Jack and Jill by Trudy - 10 - Melanie Goes on a Date

Jack and Jill, by Trudy
10 - Melanie Goes on a Date

By Jessica C

Aunt Marti wakes me at 7:00 a.m., “I know, I said you could stay out a little later, but I am upset that you stayed out until 1:15 a.m. and didn’t call.”

Melanie groans, “Please, Aunt Marti, it is only 7:00 can’t I just sleep in a little longer?”

“You’re to be shadowing me and I’ve been up over a half hour so up and out of bed.” Aunt Marti pulls me get up and pushes me into the bathroom. She talks, “I will get us some breakfast, and you need to get the girls up. Please, pack a change of clothes for Sherry and then change Suzy’s diaper and pick out a nice little outfit. She and I are going to Grandma’s. You will have Sherry this morning and afternoon.”

“I will be back in time for you to go on your date with Derrick. Make sure you check everything so you’re an attractive girl.”

Marti starts to leave, “Aunt Marti, can I ask you something?”

I am not surprised she stops to listen, “Yes Melanie, what do you want to ask?” I just begin shampooing my hair and I feel comfortable talk talking to Aunt Marti; it wouldn’t have happened with my Mom. “It’s just that I want the experience of going out on a date as a girl. Except the idea of having another boy kiss me, I’m kind of excited, but not. How does a girl decide when to say ‘no’?”

Aunt Marti is firm about this, “You never lose the right to say ‘No’ as a girl; you need to respect yourself and expect him to respect you too. That said and you being seventeen, I don’t think your problem will be Derrick going too far. Don’t get upset or embarrassed when he hugs you that he might have gotten hard because of his feelings he’s having.”

“Gross, Aunt Marti. You don’t think me kissing another boy is gross?”

“If you are out to have a girl like experience; you shouldn’t be surprised he has a boy experience. Melanie, girls and boys often feel awkward not only trying to figure out the other person. You’re probably nervous because you aren’t even sure what you want him to do. Maybe you not acknowledging you want him to kiss because you’re like the idea of being a girl.”

I’m surprised how Marti talks to me, but I shouldn’t be. I’ve come talking to her about how I think and feel on a lot of stuff. I even nose my way into her stuff. “So am I to take your silence Melanie to indicate you’re thinking, yes?”

“I’m surprised you aren’t talking to me like a parent and just telling me ‘no’. It’s like you know what I’m thinking and feeling.”

“Dah Melanie, I am a woman so I know that part better than you, plus you and I are close. I have more trouble acting like your Aunt than being a close friend. I’m sorry if I see you more as a sweet teenage girl than you are comfortable with.” I’ve rinsed my hair and I am now putting in the conditioner.

“Marti can you see me in the shower?”

“Um, I can see the silhouette of a girl I am talking to. But I am going to get out of here and let you finish on your own.” I can hear her leave as I think how neat it is to have her as my Aunt.


I spend part of the day cleaning up around the house and playing with Sherry. I also enjoy times when Marti makes the two of us a snack and some tea. She’s cleaned up and in her casual fleece sweatshirt dress she’s ready to go to Grandma’s. “I think that dress is real cute, are you look it very comfortable in it.”

Marti says, “It will be nice to wear something comfortable and not worry about nursing.”

“So are you comfortable?” I shouldn’t have asked.

“Not really my breasts want to explode, but I’ve taken some medicine. It isn’t any worse than her munching down on me, just different.” Marti sees I’ embarrassed a little for asking. “Just be glad you won’t need to go through it.”

I ask, “So how does it feel, having a baby inside of you?”

“I’m use to the physical part, but with having Ron gone the mood changes are harder to deal with.” Marti is looking off somewhere, fighting tears and kind of seeing Ron. I offer my hand and she holds it tight. I’m not ready for her tears and not sure what to do. I lean over and give her a hug. She dampens my shoulder. I mimic some of her movement like petting her hair, trying to change my expressions to be like hers and then a smile.

I touch her bump and she holds my hand there. “Did you feel that?” She moves my hand again and I am sure I felt the baby move. I smiled and look up to her and she smiled back. “That is the good part and it is nice to have someone to share it with.” She wipes her tears from her eyes and touches my lips with her tears. “This is a good time to have Melanie with me.”

