Happily Ever After Pt. 01

This is a follow up to Finally a Princess which had six parts. You do not have to read that to follow this. I incorporated the back story into part one of this series. If you really want to get to know these characters though you would probably want to start, there. This story is either Pre-COVID at Disney or in a world where COVID never existed.

Happily Ever After- Finally a Princess at Disney World Part 1

I was in the kitchen when Sarah got home from the grocery store. She carried the bags in and sat them on the counter as I started to organize them and put them away. It took her numerous trips to her car to get all of them. On most days I would offer to help her bring them in but today I did not want to step out of the house and risk being seen by neighbors.

It was October and the temps had cooled, not helped by it being a rainy day. I had been working out when she left and after a shower, I put on a pair of Disney LuLaroe leggings with a Sea Foam Disney Cruise spirit jersey. The spirit jersey was the one that Sara had bought for me on our last cruise. The same cruise where it had been revealed that I was a lifelong crossdresser who, up until that point, had been deep in the closet.

Sarah and I were Disney fanatics, having annual passes for Disney World and going on Disney Cruises frequently. Early last March we had treated our friends Pat and Jordie to a Disney Cruise with us. On that cruise I was initially led to believe that I would need to borrow clothing from Sarah because my luggage had been lost. I slowly revealed to Sarah that this was not my first-time wearing women's clothing, eventually she confessed that she had worked with Pat on setting this all up. Sarah had discovered I was crossdresser and used the cruise as way to get me to confess it and lure me out of the closet. They had secretly brought a lot of my own stuff and in a lot of ways Brandi, the name I liked for when I was dressed, was born on the ship. It was five of the best days of my life.

Pat was a lifelong friend of both me and Sarah. She was divorced and worked hard at her job as a hairdresser. Her daughter Jordie, a single mom of two young daughters, had been forced to move back in with her mom after she had gotten divorced. She sold LuLarou and Faramisi cosmetics to help her mom with living expenses. Between the two of them they made just enough money to keep a roof over their heads, buy food, clothing, and other essentials. On the cruise Pat had been my personal hairdresser and Jordie my makeup artist. After the cruise I now considered Jordie a close friend and not just the daughter of a friend.

I had burst out the closet on the cruise with a lot of support from Sara and our friends. While Sara had been supportive and encouraging of my crossdressing and other experiences on the cruise, there were areas of friction. It was now seven months later, and we were still working through those areas. One of the biggest problems was trying to figure out exactly what were the boundaries of when it was okay from me to go from being Brad to Brandi.

If it were up to me, I would probably be Brandi most of the time. If it were up to her, I would only be Brandi on rare and special occasions. In fairness on those special occasions, since we had come back, she was incredibly supportive although she still always managed get some digs into me.

After we finished getting everything put away, we moved into the family room. The TV was still on and the screen displayed a video from Disney World. It showed the sidewalks of Main Street packed with people who looked to be waiting on the parade. A man and woman were standing in the middle of the street and a Disney Photopass photographer was seen taking pics. The man suddenly sank to one knee and it was obvious he was proposing.

"What are you watching?" She asked.

"Umm... just some Disney Youtube vids." I replied reaching for the remote.

She was closer than me and reached it first. A couple of clicks later she could see that I had searched Youtube for Disney World proposals.

She turned to me and shook her head. "Really, you were sitting here watching proposal videos, again? How many of these have you watched? It seems like you are watching these all the time. You are such a girl!"

That had started to become a favorite saying of hers. Sometimes she said it was a big smile on her face but most times, like now, she said it with a look that let me know it was not meant as a compliment. It was true though; I did love watching videos of proposals that happened at Disney. She grabbed the remote and began to channel surf, stopping for a minute on an episode of Say Yes to the Dress. That had always been a favorite of mine even before coming out to Sarah as crossdresser.

She looked over at me. "I am sure this okay with you to watch."

"That is fine, you know I have always liked this show, but whatever you want to watch is okay with me." I was hoping that would lighten the mood.

