Happily Ever After Pt. 04

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A crossdresser at Disney World with his wife and friends.
11.5k words
4.56
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Part 4 of the 7 part series

Updated 06/10/2023
Created 03/15/2021
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Happily Ever After- A Princess at Disney World Part 4

Sorry for the delay between part 3 and part 4. If you don't know, there has been a problem with the rating system for Literotica stories. I was waiting to see if that would get worked out. I have been reader for a long time but only an author for about nine months. I didn't realize how much the ratings and comments meant to the authors until I became one. Thank you to everyone who takes a time to do them. Unfortunately, there is going to be a delay between part 4 and 5 also. I am going to WDW next week to do some more research so I my writing will be delayed.

I had woken up about six fifteen and tried to go back to sleep. It had been after midnight by the time we crawled into bed last night and I was hoping to sleep a little later. We had a great time and I had honestly loved wearing the Tinkerbell costume that Sarah, Pat and Jordie had surprised me with. They had been Wendy, Ms. Smee, and a sexy female Captain Hook.

Sarah and I had a few ups and downs again, although I think by the end of the evening, we were okay. I was beginning to think I was just going to have to accept that was going to happen and it was a part of her acceptance, or maybe it was how she tolerated my crossdressing, along with my interest in sex with men.

As I thought about the later part, I reached down and twirled my engagement ring on my finger. While I knew it wasn't real, it did make me smile, and I liked knowing that in two days I would have a chance to spend time alone with Steve. I also thought about how much I had enjoyed flirting with Matt, who I had just met. I don't think Sarah realized how much their attention, and attraction to me, made me feel like the female me was accepted.

I gave up on sleeping and slipped quietly into the bathroom to pee and for a quick shower. My legs were still smooth, so I did not shave them, but I closely shaved my face again after I got out. I dried off and did my make up.

I didn't want to run the blow drier, possibly waking Sarah up, so I did the best I could to dry my hair with a towel and put my hair into a pony tail. I could hear Sarah snoring and looked at the time on my phone. It was a little before seven o'clock, she wouldn't be waking up for about an hour.

I slipped on a pair of pink bikini panties and a pink bra. Stepping back into the dressing area I slid my forms into the bra and get a new panty liner for panties. I had laid out the khaki shorts I had worn yesterday morning and pulled them on. Then added my pink Disney Princesses t shirt with Girl's Just Want to Have Fun written on it. I grabbed my pink Magic Band, sunglasses and put on my flip flops, admiring my toe nail polish.

I slide out of the room, gently opening and closing the door. I wanted to get some coffee and I knew the machine in the room would have woken Sarah up. I headed to the restaurant I got a coffee and yogurt. I took them to the outside tables and sat to watch the resort come to life.

I scrolled through the Photopass pics on the my MyDisney Experience App. I loved seeing the smiles on Pat's and Jordie's face on the pics they were in. I also enjoyed seeing myself. It seemed like my smile was different as Brandi. Maybe it was the make up making my eyes more expressive but there was a difference.

"Hey Tinkerbell. Sorry, I couldn't resist. It is Brandi, right?" I looked up and Matt was standing next to the table I was at.

"Good Morning Matt. Yes, it is Brandi. Tinkerbell went back to Neverland." I smiled.

"Did she go back to Neverland without finding Peter?" He had a cocky grin and looked right at me.

"Oh, that was good. You are definitely better at this than me." I bated my eyes as I said it.

"Thanks, I think. What are you all doing today? Going to the parks?" He asked.

"Yes, going to Hollywood Studios a little later in the morning, the others are sleeping in. What about you all? Where are your kids?"

"They are still sleeping, or at least I think they are. My daughter wanted to do a sleep over in my sister's room last night with her cousins. And my son stayed in my brother and his wife's room with his cousin."

"So, you were all alone in your room last night? That must have been lonely." I winked at him.

"Okay, maybe you are better at this than you give yourself credit for." He replied. "Can I ask a personal question?"

"Sure, and I might answer it." I think the confidence in my voice had diminished.

"Fair enough. I see that ring on your finger, although you obviously enjoy flirting with me, which is okay flirting is just flirting. What puzzles me is I also see how, I think it is Sarah, and you interact or look at each other. What is going on there?" He had definitely lost confidence as he spoke.

