Jack and Jill by Trudy - 6 - Halloween Dance

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Jack and Jill by Trudy
Halloween Dance - 6

By Jessica C

Come morning, I am up early and getting ready and I put on the red dress before I go to breakfast. I notice part of the slit on the side has been hand sewn shut. “Mom, why did you sew up the side on the dress? I appreciate it but why?”

“Your skirts can’t open more than 3” for school and I didn’t want you to be sent home. But I am surprised you are wearing it to school; I thought you would just wear it to the dance tonight.” She smiled, “I think we can open it for tonight’s dance.” I’m surprised about not having to wear it to school, I thought that was what they wanted. I was going to change but Mom and Sara say I don’t have time.


Sara drives me to school early. Mr. Larkin our vocal teacher smiles, when he sees me. Though I am not sure why.

Ms. Roberts compliments me, “I am glad you showed some restraint in choosing your little red dress Mel.”

“Thank you.” She calls me to a corner and asks for my brush. She uses it to fix my bangs which were blown about.

Sandy tells me, “Mr. Lawrence has told us today you need to use the restroom in the nurse’s office.” That means I need to think before I go up to the third floor for classes just in case I would have an emergency.

As we’re passing through the halls for my first class, Ms. Braun makes it official. “Mel, you are to use only the toilet in the nurse’s office… I want to see you in my office as soon as you finish your lunch, make sure you remember that.”

I receive many compliments on how I looked last night at the parade and work. However I receive several notes placed in my locker calling me derogatory names, with one even asking for sex, no name given. Just before lunch I am pushed into a locker and trip to the floor. The hallway is busy so I am not sure if it is an accident or on purpose.

I check the dress and I am glad it didn’t tear. My pantyhose was messed a little with dust and two small snags that I hardly noticed. John my classmate from work gives me a hand in getting up and collecting my computer, purse and books. He says, “I have a lot more respect for you now then when this started. I’m even feeling bad about others who get hassled every day.”

“Thanks John, I appreciate that. I know what you mean about the others.”

Come lunch I am invited to several tables for lunch. I didn’t have the nerve to sit with my friend Eddy who came out last year. He’s a friend but I don’t want to share his labels. Instead I sit again with Sandy, Deb and friends. I eat quickly and go to Ms. Braun’s office.

“Hello Melanie, I hope you don’t mind but I have been told to call you Melanie when you are dressed as a girl. I have been asked to confirm that you told Mr. Lawrence and others that you will cooperate with the School Board when you meet with them Monday. I want to remind you they will meet at 6:30 at the Administration building.” She pauses and smiles, waiting for me to respond.

“Yes, I agreed with Mr. Lawrence, and have told my parents so. I will cooperate and abide by their decision. My parents are going to attend with me. I have been told that is okay.”

Mrs. Braun talks with me making sure I have the support I need as well as making sure I am freely deciding what I’m doing. I try hard to communicate, “I am in no way seeking to cause trouble. I have learned a lot and I am sure there is more I could learn through Aunt Marti.”

My visit with Ms Braun goes on into the next period. I feel much better now having her support. She takes the notes I found in my locker and she voices concern about my falling and what might have happened. She suggests, “Please take my extra pair of pantyhose as a gift. Sorry but those little snags and where it is stretched is a bigger deal for girls than you realize. You should learn that if you are going to be Melanie.”

I said, “But it’s not the girls who have it wrong, its guys who are wrong. We don’t pay attention to that small stuff.” She walks with me to History class and asks the teacher to excuse my lateness.

The next period, I have Chorus instead of gym and Mr. Larkin informs me, “I now expect you to be singing with the girls as part of their chorus group for the Variety Show. I want you to even practice as such for Thanksgiving and our Winter Holidays Concert.” I practiced today and will do so next week though I don’t expect to be dressed as Melanie.

