Jack and Jill by Trudy - 7 - End or End of the Beginning

Jack and Jill by Trudy
7 - End or End of the Beginning

By Jessica C

Four o’clock in the morning Trudy sneaks into the room and bed with Mel.

I could say, I protested and won or I could make up stories for Monday morning at school neither would be true. We did a lot of kissing and petting but things did not go as far as either wished. It was however more than I have ever done apart from my dreams.

Despite the pill not to get aroused, I did get overwhelmed with feelings and excitement. Trudy said, since I didn’t get aroused like a normal boy, my experience of stars and explosive feelings, must have been a girl’s orgasm. I didn’t know boys could have them. There is not much question in Trudy’s mind. She said it was the first time she had experienced two. I got very excited just holding her as she exploded with joy both times.

Once her mother pokes her head in the door and says, “The the next time I hear noise making its way out of this room Trudy, you will go back to your room and I will sleep in the hall if I need too.” She did not ask if we understood and we were not arguing.

Trudy gives me a kiss and whispers, “Our house isn’t quite like yours.” We began kissing and caressing again. I am not certain when I fell asleep, but it was not anytime soon. I did wake up at 9:00 in the morning in Trudy’s arms with my head snuggled next to her breasts. I set to caressing them until she wakes and there is a knock at the door. We are given thirty minutes to get cleaned up and dressed. I shower and found one of my outfits on the bed. It is closer to an hour before we are ready and out of the room. Breakfast is only a sweet roll and coffee for Trudy and tea, juice and a roll for me.

My Mom and Dad arrive as they haven’t seen much of me. Dad is the only one who knows exactly where the Kendrals live. Mom senses by my behavior that something is different but won’t bring it up.


I am wearing the light blue skirt with two petticoats to dinner at the Kendrals’. Jack has on blue shorts and a short sleeve shirt, knee high white socks and a white floppy hat.

Mrs. Kendral welcomes us into the house saying, “Please call me Rachel while you are here… Charlie thanks for bringing Jack and Jill over to the house. I will call when they need a ride.” She comments, “Jack looks like a cute Dutch boy and Jill you are just darling; isn’t she dear.” Mr. Kendral eats dinner with us and then finds a reason for leaving by 3:30. We enjoy our visit with his wife and their two small children while losing track of time.

We helped clear the table and load the dishwasher. Mrs. Kendral teases, “Jill do you help in the kitchen like this when you’re at home?” She encouraged us to play with the children until she finished all what she needed to do. She asks questions like how I felt wearing girl’s clothes and acting as Jill.

I kind of like it because she sincerely listens to me. Trudy also answers some questions and tells how she has seen me. I wasn’t going to tell Mrs. Kendral but Trudy shares I have been kissed by more than one boy.


Trudy receives a message at 5:30 p.m.: Cousin Staci has invited her to go bowling. Trudy responds: “We need to change, we’ll need to be picked up at 6:30, but lnow, we need to be home 8:30.” I’m taken home with the intention to stay, but Sara greets me with a change of clothes. “Mom and Dad have taken Nana out to dinner and then are taking her back to her home. You are to be home no later than 9:00 p.m.” Sara closes the door saying, “Have a goodtime.”

I check the outfit; it is one of hers a knit blouse and knee length skirt. She includes footies and a change of delicates. Staci picks us up shortly after we have changed at Trudy’s, sharing three boys will bowl with us. Since they are Staci’s friends Trudy assumes correctly they don’t know I’m a boy.

I’m matched with Brett. While he seems to be a nice guy; he likes to hold my hand or hold me around the waist. Come Brett’s first strike in the third frame, he gives me a kiss on my forehead. I respond, “Please don’t do that.” Trudy jests, “Then either give him a hug, or kiss him on the cheek.” I try to kill Trudy with my stare but she laughs if off.

We played two games and the guys play a third game. I see three people from my school leave the bowling alley at 8:00 p.m. I hoped they wouldn’t see me. Brett had atleast eight strikes by then. Brett and I won the second game. Brett gave me a kiss and hug to celebrate. The kiss got a bit involved as he gave a little tongue which I didn’t know how to fight off, despite thinking it was disgusting.

When we get back to Trudy’s, Sara and Mom are there. Mom hands me a bag with a thank you gift in it for Trudy. It is a blouse Trudy liked when we went shopping as well as gift card. Finally, we celebrated the journey as Jack and Jill with a cup of cocoa.

