking it very well. Why is it that you might be staying around for a week as Stephanie?”

“Mrs. Miller, I’m actually being punished because I got way out of line in talking back to one of my sisters and my mother thought this would be a just punishment.”

We were to the mall and Mrs. Miller was lightly giggling as we walked into the Von Maur store. It is an upper scale department store for our area. Mrs. Miller took us over to the women’s sections and to some expensive women’s panties. “I would be amused to see what you thought of some delicate undies? Maybe, like a good set of panties and bra or maybe a satin camisole?”

Staci is ready to speak up for me, but Mrs. Miller cut her off. “Relax, it’s not like I’m going to buy her a whole outfit. But it is like we have a chance to dress up a Ken doll in Barbie’s clothing. Having a nice panty and bra for the week could be a nice experience for Steph. You know I could easily be very upset, but I thought this would be nice for her.”

Mrs. Miller is good to her word, buying me a peach satin panty and bra set. Though before buying it’ she insists I try on a satin lacy pastel yellow camisole.

We stopped for tea and a Danish, and Mrs. Miller invites me over to dinner Wednesday night. It will be to eat with her and her two daughters. “Mr. Miller is to be out of town that evening.”

Staci and I are allowed to shop for over an hour on our own. Staci and I find and tried on a number of outfits. Staci picked out a pair of designer jeans and a beautiful skirt and blouse combination. But she waits to buy them hoping her mom would buy it all or pay at least for a good portion of what she wants.

Staci found me a very pretty mini-dress that I had trouble changing into. I was glad her mother wasn’t around as Staci need to help zip up the back, it was very snug. The zipper was a little difficult for me to reach, but the way the dress looked would be worth the added effort. While I thought it was way too short for me, I knew it was not short as a mini-dress might be. Staci talks me into buying the dress though a half size bigger, she has me wait until her mother is back.

We were waiting for Staci’s Mother as Staci pulls me into Claire’s to look at earrings. While we were looking Pam Miller caught up to us. “You know Stephanie, you should have your own birthday, something similar to Stephen’s but so you’re two months younger. How about we get you a couple of pairs of earrings to celebrate?”

I give in and say, “Yes.” I went to choose from the clip-ons, but Staci steers me over. “Mom meant these and you agreed, so pick some and sit up on the chair and I’ll get someone to help us. Hope the saleswoman, a cute college girl asks, “One, two or more?”

I said, “Just two please.” Expecting one on each side. She understood it differently and I soon had a cute pair of studs and small hoops. I'm told to go with these until the opening heals.

Gloria a college student shopping in the mall, introduces herself and asks, “Please don’t be offended, but I was wondering if you could help me with a project at the university?

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:
155 users have voted.

And please, remember to comment, too! Thanks. 
This story is 5150 words long.