Finally a Princess Pt. 04

Finally a Princess (Part 4)

Part 4 of a Disney loving crossdresser who has come out to his wife on a Disney Cruise. With a lot of help, and some Pixie Dust, dreams do come true.

For the third morning in a row I woke up and saw just a little light streaming into our stateroom. My wife Sarah was sleeping on the bed and I could hear her lightly snoring. One of the reasons we rarely slept in the same bed. I was on the couch that converted into a bed.

As I had the past two mornings, I spent a few minutes reflecting on the day before and everything that happened. I had spent another day as woman. This included time on Disney's Castaway Cay in a woman's bathing suit, and the night wearing a favorite lace dress and heels. My wife was supporting this and I was getting plenty of help from our friend Pat and her adult daughter Jordie, who were on the cruise with us.

I also woke up feeling very nervous. I had a date this morning, with a man, and a man that I was finding myself more attracted to when I spent time with him. Last night we had danced together and he had pulled me close to him and I felt like I was on fire. For some reason, at least so far, Sarah was supporting this also.

I got up and headed to the bathroom to pee. Looking in the mirror I knew that I would have to shave. I also decided that I needed to shave my legs and underarms again so I hopped in the shower and again loved the feeling of running a razor over my legs. Sarah had told me that if I had to do this all the time I wouldn't enjoy it as much, but right now every feminine thing I did gave me a feeling of joy.

I quietly left the shower and moved across the room, being careful not to wake Sarah. I grabbed a pair of my purple lace edged bikini panties, now that I had my full collection of panties available, I could save the thongs for when the outfit called for them, or I needed them to keep things tightly controlled. I also put on the bra that matched and slipped my breast forms in the cups. I pulled on a borrowed pair of shorts and my new Castaway Cay woman's pale lavender shirt. My new pink hat completed my outfit and I headed out the door.

It felt good to know I was wearing mostly my own stuff, especially my own, panties and bra. Sarah, with the help of Pat and Jordie, had packed a lot of my girls stuff that had been hidden at our home. After discovering I was crossdresser, by coming across open web pages on my Ipad, she had found my stash of stuff. With Pat's help she had set up a scenario where I had been forced to borrow women's clothes for two days because my luggage was lost. After I confessed I was a crossdresser, she confessed to knowing and the plan that she and Pat had hatched.

I made my way up to the top deck and grabbed a cup of coffee before heading to the bow to watch us approach the Port of Nassau. Again there was a large number of people along the rail doing the same thing I was. The sun was now brightly shining and, as I felt it on my skin, it was giving me energy along with the coffee I sipped.

"Good Morning Girl Friend." The loud voice behind me belonged to Susan, the wife of the man I had a date with later this morning.

"Good Morning Susan." I had moved closer to her to greet her because I knew the one thing that definitely gave me away, was my voice. "How are you this morning?"

"I am great. It is beautiful out. The bigger question is how are you this morning? Big night last night, how are your feet and calves doing? All that dancing in your heels must have made them sore." She grinned and winked at me. The wink, I think, was because of the slow dance I had done with her husband Steve.

"Actually, they are fine. If they were sore it would have been worth it though. Last night was honestly like a dream."

"I am happy for you. It is wonderful that you are getting to experience all this. You should know that I had to hold Steve off last night. I think that dance with you had him ready to burst. Are you looking forward to your date?"

"I am. I have to ask again, are you sure you are okay with this? I also have to be honest with you. If I get the chance to be intimate with Steve I am pretty positive I am going to take it."

"Intimate. That is sweet. You mean if you get a chance to suck him off or get plowed by his dick don't you?" She must have seen my eyes grow wide. "Relax, I am half teasing. I learned a long time that when it comes to talking about sex, it is better to be frank about it. When we use euphemisms or hints we tend to cause confusion or not get what we want."

"Okay, yes that is what I meant. Especially the sucking him off part. I have really wanted to the experience doing that and this seems like the prefect opportunity."

"Again, yuck but more power to you girls who enjoy that. So you aren't as positive about the being fucked in the ass part? Because I can assure you Steve wants your ass."

"I am more scared of that honestly. Umm... I am not a total virgin there. I have had dildos and vibrators in my butt before, what I am scared of is not being in control of it."

