Finally a Princess Pt. 04

"So were you in the gym this morning?"

"Yes, I start most of my mornings there. I find if I don't do that first thing the chances of it happening are way less."

"Well, I can tell you that your efforts in the gym definitely pay off." I flashed him a big smile as I said it.

We reached the point where you disembark and Steve motioned for me to go first. When I touched my Key to the World card on the scanner the Disney Cast Member suddenly looked alarmed. He motioned for me to stop and step off to the side. Another Cast Member quickly stepped up to him and he pointed at the screen and then me. She nodded and asked me to step over in a corner.

I immediately knew the problem. When we checked in at Port Canaveral I had my picture taken with Sarah. I definitely did not look like Sarah and I didn't look a lot like Brad.

"Uh... I know what the problem is. My appearance doesn't match my pic right?" I had moved close to her and was speaking as quietly as I could. "I am transgendered and came on the boat in my boy stuff but since I have been on it I have been pretty much in girl mode."

"No problem. I understand. You look great. I love your outfit. I do want you to be cautious though sometimes the local's don't take kindly to members of the LBGTQ community.

Are you with him?" She pointed at Steve.

I nodded and smiled while looking at him.

"I am sure you will be fine then. Have a good time."

I moved through the line and Steve took my elbow in his hand and steered me to and down the gang blank. He asked if everything was okay and I gave him a quick review of what happened. I was fairly embarrassed telling him. He sensed that and stopped and hugged me.

"Trust me. I see a woman when I look at you, there is no reason to be embarrassed."

I was glad I had put on my sunglasses, or actually a spare pair of Sarah's, so he couldn't see the tears building in my eyes. He asked me what direction we needed to head and I found my hand in his as we ran the gauntlet of vendors offering jet skiing, taxis, tours, etc.

The walk to the museum was about ten minutes and we didn't talk much. The streets were noisy and I think we kind of needed to reset and get back to date mode. Steve went to the desk and paid for us both even though I protested and offered to pay.

We moved through the museum and discussed the different things we saw. I explained that I found the age of piracy fascinating. I also said that I understood that pirates were, basically , people that did terrible things but I choose to like the more fictional, romanticized version of pirates. Whether it was the book Treasure Island, or the Pirates of the Caribbean movies.

He asked me if I had watched the show Black Sails and I immediately lit up. "Yes, I loved it. I have actually watched it twice."

"So, which character do you identify with the most. Elanor, Max, Anne Bonnie or Flynn?"

It was a really interesting question and honestly it made me a little more attracted to him. Elanor and Max were definitely the most girly characters. Elanor was bisexual who used men to advance her own ambitions. Max was obviously a lesbian but as a prostitute slept with men. Anne Bonnie, who was based on a real person, was heterosexual female pirate but definitely a tom boy. Flynn, was the only male in the group and was bisexual but eventually fell in love with another man.

"I think if I was picking who I would want to be it would be Elanor. If I was picking who I would want to do, it would be Flynn." I gave him a big smile with a blush as I said that. It was true. I had a big crush on Flynn during the show, the guy was hot.

Steve smiled and took my hand in his as we moved through the rest of the museum. My heart was once again racing and I started to think about what would eventually happen today, or at least I hoped would happen. Would he be bold enough to make the first move. How would we get to a situation where we were alone and in private.

We got to the end of the tour and it emptied us into a gift shop. I saw a clock and realized that we had about a hour to kill before we were supposed to meet the others at the new Margaritaville. I figured it was about a 15 minute walk. Steve glanced at his watch, I think was doing the same math.

"Do you like Bloody Mary's?"

"I love them. Why?"

Steve asked the woman working the gift shop counter where we could get the best Bloody Mary and she told us about a bar right around the corner. It was on the second floor and had a deck that looked our over the harbor and you could see the cruise ships. He thanked her and we were on our way there.

We enjoyed our drinks and discussed our previous Disney's cruises. There was a tension in the air and I sensed that he was thinking about what was going to happen if we were alone. I got bold and made sure that while not messing up my lipstick to much I left red marks on my straw. I saw that Steve had noticed that. When I pulled the celery stalk out of the glass and slowly sucked it into my mouth his eyed widened.

