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malefemale I lost a bet and have to choose a punishment


Crossdressing or diapers  

39 members have voted

  1. 1. Option 1 or 2?



Question

I lost a bet and as a punishment, I will have to ask my friend's permission for everything while we will be on vacation abroad. Basically he will own my ass for 10 days. Nothing you can help here.

But I have a dilema. He gave me a choice what I want to wear and I can't decide what is better or worse:

  1. I'll have to present myself as a woman for all 10 days of vacation, no matter of circumstances or time of day. I'm not even allowed to take any male clothes or shoes with me and all female clothes I will take, have to be really feminine, not unisex stuff. Even pants and shoes have to be obviously female. Not really bad, because i like going out crossdressed and wearing nice clothes, but this has some downsides. I will have no male clothes for emergency and I will have to go on the plane crossdressed. I always get nervous when I have to show my ID when crossdressed and people can see my real identity. And when I get nervous, my bladder always switches in to high gear.
  2. I can wear male or female clothes and shoes by my choice, but pants have to be from thin fabric and tight. Basically only women's pants are an option. I'm not allowed to wear makeup and wig. Another twist to the story is, that I will have to wear adult pullup diaper under my pants all the time (it has to be obvious to anyone looking, that I'm wearing a diaper). I don't know, but I'm also afraid I will have to use diapers for its intended purpose even during the day. When I asked, he didn't want to say yes or no.


First option also probably means I will have, more often than not, limited access to the bathroom, because he knows about my weaknesses and will enjoy controlling my bladder. I don't think he will make me wet myself regularly, but might do it occasionally, just to humiliation me. Because I like omo and I'm no stranger to wetting accidents in public, that is not too bad, even when I get humiliated a bit more than I like. We will be abroad and possibility that I stumble on someone I know, is highly unlikely. Makeup, wig and big sunglasses will also shield my face from any random photos someone might take.

Second option; I can wear male clothes and I have some pretty unisex looking female pants that I can use, but downside is obvious humiliation when everyone can spot diapers and I can't hide my face behind makeup and wig. I also don't know if I will have to use diapers for its intended purpose during the day.

What do you think? What would you choose in my place and why?

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Since majority of you voted for diapers, even I was hoping you will vote for crossdressing, I'll take your advice. I'm a bit nervous now. Until now I was only wearing diapers during the night when sleeping and a few times on the plane, but had male jeans over them, so they didn't show. Now I will have to wear tight women's pants from thin fabric and everyone could see I'm wearing diaper.

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In the morning I told my friend what I decided and he told me what I was afraid of all along. Diapers would be my only "toilet" while we are on the vacation and I'm allowed to change them 4 times per day. I have to pee approximately every 2 hours. Just do the math and you can guess what that means. And I will have to drink at least a recommended dose of water per day (2.5 litres per day).

I have one "free pass" per day to use a toilet to do no.2. 

I will have to wear pullups like these.

image.thumb.jpeg.baa6c59a917c25e878bba16f34da2566.jpeg

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9 hours ago, John_John said:

We may have steered you wrong with this one

Well, it was my decision at the end and I will have to live with it. He also told me to take with me on vacation women's sandals with flat soles and red nail polish, but he didn't want to tell me more. I have a feeling I will have to wear that too at one point.

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Posted (edited)

I'm back from vacation and I was under strict control for 10 days. I couldn't do anything without asking for permission and was often denied too. It was fun, but also very stressful. My friend planned this to every detail to make me live by his strict and often strange rules and demands. I won't bother you with other rules and things I had to do, I will just describe omo and crossdressing part.

I was not allowed to refuse anything he demanded of me, but I could ask him not to do it.  If he agreed to changes or not, I automatically received extra punishment for that. He could change basic rules as he pleased, no matter what he said when I agreed to this type of vacation and rules of engagement. And he used that privilege with abundance. Basically first of his demands was change or rule about rules. I could only say yes. As additional punishments for disobedience, I had to agree to wearing diapers 24/7 for the whole weekend and pee in them too, same as on vacation. One weekend for each disobedience.

Dressing options I had on vacation were very limited and rules strict. Beside what I already described above, I got some extra rules and items I had to wear and learned about that only when already packing for vacation. 

I planned to take 3 pairs of shoes with me. 2 pairs of sandals and 1 pair of sneakers. When I was filling up my suitcases, he took out of my shoe closet 4 pairs of women's shoes and said I have to put them in my suitcase. He took away one pair of sandals I prepared and put them back in the closet.  At that point I already knew I will be wearing women's sandals at some point, but he didn't reveal any details, keeping me nervous what will happen.