Susan smiled. "Understandable, I have tried it. I hated it. It is why I let, and even encourage, Steve to find others for that, I have heard that having a prostrate can make it feel a lot better. My advice to you is lots of lube."

We both laughed as she said that. We were entering the small opening of the port now, something that amazed me that could be done with these huge cruise ships.

"I struck out with your wife last night. I also understand that Nancy and Melissa struck out with Jordie. I guess we will have to look outside the group for a little fun."

"What about Pat? I told you, if I was going to pick one of the three of them who would be willing to let you lick their pussy, it would be her. No, idea if she would return that favor but, I bet, given the right circumstances she would let you go down on her."

"Okay, maybe I will cozy up to her while we shop today. I am off to shower and get dressed. I enjoy our morning chats."

"I enjoy them also. I am already looking forward to seeing you here tomorrow morning." That was a true statement.

I decided to head back because I wanted have as much time to get ready as possible. I realized that I still needed to pick out something to wear today. None of the women's clothes I owned before this trip would be appropriate for a visit to the museum or Margaritaville. I guess I could wear what I had on but I was hoping for something that was more girly than this.

Sarah was just waking up when I got back to the room. She is definitely not a morning person so I always tried to be careful about being to cheery first thing. I made my way to the other side of the room and sat down so she could keep waking on her schedule.

"Hey, good morning. How did you sleep? Did you watch us pull into port? See anything interesting? Have you showered yet?"

I guess she decided she was awake. "Good morning, I slept well actually. I did watch us pull in, still amazing to watch that. I have showered and the only interesting thing I saw was Lisa."

"How was Lisa this morning?"

"She was fine. She was disappointed she struck out with you." I laughed a little as I said that.

"Did she actually tell you that? She literally has no filter does she."

"She did actually tell me that."

"Did she say anything about Steve? Is your date still on?"

"She told me he is raring to go. And the date is still on as far as I know."

There was a bit of an awkward silence for a minute before Sarah responded. "And how about you? Are you still excited about it?"

"Truthfully?"

"Yes, I have told you I want the truth with all of this."

"Yes, I feel like I am in high school. I can't wait to spend time with him."

"Well okay GIRL, let's get you ready then."

I saw her typing on her phone and I assumed she was sending a message to Pat. I am not sure why but I suddenly realized how strange this was. My wife was working on getting me ready, to make sure that I looked girly and attractive for a date with a married man, whose wife was encouraging this. I heard her phone vibrate and she smiled when she read the message.

"Pat and Jordie are all set to get you ready. We had picked out an outfit for you that I thought you would like for our at sea day but I wasn't ready to spill the beans that day. Besides, the weather that morning wasn't really that great and this is more of a sunny day outfit. The best part is it will be perfect for today."

We got up and headed to Pat and Jordie's room. After exchanging good mornings and lots of smiles Pat told me that she was just going to fluff my hair some, then Jordie would do my makeup. Sarah again told me I need to watch what she was doing so I could start doing it on my own. Once again I was amazed at her work. She seemed to go light on the eye shadow but heavier on the eye liner and mascara. The result is my green eyes really seemed to stand out. She had also done my lipstick in a deep red color.

"We need her nails to match the lipstick, plus honestly red nails look really hot on a hand wrapped around a penis." As Pat said that both Sarah and I burst out laughing. "What, they do. Plus they will match her outfit." Pat grabbed my hand and started her work.

"Ready to see the outfit?" Sarah asked when she had finished.

I just nodded and Pat went over to the wardrobe and pulled out two hangers. On one of them was a red with white polka dots skirt. The other had a black short sleeved shirt on it. This was definitely an Minnie inspired outfit. I was smiling but it looked like the skirt was pretty short and the shirt was small.

"Oh wait, what color are your undies?" Jordie asked that.

"Umm, purple, why does that matter?"

All three girls laughed and Pat said. "Because I am pretty sure this outfit is meant to be worn with either black or red undergarments. AND... if a girl thinks she is going to have sex she wants to make sure she has the right underwear on."