One of the things I am learning, quiet times with a girl are different than with a guy. Usually if I am quiet around girls I’m not sure what to think or do, so I don’t. Now I kind of have feelings and think about Marti. I’m trying to be of comfort to her, but it seems to naturally happen.

Marti leaves after our visit and I’m tired, it is like I had continued working hard around the house. But I was just sitting there. The next thing I know, I hear Sherry waking from her nap and I go check on her. I kinda liked that I’m beginning to react and do some things naturally. I have Sherry dressed and we’re active playing house between my getting and sending text. It is mid afternoon when Marti and Suzy are back


Marti sends me to take a bath and begin getting ready for my date with Derrick. I start the water and Marti comes in with some bubble bath. “Marti, I’m big enough to make my own decisions, so please stop it.”

She apologizes, “I will try but I want you to get into the girl thing, it will be fun if you relax. I did this early on when I’m pregnant, being nice to myself. If you shampoo your hair, call me when you are ready to rinse out the conditioner.”

I protest a little being a boy, but remember only girl parts are showing. I’ve shampooed my hair once when Marti knocks and asks, “Would you mind giving Suzy a quick bath.”

“If the water isn’t too hot that would be fine.” Marti trots in carrying Suzy and checks the water and hands Suzy to me. Sherry begins to take off her clothes, but Marti is nice enough to stop her. It is fun to have Suzy in for a minute, and I am glad to watch how Marti wraps her in a towel and dries her.

I am shampooing my hair a second time when Marti leaves to dress Suzy. Sherry stays so she can tell her mother when I am conditioning my hair. Sherry watches her Mommy leave and gets undressed as I go under the water to rinse my hair for the conditioner. Her feet slip onto me as I come back up out of the water. She is giggling big time, “I fooled you and Mommy.”

She is sitting on my lap facing me. She points to the baby shampoo; so I wet her hair and I help shampoo and condition her hair. I begin conditioning my hair as Marti is back and finds Sherry in the tub washing with the bubble bath. “Good timing Aunt Marti, by the time you dry her off I will be ready to rinse out the conditioner.”

Marti has a rinsing hose for rinsing my hair, which feels real good as the water cascades down my hair, face, shoulders and back. She holds my towel as I stand up to get out.

There is an outfit on my bed with a note: “Don’t get angry with me, I’m just the messenger. Sara asked me to layout this outfit for you. She thinks it is nice, neither over kill nor more Mel than Melanie as is her fear. Do as you please, Love, Aunt Marti.”


I didn’t eat, not being sure what Derrick has planned. Derrick has decided we will go to a dance at another high school, since the students won’t know I’m not a real girl. We are hanging around with a friend of Derrick’s and his date. She sings most of the songs at the dance and looks at me like I should too.

Finally for a break I say I’m going to the restroom but Natalie came with me. I use the stall even though I didn’t need to pee. Back out in front of the sink, Natalie asks, “Would you mind if I put a little blush on you while we’re in here,” she says showing me the blush and pointing to my cheeks.

She does and it makes a nice difference giving definition sculpting of my face, “I bet Derrick kisses you now.” Without thinking I use just a drop of perfume and Natalie transfers some to my neck.

The second dance is slow and Derrick is holding me closer to him. I lean my head on his shoulder and as I look up to him my lips are touching his neck. I felt comfortable even more than I thought. I am letting myself enjoy the moment when I feel Derrick’s lips touch mine. His lips are warm and nice and I’m kissing him back. When we stop kissing the music is over and Natalie is lightly clapping.

Derrick says, “I’d say I’m sorry but you didn’t seem to mind.” We get off alone and we’re talking, “I’m sorry Mel, I usually am awkward around girls and I think taking you out helps me. You are as pretty as any girl I’ll probably ever date.”

“I don’t think you need to worry Derrick, I think girls naturally will like you. All you need to do is relax. I’m kind of sorry I kissed you but since being Jill for Halloween, responding as a girl might comes easier.”

“But why did you kiss me back,” He asks?

