Jack and Jill by Trudy - 9 - Melanie and Sara Sisters

Jack and Jill, by Trudy
9 - Melanie and Sara Sisters

By Jessica C

Melvin thought it was weird to be Jill for Halloween...
That his friend Trudy liked it made it okay...
That he has to act as a pregnant girl was credited to Mel...
But acting as pregnant student Melanie’s roll extends into February…


Marie stays at Marti’s together they have fun teaching and watching Melanie learn to do her makeup and hair better. Brushing and fussing with Melanie’s hair is bringing out a sheen and wave that were missing for Melvin. The first time Melanie raises her arms to help fix her hair brings a shock look and then laughter from Marti.

“Melanie, I thought you were shaving your underarms?”

“I didn’t think I had too with colder weather who is going to see?”

“Gross, I know a few girls agree with you, but while you’re here I want you to keep your legs and underarms properly clean of hair stubbles do you understand? You are going to have the regular concerns of a girl with a healthy concern with your appearance.”

Marti takes this opportunity to shave my underarms. And when she checks my legs, there is a decision to wax the upper portion. I don’t have a clue what I am in for.

We finish the makeup lessons and I am getting ready for bed. When Marti says, “I want to help you put on a gaff.” I am in shock because I’m told it looks like a vagina, “It will even allow you to go to pee in the bathroom like a girl.” That is more than I want to know. Marti says, “They didn’t have the regular gaff, this one has a feature the other does not. You can even take a boy into this gaff if you were to have sex.” That is way too much information for me to contemplate. Luckily for Marti the gaff is already stuck on and I will have to wait to get it off. It makes me all the more a girl as Marie helps me to finish getting ready for the day.

I am lying down as Marti spreads on the wax for the hair on my upper legs. It is very warm and has a pleasing aromatic fragrance. While it is unnerving to have Marie around, she says she is use to what she’s seeing. On the count of three Marti and Marie each pull the wax from the leg nearest each of them. It stings like little pins and needles being pulled out of me. Marie says, “You’re handling the first time better than most girls.”

I prematurely say, “It’s because I grew up a boy.” Aunt Marti says as she pulls, “this area for me is more sensitive.” This time the stinging is noticeably worse. Marie pulls her side more slowly and my eyes begin to water. Marie guides my hand to the area where the wax is off, “Now how does that feel?”

I shake my head up and down and Marie says, “You should try a good pair of silk or satin panties and silk stockings now.” I smile, ‘not caring what the difference would feel like.’ When they were done they spread a soothing lotion on my legs.

Marti asked, “Don’t you and your sister sing in the girls’ chorus this Friday? I’ll see if I can get a pair of breastforms for your bra by then; then the other girls will have a reason to ask why you are smiling so much.”

Now for the first time since the instructor talked about me singing this Friday, I am actually nervous about it. I enjoy rehearsing with my sister, but wasn’t at all excited about the performance. “Aunt Marti, are you and Sherri coming to hear my sister sing?” She says, “I thought you are singing with her?”

“I am but she’s the one worth hearing,” I giggle with honesty.

“Unless Mr. Hurd has changed, he thinks you have a very nice voice. And unless you change he isn’t seeking to woo Melvin into the choir any time soon.”

After that Marie rolls my hair in some soft curlers for me to sleep with.


“Come morning, it is Marie with Marti waking me; she wants to make sure I use a shower cap for my morning shower. I get two calls, one’s from Trudy, “Remember, after your concert Friday we have a date.” We visit for awhile but we’re both distracted trying to get ourselves ready for school.

No sooner I am off the phone and I see a text to call Sara back; I call, “Hey Sis what is up?”

Sara giggles, “The first is as your dating service; Derrick wants to go out with you after Friday’s program. I told him that is taken so he put first dibs in for Saturday. I told him that would work as far as I knew. He’s going to ask you at school. Secondly, if you still have study hall third period, I want you to come to the vocal room so we can rehearse before chorus this afternoon.”

“Kathy called me and says you are even practicing with the cheerleaders. Nice going little sister, even I couldn’t keep up that schedule girl.” I say thanks and she tells me we are both getting a little mushy and way too much enjoyment out of being sisters.