"We probably need to head over to the Margaritaville so we can at least make an appearance before heading back to the boat to go to the pool."

Steve nodded and waived the waitress over for the check. She complemented me on my skirt and when he paid, as he counted out the cash to pay, her she mouthed to me, he is hot. I nodded vigorously and we both laughed. He gave her the cash which included a generous tip and she thanked him and walked away.

As we walked out onto the sidewalk he asked. "What were two you to laughing about back there?"

"It was a girl thing."

"Seriously, you can tell me."

"She mouthed; he is hot. I let her know that I totally agreeded with her." I told him while grabbing onto his arm with both hands and pulling myself against him.

The walk to the Margaritaville was about 10 minutes or so and again because of all the road noise we didn't talk much. I was also a little nervous that once we meet up with the group the date would be over and I really wanted at least the opportunity to kiss him. Oh hell, I was kidding myself, I wanted to at least suck his dick.

We stepped into the lobby of the bar area and of course the first person we heard was Lisa yelling that they were all over here. We slowly made our way there and got to the long table. They had saved us two stools on the end next to Pat and Lisa, and across from Sarah and Jordie. Nancy and Melissa were across from Lisa and Pat and Susan and Devon were on the end.

There was a chorus of hellos and questions about the museum. We asked how the market was and in the middle of it a waiter asked if we wanted drinks. I saw that pretty much everyone but Devon had a margarita so I ordered one also. Steve ordered a Landshark. We were told that we had to catch up, that this was everyone's second drink, Steve informed them that this was our second also. We had stopped for a Bloody Mary.

The waitress dropped two huge plates of nachos in front of us and another brought our drinks. I noticed that Sarah was watching me and Steve intently while Jordie was watching her mom and Lisa. I raised an eye brow to Jordie and tilted my head towards Pat and Lisa and got a big smile and wink in response.

Steve had leaned behind me and had a silent hand signal type conversation with Lisa. Right after that he decided that we needed a round of tequila shots and ordered them from the waitress. I heard Pat tell Lisa that she would need to slow down or she would be making bad decisions. Lisa replied to her, asking if they would be bad decisions or fun decisions. Pat gave her amazing laugh as a response. After our shots were brought to the table, and toasts to fun times and bad decisions were made, we all downed them.

The Bloody Mary and Margarita had got to my head I think. I turned to Steve and my hand ran up his thigh, over his shorts and let it come to a rest cupping his dick, which was growing in my hand. I brought my lips to his ear and said. "Sweetie, you don't need to get me drunk. I am a sure thing if you get me alone."

His eye widened and he announced to the table. "Well I am ready to head back and enjoy some quiet time at the pool while everyone is off the boat. Anyone else heading back now?"

"I am ready." I said.

Sarah half said under her breath. "Yes, I saw that you were ready." I realized she had seen or at least figured out what I had done with my hand.

The far end of the table said they still wanted to do a little shopping. That was followed by Sarah and Jordie saying the same thing. Pat and Lisa were actually whispering between themselves while suddenly looking like they were very friendly.

Steve and I stood up and he turned to Lisa, told her to pay for all this when the bill came, we said our good byes saying we hoped to see everyone at the pool. As we started to move to the door Sarah reached out and grabbed his arm.

"Be good to her. Also a little advise, save some for later and you might be able to get some pirate booty, I promise you won't be disappointed."

I had no idea what the second part meant but I had a sudden hesitation to race back to the ship because of her kind words about being good to me. Steve had replied with a simple I will, placed his hand on my back and led me to the door. When we got outside he saw a cab and grabbed it. Telling me it would get us back sooner.

As the cab made the quick trip towards the ship, and it grew larger, I grew more nervous. The brief bit of confidence that I had shown right after the Tequila shot had rapidly disappeared. I looked at Steve out of the corner of my eye and he caught me. His hand reached out and landed on my thigh and gave it first a small squeeze and then slowly starting circling his fingers on top of it.

We arrived at the port and as we started up the gang blank, I remembered what had happened when we had disembarked, I hoped that I wouldn't run into that problem again. I took the back pack off, set it on the scanner belt, stepped through the metal detector, and tapped my Key to the World card and went onto the ship. No problems.