“I guess because we both liked it. I saw me as a girl kissing a boy and I thought you saw yourself kissing a girl. My Aunt Marti said I shouldn’t be surprised if you react as a red blooded boy.” We went back and dance till a more of the others were leaving. I could tell that Derrick is still excited about me. We drove and he asked if we could stop and talk.

It’s kind of weird, he and I know I’m really a guy but we’re acting like a boy with a girlfriend. I scoot over and he leans over and kisses me. As he leans back during our embrace pulls me and I’m half in his lap like I think a girl might be. One of my hands slips down and I can feel him. Instead of being grossed out I lean to kiss him again.

“I’m sorry,” Derrick begins, “But would it be okay if I take you out on a date again.” I find I’m not looking him in the eye when I say, “I think that would be fine, but I don’t want either of us saying sorry.” I sit back and straighten out my skirt.

When Derrick takes me home, he walks me to the door and we pause. We look into the other’s eyes saying nothing until I say, “Please” and he kisses me again. I go into the house closing the door behind me and I’m leaning back on it. I’m relieved that Marti is not right there, but I hoping she is still awake. I use the bathroom, in part to check my makeup, cleaning up any smeared lipstick.

I went to the kitchen getting out some cereal and milk as I was starving; as I sat down to eat I hear Marti giggling, “So he didn’t feed you.” She pauses and comes to sit down with me. “Other than that did you have a good night?” I smiled and told her, “Yes.” We had a good chat. My phone was buzzing from Sara and I also had a text from Sandy.

I’m proud as I go knowing I need to take off my makeup, shower and get to bed. “So…,” I know what she’s going to ask?

“Yes, he kissed me and he’s asked if we could date again. Yes, he got excited like a boy but nothing happened… We know I’m a boy but we dated like a girl and boy. He’s hoping this helps him in dating girls… So now I told you, can I go to bed?”

Marti smiles, “I’m just happy you talk about it.”


It is only seven thirty; I am dressed and waking up Sherry and lifting Suzi up out of her crib. Both seem to have slept well. I change Suzi, clean her up and get her first bottle with two spoons of rice cereal in it. She will probably get a little grumpy as Marti is not nursing her any more. I expect they will both be a little grumpy. But for now Sherry is in her booster chair eating like a big girl.

Marti is coming, I can see she has a question, probably something important like, ‘what do I want for breakfast?’

“Melanie how many pills do you have remaining?” “Umm.”

“I thought so, after breakfast you can get dressed and we’ll have a talk.”

“How did you know?”

“Let’s say, your mother, sister and I put our heads together and we smelled another girl.”

I’m now scared, “What are you going to do? I am surprised my Mom isn’t over here yelling at me and tanning my hide?”

“So you expect her to treat you like that? Fortunately your mother is nicer than you think. I’ll let her tell you, but you should have thought better.” I hate that when a person makes me feel bad about something I said.

“You want more of the girl experience than you were admitting, don’t you?” Suzi wiggles away from her bottle; I need to pause with her hopingshe’ll then burp her. Marti smiles as I needed time to think as well.

I put a diaper on my shoulder and begin to walk with her she’s big enough that I don’t need to tap her back much. Suzy’s smile has me jealous, growing up as a girl will be quite natural for her. I kind of wish that were true for me, but now I’m going to lose my chance. “What am I saying?”

“What was that Melanie?”

“I was just talking to myself; I didn’t mean to do it out loud.”

“But your problem is there is too much you are just saying to yourself and not admitting to anyone. Am I wrong?” With that said; Marti takes Suzi and gently lifts my chin with her other hand. We smile at each other. “Go put something casual on as we need to talk.”


I go to my room and find that Marti had put out one of her long dresses made out of fleece. It’s like a sweatshirt but long and casual. It still has tags on it, I guess it is new and mine with nice footy socks to go with it. It’s gray with a wide pink stripe down each side, cute. It even has a hoodie if I want to be real cozy. I brush my hair just enough pulling it into a ponytail. Marti smiles as I come back out very relaxed. I wearing the outfit she had set out and it does look adorable.

