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So, for work, I am being put on the night shift for the next little while. And since I won't have to worry about too much social interaction at work, as there are only 2-3 people I'll need to deal with, I am looking for small ways I can be more sissy, since more things are likely to go unnoticed. Here are some of the things I am hoping I can get away with, and am planning on doing, but some of them are still iffy. I would like other suggestions as to small things I can do and likely get away with.

-I am going to be shaving my body (I have shaved everything but my arms before, but I'm going for it)

-I am going to wear my chastity cage more (pink CB2000). Sitting in a public washroom to pee during the day with high traffic makes it kind of annoying for me, but now I'm likely to be the only one in the bathroom. Plus, it tends to make a bulge in the front of my pants, which I am not as concerned with on overnights, as few people to notice.

-Since I will be wearing chastity, I'll also need to wear tight fitting panties to hold it in place. I haven't under dressed in the past really, but again, something I'm considering.

-I am contemplating wearing a diaper to work, but right now, that might be a little too much unless I can find some pretty discreet ones. For now, it is a maybe.

-Also considering wearing a butt plug to work, maybe not everyday, but for the occasional shift. I need to buy a bigger one though, mine current one will likely just slip out entirely.

Please contribute, I'd love some extra ideas!
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Today is my first day. I've been locked in Chastity since last night, and to start out slow I'm also wearing blue panties, and I tied a pink ribbon around my clitty. I'll obviously be sitting to pee as long as the chastity stays on as well. I also shaved all my body/facial hair yesterday.

I'm still looking for more ideas. Feel free to post some more, I'd really love it! Otherwise, I guess I'll just keep this thread updated with my progress.
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PastelPrince
Well I would most certainly recommend you wear a diaper to work, you aren't old enough to use the potty like a big girl yet.  

Have you considered maybe trying a little makeup? Maybe paint your nails or wear some lip gloss or eye shadow? Do you wear earrings?
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All my diapers I have now are Tena supers, they would be too obvious to wear to work, since I do still need to deal with a couple people. I'll need to go to the store and buy some smaller more discreet diapers. Then I can wear them to work.

As for make-up, I think that would be a little too obvious to the few coworkers around. Perhaps I'll paint my toes though.
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PastelPrince
Well it's going to be a little difficult finding ways to be discreet about your sissiness since you'll be around others at work. A plug would be a nice idea but only if you aren't sitting for too long. Maybe you could find a vibrating one or a vibrating cockring to tease you once in a while.  
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littlemissalexis
How alert are your co workers? If they aren't really night people and don't notice thing easy then you might could also try clear nail polish on your fingers. Maybe wear pefume every few days if someone says something then just saw a girlfriend scent must have got on you. Maybe wear a tshirt bra since they straps won't show and it reminds you all day long you have it on. And maybe pick up some cheaper diapers to wear at work.


Shoes:
If you have to wear male dress shoes to work try wearing pantyhoses with them instead of male dress socks. If you have to wear male tennis then see if you can find women flats or low heels to wear inside of them. If you are require to wear boots then see if you can wear a high heel inside of the boot.
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 Well it's going to be a little difficult finding ways to be discreet about your sissiness since you'll be around others at work. A plug would be a nice idea but only if you aren't sitting for too long. Maybe you could find a vibrating one or a vibrating cockring to tease you once in a while.    




My job is a desk job, so I'll be sitting probably the entire time. Maybe instead of butt plugs I should try tampons. I just don't know if I could really change them at work. A vibrating butt plug I'd be worried about the noise, they tend to be loud from my limited experience. A vibrating cock ring would be really fun, but I don't know how it would work with my chastity device, and how I could turn it on and off short of excusing myself to the washroom.



 How alert are your co workers? If they aren't really night people and don't notice thing easy then you might could also try clear nail polish on your fingers. Maybe wear pefume every few days if someone says something then just saw a girlfriend scent must have got on you. Maybe wear a tshirt bra since they straps won't show and it reminds you all day long you have it on. And maybe pick up some cheaper diapers to wear at work.  




Nail polish would probably get noticed. The perfume thing would work, but our office has a strict no perfume/cologne policy due to potential allergies, or people overdoing it.

I've never actually seen a tshirt bra before, but I'll keep an eye out for one. As for more discreet diapers, I've seen some at the drug store that come in various patterns or colours to mimic panties or boxers, to make them more discreet. Perhaps I'll pick some of these ones up.




 Shoes:
If you have to wear male dress shoes to work try wearing pantyhoses with them instead of male dress socks. If you have to wear male tennis then see if you can find women flats or low heels to wear inside of them. If you are require to wear boots then see if you can wear a high heel inside of the boot.  