I took a few seconds and then after a deep breath replied. "Not sure if this will shock you, anger you, disgust you, maybe all of those things, especially after the flirting. You seem like a decent guy, so I am going to tell you the truth."

"Pretty sure you aren't going to shock me, or any of the other things, if you say what I think you are going to say, the only bad thing will be having to admit to my little sister she was right and I will owe her a drink from our bet." He gave me a half grin.

I glanced up him still trying to find the courage to say it out loud and disappointed that I had to. I was going to miss the flirting even if it was just for today.

"Yea, that figures. A woman would definitely pick up on it sooner. So, to get right to the point Sarah is my wife and she isn't a lesbian, which is my cryptic way of telling you I am not what I appear to be. I hope you understand what I am saying because I don't want to actually say it. Although this week she is more of roommate and one of my girlfriends. We are still trying to figure all of this out."

"I understand. And I won't make you say it. If... if you explain the ring and the flirting."

"That is fair. So, the ring is a cubic zirconia engagement ring to be a Disney Princess. I was proposed to at the Magic Kingdom on Wednesday afternoon. Sarah set it up so I could experience being proposed to as a woman." I had gained a little confidence as I spoke.

"Wow, really? So, Sarah proposed to you, while you were dressed up?" He asked.

I chuckled. "Umm, no. I can't decide if it is because I am embarrassed telling you these things or if I am just assuming you would know things that you would have no way of knowing."

He laughed. "Don't be embarrassed. This is all fascinating to me and I promise you I won't judge."

"Thanks, so I have only been out to Sarah as crossdresser since early March. We were on a Disney cruise when it all came out. I also told her that I was interested in certain, let's say experiences with men while we were on the cruise." His eyes widened as I said that.

"We met a family on the cruise and became friendly with them. The husband of the woman and I became, uh, close." I had lowered my face as I said that.

"Really, like real close? And Sarah and his wife were okay with that?" His tone wasn't judgmental it was curious.

"Yes. Sarah told me she wanted me to have those experiences and honestly intimacy isn't really a part of our relationship these days. The wife and he had an arrangement before they met me. She allowed him to be with other people who were willing to do certain things, she didn't want to."

"Things?" He raised an eyebrow and smiled.

"I will let your imagination go wherever you want with that." I winked at him. "Anyways, they surprised us, or me actually, on Wednesday and showed up at Disney and Steve, that is his name, proposed to me in front of the castle by asking me to be his Disney Princess."

"Well, that explains the ring. What about the flirting with me?"

"Honestly, you are really the first man I have done that with besides some with Steve on the cruise. You are good at it, it is fun, and it makes me feel more feminine and like a woman. Plus, your kind of hot." I smiled at him.

"Kind of?" He laughed. "Well, you are fun to flirt with too, you definitely look like a woman, and you are hot. My sister hates that you have such a great ass and legs, she doesn't think it is fair."

I laughed. "Tell her it is some genetics, but it is also a ton of squats and hours on the stair machine. You never said what you all are doing today?"

"Animal Kingdom this morning. Then pool time and having dinner at Hollywood and Vine tonight followed by Fantasmic." He responded.

"I love Fantasmic. We are going to watch see it on Monday evening, our last night."

I looked at the time on my watch. I need to head up to the room and change into my tennis shoes plus make sure Sarah was awake. I stood up and put my hand on Matt's forearm, surprised that caused a little charge to run through me from just that small amount of intimate contact.

"Thanks for a great start to the day you are so easy to talk to. Maybe I will see you at the pool later this afternoon? I would love to flirt with you some more." I smiled and headed back to my room.

"I really hope so. Have a great time this morning Brandi." I looked back over my shoulder and saw him watching me walk away.

Sarah was up and finishing dressing when I entered the room.

"Hey, what have you been doing this morning? What time did you get up? You look like you are ready for the day except for your shoes." She asked as she walked towards the dressing area.

I hesitated to answer, worried what her reaction would be. "I got up a little after six, just woke up wide awake so I showered and got ready. Then I went to get some coffee and ran into Matt, so I was chatting with him."

She quickly turned her head around when she heard me say Matt. "Really? What did you all talk about? And you just happened to run into him?"

"I was sitting at one of the outside tables and he walked up. Umm. He actually asked about you and me. He, and his sister, I guess had picked up on.... things..."