I joke that I will even dress as Melanie for the Thanksgiving program knowing we did not have one. Deb tells me afterward, “But we do, we sing at the Elementary and Middle schools for Thanksgiving as well as at the Rotary Club and the girls chorus even sings for the Festival of Lights. You will want a good pair of tights and a long skirt for the Festival of Lights.”


My phone buzzes with a text message from Mom: “You and Trudy have a 4:00 p.m. appointment to have your nails done. I’ve even scheduled facials.” While it will be enjoyable I am tired of rushing here and there like a girl. I will be glad for things to be over tomorrow night.

Sara gives me a quick ride home where Mom tells me to change out of my dress and pantyhose. Mom tells me, “A girl doesn’t wear her dress the whole day if she can help it. Your dress should air out a bit plus I need to take out the threads I added this morning.

I wore floppy sandals to get my pedicure along with my fingers done. Mom comments on how much my hair and complexion has changed the past week. I checked with my compact mirror and had to agree. My complexion isn’t showing blemishes like last week. There is a healthy glow to my face.

Teshi takes me at Colors Nail Salon and again Trudy is next to me. While I enjoy having my feet and hands done, I am visiting with Trudy and not watching every move like before. Teshi explains to me, “The red polish matches your dress, but it is neither florescent nor too bright like the ones you chose.” Teshi explains, “Tonight your nail polish should compliment your dress while not taking the boys eyes off of you.” My lips are luscious even with them painted a shade darker with a dark Bing Cherry Red. Trudy smiles as she notices my legs pressed together. I am afraid what might happen when I stand up. The appearance of my feet and legs has improved even more than my complexion.

Trudy agrees pay towards her portion of the bill with a little for the tip, which leaves me with enough to consider a small ruby pinky ring that I see and try on. I didn’t intend to buy it but I did. Trudy buys a turquoise ring. “It is more fitting for Jack,” she tells me. I don’t know why I bought my ring, but I know Trudy is only fooling herself if she thinks she bought it for Jack.”


Trudy com

es home with us to change for the dance. She’s covered her outfit so I can’t see it before hand. Sara greets her at the door and they go up to her room to change and I am relegated back to my room. I put on the concealer and foundation and then get dressed. My pantyhose are a more expensive brand that I haven’t ever heard of it. Mom helps me put them on. Mom gives me a small glass of water and a pill. I ask, “What is this?”

“It is so peter doesn’t spoil your night,” there’s a light giggle. Mom has another bra like the one I had on and wants me to change into it, “It will help as the night goes on to have on fresh under clothing.” Mom sprays a small mist of a gardenia fragrance, “I want you to walk into this.” It is beautiful enough that I want to use more of it, but Mom won’t let me. “Don’t worry, it will stay with you all evening, too much Gardenia can be overwhelming.”

Somehow the little red dress sliding down my body feels even more wonderful than this morning. I didn’t notice, until it is on but the slit opening on the dress and the slip line up nicely. “Mom look how amazing my legs look?” I go looking for my sandal heels, when Mom hands me another shoe box. It is a very beautiful pair of three inch heels with open toes. I don’t realize until I stand the difference of another ½”. “But Mom won’t my feet tire faster in regular heels.”

“Yes, enjoy the look and also remember how it feels. You’ve noticed how pretty your legs are, now enjoy the night with Trudy.”

“Mom, I can’t believe you said that?” Mom giggles and then sends me downstairs to wait for Trudy, and as I pass Sara’s room the door is open a crack and I see Trudy from behind. She is still in her panty and bra. I swear under my breath as I see her curves, ‘I wish that were me. What am I thinking?’ I mutter aloud, “I am glad tomorrow is the last time.”

“You still have the dinner at Kendrals’ and the meeting before the school board on Monday” my mother says, “so I hear. “

Once downstairs Nana hands Mom a long jewelry box and she takes out a gold chain with a ruby in a teardrop setting. Nan hands me a tissue and encourages me not to cry. Nana takes a picture of me and another one of me with my parents. The doorbell rings and Aunt Marti comes in with her baby and Sherri her three year old. I bend down and lift up Sherri. “Mommy says, I am to call you Auuntie Melwanie.”