Our dress code isn't very strict. I usually just wear a pair of pumas (pumas tend to be fairly androgynous anyway), so I don't wear dress socks. I'll have to find some nude pantyhose though and maybe wear those under my jeans, but still wear shoes on top.

How do you wear a high heel inside a shoe? I've never heard of this before, but my shoes are fairly tight fitting, I doubt it would fit.

Keep the suggestions coming! I'll be trying to incorporate as many as I realistically can. I'll need to go shopping tonight or tomorrow morning after work to pick up some of this stuff. So far on the list:
-Diapers
-Nude pantyhose
-Butt Plug or Cock ring (This will be tricky, not sure where a place on my way to work is that would sell this stuff).
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littlemissalexis


 My job is a desk job, so I'll be sitting probably the entire time. Maybe instead of butt plugs I should try tampons. I just don't know if I could really change them at work. A vibrating butt plug I'd be worried about the noise, they tend to be loud from my limited experience. A vibrating cock ring would be really fun, but I don't know how it would work with my chastity device, and how I could turn it on and off short of excusing myself to the washroom.



Nail polish would probably get noticed. The perfume thing would work, but our office has a strict no perfume/cologne policy due to potential allergies, or people overdoing it.

I've never actually seen a tshirt bra before, but I'll keep an eye out for one. As for more discreet diapers, I've seen some at the drug store that come in various patterns or colours to mimic panties or boxers, to make them more discreet. Perhaps I'll pick some of these ones up.

Our dress code isn't very strict. I usually just wear a pair of pumas (pumas tend to be fairly androgynous anyway), so I don't wear dress socks. I'll have to find some nude pantyhose though and maybe wear those under my jeans, but still wear shoes on top.

How do you wear a high heel inside a shoe? I've never heard of this before, but my shoes are fairly tight fitting, I doubt it would fit.

Keep the suggestions coming! I'll be trying to incorporate as many as I realistically can. I'll need to go shopping tonight or tomorrow morning after work to pick up some of this stuff. So far on the list:
-Diapers
-Nude pantyhose
-Butt Plug or Cock ring (This will be tricky, not sure where a place on my way to work is that would sell this stuff).  




I had a desk job before while try to wear a butt plug. It probably is safer to wear a butt plug than a tampon if you plan on not changing it. But either one does make working hard if you are stuck in it all day. Maybe wearing a plug half the shift while at work. Like putting it doing you midpoint break and taking it out when you get home.

The perfume/colonge rule make sense some people do go overboard. And nail polish on your toes would be fine if your hands would get noticed. And since you are at a desk I can see why.

T-shirt bras are much easier to find by search online but you probably could find them in store if you go searching too. If you want to go to a store and get one might be better to look at there online store first to see what you are looking for. They look like regular bras but without lace or decoration or straps that can be seen in tight clothes.

Nude pantyhoses would probably work fine as is with pumas. And I don't seem to be able to find any info about hiding heels in male shoes online anymore but here is how it works in case curious. Since male shoes are the exact length of your feet then a heel like two inches would be shorter than the length of your shoes because it goes at an angle. So you would make the male shoe strings really loose while you insert the heels into your male shoes then put your foot into them then tighten the string up. The strings might need to be a little long to support the slightly more bulk of the heels but it will go unnoticed in public besides the height increase.
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Yea, maybe wearing one half the day would be a better idea, either way I'll need to find one first though. Tampons I wouldn't have a choice but to change because obviously TSS is a concern for everyone.

I will add t-shirt bras to the list. I hope they are labeled as such in store.

Also, any other ideas people have with which I can further frustrate myself in chastity would be great. I almost wanted to take off the cage and edge and then put it back on again, but that would have been cheating. If I had someone to tie me up and edge me though, that would have been awesome.
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I'm adding pics of the panties I am choosing to wear, and hopefully doing so will encourage me to keep going longer to stay true to everyone here.

Chastity: Me in my cage, the bow only comes off for showers.
Chastity

Day 1: These panties aren't very sexy, so I figured I can only go up from here!
Chastity Day 1
Chastity Day 1

Day 2: These panties are definitely sexier.
Chastity Day 2
Chastity Day 2

Day 3: I think these ones are more cute & sissy than the others so far. I also think they make my butt look better. I just put these on for the day.
Chastity Day 3
Chastity Day 3
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littlemissalexis
I believe the bra should be labeled as a t-shirt bra if it is one.

It is going to be hard to keep topping yourself on panties. If you don't plan on wearing socks over your pantyhoses then while driving to work you could wear heels then switch to your puma once you arrive at work.


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Hehe, thanks. Most of the ones I have that will actually hold the cage are kinda plain. This pair (white with pink polkadots) has 2 small holes now from tne corners on the lock. :(

As for the pantyhose, I'm going to wear socks over them. Plus I don't drive, I take the bus. Thata why its hard to find a place that would sell plugs nearby.