Once we are home, I get undressed and put on my regular boy’s underpants and pajamas. They now feel coarse against my skin and a bit irritating, but I’m determined to wear them. I go back downstairs asking Mom to help take my girl parts off. Dad and Mom smile when they see me, “We’re glad you remembered how to put them on,” jokes my father. “I want Mom’s help to take off my girl parts,” I angrily replied, upset they felt the need to say anything.

Mom says, “I think we should wait until tomorrow night. Remember some school board members will visit the school tomorrow before the meeting. They want to see how students respond to you as Melanie. One of the members asking you to do that is Nancy Parson. I’ve talked to her and I am sure she desires to be constructive about this.”

“Mom, I’m not a Native American or slave; I don’t want to die for someone else’s sins.”

“Well put son and we will back you, even if it means you need to change schools for a year,” my Dad says.

Mom suggests a warm bath to sleep better, she put in a little bubble bath oil. Instead of putting my pajamas back on I change to my nightgown. Mom asks why, when she comes to say goodnight.

“The pajamas aren’t soft, plus I don’t get to be a boy until tomorrow night.”

“You could easily be a boy tonight but that is your choice.”

‘Really, I don’t think so?’

One more morning getting up early, I brush out my hair and put it in a ponytail. I pick a fun dress. It has a print top and solid gold skirt that looks appropriate for fall. I go light on the makeup but highlight my eyelashes and eyebrows.


There are extra adults around the school today, thankfully only one looks like a bull dog, even when he smiles at me. Yuk! Every teacher is surprised to see me as Melanie. Even Sandy appears confused but she talks to me right away and spreads the message. Only a couple of handfuls of students are upset with me, I’m surprised half of them are girls. Sandy passes me a note, “In the dictionary under “’b*h’ It says see them and has their pictures.”

Ms Roberts gives me back my report on “Sense and Sensibility” A+; she whispers “I hope you rubbed off on Melvin.” Ms. Braun calls me into her office to tell me, “New arrangements would need to be made for PE if you continue as Melanie. There are lockers for special situations off of the instructors’ offices,” she says.

After lunch time, Deb and friends herd me into the girls’ restroom to take care of my needs. The need is mostly to wash up and freshen my makeup. I’m going to miss this. We are laughing as we come out. I see Ms. Parsons nearby but can only look away and giggle as I go to history class. I raise the question in class, “Shouldn’t our history be based on achievements, and conflicts within society, instead of wars and boundaries.” The teacher asked possible ways to look at the present, I cite bringing closure to US military presence in conflicts and the inability of Congress and the Administration to serve the country.”

The history teacher asks, “If that would be popular?” Sandy raises her hand, “That’s like the evening news being based on ratings. My dad says he hears and reads more real U.S. news when he travels to Europe on business.” The class has a very active and interesting discussion today.


When I get home Mom suggests “You should lie down and rest. Please make sure you undress and hang up the dress and slip properly. I hope tomorrow you remember how to treat your clothes this well.”

I pinned up my hair and surprisingly rest well. Sara comes in before five and we visit about tonight and the past week. “You know Mel, I am very proud of you. I was afraid you would embarrass me with your joking too much. I’m surprised how good you are at being a girl. It might be nice to have Mel back but I will miss Melanie.” She gives me a hug.

“Thanks Sis, I’m not sure I could have seen it through and appreciated different things without you. I’ve not been as nice a brother as you are a sister. Being my sister is a lot more work than I understood.”

Sara says, “I think you will like this dress for tonight. It should look even better when you are wearing it. If you want to present yourself as a young woman instead of a girl, I suggest you wear my two and half inch sandal heels.” Sara has me try the dress with a pair of flats and I see the difference. I look at Sara’s jewelry before I go downstairs. There is a gold and navy blue bracelet and necklace I think is nice, but I’ll need to check with Mom first.


Mom drives the four of us to the School Administration building and we find our way to the Board room. There are a dozen visitors along with us. Mom hands me a delicate hanky after we sit. I am tapped from behind and it’s Trudy and her mother. Eight of the nine school board members are present with four of them being women. There is the Superintendent, Principal Lawrence, a man Dad says is the school lawyer, a secretary and a treasurer present, and I’m not quite sure who is who.

The meeting is called to order, and though we are not going to be sworn in formally, we are asked at the beginning: “Do all present agree as you speak that you will be respectful and that what you say will be true?” I believe all responded saying “I will.”

