Finally a Princess Pt. 01

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A Disney loving crossdresser steps out of the closet.
9.5k words
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Part 1 of the 6 part series

Updated 06/10/2023
Created 08/01/2020
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The first part, of what will be a multi part story, of a crossdresser who loves Disney getting to step out of the closet. I like to develop the characters so if you are hoping to get straight the sex you will likely be disappointed.

Finally a Princess (Part 1)

You could feel the excitement on the bus as it traveled along the highway. The video showed a bunch of activities that waited for everyone once we got to our destination. We were headed to Port Canaveral and onto a Disney Cruise Ship. Sitting across from me was my wife Sarah, in front of her was our friend Pat, across from her was Pat's daughter Jordie. We were kind of an anomaly on the bus, all of us being adults. My wife, Pat and I just having passed fifty and Jordie was celebrating her 30th birthday. This five-night cruise was kind of our birthday present for her. It was a generous present, but we were very glad to do it.

For about the third time Pat asked. "Our luggage will be brought to our state room, right?"

And for the third time I said "Yep. Won't be there when we first get on the boat, but it will arrive in time for us to go the show and dinner. Did you pack your bathing suit, sunscreen, etc. In your carry-on bag?"

"Of course, I plan to head to the pool as soon as we can."

Pat was notorious for her love of being in the sun. It was something I enjoyed also. My wife hated it and pipped in "You all enjoy the pool. I hope I can talk Jordie into exploring the ship some with me."

"Definitely, I want to see every inch of it. I still can't believe we are doing this." Jordie sounded like a young girl as she said that.

"I think you will be guiding, not exploring, I can't imagine there isn't a part of the ship you haven't seen before." This was our 12th Disney Cruise and would be our 4th time on the Dream, one of the four ships that Disney had.

My wife looked at me and said. "True, I guess."

My wife and I were Disney fanatics. We visited Disney World several times a year and went on Disney cruises as often as possible. There was something about being at Disney that just felt right with me. I loved everything there. The rides, the parades, the shows, the dinning, the special activities you could do, seeing Mickey and Donald, all of it. One of the things I didn't really tell my wife though is how much I loved the princesses, she sensed there was something about them that caught my attention, but she didn't know how much I loved seeing them. She even humored my desire to have my picture taken with them. I would always stand with plenty of space between us and offer my arm and elbow to them for the photo. I definitely didn't want them to think I was some dirty old perv trying for a quick feel.

What my wife didn't know was I was envious of them. I loved how beautiful they looked, their amazing make up, their perfect hair, although I knew from tours the hair was a wig. What I was really jealous of though was their gorgeous gowns. To be able to wear something that feminine and beautiful, they were so lucky. I loved to watch them move as almost gliding. Belle's big beautiful gold dress was probably my favorite, although both Cinderella's and Elsa's dresses were pretty amazing. I really shouldn't include Elsa in the princess category since she was technically a queen, but the dress was great.

My only other Disney complaints were, there was so much cute girl's Disney themed stuff. Starting with Minnie Ears, to pretty t shirts with cute sayings, all the way through Disney inspired nail designs. I hated that I couldn't enjoy Disney bounding like girls and women. The other complaint was with the Disney employees, or Cast Members as they were called, and it wasn't their fault, but every time one of them said "Princess" to any woman at Disney I would get green with envy inside. I longed for them to say to me "your ears are fabulous Princess!"

I am a deep in the closet crossdresser. I started dressing up after I turned 18 using my mom's things. First it was just bras, panties, and pantyhose. Eventually it would be a full outfit and even some make up. I was never caught by my mom but there were some close encounters. I also had one amazing afternoon at a female neighbor's house right after high school. She and her friend dressed me in tights, a blouse and a corduroy jumper style dress, and a pair of clogs. They added make up and I was in heaven. I didn't tell them I loved it and when the neighbor's father discovered us, he was not happy so nothing like that ever happened again.

As I got older, I went through the typical trials of most crossdresser and binged and purged women's clothing for years. I would even stop for many years at a time but then something would trigger the idea and desire and I would start up again. The arrival of the internet was both a blessing and curse. The blessing was in the information that was available, the realization that there were lots like me, and the ability to live vicariously through other crossdressers. The curse was that vicarious living wasn't enough a lot of times and the desire and need would grow stronger.

