Rock and Roll Sissy Cruise Pt. 02

In part 1 I took my wife on a 7 day rock and roll cruise.My wife loves rock and roll music and in her younger days was a groupie for many bands. My wife had seen sissy porn on my computer and thought it would be fun to explore this fantasy on the cruise, while she looked to hookup with some musicians. It wasn't until we were on board that I realized she had packed only woman's clothes.

"You will never see any of these people on this ship ever again. I think you will make a cute woman."

To my surprise I enjoyed dressing in sexy lingerie and wearing lipstick. On the first day of the cruise my wife disapperared for awhile leaving me alone to get hit on by horny guys. When I returned to our room I found my wife giving an old friend a blow job. Being incredible turned on and encouraged by my wife the next thing I knew we were both sucking his huge cock and getting a load of cum on our faces.

Part 2.

"This is going to be a great cruise.Get cleaned up, refresh your lipstick and let's get ready for dinner."

As we go downstairs to dinner I notice men still staring at me, but for some reason instead of being self conscious I find myself excited. At dinner we are seated with two married couples maybe a few years older than us. Since we all share the same love of music the conversation is easy. Everyone is talking about their favorite groups and concerts they had seen. After a drink or two my wife starts talking about her groupie days and mentions a few of the rock stars she had fucked. I could tell the woman were a little uncomfortable, but their husbands were getting excited.

Then she says. "Brianna and I have a bet to see who can suck or fuck the most people on this cruise."

I feel the need to jump in. "My sister has a weird sense of humor, and it gets weirder when she drinks."

We all have a few laughs. When the couples get up one of the husbands passes my wife a note.

"My wife and I are into kinky sex. Why don't you and your husband, I mean sister stop by our room later. We have a great collection of dildos, and my wife knows how to use them."

My wife smiles and whispers in his ear. "We are checking out some concerts tonight, if we can't get to your room later we will hook up tomorrow."

After dinner we head back to our room. We have about an hour before our first concert. I am concerned that at least twice I have been discovered as a man, and I express these concerns to my wife. She reassures me that I make a very attractive woman, but need a little more coaching to be completely passable.

"You've been a woman for less than 12 hours, there are still a few things to learn. Tomorrow we will shave all your body hair. Trust me, you will love a shaved pussy. Your sexy lingerie will feel so much better. You need to improve your posture and your walking, and we need to do something about your erections. I see the way men look at you, trust me most of them can't tell. Now let's get dressed for tonight's show."

My wife is wearing a short dress with fishnet stockings. Her boobs are nearly popping out. She looks very much like she did in her groupie days when I first met her.

"How do I look?" She asked.

"Very hot"

She suggests that we wear matching lipstick, and she picks out a bright red. After we both put on the lipstick she kisses me and says. "If this doesn't get us laid nothing will."

"I'm not gay, I don't want to get laid."

"C'mon honey, you already had a dick in your mouth. Like I said, you will never see any of these people again, let's have some fun."

"I don't know what happened this afternoon, but I am not gay."

"What got into you was you saw your hot wife giving a blowjob and you got all excited. Trust me, once we shave you and make you more feminine you will want to get laid."

Again I said. "I don't want to get laid, I am not gay."

"Of course you are not gay, you are just a sissy boy. Believe me, after you have a big rock and roll cock in your ass you will be hooked. Just thinking about that first cock in my ass back in my groupie days is making my panties wet. I love you honey. Thank you so much for this cruise, and for being a good sport I promise you a lipstick blowjob before the cruise is over."

With that I calmed down a bit and we got ready to leave. My wife hands me a little designer bag. "Hold this and keep some makeup in there. You never know when you will need to freshen up your lipstick."

We headed to one of the venues which featured a couple of our favorite groups. I realized we hadn't been to a concert since before covid, and we were both really excited to see and hear live music. As the band began to play everyone was singing and dancing and having a good time. After the first set the drummer and the lead singer approached me and my wife. They introduced themselves as Tony and Frank. My wife invited them back to our room for some drinks and they both said yes. In the elevator my wife was making out with Frank. Tony started kissing me, and without thinking I opened my mouth and our tongues met. We continued making out as we got to the room. Once inside Frank started to unbotton my wife dress then started playing with her tits and sucking on her nipples. My wife was moaning as she feeling his cock thru his pants. Tony was feeling me up while whispering in my ear how big his cock was and how he was going to fuck me. I was afraid he was going to notice my raging hard on, but before that happened he stopped touching me and said. "Sorry Brianna, I am not into hairy chicks. I think I should leave."

I asked him not to leave, but he started toward the door. Just then my wife said. "Don't leave Tony. I can handle two guys. You and Frank can both fuck me, while Brianna reveals her little secret and watches the three of us. Brianna, why don't you show the boys your little secret."

With her encouragement I pulled down my panties and showed them my cock.

My wife said. "I caught my husband watching sissy porn and I thought this cruise would be a good chance to explore his feminine side. He really seems to enjoy it, but we still have some work to do. Tomorrow I will shave him and work on some female skills."

Tony said. "Sorry the hairy chest and legs freaked me out. Maybe tomorrow I can help her with her cock sucking skills."