It is after 7:00 p.m. before my situation is brought up. The Courier News article as well as the town newspaper, several radio broadcasts, Fox News and CNN and two comedy programs are mentioned. Principal Lawrence continues to speak. “The newspaper reporter confirmed for me that Melvin Greene issued a challenge stating ‘the school board’ would not take it up, about him presenting himself as a pregnant girl. Melvin told me even a two week time period would be too easy and too short of a time to learn from. When I asked him what might be a meaningful challenge? He responded, ‘My Aunt Marti is due to have her baby in February and if I could shadow in her footsteps that would make a meaningful report.’” He closed by saying, “Melvin agreed to cooperate with the school board and abide by your decision.”

I’m asked to step forward with my parents, Sara and Trudy want to be next to me but they are asked to wait. President Bennett asks, “Mr. Greene do you agree with what Mr. Lawrence has said?”

“I disagree with the reporter, she is the one who issued the challenge to which I said I didn’t think you the board would allow it. I did not mean anything derogatory toward the school board but that a public challenge like that is not wise.”

One Board member spoke up, “We agree that a public challenge like that is not wise, but along with the reporter several people confirm her story was what you said to her.”

I tell them, “I’m sorry about that but still respectfully disagree.”

“Do you acknowledge that you agreed to continue as Melanie Greene wearing the pregnancy harness with increasing weights through your Aunt’s pregnancy and until her new child is born?” I went white went white as a ghost and had to sit down.

“No, it was not my intention to continue as Melanie, but by shadowing my Aunt Marti: I meant to be with her as best as I could. She is special to me and I am sure she would not mind me being there to help as I could. I know there are personal times I would not be privilege to see.”

“Again Melvin, Mr. Lawrence, Ms. Braun on two occasions and at least one teacher heard you confirm the agreement as stated here. We are not so troubled by those statements, because you have behaved quite well during this time and have done even better in school than you usually do. You seem to enjoy the attention, especially the attention shown to you by the female students.”

Mr. Bennett asked, “How did you plan to wear the pregnancy harness as it expands without wearing women’s clothing for the pregnancy? I do not know of such clothing for a young man like you.”

Mel said, “I guess I did not think that through and can see how you might jump to the other conclusions.”

Nancy Parsons, “Mr. Greene do you understand what it means that we have worked hard to be a gender friendly school? Some students have taken to heart your experience this past week and have seen many of your actions to be very sensitive of them. Your reneging upon your challenge would be seen as self serving and a slap to them.”

She continues, “I would like to ask special privilege to speak to you and you parents for a few minutes. And then I would give the microphone to Mr. Henry upon our return.”

“Privilege granted, ten minutes be granted,” says Mr. Bennett.


Ms. Parsons waves us over, “Melanie, and Mr. and Mrs. Greene, I believe I come as your friend even though it may not seem like that right now. Circumstances had me picking up my daughter at a bowling alley last night where I believe I saw Melanie with a date and in fact hugging him; and then today after lunch I was near the girls’ bathroom and you as Melanie with several friends came out of that bathroom giggling as girls might.”

“Your actions seemed more appropriate for a T-girl which is not a disparaging thing. I know you deny being one and that is a decision and identity that only you can appropriately give yourself. Your Aunt Marti agrees that you two are close. She believes with her husband being gone in military service; you two could benefit each other quite well. It is my intention not to bring up this information about your date or very girl like behavior. But Mr. Henry will motion that we accept your challenge but leave it open through the end of the school year if you would find that helpful.”

I speak next, “Ms. Parsons, you are considered friends to our family and you know from my family that our word is important. I am not lying that I heard and understood things differently. I don’t want to do this; my dad even said I could change schools if need be. But if I will agree to it but I will need the support of some professional. Because I don’t think this will be easy on me.”

Finally I said, “You did not ask Trudy Brandt, about the time with the reporter or the incident last night. You are right there have been times as Melanie, I naturally acted like a regular girl and I have no explanation.” There’s a knock on the door and we’re to go back to the meeting. The school board officially accepts my challenge with a report qualifying as an independent study under the auspices of the Community College.


Sara, Mom and Dad surround Trudy and me with Aunt Marti walking over to us. Aunt Marti has a smirk that she is trying to hold back. Marti said, “You might be a bit disappointed but with Ronnie deployed overseas; I’m glad you will be with me. When one door closes another door opens.”

Mom asks, “Marti can go with us to your doctor tomorrow or Wednesday after school?”

Aunt Marti looks to me, “Melanie is there a day you don’t work?”