When Marti isn’t looking I pop two more of the pills along with a breakfast drink. Marie asks, “Melanie what did you take with your drink?” I wasn’t looking for Marie and quickly go into denial mode. “I wasn’t taking anything it’s just I’m afraid a cough is coming on.” My phone rings and Sandy asks for me to hurry if we’re walking together. I wasn’t planning on it but it does give me a chance to get away without more conversation.

“Bye, bye Sherri,” I throw her a kiss and grab my books and purse to head out the door. “Unt Melwannie,” Sherri runs wither hands out to be lifted and hugged. “Smooch,” I leave a lipstick kiss on her cheek.

By the time I am out the door, Sandy calls down the block, “Watch it, there’s some ice… this morning!” However she’s too late, and I am not sure if those riding by saw a show or not. It hurt my pride as well as my backside.” If I didn’t want to talk to Aunt Marti I would have turned around.

Sandy enjoyed too much the wiping off the back of my skirt when I got up to her. There was a little freezing rain last night covered by frost this morning. Melanie’s shoes don’t have the same soles as Melvin’s does. But within the two blocks to school I manage to slide two more times on purpose without falling.

Derrick comes over just before Sandy and I reach Deb, Sharon and the other girls in our group. “Melanie, did you speak to your sister last night?”

“She did, I am flattered but I’m still a… still a…” No, I didn’t get cut off or forget what I wanted to say; it’s just that I am not sure what to say. I get tears coming to my eyes and I hurry to grab the Kleenex in my purse. Luckily I do a light dab at the corner of my eye, no damage to my makeup. Sandy sees me and gruffly asks “Derrick, what did you say to her?”

I grab Sandy and whisper, “It was me. He was nice enough to ask me for a date Saturday. I tried to tell him I’m not a girl, but I couldn’t. It’s crazy but I would like to know what it is like to date a boy.” Sandy has this huge smile like she swallowed a canary. “Oh,” she pauses, “That should be cute. Do you want to double with Kenny and me?” I can’t believe she is suggesting it.

Derrick is trying to apologize as we begin to go into the school. Sandy turns to him, “Don’t apologize, just give her a class or two to decide. I think it will be yes.”

I look at Sandy, “You shouldn’t have told him that, now it will be harder to say no.”

Sandy bumps me with her hip, “I’m glad because you didn’t say no. All you need to do is decide if you want to just go on a date with him alone or on a double date.”

I say, “Thanks, thanks for nothing; I thought you’re my friend.”

Sara taps me as she comes back to my locker, “You must have said yes because Derrick’s bouncing down the hall with a big grin.”

Sandy speaks up, “Your sister got all emotional and was ready to cry. She tried to say ‘No’ twice and couldn’t.”

I told them, “It wasn’t quite like that but she’s right, I didn’t turn him down. Because somehow I thought it would be neat to see what it is like to go on a date.” Sara is really puzzled; not knowing if she should be happy or concerned.

Sara says, “Well, I guess I was hoping it would happen; I’ve even thought of encouraging you too, but I don’t want you hurt.” I look at Sara, and I know deep in my heart, I have a sister who is being sweet and sensitive of me.


Sara looks at the back of my skirt, “What, did you slip and fall this morning?” It breaks the ice, and we all giggle. “Get your books and get to class. We can talk third period when you come to rehearse with me.”

I have my things and walk with Sandy to her locker. Once we begin to walk to homeroom I turn into the girl’s room, needing to check my makeup and hair. As I lay my purse down and take out my lipstick and brush; Sandy speaks up, “You remember you’re not to be in here?” I catch myself and wonder what I should do; Sandy says “You’re here now, do it and let’s get going.” Two other girls laugh as we walk out and no one is upset.

I am glad when third period classes begin and I am quickly to the vocal room. Mr. Hurd sends us to the auditorium with a boom box to rehearse. It is our plan to sing our duet at least three times. I did not notice as we sang through the song the second time that Sara’s friend Dawn Michaels is in the back listening.

“You two are very good together with the exception that you both sound week. Sara, I know your voice is much stronger; I suspect you are holding back not to drown out your sis… sister. Melanie, you need to sing as well as you can and not hold your sister back.” The third and fourth time through the song and Sara has a place in the song where she is singing as my back-up. She comes and gives me a hug as we finish the song the last time. Dawn acknowledges we were singing much better.


