Jack and Jill by Trudy - 15 - Looking At the Future

Printer-friendly version


Audience Rating: 



Character Age: 

TG Elements: 

TG Themes: 

Other Keywords: 


Jack and Jill, by Trudy
15 - Looking At the Future

By Jessica C

Melvin thought it was weird to be Jill for Halloween...
But his friend Trudy liked it and that made it okay...
A dare to act as a pregnant girl was credited to Mel,
Acting as that pregnant student is Melanie’s roll into February…

There will only be two more days of filling my breastforms so the girls can nurse. A funny thing with nothing to activate and cause the babies to cry, I could technically sleep the whole night through. But again tonight I wake at 3:30 a.m., first I check Allyson and open my nightgown to nurse her. It has become a time of solitude in a busy world. I find I am more reflective now and I’ve come to treasure times like this.

I am glad the babies are in my room and what Sandy and I have done to prepare for Marti’s baby. It is like the nursery is brighter, anticipating a baby who will coo as well as cry. I look forward to giving Aunt Marti my primary attention. ‘But will I cling to my babies for awhile; how long before I willingly return them to the hospital. I am sure I can fain distraction while Marti is in the hospital or miss my next appointment with Dr. Kylie. It really isn’t so much the babies as I am holding onto Melanie through them. Crazy as it seems to the thinking of Melvin, how can I tell anyone I want to be Melanie that I like being a girl?’

I changed Allyson and put her back into the toy crib and have Sarai to nurse. I can imagine a smile as she nurses and the pride I have as a mother. I continue to contemplate: ‘I feel a bit guilty, but I love Trudy in a different way being Melanie. Melanie even loves her more than boys. I kinda wish I continued to sneak pills. Lord knows I have enough as some girls have given me some of theirs and other girls have said they’re willing too if I want them.’

I hear Aunt Marti is up waddling her way to relieve her bladder; oops she’s in the hallway and will likely see my light under the door. Sure enough she opens my door a crack. “I thought you might be getting up at night to nurse your babies. Surely you make a very good mother and I’m lucky to have you watching over me. I want to thank you and Sandy again for setting up the nursery, it all looks beautiful and ready for the baby. The bassinet Sara and you bought is darling; it is like one I wanted to buy when I first had Sherry.”

Aunt Marti sits on my bed and we talk. “Your Mom and I think this one is another girl. I know Ronnie and the Grandparents all want a boy to carry on the family name. I’d love a little boy as well”

I tell Marti, “Your daughters will have to find a husband willing to take their family name; someone said marriage certificates indicate it is possible for the man to change his name.” Marti smiles, “I wouldn’t be surprised that a daughter of mine would be strong enough to get that done, but I’m not interested in marrying them off right now.” Marti giggles, “Would you be willing to change your name for Trudy.” I blush and Marti giggles even louder. “You know she is quite smitten with you?”

“Yes, I’m afraid more so with Melanie than with Melvin.”

“Yes, you will be going back to Melvin soon. I was hoping to see Melanie shopping for a Prom dress with her sister.” My expression changes with the thought of being Melvin, opposed Melanie. Aunt Marti doesn’t say anything even though she noticed my eyes perk up at the idea. “I better get my sleep as I will need my rest for when the baby comes. Plus, I shouldn’t confuse your head with silly ideas.”

“Aunt Marti, if I stay here to help you after the baby comes, even delay going back to being Melvin; would you help me to go to a prom with Trudy dressed as a girl?”

“Woe, Dr. Kylie already told you, you need to go back to being Melvin before too long. Anyway what do you think Trudy would say about that?”

“Trudy and I are stronger friends now, but I’m afraid Melanie is the one she feels a deeper affection for. And even if she wouldn’t go with me, Travis and Nate have already asked if I would go with them.”

“Oh”, Marti hugs me with some concern, “you need to put Sarai to rest and then get some yourself please.” I did fall back to sleep, but it’s a restless sleep.


I’m happy that some of the baby bump is gone, much of the weight; but I didn’t realize changing back took time and the woman’s body didn’t just snap back like it was before. My skirts still needed to be bigger than normal; it looks more like I am out of shape. My tops need to be bigger around my bust; Sandy and Sharon say I looked like Dolly’s little sister. Friday after school I have my last appointment with Dr. Kylie. It would be the first time I don’t bring the babies.