Currently, I have a collection of about a half dozen dresses, numerous pairs of heels (a weakness of mine), bras, panties, hose and tights. They are all hidden away in a place that my wife would never look and when the opportunity comes about, I pull them out and spend a few hours in feminine paradise. I also do a lot of daydreaming during that time of what it would be like to actually go outside the four walls of my house wearing women's clothes. I occasionally consider confessing my crossdressing to my wife but never do. I am truly scared that she won't keep my secret.

As we went up over the bridge coming into the port and everyone on the bus saw the Disney ship the noise and excitement grew. I always loved this part and seeing and hearing all the happy families.

Jordie lifted her body up so her head went over the seat and said "Thank you all again for doing this. It is just so wonderful. A dream coming true!"

"You are welcome, very happy we could do it." My wife replied. "It is going to be a lot of fun."

Pat and my wife had been best friends for years. Unfortunately, the last ten to fifteen years had been tough on Pat. She had gotten divorced and her husband had pretty well screwed her over with the settlement and she had always had to scratch her money together. Her daughter had basically followed the same path except she ended up with a husband walking out while the kids were still young. Her husband paid just enough alimony and child support, when he was actually working, to buy a little food, and clothes for the kids.

Jordie and her kids had moved back in with Pat and they all lived in a small three bedroom rambler. The basement of the house was used to make their income. Pat had a hair saloon and Jordie stored and sold her LuLaRoe clothes and Farmisa cosmetics from there. Those endeavors covered their mortgage, food and clothes and little else. Vacations for them were a thing of the past.

Meanwhile my wife and I were fortunate, I had a fantastic pension and had found a great retirement job to make even more money. My wife had recently inherited a sizeable amount of money when her mother passed away. This had allowed us to fuel our Disney addiction along with having other fun vacations. My wife would visit Pat and tell her all the stories and Pat would listen and be happy for her. Three months ago though Pat broke down when Sarah was telling the tales of our latest Disney adventure. She apologized but said she just couldn't hear it. It had been too long since she had been able to do anything like that and didn't think she would ever get to do something like that.

When Sarah got home, she told me the story and asked if we could do something for her. After talking it over we decided that we would invite her on a cruise with us. Part of our decision for this was we knew she loved Disney, the movies, the characters, the music. When we realized that if they shared a room, her daughter could also go for only a little more money we invited them both. We also decided that we would take them to Disney World but wanted to wait until Jordie's kids were about a year or two older. When we made the invitations, they both broke down and said they couldn't accept that, it was too much. We told them they would be giving us a gift as they allowed us to be a part of their excitement. When it turned out the trip was going to be on Jordie's 30th birthday that was the icing on the cake.

The bus came to a stop and more excitement built up with the passengers. I looked at the outfits that Sarah, Pat and Jordie were wearing. They all had on LuLaRou Disney leggings. When Jordie put her Minnie Ears on I may have outwardly sighed with envy. I just isn't fair I thought, and I stood up in my light blue Disney Castaway Cay t shirt and khaki shorts. I was even jealous of my wife's Doppleganger Hair Don't Care hat. We all had flip flops on but of course the girls had pretty painted toenails in different colors.

Everyone began to gather their things and patiently waited their turn to get off and start the check in process. We went through the security screening and headed up to check in and then moved onto the boat. Since my wife and had done these numerous times, weren't in awe but it was fantastic to see the looks of amazement and wonder in in Pat and Jordie's eyes. I had told them we would head to the buffet for lunch first and then would be free to start enjoying the trip. During lunch we talked about the show and dinner plans. Disney offers a Broadway quality show almost every night on this cruise, but the big show would be Beauty and the Beast on the third night. That was also Formal Night on the ship.

"So how dressy do we have to be for dinner tonight?" Pat asked.

My wife replied that she was wearing one of her Disney LuLaRou dresses tonight. I said I was wearing a Disney themed Tommy Bahama shirt and khakis. More khakis I thought, at least the shirts were Disney themed and colorful.

