Becoming Cassie Ch. 04

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

When I got home my mom was waiting for at the door to give Kate a hug as she headed back to school.

When we got inside she looked at me and said, "I am so proud of you. Your Aunt Mary called me and told me what a big help you were to her. That is so nice. Thank you." And she gave me a big hug.

++++++++++++++

On Wednesday my mom got a call from Aunt Mary asking if I could give her a hand one day this weekend for just a few hours. There were still a few heavy chores that she could not do herself and Kate was back in college until the Thanksgiving break. My mom volunteered me but needed to check my hours.

The next Saturday morning was out for me but I had time in the afternoon. That worked out perfect because my mom had to drive my little sister to a 2:00 party and she could drop me off and pick me up at 6:00. (My not having a car was a pain in the neck, but I had saved almost enough to but one.)

I had a feeling this trip over to see Aunt Mary was going to be different. Kate said her mom was my biggest cheerleader and knowing what her birthday was like, I had no idea how she could top that.

"Hi Matt, so glad you could come over on such short notice. I really do have some things I need moved. You know the tables you and Kate moved downstairs in the rain on Saturday? We need to put them against the back wall. They are in the way of everything...that was quite a day in the rain as you recall."

"I sure do. I'd be glad to, anything else?"

"Yes, there's still that one big box I would really love you to go through with me, the one with Kate's dresses in them. I would like to donate the rest of them tomorrow to our local church group that's sponsoring a program to help needy girls."

"We got so rushed last weekend that I feel bad I was not there to help you. Would you feel up to having a little Cassie time today?"

"I was hoping there would be time for that. Let's head to the basement see exactly where you want them."

It was easy to see in hindsight the tables and chairs were a mess. Kate and I worked so hard and fast to get them out of the rain that I never really looked at what it looked like. Aunt Mary showed me where they usually go and I got to work as she headed upstairs.

It was a relatively easy task. Since the tables were downstairs already, moving them and restacking them and the chairs in the proper place was easy. I barely broke a sweat but it still some took time.

When I got upstairs, Aunt Mary had already laid out the 12 dresses that Kate no longer wanted on the bed.

"Seriously, 12 dresses?" I asked.

"She does love her clothes. Do you need a minute to change in private?"

"I do, but which bra and panties do you think I should wear today?"

Aunt Mary said, "Let me check your drawers for a moment." That sounded so nice, my drawers.

She selected the floral panties she liked so much and a slightly padded ivory bra. "I think these will be best for today, and take this robe as well."

I walked down to the bathroom, removed my clothes and slid on the bra and panties. But there was something wrong. There was no immediate rush and when I looked in the mirror all I could see was Cassie. In some regards this was real good, because I did not need to be hiding a hard on all day with my aunt.

When I walked back in she said, I want to give you a little make-up and put on a wig so we can see what these dresses really look like.

Unlike the quick time with Kate, Aunt Mary spent a lot of time of my foundation, blush, eye shadow and lipstick. I knew it was going to look good. She then put on the wig and as an extra surprise had some clip on earrings. That was a real nice touch.

"Cassie, no looking until the first dress is on. Agreed?"

With that she helped me stand up and helped me with the first dress.

"I bought this red dress with Kate for a Valentines Party she was attending at school. I loved the embroidery on the bodice and the flared skirt below. She wore it all of one time, so this is the second time it's been on."

As I turned to the mirror I gasped at not only how well the dress looked but how nice the make-up was.

"Aunt Mary, you did a beautiful job on my make-up", and I gave her a hug.

"You've got eyes just like Kate, I never realized it until I was doing your make-up. Oh, and here, see if these shoes fit."

Aunt Mary brought over a Payless bag and took out two pairs shoes. "Payless was having their "BOGO" sale, you know, Buy One Get One, and I couldn't pass these up. I got one set of strappy heels...put these on, and a pair of wedges. I think they should both fit."

Stepping into the heels brought me back to the prior weekend when the Warrens surprised me with a pair. As I slipped these on and stood up, Aunt Mary said..."Perfect. Let's try walking in them...that's always a challenge."