Keep suggestions coming!
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Okay, I stopped at Walmart and got everything I needed, and made it pretty obvious the stuff was for me. I actually had to stop at 2 locations because I forgot to get the diapers at the first one.

At the first store, I bought girl's pajama bottoms, 2 bras (found a t-shirt bra!), 2 tank tops, some lotion & girl's deoderant, 2 pairs of different beige colored pantyhose, and a few other small things. I also got a $50 giftcard because my mom's birthday is coming up (honestly).

At the second one, I bought diapers, baby pink nail polish, and a birthday card for my mom. I wanted to get the women's version of the diapers (the discreet ones) however they only had small in men's or women's, and I require a medium in women's, so I got the men's.

I'll post pics of the stuff later. I'm too tired and need to go to sleep now.
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littlemissalexis
Oh sounds great you found everything you were looking for. Now you can go to work in with nail polish, diapers, pantyhoses, bra, and girl deodorant. You should have fun in your first day in all of that. Glad you found a t-shirt bra. Wearing a bra in public is going to be alot of gun.
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Well, it turns out the white t-shirt bra I bought is a cup size too big (c cup) but the pink one I bought is the perfect size for me (36B) and doesn't look like it's going to show under my t-shirt. And the nail polish I bought isn't actually baby pink like the colour on it appeared, it is sheer pink, so it's barely noticeable on my toes. :(

So as it stands, I'm ready for work wearing a bra, a diaper, polished toes, pantyhose, and girl's antiperspirant.

Picture updates!

What I bought:
Shopping!
More shopping!

Modeling my PJs & what I'm wearing to work:
Pajamas
Work attire

And finally, chastity day 4:
Chastity Day 4
Chastity Day 4

I had to take off my chastity earlier today to shower & and clean it off (the first time since I started, and I played with my clitty. I feel so bad. I edged like 5 or 6 times in the shower. I didn't make cummies, but I shouldn't have been touching myself. If you want to administer a punishment, I'd be happy to do it, it would make me feel better. I think the punishment should fit the crime though, so something to make me more frustrated would be fitting. I already use a vibrating egg in my bottom and one on my cage at the same time while looking at the cappies on here, and that was very frustrating, but I need something more.

EDIT: I took the bra off :( While the straps weren't really noticeable, it is padded so it added some noticeable bulk to my chest. If I could wear a hoody I'd still wear the bra, but it is way too hot here right now.
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littlemissalexis
That's great you got a great collection ready to work in now.

It is a shame they didn't have the women's depends. I never saw the male and female before to day. The males ones really do look like male underwear and the female ones look like panties. It is a shame the T-shirt bra cups wear to big but I guess you can fill the cups out at home. Next time you go to walmart I am sure you we pick a darker pink.

Are you sure the bra is noticeable under your clothes. Sometimes it only looks that way because you are look hard for it. I think a good punishment would be buying a plug from an online site and ordering under the name Jessica. Leave the key to the cage outside somewhere, dress up fully plus the plug, and play a movie that turns you on. Don't remove the girl clothes into morning.
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Yea, I would have liked the women's, but oh well, gotta work with this.

I'm definitely going to use the tshirt bra at home. I actually wanted a hot pink bra to match my pajamas & tank top but I didn't see anyway. The bra does make my boobs kook bigger under the tshirt unfortunately.

That punishment sounds fair except I can't order it under Jessica's name, because my mom won't sign for it and I won't have ID to pick it up. Plus, ordering online delays my punishment. I'm still trying to find a place to get one though. Is it acceptable that instead of leaving the key outside, if I leave it at work for the whole weekend? Also, is it okay to change girl clothes for bed (wear girl's pajamas or a nighty?)

Also, saturday I'm going to a fetish pajama potluck as Jessica. They are going to have a spanking corner so I'll get some extra punishment there, hehe.

EDIT: 7am. I decided to wet my diaper when I got to work last night around 10 30am, and the diaper leaked! At work! With no change on me! It soaked through the diaper & my jeans, and into my chair. I had 2 wet spots on the back of my jeans, luckily I think they were dry enough by the time I had to leave. I wouldn't recommend those diapers to anyone unless you just like the feel. For wetting, they are terrible. They had no odor control, so on top of it, I smelled like pee most of my shift, with my co-worker around. On the bus on the way home someone got up to move away from me! And it doesn't have very much absorption. I'm definitely not wetting one of these ones again.
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littlemissalexis
Yes that's very acceptable. I had originally plan on you leaving it at work so that work well. And if you find it in a store that is good too. I had imagine that if it was delivered the delivery person would just say a package for Jessica and leave it. I didn't think about if you had to go pick it up.