"What about the semi-form and formal night? What are you wearing then?" Jordie said.

"I brought some summer print dresses. It is sleeveless so I have a light sweater to go with it because it can sometimes be a little cool in the restaurants. I also have some new white strapped low wedged shoes." Sarah responded.

"But honestly, you don't have to dress up if you don't want to. You will see a wide variety those nights. There will be elegant gowns to leggings in the dinning room. Although I do like seeing the families where they get all dressed up for their pictures with Captain Mickey in his formal attire." I responded. I didn't add that I was also jealous of Minnie Mouse's formal night attire. It is a beautiful silver sequin dress and heels. I think most closeted crossdresser were automatically drawn to anything with sequins in it. I was also a big fan of anything with lace.

We were all finishing up our lunch and Pat and Jordie were anxious to get to their stateroom and check them out. We agreed that we would meet outside our rooms in 45 minutes. Pat and I were going to head to the pool and Sarah and Jordie were doing to do some exploring. As I started to stand, I somehow caught the side of table which caused both mine and my wife's drinks to spill over into my lap. It soaked my shorts and my t shirt. Great, I thought but at least I could change into my bathing suit when I go to the room.

Having stayed in the same class of room for all our cruises, there wasn't a lot to check out for us when we got to the room. I quickly changed out my clothes into my bathing suit and a t shirt that I had cut the sleeves off. That was my standard attire for the pool or the beach. I neatly folded up the clothes that were covered with the cokes that Sarah and I had been drinking and put them on the bathroom floor.

I pulled out the magnets to decorate the cabin room doors from my carry-on backpack. I had an Aerial magnet for Sarah and Donald Duck one for me. We also had a bunch of ship shaped magnets that listed all the different cruises we had been on. Last, I added our Platinum Castaway Club Magnet and Disney World Annual Pass magnets. I had picked out a Cinderella magnet for Pat and an Elsa magnet for Jordie and put them on their door. They had told me those were their favorite princesses. I bit my tongue and didn't point out that Elsa wasn't a princess.

I threw my Itouch, Kindle, and sunscreen in the Disney Cruise sling bag I had was ready to head to the pool. I told my wife I would see her at the safety briefing location and stepped in the hallway to wait for Pat. I choose to walk down the hall to look at some of the other door decorations before I heard Pat call my name.

"Hey Brad. Ready to head to the pool?"

"Definitely. I need a little energy boost from the sun." I replied.

"Thanks for the magnets. They are great."

We made our way to the adult pool area. Disney does a great job of letting you get away from kids and has adult only areas of the ship. The pool area was starting to get crowded but we were able to find a place in the sun and secured our loungers. I asked her if she wanted a drink and reminded her that Bahama Mamas were the drink of the day.

"That sounds fantastic." She said.

Just as I started to head towards the bar a waiter appeared and asked if we like anything. I told her we would each have a Bahama Mama. I sat down on my lounger and Pat removed her cover up. She was wearing a bright multi-color bathing suit that fit her well. A cute short skirt portion gave her some modesty around the waist and bottom, but her cleavage was displayed nicely.

"That is a cute bathing suit." I told her.

"Oh, you like it? I got it for the cruise. My bikini days are over I am afraid." She replied.

We took our seats and started to look around at the people who were in the pool area. There was a pretty good mixture of people. Older couples, possibly grandparents paying for the family vacation, and younger couples possibly on the ship alone. I enjoyed people watching and enjoyed checking out the hot bodies of both the women and men. A woman had come in who was wearing skin-tight mermaid leggings that showed off her ass. This caught my attention along with Pat's, and the woman sitting on the other side of me.

"Yea, if looked that good in them I would be wearing that also. Wow." I heard this from the woman next to me and when I looked at her, she had a kind of sheepish smile.

"I agree. Especially about the Wow. Everything there looks good." I said with a small laugh.

Pat leaned towards us and said. "I am pretty sure every eye in the place is looking at the same spot."