I grab a cup of hot chocolate, sit on the couch as Sherry comes and snuggles with me. Marti sits down placing Suzi on a blanket. I had already dumped the disc of pills in the trash, making sure Aunt Marti saw me.

“So Melanie, were they all your pills? I know I said something about the girl experience but I hope we have both thought twice about this.” My smile leaves though I don’t think she wants me to feel terribly bad, just to wise up.

I stay quiet until she asks, “So what have you been thinking? You tell people one thing but your actions seem to have a different message.”

I hold my hot chocolate in my lap and hug Sherry with my other arm, kissing her on the forehead. “I kinda like the girl experience; I don’t expect you to understand.” Marti moves to the couch, putting a hand out for me. No fair, tears fill my eyes. “Your Mom says you have a gentle heart.” As Sherry moves to her Mom, I pick up my hot coco with both hands taking a sip.

She says, “What do you want me to understand?”

“I’m not sure, may be just that I enjoy part of this girl experience and it isn’t easy on me.” I pause, “No one knows but I use to sneak into Sara’s stuff. I thought I was just getting away with something; I just like being sneaky, it’s sad but no one pays attention to me.”

Marti looks me in the eyes, “But are you surprised how much you enjoy girl stuff?”

I am sure I am like a little bunny poking up its head and ears like, ‘I’ve been spotted.’ “You don’t seem surprised?” Marti’s smile widens to a smirk. “Mel, you are a neat guy, but I’m not surprised that part of you really enjoys this. You and I talk a lot and this matches with a lot of things you don’t say.”

“Huh?” I don’t get it.

“Mel, it is like you’re getting punished for something and you have kind of enjoy it.”

I smugly say, “Well it is like if life gives you lemons make lemonade.”

“Not quite, it is like you want to be doing this. I don’t want to be accusing you of something, but I am trying to honestly ask you how you feel… feel about being Melanie?”

Part of me wants to cry… I’m use to keeping even the people close to me at a distance. Marti is one of them. She takes my hand again and I know she wanst me to trust her. “I want… You need to promise not to tell anyone including my Mom?” Marti squeezes my hand but she doesn’t promise.

“I’m trusting you; …I’ve always felt bad about it, but yes part of me likes being Melanie. There are you happy!”

“Only if you feel good that it isn’t a secret anymore and remember to talk to me.”

“Please, don’t tell my parents; I know you didn’t promise but I’m trusting you.”

“Melanie, I hope it is you who tells your Mom and your Dad when the time comes. I do want you to trust me as I am trusting you with a very personal time in my life.”

She continues, “You know, this is not a time I would generally would trust a boy to understand and be there for me. I know I wouldn’t share it with my own brother. Don’t feel bad but Sara and I have always seen you as special, kind of a sister as well as a brother.”

I scoot forward and gently kiss Marti’s cheek as I give her a gentle hug with Sherry snuggled between us.” As we separate, Sherry’s touching my chest, “Mommy she is soft like you.”

We talk another hour; mostly me talking. Marti finally tells me I’m watching the girls while she is going shopping.


Grandma Briggs comes over as I finish cleaning up from lunch and I’m trying to put the girls down for a nap. Sherry won’t go to sleep while Suzi might if Grandma didn’t bother her. But that is why she came.

Grandma does let me finish the dishes and thinks it is funny when she lets me change diapers or take Sherry potty. Grandma would like me to change clothes, but I don’t think another girl outfit will be any different. Marti is only half surprised when she gets home and sees Grandma.

I busy myself texting with Sandy, Trudy and Sara.

“Has Aunt Marti talked to you about anything special,” Sara asks? When I pause, she says, “Never mind, I will come and see you and Granny. Hey Mel, your friend Al called asking why you haven’t been over playing games at the mall.”

I pause texting, to call Al but forget to change my voice, “Hey Al, I hear you called thanks man.”

“Hey Dude, what’s with the voice?”

Back to Mel’s voice, “Sara said you called, I’d love to get to the mall for some games.” “…I’d have to check …maybe Sara can give me a ride. …Okay, I’ll try to be there ‘round five.” Interesting, our conversation is over in three minutes.


