Jack and Jill by Trudy – 23 – Arrived at Journey’s End

Jack and Jill by Trudy
– 23 – Arrived at Journey’s End

By JessicaC

Mr. and Mrs. Brandt had gone the second mile to make Trudy’s senior prom a special memory. Trudy would share a limousine with Denise. With Travis and I being friends, it promised to be a super night. It was 5:30 p.m. when Trudy stopped to pick me up for their promenade. Mom was the one to humorously give Trudy a hard time about how she treated Mommy’s little girl. I had gone back to Carol’s salon from that morning. Tonight was the first time with my hair done in this style and wearing my altered gown. There I was at the top of the stairs, in awe of how beautiful Trudy looked, yet feeling like a princess in my own right.

Each gown and girl was so beautiful and as agreed months earlier the gowns were exquisite together. When we posed for pictures, I could not help but feel Trudy’s right hand slide down my back and come to rest cupped around the cheek right of my bottom. We both used a quality lipstick that rarely left a trace on the other; even so we limited our kisses.


Travis and Denise had a wonderful time, yet regretted being with us. Trudy’s beauty and my notoriety took too much attention away from their enjoyment. I feared being with me had cost Trudy from being chosen as the prom queen. I had a great time, not only dancing with Trude but meeting more of her friends, becoming friends with them.

I wasn’t sure what to do when two girls as well as a guy asked me to dance with me. Trudy smiled and said, “It actually feels neat that they identify with us.” I danced with one of the girls and Trudy danced with the other. The guy was a loner who came despite being dumped by his date. I identified with him and gave him a dance.

We went to the After-Prom Party but we left at 3:00 a.m. Trudy took me to her home saying, “My parents would rather have us together here.” It was nice to be able to help each other out of our gowns and hang them up properly.

I had asked Sharon to instruct me on how to better love another woman and while she had clued me in on a few things, she mostly told me, “Listen and pay attention to the signs Trudy will give you. Women are different enough you need to remember you are making love to her. Even Trudy will want you to be sensitive each time. She probably will like something different from the time before. She is just as likely to love you in a different way.”

“It is not about loving her by the book but truly loving her.” I wasn’t thinking of Sharon’s words, I was making love to Trudy and responding to her body and what the sounds indicated as pleasing.


Trudy and I did not go to sleep by the time we got out of bed at 6:00 a.m. and we showered together. Trudy had agreed for us to meet several other friends and their dates for breakfast. Denise and Travis were there, as well as Cathy, Mariah and Lea and their dates.

I was going to the women’s room, when a college guy blocked my way and rudely said, “If you really want to be a woman, and you do look as beautiful as one; you should allow a man make you happy.”

“You are lucky I don’t slap you across the face. Even if I wanted a man you wouldn’t come close to being it!”

He responded, “Go ahead and slap me, I dare you.” I knew he was waiting to catch my hand if I tried. But when he stared at my right hand I just smiled and slapped him with my left hand and said, “Now would you please move.” He moved away, while others were quietly watching to see if things escalated.

I was in front of the mirror shaken when Trudy and Denise came in to check on me. Trudy stayed as I still needed to use the loo. It was nice to have her check my makeup and hair; more importantly to be with me as I went back to our table.


I owed my niece’s an appearance after breakfast; I promised I would stop by if I could.

Aunt Marti had a surprise for me when I did. The girls were ready for church or a Sunday out. Trudy and I doted on the girls and shared a little about the prom with Marti. Aunt Marti encouraged, “Stay and relax, we will be gone until the middle of the afternoon. If the phone rings let it ring.”

I looked to Trudy wondering if I should make sure of what I was hearing. Trudy smiled and just indicated me to be quiet and relax.

This time was a more quiet time of relaxing and giving each other quiet pleasures. I fell asleep by 10:00 a.m. and we both woke around 2:00 in the afternoon. When I got dressed it was into a casual dress. It would have been more relaxed if Trudy was not so stunningly beautiful.


The coming week was actually more difficult as I had to wait before I took Trudy to my prom. A disturbing piece of news was Trudy’s apartment at Columbia University had fallen through. Trudy calmly said, “There’s plenty of time; we haven’t even graduated yet from high school.”

