Views: 545 Created: 2015.06.06 Updated: 2015.06.06

Caribbean Cruise In Diapers and Dresses

Part 2

I quickly get to the elevator and go up to the room, as I enter I hear moaning and quickly discover that Ginger in the middle of the best orgasm of her life, I sit down at the foot of the bed and begin to masturbate in my diaper at the site of this sexy women pleasuring herself. It is then that I hear my wife scream in pleasure. Ginger looks over and sees me masturbating out of the corner of her eye; she announces, “I see the sissy is back.” I continue to masturbate and shoots the largest wad of cum I ever have. Exhausted, this was truly the most exciting and erotic thing I have ever seen. Ginger notices me pinning my diaper back up and comments on the fact that “I must like my diapers if I am putting it back on myself.”

As I finish pinning my diaper up and straightening out my dress, the doorbell wrings. Ginger tells me to get the door. I slowly walk to the door in fear of someone else seeing me. Upon opening the door, I notice it is the girl from the club. Ginger laughs introduces me to Veronica and then says “you will address her as Miss Veronica, do you understand” I nod my head yes. Get your little diapered butt straightened up, we are going to dinner.

I look in utter shame at these two sexy women. Veronica in a black PVC cat suit and Ginger in black leather pants and a sexy black bra. Both of them have on sexy high heels and perfect makeup. They grab my hand and we rush out of the hotel room to the elevator, a short ride to the top, we end up in the penthouse restaurant as we walk in everyone is staring at me or so I think until I realize that they are actually staring at the two beautiful women I am with, especially the men. It is then that a group of four college age girl’s looks at me and laughs and make several comment on what a pretty dress I have on. I turn bright red in humiliation, we are led over to a table and Ginger hands Veronica a bib to put on me, I push it away telling her “I am not going to wear a sissy bib” Veronica looks at me and laughs “You tell me you will not wear the bib, but here you are a grown man dressed like a sissy in diapers and plastic pants showing underneath your baby dress.

Everyone in the restaurant turns starts to whisper and laugh as the group of girls speaks up again and say “I told you he was wearing diapers” One of the girls just replies “some men never grow up” Veronica ties the bib around my neck and we sit through the rest of the dinner to some occasional comments from other people. After dinner Veronica tells Ginger she has to get back to work. We walk down to the lobby with her she wishes us a great cruise and pats me on my diapered bottom, telling me to be a good sissy for mommy.

We return to our room where Ginger takes my dress off and pulls an onsie over my head snapping the crotch. Gingers asks me if I enjoyed my day, I get in to bed and quickly go to sleep.

I wake up the next morning as Ginger is already busy getting ready to leave for the ship. I jump in the shower and by the time I get out my clothes for the day are laying on the bed. She tells me that she wants me comfortable for my first day on the ship. In know time she has me diapered in a disposable diaper and blue nursery print plastic pants. She pulls a simple surfing T-shirt over my head and then hands me a pair of shorts. By the time I get the shorts on I realize they are very short women’s athletic shorts, luckily navy blue. I look in the mirror and am happy to see that the diaper is not that obvious until I bend over, what is somewhat obvious is the fact I am in women’s shorts. She hand me my shoes, which are basically women’s low white canvas keds with ankle socks. We check out of the hotel and take a taxi to the cruise port.

Check in is extremely fast and efficient at the cruise port, we even get upgrades to a large balcony suite. Once on the ship, Ginger suggests we go up stairs for the Bon Voyage party, our luggage has not arrived yet and she warns me against wetting my diaper. Up on the top deck everyone is dancing and having a good time. Ginger tells me to go get us a drink. As I walk up to the bar a couple of college age girls pass me and comment on my cute shorts, one of them even points out the fact that she is wearing the same pair, except that hers do not bulge out like mine. I quickly thank them and head up to the bar. Once I get the drinks, I head back over to Ginger and run into the same two girls. This time one of them pats me on the butt and comments loud enough for everyone to here “I told you he was wearing diapers and by from what I can see now baby plastic pants.” She pats me on my now obviously diapered rear and tells me to go see mommy. As I walk away I feel the back of my leg and find that my plastic pants are drooping below my shorts in the back. When I get back to Ginger, I tell her what happened. She just laughs and tells me that this is my diaper cruise. The ship is just starting to leave the port and everyone is getting louder as we go by Biscayne Blvd. A young couple is standing next to us and introduce themselves as Cindy and Jeff. Ginger tells them to come to out room later for a drink. We head back to room and notice our luggage has arrived, which makes me happy, since I am in a soaked and about to leak diaper.