I smile and say, “That sounds very good, do you know who I really am?”

She repeats my name, “Auunt Melwanie”. Aunt Marti says, “You know Ms Melanie, you could make some good money babysitting, especially if the daddys pay you.” “Gross, Aunt Marti, how can you say that?”

I am sitting when Trudy appears at the top of the stairs. I stand and look up to her. She has on a long black dress but the skirt is fashioned like a beautiful evening dress in a pants style that is hard to it as recognize as such. There are atleast three cameras clicking taking pictures. I look behind me and even Trudy’s Mom is here. Dad is standing behind me with his hands on the sides of my shoulders. “You have a most beautiful date Mel.” “Thanks Dad.”

I have a wrist corsage of baby breath and white baby roses. Dad hands me a red rose for Trudy’s lapel.


The dance is already well attended when we arrive, but as we walk in with me holding Trudy’s arm the room goes quiet. The band starts an old Beach Boys song “Little Surfer, Little Girl”. Trudy takes me in her arm to the dance floor and then in both her arms as we dance onto the floor and others follow.

“Trudy you are so beautiful tonight. I want to thank you for coming tonight and for making the whole week special.” I continue, “Every night has been better than the night before and tomorrow we have one more night. Do you really think it can be any better?”

“It will be for me as we will be at my school. Even if it is only just half as good, it will be well worth it.” Trudy leads me into a full spin and then leans me gracefully back. It is but a second that I am on both heels. We have three more dances before we sit down.

“Trudy, I will make every effort for tomorrow be as special for you as tonight is for me!”


I am seated for one dance when three guys come over to me. There is no question for me who has the next dance as Derek makes an impressive entrance as Frankenstein. The first song is slow but the second is comical, “The Monster Mash”. I’m not sure how to dance to it but I follow Derek’s lead. Seemingly he has choreographed the song. The whole dance floor is either acting up or trying to follow Derek and me. The song ends with Derek picking me up and carrying me out to the hallway. I am laughing so hard I am not sure if my panty is showing. As Derek puts me down he leans me back and gives me a kiss. My breath is taken away. It is not until later I realize I should have been more embarrassed.

As I went back into the dance the other boys want to dance with Jill or Jack. Jack tells them, “You will need to sandwich yourselves in between our own dances. Come 10:30 I have danced with two more boys between dances with Trudy. The last one had stepped on my feet and let go after he twirled me. I fell on the floor. He was even a klutz when he tried to help me up. I begged mercy before the dance ended.

Trudy took me into the womyn’s rest room to stop the approach of the next guy. I’m the only guy in the restroom but everyone treats me as another girl. Then another boy came into the rest room. He makes the mistake of dropping his skirt and panties in his stall and then tried to peek to see the girls. Tracy pulled his skirt out and his panties came with them. They gave him his panties back wet and they coaxed him to open his door, as I left.

Trudy wanted to stay but she came out with me. There are different stories about what happens next.

Come 11:15, Trudy gets me up dancing again, two dances with her and one dance with a guy. Derek taps me on the shoulder but when I turn around it is Princess Leia that is there and I am happy to dance with him. I ask, “Is your brother as protective of you as he is of me?” I find myself leading for the first time since one of my first dances with Trudy. Travis is his name; he wishes it were Stacy. When I hope others aren’t looking I give her a kiss.


It is 11:30 when we leave the dance as it would end minutes before midnight and some had already left. My phone vibrates with a text message from Mom: “You have until 1:30 until you need to be home. You need to be a good girl or come home earlier.”

We walked around a little outside at a nearby park, but go to my house since the night is getting colder. My parents usually let Sara alone in our rec room. We have a pool table, some comfortable chairs where we can play our music. It is funny as Sara already beat us down there, but we find our own place anyway. Trudy’s more aggressive than me but I enjoy her hands going over by buns as she calls them. The material of the skirt, my panties and pantyhose make for an interesting feel. Trudy feels even better to me.