I was beat red but Sarah had moved to the door and left the room. She was back shortly with a red bra and red bikini pants. I took them from her and started to move to the bathroom to change. Sarah told me to just change into the bra and panties and to step back out. I started to protest but remembered Pat's comments about if we were all going to be girls on this trip we needed to be comfortable in towels, nighties and undies in front of each other.

When I came out I was nervous but Jordie broke the ice. "If I was Steve, or I liked girls, I would jump all over that." Her smile lit up the room.

Sarah handed me the shirt first. I pulled it on and realized it was tight across the chest and maybe was a little short. I moved to the mirror and noticed if you looked really close you could see the out line of my bra straps and a little bit of the contour of lace on the cups of the bra.

"Yea, we had a different bra in mind with this outfit when we picked out. As Pat said yesterday I think, no one had you, at the top of the most likely to get some dick pool at the start of the trip. But, I think this is perfect for your date." I still couldn't tell if Sarah was being angry, sarcastic, or trying to be funny.

I stepped into the skirt and pulled it up. There was a small zipper on the side and once that was pulled into place the skirt fit perfectly. The waist was a little higher than what I was use to but now I realized why the shirt was a little shorter. The skirt was a skater style that flared out but stopped about mid-thigh, I was going to be showing a lot of leg.

When I looked in the mirror I knew I was to old to be wearing this outfit, I also knew that I was going to wear it. I loved it. The make up with it was perfect. While it was obvious I wasn't a twenty something year old girl, Jordie's makeup could only do so much magic, I was definitely a girl. I also decided that before being asked, or maybe because I wanted to feel a little control, to do a quick twirl in the mirror.

"Yea, you will need to be careful doing that in public or everyone is going to see your panties." Pat said.

"Oh My God. Do that for Steve one time and he will be begging to put his cock in your ass." Again Sarah's tone and facial expression didn't completely match.

I ignored her, instead I asked. "What about shoes? I don't think my flip flops will go with this? Sarah can I borrow your white t strap sandals?"

"Yep, she is definitely a girl now. Worried about making sure her shoes match her outfit." Jordie was smiling and her tone was warm and friendly.

"Yes. I will grab them and then we need to get to breakfast so you won't be late."

The walk to the back of the ship interesting. My outfit got lots of looks. There was about an equal combination of raised eyebrows, appreciative smiles, and several men doing double takes to get a better look at my legs. Once again I walked next to Jordie and I heard Sarah telling Pat that skirt was doing a good job of teasing a great ass under it.

I had a small breakfast. The table was kind of quiet this morning. A few comments about the weather. Sarah told Pat and Jordie what to expect as we got off the boat and would be accosted by Bahamians outside the gate. We confirmed the plan to meet at the Margaritaville for a drink.

Pat then picked up a banana. "Ready for your lesson?"

I turned red. "Here?" I wasn't sure if I meant in public or in front of Sarah.

Sarah saw my quick glance at her. "Don't be embarrassed about it because of me. It isn't like I don't know what you are planning on doing."

Pat had peeled the banana and placed it in her mouth being able to get about half of it easily in. She slowly slide it back out. Stopping and she opened her mouth to show she was circling the top of the banana with her tongue.

"That's all there is to it for the beginner lesson. Get as much as you can in your mouth, use your tongue, watch out for your teeth, and act like there is nothing in the world you would rather be doing than sucking on his dick. We can work on deep throating and being throat fucked later."

All three of us looked at her with shocked expression at the last two comments.

"What?" She laughed.

"Are you planning on swallowing?" I was a little surprised that Jordie asked the question.

Another quick glance at Sarah whose eyes showed she waiting for the answer also. "Yes, I think."

"Gross, but you do you." Sarah said quickly.

"It is an acquired taste." Followed by her amazing laugh, Pat broke the ice again.

I had been dying to tell someone this since dancing with Steve last night. I started to say something to Sarah in our room before bed but held back. I decided at this point it wouldn't matter.

"Last night when we were dancing. He pulled me tight against him and I could feel it against me. It was hard and felt like it is pretty big. I am a little nervous about that."

All three of the others laughed out loud at that.

Sarah jumped in. "Welcome to the club of having been grinded on. Of course I am sure I speak for the three ofus, when I say that happened to us the first time a really long time ago. Like a really time ago at some of the first dances we went to in school." She had glanced at Pat and Jordie who were nodding.