With three weeks of school left, I was assured of the best academic year of high school. Mom told me it is confirmation that I was now whom I was supposed to be. My doctors tend to agree.

Mom had me to the Bridal Emporium saying my gown needed to be adjusted. The seamstress smiled as she already knew the changes needed: adjusting the halter enough to cause me to wear the gown braless. It is a stunning change and I am so excited to be able to look like a more mature woman for Trudy. Mom encouraged me not to tell Trudy. Mom knew I was taking Trudy to a place down near the ocean shore. When she sat me down for a talk it was mother/daughter with just a little caution about her son.

“This is awkward, but I thought you should hear it from me and not your sister. If you are intimate with Trudy, I want to suggest you not wear your breast forms at that time. Make sure you have the solution to take them off and to clean your breasts thoroughly to have an enjoyable time.”

“Mom, this is awkward I bet you didn’t talk like this to Richard or Sara?”

Mom just said, “Enough said. I do want you to know I love you and want you to have a beautiful time. Sara will go with you to your salon appointment. You have an extra three hundred dollars in your account for your debit card. If you want more just ask your father; he will be happy to go an extra mile for his youngest daughter.”

The truth was there was a pair of silver heels that I wanted. Not only would they go well with my prom gown but several other outfits I have or want to get.

My appointment at Carol’s Salon went well. I had talked with Sara as well as Carol. Along with the extensions I added some highlights. Sara continued to be amazed, saying my sense of fashion, hair and with makeup came to easy for someone who had been a boy.

We both knew that there was a girl in me long ago. While not totally shocked that I enjoyed dressing in girl’s clothes, neither of us expected in our wildest dreams that I was a girl. Sandy was a half hour behind me at the salon, but we would finish about the same time.

Sara had left and Sandy and I enjoyed our opportunity to visit during our time there. Sandy surprised me when she asked, “Would you mind coming back and being in my wedding in late September? I would like you to be one of my bridesmaids.”

“Does this mean I am a girlfriend for life,” I asked? Sandy answered “Unless you decide to become Melvin again.” Later Sandy said, “I would like to begin calling you Mel, if you don’t mind. As far as I’m concerned it is short for Melanie, but I’ll do as you want.” We talked and agreed to only use it among friends before graduation.


Ken, Sandy’s fiancé, was driving us tonight to the shore after the prom. I was picking Trudy up in Dad’s Chrysler 300. If I had still been Melvin I would have had to wash and waxed it yesterday. Today it was cleaned and detailed at a special shop. I had not seen it shine like this since the first week Dad had bought it. Dad offered to drive us for the promenade, around and to the prom. “Dad, I am neither a diva nor a defenseless little girl. I would take the car to the ocean if we didn’t have a ride already.”

Dad said, “In your dreams.” I battered my eyelashes at him and said, “I am sure if it were needed, you would let me use your car. I thank you and Mom for being so supportive.”

Mom and Sara helped me get into my gown and finish my makeup and check my hair one last time. I had to go to Sara’s room to use her full length mirror. I was stunned to see the transformation. I was dramatically more stunningly beautiful just since last week.

My drive to Trudy’s was uneventful; Dad had let me drive the Chrysler. I had grown confident driving with heels. The Brandt’s welcomed me and now it was my turn to be questioned Mrs. Brandt. She told how she wanted me to treat her daughter. She was very emotional, more than I had ever seen her about her daughter. Something had set in how precious her daughter really was. I knew she and her husband were proud of Trudy, but today their love was much more evident. I was not sure if something had happened or what. It became apparent that whatever it was it was welcomed by all three.

I was happily excited as Trudy stepped into the living area. Like me she had taken extra effort to be even more beautiful than last week.

It was my turn to pin her corsage on her. It was no small feat as the gown’s strap was narrow. It was now her parents’ turn to take a ton of pictures. Mrs. Brandt even was sending them on to my folks.

I drove us around and Trudy said, “We have to go to the store to show off Jack and Jill; she told me she had promised. Hannah’s husband the major owner of the store and the chain of stores; he wanted us to carry a bucket around the store. I said, “No” and luckily Hannah hurried to agree as she took the pail. We were given three long stem roses each.


