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Views: 2817 Created: 2015.06.06 Updated: 2015.06.06

Caribbean Cruise In Diapers and Dresses

Part 1

My greatest humiliation as a big sissy baby was when I saw my wife Ginger at our home computer with the history file of the browser open, and a credit card bill at her side along with her hairbrush -- her expression darkening with every new URL... Hubbies.com, Adultbabysource.com, Sissify.com, Sissymaids.com Sissysitter.com, Humiliatrix.com... Then the furious swat of Ginger's hairbrush against my upturned bottom, my legs flailing, my sobs, my promises to straighten out, my welted panty bottom, and Ginger's red-nailed finger-in-the-face warning to me: "stop the nonsense and be a man, or I will put you in a diaper and treat you the way you act like a baby."

Don’t get me wrong, she is an amazing woman that has recently lost quite a few pounds, and looks better now then the day I married her. After finding my secret WebPages she started to buy sexy leather and PVC outfit for herself that just drive me crazy and literally bring out the dominatrix in her. At the same time she ordered me sissy baby girl dresses, rompers, French maid dresses, diapers and baby plastic pants.

More recently, it is not uncommon for her to have me dressed as a baby complete with diapers and plastic pants or even a little sissy sailor dress or one of the many sissy party dresses she just bought. At other times, she will have me dressed completely in a PVC or leather French or English Maid still with diapers and plastic pants embarrassingly visible underneath the short dress. She loves to embarrass me when I am dressed like this regardless of who is around and might see me.

My wife and I recently planned our summer vacation, this year we were going on a cruise in the Caribbean and she promised that it would be more exciting then past vacations. We would also be spending a day in Miami Beach, Florida before leaving on the cruise and then a couple of days in Coca Beach, Florida after.

About two weeks prior to leaving on the cruise, my wife removed all the hair from my whole body; she said she did not want any hair on me during the vacation except that on my head, reminding me that babies and sissies do not have body hair.

Just prior to leaving on vacation, she laid out a strict and embarrassing plan for me to follow. I knew I was in for an interesting week when she told me as we packed that I was not going to be allowed to bring any underwear at all.

So she packed lots of diapers, both cloth and disposables, and most of my best plastic pants (including some of my little girl ones, which I hoped she would make me wear only in private). For the whole week I would have to wear diapers. At all times during the vacation, I was diapered. My toilet privileges were totally revoked except for messing and for that, I had to ask permission. I was never allowed to pleasure myself. (If that got done it was up to her.)

The day we left for vacation, we had to fly to Miami. That morning my wife woke me up real early she first removed my plastic pants and then unpinned my soggy wet diaper. With disgust, she asked me “Are you ever going to stop wetting like a baby?" Without waiting for an answer she took me to the bathroom and sat me on the toilet. When I was done she told me to get in the shower. I took a long hot shower washing my hair and body with baby shampoo and soap. When I got out of the shower there was a thick cloth diaper and pink nursery print plastic pant lying on the bed. I also noticed a pale blue polo shirt and thought nothing of it.

My wife massaged baby oil all over my body followed by baby powder, the smell of baby powder alone embarrasses me. Next she expertly diapered me in one of the thickest cloth diapers I have ever seen followed by the pink nursery print baby pants. She pulled the polo shirt over my head and had me stand up. The diaper was so thick I had a hard time standing much less walking.

I told her the joke was over and to give me my normal underwear back. I quickly found out that all my underwear had been thrown away. She next handed me a denim shortall with Winnie the Pooh on it and snaps in the crotch. She assisted me in putting on the short all which did nothing to hide the fact that I was heavily diapered.

It was a beautiful summer morning and everyone was outside working in there yards. I told her there was no way I was leaving the house dressed like this. She quickly responded and smacked me in the face. I begged her not to take me out like this. She quickly dragged me out of the house to the car, as we walked to the car, everyone turned and stared at my outfit, one of the neighbor women Deana came running across the street and told my wife that she was glad to see that she finally put me in my place. She then patted me on my thickly diapered butt while telling me to have a great vacation and behave for mommy. I wonder how many people know about my diapers and dressing up.