Ginger and I start to put our clothes away in separate closets. When I am done with mine it looks like nothing more then a baby’s closet with all the baby dresses, rompers, diapers and plastic pants. I go into the bathroom and put the baby oil, powder and lotion on the vanity and put the diaper wipes right next to it.

Ginger decides to finally change my diaper and put me in cloth with yellow nursery print this time. The ship has robes for the guests to wear and tell me to put one on. A short time later our doorbell rings. She looks at me real stern and say well open it. Cindy and Jeff have come by as invited. I fix them a drink and Ginger shows them around the room. Cindy cannot believe how big our bathroom and notices the baby oils and etc. She jokingly comments whose the baby. Ginger says, “Dave loves the smell of baby powder.” Everyone just laughs, but Cindy looks at my crotch area and smiles. After a couple hours of chatting with each other Cindy and Jeff decide they need to leave for dinner. As they go to leave we give each other a hug good by. As Cindy and I are hugging she pats me on the back and lets her hand drop to my diapered bottom. She whispers in my ear “I thought you were the baby in here.” I turn bright red as she promises not to tell anyone.

Ginger and I get ready for dinner and quickly go down to the dining room. The dining room is absolutely beautiful. After a great dinner we return to our room for a night of fun by ourselves. Ginger tells me “take everything off except for your diaper.” We craw into bed and have some of the best sex of our lives. I orally pleasure her for almost an hour as she returns the favor. With my diaper down in the front, I ask her to get on her knees and proceed to get her from behind. After another period of time, we are both totally spent. And roll over to go to sleep. I pin and fix my diaper up and fall to sleep within minutes.

The next morning I am soaked and have leaked onto the bed. Ginger starts to change me as someone rings the doorbell. I here Ginger and another girl talking and she instructs her to put a tray on the coffee table. I realize it is room service and try to cover up, but not before she gets a good look at my diapered condition and obvious soaked bed. On the way out the door, I here the girl tell Ginger she will request a plastic mattress cover for us.

After breakfast, we decide to go up to the pool and relax; Ginger has me in just a disposable, blue nursery print plastic pants and shorts for the pool. I found it easy to hide my diaper this time and thanked Ginger repeatedly. Once at the pool we run into Cindy and Jeff. Cindy smiles at me and says “how are you doing baby” Ginger smiles, but no one else thinks anything of it. We order some Pina Colada’s, which go to work on me fast. I am soaked within a couple of hours and whisper to Ginger that I have to change. She makes an idol comment of “make sure it is cloth this time. I excuse myself as Ginger and our two new friends continue to talk.

Once in the room, I decided to take a quick shower to prevent the possibility of diaper rash. As I was in the shower, I heard the door front open. It was Ginger, Cindy and Jeff. I quickly got out the shower and asked Ginger to please bring me my robe. Cindy yelled through the door that I better hurry they need the bathroom. As I walked out of the bathroom, Cindy was looking at me sort of funny and said sweetly that she had laid out my clothing for the day. When I walked into my room I stopped cold because on my bed there laid out was a white romper and pink plastic pants and bonnet as well as a fresh diaper. As I stood there frozen Jeff grabbed my arms and said “Lets get the baby dressed” Cindy then said she had heard I liked to be a sissy baby so for the day I could be her and Jeff’s sissy baby. I looked at Ginger for help, her only reply was “You left your closet open sissy boy and they saw your sissy baby clothing hanging in the closet, so I showed them everything to include all your dresses, sun suits and rompers.