We were to the promenade a few moments later. The Principal came over and threatened, “I am going to introduce you as Melvin. I hope don’t mind but it’s too bad if you do because I’m free to do as I wish.”

When Trudy and I stepped out of line before our introductions, my Dad and Ms. Braun were soon there asking what was a problem. “Dad or Ms. Braun have you seen Nancy Parsons or one of the other Board members. Mr. Lawrence is threatening to taunt me as Melvin if we go through the Promenade.”

Dad quickly said, “I don’t think so unless he wants trouble with me.”

Ms. Braun had quickly text Mrs. Parsons and she was soon with us. She confronted Principal Lawrence, “Let me see your introduction sheet for this young lady and her date.” He was arrogant enough to have it in black and white. “Mr. Lawrence, I will keep this and share it with the Board at our next meeting. I am glad you have held up signing your contract to get a raise.” Mrs. Parsons took over the introduction of couples as we were back in line.

Trudy gave me a hug and a light kiss on my ear, “I am so proud of you for standing your ground; I would have been embarrassed for you.” It was nice as we were the third couple Nancy Parsons introduced. One could tell some people went quiet and a few murmured, possibly negative things. But the cheers that started by Sandy, Sharon and Deb brought even more applause for Trudy and me.

I wouldn’t have heard it before as a guy, but it delighted me now to hear compliments on how beautiful we looked, about our gowns and how they complimented each other so fantastically well. The nicest compliment I heard went something like: “If there were any questions about being boy or girl it’s mute now, Melanie is a beautiful young woman.” I looked up to the woman I thought said it with a light smile. It was Ms. Brownlee. She smiled at me and said, “I hear you are a beautiful person as well. I hope you two enjoy your evening.”

Once through the promenade, we talked with others about driving around before heading to the Prom yet an hour and only a fifteen minute drive.


Nana’s, one of my grandmothers, lived but a few minutes from the ballroom of the large Hinton Hotel. Nana would probably still be with my folks; maybe even spending the night. But it would be okay to be there. It gave us a chance to relax, be affectionate and able to redo our makeup and check our hair. It felt wonderful to hold Trude and allow my hands to run down her gown.

Trude loved the feel of my back as we swayed together like music were playing and we were dancing. I bit my lower lip, not wanting to get too excited. But I was getting hot and moist. It was good to hear my grandmother’s car. I went into the bathroom to fix my makeup and regain my composure.

Nan had recognized the car so she was not surprised to see Trudy. I was pleased as Nan spoke to Trudy, “You are very beautiful tonight Trudy. There is no trouble in seeing why Melanie cares so much about you. She is fortunate to have someone like you who loves her.”

I walked into the room, “Thanks Nan, I think she’s fantastically beautiful inside and out.” Nan broke in “And she has a beautiful girlfriend as well, though I know I am prejudice. You have blossomed so much since you were first Jill.”

“Did either of you have any idea that a young woman would come from that?”

“Only in retrospect Nana,” said Trudy. “We always were special to each other. When I dated Melvin there was something I loved but it wasn’t him. When I related to Jill, I found the something that was missing. She wasn’t like another good friend. Finally, we kissed and I felt her body against mine. I looked into Melanie’s eyes and I could see she was there. I never saw me as loving another woman. I guess I didn’t want to admit I’m a lesbian, but I am and I’m getting more comfortable with being me.”

I was surprised Trudy dared to say that to my grandmother.

Nana’s confession shook me even more, “I understand what you’re saying; I could have loved and married my best girlfriend. She too married someone else, though we have always kept in touch since I moved away. Ezekiel, God bless him, came to know I loved her. …Melanie, I ask that this remain between us three.”

“Thanks Nan, would it be alright if I/we came back sometime to talk more?”

“That’s why I said it; you need to know you two are the only ones. It will be helpful to me to talk about it as well. Please don’t speculate about my love; I’m not sure she’d want anyone to know.”

“I’d of guess it was Sue Ellen. She’s the dearest of your friends as far as I know.” Nan wouldn’t say anything, but her expression indicated it probably was her.