I looked around and found that was pretty much the truth. She had drawn a lot of attention. As I watched her a look of recognition came across her face and she started to wave her arm to someone on the other side. I followed her gaze and saw a man moving towards her. The closer he got the more obvious it was that they belonged together. He was shirtless and wearing a pair of tropical leave covered board shorts. They hung a little low on his waist and as he came up to her you could see his perfect abs including the veins that ran from his lower stomach into the shorts.

"Oh my" I heard from the woman on the other side.

Pat said to her "Eye candy for us too!"

I thought for a second and then said. "I think that couple is eye candy for everyone."

Pat raised an eyebrow "Are you saying you think he is eye candy? Or that the two of them together provide eye candy for everyone?"

"Yes." I said with a big grin.

"Yes, what? To both questions, OR the second one."

"Yes, to both. I can appreciate a hot body of both a man, or a woman." I replied but a little less sure of myself.

"Interesting. That is cool. Does Sarah know that you check men out?" Pat asked.

"Honestly, I don't know. And check out is a little strong. I am just saying that it is easy to admire a body that looks like that. Especially while on vacation."

"What happens on vacation stays on vacation." The other woman said and rolled over on her stomach and turned to look the other way as the eye candy couple moved to the other side of the ship.

Right then our waitress returned with out drinks. "Here you are princess." She said as she handed Pat her drink.

Even on the ship I thought, the girls and women get to be princesses. She handed me mine and the receipt with the bill. I handed her my Key to the World card to pay for the drinks.

We spent an hour sitting in the sun, watching people, Pat pointed out a few more hot guys and girls to me. We commented on some of the women's bathing suits, maybe being a little catty about some of the women's choices. It was very enjoyable.

"You know. I always feel comfortable with you. It is weird, normally I am a little nervous talking with men. With you it just feels, I don't know different. It is almost like you are one of the girls. I hope that doesn't offend you." Pat offered.

"No, not offended. I will take it as a compliment. Thank you. We probably need to get going. If we are late to the safety briefing, they won't be happy."

I noticed everyone else was getting up from their loungers and moving towards their pre-established spots. I stood up and went to reach down for my sling pack and heard the sound of stitches ripping. I then felt the back side of bathing suit become looser. I was pretty sure I knew what happened but turned my back to Pat and asked her if I had just ripped my bathing suit open.

"Oh yea, wide open. If it wasn't for the mesh, I would be getting a pretty good show." She laughed.

"Great." Well at least I had another suit with me but that was in my luggage that Disney was bringing on the ship. I wrapped my towel around to cover up the gaping hole and headed out.

We met Sarah and Jordie at the entrance to the movie theater which was our rendezvous spot for the briefing. Jordie was telling her mom all about the things she had seen on the ship and was very excited. I filled Sarah in on my latest wardrobe problem.

"Things aren't going really great for you, huh. I took your other clothes to the laundry and threw them in the washer for you. I didn't want the coke stain to set in. Once we are done here, we can throw them in dryer in case our luggage hasn't made it to the room."

Once the safety briefing was over, I headed straight back to the room. Sarah headed to the laundry to switch my laundry to the dryer. We all agreed to meet outside our rooms at 5:45 to head to the show. As I walked down the narrow hallway and approached our room, I saw that many of them had luggage sitting outside the doors. Disney would deliver you luggage to the door of your stateroom. As I got closer to our side by side rooms, I saw two suitcases outside Pat and Jordie's room. Our room only had one in front of it.

My wife and I had matching luggage, so I looked at the tag and it had her name on it. I was a little nervous that mine wasn't there but on a previous cruise with my brother in law, and sister in law one of their suitcases showed up a hour later than the other one, so I wasn't too worried.

I brought my wife's luggage in and decided I would take a quick shower. Sarah was in the room putting her stuff away when I got out of the shower. I poked my head out to see if my luggage was there and it wasn't.

"Umm.... So, when I went to laundry to put your clothes in the dryer they weren't there." She said.

"What? Where would they be? How can that happen?" I was starting to get frustrated. I had planned to put the shorts on and go get a beer to enjoy on the deck as we sailed off.

"I don't know sweetie, but they weren't. I am assuming someone threw them in with their stuff by mistake. I am sure they will just leave them in the laundry room when they realize it."