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Old 12-17-2014, 09:03 AM   #16
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What comes after stockings? I'm curious in the event that someone really screws up, what order do they add things on before they get completely and fully feminine?
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Old 12-17-2014, 02:37 PM   #17
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I am currently nearing the end of my second day doing your challenge Miss Kate. For the first day, I went to a local Ann Summers, the day before, with a note saying I had lost a bet and it asked them to pic some lingerie out for me to buy and wear out of the store. It was truly humiliating but also so much fun.

On the first day I was at one of my best friends house so I stole a thong she had left on the floor of her room, which I then wore today.

I've been / will be uploading photos daily to an album here however I did't upload the 1st photo till the day after so I was wondering must I do a punishment or is it the standard add an extra item?

Also what is the order for the extra items to be added?

Ill update you all in a few more days
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Old 12-17-2014, 02:55 PM   #18
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Well, the second day, 16/12, I wore the pink knickers with the bow in the middle of the waistband and it felt exactly as I thought it would. I have underdressed to work before and this just helps my confidence levels. I wear a full suit and so the chances of people seeing this were next to zero. As my wife is currently ill and we haven't had anything approaching a sex-life of normality since we got married there has never been a chance of her catching me dressed, and so far no exception.

I do face challenges in sneaking clothing into the house - she is not supportive of my cross-dressing at all - but that's the only real problem. Washing the clothes is impossible as a consequence, though now we have a local laundrette perhaps I ought to availing myself of their services. Still, on the evening, after the meeting, I did indeed make it down to a supermarket on the way back from work. They only did packs of knickers so I got a boring set of black knickers, hi-legs, and wore one of those today.

Same drill at work, it's actually quite a nice habit to get into and for the prices of the knickers so far I can see that this won't break the bank. Once again, I got a smidge of confidence boost from underdressing - though I'll confess that I find hi-legs less comfortable and comforting than full briefs. They do have a habit of riding up. Mind you, I realise that I am pretty well looked after generally, coming in at a UK size 12-14 in smalls. Good day had, some minor stresses, and another late finish as I was helping a student with essays by scribing for them - this meant another dash to the supermarket. Pastel colours (different place) and minis this time to break my brief habit. Tomorrow looks like being an aqua-green day, as I haven't worn green ones before. I shall try and keep people updated.

Hope this is interesting, let me know if it isn't and I'll cut it all down.
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Old 12-21-2014, 04:36 PM   #19
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I've decided to enter the challenge as it has pretty excited me when I saw it.

And today, thanks to Xmas (but I think it will be harder after because of Xmas), I could buy my first panty today. For the fun, I went out in commando, and I went in a specialized shop. The good thing is that there was not much people in the shop, the bad thing is that I get a little too much excited by all those pretty lingerie. One of the selling women comes to help me selecting one. After giving here the size and the kind of models I'd like, she presented me some models, I picked one string and then she asked me if I'd like the bra matching the string, I almost say no but I thought it will be a little too strange so I took it, giving some size. I was pretty hard during all the conversation, and she told me that she probably love it as much as I love it. Hopefully, the dare here is not hiding a boner.

Let's see tomorrow how far it will go.
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Old 12-22-2014, 01:16 AM   #20
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Yesterday I put on my prettiest pink full panties with a ruffle on the top back, the lowest cut jeans I have and a not to long top, making it hard to hide the ruffle on the back.
With my GF off to the side I had to ask the sales lady what the best type of panties would be for me, and what size would she recommend. She took her tape and measured the widest part of my buttocks, She picked out a size 7 full cut pink panties with lace,saying it will complement the panties I have on, so we head to another store to pick out a bra.

So today I wore the panties with the un-padded cross your heart bra, with a tight fitting top, with skinny jeans.
I'm use to buying panties and wear them daily so my GF upped the challenge by making me ask for help. Since I have been caught in panties that means I will be wearing a bra for the rest of the week.
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Old 12-22-2014, 05:17 PM   #21
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Hard day of work but nothing really happend, each time I was sitting or standing up, I was checking that my shirt was still in my pants, just to be sure . Having some excitment made my sex go out of string so I decided to go buy a cotton panty after my work. I went into a cloth shop and don't know why I felt I'd prefer a nice little girly boxer. So I took one really designed for girls (but sell for woman why not). And then go home.
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Old 12-23-2014, 10:51 PM   #22
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I have to admit, a panty give nice sensation, less sexy but more confortable. I really understand why girls prefer putting this during their period. It felt less risky to be caught, so it was in fact more as I was less checking. Before coming home, I've looked for a nice panty for christmas eve and I've decided to have some fun and put a little red string with a white bow for today.
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Old 12-25-2014, 08:27 AM   #23
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Well yesterday was pretty fun specialy with a christmas string . Not much to say, had some fear with family while taking gift under the tree.

Iv taken a little panty for next day but I think I'll have some problem to find another one on christmas day.
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Old 12-26-2014, 04:40 PM   #24
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Well as I expected, it is hard to find a shop open on christmas day especially when you wake up at the end of the afternoon, so I have done some walking on christmas day to tire me so I could have some fun out there and well had to go commando and add 1 cloth and 1 day.