When we got to the elevator I am pretty sure that my anxiety was starting to show. I couldn't stand still and I definitely couldn't look at Steve, especially in the eyes. Was this how our date ended? With silence and awkwardness. Somehow I found the courage to speak.

"So, you are going to change and head to the pool now?" I stared at the elevator door as I said it.

"I guess, what are you planning on doing?"

"Go to the pool also I guess." I turned to him and somehow managed a smile and heard the elevator door ding signally it's arrival. The doors opened and two families got out. Steve and I were the only ones that got in.

"Would it be okay if I walked you back to your room to make sure you get back safely?" He asked with a strange grin on his face.

"Of course. That would be nice." I meant that.

In what seemed like seconds, we were standing at my door and I touched my card to unlock it, the click of the lock releasing sounded like a gun shot. I grabbed the handle with one hand and pushed it down while backing into the door. Steve stood there just looking at me. I am sure he was wondering what had happened to his sure thing.

"Uh. Okay, See you at the pool." He said.

I reached out with my other hand and grabbed his forearm and pulled him into the room. A smile spread across his face. We cleared the door as it closed behind us. Hearing the door shut must have emboldened him because suddenly I was pulled tight against him and his mouth was on mine. Our tongues found each other and we kissed passionately as we moved slowly deeper into the room. We made it past the bed and at some point his back was now in front of the couch.

When his hands found my ass he pulled me tight against his groin and he was obviously hard already. I rubbed and grinded against it and then slowly broke the kiss and stepped back. My hands went to his belt and after a slight fumbling, I released it and unbuttoned and unzipped his shorts. The shorts and belt fell to his feet with a thud. I ran my hand over this cock that was still covered by his boxer brief, while he pulled me in again for more passionate kissing.

I broke the kiss and sank down to my knees. I had fantasized many times about being in this position, the fact this was now, suddenly, caused adrenaline to run through me. My mouth kissed his dick through his shorts and I could hear him moan and felt his hands run through my hair. I rocked back on my knees and looked up into his eyes and smiled. The smile he returned to me made my insides melt and I slowly pulled the band of his underwear away from his body and worked them down over his cock.

I might have gasped as his dick sprang from the confines of his underwear. I first saw a pronounced round head with a significant ridge around it. Then I saw the delicious looking veins that stood out just begging to have a tongue run over them. As I pulled his underwear past his knees I got a good look at his large balls that were neatly shaven. I also caught an amazing, musty, manly scent.

I pulled his briefs down to his shorts and helped him step out of them. My mouth went to his balls and I gave each one a slow lick, then traced my tongue up his dick before giving the head a quick kiss. Again, I heard Steve moan and his breathing start to become faster. I stood up and with one hand firmly wrapped around his cock I kissed him hard on the mouth before using my other hand to push on his chest and force him to sit on the couch.

Sinking back to my knees, I looked at my hand wrapped around his dick and the first thing I noticed was my red nails and a quick glance up saw that Steve was noticing this also. I also realized that my hand barely made it around his shaft, he was fatter than I was. It was also very obvious he was longer. At least seven inches but probably eight. His dick was beautiful.

I moved my mouth down onto it and felt the ridge of the head on my tongue. The taste of it was a bit salty and I loved it. I got as much as I could in my mouth and took that moment to look up at Steve and into his eyes. I heard "Oh God" from him. My hand wrapped back around the shaft and began to bob up and down while circling my tongue over the head and sucking. Steve had his hands in my hair and was stroking my head. I noticed he was breathing faster and when my other hand went to his balls I could feel them tightening.

I was just getting started and I wanted to savoir the taste of his delicious dick so I backed off and ran my tongue over every vein I could find, again making sure to look up into his eyes as I did it. I then moved my mouth to his balls and licked and sucked on them. This got a "Jesus Brandi!" response.

I moved back to take him in my mouth again and went back to bobbing and sucking. I was loving this and knew I would be doing this again and again. With one hand wrapped around the base of his shaft I started jerking, with the other hand I started caressing his nuts. I heard "Holly Fuck" and felt his balls tighten more and his shaft somehow get even harder. I knew that he would be cuming soon.

