Jack and Jill by Trudy - 19 – What Will Change?

Jack and Jill by Trudy
19 – What Will Change?

By Jessica C

I returned to Aunt Marti’s and Sara had come with me for the night. We both give Aunt Marti big hugs; Sara sat with her as I tended to dinner. Aunt Marti had much of it ready to cook. Cooking dinner gave me a quiet time to reflect on the last few days. I’m tickled; Dr. Kylie and Mom are supportive with my change. It is nice to feel like I’m being treated maturely.

Marti and Sara come in and Sara pushes me aside, “Pardon me but I’m taking over so our dinner doesn’t burn.” I look and I had everything set to high. We’re all lucky they came in when they did or we’d be eating burnt offerings.

“Is something you want to tell Trudy distracting you,” asks Sara? “Maybe you need to go see her at work.” Aunt Marti smiles as she’s handed me her car keys.

I said, “I already sent a message for her to call me after work.”

Aunt Marti stops me as I try to pick up Suzi. “Please go and see her at work; your mind is already there.”

I go to my room and make a quick change; I put on a simple silver grey skirt that Trudy has commented on. I put on a pink blouse with a crocheted lace vest. It’s the first time for this combination; I think they make a nice outfit. I do my make-up a little bolder but not with the flash if it were a date. I pass Sara and Marti’s quick inspection. It only takes a few minutes to get to the store.


I can’t help but reflect as I walked in that all this started with coming dressed as Jill with Trudy as my Jack. I noticed on the way in that Trudy’s on register nine and the store’s modestly busy. Some workers and a few customers notice me when I come in. Some aren’t putting a name and face together yet. I walk casually to Trudy’s register. She smiles as she sees me and her eyes shift to the left, seemingly encouraging me to look there as well. A giggle climbs into my throat. Mrs. Kendral is Trudy’s customer. She’s the owner’s wife and someone who’s been very kind to us.

I haven’t seen her in over a month but she quickly smiles as she notices me. “Hi, Melanie” I detect some teasing as she says, “I’m afraid you’re distracting her while she’s working and you should know better than that. My suggestion is that you tell me what has you looking so radiant tonight and she can listen in.”

“Truth be told Ms. Kendral, my aunt kicked me out and told me to come and see Trudy. I was way too distracted to be of help to her.”

Ms Kendral asked, “Could you turn around slowly, I want to see now proficient you are with clothes, hair and make-up?” I twirled slowly around as I assured her, “Yes, I’m getting to be, but I did have my sister and Aunt checked just in case.” I go quiet and Hannah quickly picks it up.

She turns to Trudy, “It must be something special; I suggest you try to take a break after me.” Trudy smiles to both of us. Her eyes ask what’s up. I shake my head and try to convey with my eyes its good news. Trudy shakes her head, “It’s very good to see you, I’ll be eager for our visit.”

I didn’t notice but Hannah had come over to me, “I hope you don’t mind how much of a girl you have become?” Then she dropped to a whisper, “Would you like to remain as Melanie?”

My shock must be apparent as she continues. “While I haven’t seen you to talk with in a while; I have seen you around town and once with a few shopping bags coming out of Carol’s Dress Shoppe. They say it’s easier to tell what’s real when the cameras aren’t on.” I hadn’t realized she grabbed a gift card as she was checking out. I did hear her tell Trudy to make it for …fifty dollars. Ms Kendral hands it to me, “I hope you like New York and Company.”

I’m speechless, till Trudy giggles, “Just say thank you, close your mouth and smile.”

“Thank you Ms. Kendral but fifty dollars is too much.” Trudy coughs lightly, “That was one hundred and fifty dollars.” I begin to shout my thank you and reach over to give Hannah a big hug with big tears in my eyes. “This day had just been too special… How did you know! The doctor only agreed earlier today. I came to tell Trudy before I told anyone.”

