Jack and Jill by Trudy - 12 - The Date

Jack and Jill, by Trudy
12 - The Date

By Jessica C

Once again I felt like Trudy’s casting me as a fantasy character, instead of Jill, I’m to be Cinderella. This time, with my eyes wide open I am going along with it. Trudy takes me to one of those ‘Nails’ places at the mall. Even without using fake nails they have my nails looking feminine and beautiful.

Once back to Aunt Marti’s I am allowed to take off my baby bump for part of the day. I never thought a boy would be so happy to put on regular girl clothes. “Trudy, I feel like my old self.” To which Trudy and Aunt Marti giggle uncontrollably. I tried to correct what I said and how I said it, but it only gets worse.

Trudy has a cute holiday bracelet and necklace set of red Christmas balls that I’ll wear with my blue dress. I want to change into it come noon but Aunt Marti says “No. But we should fasten on these breast forms as well as your gaff.” With that I’m led into my bedroom while Trudy watches Suzy and Sherry.

Aunt Marti takes breast forms that are sitting in a new bra and has me lay down as she draws to circles for the new breast forms; they are slightly larger. Aunt Marti informs me that they’re noticeably bigger; they’re now a very full B size. Between having the bump off and the larger breasts on, I’m tickled with the difference. The gaff requires more shaving, which hopefully will help reduce the discomfort when it comes off. Come 1:00 p.m. Marti takes the girls as she and my Mom go shopping.


I set out to make popcorn for Trudy and me to eat while watching a movie. No sooner is Marti’s car out of the driveway and Trudy stops me from making the popcorn. Trudy says, “I’m sorry but I don’t want your buttery hands on me.”

“Don’t worry I’ll be careful.” Trudy giggles, “Melanie, you don’t get it. It is you I want to snack on.” She leads me over to the oversize recliner that we both sit down and then recline back. Trudy’s first kiss is warm and passionate, something dreams are made of. I’m wearing a skirt and when Trudy puts her hand inside by leg my emotions start to climb and skyrocket with her hand on me.

“Trudy, don’t you think we should be more careful?” She giggles again, “Don’t worry I won’t get you pregnant.” The way I was feeling, I’m not fully sure. I know even as Melanie I want Trudy.

“But Trudy dressed like this I feel more like another girl not Melvin.” Trudy rolls a little on top of me and in a sultry voice says, “That’s okay.” I know one of her hands is on my breasts and despite what I don’t feel it’s provocative to me. I begin to unbutton Trudy’s blouse thinking for some reason she’ll stop me. So far today all my assumptions are wrong. My biggest problem now is my mixed emotions. I find Trudy sexy by both Melvin and Melanie’s standards.

Thirty minutes later we haven’t gotten past kissing and some hot petting, except I’m the one who is out of her panties and bra. I do manage to get her bra off and nibble on one of her breasts. It’s at that moment Trudy felt the excitement get out of her control and she pulls back.


She has me take a shower shampooing and conditioning my hair. She even checks my legs and underarms and has me shave them again. I’m back into a fresh pair of panties, bra and my robe. Then Trudy has me sit down so she can blow dry my hair as she styles it for my date.

I’m back in a white cotton blouse and my skirt when Aunt Marti and my Mom drive in. Trudy and I go out to help carry packages. Marti asks for me to get Suzi and to change her. I like how Suzi clings to me like a second mommy. She even reaches into my blouse as she does with Marti. Where Sherry knows Auntie Melwanie is a boy Suzi sees me only as a person with bumps on my chest which she prefers.

Aunt Marti seems to suspect we’ve done something yet she is quiet; especially when Mom is nearby. Mom compliments how I look and Marti asks if we have had a good time with a telling smile. She even hears Trudy telling her how she helped so I’d have a good time and experience in being a girl tonight.

Come 5:00 p.m. Aunt Marti and Mom give me permission to start getting dressed and ready for my date. Seeing Trudy excited to help me, they suggest she leave before Jacob came. Trudy responds, “I would like to stay and talk with you after Melanie leaves on her date. I’ll just be a girlfriend that dropped over to see her friend’s beau.”