"I guess you haven't gotten the wedding dress fantasy out of your system, even with what Jordie set up for you last month." She set the remote down and left the show on.

I chose not to answer because I did not want to cause an argument. I was also fondly remembering what had been, for me, a perfect day last month. Jordie had a friend who worked in a bridal boutique and had arranged for me to have my very own wedding dress fitting after the store had closed on a Sunday. Pat had done my hair for the occasion and Jordie did my makeup. They had all offered their thoughts on the different wedding dresses I tried on. Sarah was good natured about it, but she occasionally appeared uncomfortable, Pat provided her wonderful laugh and lots of smiles as I modeled different dresses. It was Jordie though that really made the whole experience so enjoyable, because of her there were a couple of times I almost felt like I was, a bride to be, choosing my dress.

After almost two hours I had finally picked a favorite, it was mermaid style dress with three quarter sleeves, lots of lace, and some light beading. When I saw myself in the mirror I teared up. I wanted to buy it but could not justify spending $5000.00 on something I would only wear occasionally in the house. Sarah and Jordie took a ton of pictures and I decided I would settle on the memories of the day and have the reminder of it with the pictures they were taking.

"No, probably not but that was a wonderful evening, thank you for being a part of it. I know that we are still trying to figure all this out, but I really appreciate everything so far." I looked right at her as said it and we both smiled but you all also see a little sadness behind our smiles.

"Well, we have this months big Brandi event coming up in two days and you have to be excited about that right?" She said and the mood did lighten.

This was part of the problem in where we currently were at. The day to day was a struggle in trying to figure out how this fit in our life. On the other side Sarah was enthusiastic, although often sarcastic, participant in the big events like the bridal boutique.

"Oh, I can't wait. Although I would be excited about this whether I was going as Brad or Brandi, you know that, but a whole week at Disney World as Brandi, yea I am excited." I was practically shouting my response to her.

After the cruise we had told Pat and Jordie that we wanted to take them to Disney World, along with Jordie's daughters, the following year. It was Sarah's idea that I make at least one trip there as Brandi. Pat and Jordie had been so supportive of my crossdressing on the cruise we thought it would be great to treat them and take them with us on Brandi's first Disney World adventure.

Jordie's ex had thrown a fit about it and said that he wouldn't let the kids go unless he was part of the trip. She did not want us to pay for him, and didn't want to subject Brandi to him, primarily because she was certain he wouldn't keep it to himself. In August, Disney announced the Fall Passholder discounts and they had a great deal for the Port Orleans French Quarter Resort. That was our favorite, what Disney termed moderate resort, so we booked two rooms for the week and asked if Pat and Jordie wanted to go.

At first Jordie said no, that she would feel really guilty about her kids not being there, but we convinced her that this would be a more adult oriented trip, and that she could use it as a scouting and planning trip for when she brought the kids. She eventually agreed and we set up the late October plans.

"Did Lisa ever let you know if they would be able to meet us there, even if just for a day?"

I responded. "Yes, she hasn't completely blown it off, but she keeps saying that the business is so busy they just don't think the can get away, especially since they are doing back-to-back cruises in November and will be gone for two weeks then."

"I know you are disappointed. Maybe you should reach out to Steve directly, even offer to sneak out for a quickie in his car in the parking lot, or at least offer him a blow job, I know how much you liked sucking his dick." She smiled as she finished talking, gave me a wink, and her tone was friendly as she said it.

On the cruise we had meet Lisa, her husband Steve, and the rest of her family. Steve had shown some attraction to me, especially my ass and legs. For a man I have a pretty nice butt, the result of some good genetic and a ton of squats. My legs looked great from hours on the stair machine. Lisa had told me that she and Steve and an understanding. He was allowed to get blow jobs and have anal sex, occasionally, with other people because she didn't like doing either one of those things. In return she could in her words- "suck on titties and lick pussy" because Steve did not have those.