I loved the heels but had to fake a little unsteadiness. I didn't want to take away the fun for her.

"May I take a minute and walk around the house?" We did and we chatted as we did. I even sat in chair as she instructed me on how to sit like a lady in the dress."

"Cassie, we have 11 more dresses to try on, so if you are ready, let's do continue."

We went from casual to formal. There were short party dresses and even a long maxi-dress. I actually liked all the casual dresses best because they seemed, well, normal.

It took two hours to try everything on. But that was really quick when you think 12 dresses, ten minutes each, and that's 120 minutes or two hours. And out of twelve dresses I wanted 9 of them, or stated differently, I didn't want 3 because of either the fit or the color.

It was so much fun not only trying them on but also hanging them up. Aunt Mary kept referring to it as my closet.

"Let's see, it's 4:30 right now and your mom is picking you up after 6:00. May I make you a snack and maybe we can chat for a while before you need to change?"

"I would love that. Which dress would you like me to wear Aunt Mary? You've now seen them all on me."

She went to the closet and selected a light floral print dress. "This was a spring dress and it was my favorite on her. I remember she wore it for Mother's Day when we went out for a lovely lunch. Please wear this one."

Aunt Mary helped me changed one last time and we headed to the kitchen. She made some tea while I put out some light snacks.

She reached over and grabbed my hand and said, "Cassie, this has been a wonderful afternoon. I know it's probably not as much fun as being with Kate, but I would love you to come over anytime you feel you need some Cassie time."

"Whether it be just to dress up on your own, to show me some new things you might get, or even to talk. I'm here all the time and I would love your company."

"Aunt Mary, I promise you I will come over. I have loved my time with you as well."

As we approach 5:15, she said it was my Cinderella time to change back. She helped me remove the make-up which was not easy.

It was sad hanging the last of the dresses up and putting my underwear in the hamper, but as we did a last tour of the room, I could not help think of all the nice clothes I now had anytime I wanted. And it was a nice safe feeling.

All changed, I moved the boxes she was going to donate out to her car and waited for my mom. As Matt, she and I talked about Matt things...school, my sports and my brothers and sisters. Mom arrived right after 6:00, and tooted the horn.

I gave Aunt Mary a long hug. Even before I left, I was longing to come back.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
8 Comments
AnonymousAnonymousalmost 8 years ago
Thoroughly Enjoying This!

I have to agree with the other comments. This has been a wonderful read and I love how Cassie is taking a break from sexual pursuits and focusing on the more emotional side of her transition by learning of her past. Your writing has been an inspiration. Thank you.

AnonymousAnonymousabout 9 years ago
You're work is amazing

Please continue this story. I would love to see her come full out and live as herself. Your detail is wonderful I love knowing the color cut etc of her panties bra clothing etc. Please keep this going. I keep checking every day to see if there is a new chapter. Thank you

mumblegooseeggmumblegooseeggabout 9 years ago
Better and better

The episodes with the Warrens were exciting and arousing, but maybe a little bit over the top. This seems to return to a more real-life story and I have no doubt sex will eventually work itself back in the storyline. I'm a sucker for this kind of slow romantic tale!

DaveXX80DaveXX80about 9 years ago
Terrific!

This was another terrific read. I loved it. You did a great job bringing in Cassie's history with Kate and Aunt Mary. And it was great how accepting they were of Cassie. Definitely looking forward to the next installment.

AnonymousAnonymousabout 9 years ago
so good

no sex in this one but the character building and the natural transition from it being a "sex thing" only to being a "her thing" it is so great that she has a safe place to just be Cassie. the warrens give her something she craves and aunt marie and kate give her, her normal

please keep this going, you have a nice balance here.

kisses.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
Drink or Dare A drinking game with new friends changes everything.in Transgender & Crossdressers
Like Mother, Like Sissy A sissy learns he is a princess . . . and a sperm whore.in Transgender & Crossdressers
Caught by my Sister Young man caught in his sister's pantiesin Transgender & Crossdressers
More Stories