Finally a Princess Pt. 06

Story Info
A Disney loving crossdressers dream trip comes to an end.
4.8k words
4.71
7.3k
8

Part 6 of the 6 part series

Updated 06/10/2023
Created 08/01/2020
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

Finally a Princess (Part 6)

Part 6 of a Disney loving crossdresser who has come out to his wife on a Disney Cruise. Living the dream is coming to an end and the future is uncertain.

Again, I woke up to feel of the ship vibrating. I knew this meant we were back at Port Canaveral and would be docked soon. I sensed Steve was still in the bed but we were no longer spooned together like when I had drifted off to sleep. I gently moved and looked to my left and saw he was laying on his back and seemed to be sleeping sounding still.

I took a moment to reflect on my week. Six days ago I had boarded the Disney Dream cruise ship with my wife, our friend Pat and her adult daughter Jordie. At the time I did not know that my wife had discovered I was crossdresser months ago and that she, Pat and Jordie, had hatched a plan to get me out of the closet while on the cruise.

Since that first evening I had so many of my dreams and fantasies come true. I had lived as a woman for the past five days. I got to wear beautiful dresses, amazing heels, and with the incredible help of Pat and Jordie, I had looked pretty good while doing it. Sarah, my wife, had been mostly supportive and encouraging during all of this. Occasionally, she would make a comment or dig that conflicted with that and that made me wonder what the future would be for Brandi, the name I had chosen when was in girl mode.

I had also meet Lisa, the wife of the man who I had woken up next too. She and I had quickly become friends and she shared that she occasionally liked to have sex with women and there were certain sexual activities with men she didn't like doing. A deal was reached with her husband, Steve, that she could seek out women on occasion and in return he was free to get blow jobs and have anal sex, things she didn't want to do, with others if he wanted.

Luckily for me, he decided he wanted those things with me. He had been drawn in by the sight of my ass in leggings on the first night of the cruise. For a man I definitely had a great butt. Partly, because I spend hours on the stair machine and doing squats partly, because I was just lucky. The stair machine also made sure I had fantastic legs, especially when I was wearing heels.

The past couple of days Steve and I had hooked up for sex on a number of occasions. Last night, while we were out dancing with our groups- Lisa and Sarah, had told Steve and I, that Lisa was going to have a sleepover in mine and Sarah's room. This meant that Steve would be free to bring me back to his room and that is how I ended up in bed with him.

I quietly slipped out of bed and went into the bath room. I looked in the mirror and was happy to see, that for the most part, my makeup had survived through the night. I sat to pee, checked the panty liner I put in my thong last night and saw that it had done what I wanted, caught Steve's cum that had leaked out of me during the night.

I removed it, cleaned up a little more down there, and put tooth paste on a finger and brushed my teeth the best I could. I borrowed one of Lisa's combs and did the best I could with my hair to bring it kind of back to life. When Steve woke up I wanted to look at least a little bit like I had looked last night.

I moved out of the bath room and back to the bed. There was just enough light coming in that I could see that Steve was still asleep. I looked at the clock, just past 6:30, I knew that I needed to be getting back to my room soon. I also knew that I wanted to feel Steve's body close to me one more time. I suddenly had an idea.

I slipped back into bed and slowly moved the blanket and sheet down his body until his dick was exposed. He stirred a little but didn't wake up. I moved closer to him and looked down at the beautiful object that had given me so much pleasure the last couple days. I gently laid my head just above his waist and brought his cock into my mouth.

It was soft and because I washed him after our sex last night, it didn't have the wonderful, intoxicating, manly, musty smell that I loved. Still, it felt great on my tongue and it was coming to life. As it grew it got a little more aggressive with my tongue and soon he was completely hard.

"Good Morning, Brandi."

Steve had woken up I repositioned so that I could look at him while my tongue ran over his dick. I stopped for a second to smile at him.

"Good Morning."

I went back to work on his cock, bringing my hand to the base while my mouth worked hard on the upper portion of his shaft. I could hear him moan and his breathing picking up so I knew that I was having the desired effect. When his hands started to run through my hair I was sure I would be able to get him off soon.

"Jesus, you are great cocksucker."

That just made me increase my efforts, I was sucking and swirling my tongue on the head of his dick, while my hand was jerking faster.