“Can you atleast wait until she has her panties, pantyhose and bra on before you go in to help her,” Marti says looking to my Mom for affirmation. Trudy smiles with a mischievous grin of compliance.

My Mom comes in a moment before the other two. “Honey, how are you doing, are you excited about your date?”

“Mom, are you really expecting me to be excited about going to a dance with another boy?”

Mom responds, “When you’re dress as Melanie, I don’t see it as dating another boy. You’re pretty and in every way I can sense, right now you’re my daughter.” I’m moved and any ounce that’s holding on being Melvin dissipates. Just as I’m settling into a mother/daughter time, Trudy comes in with Sherry following closely behind. I actually was enjoying my mother daughter time and wished it had not been interrupted. I’ve always been closer to my mom, but this was completely new to me.

Mom’s helping me to put on the mini-dress, remarking how it shimmers, making me look all the more feminine. As I’m smoothing out the front, Mom’s zipping up the back and fastening the top little hook. Trudy is kneeling to make sure the hem is down and even all the way around my legs. Sherry is touching my legs, “Auuntie Melwanie yu w’ok beuwitfulwie.”

I pick her up rubbing my nose into her face before I give her a kiss on the cheek. “Thank you Sherry, do you think my date will think so?”

“Mummy and T’udy say you Cindewella to’nite.” Trudy is running a hand along my leg to get me to step into my heels. Somehow it feels extra special that Trudy is helping and not fearful that I’m dating Jacob. Her touches are a reminder of how close we are.

We take my makeup to Marti’s vanity where I can sit and apply my makeup. Mom watches with amusement as I’m doing most of my makeup. I did ask for help in selecting colors for my eye shadow and blush. I hear Mom whisper to Trudy, “Mel’s not only becoming prettier, but she’s more and more girl.” Trudy giggles in agreement, “I’m surprised now attractive I find Mel this way.”

Before they brush and finish styling my hair, I feel Trudy’s fingers bring the necklace around my neck again, and then helps with the matching bracelet. The way her hands are around me, are filed away in my memory. I note the touch of a woman as opposed to how I am use to do things. Once my hair is finished, Marti suggests a change of earrings.

There’s a difference as to which set of earrings to use and then discussion how even prettier the two sets are together. With a towel over each shoulder and an ice cube held to each ear I am getting a second set for each ear. Instead of complaining about the pain or nuisance, I agree and cooperate. The new piercings are like badges of courage or whatever to my psyche.

Though I am ready in plenty of time, I’m to stay in my room until after Jake is here and inside waiting. I try protesting that it’s too girly and contrived for me. I knew I’d lose the protest. Marti has me keep Sherry as I wait and has Trudy come out so my lipstick and makeup aren’t bothered. Luckily Jake arrives almost five minutes early. I soon know Mom approves of my date.


I get goosebumps as I walk out to see him. Marti is right he’s handsome and in every sense someone might say is typical for a guy. Even in my heels he’s taller than me and despite his jacket I sense the strength of his arms and upper body. Trudy teases, “Jake put your arms around Melanie and squeeze together for pictures. She’s a regular girl, not as fragile as she looks. She’s shy so you will need to help her relax and get to know you at the dance.” As we walk out to leave, Trudy encourages Jake, “Jake, you don’t need to wait until you’re back at the door to be affectionate.” I wince as I hear her; she even has Marti’s encouraging him.

I make sure to sit down bringing my hands to sweep my skirt underneath as I do and then bring my legs into the car. Jake gets into the driver’s seat, starts the car and then looks over to me. He’s not looking at my eyes as I realize the top of the dress shows a bit of my breasts. “O, do you like my necklace? Trudy leant it and the bracelet to me, wasn’t that nice of her.”

It took Jake a moment to regain his thoughts, “O yes, it caught my eye and I thought it goes nicely with your dress and the season.” He smiles, “My Mom said you were prettier than the picture on Marti’s desktop. I agree with her, you are very pretty.”