That’s nice Marti asks about me; “Thanks, but it is Thursday when I don’t work. I don’t know if Mom’s willing to wait that long?”

“You will have to adjust your schedule sometimes, like I am sensitive to you. I don’t think your mother won’t mind waiting one more day; since she’s going to have her daughter for another three to four months.”


We go home to get some privacy and to let things sink in. I am holding Sherri and Aunt Marti holds the baby. Marti is thinking of something but is being quiet until I ask, “You seem to have something on your mind?”

“I don’t know if I should, it is a little quick,” Marti said?

I ask, “Well, I might as well think about things I need to consider?”

Marti smiles in response, “Well I think it might be nice if you came to live with me. I will be going to Lamaze classes soon. I would like you to be there for me as well? You would only be a few blocks from school and your friend Sandy lives at this end of next block.”

The doorbell rings and it’s a pizza delivery. When we go back to the kitchen there is a bottle of pickles on the table. Mom said “Very funny everyone, but I don’t think this will apply to Melanie.”

Trudy eats and then leaves saying she will see me tomorrow at work. Trudy talked to Mom, Aunt Marti and Sara before she leaves. “I just wanted to assure everyone Jack won’t leave Jill holding all the responsibilities alone.” Everyone including me giggles.


I wake just before my alarm as the routine has set in. I shower shampooing and conditioning my hair. It is getting easier to brush out and keep its style. My makeup is light with the exception of setting my eyes off a little more. Sara says, “It is well within good taste.” I like the long sleeves on the mini-dress and thought while it is not tight it molds to your shape.

Down at breakfast, Mom and Sara both suggest I wear an outfit with a loose blouse and separate skirt. I like how I look, plus as a guy I am not into changing my clothes just because someone says so. I did go to Sara’s closet to find another pair of 2” heel shoes that will look good. Sara looks and finds a beige open toe shoe that goes nicely with what I am wearing.

I didn’t get all my homework done which is a bit disturbing. Melvin wouldn’t have been worried at all. Sara wants to get to school early.

Ms. Braun greets me soon after I am in school. “We should go to the nurse’s office to get things set up.” I can see she is also amused with my dress. “You are very attractive this morning Melanie.” There is a nurse from a clinic in town to help us get things started this morning.

I meet the nurse, “Hi, I’m Nurse Heidi, Melanie. I work at the clinic your Aunt Marti goes to and I’m to help set you up with your first baby bump. Unfortunately you will need to strip town to your panties and bra. I would have thought someone would have encouraged you to wear something else, though this is very pretty on you.”

In a small voice I admit, “They did, but I didn’t pay attention to my mom or sister.”

“Well it’s a good idea for us girls to listen to one another, but I guess that will be part of your learning,” she holds a giggle under her breath. Heidi, “I am going to just glue this very small bump on you. It should hold till next Monday when we start using a little more weight and maybe the pregnancy harness.”

I slip my dress back on and Heidi helps to zip it up. I give her a small hug as I say thanks. She wishes me a good day. It is all quick enough that I get to homeroom. Classmates are amused by my remaining as Melanie. They are told by the teacher, “Our new student will be addressed as Melanie Greene until her project is over.”

The changes will to include Gym switching me to a physical education class with girls and me using one of the private individual locker rooms. I have the choice of Senior Health for girls or Home Economics. I am planning on Home Economics, as senior girls say I won’t like what they would do to me if I take Senior Health. “No, it is not a threat; it is a promise,” so I’m told.

Practice in chorus goes well and Mr. Larkin is happy to have me through the winter holidays concert. He even plans a duet with me backing my sister for a holiday tune.

Sandy did not show any special interest in me until she asks me to sit during lunch with her friends. She asks me, “Are you willing to double date? Lisa in our class says she is willing if you would like to go out with a girl sometime. Trent a senior would like to ask you out but I am not sure where he is coming from. I am sure I can arrange other dates if I know you are interested. Or will you be going out only with Trudy?”


I’m interested in seeing Trudy at work tonight. I have text messages from Trudy and Mrs. Kendral about work. Trudy wants to know if I want a ride which I do. Ms. Kendral says, she is happy I cooperated with the school board, her note says, “Your employment in the bakery department should go well. If there are any problems at the store, I will be very supportive of you.”

Trudy is happy to see me but lets me know I am now a girlfriend, not a boyfriend. She does ask me to go to a dance with her and some other girls Friday after work. I am accepted as another one of the female employees at work. It is no longer special to others and I am not getting as much special attention.