Sara knocks on my bedroom door as she and Sherry come walking in, “I like your dress L’tle Sis.” I look down, twirl once and smile, Sara’s amused as Sherry comes over and hugs my legs and I lift her up. Sherry pats my chest again, “Untee Melwanie is soft.” Sara breaks out giggling. “Don’t waff, you hurt her feewins.”

Sara says, “I guess she told me; Sorry Sis, sorry Sherry.” Sherry gives me a big hug.

“So who was that short conversation with ‘Mel’?” I tell her and ask for a ride to the mall later.

“Mel, you need to fix yourself up. Don’t make Marti and others suffer with that lazy guy stuff. Brush your hair and put on a little makeup, even when you’re not going any place. Sherry and I will get out your room and we’ll let you get a shower and see you afterwards.”

By the time I am out of the shower and back to my room, Sara’s been back in and laid out panties, bra, skirt, camisole and sweater. It’s a nice combination, better than I would have picked. I’m back out with Granny and everyone. Sara’s smirking and Granny is warming up to me, “My daughter tells me you’re a good little helper.”

Soon there is someone at the door delivering Chinese, Granny’s treat. I quickly set the table, pouring milk and have water heating for tea. Granny causes me to pause as she is sticking earrings in my ears. “Your mother said your ears were pierced so I want you to have these for a while.”

I try to move to see them but Granny stops me and asks me to turn around and lift my hair. She’s putting a cameo necklace on me. “They’re mine, your great grandmother gave them to me as a young lady.” I go to a mirror and see they are dainty and more appropriate for a younger woman. Sara and Marti both squeeze my hand telling me, “Remember to thank Grandmother.” I need to catch my breath and grab a tissue. My voice becomes the softest yet, “Thanks Granny this is special; you shouldn’t.” She touches my lips with a finger and leads me to the table next to her.


After we eat; I ask for permission to go to the mall to play video arcade games with Al for a few hours. But my Aunt only gives me an hour; she also reminds me, I need to go as Melanie. I’m considering staying home but Aunt Marti says “You’re going, you need to get out of the house; being with some of your guy friends will be good for you.”

Come five Sara takes me; she’s meeting Kathy to look around the mall. I text Al so he’s not surprised I’m dressed as a girl, but I guess he’s not totally prepared. “Dude or is it Dudess?”

“Knock it off Al, it is bad enough I got me in this mess.”

He jokes, “How’s your pregnancy going? Do you know yet if it’s a boy or girl yet?”

“Knock it off or I’m leaving.”

“Don’t blame Mel; you can’t blame me for teasing a little. You actually make a decent girl. Hey, please use your girl voice and don’t let on who you really are. It could hurt my reputation.”

I say, “You don’t have a reputation worth hurting, but I don’t think either of us wants attention.” Figuring out what to do with my purse is my next problem. Having nails also takes some getting use too as both games we play are very touch sensitive. It takes three games before I am able to beat Al. Unfortunately I’m drawing attention. One guy asks me to be with him after Al says we’re just friends. I refuse, but he challenges the winner of the next game.

I considered losing but that isn’t my style. The jerk surprises me as he’s good and it takes me a bit to challenge him as I still lost the first game. I beat him in the second game and we’re about to play the deciding game when Sara shows up. “Melanie, we need to be going.”

The guy speaks up, “Hey, this is our deciding game leave her alone.”

Sara said, “Don’t do it Melanie, you’ll hurt the boy’s feelings.” I’m embarrassed though I know she’s right. The jerk bites Sara’s hook and we have a last game. I’m pissed as a nail breaks but I win easy enough. Sara wins a dollar and we leave the arcade quickly.

I’m expecting to leave, but Kathy and Sara have other plans. We’re quickly at L.A. Women’s World getting appropriate shoes for cheerleading. Sixty dollars for cheerleading shoes that I will only be using for a month. I think it is too much, but there are two votes against me and I lose. I am upset that Kathy follows us back to Marti’s house as they want me to do a cheer with them in front of Granny. Granny’s left so I think I am safe, but Marti has us do a cheer and gets it on her smart phone, not good.

To be continued…

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