First morning, when we departed and had to fly to the destination, he told me to wear sneakers, shirt and shorts. I was happy with his choice. It was stressful enough wearing diapers on the plane.

But my luck run out when we landed and get our language back. We didn't even get out of the airport yet, when he introduced the dice and told me to roll it. It was number 6. At that point he revealed "the shoe rules". What I will be wearing for the day, was decided by the dice every morning, before going to a breakfast. First "morning" just started a bit later, I guess. I had to take out of my suitcase women's sandals and put them on. Now I was wearing light blue long shorts (just above the knees), white shirt with short sleeves, wet diaper (I peed in it twice already) and black gladiator platform sandals. I was actually lucky to hit number 6. They look much less feminine than other women's shoes I had in my suitcase. I also had to go to the bathroom and painted my toe nails red. Every time I went to a bathroom, I had to turn on my phone camera, so he could watch what I was doing. Of course no peeing in the toilet. It's really strange feeling, when you are in a stall, desperate to pee and you are not allowed to pee in the toilet.

These are numbers given by dice in following mornings:
3,4,2,5,5,3,4,4,6


1. man's black sandals + clear coat nail polish
2. man's white sneakers
3. women's glittering pink sandals + pink nail polish
4. woman's purple sandals with 7 cm block heels + red nail polish
5. women's silver summer shoes with 1,5 cm block heel and glittering bows in front and glittering ribbons at the back (very feminine looking, closed toes)
6. women's black gladiator platform sandals, 3 cm flat sole + red nail polish

As with shoes, my clothes should also be man's clothes by initial agreement. But in my closet or in shops we visited prior to vacation, I couldn't find man's tight pants from thin material that he considered appropriate, so I had to wear women's pants. I think that was his plan all along anyway. Only male clothes I could wear, were male T-shirts and short sleeve shirts and a jacket I took with me just in case of bad weather. I also took with me large women's unisex purse to put in second diaper and other stuff I had to have to clean myself when changing diapers. It was decided I will take on vacation 10 pants, one for each day. He picked 7 shorts (2x white, dark blue, light blue, yellow, red and pink) and 2 long pants (white, light blue). On the first day I was wearing light blue long shorts. Length of the shorts I had in my suitcase varied from really short that more often than not revealed edges of diapers when I was in any position other than standing, up to long shorts. Long pants were ankle length type of pants. It was not my decision and pick anyway, but I also thought 10 pants should be enough to wear clean pants every day. I already knew sooner or later diapers will leak with amount of water I will have to drink and fact, that I will be limited only to 5 diapers per day, but I was still optimistic. Of course, even good plans can go wrong. Why would be this time any different. Already on the first day we realised, that I will have to change pants before the day is over. I had to wear one pants during the day, another in the evening. I leaked too often to be able to keep my pants clean enough to go to dinner in them. He didn't want me to smell bad and wearing pee stained pants at dinner or after dinner when going out for a drink or two. I also had to use a lot of parfume to cover pee smell in summer heat. If he wouldn't be embarrassed by that, I doubt he would let me change pants or use parfume, just to embarrass me. Lucky me. After every 3 days I had to pay for laundry at the hotel to wash my pee stained pants, so I was able to wear them again. I just wonder what laundry service personnel was thinking when they saw all pee stained pants. I would rather buy more pants, but I was not allowed to and had to use laundry servise at the hotel.

 

As my friend planned, diapers are visible when you're wearing thin and tight pants. It just depends how much. Someone said that most people won't even notice diapers. Maybe they wouldn't, if I was wearing normal male clothes, but because I was dressed as I was, people looked at me and than also noticed that I was wearing diapers. I heard a few remarks when they were talking among them self. None of them were flattering.

As with all other rules, diaper rules also changed before we left home. I bought enough diapers for all 10 days, but when he was supervising what I was putting in my suitcases, he told me that we will not take so much diapers with us and I will have to buy them every day for next day. First day when I was looking for a store that sells adult diapers, he also told me that I will not be allowed to buy them at the same store or wear same brand/model of diaper more than once. If I can't find a new store and brand/model of diapers every day, i will just have to buy panties and pee in my pants for the day. Luckily I was able to find different store for each day. Because I had to wear various models, some were less, some more bulky or absorbent, I never knew how long it will take before they will start leaking and how much they will show through or from under my pants, until I put them on and used them. Luckily I was able to persuade him to let me change diapers 5 times per day, instead of only 4, because of this new rule. I was also not allowed to change diaper before at least 3 hours past from last change. And I had to get permission from him as well. I usually have to pee every 2 hours and even more frequently after meals. With so much liquid I had to consume every day, I peed even more frequently. I had to take one extra punishment for this change of rules too.