"What an amazing way to way up. Wholly fuck, suck my dick, don't stop that."

I quickly took my hand and caressed his balls which were drawing up close to him. I also felt his dick stiffen more. I move it back to the base and grasped it a little tighter and continued to jerk.

"Cumming soon my cock sucking slut." He groaned loudly.

I am not sure why but when he called me a slut it turned me on, it even felt a little like a compliment. He had done it two nights ago when he was fucking me from behind also. I made another decision, the other times I had sucked him off I had him shoot in my mouth, I decided to give him a little visual treat and maybe an image to remember of me.

"Fuck, I am cumming!"

I pulled my mouth off him and felt the first shot of cum hit my forehead, followed by a less powerful one landing on my nose. As I continued to milk the cum out of him, I used his dick to paint the rest of my face, mostly my cheek and lips. When was satisfied I had gotten all I could out him, I released his dick and turned to look directly at him with a big smile.

"That was hot as fuck. Jesus."

Never taking my eyes of his I started to use my finger to scoop the cum off my face and stuff it in my mouth. Once I felt I had cleaned it all up, I went back to his dick and used my tongue and mouth to get the little that had leaked out.

I climbed up the bed and leaned down and gave him a quick kiss.

"Slut huh?"

He got a slight panicked look on his face and started to say something. I put my fingers on this lips.

"Relax Sweetie, it turns me on when you say it."

He pulled me close to him and we laid together for a few minutes.

"Steve, I can't thank you enough for this week. I have memories I will never forget. My first dance as a woman, my first date as a woman, my first blow job, losing my anal virginity. It is going to be hard to move past this."

He kissed me again. Tenderly. There really wasn't anything to say to that. We both knew that he wasn't leaving his wife. I had no intention of leaving mine either, but I also knew that Sarah and I had a lot to figure out after this week. His life would go back to the way it was before this week had started and mine would have to find a new normal.

"I rose up. I have to get going, plus I am sure that Lisa will be here any minute, as awesome as she has been, I don't think I want to be in bed with you when she comes in."

He smiled. "Yea, I think it will be an interesting enough morning without adding that."

I jumped up and ran into the bathroom again to see what the cum facial had done to my makeup. I cleaned up a little and came back out. Steve was out of bed and putting a pair of briefs on. I went over the couch and slipped my shapeware panties over my thong. I then stepped into my dress, turned my back to Steve who zipped me up, and grabbed my heels and clutch.

He walked with me to the door and we kissed one last time and said quiet good byes. I slipped out the door and made me way down the hallway carrying my shoes in my hand. A woman with a coffee in her hand walked past and said good morning with a shit eating grin on her face. I knew how this looked.

I was heading to the stair to go down the one floor to the level my stateroom was on. Just as I was getting there Lisa came out of the elevator. We stopped and looked at each other. I wasn't sure what to say.

Finally, she spoke. "Doing the walk of shame this morning huh." She laughed after that, it was loud and seemed genuine.

"Yes, I guess another first for me this week."

"Did you have a good evening?" The question seemed sincere.

"Yes, thank you. Thank you for all your support, acceptance, encouragement, all of it this week. I will never forget."

"I know you won't."

"I was serious when I said I wanted Brandi and Lisa to be friends going forward. I hope we can find a way to do that." My eyes were looking down as I said it. I was scared of what I would see in her face.

"I do to. Give me a couple days to reset things with Steve and I think we will be fine. Come give me hug Girlfriend!"

I moved to her and even with my heels and clutch in my hand I was able to squeeze her tight.

"Safe travels today Brandi. Oh, and take it easy on Sarah today. She is still processing all of this."

"You too. And I will."

I made my way to the stairs and at the landing while heading down, I passed a couple in their thirties on their way up . The woman grinned at me, the man smirked. As they moved out of my vision I heard him say to her, I bet she got rallied last night. The funny thing was I just happy he said she. I finished my walk of shame, passing a few others who gave knowing smiles, and arrived at the door to our room.

I entered and heard Sarah moving around in the bathroom. I wanted to quickly get out of my dress and take a fast shower before we had to be at breakfast at 08:00. It dawned on my suddenly that I would need some help to do that because reaching my zipper would be tough. I surrendered that I would have to ask Sarah for help.