Dr. Kylie gets upset, “Melanie, you have been very good and there is no way this is an accident that you did not bring them.” ‘Me?’ “Yes, both Mel and Melanie have been much too good and responsible. I suspect this is the prankster school officials weren’t use to believing.” I froze and stared into space thinking about what Dr. Kylie said.

“Marti,” Kylie was speaking to her, “how have her grades been through all of this?”

Aunt Marti perked up with her response, “Melanie finished the first half of the year quite strongly. Mrs. Crowley, her advanced composition teacher called this week; she was checking whether I knew if Melanie might have someone writing her papers for her. I assured her that I too am impressed with her papers, and I proofread them. I have seen the research she does before she begins to write.”

“You didn’t tell me that Aunt Marti? Mrs. Crowley even congratulated me yesterday on the paper I got back.”

Dr. Kylie said, “This is why I don’t want that prankster part of you to go back to ruling your life. You need to learn how to let your hair down without going overboard.”

“What can I do to still feel like a mother a little bit longer, if I bring the babies back? The school said I was to continue a little while after Aunt Marti’s baby came”

Dr. Kylie looks serious as she says, “Don’t tell me you have the babies down in the car.” I smile, “No, Aunt Marti told me that would not go over well. But I can get a ride here from one of the girls at school and have them here tomorrow. Are you going to answer my question?” Tomorrow is a school day.

Dr. Kylie thought for a moment, “I suggest you buy some dolls that you can keep and enjoy. This experience will be with you for years to come, two baby size dolls could be a helpful reminder.” Dr. Kylie sat me down as she felt the need to remind me: “Remember, I want you to get back to being Melvin. If you still want to do something when school ends we can talk about it then.”

It feels like she used a shotgun to blow holes in my sails. The rest of the day is spoiled. Even Sandy and Trudy calling didn’t change things.


With a goodnight’s rest I’m back to being myself, ha, being Melanie. Marti wakes me, “Hey Melanie, if you want to go shopping, you’ll need to get up and get some things done first.”

“Why can’t I just sleep in? I should get some regular girl time.” No, this isn’t my first time with an attitude. Since the New Year started, Aunt Marti’s seen it half a dozen times. Aunt Marti throws me a bag; I grab what’s inside and pull it until I recognize Melvin’s clothes. “I get your point that it’s cold.” I look to Marti and both of us are hurting. I’m quickly up and giving her a hug, “I’m sorry Aunt Marti”

‘I’m sorry too. I thought I’ve been giving you ample time, but I’m going to need you more not less.”

“Are you okay Aunt Marti? Do you need me here? I’m sorry that I got my panties twisted in a knot.” Aunt Marti laughs and Sherry comes running into the room. “Mommy you okay, Untee Melwanie you be good.” Next it’s Suzi crying.

“Aunt Marti, do you want me to get breakfast or Suzi?” I mix up some pancake batter, start some sausage and get out the orange juice. Marti already has the coffee brewing. I’m not sure how Sherry got her, but she is carrying Sarai into the kitchen. Luckily it is not a real baby. Marti gets into the kitchen with Suzy to see the last of Sheri handing me the baby. We both lightly giggle knowing she sees Sarai as a baby doll.

Marti plunks Suzi in the high chair, “Why don’t you nurse your babies while I finish breakfast.”

My eyes tear as I know this is one of the last times. “Aunt Marti, I know she’s not real but this is…” “Don’t apologize Melanie, I’m crying too.” It’s a funny sight; I’m nursing Sarai as I get out Suzi’s Sippy cup for some juice.

Marti tells me, “Sit down, you won’t see me doing something while nursing a baby.”

“I hope you remember that Aunt Marti, but I’ve already seen you do it and I’m sure Sara has seen it too.”


When I look down by Marti’s feet and I’m alarmed. “Aunt Marti, I need you to go lay down on your bed.” She turns around and looks at me and I point to the floor near her feet.

“Thanks, but don’t be alarmed.” I point toward her room. I call Mom on my cell phone and tell her about a spots of water and blood on the floor. Mom will be here in minutes and I call Sandy next. Sandy begins by giggling, “You’re early girl.”

I tell her, “No Sandy, I need to know if you or your mom can come over quickly, Aunt Marti is spotting.” Sandy’s the first to arrive as she ran over, Mom and Dad are next only because Dad cut-off Sandy’s Mom at the corner. I placed Suzi on the bed with her Mom and ask Marti to roll enough so I can get a towel under her.