I'm not new to diaper wearing by any means, I wear diapers for sleeping for a few years now and I'm used to that, but I must say that wearing them all day is a different story. It's a strange feeling, walking around diapered and pee in them when awake. Because I have to pee so often and had to drink a lot, they were also wet most of the time. In general, diapers are pretty absorbent and made to be comfortable even when wet, but you still feel the difference. And than comes a problem of leaking when they were too wet. Every time I peed, especially second or third time, before I could change diapers, I was nervous because of that. I was also not allowed to take with me spare pants and had to wear wet pants until they dried out in hot weather.

On the plus side, it was definitely strange, but good feeling that I could pee whenever I felt the need and didn't have to hold it really hard, like i usually do when not near the bathroom. I got used to that quickly. It took a bit of adjustment time when I got back home and was without diaper again. First day scared me a bit, because I couldn't hold as long as before the vacation. And even before that, holding times were not something to brag about. It went from need to pee to really have to pee very quickly. Now, after few days of normality, I'm back to my old holding times, luckily.

Even in the hotel room, I was not allowed to use a bathroom to pee and have to do it in the diaper. On two occasions I peed in my diaper even before we left the hotel in the morning, such it was desperation. On most days I had to poo after breakfast and that was also the only occasion when I could pee in the toilet as well. Because of that I didn't have to pee in the diaper right away after breakfast. Night time diapers were just too wet to still wear them while going to a breakfast and change them later.  Night intervals were long and to keep me well hydrated, I also had to drink large cup of tea before sleep. To keep the bed dry, I had to put extra protection on the bed. I didn't know when diaper will leak, because I was wearing different diapers every night. I was also restrained with under the bed handcuff system every night, so I wouldn't secretly use a toilet. At least that was an excuse to do it. But this was very convenient for other purposes also, of course. I had to agree with everything and couldn't do much or get of the bed, because of the restraints. He took full advantage of that every night.

Every day I had to drink 4L of fluid (coffee, tea, soda, water). Beer or cocktails didn't count in this quota, but I also drank them in the evenings. Because of all that, my bladder was filling up all the time and I peed so often, that diapers, more often than not, started leaking before next change and at least small wet patches appeared on my pants. On one occasion I peed so much in not very absorbent diaper, that I was wet down to my knees at the end. This was also the only time he let me buy new pants and one more diaper change was allowed that afternoon. Of course, one more punishment weekend added.

When I was taking a shower, I was also not allowed to pee and was watched, so I wouldn't cheat. On one occasion I came out of the shower so desperate, that I had to pee right after I put on new diaper. Even when I was changing diapers in public bathrooms, I had to allow him watch me through camera on my phone, so I wouldn't use a toilet. Every time I wanted to use a shower, I received a golden shower first, while kneeling in the shower.

As I mentioned before, luckily I had one "free pass" per day to use a toilet to poo. It would be really bad, if I would have to poo in a diaper. But already on the first day, I had to poo twice. First, he said no, do it in the diapers, but after lots of begging, he let me use a toilet for the second time. Of course, I got punishment for that. Twice in 10 days that happened.

One of more interesting things that happen, was when he put itching powder on my diaper, before I put it on (I didn't know that). It was not the first time he helped me getting dressed, so at that time, I didn't think much of it. I just assumed he wants to touch me while doing that. It was not the first time he helped me get dressed and touched me intimately while doing that. 

It didn't take long for itching powder to take effect. Soon after we left the room, itching started. It was more and more intense minute after minute. I started to panic and told him it's something wrong with me and I need to see a doctor. He calmly said it's just itching powder and it's normal reaction. I was stunned. I didn't expect that. Now I knew what is wrong, but I was going crazy from itching already while we were in a taxi and on the way to the restaurant. I tried to scratch myself through pants as gracefully as possible, but it didn't do much good and soon he told me to stop doing that, because it doesn't look good. Asking him to return to the hotel was out of the question. He done this with a reason and wouldn't go back so soon. During the dinner it was even worse, because I was not allowed to scratch myself or even touch myself below my waist. I wanted to go, but he demanded of me to finish the dinner and also coffee and desert. I had tears in my eyes from time to time, so much it itched. I peed in my diaper twice on purpose just to stop itching, but didn't help much. After I finished my main meal, he allowed me to visit the bathroom and scratch myself under the diaper and try to clean myself with wet tissues, but I was not allowed to remove the diaper. It helped a little, but not as much as I hoped. When we came out of the restaurant and behind the corner, I took a bottle of water out of my bag and just poured it down my diaper. I got another weekend punishment for that, because i didn't ask for permission, but I didn't care. I didn't want to risk him saying no and than I couldn't do it  (if he said no and I would still do it, he could choose whatever punishment he saw fit to punish me after that). It was a bit better again, because of wetness, but still itched as hell, because powder was on a diaper and water didn't wash it away. I just had very wet diaper after that and pants also, because diaper couldn't handle so much water at once and was a bit loose already from all things I done so far, so water just went down my legs. Because pants were so wet, we couldn't go anywhere else, except back to the hotel. We walked about 30 minutes. He demanded of me to walk gracefully while wearing heels and not touching myself around the crotch all the time. It was hard. I couldn't walk straight, let alone gracefully because of all the itching all over my crotch and ass. When we arrived back to the room, I was finally allowed to take off a diaper, get in a shower and clean myself properly. When I came out, he also applied a special cream on my skin. No more Itching, finally. I was still upset, but happy that itching finally stopped. It was the first time I tried itching powder and now I know that videos of pranks are not fake. it really itches like hell. 