"She sucked her first cock yesterday, but hasn't swallowed cum yet. Brianna would you like to suck Tony's cock tomorrow? You don't have to answer, you little clitty just grew. Why don't you take notes as I suck and fuck these two rock stars."

Frank was the first to pull his cock out.

"Wow, that's huge. I better refresh this cocksucking lipstick."

My wife put on lipstick, came back a minute later and immediately started sucking Frank's cock, giving me instructions as she goes along. "Lick, then suck, don't forget to play with the balls."

Tony was fingering her under the panties while her moaning got louder and her breathing heavier. Finally Tony pulled the panties off, spread my wife's legs, and began fucking her. There she was fucking one guy and sucking another. I was incredibly turned on and she knew it. So did Tony and Frank.

"Look at your sissy husband just sitting there with an erection, licking his cock sucking lipstick lips as his wife gets fucked by two huge cocks."

Tony started fucking her harder and harder, my wife's moans were getting louder and finally she screamed. "I'm cumming." As she came Tony also came, shooting a giant load into her pussy. Moments later Frank shot his load into my wife's mouth. But rather than swallowing she signalled me over and had me open my mouth. She then spit all the cum into my mouth as the boys cheered her on.

She asked me if I liked my first load of cum. After I said yes, she said. "Good, now be a good sissy and lick Tony's load out of my pussy."

I did as I was told. Frank then said. "We need to get back for our second set. Hope we see you tomorrow."

Then my wife said. "I hope so too, Brianna what do you have to say?"

"Thank you for fucking my wife."

After the men leave my wife looks at me and smiles. "I must be getting old, in my groupie youth I would never be tired after fucking 2 guys."

"No sweetheart, you are not getting older, you are getting better. I can't believe how hot you looked tonight sucking a cock while getting fucked.

"I'm glad you liked, it's been a fantasy of mine for awhile. I was afraid you wouldn't be into it. Sorry you didn't get to suck cock tonight. Let's go to bed, we'll wake up early, I'll shave all your body hair and make you more feminine and beautiful than ever. Tomorrow my sissy will get her chance to shine."

Just then there is a knock on the door. My wife answers it. A very tall athletic man is standing there. He introduces himself as Big Joe.

"Frank and Tony sent me, I understand there is a sissy boy in the room. It just happens I might be in the market for someone to be my sissy slave for this cruise."

"That would be my husband, I mean my sister." My wife answers.

Big Joe walks over to me and orders me to stand. I find his size and his confidence to be a turn on that makes me excited and nervous at the same time. I timidly stand as he checks me out.

"Not bad." He says, then he asks my wife. "How long has Brianna been dressing up?"

"She just started on this cruise, she still needs my help with some clothes and makeup. Tomorrow I am going to shave him."

Then he spins me around, grabs my boobs and spanks me in the ass.

"I hope you like to get spanked."

It hurt a bit, but I said yes.

Then he said. "That's yes MASTER Joe to you."

"Yes master Joe, I like to get spanked."

My wife is sitting on a chair. She seems to be enjoying the way Big Joe is controlling me.

"Ok sissy, go freshen up your lipstick, if you do a good job I will let you suck my cock."

"Yes master Joe."

I do as I am told, put on my slutty red lipstick and wait for Big Joe's approval.

"Very nice." Then he asks my wife if she wants to watch me suck his cock.

"I would love to."

Big Joe takes his pants off. Wow, they don't call him Big Joe for nothing. My wife says. "That's the biggest cock I've ever seen, and I have seen plenty."

I nervously say. "I don't think I can fit that in my mouth."

"What did you say??"

"I don't think I can fit that in my mouth Master Joe."

"I think you better if you want to be my sissy slave. Now get down on your knees and suck my cock."

Remembering a little of what my wife tried to show me earlier I start licking and kissing up and down the shaft of his giant cock. I start licking his balls. Joe seems to approve which makes me happy.

"Nice job slut, now take it in your mouth and start sucking."

I start sucking on his cock. He forces down my throat and he is fucking my mouth. I am gagging, but I keep sucking. He starts smacking my ass and I start sucking harder and faster. Finally he cums. It seems to last forever. I swallow most of it, the rest drips on my face.

"Not bad for a beginner he says, but you need a little practice. Tomorrow after you shave your body hair I want you to pick up a random guy and suck his cock. I want your wife to video it and send it to me. If you do a good job, and your pussy is completely shaved I will fuck your tight little ass and you can be my slave for the rest of the cruise. Would you like that?

"Yes I would master Joe."

Big Joe gets dressed and gets ready to leave. I think him for letting me suck his cock, and he slaps my ass again. As he leaves he whispers something to my wife. After he is gone my wife gets me a plastic cup. She tells me to jerk off into the cup. I take my dripping wet panties off as my wife grabs her cell phone and photographs me jerking off. Within seconds I explode into the cup.

"Now smile and drink your cum."

"What a night." She said. "I think Big Joe likes you."

"I hope so, he is so big and strong, and very good looking."

"Plus he has a huge cock." My wife adds.

"Yes, that too. I am afraid it might hurt if he shoves it up my ass."

"Trust me, you will love it. Once I took my first cock up my ass I was hooked. I think my Brianna has a crush on Big Joe. I am so glad you are enjoying the cruise. Now let's get some sleep. Tomorrow is going to be a busy day."

To be continued.