Sorry to hear you have a bad experience with those. I know normal depends really can't handle double wetting or a heavy wetting well though the newer ones might have been better.
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I was in a rush this afternoon so I never got a chance to put on my panyhose this morning. If you think I deserve a punishment I will understand. After yesterdays diaper incident I decided to wear panties today. Ill post the pics when I get home.

I did howevee get to a sex shop today. I bought a pink buttplug that is kinda curved so Im hoping it will massage my prostate constantly. Its called the pixie and its pink with a suction base. As per earlier discussion Ill wear it for the second half of my shift.

I also picked up a solid pink gspot vibe. I read that type
it is good for prostate prostate milking. Tje girl had to test it at the store and it didnt work. She tried 3 while otjer customers were waiting. Turns oit it was just her batteries.

Ill post pics of the toys later as well as a review in the appropriate thread. So if you want to give me a punishment for being in a rush and forgetting pantyhose and to post my daily panty photos on time i understand.
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Okay, I got the pics up.

Toy shopping:
Toy shopping

Chastity Day 5:
Chastity Day 5
Chastity Day 5

I wore the plug for half my shift, and I was actually happy to get it out when I got home. The base on it was starting to dig in to my bottom. It felt really good for the first little while, but after a while it just started to hurt. Since it's jelly, it was also tricky getting it in.

I haven't had a chance to use the vibrator yet. I could have sworn I had batteries (it takes 2xAAA), but I guess I was mistaken. I'll have to get some soon so I can try it out.
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littlemissalexis
Since it the weekend for not wearing you pantyhoses you should wear them everywhere you go this weekend without socks. Hopefully you have some your skin tone so it won't show while out.

*giggles* See aren't you glad you only did that half a day and not a whole day. I totally been there. It is not great for jobs where you sit down a lot.


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I can't do that punishment unfortunately, as I will be without shoes a lot this weekend and will be having friends over (we don't wear shoes in the house), not to mention I still live with my parents. Besides, I want to show off my painted toes at the pajama potluck. My weekend doesn't start until tomorrow morning either :(

Is there anything I can do to make up for it? I'm sorry, I really want to do something but I need to be realistic.
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I had taken my panty pics with my new phone but I have been having issues transfering it to my computer so I haven't been able to get them up, but yesterday's panty choice has been the most uncomfortable so far. For some reason at one point it rotated the cage sideways and had to be adjusted (didn't require unlocking though). Another time it had bent it at a weird angle. Either way, not thrilled.

The keys to my chastity were left safely on my desk at work this morning. Now if I want to get them it is minimum 1 hour bus ride both ways with terrible busses, so basically, I am stuck without the keys until 10pm Monday night. I will be doing the plug punishment tonight when I get home from the pajama party.

I spent about half my shift yesterday reading Miss D's blog at work on my new phone, and it made my clitty very leaky. I was very horny & frustrated. I got home and read some more for about an hour, still more frustrated. I decided to try out my new vibrator to try to milk myself. It felt very good in my bottom, and I was dripping in my chastity. I decided to try something else so I pulled it out and placed the vibe against my chastity cage. It felt absolutely amazing! It was the single most frustrated I had ever been, it felt so very good, I was practically edging in the cage without even touching my clitty.

However, somehow this sent me well over the edge and I made a sticky sissy spurty in my panties. This was more of a full blown orgasm than a sissy orgasm. And while I did it in the sissiest manner possible (legs clenched together, hips thrust back with a vibrating on my chastity) I still feel really bad about it. I didn't want to have a full orgasm! And after it happened the chastity started to get very uncomfortable. I wanted to remove it, it was very heavy to my now sensitive clitty, and very itchy for some reason. But since I left my keys at work I was still stuck, so I still have the chastity on.

I feel really badly about cumming, and I promise now that I know it is possible I will only use the vibrator for edging and leaving myself even more frustrated. But I think I deserve a really big punishment for breaking a most basic sissy rule, even if it was an accident. Please punish me!
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I was shaving & taking a bath this morning, and as I was sitting there in the bath, one of my balls slipped out of the chastity somehow! And since I left the keys at work, it made it a rather difficult situation. So here I sit without chastity on after having removed the other ball, since I can't get back in without the key.

Also, I went out to a fetish event. It was my first time dressed as a girl infront of anyone, and it was an amazing experience. Everyone was so supportive and friendly, and I got a ton of compliments. The mistress hosting the party has invited me to another event already (though I have to work that night) and even offered to take me clothes shopping with her! It sounds like so much fun, I'll probably have to take her up on it. Apparently she loves taking guys shopping for girl clothes.
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DSummer
Please avoid wearing tampons... butt plugs, dildos, chastity belts with butt insersts, are all good ideas, but tampons are not.
Dawn Summer
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