 

I don't want to describe every day in details, because it would be to long and no one would want to read all that, but you can ask questions, if you want to know more and think I forgot to mention something important.

Omo situation was more or less the same every day. Lots of drinking and peeing, embarrassing moments when people noticed diapers, wet pants or actual leak when I was peeing and pee escaped from a diaper.

Beside usual turist destinations, we visited lots of stores where I had to try on high heels or dresses, makeup, ask for assistance while looking for women's clothes or shoes and want to try them, even visited erotic shop and bought some toys etc. I also bought a few shoes, dresses and some underwear, but didn't wear them on vacation.

On the forth day, when dice decided that I will wear sneakers, he decided I should also wear black 7den pantyhose, red lipstick and red nail polish on my hands, otherwise I would look too manly and white. "That's just wrong" were his words. I was wearing white shorts and shirt on that day. 

Sometimes I had to go to a random store and ask, if they have bathroom for customers, when I already had wet pants from leaking. He always picked stores that didn't have bathrooms for customers and I only ended up in embarrassing conversation why I need a bathroom urgently. For encouragement to really try hard, he told me, if I can convince them to let me use the bathroom, I should go in and can pee in the toilet and change diaper (1 extra change that day). And of multiple tries every day, only once I was allowed to use employees bathroom and couldn't even change a diaper, because I already used spare one from my bag during the day. But at least I peed in the toilet.

I also had to ask cashiers in various supermarkets, if they know where I can buy adult diapers, because I couldn't find them in their shop and I really need them. Sometimes they didn't know if their shop sells them and called another person from department that sells diapers for kids, to tell me if they have adult diapers or not. These were basically just tasks to embarrass myself. Often multiple people, including customers heard that I'm wearing diapers and need to buy them.

I must say this was strangest vacation I had so far. Now I will also have to serve my punishments for next 6 weekends. I just hope I won't stumble on people from work or some relatives when wearing diapers. it would be really embarrassing and I would have some explaining to do. At least many of them are on vacations, so it's less chance for that as would be normally. I will be using diapers I bought for vacation in the first place. Friend won't be with me all the time, but he will lock a belt on my pants with phone operated lock. I will have to call him and ask him to unlock my pants when I will need diaper change or poo. I will be allowed to crossdress, because hiding my identity behind make up and wig is much more important at home than it was on vacation in a foreign country far away from home. When he will be present and we will go out, I will be wearing a dress or skirt, so other friends won't notice diapers, if I'm lucky. He enjoys embarrassing me, but he knows where are limits not to compromise my future with his games. At least I hope so.

Edited by CarmenCD (see edit history)
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I guess eventually had to happen. I was lucky until now. I got caught by coworker and his wife while I was wearing diapers, white women's pants, pink blouse and pink high heels this weekend. When I notice him, I got so nervous I lost it again and peed in already wet diaper so much, that it started leaking and even made wet patch on my pants. I'm not sure, if they spotted that, because wet patch was not very big yet, but still worst moment possible for a leak. Couple behind me definitely spotted that, because I heard woman pointing out that to her man. To make matter worse, coworker and his wife saw me in well lit supermarket when I was waiting in the line at the cashier and couldn't go anywhere. I was wearing a wig, makeup and glasses, but I still think he recognised me. They were in a separate line, a bit behind me, but close enough to see everything. Whenever I tried to look back to see what they were doing, he was looking at me. But he didn't wave or do something else to draw my attention. He is not at work right now, because he is on vacation, but I don't know what to do when he returns? Should I say something or just pretend nothing happened and hope he will do the same? Possibility that he didn't recognise me is slim, but also possible. Maybe they were just looking at a "crossdresser in diapers", because they had nothing better to do while waiting. I also don't know, if they saw my car on the parking lot or not.

What do you think I should do?

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