Things go smoothly until Thursday afternoon and my visit to Dr. C. Adair at the University GYN-OB Clinic. Heidi welcomes me and takes me to an exam cubical and I change into a pink wrap. It is none too long nor designed for modesty. Once I have changed Aunt Marti is allowed back in with me.

Dr. Connie Adair is thirty-something and she has a nice disposition. She gives me an exam and wants to inject a tiny capsule under my skin. She says, “This will last two weeks and give you a mild experience many women have early term.” She truthfully says, “It is not necessarily a fun experience.” To her surprise I agree. She needs to talk to my mother to get her to sign with me.

Dr. Adair also asks, “Are you willing to move in and live with your Aunt Marti during the remainder of her pregnancy.” Besides an upcoming Lamaze class, the most important thing I am to do is just keep her company.

“Yes,” I also agree to help do half the wash, wash dishes and some house work.


Things go well come Friday morning both at school and work. It is different this time going to a dance with Trudy after the fall concert. Trudy and other girls dance with me as many of the guys are standing away from me. Two horny guys dance with me during the night and Trudy says, “It is no less gross for the average girl. There are two guys that cause me to feel differently. Jeff and I visit a little, he says, “I know you’re another guy, but I would be interested in taking you out sometime. I hope it will get me over the fear of dating girls.”

Morning finds me near the toilet as morning sickness has set in. If I could just stay close to this porcelain doll it would be better, instead, it just pushes back my moving to Marti’s until after lunch. When baby Suzie wakes, it is my first experience of Marti nursing her baby with me there. It is a beautiful sight but not in a traditional guy way of thinking.

The evening is simple: a Walt Disney movie for Sherri with popcorn. Marti nurses during the movie and I change Suzie’s diaper and put a sleeper on her for the night. Suzie will be a little over thirteen months when the next baby is born. Marti tells me, “Ron and I thought, it would be a safe time to have sex without birth control.” She tells me, “You can see we were wrong.” I want to say it is too much information for her nephew to know.


Before I go to sleep I get a text from Trudy, “If it is okay to call now please let me know or you call me please.” I call her to find out what is up. “Melanie, I don’t know how to tell you this; I’m a little afraid. I find I like you in a different way than before.”

I ask her, “I’m happy but not quite sure what you mean?”

She said, “I know, but please don’t laugh. You know we can usually talk about everything, this might be different.”

Assuming that she now likes me more as someone special I remark, “I love you too; I just hope it won’t get in the way of our friendship.” With a little more girl talk we say goodnight and it takes some time for me to get asleep.


Sunday, Marti takes me shopping; to my surprise most of it is clothing for me. Another surprise is my sleepwear is different as a younger woman helps pick it out instead of my mother. She tells me, “I can’t officially tell you but you might enjoy using some of my pre-natal vitamins.” I didn’t think I would but I did try one come Sunday night.

Sherry asks, “Unt-tie Melwannie, can you carry mwe?” I carry Sherri when I’m not pushing them both in the stroller.

When we get home I get to model everything for her, her mother and my mother. I get upset at Mom taking pictures but I am overruled. Come time to go to bed, I knock and go into Marti’s room as she has asked.

Marti is visibly pregnant but nowhere like she was last year at this time with Suzie. We sit on the edge of the bed talking. She had just visited with Ron via the computer. She’s missing him, but tells me how thankful she is that I am here. “I am talking to you more like a niece. While that might feel awkward, I greatly appreciate doing so. You and I have always been close; I think these past two weeks you have grown quite a bit.”

I tell her about my dancing with Jeff and his interest in dating me. She giggles at the thought, “I hope you won’t be surprised when the idea looks even more attractive to you.” She elaborates, “Being tucked away with a baby and a little girl, you will find it nice to go out with someone. You will probably even enjoy him showing you a nice time. Since you are living as Melanie; dancing with him and going on a date could be fun. Just remember this doesn’t commit you to anything and doesn’t mean you are gay or wanting to be a girl long term.”


Back in my room, I’m drifting to sleep, when my phone rings, it is Sara, “Hey Sis, Mom says you got some more girl clothes.” We drift into girl talk and it truly is a sister time. Our phone conversation ends after forty minutes only because Trudy and Sandy have called. I call Trudy back as I will see Sandy in school. It is midnight before we finish talking. “Have a happy third week Melanie.” I hear a kiss at the other end and I kiss back. “It is not one girl to another to me but I hear Trudy, “I love you Melanie.”

To be continued…

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