During lunch Sandy asks how rehearsal went with Sara; I begin to tell her with a cheerful voice, but worry someone will think I like being Melanie. “It is okay Melanie, I enjoy singing with my sister as well.”

“Yes but we’re not sisters. We’re really a sister and brother.”

“You are Mel for four months you are living as a girl. If I were you, I would enjoy singing with my sister.” I hear what she’s saying, but it is not people like her that I am worried about. The next thing I see is Sandy attacking me with a lipstick.

“What are you doing, are you crazy?” I caught her hand just in time, but she is not letting up.

One teacher asks, “What’s the problem here?”

Sandy joyfully speaks up, “I want to write ‘girl’ on her face. She’s afraid others will find out she’s a boy dressed as a girl.” Two other girls giggle nearby.

Ms Simmons replies, “Well I think it would be a rare student that doesn’t know that. The only surprising thing is how well she is doing it.”

“Melanie, Sandy has been one of your best advocates for acceptance; I hope you aren’t pushing her away with a plan to cause problems. If you need someone to talk with I can give you a pass to see Ms Braun or you can talk to a teacher like me. I know I would be very willing to listen.”

Ms Simmons must have seen my response because she soon asks, “Sandy please go back to what you are doing.” “Melanie, you come with me for a minute please.” I’ve had Ms Simmons for two subjects before so I’m sure by her voice that I am not in trouble.

She asks, “So Melanie, what is your problem?”

“Ms Simmons, I’ve had you for two classes already and I like you as a teacher. You would laugh or think I’m crazy for… No, I can’t tell you, I’m sorry it’s not you but me,” I tell her.

Ms. Simmons says, “Melanie, this is just a guess. Are you afraid because you like being a girl or wearing their clothes?” I’m startled, ‘How does she know?’ I’m ready to cry, but I’m fighting it.

“Melanie, come with me please.” We go to her classroom, “I won’t be having a class the next period, so we can talk if you would like or I can give you the pass to see Ms. Braun.”

I begin to talk, “Why did you ask if I’m afraid I might like being a girl or wear their clothes? Am I looking like a sissy?”

She asks, “You think girls look like sissies?”

I say, “No, they look like they are suppose to, but a boy trying to look like a girl is called a sissy.”

“Pardon me Melanie,” Ms Simmons smiles, “You shouldn’t call people names, but I expect there might be a few that call you a Sissy, but they’re ‘Jerks’.” I can’t help but giggle. “This might upset you, but you look like a normal girl and not a boy just in a dress. I know you enough to say you actually look happier as Melanie that is why I am asking?”

I ask her, “What if I told you, I am happier?”

“If it were me, it would be a relief that someone I could trust knew.” She pauses, “I’m honored you would trust me that much.” I have some tissues that I use to dab the corner of my eyes.

I say, “You’re right, it is a relief and I do trust you. I didn’t plan things to happen like this. It wasn’t even my idea. But I kind of like it happened. Tomorrow I get to sing with my sister; Melanie has a nice enough voice to do that. A boy looking up to her sister as a role model usually draws laughs but it is true.”

We talk for a while and I am ready to go back to class, but need to fix my appearance. Ms. Simmons says, “You are becoming quite proficient with your makeup and getting better with your hair.” I look to her and offer her my hair brush. She takes the brush and helps me, “It takes some experience and a good mirror to touch up one’s own hair, especially in the back. Now get going and remember to come back now and then.” She gave me a note for missing most of my next class.


Sandy and Aunt Marti both notice I am happier and more relaxed but I’m not telling them about my talk with Teacher Simmons. I have to get work and Trudy is glad when she sees me, “Melanie, you are… I’m not sure but you’re happier.” She pulls me in the women’s restroom off the break room. “So tell me what has happened?”

“It’s good but can we visit after work,” I ask her? We agreed to go out for a short time before going to home. We agree it is not a date just us being best friends.

A mom comes through getting groceries with two small girls in dance outfits. I recognize Sadie the oldest of the two girls. Her mom whispers in her ear and then Sadie speaks up, “Melanie, I know you, you’re my neighbor. Can you come and see me and sister in our program Saturday?”

I ask if she will come to our concert, her mom reminds me we sing at the elementary school tomorrow during school, before the concert. “I don’t think they want young kids in the concerts disrupting your performance.”