Trudy and I felt even more excited as we drove to the Prom. I had text and Sharon was there and Sandy and Ken were on their way. Deb and Chuck had gone in as had Travis and Denise. Trudy giggled, “Just think if your Nana and her friend became a sole item you wouldn’t be here.”

“Does that mean you want each of us to marry a guy so we can have children,” I asked thinking I caught her.

Trudy spoke right up, “I thought you said Dr. Karen had harvested some of your sperm just in case you became infertile but still wanted your own children?” It dawned on me how seriously Trudy had been thinking of our relationship. I reached over and squeezed her hand. This time when we parked, it was I getting out and going around opening the door for Trudy. We had agreed to that last week.

I was so proud to have the most beautiful girl on my arm. When we were introduced at the Prom, I saw a jerk coming running toward us. He wasn’t a friend and he had a cup of something in his hand. I hurried and threw my three roses at him as he began to throw whatever was in his cup at us. Luckily the roses hit the cup and liquid and no more than a few drops of cola reached me. Someone quickly handed me a cloth and I dried my face and front.

It was Nate, supposedly an old friend. I knew he was more rigid in his faith than I was. But I never expected this from him, especially against me. I was asked, “Do you want him thrown out of the Prom?”

“If he can promise in God’s name not to bother Trudy, me or anyone else that will be okay with me. But is he can’t or the rules would mandate him leaving so be it.” Trudy agreed but added, “It shouldn’t be our responsibility to watch and stay away from him. That should be his responsibility. We’re sorry if that ruins it for Sally, but that is his doing, not ours.”


A half hour after the King and Queen of the Prom were selected the Queen brought the prom to a halt having an announcement to make. Queen Ashley with a big smile proclaimed, “Though there was no official balloting and there could have been other candidates; King Richard and I would ask for confirmation to select Melanie Greene and Edward Langer as Duchess and Duke in a spirit of inclusivity.” I recognized Sandy’s voice as one of the first to say “Aye!” Instead of a crown, I had to curtsy before the Queen as she put a pendant around my neck. Ed was given a double strand gold chain necklace. Ed and I began the next dance.

It was a wonderful evening. I had not gone to the prom as a junior. My date last year had decided not to go, so neither did I. It wasn’t until this spring; I learned Rachel had gone with a boy from another school.

Once I had to go to the women’s, but I had left Trudy at our table. When I got to the women’s room I became very self-conscious what others might say. I looked neither Sandy, Deb nor Sharon was around. A friend Linda noticed, “So girl, do I need to take you by the hand or are you going to wait until your eyes turn yellow?”

We both giggled as I offered her my hand. “Thanks Linda, after earlier I’m still worried about someone saying something.”

“You don’t need something different to find people judging you, however I understand. I would like however if I could double date with you sometime before you go to college.”

“I would like that and I guess our friendship has changed since last year. We could go shopping sometime; I’m more into that now.”

Linda watched me when I fixed my makeup. “I’m impressed how well you do makeup and hair. If I didn’t know better I’d swear you grew up a girl.”

While we talked Trudy called, “Did you fall in or mess yourself?”

“No, I am chatting in here like a regular girl, what’s it to you?”

Linda got her date Brett and came over and visited awhile. It was a great night for being affirmed that Trudy and I were normal human beings. Not that everyone was kind like that but…”

We had to go to my home so I could drop off Dad’s car and get my overnight bag. When Ken and Sandy showed up, Dad offered his car again. Kenny’s face lit up, “Your Chrysler 300 Mr. G are you sure?” Dad threw Ken the keys, “It might be better if Melanie drives it until you’re out of site, but yes enjoy yourselves.” Dad had actually known Ken more and longer then he knew Sandy; he felt safe that we were riding with them.


We were half way to the shore when Trudy and I unzipped the back of the other’s gown and got very friendly. I looked up and could tell Ken was smiling. “I hope you don’t mind us back here?”

Ken snickered, “It’s just a shame I have to drive. It is not the first time I had friends making out in the back seat.”

Sandy whispered back to us, “It is more pleasant hearing you two and not some of his gross friends.”

Trudy switched positions and pulled the top of my gown away from me. She swore, remembering I still had on my breast forms. She helped get my gown back into place and it was now me being the aggressor. It was beautiful to see and feel Trudy’s nipples become aroused. The first time my kissing and sucking Trudy’s nipples made a noise; it brought a noticeable giggle from Sandy.