Jake says, “That is neat you and your Aunt are that close that you’re willing to stay with her while she’s pregnant. It’s lucky she has a niece like you.”

I smile, “She’s my Mom’s younger sister and yes we’re especially close.”

“Aunt Marti says you were hurt by a girlfriend who broke up with you.”

“Kind of, it’s not like I want her back, but I have trouble breaking the ice with girls. Jenna knows that and she’s been kind of rubbing it in my face. I shouldn’t be so petty, but I’ve feel like a dork without a date.”

“I guess it’s hard for a girl to wait and boys get nervous about girls saying no. So why were you willing to call and ask me out?”

“Well you’re pretty, your Aunt told Mom you aren’t going with anyone in particular. The truth is, if you said ‘No’ no one else would know.”

“Are there others at your school you would like to date?” Jake smiles, but won’t say anything.

“I kind of like you, but I know it’s more realistic to have a girlfriend closer by. Do any of those girls look a little like me?” I see Jake smile. “You know we could say we met last summer at the shore and were waiting for a chance to date. That way another girl might think she has a chance because she lives closer.”

Jake relaxes and smiles, “That is nice, but if we have a good time it would be nice to be one of your boyfriends.”

“Like I have a lot of them; I don’t. Let’s just enjoy tonight and see.”

Scotch Plains is bigger than my school, so it’s kind of overwhelming to be at a dance with so many people. Jake appears to be popular, so it feels nice to be with him for the night. We meet up with a number of friends. Ken and Marie, Elzar and Tanya are the ones we sit and talk the most with. Elzar’s the most vocal, “Hey, princess you look hot and cool at the same time.” Out on the dance floor, Elzar calls over, “Hey, Wicked is parting the dance floor.” With that I look to Jake’s left and a very beautiful blonde is walking thru the crowd as she’s coming out onto the dance floor. I feel a bit stressed wondering how I’m to compete with her.

“Hey Dreary Dearie, how far did Jake have to go to find one at least mildly cute?”

“One of his friends at the beach said you’re very pretty but your breath stinks. I guess they were talking about your stinking mouth.” I’m hoping we won’t get in a fight as I can tell her claws are probably as sharp as her tongue. The band switches to a slow song and I cozy up to Jake turning my back to her. Jake said something but I put a finger on his lips and then ask for a kiss.

Jenna says something but I distract Jake by putting my head on his shoulder and stretch to kiss his neck. I guess she didn’t know what to do once she’s ignored and others go back to dancing. Her date is okay, but nothing special. I ask Jake about him and he won’t say anything bad. It takes asking Ken later. “His Daddy owns a car dealership and has some money.”

Tanya, Marie and another girl Hanna take me to the girls’ room Tanya and Hanna left as Marie and I are refreshing our makeup. Jenna comes in with her friends and suggests I should leave her school and ex. “Won’t happen until we’re ready to leave.”

“You’re not wanted here!” she gets a little more vocal.

“Hmm, Jake seems happy enough I’m here and most others are being real nice. Jealous Jake’s moving on?” Sensing I hit a sensitive note, “Afraid your boy there will lose interest?”

“He’s as much a guy as Jake and his car is newer,” she’s now in my face as she speaks. I wipe my face and dress like she’s spraying as she speaks. I respond, “Then we should all be happy and go our different ways. I guess some of the Scotch Plains girls interested in him were afraid you’d be like this.” I take a breath, “If you start trouble with me, you’re the one who will be in trouble with school officials.” With that Marie and I take our purses and walk out. Jenna makes the immature move of bumping into Marie.

Once we’re out of the girls’ restroom, I ask, “Marie are there other girls Jake is interested in? Don’t worry I just think I’m far enough away I’m not likely to be real competition as a steady date.”

Marie smiles, “You’re not interested in him? I thought you’re getting on nicely.”