I would have been at the head of the bed with my Dad, but I was at the foot end in Melanie mode. Mrs. Johnson gave me a hug, “She’s going to be okay, but you did a great job in calling for help.” I could see my Mom shaking her head. I wasn’t sure if she shook her head because I did a good job or because I’m her son.

“Melanie, please get me a clean cloth and a bowl with warm soapy water. Dear why don’t you and Sandy take your nieces to play in the living room and Caroline and I will look after Marti.” Dear is Dad, not me. After I bring the warm soapy water, I go and kneel next to Marti and hold her hand. I guess Mom and her know she’s alright, Marti is smiling.

I ask, “Why are all of you smiling?”

Mom looks up and looks me in the eyes, “Because we are all proud and amazed by the great niece Marti has.” I’m fighting tears, mostly because I’m happy. Mrs. Johnson went out to check on the girls and the next thing we hear is laughter. She just noticed, Sandy had run two blocks in her teddy bear pajamas. Adding to the laughter I searched for a tight skirt and small blouse for Sandy. Caroline Johnson made up more batter and cooked everyone a pancake breakfast.

Mom had calls Dr. Kylie and she will see Aunt Marti at 10:30 a.m. at the clinic. Every one ate breakfast; even Marti ate a little and drank some juice and water. We took an overnight bag for Aunt Marti just in case.


Sandy stayed with Suzi and Sherry while we took Marti to the clinic and Mrs. Johnson went home. I would have stayed home but I already promised to bring the babies back today. Marti is taken immediately into an exam room and Mom goes in with her. No sooner does Sara arrive in the office and a nurse calls me into the back with my babies and she puts me into another exam room. She tells me, Kim Kelley, their Nurse Practitioner, will be right in.

Kim is soon into see me. She asks, “Melanie, I need for you to take off your blouse; the special breast forms need to be taken off.” I feel as she is saying it, that it is emotionally hitting me. Kim lightly takes my hand, “Don’t worry, we understand.” I look her in the eyes and there is a gentle smile of support. I begin to unbutton my blouse and finally my bra. I lay back on the exam table.

Kim talks to me as she uses the solution to work through the glue attaching the breast forms to my chest. “So Melanie, tell me what all you’ve enjoyed about your experience so far?”

“Well it’s not now that’s for sure and we don’t have time for all of it.”

Kim says, “We have time, these forms have a lot of glue holding them onto your chest. It will take some time to work them off unless you want me to pull like taking a band-aid off. The word is you have been a very good mother all the way through.”

I feel good in talking to her and smile as we talk. When I mentioned taking the birth control pills and some other hormone pill; she asks me, “Are you ready to go off the hormone blocker?” I had forgotten I had even taken the shots for the blocker. “No, I hope I don’t have to go off it today.”

“I guess I never expected I would really feel like I was having the experience, but Dr. Kylie has treated me extra special. I’m surprised for a boy that she’d do what she did.”

Kelly asks, “Did you always feel like you were a boy as you went through everything?”

I look up into Kim’s face, “You already know the answer, so why do you ask?”

She says, “It is important to hear your thoughts. Dr. Kylie treated you special because we try to do that with each of our moms. Plus we’ve been impressed with the support you’ve received from family and friends. You know not every girl is as fortunate as you.”

Dr. Kim lifts off the breast forms as they come loose; I’m surprised that they are not as big as they look when I’m wearing them or in relation to how heavy they feel. She helps the nurse clean me off and to sit up. I feel naked as I want to hurry and put a bra on. Kim is pressing around my chest and touching my nipples. I don’t notice my chest but I feel my nipples responding to her touch. They are not only sensitive but I smile at how they feel.


Kim has me look down, “I don’t know if you can tell but your nipples are larger than they were and your breasts are puffy a good inch and a half around the nipple. That is with the breast forms having been pressing them down; it is possible they will be noticeably puffier without the larger forms. …Now I will again ask do you want me to give you the medicine to counter the testosterone blocker.”

“What will happen if I don’t?”

“The blocker will still be working through the month and might take another month to be completely out of your system. Seemingly some of the female hormones you took were strong enough to affect more of a change. Dr. Kylie can and should explain this more. We expected ant female hormones to have run their course. Neutralizing the blocker with a testosterone supplement should cause that to go down quickly. Not to use the supplement could prolong the changes into March, maybe even April by what I see has happened.”

“We officially need to have your permission to begin a new treatment as well as have your mother to approve it.”

“Well then I will wait and have to talk with my parents about what you said.”