Hannah and Trudy both have very big smiles on their face. Trudy comes around and gives me a big hug, “No one knew, you just told us. Melanie your face has become as expressive as any girl I know.”

Tom the store manager is coming over, Ms. Kendral waved him off. “It’s not store business, and you don’t need to know,” she told him. She goes over to Tom, Trudy is told to take her break, after she finishes checking out Ms Kendral. We both thank her for being so good to us. Then we’re off for fifteen minutes.

“I’m sorry Trude,” we find a spot to exchange a not so little kiss. “I hope I didn’t embarrass you.” I share what I can. Break areas are not conducive to serious conversation. On Trudy’s way to clock back in, Tom says she can have the rest of the night off if she wishes it. Tom signs her card out for the night.


No sooner than I tell her, “Dr. Kylie says my body is developing its own hormones and my breasts are developing on their own.” Trudy lets her hand slide down over my breasts and enjoys my body’s response to her touch.

“I’m sorry Melanie that was rude but it excites me. I’m surprised I did that.” We both go back to Aunt Marti’s house where the girls are all off to bed. Aunt Marti is bringing out Megan to nurse, “Why don’t you get your girls while we enjoy some girl talk.” Trudy comes with me saying she’ll get Sarai and I can get Amanda.

Caring for them has a calming effect and grounds my being Melanie. I am more than a little embarrassed as Marti, Sara and Trudy have a great need to share stories about budding breasts. Sara helps me to discretely as possible to remove my breast forms. My growing breasts seem anti-climatic with Marti nursing Megan across from me. Yet I’m taken with how they appreciate how moving the day has been for me.

Marti invited Trudy to stay overnight with us. It allowed Trudy and me to stay up talking well passed 1:00 a.m. While I’m very tired, I’m too wired with emotions and thoughts to fall asleep. Trudy is not trying to excite me too much or to make-out with me but she is keeping me in Nirvana.

Despite the fact at eighteen, I am looking like a fourteen year old girl; Trudy is treating me as a beautiful woman. “Mel if we’re to be together your sense of beauty has to come from within. I know you’re use to thinking as a dumb boy right now. Knowing how your Aunt, Mom and Sara are endowed; it probably indicates how nicely you might become. But you need to be comfortable being you. Melanie, you’re already pretty but I hope you will grow as a girl in how you measure yourself and look at the world.”

“What do you mean our world?” I’ve turned toward Trudy and could feel her breathe.

“You’re re-entering life as a girl; falling in love with you has pushed me out of my box too. I used to be a stereotypical straight girl. It will be helpful if we don’t have the baggage of looking through old ways of thinking. The world even has many women look at it with a strong male bias. It is hard for a woman to measure up to terms and measurements that aren’t even healthy if we do.”


Its morning as I wake up to Aunt Marti’s voice and the touch of her hand on my shoulder, “Hey sleepy head everyone else is already up. Put on your robe and come to the breakfast table.” I feel embarrassed that Aunt Marti caught me sleeping with Trudy. Except when I look she’s not there. I do a quick inventory before I pull off the sheet.

I take care of necessary things, brush my hair out enough to look okay and make my way to the breakfast table. I forgot my robe but the nightgown is modest so I’m good. Sherry’s cute as she insists on sitting between Trudy and me. “Untie Melwanie, when yu here yu’d nee to gib’me moor ‘tention.”

I look to see her cute smile trying to be a stern face. I give her a hug and confess my guilt. “Sorry Sherry, you are correct I need to love you and Suzi more than I have. But you do know I love you, don’t you?”

“I no’d, but yu’d show moor.” I can tell sharing life with a new sister and their Dad away hurts, makes a big girl’s problems small.

I look to Marti, Trudy is touching her hand. I help Sheri to eat and help feed Suzy. Suzy’s messy plate used to upset my appetite. I help her so it doesn’t wreck Trudy or Sara’s. We have eggs, bacon, fruit, toast, juice and milk. Between Suzi, Sherry and my dolls, my breakfast is more an act of nibbling here and there. I think it helps me from gaining weight. I feel my waist and I’m happy that it is more girl-like.