I tapped on the bathroom door. "Um, when you have a minute can you come help me?" My voice was very low and full of uncertainty.

She stepped out and said a very perfunctory. "Good Morning."

"Good Morning." I turned my back to her. "Can you unzip me, please?"

She reached up and slid the zipper down and stepped back in the toilet side bathroom but left the door open. I had rapidly moved over to the couch and took the dress and all my undergarments off, except the thong. It had been awhile since Sarah and I had seen each other naked and this didn't seem like the morning for that to suddenly happen again.

I made my way towards the shower bathroom and reached for the door just as she stepped out.

"I left my razor and shaving cream in there and left my deodorant in the other bath room. Are you planning on any makeup this morning, because if you are you, need to let Jordie know before she packs everything up."

"Thanks for leaving the stuff out. And no. Can you please text her so she knows she can finish packing?"

I closed the door behind me and stepped in the shower. It felt really good but I knew I couldn't stay in there long. I made sure I was as clean as I could be, shaved closely and got out. I wrapped the towel around me up under my arms and jumped into the other bathroom. I quickly finished in there and stepped back into the room to get dressed.

Sarah saw me and, I am assuming it was how I was wearing the towel, I heard. "You are going to take this girl thing all the way the end aren't you."

"What do you mean?"

"Look at how you are wearing your towel. Look at the clothes you are getting ready to put on. I will admit I am a little shocked that you decided on no makeup this morning."

"You are the one that suggested I wear this home yesterday. Do you remember?"

"Yes, I remember. I am remembering all my suggestions this week. The bigger question is how many of them am I regretting?"

"Are you regretting them?"

"Honestly, I don't know."

I pulled the thong panties I had picked out on under my towel. I then sat and put the leggings on that I worn the second day of the cruise. They were purple and pink and had Minnie silhouettes on them. Next came the sea foam Disney Cruise spirit jersey. I knew that when I pulled the hat out of my backpack it wasn't going to help my case but part of me didn't care. I put the pink Castaway Cay hat on my head. Looking in the mirror I liked what I saw but I did miss having boobs.

Sarah just stared at me. I knew she wanted to say something but for whatever reason was biting her tongue.

"I need to take this over to Pat and Jordie's room. I held up my dress and heels. Jordie told me she had room in her carry on for them. I also didn't think about what do with my forms. I don't think I can take them thru TSA as carry on."

"Fine. We need to leave soon. Breakfast is at eight o'clock and then we need to head to the bus for the airport. And you can take them through, I checked that before the trip."

"Really? Wow, okay thanks."

I placed them in my back pack, grabbed the dress and heels and went next door.

Pat answered when I tapped on their door.

"Good Morning. How are you all?"

"Ugh, we are rough. Might have partied a little hard last night after you left."

"Might have?" I smiled at her. "Jordie said she could pack these for me."

"Sure. Just lay them on the bed and she will pack them when she gets out of the bathroom. SO... how was your night?" And even feeling rough she followed with her beautiful laugh.

"It was pretty amazing honestly. Unfortunately, my morning has been a little rough." I motioned towards our room with my thumb.

"Yea, she got pretty quiet after you left last night. I think she is worried about where this is headed."

"I know. And I would be lying if I said I don't have some questions myself. I definitely don't want to go back into hiding but I am pretty sure I don't want this full time either. Or at least I don't want the sacrifices that would mean."

"Maybe you should be telling her that instead of me. Just a thought."

"Thanks. And thanks for everything." I grabbed her and pulled her close for a hug. "See you in few minutes so we can go get breakfast."

I went back to our room and saw Sarah sitting on the couch bed. I walked over to her and sat next to her. She turned towards me with a strange look on her face. I reached out and took her hand in mine.

"Thank you for an amazing week. A longer talk will have to happen later but, I have no intention of being Brandi all the time. I would have to give up way to much for that and the biggest thing I would have to give up would be the life we have built the past thirty years."

She was looking right into my eyes as I said that, I could see them getting wet. I pulled her in for a hug and we held each other for minute. As we pulled away she looked into my eyes and suddenly leaned forward and kissed me on the lips. It wasn't a passionate kiss, it wasn't even really romantic, but it was intimate.

"I really needed to hear that. Thank you."