Jeff then pushed me onto the bed and Cindy proceeded to powder and diapers me as Ginger laughed and watched. After I was diapered Cindy pulled my pink plastic panties over my legs and had me lift my butt so she could pull them over my diaper all the while she was commenting how she was going to love me dressed up. Next she placed my romper over my feet and pulled it over my legs and had me stand up so she could zip it up and then placed the bonnet over my head and tied it.

Cindy said she had heard about men that love to be treated like babies, but didn’t really believe it until she saw my clothing stash and Ginger told them everything. She asked if it was true that I liked acting like a baby sissy too? Almost in tears, I stood there and told Ginger I couldn’t believe she told them everything. Ginger just laughed and said “look he’s getting a hard on because he likes it so much”. When Cindy saw my diaper bulging from my hard-on she said that the baby needs to cum. Ginger told Cindy and Jeff she will take care of me and meet them at the pool. Ginger looked through the drawers and got out the new vibrating butt plug witch was about 6” long and 1.5” around. Ginger quickly removed the romper and pulled my diapers down, she then grabbed my legs and spread them wide so she could shove the butt plug in my ass then she pinned my diaper back on and she surprised me next when she put my locking plastic pants on me and dressed me in my blue sailor dress. Ginger told Cindy and Jeff to take the key with them to insure I would stay dressed that way until they were ready to release me. They all three left shortly for the pool.

As I laid there with my ass hurting I thought about what had happened and how much fun I had then remembered them talking about going back to the pool and invited us to go as well. Ginger left to go up to the pool with them and told me that I had better come up to the pool shortly, or that was just the start of my humiliation. I then realized that I would be stuck like this until I went to the pool. After lying there for two hours and feeling the batteries finally run down on the vibrator and completely soak my diaper, I got up and started looking for something to wear over the thick diapers, plastic pants and sailor dress. I finally decided on the robe, which did nothing to hide the fact that I was thickly diapered.

I finally get the nerve and leave the room, once up on the pool deck; it took forever to find them. Cindy was the first to see me and asked if I had enjoyed myself. I nodded my head. Ginger spoke up and told me to take the robe off immediately. I begged her to let me keep it on as Cindy stood up from her lounge chair and took it off of me. This leaves me standing in thick diapers and a sissy sailor dress, while everyone else is in nothing but tan bodied in bikinis and thongs, people start to notice me the entire pool deck erupts in laughter and cheering. In embarrassment I wet my diaper further and beg Cindy to give me the key, the three of them start to laugh and tell me they do not have the key, she just taped to the back of my plastic pants. So I could now get changed. I reach for the robe and Ginger tells me to get back to our room like I am now. As I am leaving the pool area, I run into the college girls, who just laugh and call me names, this does nothing more then bring more attention to the way I am dressed.

I finally make it to the room; after I got loose and had pulled the butt plug out I changed my wet diaper. After returning to the room, Ginger starts to laugh at me; she then asks “well sissy boy did you if I enjoy yourself?” I tell her “I truly did, but was never so humiliated in my life.” She tells me that we have dinner in an hour and to get ready. I feel lucky with the fact that I get to wear a men’s suit to dinner, even though I will be diapered underneath.

At dinner we run into Cindy and Jeff. Cindy gives me a playful pat on my diapered bottom and tells me they had a lot of fun and we should get together again as they have thought of other ways to play with the new baby.

Ginger and I go down to watch the Broadway type show later that night and relax with a couple of drinks. We return to the room shortly after the show to another great night of sex and promises of more diapers tomorrow. We are going to be in Cozumel in the morning and she tells me I will spend the day on the beach in just diapers.

Early the next morning, we are docked in Cozumel and Ginger is busy packing my backpack for the day. I am instructed to change myself and put on the pink plastic pants, T-shirt and shorts. After I am all dressed it is clearly obvious that I am heavily diapered under the short shorts.