Trudy shares about the gift card I received from Mrs. Kendral, catching my sister and aunt by great surprise. Marti speaks first, “Wow Melanie, I knew you’ve impressed us but Ms Kendral. That is very nice, I think it says a lot for Mrs. Kendral as well as you.”

Trudy acknowledges, “Yes, she’s taken a liking to Melvin, Melanie. She keeps asking about her coming back to work.”

Sara, “Think of what you might like to buy to make sure you get what you really like and want. Window shop, try a number of things on before you decide what you want to buy.”

“Do you think they will have prom dresses,” I ask?

Marti is now hugging me from behind, “No, I don’t think they do. But buying clothes for a good wardrobe will allow you to put some of your savings toward your prom. Plus Uncle Ron and I will help toward your Prom gown. We thought with all your help to me and the girls, we should help make your prom experience a little extraordinary. We didn’t know if you’d like a gift certificate to Carol’s or for me just to help pay for it wherever you might get. Right now think about using the gift card/”

“It is almost two months away, I have plenty of time to shop for a prom gown.”

“You have a lot to learn as a boy,” says Aunt Marti.

“Girl thinking is her problem,” Trudy interjects. “Melanie, you should be shopping now. You can have fun trying on some you can only dream of buying. But you don’t want to dream too long and see your gown leave with someone else. Plus you need time to select your shoes and lingerie and in our case coordinate with me.”

“Does that mean you asked me to your prom?”


Marti’s phone rang and it became obvious that Mom had called.

Trudy lightly says to me, “You know it would be neat if your Mom and I go prom shopping with you. I remember my Mom with me two years ago. I’m glad we did it together. This is your Mom’s one chance to do it with you.”

I pull a Melvin and yell hoping I’m heard over the phone. “Mom can we go shopping for a prom dress. Trudy wants to go with us.”

Marti looks at me, “You’re Mom says yes, but you’ll need to call her back after our conversation if you are not grounded by your Aunt.”

“Way to go Sis,” Sara pushed me away from the breakfast table. “That is a bad guy habit you have of pushing your way into other people’s conversations. I think the Bridgewater Mall’s New York store is the best one in our area.” Trudy quickly agrees.

“Do you girls evaluate each store and mall?” I ask in jest.

“Sure as well as online buying. Don’t get an attitude about it; you’ll be doing it soon,” Sara says. She teases, “You’ll soon be having your favorite make-up, salon and even panties.”

Trudy giggled, “I think she likes ‘boy shorts for panties, but that might be only while she has that little worm.” I quickly realize teasing like this could become hard to take. I try to attack my sister, but I’m quickly on the floor with Sara and Trudy tickling me. I see Sherry running over and expect she will protect Unt Melwanie. Wrong again, she pounces on my belly as she busts into giggles and tickling me.

“Untie Mewa-nee, yu pantee show’n.”


I am in my room getting dressed so I can take Trudy home to change, when my Smart Phone sounds off. It’s a boy name Travis, another senior from school. “Hi Melanie, this is Travis… I heard that new guy Steven asked you to the prom. I figured if Trudy isn’t a lock for coming with you to our prom, I wanted to call and ask you to come as my date.”

I’m shocked Travis and I have been friends at least since fifth grade. “But you’ve known me as a boy and we’re friends. I think you’re cute and everything but don’t you think it would be odd to be dating as boy and girl?

“I figured if you’re still going as Melanie by the prom you’re seriously girl. I thought back in eighth grade you’d be better as a girl. I’m sorry if this upsets you, but I think you’re a neat girl. If you’re willing to go out with a guy, seriously as a girl I’d like to date you.”

I fall back onto my bed as we talk. Travis has to be 6’ 2” with dirty blonde hair. He just turns eighteen at the end of this month, so he could easily be 6’ 4” or better by the time he quits growing. This is stupid, but just talking to him excites me.