"Really, and what did you tell him?" She had moved closer to me.

"Pretty much everything. He was very easy to talk to." I was finishing putting my tennis shoes on.

She sat on the bed next to me. "And he was okay with you or you know... that you are actually not a woman?"

"Yes. Even told me he hoped to see me later so we could flirt some more." I wasn't sure why I was so proud when I said that.

"Wow. Just be careful with that. What do you think Steve would say if he knew? Don't mess anything up for Sunday, a lot of work has gone into that." She had put her hand on my thigh and looked directly at me as she said it.

"Well, I don't plan to tell Steve. And it isn't like this is real." I held up my hand to show my engagement ring. "Plus, it is just flirting."

"Okay, but I bet given the chance you would be happy to do more than just flirt, right?"

"Uh, probably." I said now looking down.

"I knew it. Slut!" She laughed and stood up. "Honestly, glad you are getting this experience."

I quickly touched up my makeup, grabbed my Rose Gold Ears and back pack, put my pink Magic Band on and I was ready. I noticed Sarah was wearing shorts today. They were longer than mine, but they fit her butt well.

I was behind her as she pulled up the door. "Hey, you look good. I like those shorts."

She laughed. "You like my butt in these shorts. I know you. Speaking of butts, wow Jordie. You know Disney is a family place."

I hadn't seen Jordie when Sarah first opened the door, but she was leaning against the railing with her back and butt to us. Sarah was right, she had on a pair of short, tight, white shorts that hugged her curves. When she turned around you could see her makeup had been done to match her lavender v neck shirt. She looked fantastic.

"Wow, girlfriend, you look amazing." I said.

"Thanks. You look good also, pink is a good color for you." She smiled.

We headed to breakfast, all of us choosing share beignets and avoiding covering ourselves with powdered sugar. Sarah and I told Pam and Jordie to make sure that they would be hungry for dinner tonight. We quickly ate and took our coffee and coke with us to catch the bus.

We lucked out and the bus was pulling up right as we got to the bus stop. Hollywood Studios was a quick bus ride and because we were going after the rush to be there at rope drop, it wasn't crowded. Bag check and security were painless and soon were headed to Tower of Terror, our first Fastpass.

Hollywood Studios is smaller than all the other parks which makes it easy to get around. We quickly arrived at the ride. The theming for the Tower of Terror is fantastic. We heard a family behind us talking about how scared they were. When they asked if we had ridden it before and if it was really scary, we told them no. We did tell them that the anticipation was very scary and that is what made the ride fun.

The ride ended and we headed out through the gift store. We saw the family that had asked about the ride while we were in line, they told us we were right about the anticipation being the worst part and they loved it. I told them they had to ride it again because the drop sequences changed and that we had only had a fair one. They thanked us and headed out.

We walked out and made the short walk to RocknRoll Roller Coaster. This was Sarah's favorite ride. The standby line said it was a forty-five-minute wait, but we could see that the single rider line was inside the door. We explained to Pat and Jordie that it would probably be twenty minutes or less.

We entered the line and got held up just inside the door for five minutes before we were moved through to the pre-show area and eventually the single rider queue line inside.

"So why is this your favorite?" Jordie asked.

"I don't know. I just like it. It is fast, the music is fun. The only bad thing is it is over way too fast. It only lasts about 47 seconds." Sarah replied.

"Oh, sounds like my ex-husband." Pat laughed.

"Mom! TMI, that is my dad you are talking about." Jordie said but she was smiling.

Our line moved fairly quickly. "Same bet as Everest?"

"Sure." Jordie said quickly.

"I am in." Pat added.

"What is the bet?" Sarah asked.

"Whoever gets the hottest ride partner has to buy drinks at the pool this afternoon." I said.

"Okay, and for an added side bet. If you win AND your song is "Dude, Looks Like a Lady" you have to buy two rounds." Sarah grabbed my arm as she started to laugh.

"What is the song part?" Pat asked.

"Each ride vehicle plays different Aerosmith songs while you ride, it definitely adds to the fun." Sarah told her.

"Okay. I will take that bet."

We moved up and Pat went first. Her partner was a young teen girl. Jordie was next and she ended up with the mom of two tweens who were the seats in front of her. I was next and got a balding, beer bellied husband and dad, whose wife and kid were in front of us. Sarah was last and she was partnered with the grandfather of a family group. He was probably early sixties and looked good for his age. His face showed he was pleased with his ride mate.