“Well I will see if they are done with your Aunt so you and your mother can make the decision.”

“No, that won’t be necessary because I’m not doing it today.”

I smile, “Can I change the topic; I would like you to ask my sister to come back here. I can’t wear this bra and I feel naked without one.”

Kim says to me, “Unless you think she has spare clothes in the car, I don’t think she is going to have one with her.”

“You’re probably right, but Sara has become my big sister as I’ve been going through this. I just need to talk to someone and Mom’s busy.”

Dr. Kelly says, “Well I do have a bra with me; it should fit you except the cup size will be a little big. I keep a change of clothes here, but I don’t want it to appear that I am enabling your decision.”

I blush, “I’d like to do that if you’re willing but I’d like to ask my sister first.” Sara tells me when she comes in, “Aunt Marti is okay but she’s going to need bed rest all weekend.” She teases me about thinking she would have an extra bra with her. But together she and I have enough to pay for Kim’s bra so I don’t need to return it. The bump can come off but the skirt won’t fit properly.

It’s nice to wait for Aunt Marti back in the waiting area, to see her come out with a smile and relaxed is great. It changes my focus onto what’s important. Aunt Marti has been given permission to rest at home if she promises to be good. It’s 1:00 when we have Aunt Marti resting at her house and Mom tells me to change and go shopping with Sara for what I need. I wasn’t going to go, but Mom insists. “I’ll watch your Aunt this afternoon so you should go. You’re going to be watching your Aunt very closely the next two weeks if the baby waits that long.”

It feels nice but strange to wear the regular breast forms again. Sara helps me put them on and she notices that I now had small breasts buds and soft tissue. I tell Sara, “I’ll tell you, Marti and Mom when we return from shopping. Dr. Kelley said they will shrink back and I’ll be a regular boy in time.”

Once I’m changed and ready to go, I check with Mom and Dad as I need to know the limit of what I can spend. Mom hands me a list and I take a look:
1-2 skirts, 2-1 jeans or slacks;
blouses, sweaters, and camis;
knee high socks, pantyhose, stockings
2 bras and 6 panties
2 dolls (that you’ll want to keep)

Sara is looking over my shoulder, she points to the dolls, “That’s a neat idea.” I point to the stockings, “Mom, why stockings?”

Mom replies as eyes light up, “Let Sara help you select a nice pair. You should have the experience once or twice. Then you can answer your own question.” Mom takes me to the side, “The bra you got from Kim is real cute; you should spend a little extra to get one like it in the right cup size plus a push up insert. You might need to go to a nice lingerie shop though. You can use your credit card for most of it, but this is some sanity money to splurge.”

Sara mentions picking up Sandy as we’re ready to go out the door. Dad comes over and hands me fifty dollars, “Please make sure you treat Sandy along with telling her and her mom thanks for us.” I give Aunt Marti a kiss as well as my parents. I pick up Sheri as we’re taking her with us.


I speed dial to Trudy; she should be getting off work. I get her answering message, “Trudy, I’m heading out shopping with Sara and Sandy, if you can meet as at Oakridge Mall. I’m shopping for two dolls as well as some new outfits.”

Once we’re in the door at Sandy’s, Sara jokes with her, “What you’re not wearing your pajamas to go shopping?” I add, “I wish I had realized what you did, I didn’t get to enjoy it.”

Sandy holds her own retorting, “I wore this outfit thinking it showed about as much and looks prettier.” She’s right as she turns around showing off her colorful mini-dress. Her tights and her medium length coat will give just enough protection from winter elements.

Trudy calls back, “Where were you this morning?”

“I’ll tell you when we’re together; suffice to say everyone is alright now.”

“You can’t say that and not tell me…”

Sara tells me as she clicked off my phone, “I bet you’ll be hearing it, for hanging up on her.” I couldn’t believe my sister would do that today.

We pull into the north lot at the mall as Trudy rings, “I’m here, but where are you?”

“We’re parking now; we’ll be at our spot in two minutes.”

“Great, but tell Sara, I’ll get her for cutting our call off.” ‘Yes, that’s my Trudy!’

Sara giggles, “How’d she figure that out?”

“She sensed the dark side of the force, Evil Sister.” Sandy brakes out giggling to the point she snorts twice. We both look at her wondering how petite Sandy could do that.

We all give Trudy a hug as we met, and Trudy kisses me. It was short, sweet and delightful, it catches me as a pleasant surprise as she hasn’t done that in public. We sit near the fountain and update Trudy with all that happened.