“So what do you think Melanie?” I didn’t know what he just said, how am I to answer.

“Sorry Travis, the phone just broke up what you said, can you say that again.

I hear Sara near my door and wonder how close Trudy is. “Travis, I’m not saying what I’m doing yet, but if you like me why don’t you talk to me at school?”

“I’ve talked to you and you didn’t even blink at me. I even caused you to walk around me or notice me. You walked around me both times.”

“I’m sorry but a number of guys that do that have tried to give me trouble. I won’t promise to date you or anything about the prom. I’d enjoy you being my friend again. That’s how I think it should be first anyway.” I’m back up to finish changing, “Travis, I need to get going, but thanks for calling.”

He said, “I haven’t been to church lately. I’ll plan to go and sit in the balcony if you say you’ll go.” I paused before I finally heard him mutter “Okay.”

“I’m sorry if I hurt your feelings but I need to say, Good-bye till then Travis.”


I pull out a pair of dark rose, crushed velour leggings with a long cream sweater dress. It is a cold day out and this looks feminine and will be warm. I open the bedroom door a crack and as I’m doing my make-up and hair. Trudy’s there to talk. She showers and changes into one of Sara old outfits to get home. I enjoy when she stops a moment to put her arms around me and nuzzled me.

I try the same thing but it is unusual to embrace her and have my breasts come between us. I know I need to get use to it. It’s just a reminder that things are different. I love being Melanie; I’m just not use to me yet. Trudy picks out a necklace and asks me to turn around as she puts it around my neck. It’s something simple, yet nice. I pick an old pinky ring of Sara’s to go with it. Trudy congratulated me on my nice choice.


Trudy drives home and I go with her. Mrs. Brandt greets me warmly, “Melanie, I like the new look; it’s like you’re one of the girls. Trudy says you two are going to shop for your prom gown with your mother. Is she excited to be shopping with her new daughter? Your first time shopping for a prom dress is such a memory. Take your time and make sure you get the right one.”

“Mrs. Brandt, can I ask you, if you’re alright with me going to Trudy’s Prom as another girl?”

She smiled and took me by the hand to the sofa where we sat together. “I must say I wouldn’t have predicted it. For years Trudy talked of her friend and co-worker Melvin. He was special but never a boy friend. Even months ago I would have hoped it wouldn’t happen. Now it would be upsetting if you two didn’t go together.”

“Melanie, I would like you to let me know if you decide to remain a girl the remainder of the year. I would like for Trudy and I to take you out shopping for a new outfit and a girls’ dinner out.”

“I…” I didn’t know how to tell her as I didn’t want to sound like I was after the outfit.

Mrs. Brandt giggles, “I’m sorry, I kind of set you up. Trudy told me it is likely you’ll decide to stay in girl mode if you’re going as Melanie to the Prom. …Now may I pry? Does this mean you’re just crossdressing until the end of the school year? Or are you planning to remain Melanie?”

Trudy has come back into the room. “Mom and I talked last weekend. I said that I thought you might stay as a girl. Mom’s only concern was I didn’t feel guilty for causing this, which I had some.”

“Mrs. Brandt, is it okay if Trudy goes with me and my Mom to begin shopping for my prom gown? Would you be free to come with us?”

Mrs. Brandt lights up, “O that is so nice you asked and it tempts me so much. Alas I’m tied up until 3:00. I would appreciate if you find one, please call me to come see it. I’d be happy to treat the four of us for dinner.”

Trudy pulls me by the arm saying good-bye to her mom.

“Hey girl, what are you doing? You can’t invite someone else out on your mother/daughter time. It is nice enough you invited me along. Plus it will be hard enough for you to select anything with two other women with you.”