“I’m interested and I’ll date him as I can, it’s just I’d like a guy I don’t have to see on my smart phone or tablet. Plus I don’t want to be too serious, because I’ll going to college.” We stop talking just before we reach Ken and Jake. Closer to 10:30, I’m ready to leave but I ask Marie and Tanya about a girl who looks to be a junior. She has light brown hair with highlights; she’s pretty and has been looking over now and then. “Dawn Towner, a lot of boys would like to date her but no one holds her interest.” I giggle, “She’s either attracted to me or Jake’s got her interest.”

Marie giggles, “That would ruffle Jenna’s panties; not only is she attractive, she’s athletic and a small tiger.” Tanya agrees, with Marie’s assessment.

“So, if they would catch on I doubt he’s traveling thirty some miles to see me.” I want to go over and say something to her, but it might solidify Jake being seen as dork. Knowing there’s atleast a warm chance this is not a repeat gig, I get more aggressive with Jake. I wait for Jake to give me another kiss and I move to hold the kiss and return it more aggressively. I’m focusing on enjoying my girl time. I flirt mostly with Jake but not exclusively.

We leave the dance early enough and since it’s a weekend I have a 12:30 curfew. Before we get into the car to leave, Jake takes hold of me as we talk and I lean back against his car. Jake pulls me away from the car and I think he’s being a gentleman. His hands slip down as our kiss becomes more passionate, I only make sure Jake doesn’t go too far.

Thanking him for a nice time, sends the message for him to start home. I use his visor mirror to fix my lips; I don’t see any other blemishes. Jake asks if I’m hungry and I say no despite starving. We’re home before midnight and we could stay and kiss in the car. But I think of the grief I’d get at school if someone drives by and notices.

I couldn’t feel much but I know Jake’s hand or arm pressed against one breast in passing as we cuddle. The kiss at the door is passionate and I feel him press against me. He’s embarrassed that I notice his excitement. Though he warms part of me, it’s too cold to stay out longer so I say goodnight and go inside. Once I know he’s walking down the steps, I stretch to watch him from the top of the door.


As he gets into the car, I twirl around and leaned against the door with a sigh. I hear Aunt Marti, “I would have expected that from Sara. Does it mean you enjoyed your date?”

Not to act fully embarrassed, I smile, “Yes along with besting Jenna; I think Jake’s a sweet guy.” Seeing Marti’s expression and thinking how she might she might have interpreted ‘sweet’, “I didn’t mean it that way. His Mom isn’t raising any saint, but overall he did well in making me feel like an attractive girl.”

“By the hits Trudy’s getting on your picture from earlier, I already knew guys are seeing you as hot and attractive.”

“Aunt Marti, I didn’t say ‘hot’.” Marti giggles back, “No that came from the comments Trudy has shared with me. I don’t want to imagine what some said that Trudy won’t share.” I flop down in a chair and my dress rides up and Marti giggles. “Now I know why my mother laughed when I did the same thing. But I’m not sure Grandma would be laughing about you.” I scoot over and Marti squeezes in next to me.

“I am glad you had a great time.” She puts an arm around me and it’s more like I’m Sara instead of Melvin. “Will you go out with him if he asks?”

“I’d surely consider it, but I think there are two or three girls there he might get the nerve to ask.”

“How about his old girlfriend, did you get to see her?” I smile, “Yes we were on talking terms, just not too cordial. I hope she thinks twice before showing her fangs and claws. I think one girl interested in Jacob could handle her quite easy, if her status isn’t enough to keep Jenna away.”

“I hope you weren’t a tough girl all evening,” Marti asks with concern?

“Na’, around Jake I was usually a kitten enjoying his strength and size. Plus the dress and stuff feels so nice, it’s hard not to be in a girly mood.” Leaning back turning my head to Marti, she giggles, because I’m so much a girl right then. “Aunt Marti, I should be upset doing things like this but it’s so neat pretending to be a girl.”

“Are you just pretending?”

I ask, “Aunt Marti, are you saying I’m wrong?”

Marti, “No, I’m just not sure if you’re pretending or seeing yourself as Melanie for real.” She draws me to her and I cuddle in her arms. I’m too big to be her daughter, but she’s the closest thing I have as Melanie to a MOM.