As part of my confession to Sarah about my crossdressing I had admitted that I was at least curious about sex with a man. While I think she was a little shocked by that, the truth was that she and I hadn't had sex in several years. We got along well, enjoyed each other's company, especially traveling together, but there was little to no intimate contact between us. In fact, we had shared more hugs, in the five days while I was dressed as Brandi on the cruise ship, than we had in the last couple years. She had also told me, paraphrasing her words- "Brandi could get as much dick as she wanted but that Brad couldn't, and Brandi wasn't allowed to be a lesbian."

This had led to me and Steve developing a relationship and yes, I had given him several blow jobs during the cruise. I had also lost my anal virginity to him and he fucked my ass twice, the last time we had stayed the night together and I admit I had very much enjoyed being the little spoon as I drifted off to sleep.

The big irony was that Lisa and I had become close friends despite me sleeping with her husband. After the cruise we texted almost daily and shared stories, jokes, and memes. She especially enjoyed inappropriate adult Disney memes and sharing pics of hot men, mostly firemen, cowboys and construction workers. I had shared some texts with Steve also, but it was pretty rare, I had even sent a couple pics of me in lingerie, and he responded with dick pics, we had also sexted a couple of times. As time had gone on that had slowed down and it had easily been a month since I had heard from him.

I decided to fire back at Sarah's comment about hooking up with Steve in the parking lot. "You know why go all the way to the car in a hot parking lot, I could blow him or just straddle him and ride his dick while he sat on toilet in a family restroom at the park."

Her eyes widened as I said that. "Well, you were definitely a cum slut on the cruise ship so I am sure you could fall right back onto the whore wagon."

Sadly, instead of seeing that as an insult it aroused me, and I thought I might have to find a little time with one of my toys I had hidden in the closet. I also knew that she had gotten the last shot in and won this little skirmish. It was another reminder that we still hadn't found a comfortable place for Brandi in our day to day lives.

The next day I went for a long run in the morning, followed by a bunch of squats and planks. I was trying to keep my girlish figure. I had stopped working out my arms as much, in an effort for them to be a little less bulky so they would look better in sleeveless dresses. I was glad to see though that more and more women were proud of how working out made their arms look and mine didn't stand out nearly as much as I thought they would.

I am five foot nine inches tall and weigh about one hundred and seventy pounds. It makes me tall for a woman, especially when wearing heels, which I love to do. I can pass and blend in, but I am always conscious of my size.

Sarah was a night owl, so she had slept in. A few years ago, because of her snoring and her restless leg syndrome, we gave up on sharing the same bedroom. At first, I thought that maybe that contributed to the reduction in intimacy between us, but the reality was, that wasn't it. I think that part of our life had just run its course. Because that wasn't a part of our life, I sometimes struggled with why she cared what I wore or even who I was interested in sleeping with.

I decided I would begin packing for our trip. I had consulted Sarah weeks ago on what I would need. Having never been to Disney in girl mode before, I wanted to make sure that I packed the right things. After a few smart-ass comments along the lines of, if I left my cocktail dresses and fuck me heels at home I would have about one outfit to wear, she finally gave me some real advice.

I had ordered a few pairs of leggings from Jordie's Disney Lularou stuff, along with ordering some cute dresses, from the Shopdisney site. I also got a couple of Disney themed running skirts, and a few pairs of shorts to go with my growing collection of Disney Princess themed t shirts. I was thinking the shorts or leggings and t shirts for the day in the parks. Then the skirts or dresses in the evenings, for visits to Disney Springs, and especially for the dinner at the Yachtsmen Steakhouse. In my opinion the best restaurant in Disney.

I had bought two pairs of Converse Disney themed sneakers, along with a pair of pink and purple women's Asics. Those would be my primary park shoes. I would save the converse and the one pair of strappy flat sandals I was bringing for the evenings. I had also managed to add a few pairs of Minnie Ears to my collection and planned to color coordinate those with my outfits each day along with my Magic Band. I also had a few more pieces of Disney jewelry including earrings now.

The earrings, longer hair, and keeping my legs and underarms shaved had caused some friction with Sarah. She was worried that I just kept pushing my look and eventually our adult children would wonder what was going on. I just passed it all off as being because of my bike riding and swimming exercises along with a bit of a midlife crisis, plus going a little hippie, because I could, kind of thing. So far it hadn't seemed to cause a problem.