“I would be babysitting my aunt’s little girl so you probably don’t want us there either?” The Mom smiles as she hands me two tickets, “We really don’t mind, so I will expect to see you there.” They are surprised when I lift Sadie. “Sadie, you are so pretty in your outfit.” I twirl her around and set her back down.

When I set her back on the floor, I hear behind me, “Well, I see you have learned how to kneel down in a skirt.” I stand up and see Mrs. Walton. I turnaround, smile and curtsy to her. Once again she is taking a picture.

“Can you take a picture with me and Sadie and maybe her sister?” She agrees and the girls are happier than I am. I introduce Sadie’s mom, “Mrs. Walton this is Ms. Morrow and her two pretty daughters, hopefully you can email a picture to her as well as my Mom.”

Once work is over Trudy is already waiting for me and we ride up to a pizza place on the highway. “So what has you happier than usual,” Trudy asks?

I tell her about Sandy’s attempt to paint my face and Ms. Simmons. “I was afraid I was in more trouble, instead I tried talking to her. She asked, if I was afraid because I like being a girl or wearing women’s clothing. Instead of being shocked she guessed I was relieved.”

“O my Melanie!” Trudy’s eyes open wide. “What did I do? I didn’t intend to change you.”

I retorted, “So you think I’m sick for liking it now?”

“No I just feel bad because I find I like you even more as a girl. Look at me I wasn’t attracted to girls before, but that changed with you.”

I asked, “Trudy, you changed after work, before we came here. Did you do that just to impress me?”

“Yes and I’m sure Melvin wouldn’t have noticed,” she said. She’s right, I didn’t notice before when a girl changed outfits or redid her makeup with different colors or that she did different at night.

I ask, “Does noticing make me a girl?”

Trudy giggles, “A little more so, I think; I hope that being a girl is not bad?”


When I get back to Aunt Marti’s the long dress I am to wear for chorus and singing with Sara is there. I have worn a fairly long skirt, but this is a dress and it is so long that it requires me to wear heels. I hurry to find the slip for it and after the slip is on I ask Aunt Marti to help me put on the dress. I can’t help but notice for as long as it is. I’m happy that it is pretty and once zipped will hug my body but allow good movement. Marti has the back undone as she puts it over my head and my hands find their way through the sleeves. There is a shiver going through my arms resulting in Goosebumps. As it slides down my front and back, I glory in how it feels like a beautiful shower of water running down my body.

Marti zips up the back and hooks the clasp at top as I step into a pair of heels. Luckily Marti has me holding my bed post to keep my balance until it is on and I’m comfortable in the heels. The heels are three inches high, Marti says, “I am surprised you and your sister wear the same shoes. Now come out to the living room and sit down and talk to me?”

I say, “I don’t want to sit down, I am afraid to sit wearing this dress.”

Sara says, “That is the very reason you need to do it. You will have a minimum of three changes tomorrow. Come concert time before and after; you are going to need to sit when you get a chance. Wearing a long dress, changing and walking up and down on the chorus risers will be your biggest challenge so far.”

I start to walk out in to the living room. “Melanie don’t think about it so much just do it.” Instead of looking down I look to the chair I plan to sit in. “You might do better sitting in the hardback chair, you won’t sink down.”

It isn’t too hard as it ran my hands down the back of the skirt, it helped me to slow down when I sat. Marti puts a napkin in my lap and hands me a cup of hot tea. “You did very well young lady; I hope you are pleased with yourself. Come January you won’t be able to wear a beautiful gown like this.”

“Why won’t I be able to do it in January?”

“Have you already forgotten you are pregnant?” In fact, I had and what Marti’s doing a reality check. She has to remind me to sit up twice as we’re talking.

I sense some tension as Marti speaks, “I hope Marie didn’t really see you taking anything. I know I suggested taking something could help you feel more like a girl, but I wouldn’t want to have to explain that to anyone, especially if it gets back to my sister, your mother. I don’t think it will hurt anything as long you’re not overdoing anything.”

“I’m not Aunt Marti and I hear what you are saying.” Just as a precaution if they were to be taken away I take another pill tonight. I know they won’t really change me but it helps me to dream. I have pleasant dreams, wake up early with a smile and get ready for school including the long skirt and blouse for our performance over at Lincoln Elementary School. I eat a breakfast of yogurt and fruit before putting on my blouse and finishing my makeup and hair. Thankfully no cheer practice for me today.