Ginger led me to the backseat of her sport utility vehicle and opened the door for me. "C'mon, scoot!" Ginger said, pointing to the backseat, she buckled me in like I was a child. I looked at myself, my childish overalls, and ankle socks and obviously diapered bulging bottom. I cringed. "Ginger please, you have more than made your point already. Please don't make me go through with this."

I was glad to get to the airport, but than had to endure the embarrassment all over again. When we checked our luggage something in my suitcase alerted security. The young security girl asked if it was my suitcase, when I told her it was. She said she would have to open the suitcase and inspect the contents. I about died of embarrassment when she opened the suitcase and she found nothing but diaper, plastic pants, baby dresses and rompers, but worse of all was the butt plug that fell on to the floor. During the inspection she just smiled at me. Once she finished inspecting she said we could go now. As we walked away I could here her and the other security girls giggling and commenting on what a sissy I must be.

We went through security at the airline gate, which I thought nothing of until my diaper pins set off the metal detector. Another security person had me raise my arms as she traced the metal detector wand over my body. It kept going off every time she would pass it by my diaper. She asked if I had change in my pockets. Ginger told her “no, it was my diaper pins”. She told me to take the pins out of my pockets. I did not know what to say, Ginger spoke up and said “I couldn’t and that I was wearing them with my diaper and plastic pants”. The girl just snickered and said I could go.

We finally got on the plane. I was already soaked by the time we reached Miami, but she made me stay in the wet diaper until we got to our hotel. Thank goodness I didn't poop, because I think she would have made me sit in it.

When we had unpacked, she finally changed me, and then she said that it was time to go to the beach. It occurred to me that I had not seen my bathing suits come out of the suitcase, so I asked her where they were. "Nowhere," she said. "You're in diapers for the whole week, and that includes the beach." I couldn't believe it. She actually was going to make me wear diapers and plastic pants on the beach. I begged her, but she doesn't back down, and I found myself pinned into new diapers with my pink nursery print plastic pants before she let me pull on some shorts and a t-shirt. I looked in the mirror, and I didn't think that it was even possible for anyone not to know. My rear end stuck out so far it looked deformed, and the t-shirt wasn't long enough to cover anything.

On the beach, we set up our stuff and I decided just to lie down on the blanket so that there was some hope that no one would notice. But Ginger wanted to go swimming, and she said that she didn't want to leave her baby alone with all these strangers, so I needed to come too. She made me take off the shorts and the shirt, leaving me in the middle of all of those Speedos and bikinis in bulgy pink plastic pants that clearly were covering something else. I started to cry, but she told me that if I didn't stop she would make me suck on my pacifier too, and she pulled it out of the diaper bag (which I didn't like her bringing along) as a threat.

We went down to the water, Ginger holding my hand. Only a few people stared. I guess most of them were too wrapped up in their own vacations to notice mine. But there were a few college girls on the beach, and they made fun of me as we passed them. One of them called me a big baby and the others all laughed. She said not to take notice and led me to the water, where I could let the waves cover up what she wouldn't let me cover up any other way.