“Mom… Marti can you smell another fragrance? In the girl’s room a girl came up next to me to wash and check her makeup. I commented on how nice her fragrance was and I asked what it’s called? She said it’s Craven and just three ounces cost over a hundred dollars. She sprayed it lightly on my right wrist and I touched under my right ear. It is like to die for, but she says she likes Red Door like me. I guess girls know fragrances like most guys know cars and games.”

“We can see if we can find an ounce or so at a reasonable price.” We talk a lot, mostly small talk, we check on Suzi as I listened for the baby again. I’m getting into the different baby watch activities. It’s three o’clock before we get to bed. I know she was up before six; I do good to trudge down by eight. Actually I’m wakened by Sherry jumping and hugging me. After a quick shower I’m dressed with Sherry hugging my legs, pressing her head against me. I get worried as Marti steps into the room.

“I hope that doesn’t bother you, she doesn’t see it the way we do, she’s carefree and innocent. If it bothers you we’d probably need to get a lock on the door to keep her out. But I’m more afraid of them locking themselves in some place.”

I put on a knit dress appropriate for the cold except it barely reaches the knees. I’m going with Sandy to church at ten. She says a missionary is to visit and they have a cute teen son who’s to be with them. She saw him two years ago and said he’s good to look at.

We’re there fifteen minutes early and Sandy’s brazen enough asking his parents if he can sit with the youth in the balcony? Tim just turned seventeen and there are twin sisters, fifteen that come with us. Two younger siblings stay with their parents.

Tim felt bad about me being pregnant; Sandy shouldn’t have told Tim the truth just before his parents are to speak. Tim’s outburst of laughter is very distracting and will probably land him in trouble. Later Tim’s parents are puzzled about what to say when someone says, “He goes against God’s teachings.”

Mr. Larkin’s response to the man was well stated, “God calls me not to judge and love without condition; how to do so is not so easy unless we retreat to ivory towers. I suspect it took a lot of nerve for Mel to take this step if his Dad offered to transfer him to another school.”

One of Tim’s twin sisters for whatever reason told me, “Do you know I’m old enough to have babies too.” I’ve heard similar statements from other girls, so I asked Sandy to explain their thinking.

“Their reacting to many people saying, ‘Women are suppose to have babies; some teens think if they have a baby it will prove they’re adults.’”

I tell her, “But that’s crazy.”

“We will see what happens when your romantic ideas of being a girl a hit an unexpected bump?” Sandy, nor Marti later, nor Mom or anyone, I asked will tell me what’s going to happen, neither would they deny something will happen that I won’t like.

It was the following day during my clinic appointment I get new tastes of things to come. My baby bump gets bigger and heavier as Dr. Kylie tells me I’m now expecting twins. My smile thinking it is funny soon leaves my face. Dr. Kylie attaches a tube from the baby bump and secures it to something on my vagina gaff. I hadn’t noticed it before. She tells me “Between now and three days into Christmas break your bump has a ninety percent likelihood of an occurrence of bleeding that will threaten the lives of one or both babies.”

My mind quickly shifts to a pregnant girl in my grade. I thought such a worry would be hard to accept at our age. I remind myself I’m just pretending, but it doesn’t take my worry away. Somehow it connects me to the babies I’m supposedly carrying. Dr. Kylie’s talking and finally she gets me focused back to what she’s saying. The Doctor says, “I appreciate how sensitive you’re being to this and not wasting our time. You are an unusual guy.”

I said, “I never intended to take it this much to heart, but I appreciate how much you’re helping me to feel the part. I’m afraid of showing up to the emergency room complaining about pretend problems. They will kick me out and laugh I’m sure.”

Dr. Kylie says, “Just the opposite, I and the hospital are set to treat it like a reenactment of the real thing. I hope you won’t be too scared. Your help could help prepare us for the real thing. When it happens to the young woman following you, it will be life and death, if we get it wrong.”

Again many questions go unanswered, but Dr. Kylie tells me she’ll tell me everything if and when problems arise…

Story to be continued…

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