My ride partner almost fell over climbing into his seat and struggled to get seated. I was surprised the effect my breast forms had on getting the restraint to sit comfortably down over my shoulders. I laughed when the ride started, and we shot down the track into the loops and realized that the song was "Dude Looks Like a Lady." I looked over at my ride partner and was a little worried he was going to wet his pants. His daughter's screams from the car in front of almost drowned out the music.

At the end of the ride, we all met in the gift shop and walked out, stopping at the little girls room just outside of it for a quick pee break.

"Okay, I think I am with Sarah, that has been my favorite ride so far." Jordie said. "I also think Sarah owes us drinks."

Pat laughed. "Well, I know that you and I aren't the ones buying."

"So, you all are saying you didn't think Brandi's partner wasn't hot?" Sarah laughed. "He definitely thought she was hot. He almost fell over getting in the ride because his eyes were glued to her ass while she was getting in."

"Is that what happened?" I asked.

"Yes. The best part is I think his wife saw it also. Oh, did you get the song?" Sarah was smiling.

"Yes. Guess he didn't know he was living it." I chuckled.

We were headed to Toy Story Land and had some time to kill before our Fastpass for the Slink Dog Roller Coaster, so we decided to catch the Little Mermaid show. I knew Sarah would like that and it would give us a chance to sit in the air conditioning for a little while. The show was becoming a little dated but still cute.

We left the show and tapped our Magic Bands for our Fastpasses for Slink Dog five minutes before their start time, which was acceptable, so we got the green circle that allowed us to enter. The ride is a family roller coaster so not as fast as RocknRoll or Everest, but it is a fun ride.

We were off it at just after twelve o'clock and headed over the Baseline Tap House. We each got a beer flight and ordered two pretzels. This was a must stop for me when I was here as Brad and Brandi had decided that girls can enjoy a beer also.

"So, Brandi spent the morning with Matt." Sarah announced.

"Define, spent. You didn't have a protein shake to start the day, did you?" Pat laughed.

"No, I had coffee, seated at one of the tables, and he stopped at chatted with me." I gave Sarah a harsh look.

"What, just making conversation." Sarah winked at me.

"Was he flirty McGee with you this morning?" Jordie asked.

I blushed. "A little. He knows about me and we talked about that and did flirt some, even after he knew the real deal."

"Oh. Very cool. How is it though, once again, you are in the lead in the most likely to get some dick competition?" Jordie said while winking.

I was surprised to hear that come from Jordie, but I laughed.

"In the lead... she already won. She got some the second day, remember." Sarah said.

"Oh, yea, that's right. Slut." Jordie winked at me this time.

"Jordie, even you? That is the second time today I have been called a slut" I smiled at her.

"Well, if the come fuck me heels fit." Pat laughed.

We finished our flights and pretzels, then walked the short distance to Star Tours, our last Fastpass. In comparison to Flight of Passage at Animal Kingdom, or Soarin at Epcot, the motion simulator technology is a little outdated but Pat and Jordie enjoyed it. It was the first time Sarah and I had ridden it a few years.

On our way to the front of the park we decided to check out the single rider line for RocknRoll Roller Coaster. The line for single riders was just outside the entrance door so we decided to ride it one more time. None of us got a ride partner worth noting and we were at the bus stop for the ride back to the resort right after three o'clock.

On the bus ride back Jordie asked. "What are you wearing tonight? I know it isn't super dressy."

I quickly looked over at Pat and Sarah. They weren't paying attention. "Um. You are right but I am wearing a new dress tonight that is a surprise. Sarah hasn't seen it yet. When I unpacked and hung it up, I hide it behind a couple sundresses."

"Oh, is it really dressy? I brought a new body con dress but thought it might be a little much?"

"I don't think so, but I am sure Sarah will think it is. She always thinks I am overdressing. If you wear your new dress I won't stand out as much." I smiled.

"Okay, what about shoes? I have some heeled wedges."

"Those would be fine. I have a pair of peeped toed sling backs with a three-inch heel I am going to wear. Sarah isn't going to be happy. I am glad you will have heeled shoes on, I won't stand out as a giant when we are walking." I gave her a big grin.