Of course I wet myself in the water, but my diaper was soaked anyway from the waves. We stayed for quite a while until she told me it was time to leave. It was almost sunset in Biscayne Bay, and sunset is almost a religious experience here, Ginger made me lie on the blanket so she could change my diaper. I told her it was OK, that I could do without a change, but she wouldn't hear of it. As she unpinned the old soggy diaper and pulled a clean one under me and pushed my pacifier into my mouth and went back to work pinning the diaper on me, and pulled up my new plastic pants, which were blue ones and I couldn't help crying when I saw that. When the change was finished, Ginger let me put my shirt back on but she wouldn't allow me to put on my shorts. We packed up our stuff and headed for a bar near the beach to get a couple of rumrunners and watch the sunset. As we waited in line for the drinks, though, I felt myself cramping. I told Ginger, and I begged her to let me find a toilet (she makes me say "potty" which always embarrasses me), but she refused. She told me to stand over at the edge of the beach and wait for her, and told me to hold it. But I couldn't hold it, and soon I was standing with a large group of people watching the sunset, drinking a rum runner, at least she didn't make me drink from a bottle, with a full load in my diaper which was in plain view of anyone who happened to look down, which a lot of them did when the smell hit them. She held my hand and walked me back to the blanket. The beach was much less crowded now, but the girls were still there, and they shot taunting looks at me as we passed them.

Back at the hotel, Ginger changed me out of my messy diaper and put me in blue nursery print plastic pants she covered the diaper with a pair of short shorts, that did nothing to hide the diaper and pulled a T shirt over my head. She then decided to go to our favorite fetish wear store in Miami and pick up some new clothes. We took a taxi for short ride to this delightful store.

The sales girls in the shop were different from our last visit… not surprising considering the time between visits…but just as friendly and unsolicitious as the others. We browsed around to see what was where and then found myself fascinated by the big baby dresses and PVC French maid dress hanging in one corner. I could not ignore the attraction. Then I wandered over to the bondage section…I always wanted to be restrained and forced to wear and use my diapers but who would do such a thing to (for) me and how would I ever tell them I wanted it? The handcuffs always caught my eye. This was because they were an easy way to lock yourself up and I like the finality of their solid hold on my wrists and ankles. Periodically one of the sales girls would ask if we were "ok" or if we needed any assistance. After this one girl asked us a second time we decided it was time to purchase the diapers and plastic panties we came for. Besides the bulk between my legs was making me feel very self-conscious and I was sure I'd be `found out'. Silly when you think of what I was there to buy. Anyway I asked the salesgirl where the plastic panties were and if they still carried the cloth diapers. She led me to a series of drawers and said her name was Cathy and I should ask for her if I needed more help.

I chose 6 large cloth diapers that would fold and be very absorbent and bulky when I used them. Next came two drawers filled with various colors, sizes and styles of plastic panties. I started to select several and then began to have doubts about their fit since the sizes were numbered instead of the `extra-large' markings on the ones I had at home, and were presently wearing. Seeing my indecision Cathy again offered to help and I confessed I wasn't sure of the size. She asked the size of the person they were for. Simple enough question but I fear I blushed a bit. After starting several answers I admitted they were for me. She smiled so very understandingly, glanced at my padded hips and said, "I thought they might be. Ginger and Cathy laughed and started talking with each other. You can always try them on." That seemed logical enough and I headed for the changing area with 5 different pairs. As I was about to enter the changing room I noticed an all plastic onsie, something else I'd never considered but quickly asked if I could try that on too. She reached two down and handed them to me as I slipped through the curtain.

Several of the panties fit well, even over my double diapers, and I quickly made my decisions. A quick glance at my watch told me I was not there as long as I thought so I took a deep breath and stepped into the onsie and reached behind me to pull up the zipper. I could only get it about a third of the way up and was about to abandon the experience when I heard Cathy's voice ask how things were going. My quick answer was," fine…" and before I realized what I was saying, "…but I can't reach the zipper." Somewhat to my surprise and embarrassment (and deep down delight) Cathy glided through the curtain and said, "turn around". This was the first time anyone had ever seen me in my diapers and oh, wow was my head hot and swimming. She zipped me in and inquired "how's that?" All I could stammer was "thanks" and she patted my diapered butt was gone. I spent a little time looking at myself in the mirror and deciding to add the onsie to my purchases and then realized that I needed to ask Cathy to undo the zipper for me. But where was she. I looked out through the curtain for Cathy or my wife and the other girl was talking on the phone but no Cathy or Ginger. The other girl caught my eye, smiled and pointed to a door. After an awkward moment I caught on that she expected me to walk out in only my diapers and plastic onsie and go get Cathy. Ah, why not. I took a quick breath and crossed the room to the indicated door, looked in and almost pleaded with Cathy to come help me.