My boy equipment finally begins to respond when Mom calls down that Trudy and Bart need to go home.


Sara and I hang up our clothes and get ready for bed. Sara gives me one of her extra robes so we can go down and visit. It looks very pretty, but it doesn’t cover a whole lot. Mom smiles and pours some tea so we can visit.

Mom hands me a message from Principal Lawrence: “You are requested to wear a dress and come as Melanie to school Monday. Some school board members plan to visit school and want to see the students reacting while you are attending as Melanie.” I’m too tired to argue. It is three o’clock by the time I am in bed and I sleep until noon.

Aunt Marti brings over a bridal gown though it is not hers. It is a simpler and shorter bridal dress than those traditionally worn. I don’t get to try it all on because I am to get dressed at Trudy’s house. Mrs. Brandt wants the joy of helping me to get ready. The dress is snug and there would be a surprise there that I did not see.


It is three o’clock when Mom drives me over to their house and then leaves me. I am sure she will be back. I wished she had stayed as I am anxious about changing around Mrs. Brandt. I guess I have a good right to be as she came into the bathroom while I am in the shower to make sure I shave my legs and underarms. I didn’t satisfy her she said and I had a second chance to do better or else.

Mrs. Brandt is some six years younger than my mother and has a very well endowed figure. Mrs. Brandt has a piece of clothing I haven’t seen before she says it is a corset. Her sister Irene is there officially to help make sure I am not harmed or abused. They lay me down and put a vagina gaff on me and then a small pair of lace panties. When they help me with the corset and finally tighten the corset. I jokingly tell her sister in a squeaky voice, “You didn’t do your job.”

I am more impressed with the lace sleeves of the gown as I can see and feel them. I said they are too girly. I’m told this is Trudy’s night and I am to dress accordingly. Next they style and fix my hair and face to be as pretty as a bride. I am not sure how they do my makeup but I now I look so delicate and my hair so eloquent; I just enjoy what they did.

This afternoon Trudy is done first and does not worry about seeing the bride early. She has a short lace dress, black panties and black lace stockings and a white shirt collar and glittering tie to give the illusion of a tux.

The combination: of having my hair done, the vagina and seeing Trudy; I’m getting too excited and mess my panties. It is really embarrassing as her Mom helps to clean me up. I am given another small pill and a small glass of water.

They have me step back into my bridal dress just prior to the final fixing of my hair. I am wearing a small tiara with a short veil with a train that touches the back of my knees. Once again pictures are taken and quickly transposed to wedding announcements that we are to take with us in our purses.

We have a light meal and a half hour later I am told to go to the bathroom on my own. While I finally managed, it should go faster the next time. It took me a half hour to do what I needed to do and become presentable again.


Luckily the night is mild as there is a procession on one floor of the school before we can go into the dance. I am not a happy camper when we are approached by the Courier News reporter. Trudy reminds me to act nice as making a scene here would be bad if it got back to my school.

Despite that temporary ripple of my emotions, the night soon turns festive. Tonight I have two monsters to put up with one Frankenstein of course; the other is King Kong. The girls at Trudy’s school are the ones who take most of the turns dancing with me when Trudy is not. Most of the times as fast dances but the girls take the opportunity during slow dances to lead. Two guys who did get to dance with me both got excited during the dances.

Tonight we leave the dance at 11:00 and go for a walk. Trudy has a suit coat she lets me wear as we walk. We talk about the past week sharing the times we enjoyed the most. She as well as I enjoy each other the most and found our times with children, babies and moms to be very special as well. Trudy says, “You would make a great girl and mother.” It is midnight when we stop walking and 12:30 a.m. ride back to Trudy’s house.

I am now so tired I don’t fight the news I am to stay. It is decided I will stay in the guest room. I am provided a nightgown to wear and the bed has a fluffy comforter that promises to keep me warm. Mrs. Brandt says she does not have the dissolving glue agent for my gaff. I am not sure it is true, but again I’m too tired to argue.

To be continued…

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