Ken alerted us when we were within five minutes of the hotel. Our hotel was on the other side of the street from the beach. Come tomorrow night the beach might be more interesting. Trudy had other ideas. After we checked in and were out of our gowns; Trude encouraged me to put on a short skirt, top and sandals. We walked the boardwalk and until Trudy saw the shore patrol.

“Officer, would it be okay if we walked the beach?” I expected the answer to be a curt ‘No’.

“If you’re a couple the answer is okay, though I need to ask you to respect others who are down there. You’re asked not to go into the ocean and it won’t be patrolled for safety unless there’s a problem. If that happens everyone leaves, do you understand?”

We found a spot fifty feet from the closet couple and along the side of a lifeboat. I soon discovered why Trude had me wear a skirt. I became aroused and had an orgasm but it was unlike a normal boy. I had also taken off my breast forms at the hotel. My sensitivity to Trude’s hands and lips experienced a world of difference. It ended up being with the first light on the horizon that we and others still on the beach made our way back our hotels to sleep.

Trude and I showered together and then fell asleep in each others arms. It was noon with a knock on the door that we finally scooted out of bed.


The ocean is very cool in late May; however it was a rare treat to be in the ocean without young children or younger teens being there. I began to complain until Trude shut me up by locking lips with me. “If you say you’re cold with me next to you…” We didn’t stay out long but even with the cold water I became aroused and knew Trude shook because of an orgasm and not the cold water. Luckily the temperature was into the low 80s. Once we were dry we were also warm.

Trudy and I were walking the boardwalk and Trudy was looking for a place but would tell me what. I walked on not noticing when Trudy went her own direction. I back tracked when I did, but didn’t find her and had to wait. Finally a text came, “You passed me twice; I’m in Pt. Pleasant’s Gem Stone store.”

I walked into the store and wondered if I heard wrong, since Trude was nowhere to be seen. I asked a sales person as I felt a tap on my shoulder. I turned around and had to look down. “Your Dad and Mom said I should only give you a promise ring. I want to know if you’ll marry me.” Trude had a ring box extended to me.

“No, that’s not fair; I don’t have a ring for you and I can’t afford one.” It was then I saw Sara step forward. “Mom said you might say something like that. They sent me with their card and this note.”

“Dearest Melanie, if you feel compelled to accept Trudy’s proposal and want to buy a ring for Trudy; up to fifteen hundred dollars on this card is for your ring for Trudy. We love you very much.” I know Mom and Dad think it is too early.

“O Trude, do you forgive me? Yes, I will marry you. Will you be my wife?” We were locked in a warm embrace both saying, “Yes, yes, yes,” over and again.

I had not been one to notice engagement rings before Sandy’s, but this one was beautiful. Sara helped me to pick one but my heart was broken as it cost $2,185 before taxes. I asked the jeweler if he could give me fifteen to thirty minutes. And then I called home.

“Dad, please listen to me, I need your help but not a hand out. Sis’s car is a clunker, and my Camaro is up on blocks because of my driving record and the insurance cost is way too high. It doesn’t really pay to have a car in the city anyway. How about if I sell my car to you for Sara? That will allow me to buy the ring I want for Trudy. I thank you for the offer to pay for it, but it needs to be my ring to her.”

“The money already on my bank card can be for college along with the remainder of the $6,500 for the car.”

Dad said, “I’m proud of you Mel, for taking responsibility for your engagement with Trudy.” He gave the phone to Mom, “Congratulations Honey, I am so happy for the two of you. Were you able to find a beautiful ring for Trudy?” She was tickled when I was able to describe the ring fully.

“Mom and Dad can I tell Sara, she’s getting my car. It’s important to me that Trude and Sara both know the ring is from me?”

I bought the ring I wanted and Trudy was pleasantly surprised as she learned what I did to buy it for her. The rest of the day and into the night we celebrated our engagement as well as prom weekend. After we turned in, the real celebration between Trude and I started.

The End

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:
110 users have voted.

And please, remember to comment, too! Thanks. 
This story is 4744 words long.