On our way across the room I again took a quick look at the adult baby and maid dresses. I didn't think she noticed but said, "pretty aren't they. Want to try a couple on?" Just how hot can one's neck get but I nodded yes and muttered "sure". She took several off the rack and with that innocent smile said we should try a couple different styles. Suddenly here I was in the changing room with this petite pretty girl pulling a baby dresses down over my diapers. The dresses did nothing to hide my thick bulging diapers. Was this ecstasy or total embarrassment? The last dress was also the prettiest, made of pale yellow organza and taffeta with a peter pan collar, the fullest skirt and just dripping with ruffles and lace, she lifted the last dress over my head and zipped it up, she quickly left the dressing room as fast as she came in. She returned in a few minutes with a full crinoline and slid it up my legs, we both laughed, as she had to force past my bulging diapers.

I was in heaven and started twirling around as she returned with one of the shortest black PVC French maid dresses with white PVC ruffles in the back. She asked if I wanted to grow up and be a big girl and try it on as well; I did all I could to hide my embarrassment and excitement as she slid it over my head. As she zipped it up, I heard a distinctive click and she left the dressing room leaving me in only the short French maid dress with diapers and plastic panties almost fully exposed. She returned a few minutes later with some high-heeled Mary Jane’s and cute little lacey white ankle socks. She insisted that I try them on. I quickly complied as she slipped them onto my feet and adjusted the ankle strap. She left the room one more time as I decided to put my clothes on but couldn't find them and decided they must have put them somewhere to keep them safe.

I looked outside the curtain for Cathy and only saw the other young girl. She said Cathy would be with me shortly. When she finally returned she told me that my wife had gone back to the hotel and took my clothes with her.

Cathy told me to follow her, in horror I realized the predicament I was in as both girls started to laugh. Cathy told me they were closing in a couple of hours and she would give me a ride, but I would have to help them around the store. I asked her for something else to wear and that is when she told me that my wife bought the dress and it was locked on, I quickly remembered the snap and realized it was a lock. She told me I was to greet customers at the door with a curtsy and help them any way I could.

A short time later a tall gorgeous women with a young man dressed as a little sailor boy in only a short sailor top and matching shorts walked in, it was obvious he was heavily diapered as well. She addressed me as sissy and asked for the leather and bondage gear. I led the way, she turned to her little sailor, “see you are not the only one in diaper” I turned bright red with embarrassment and curtsied for her as instructed. She looked through several item and decided on a leather collar and leash, I started to carry it to the counter as she told me that he would wear it home. You could see his embarrassment as she buckled it around his neck.

She then stuck two fingers down the front of his shorts and ultimately his diaper announcing that he was wet. I felt bad for him as she started to treat him like a child and scold him for wetting. She asked if there was a place to change his diaper. Cathy spoke up and led her to a back changing room with a tall table. To my disbelief Cathy told the lady that I could change him if she liked. She said that would be perfect, what else are maids for? She smacked me hard on my diapered bottom and says “it looks like he is already an expert with wet diapers.”

The young man was told to get up on the table, as I started to pull down his shorts the ladies all laughed and the two of us just turned red with embarrassment. He had on pink nursery print plastic pants. I asked him to lift his hips and pulled his plastic pants to his ankles. Next I unpinned his diaper and pulled it out from underneath of him. Cathy handed me a washcloth a told me to be sure to clean him up thoroughly. I was instructed to rub baby oil on him next, as I did he started to get excited, his wife then told me to masturbate him. I told her there was no way I could do that.