"Oh Brandi, that feels amazing. I am going to cum soon."

I just looked into his eyes again and, while I am sure he couldn't tell because my mouth was full of his dick, I smiled.

"Oh Fuck. I am going to cum." When he said that he removed his hands from my head. I assumed this was to allow me to remove my mouth from this dick so he wouldn't cum in my mouth.

I sucked harder and felt his dick began to pulse as he screamed. "I am cuming! Jesus Brandi!"

The first shot of cum slammed against the roof of my mouth and he just kept spurting more out. I was swallowing as fast as I could while trying to taste it. There was so much, some of it some leaked past lips and I felt it trickle onto my chin. He continued with small spurts. Again, I looked up to meet his eyes and in his smile I saw content but also something else, admiration, feelings, I wasn't sure. It made my heart want to explode.

Once I was sure I couldn't suck out another drop. I leaned back and looked at him while I used a finger to scoop the cum on my chin into my mouth then leaned back down and licked up the little bit that was on his dick.

"Well, that was yummy." Again looking right at him as I said it.

"Oh My God, that was amazing. Was that the first time you have done that?"

I nodded as he motioned for me to sit next to him on the couch. As I sat down, he wrapped his arm around me and gave me a quick kiss on the lips. I wanted a deeper kiss but wasn't sure if he was reluctant to do that since he had just cum in my mouth.

"Well you are natural cocksucker then. That was the best blow job I have ever had."

Cocksucker. Wow. I guess that was true, I was now a cocksucker. I smiled at him, not really sure what to say but finally went with. "I am glad you liked it. I hope to be able to do it again."

He leaned down and kissed me again which made me feel good. I know that lots of men, after orgasming all the sudden have guilt. I wasn't sure if I was the first guy that had ever sucked him off but even if I was dressed a girl, there was no denying I was guy. I stole a quick glimpse at my at my crotch to see if my hard penis was evident, hoping it wasn't.

"Uh. So Brandi, that was my first time with a guy. And even though I know you looking nothing like a guy right now. I am not gay so..."

I immediately knew where he was going. "Relax Steve, I have no expectation of you returning the favor. I wouldn't want you to, even if you were interested. This is about you being a man, and a fucking hot one at that, and me feeling like a woman."

I could see the relief on his face and he leaned in and kissed me passionately again. When he broke the kiss he said. "And you are a hot woman!"

I had snuggled in closer to him with my head resting on his chest area. My one hand had fallen to his thigh and eventually onto his dick which I was just softly rubbing my fingers over. One of his hands had pulled up my skirt and was running over my panty clad ass.

"Will you tell Sarah about this?" He asked kind of out of nowhere.

"Yes, she told me she wanted to know every detail about my date."

"How will she take it?"

"I really don't know. She seems to encourage it one minute and the next she says things that I am not sure if they are harsh jokes, or veiled comments. I do know though without her help and support I would have never experienced this."

I raised up and kissed him again, this one was somewhere between passionate and tender, after the kiss I lowered my head to his lap. This gave him better access to my ass which he was now fondling aggressively. I took his soft penis in my mouth and almost nursed on it. I felt it stiffen some and was a little hopeful that I might get the chance to taste him again.

"That feels nice Brandi but I don't think he is going to be ready again so soon. Unfortunately, it takes a little time to recover these days."

I sucked for about a minute more and then sat up and looked at him. "Do you think he will be recovered by this evening. Remember Sarah mentioned pirate booty later. I am hoping she was hinting at what your hands were on a couple minutes ago."

He laughed. "I am pretty sure by this evening he will be ready to go again." I saw him look at his watch. "Wow, we left them over a hour ago. They will be back soon. Not sure I want them, and especially Sarah, to catch me without my pants on."

It was my turn to laugh but I got off the couch and on my knees again helping him put his feet into the boxer briefs. I kissed the tip of his dick one more time before pulling the briefs over it. Next I assisted with his shorts. I stood and kissed again. "Thank you for a day I will never forget."

"No, thank you. Umm, you might want to work on that lipstick before Sarah gets back also."