"I should have made that clear earlier. I have been a little self-obsessed. I am sorry."

"Well you did tell me that crossdressers are basically teenage girls, and teenage girls are definitely self-obsessed, so you basically did tell me." She smiled and then we both laughed.

We heard a knock at the door and knew that Pat and Jordie were ready. I stood up to get my back pack and suddenly noticed that the couch bed was completely still made. No one had slept in it last night. I started to ask Sarah about that but she was answering the door already.

"Ready for breakfast?" Sarah said that loudly and with a touch of sarcasm. I think she was making fun or what appeared to be serious hangovers for both Pat and Jordie.

They both grunted a yes and we headed out of the room and off to the Royal Palace for a sit down breakfast. Disney wanted us off the boat so they could flip if for the cruise that would start this afternoon. The morning you got off the boat you got a sit down, limited menu breakfast, in an effort to move you off.

Walking down the hallway was a little depressing. All the door decorations were gone. Many stateroom doors were open and you could see the cast members busily cleaning and resetting the rooms. We made it to the elevator and to wait for a second one before we could enter. When we climbed in Nancy and Melissa were in it.

"Good morning Girls." I said.

"Good morning." They looked a little worse for the wear this morning also.

Jordie shared a look with them and I was starting to understand that there was a tie in with the hangovers and maybe something else?. I began to wonder if maybe Jordie had taken them up of their offer to provide her a birthday orgasm.

We got off the elevator and went to the restaurant. The waitstaff he told us last night to just come back to the table we had sat at the night before. We found a place to stash our carry on stuff and sat down.

"Good Morning Princesses." Our waitress said. "Would anyone like some coffee?"

Pat, Jordie and I said yes while she passed out menus. We took a minute to look at them and quickly decided on what we wanted to eat. I was actually a little hungry this morning and when I announced what I was planning on order, Sarah raised an eyebrow.

"Work up an appetite from getting fucked last night?" She was smiling from ear to ear as she said it and reached out and squeezed my knee.

I sensed this was a bit of an olive branch and a chance to use humor to help move us back to a comfortable place. So I responded.

"Definitely, and the protein shake I had early this morning didn't satisfy it."

Sarah laughed loudly at that joined by chuckles from Pat and Jordie.

"You are seriously, a cum slut. Do you really like the taste of it?" And she squeezed my knee again, not wait for my answering, before continuing. "Jordie, did you work up an appetite last?"

Oh, wow. I was right. Maybe something had happened with Jordie, Nancy and Melissa. I was waiting to hear her answer.

"No, I chickened out. We got to their room and there was some making out but I just couldn't go forward with it. Plus, I think, Nancy and Melissa were more into the idea of a threesome than actually going through with it. Those two are seriously in love with each other. They are lucky. So I slept on the couch."

"And Pat? How about you?" Sarah asked with a sly grin.

Pat? Wow, I must have missed a lot after I left with Steve last night. Who did she possibly hook up with? Her cheeks were as red as I ever seen.

"Yea, mom. What happened after you and Lisa left the bar?"

Lisa? Lisa and Pat? Why hadn't Lisa said something to me when I saw her this morning? We were all looking at her waiting for her to say something. It was also the first time I had really seen Jordie smile this morning.

Finally, Pat cheeks were still red but she smiled. "It was the best orgasm of my life. Or orgasms I should say."

"What? Wow.... Really? Details!" I don't know why I was shocked but I was.

"Not a lot of details to share. It happened so fast. We got to my room, suddenly I was naked and her mouth was on my tits. She kissed me but I didn't really kiss her back, she seemed to take the hint, moved back to my tits. Then her fingers were on my pussy and in my pussy, followed by her mouth and tongue and Wow. I may have even squirted a little. I have never done that!"

We all stared at her. Surprised and fascinated.

"We feel asleep and when we woke up this morning it was pretty awkward, honestly. I gave her a quick hug and a thank you. Fortunately, she understood, laughed a little, thanked me and said good bye."

I smiled at her. "Would you do it again?"

Pat looked like she was thinking. "Would I hook up with a woman again? Probably not. Would I go back and knowing what would happen, still go back to the room with Lisa? For sure. That orgasm was incredible." And we heard that wonderful Pat laugh.

12