“Come on, we’ll have a good hour and a half to shop at New York and Company.” When we got there, I was heading toward the clearance racks to make my money go further. Trudy tugs me over to the spring fashions. “Don’t embarrass Ms Kendral by doing that those things are for winter anyway. You should be able to get two or three nice outfits or dresses.”

A sales woman comes over and asks what sizes and styles we’re looking for. Trudy says 10 and I disagreed with a smile. “No, I’m an eight now.”

Trudy looked me up and down, “Way to go Melanie, congratulations.”

“I’d like to find two good skirt/top combinations and one nice spring dress. Hopefully we’ll be able to get one or two today.”

Gina introduces herself, “Congratulations on your new size, you are very pretty. Would you like to begin with looking at skirts or dresses? Do you have to replace your spring wardrobe because of your change in sizes?”

Looking over to Trudy, “Yes something like that.”

I hear another girl’s voice behind me, “If she has a spring wardrobe to replace…” I turn to see who’s speaking when I hear Trudy speak up.

“Hi Dawn. Melanie this is a friend and classmate Dawn, Dawn you know Melanie, but I don’t think you’ve really met.” I look at the skirts where Gina has stopped. It isn’t a problem to find any that I like, but I cough when I check the price tags.

“They’re 20% off and if you get a second outfit or dress that is 30% off. Let me show you why you’ll want to consider these.” She shows me the lining and stitching around the waist, the matching up of one section to another. I act nonchalant about understanding what she is saying. I remembered hearing this in the past when I tagged along with my Mom or sister; today the importance registers. I have a rose pink skirt as well as a flowered print skirt as I head to the changing room.

I hear Dawn begin to ask what I’m doing. Trudy steps forward handing me a white blouse. Trudy thought and I didn’t. It would be hard trying on skirts and things with a long sweater dress. I model both and Dawn agrees with me. We both lean to the floral print but Trudy holds out a different floral print that she says compliments my coloring.

Dawn is beaming as she and Trudy help me in selecting tops. She’s touched my shoulder feeling my bra strap and took hold of my hand looking meticulously close at my fingers. “Do I pass for a girl,” I ask?

Now she smiles like a little girl caught in the act. “I’m sorry that’s insensitive, but yes you pass amazingly well.” With a delicate touch she traces over one of my eyebrows. “I watched you play baseball against my brother two years ago. I don’t see any trace of that boy save your long eyelashes.” I see her resemblance to Mike Pipers. She says, “I had a crush on you then.”

She holds up a thin blouse in front of me. “You know this would be very pretty on you. You would want a camisole underneath unless you were comfortable people seeing you budding figure.”

Trudy says, “Melanie, she has succeeded in bringing a blush to your face.”

We are walking out after two hours selecting two skirts and four tops. I would have spent the whole gift card except with the discounts and some of my own money I still have some thirty dollars to put toward a dress. I’m pretty sure I saw the dress I’d like to buy. Trudy encouraged me not to rush.


We still reached my parents house with time to spare before shopping with my mom. I go to the refrigerator and pull out a twenty once Dew. Trudy slaps my hand away from opening it. “Do you want to destroy your work in getting down to a size 8?” Trudy looked and pulled out two lemons and poured the water, Mom and Sara keep in the refrig.

I hoped I’d get away with just showing my Mom and Sara what I got, but no I had to model one of my outfits. It isn’t that I mind, but my pattern of thinking is still as a guy. Sara has a new pair of designer jeans and a cami top that she models for us.

Sara asks, “Have you decided which of you is going with the full gown?” I don’t have the foggiest idea of what she’s talking about, but looking to Trudy, I see she understands. Sara explains two full gowns would make it harder to dance and draw close. Sara reminds me of the sleek gown she had last year. It was as beautiful as any other gown and the way it hugged her body and with the slit up one side it was to die for.

Mom hands me my purse, “Come on young lady, I don’t want to hear any comparisons when you’re trying a gown. If you can’t enjoy shopping for your prom dress then you shouldn’t go. And we’re off to shop for my prom dress…

To be continued…

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