We hoped to have oodles of fun; shopping for the lingerie and dolls will be the most fun. Sara insists that I get both the pretty bra and the silicone inserts to push up what I have. Our associate at Victoria’s helps me find three bras from which to choose. While all three will fit, it takes trying them with the inserts to rule out one and leaving me two nice choices. When, we all agree on the same bra Sandy giggles, “That is unusual.” Kathy our sales girl whispers a suggestion to Sara, “I think your sister might look better with something to enhance her hips and buns, but I’m not sure she’d be open to me saying something.”

Sara, “Hey Sis stay in the changing room, I’m getting something else I’d like you to try.” I guess Trudy quickly shook her head in agreement. Kathy had quickly opened the packaging.

I say, “Really, you think I should, how about Mom?” I hear the three of them muffle their giggles. I undressed and ask for the new mini-dress I purchased. The look is a drastic change and gets a quick response as I step out to get their opinions. “OMG look at you Melanie,” Sandy says as she pulls me to a full length mirror. She mimics my niece, “Ut O, Untie Melwanie, I thwnk my Daddy wouwd say yor hot. Weil that be okay wit yor Mommy?” Trudy steps up for a close look, and gives a mock sizzling sound as she touches my hips.

“I think Mom will be okay with it as long as you’re not having s e x. and Dad doesn’t see you,” Sara says as she nudges me. I slide my hands down my side not believing I have hips and it is my body we’re talking about.

Trudy asks a salesgirl, “Will it be okay if she wears all of that out of the store?” I head for the door when Kathy says yes. Trudy catches me, “Dah girl, it means you get to wear it while we still shop. You need to stay in here to get your other clothes and pay for things.” I turn red with embarrassment. Waiting in the register line is stressful. Sandy remarks about guys and even girls looking at me.

I mention, “There are more attractive women than me in the shop.”

The girl behind me taps me on the shoulder, “You’re the girl next door who just blossomed. Smile and don’t let it throw you, you look especially nice.” I smile and say thanks, until she recognizes me from school. “OMG, well I guess you did blossom.” I raise my hands to my face and I’m about to run and cry. She puts a hand on my shoulder, “Don’t run and quit your crying, I won’t tell unless you give everything away.” She hands me a tissue, “I guess you had to unwind after the twins, huh?” I giggle and relax, “Thanks Joan, I guess I owe you.”

We ask Joan to go eat with us, but she advises against it, because she had three friends with her. “I can keep a secret, but four of us won’t.”

The doll shop is very wonderful, for me the dolls are all beautiful but they’re only to look at. They’re from fairly nice to works of art, but even the fair ones begin at seventy dollars making two unaffordable. One baby ‘Grace’, I really love her, is on sale at ninety-five dollars and Sara finds another beautiful doll, it’s a special edition for a cancer cause. Sandy wants to give twenty dollars toward purchasing them, Sara volunteers forty dollars and that’s before Trudy has an opportunity to help.

“You three think I should do this if I really like them?” Sandy quickly smiles in agreement and Sara gets a bit cruel, “Only if you love them and will really give them a nice home. Don’t tease your babies if going to leave them.”

I decide to get the dolls on my own; Sara gets two outfits for her namesake and Sandy gets one outfit for Allyson. Trudy buys the stroller for twins. By the look of one sales lady, I think she questions the type of girl purchasing the dolls. Sara assures her, “She’s already shown she is a good mommy.”

Sara calls Marti’s house and advises Dad be sent home if they want to see me as I’m dressed.

Saying all the women are pleased when we get home is a gross understatement. Much like Sara said, Mom says “Honey, you couldn’t look more gorgeous. But if you were for real, I wouldn’t let you out like that.” She pauses, “You don’t look bad or anything; you’re just too young to look that hot.”

Aunt Marti asks me to come close to her, “Melanie, do you know how beautiful you are?” Trudy hugs me from behind, “Thanks for telling her that I hope she hears you.”

“I don’t think I am that overly beautiful, but yes I feel beautiful inside and out. I think I take after you and Mom.”

Trudy whispers, “You can’t get any more beautiful than you feel and I agree you are as beautiful deep down as any of us. I hope part of you always feel like a true sister to all of us.”

As the others go out to the living room, Trudy pulls me into my room and gives me a passionate kiss.

Story to continue…

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:
60 users have voted.

And please, remember to comment, too! Thanks. 
This story is 4873 words long.