"I am sure you will be fine. If it is big and begins to hurt your mouth or jaws. Remember the tongue right behind the head and some hand action will go a long way." Pat interjected.

"Yes, and some ball licking and plenty of eye contact, especially with the eye makeup I did today, and you will be done sooner." Everyone giggled at Jordie's comments.

I wanted to go back to the room and freshen up just a little, plus I needed to grab the back pack I had bought a couple nights ago. Jordie was hoping to get a picture with Goofy so she was running off to do that. Pat said she wanted to sit on the pool deck and drink some coffee for a bit before heading into town.

"Let me walk you back, Pat and Jordie I will meet you in the lobby at 10:30." Sarah said as she stood up.

The walk back to the room was silent. I think reality was hitting us both. I was dressed as girl, a very girly girl, getting ready to go on date with a man. There was also a better than average chance that I would have the opportunity to have sex, at least oral sex, with this man.

In the room I brushed my teeth again, teased my hair some more, and reapplied my lip stick. The last two things made me feel warm throughout my body. I had to admit to myself that everything happening right now made me happier than I had been in a while.

Sarah was sitting on the end of the bed when I stepped out. "Listen, I want you to know that I am excited for you. I am happy all these things you have dreamed about and fantasized about are coming true. I also will want to hear every detail about it this afternoon. Please, remember I love the person that is inside of all that feminine clothing."

We both had tears in our eyes and I sat next to her and hugged her again. It was ironic, we had shared more hugs in the last two days, while I was dressed as a woman, than probably the last three years.

"Okay stop. If you start really crying you will mess up Jordie's makeup work. You need to get going. Are you okay to walk there by yourself?"

I nodded yes. Scared to talk and that my voice would crack.

"Have a wonderful time. Every girl always remembers her first date. And be sure to DO things I wouldn't do." She forced a laugh at the end of her joke about me wanting to blow a guy and have a dick in my ass.

I laughed and said a quiet thank you as I pulled the rose gold sequined back over my shoulders and headed to the door. I am not sure why but the click of the stateroom door closing sounded like a slam to me.

On the walk to the elevator and the ride down to the lobby I felt like my breathing was suddenly off. I was just now realizing how anxious and excited I was. As I got out of the elevator a woman told me she loved my outfit and my confidence. I mouthed a thank you because I wasn't sure if she was saying that about an older woman wearing the outfit or she knew I was actually a man.

I saw Steve in the lobby standing with Lisa. I was a little surprised to see her there and wondered if something was going on. Steve also had a red rose in his hand . I walked slowly up to them, Lisa saw me first and she smiled widely as she recognized me. Steve following her eyes, saw me next, and his eyes immediately went from my face, to my tight shirt, to the short skirt. I then watched his eyes travel up and down my legs.

Lisa stepped away from him and came to me for a hug. "You look fantastic sweetie. Are you excited?"

I whispered yes into her ear. I broke away from the hug and stepped towards Steve who was holding out the rose to me.

"Thank you." Again trying to speak softly. I hated my voice right this minute.

"You look amazing." He was speaking to my chest and not my face as he said it.

I decided to try and lighten the mood and leaned in and whispered. "They are still fake. Tinkerbell didn't come in the middle of the night, sprinkle pixie dust, and I suddenly grew boobs."

He laughed. "Sorry. If she could do that would you want her to? And I will try and make sure I just stare at your legs and ass instead since I know they are real."

I was suddenly flustered again and I looked down at the rose in my hand. I was actually wondering about his question about suddenly growing boobs. And I loved that I knew he was sincere in his compliment of my ass and legs.

"Let me take your rose. They won't let you take it off the boat I am sure. I promise to take care of it for you. You two have a great time and Brandi make sure you DO the things I wouldn't do." Lisa gave me a huge wink.

I laughed and said. "Sara told me the same thing."

I felt Steve hand in the small of my back and he guided me towards the elevator we would need to take to get off the ship. He asked how my morning went and told me he had heard that I had seen Lisa earlier. I told him it was good and confirmed that running into her in the morning was starting to be a regular thing and that I enjoyed it. I then wondered if I was being stupid talking about his wife. So I quickly changed the subject.