Cathy heard me and came across the room so fast and smacked me hard across the face. She then told me I would do as I was instructed or I would be giving him a blowjob next. I stated to masturbate him, much to the enjoyment of all the ladies. Within minutes he had a huge orgasm, I cleaned him up as instructed and finished diapering him and pulling his plastic pants up. I started to put his shorts back on and was told that will not be necessary as he will be leaving in just his diapers and shirt, as she said this she grabbed the crotch of my now soaked diaper and said I see my sissy is not the only wet baby here. She handed me a business card as she was leaving with her sissy that said “Florida Sissy Transformation” it seems she runs this business that provides adult baby and maid training for sissies like me.

Cathy said she was ready to go as well, that I had helped her enough for the day, as we walked out to her car I felt like everyone was staring at me. After all, here I am a grown man in thick diapers and plastic pant barely hidden by a very short and frilly PVC maids dress and high heels, things were about to get real bad. I was strapped into the front seat of this girl’s car that my wife and I met for the first time today. She was looking at me and shaking her head. ”You don’t remember me do you?” I looked at her and said no.

She said “well let me refresh your memory little sissy boy, you and I dated before you were married, although at that time I had no idea you were such a sissy. I thought you were a real man boy have times changed”

As we were pulling away from the store, I told her that I had to go pee; she said "You know what, if you can't hold it and keep from wetting that diaper until I get you to your wife, I'll take care of it for you, and don’t you dare wet the seat"

She pulled up and stopped the car outside a huge strip club; I asked her why we were not going back to the hotel. She said, “Your wife is here waiting for you”

I was concentrating on not peeing, I had no desire to be taken into this club and further humiliated, especially the way I was dressed in pink lipstick, wide black leather posture collar, black PVC French maid uniform complete with white apron, white PVC ruffles, white shoulder length PVC gloves, thick cloth diapers and pink nursery print plastic pants that were observable due to the shortness of the skirt, white lace ankle socks, and 5 inch black patent leather Mary Jane’s.

"This is the deal, "she was adjusting the white PVC ruffles and rolling down the skirt. "We're going in this club to meet your wife and have a little fun. If your diaper is dry in an hour, then I'll let you go pee in the bathroom like a man, well sort of considering your current state of attire."

She finished adjusting the skirt; the bottom of the diaper could just be seen. She reached up with her left hand and squeezed my cheeks against the pacifier, she pursed her lips. "But, you little sissy, If I find that you wet yourself, peed your panties, diddled in your diaper, then sissy, well let's say, things could get very sticky. When Ginger gets a hold of you, she will teach you the lesson of your life. Hopefully she will let me help me 'toilet' train you."

But I couldn't handle the thought of more people seeing me like this, I was humiliated enough. "Better get going," she said and then walked up to me, patted my ass and took my hand dragging me into the club. “You better hold it, I've given you fair warning and a fair chance, and I can't be fairer than that, can I?"

As she said that I felt my bladder filling my diaper, the pee straining to get through my cock, past the plastic pants restraining it. My head spun and I started to panic with the implications of wetting the diaper.

I moaned into the pacifier, she looked at me and smiled. She knew, she knew everything and didn't have to say a word. I knew too. The further events of the day had just taken a turn, probably for the worse for me.

A couple of tears started coming down my cheeks, rolling gently and easily over the pacifier as we walked into the club, I was totally humiliated, here I am dressed as a sissy in a short maids dress, diapers and plastic pants and the rest of the club is filled with a bunch of rough looking me and all these good looking women in nothing but skimpy strip outfits and sexy high heels.

Cathy yells across the club to Ginger as everyone turns and looks at me, I get a few quick whistles and then responses like who’s the sissy? I am led over to a table, where Ginger lifts my skirt shamefully revealing my diapers and plastic pants in front of everyone. She quickly discovers my wet diapers and proceeds to put me across the table and spanking me until I am in tears. She decides that I will remain in the soaked diapers until we get back to the hotel.