The phone rings and it is Sara, she has the car and is giving Sandy and me a ride to school.

“Woe, L’tle Sis, you are getting prettier each time I see you. You are getting better about dressing and looking like another girl.”

“Thank you, I think.”

Sara confirms, “Yes it’s a compliment.”

Sandy comes out and gets into the car and I’m feeling jealous about how nice she looks. I move to put on more makeup, but Sandy speaks up, “That would be a mistake, it won’t make you look any prettier, it does the opposite.” I look over to Sara and she has a little smile and shakes her head in a way that indicates Sandy is right. I put away my lipstick and we are already parking at school.

John from work sees me at school and asks, “Aren’t you getting too serious about this?”

Sandy speaks up, “No, it is just what she/he needs to do for our concert and to sing at the elementary school after lunch.” Sara adds, “And she’s singing with her big sister and I want her to look like a regular girl so butt out.”


The concert at the elementary school is like a dress rehearsal for tonight. I am glad we have three songs for me to relax and regain my voice. Sara turns and pointing ever so slightly she whispers, “Sing to Sadie.” I do so and it adds to the feeling and energy that had been missing according to Mr. Hurd. After the concert Ms Morrow brings Sadie to me asking “Did you sing to Sadie like my Sadie is saying? You sang so well.” I wasn’t hearing as much as I was leaning down to pick up Sadie and give her a big hug and kiss.

I felt a tap on my shoulder and turn apologizing to Ms Morrow to see my Mother leaning to give me a big hug. “Way to go young lady, I am pleasantly surprised by how well you sing.”

Sadie speaks, “She sang to me. I want to be like her.” Mom and I giggle then each gives her a kiss on the cheek.

I go home with Mom and Sara; Marti brings over my dress. Even more important to me is Suzy is with her. “I sure hope Suzy is going to our program tonight.”

Marti, “I wanted to ask if that would be alright with you two.” Sara suggests they sit closer to the front.

Sara says to me, “You will eventually need to sing out without a crutch.”

The program begins and I look to find Mom, Dad, Suzy and Aunt Marti. I’m surprised to see Trudy sitting with them. I can’t hear what she is saying, but I know it is: “Melanie, you are so beautiful in your dress.” She is pleased when our eyes connect and I smile.

Afraid of emotions, I look away from Trudy, I focus on singing to Suzy and in tune with my sister. We aren’t suppose to but I grab and lightly squeeze Sara’s hand as we end the song. I turn and curtsy to Sara, acknowledging she is the lead singer. After the concert Mr. Hurd is quite strong in telling me that was inappropriate. He did compliment us on the song and the chorus for how well we sang.

After the concert I am overwhelmed by my family and other students praising me as well as Sara and the other girls. I am invited to an after concert party but I also have a date with Trudy. I love the dress but I am glad when Sara holds out a shorter dress to change into. Trudy and Sara accompany me to another room where we can change. It is pretty print dress and I recognize it is one of Sara’s dresses she is currently wearing. “Thanks Sis, this is extra special of you.” “Right now you are Melanie and not my little brother wearing it.”

My friend Rhonda sees Trudy with me and she says, “If it were me, I would pass up the party and go on my date.” I quickly say, “Thank you, Rhonda, please say Good-bye to the choir for me.”


Trudy and I spend much of our time in her car talking. Trudy says, “You know, I’m getting a little jealous of the attention girls from your school are giving you. Are you sure that Sandy really has a friend Kenny that she’s serious with.”

That Trudy would be jealous of me is a big surprise as she is so high on a pedestal to my thinking. I do confess, “I’m beginning to enjoy this more than I thought. It is even getting hard to remember what my regular voice sound like. Sometime when I talk with my parents I revert back to it, but not as often.”

Trudy asks, “What are you using for your complexion. Your complexion almost looks like it is changing.”

She gives me a kiss as her hands slip into dress. “Trudy, you unzipped my dress without me knowing.” She stares at me, waiting for me to say something. Now having a long dress on makes it awkward as it would be very difficult to take it off in the car.

Trudy says, “Don’t worry, it’s not about sex with Melvin… There I said it… Melanie I’m finding myself attract to you as my girlfriend. And I don’t even see myself as a lesbian. That is apart from you.”

To be continued…

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