Rock and Roll Sissy Cruise

My wife and I are in our late thirties. Our 10th anniversary is coming up and I wanted to do something very special. I saw an ad for a rock and roll cruise. One week at sea with over 50 rock bands including some of my wife's favorites. The crusie also stopped at a couple of Carribean ports, plus the cruise ships private beach.

I had met my wife some 15 years ago at a concert. She was a groupie and she use to brag about the rock stars she had sex with. It was one of the things that turned me on about her. As part of our unwritten wedding vows I gave her a hall pass whenever one of her favorite groups came to town. She would often ask if I were interested in a threesome with one of the guitarists she would have sex with, but I wasn't interested in a threesome with another guy. "Maybe a threesome with another woman." I would tell her. But she wasn't into that.

The past few years my wife had lost a little interest in her rock fantasies. She started her own business and was very busy. And although she was still extremely hot looking she didn't seemed to be interested in competing with teens and 20 year olds to get back stage and fuck a rock star.

All that seemed to change when we went out to a romantic dinner and I told her about the cruise. When she went online to see what bands were on the cruise she started to get excited. Some of her favorites were performing.

"I have three weeks to get in shape." She said.

"You are in great shape." I told her.

"I am not in fuck a rock star shape." She answered. "I need to get some bathing suits and some sexy outfits. There shouldn't be any teenages or 20 somethings on this cruise. They are so annoying, that's one of the reasons I stopped going to concerts.

As the date for the cruise got closer my wife was getting more and more excited. She would continually thank me, and she would show me the new outfits that she had bought.

The week before the cruise I was incredibly busy at work. I needed to be 110% caught up because I knew that I could not be reached once the ship had departed. I was working 12-16 hour days, but it was worth it to see my wife so excited.

Knowing how busy I was my wife did all the last minute organizing and packing.

It was about a 5 drive to the Miami port, so we got up early on a Sunday morning and drove to the ship. The boarding process took about an hour, then we settled into our room. We had been given an upgrade and had a beautiful room with a balcony. We had about 3 hours to relax before an orientation downstairs where we would learn all about the ship and the schedules for the concerts, so I decided to take a quick shower.

When I got out of the shower I opened my suitcase to get dressed. To my surprise, my suitcase only had women's clothes. When I questioned my wife she said. "I thought it would be fun for you to dress like a woman for the week. I caught a look at the porn you have been watching, and I see a lot of sissy crossdressing videos."

Embarrassed that I had been stupid enough to get caught I replied. "That's just something I watch, I don't want to dress on a cruise ship."

"I can tell by the way you look at my panties or watch as I put on lipstick that it is more than just something you watch. I think you will look cute, you have some feminine features. Besides you will never see any of the people on the ship ever again. Let's try on some of the clothes I bought for you."

She takes out a pair of sexy panties and tells me. "We are each going to wear matching pink panties tonight, won't that be hot?"

I didn't answer, but when she put the panties on they felt amazing, and I couldn't hide the erection from my wife.

"See, I told you that you would like this. Let me help you with the matching bra."

She squeeze my breasts and said. "Nice tits."

Next she helped me put on a pair of black sheer stockings, and my erection grew even larger.

"If you can't control your erection I will have to put your dick in a chastity cage."

Next she gave me a sexy dress and ordered me to sit by the mirror. She put on some blush, then began to work on my eyes. Mascara, eyeliner, and eye shadow.

"You have such pretty eyes, and now they look so feminine. Then she added a pink lipstick and a sexy shiny lipgloss, and to top it off she put a blonde wig on my head.

"Look in the mirror." She ordered.

I could believe I looked like an attractive woman.

Before I could say anything she said. "You are welcome. For the rest of the cruise you will be my sister Brianna. We still have work to do, but for now let's go downstairs to orientation. I wonder if there will be any rock stars there."

We go downstairs and listen to a couple of speeches, then we go to get a little snack before dinner. I am feeling very self conscious. I can swear many of the passengers can tell I am a man, but my wife insists that it's just my imagination. "I think you look great, I think I am jealous that more guys are looking and hitting on you."

"You are crazy, you are the hottest woman here."

My wife excuses herself to get a drink.

As I sit there a handsome man in his 40's comes up to me. "What's a pretty girl like you doing sitting here all alone?"

I tell him I am waiting for my sister and we make small talk for awhile. When he starts feeling up my stockinged leg I get nervous and excited at the same time. Then he says. "Come back when you shave your legs sissy boy if you want to have sex on this cruise." Then he kisses me and grabs me ass.

At this point I don't know what to feel. My wife has disappeared. I have guys hitting on me and I don't know if they think I am a man or a woman. As I start to panic I decide to walk back to our cabin. When I open the door I see my wife sucking on a giant cock. She takes the cock out of her mouth and introduces him to me. "This is Phil, he's with the band. Phil, this is my husband, I mean sister, Brianna."

I explain to my wife what happened.

"Don't worry, after another day or two nobody will be able to tell you are a man. Just go with the flow and enjoy it."

Then Phil chimes in. "You look hot Brianna. Most of the guys in the band prefer sissy boys. That way their girlfriends or wives don't get jealous."

Then my wife asks. "Did you get excited watching me suck Phil's giant cock?"

I couldn't lie, it did get me excited. Then Phil said. "Look at that bulge in his panties, he is definitely excited. Come over here and get a better look."

As I walk over to the bed my wife starts sucking Phil's cock again. When I get closer my wife stops for a second, takes my hand and places it on Phil's cock. I am giving him a hand job. I am so excited, without thinking I get on my knees and start sucking. The next thing you know my wife and I are both licking and sucking his cock. Moments later his pulls his cock out and shoots his cum all over our faces.

Phil gets out of the bed, pulls his pants up and says. "See you guys after our show tonight."

My wife says. "This is going to be a great cruise. I just knew you would love to suck cock. Now freshen that lipstick and let's get ready for dinner."

To be continued.