Next think I know my wife buys me a table dance from the two best-looking girls in the club. One of the girls is about 6 foot tall and stripping out of a PVC bodysuit. Neither of the girls will even look at me except to laugh at my attire. They are both grinding against me and pinching my tits. I start to rub my cock in all the excitement of these girls with my wife. One of the girls notices and smacks my hand away hitting me in the balls and causing me to pee further soaking my diaper and causing it to leak onto the floor.

Ginger looks at the puddle on the floor and says “you’ve done it now, she gets up in anger and grabs my hand dragging me out of the club, we hail a cab and take the short ride back to the hotel, on the way to the hotel, Ginger asks me “ What did you think of Veronica,” I ask “who is that”, Ginger responds “the tall girl in black PVC, she thinks you’re cute, for a sissy boy” I can only say “ she is sexy” once in the hotel lobby the girl at the front desk looks at Ginger and say “I see you will still need the crib for the night” Ginger responds to the girl “ If he wants to act like a baby I will treat him like one” She drags me up to the room and makes me take a shower. Once I am done, I am diapered into two of the diapers we bought earlier that day complete with yellow plastic pants, next she slides the fullest crinoline I have ever seen over my head and then takes the pale lemon yellow dress I tried on earlier and slides it over my head, after tying the sash in a big bow, she instructs me to sit down. She slides saddle shoes on my feet and ties them in a cute bow. She tells me to stand up and look in the mirror, looking back is the biggest sissy I have ever seen.

Ginger looks at her watch and says we had better hurry; you will be late for your appointment. She pushes me out of the room and into the elevator. When we get into the lobby, the same front desk girls comment on how cute I look. Ginger drags me into the hotels beauty shop as the girl sitting at the counter says this must be Sissy Davey or is it Mandy. All the ladies just stare and whisper to themselves, one speaks up and says that more men should be treated like the big babies they are.

A girl no more then 25 walks up to Ginger and introduces herself as Samantha, she does not even acknowledge that I am standing there as well. Ginger explains that she wants complete makeup fit for a sissy; she also explains that she wants nothing done to my hair; she wants everyone to know that I am a man or sissy as she puts it. Samantha tells her the sissy will be fine and should be done in about an hour.

Samantha leads me over to a chair gives me a stern look and say, “well sit down sissy,” the other women just giggle at my predicament. She then takes a large pink cape and says; “We can not take a chance at ruining your sweet little dress, can we sissy” She wraps it around my neck and snaps it in the back. She then try to straighten it out and cover my dress, but do to the thick crinolines it just barely covers the dress. She starts with a light foundation on my face followed by a pale pink eyeshadow and eyeliner. She then proceeds to curl my eyelashes while commenting on what long eyelashes I have for a man or should I say sissy in your attire. Next is the mascara and a dusting of blush on my cheeks, she stands back to take a look and says almost finished. After rummaging through the lipstick, she says “perfect, sissy pink” After applying it to my lips she calls over another girl, who walks to one side of me with a gun like contraption and before I know it pierces my ear. I tell her I cannot wear earrings to work just as she puts one in the other ear.

They both announce all done and take the cape off. As I stand up I am lead over to a full-length mirror, “well Samantha says what you think?” In utter horror looking back at me is a sweet looking sissy, but still obviously a man. It is then I notice my earrings are little gold pacifiers; it is then that Samantha tells me that the backs are clamped on and I will have to return in a week to have them removed and normal earring put in. Before I am allowed to leave, Samantha tells me to twirl around, as I do it is then that one of the girl’s notices and announces “he’s wearing diapers and plastic baby pants” Samantha lifts of the full skirt of my dress to show everyone my embarrassing diapers and plastic pants. A couple of girls say, “I got to get pictures of this; I want to show my husband what happens to men that act like babies.”

I am finally allowed to leave and head back to the room and have to pass by the front desk again; the young girl giggles in excitement and asks me to come over to her. As I do, she tells me to turn around and puts a small pink necklace of hearts around my neck, she then pats me on my diapered bottom and tells me “go see mommy”


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