Today was really hard as 1 of my female collegue had a rendez vous so she was dressed really sexy. After all this emotion and cold helping, it was pretty easy to go buy a panty and a matching bra in a lingerie shop. The sellers were just surprised I bought lingerie after christmas...
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Old 12-27-2014, 10:11 AM   #25
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With a bra and panty is really more strange for me, I felt the strap of the bra falling some times and couldn't put it back any time I'd like. I had a little shopping moment in a supermarket to buy food and a bra + panty for tomorrow, It felt like a very long time as the strap of the bra have felt, I had the feeling everyone was seeing it, it was really hard, I think I'll have to find a bra without strap to finish the dare as it is very disturbing for me, it annoys me so much, I even forgot I was wearing a panty. After the supermarket, I went home to deposit the food and new bought cloths and decided to go for a walk in a park. I think I'll need more practice with bra.
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Old 12-29-2014, 07:41 PM   #26
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On Sunday, I've been waked up by a friend who wanted to go for a little run on bike across woods so I had to dress up as my friend was on the other side of the door, I was so scared, I think I've dress very fast but this time I tighten the bra strap. The run was so long and I was so afraid my panty goes up, I've let my friend decide the direction and follow him during the two hours long session. After this, as it was sunday, I thought it will be good to start searching for a shop that will sell my wanted panties.

I thought it will be easier as it was Sunday but in holiday season except Christmas was gone and a lot of shop were closed. So I began searching for a place on my phone and found that a commercial center was open, 1 hour later I was in and in fact, not all shops were open. I started looking for female lingerie shop but they were closed so I went into a cloth shop. I started looking for lingerie and well I found some really pretty stuff but not the kind I wanted. The next shop was really more interessant with more see through undies and found a nice little purple see-through panties and a matching bra. Before going to pay, I saw some nice stockings and well as it is a pretty cold period, I decided to buy a woollen tights with it. After buying it, I decide to go home and take a nice tea to warm me up.

Next day, after dressing, going to work with my tights under pants was really great except that at work, it was pretty hot, so I began to drink a lot and so I had to go to toilet a little more. Well it was great for one thing, I could check that all cloths were in place and some were not visible. After Work, I could finally go buy my last (I hope) female undies for the dare. And so I have gone to a female lingerie shop and I have take .... surprise for tomorrow
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Old 12-30-2014, 06:27 AM   #27
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This sounds like real fun. I will do it
But what shell I do on the sunday. Here in Germany all stores are closed on sundays?
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Old 12-30-2014, 04:59 PM   #28
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Consider you'll have a day more and a piece of cloth to add in

So today, I have put the nice cloths I bought before, a nice pink (but not vulgar) g-string with some nice strings tightening around my ribs and a pretty bra that is retained by a string around the neck. I'm really found of it. As it is pretty cold and as I liked it yesterday, I put a nice white pantyhose, it warms a little but less than yesterday. I felt so sexy and stupid and excited by the nylon, my dick didn't stop growing and going soft today. It was really hard. I fear this day, and felt so well in my lingerie. My mind could stop focus on my lingerie. I had to well calm a little bit in toilett at work today. I think this is good I didn't have to continue more but I think I will wear more stockings this winter.

And today we had more work than usual surely because of christmas and new year so I have finished pretty late. Going home was so scary, at night with some men looking at me, I think I know now why so many women fear going home late. Hopefully I didn't excite him enough so going home was more some excitment of fear of being caught than real problem.

Thanks Miss Kitty for this idea of dare anyway, it was pretty fun.
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Old 12-30-2014, 10:40 PM   #29
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Quote:
Originally Posted by CrazyFunDare View Post
This sounds like real fun. I will do it
But what shell I do on the sunday. Here in Germany all stores are closed on sundays?
Ask a female friend for some.
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Old 01-27-2015, 06:35 PM   #30
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Sorry I disappeared, Christmas was insanity.

But thank you so much to those that played along. I must admit I felt very excited and powerful reading along.

I caught a snippet of pink on a male coworkers waist the other day and it made me wonder, what if he was doing my challenge! If so he didn't catch me looking, because he wasn't in a bra the next day!

For those who wondered about the order, and for the benefit of those who might stumble onto the challenge in the future, I was going to leave it to your discretion, but for the want of rules, let's do it this way:

1. Panties
2. Bra
3. Stockings.
4. Painted nails.
5. An additional article of lingerie: garter belt, teddy, corset, waist cincher. Etc, your choice what.
6. Female shoes (can be subtle)
7. Make up.
8. Female lower body wear. If you can still hide, great, try jeans or trousers, if not, may as well be a skirt
9. No male clothing.
10. Sex toy. Your choice.
11. Cock. You'll need to find one that isn't yours to play with per day til you finish.
12. You lose the challenge and must continue playing forever.

Hope this helps... Certainly helps me!
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