We head out to disembark the ship and shuffle our way through all the people. On the dock we quickly get a rental car and head out to the private beaches. Ginger instructs me to take my shorts off, as I will not need them anymore today.

As we get close to the beaches, we decide to stop and get some drinks to take with us for the day. It does not take long for me to realize who is going into the store. I reach for my shorts and Ginger tells me I am to go in as I am dressed.

As I walk into the store everyone is staring and laughing at my attire. One group of girls says don’t forget the sunscreen, “we wouldn’t want the baby to burn. I quickly pay for the drinks and almost run back to the car.

We finally get tot a secluded beach and have the time of our life that day, in stark contrast, Ginger looks hot and sexy as can be in a revealing black one piece swimsuit and me in nothing but a diaper, plastic pants and T shirt. As we get out of the car, I look around to be sure no one else is at the beach and head down to the water. It is truly a beautiful spot. It seems that within minutes other couples start to show up in the bikinis and sexy one piece’s, yet I am running around like a toddler with his mommy.

It does not take long it the hot sun with me drinking all the drinks that I totally soak my diaper. Ginger refuses to change me telling me to go swim like a good boy. I go swim as instructed, but my diapers were getting heavy and start to fall down with the combination of water and pee. I try and walk back up the beach to Ginger to the laughter of all the people and my soaked droopy diaper.

We spend the rest of the day swimming and playing on the beach. With me in just diapers and plastic pants, most people now seem to be into there own vacation and pretty much just go about there own business except for the occasional remark about me being as sissy or baby.

Just before sunset, it is time to get back to the ship, as we are about to board the ship we run into Jeff and Cindy, Cindy runs up behind me pulling my shorts down exposing my diapers to everyone and tripping me in the process. They ask us to have a drink with them at Senor Frogs next to the cruise terminal. We decide to have a drink with them as Ginger tells them about our day on the beach and how much fun we had.

A short time later we go back onto the ship and get cleaned up for dinner. Ginger instructs me to put on a disposable diaper as tonight is the formal and she wants my diaper to be less obvious under my tuxedo for the pictures.

After getting dressed we go down to get our pictures taken before dinner and then off to the dining room for a great prime rib dinner. At our table we meet three other couples and realize that one of them was on the beach with us today, nothing is really said other then one of the wife’s said she really liked my swimsuit and wants to get one for her husband, he turns bright red as Ginger gives them the address to a store in Miami. After dinner we decide to go to the show in the theater. After the show we both go back to our as we are both very tired and quickly fall asleep.

The next morning we are in Labadee and get off the ship to see the local crafts and see some of the beaches. Ginger has me in a blue T-shirt diapers and blue plastic pants covered by shorts. We quickly realize that Labadee is pretty boring and go back on the ship to eat lunch and relax.

We decide to eat lunch in the windjammer cafe and then Ginger tells me she wants to go up to the pool. She tells me to stay dressed as I am and we head up onto the pool deck.

As we get up onto the deck, she tells me to take my shorts off and relax, as I can cover up with a towel. I hesitate in doing so, but quickly oblige after Ginger tell me to do it now or I will be in just diapers and no towel.

It is extremely relaxing with a slight breeze and I quickly fall asleep dreaming of all the exciting yet embarrassing times we have had of this vacation and how lucky I am to have Ginger as a wife.

A short time later I hear a lot of voices and wake up to the rest of the people getting back onto the ship. It is only after I get quite a few stares and people laughing at me that I realize my towel is gone as well as Ginger. As I get up to leave I see Ginger and Cindy walking my way.

Cindy walks over to me and pushes me back into the chair telling me we are going to stay here and have a few drinks until we leave the port. By now most the people are back on the ship and keep walking by and staring at my babyish attire. I ask both of the girls if one of them will get me a towel. Both of them just laugh at me as they grab my hand wanting to go swimming in the adult pool

As we get into the pool the college girls we met getting on the ship the first day, see us and swim over to us. Both of the girls just look at me and laugh telling me to stay in the shallow end of the pool like a good baby.