I heard Sarah as she came in behind me, having just woken up. I was a little worried that as she saw me packing the suitcase, we were going to start the morning off on the wrong foot. This would be our second trip since the cruise that I had spent the entire time cross-dressed. The first one had been a long weekend to Atlantic City. The time I had been able to pack some great dresses and heels, although Sarah said I had been overdressed the whole time.

"Good Morning, how did you sleep?" I asked.

"Fairly, well at least compared to normal. Thanks, how about you?" Her tone was pleasant.

"Okay, starting to get more excited about the trip." I replied.

"Yea, I can see. Packing already." She scanned what I had laid out. "And it looks like you are following my advice on sensible clothing and shoes."

I laughed. "Yes, I do listen to you, at least most of the time."

She smiled back at me and I continued. "What are you going to wear for the flight down? The plan for that day is still just an hour or two at the pool, and then Disney Springs for dinner the first night, right?"

We had a noon flight, which put us in Orlando at about two. After the Magic Express bus ride, it would be between three and four before we got to the resort. A little pool time and then dinner around seven thirty or so. We were going get to bed early so we could rope drop the Magic Kingdom on the first full day.

"Yes, and I am going with leggings, my park tennis shoes, and a long sleeve t shirt. I will probably throw a tee shirt into my carry on just in case it is really warm when we get there. Although the forecast for the week is great. Low to mid 80s and sunny pretty much every day I think, a little cooler the first day at the Magic Kingdom."

"Let's hope that is accurate. Okay, I think leggings for me and probably a spirit jersey, tennis shoes are a good idea for the airports. And I will pack a t shirt in my carry on along with my bathing suit and flip flops, if I don't need to change because I am too warm, I can wear it as a cover for my bathing suit."

"That a girl, you really are starting to think like a woman. Have you had breakfast yet?" Sarah asked.

"No just coffee, I was going to make some toast in a little bit."

"Okay, I was thinking we could possibly go to Panera for lunch and then I have a surprise for you scheduled at one thirty. You will probably want to go as Brandi for it, casual Brandi. Like t shirt, shorts and flip flops casual if it is warm enough. I don't think it is supposed to get cold until tonight."

"Sounds good. Thanks."

When she left, I was back to the ongoing level of confusion. Yesterday, it seemed like my crossdressing was an eight-hundred-pound gorilla in the room. Today she seemed eager to be going to Disney with Brandi and had a surprise planned me. I really hoped we could find a comfortable place for this part of me. When I thought deeply about it, I understood it was a lot to ask, I mean not many women would be really tolerant of their husband trying to out girly them, let alone being more interested in getting dick than they were.

I ate my toast and some yogurt and finished the coffee. Sarah had a breakfast bar and then went and showered. After cleaning up the kitchen I headed up for my shower. After I finished that I tried put my hair up into a very short, high ponytail. Unfortunately, it still wasn't long enough for that so it just I just let lay flat and tucked some if behind my ears. For my makeup I went with a touch of eye liner and mascara, a light coating of lip stick, and then added some small gold hoop earrings. With the towel up around my chest, a quick glance at me would make you think woman.

A pair of yellow bikini panties and a matching bra were next. Setting my forms into the bra, I pulled on a pair khaki shorts and lavender women's cut t shirt. With the clothing, boobs, and make up I would stand up to a little longer glance of being seen as a woman. I had learned since returning from the cruise that blending in and passing were a function of wearing appropriate clothing for the activity and projecting yourself as a woman.

I think part of the problem that Sarah was having, besides the frequency that I wanted to spend time as Brandi, is that I was getting better and better with my movements and mannerisms. I had also worked on my voice and while far from perfect I was no longer scared that it would immediately give me away. I had tried to discuss this with her, but she just kept telling me that I need to find myself and what I wanted or more importantly needed.

"Are you ready?" Sarah said as she made her way downstairs.

"Yep, just need to grab my purse." I responded.