A short time later a female swimming pool attendant comes over to us and tells Ginger that I am not allowed in the adult pool with diapers on and we will have to go to the kiddie pool if we want to swim. Ginger decides it is time to go back to room and get ready for dinner. As I get out of the pool, my diaper is so heavy from all the water that it is drooping down my legs and about to fall off. Cindy walks up behind me and smacks me hard on the butt much to the amusement of all the other people in the area. I quickly try and run back to our room hoping not to be seen by anyone else.

Once we were back to our room, Ginger tells me to take a quick shower and then diapers me in a disposable diaper and yellow nursery print plastic pants for the night. She allows me to wear my Dockers and a polo shirt over the diapers to dinner, but insists that I wear my low healed black patent leather Mary Jane’s and white lace ankle socks. We go down to dinner, but no one seems to notice my shoes or socks as my long pants are hiding most of them.

After a great dinner, ginger tell me we are going to a show and meeting Cindy and Jeff. We get down to the theater and finally find the two of them.

The show is a more adult show where men have to do somewhat of a scavenger hunt and get as many items as they can from different women. The Cruise Director is the MC of the show is looking for volunteers as both Ginger and Cindy raise there hands and point to me.

The Cruise Director points to me as well as well as five other men from the audience. He lay out the rules for the contest and says each one of us has to get a bra from any women in the audience, a pair of earrings, and lipstick. Sounds easy enough to me, but then he says we have to wear it all. I try to back out but am not allowed.

The Cruise Director then instructs all of us to roll our pants legs up and prepare to find the items mentioned. As I roll my pants up, I quickly realize why Ginger wanted me to wear the Mary Jane shoes and lace ankle sock.

Various people in the audience see my shoes and sock and start to point them out to everyone, about that time all the women are laughing and yelling for the sissy boy. It seems everyone wants to help me with there different items and call me over to them. It seems this contest goes on every time the ship sales and women bring extra items just for the contest.

A couple of girls in there late 20’s yell for me to come over to them. They tell me they have the earrings for me. I sit down with them for a minute so they can fit the large pink hoop earrings. I forget about my little gold pacifier earrings I already have in my ears. When they see this they start laughing at me and tell me I need more grown up earrings,

I get up and try and leave and one of the girls grabs me by the belt of my pants. It is at this time that one of the girls notices the waistband of my pink plastic pants and yells loud enough for everyone to here “this guy or sissy is wearing diapers and baby pants. I hear Ginger and Cindy yell to the top of there lungs “show us your baby pants sissy boy”. The other ladies quickly undue my belt and drop my pants to the floor. I trip on my pants trying to get away and end up on the floor with my diapers fully exposed.

A moment later another group of ladies grab me and remove my polo shirt and straps a large pink lace and satin bra on me. Here I now in nothing but a diaper and pink plastic pants and bra and shiny Mary Jane’s.

The crowd is now roaring and laughing at my embarrassing predicament. The final insult is when the college girls from the first day grab my by the waistband of my plastic pants and start to put bright pink lipstick on me. They quickly follow this with mascara and blush.

I am told by the Cruise Director to run back up to the stage, as I am the winner. The five other guys are not even done yet, so I have to wait up there dressed like a complete sissy. I look over at Ginger, Cindy and Jeff and see big smiles on there face. I am announced the winner and get a tiara and pink sash with the words CRUISE BABE to wear for the night much to my embarrassment and the enjoyment of everyone else. I look around the stage for my pants and shirt, which are not to be found anywhere. After an embarrassing walk back to our room with Ginger holding my hand to prevent me from running, Ginger I and I retire to the room for the night and a much deserved round of exciting sex.

The rest of the cruise is pretty much the same from day to day with lots of exciting yet embarrassing moments from exposed diapers and dresses, except for the last. I think ginger decided to pull out all the stops on this day.