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View Full Version : Crossdressing Time [Single] [R]


FatGuyOnCam
08-17-2008, 09:02 PM
Okay, first dare, so go easy on me. One typical six sided dice will be used. One re-roll per category is allowed, but if you re-roll you'll have to complete the task within the brackets under the category.. If there's any task you can't complete, due to limits or other reasons, just skip it and continue.

Firstly, of course we have to decide just what to wear!

Panties:
1. Full Bottom
2. Boy Shorts
3. Bikini Cut
4. Thong
5. G-String
6. None
[Insert an item anally.]

Bra:
1-3: Bra
4-6: No Bra
[Clamp a nipple. Any nipple. Use anything.]

Socks:
1. Above The Knee
2. Knee Length
3. Crew Cut
4. Ankle Socks
5. Toe Socks
6. No Socks
[Get those toenails painted.]

Top:
1. Sweater
2. T-Shirt
3. Unbuttoned Button Up
4. Halter Top
5. Tank Top
6. Any of The Above
[Paint the fingernails, now.]

Bottom:
1. Tight Jeans
2. Tight Shorts
3. Knee Length Skirt
4. Mini Skirt
5. Micro Skirt
6. Any Of The Above
[Go commando if you're not already.]

Shoes:
1-2: Gym Shoes
3-4: Sexy Heels
5-6: Sexy Boots
[Lick the bottom of your soles.]



Now, lets ask the question, what would a girl do? In this section, the one re-roll still applies, but now the re-roll "punishment" is listed at the end of whatever your number you roll, again in brackets.

1.
Shave. Girls like to keep their skin silky smooth and especially hairless. Your task is to, at the very least, completely shave your pubes. Do this where ever your prefer, but do it keeping on all the clothes possible. The only clothes that should be removed are underwear and pants/shorts. [Also, shave your legs.]

2.
Fuck the hole. Girls love to have things in their hole, no doubt. Guys only have one hole "down there", so we'll put that to use. Fuck your asshole with an object of your choice while jerking off until you cum. [Once you've cummed, lick at least the length of the object.]

3.
Suck it off. Find an object that you can practice some oral skills on. It can be a vibrator, candle stick, carrot, whatever. Put this in your mouth. Suck it and lick it, all the while jerking off. Continue until you blow. [Since they say cum makes a good lube, lube the object up with your cum. Insert into your ass for at least a few seconds.]

4.
Spit or swallow? Everyone knows girls who swallow are the favorites. Jerk off, collect your cum, and be sure to swallow every last drop. [Specifically shoot your load over a dildo-like shaped object. Now, clean it off with your mouth. Of course, don't spit!]

5.
Put on a show. Get some stripper music going and slowly, slowly strip. Get a dance going. Smack your ass. Spread your legs. Do the splits if you can. Tease, tease, tease. [Whip out the webcam and tape yourself for your brand new dance movie. You don't have to share it with anyone, but just be sure to keep the copy saved for at least a week. Watch it at least once.]

6.
Exhibitionist. Use common sense here folks. Go someplace outside of the walls of your house, someplace where you can be alone for at least the duration of your dare. Just be sure to make sure you're dressed appropriately before leaving the house. Go for a drive someplace secluded, the woods behind your house, etc. Choose a dare from the five above and do that dare there. [If you've re-rolled yourself to this place, also do the re-roll bonus for the dare you choose from above.]



Hope y'all have fun with this! I've yet to even begin this, but I'll keep ya updated on my status.

FatGuyOnCam
08-17-2008, 09:46 PM
My rolls were:

2. boy shorts
6. no bra
2. knee length
6. halter
5. micro skirt
3. gym shoes
2. fuck the hole [lick the vib]

Step two is for me to actually get the clothing.

Shiney
08-18-2008, 11:17 AM
Great dare. I got

5. G-striing
1. Bra
4. Anklesocks
4. Halter top
5. Micro skirt
1. Gym shoes
4. Swallow

I'm all dressed up right now. It's quite fun.

garbonzo222
08-18-2008, 03:29 PM
amazing dare...i like the sucking the cum off of the dildo ones

meizsammyg
09-02-2008, 01:16 AM
i got
4= thong (god they ride up)
2= bra
4 ankle socks
5= tank top
5= micro skirt
6= sexy boots
2=fuck the hole (hurt)

good dare though I thought it was quite fun

≈ Wedgies ≈
09-02-2008, 02:47 AM
Great Dice dare but I'm scared to try it. :eek:
A little help to get a thong without being seen or being suspicioned?
:(

krakatoa
09-02-2008, 03:01 PM
Great Dice dare but I'm scared to try it. :eek:
A little help to get a thong without being seen or being suspicioned?
:(

Online shopping FTW :D

≈ Wedgies ≈
09-04-2008, 11:30 PM
Oooh, yeah just walk into to Target and buy one. :)

RareLyon
02-20-2009, 07:21 AM
1. full bottom
2. bra
3 crew cut + re roll punish=paint toe nails
2. t-shirt + paint the fingernails
4. sexy heels + lick sole
5. put on a show + videotape it :S


This should be fun, I'll just wait 'till im home alone...

Kolia
03-30-2009, 01:35 PM
Ok so starting with rolls, [#] means re-roll and # just means it was the first roll

[3]
1
[4]
[3]
5
[1]

Dare is [4]

so i started by rolling everything and then started painting all my nails with purple sparkling nailpolish. I wore mainly my sisters cloths then got the dildo ffrom her room for the second part of dare 4. I got all her cloths and put it on and then went back to my room, and started masterbating. For the object in my ass i put in a dry erase marker i usually write on my mirror with. I was so horny after i came after like 5 mins dressed. So i came on the dildo and licked it nice and clean. Was a decent dare.

Kilika
08-16-2009, 04:37 AM
I love this dare, and sorry I am bring up old dares but I really do think this one was pretty good.
4. Thong
1-3: Bra
1. Above The Knee (Idon't have any)
[Get those toenails painted.]
4. Ankle Socks
3. Unbuttoned Button Up
6. Any Of The Above
(4. Mini Skirt)
5-6: Sexy Boots (don't have any)
[Lick the bottom of your soles.]
1-2: Gym Shoes
6.Exhibitionist.
(2.Fuck the hole.)

So I grabbed my black thong and matching black bra (stuffed) put them on along with my maroon dress shirt unbuttoned. I got any of the above for my bottoms so to make the outfit work, I decided to go with the mini skirt to add to the dare I also put on a pair of thigh high stockings. I got all dressed up, oh It felt so nice to dress like that hehe (sorry going off track)...anyways I painted my toenails red as for that was the only color I have. I licked the soles of my shoes and put them on after the paint was dry.

After I was all ready I walk outside my house and into the woods near my house. (Well I guess I wouldn't say walked lol more like run/sneek without being seen.) Pulled out my dildo and started fucking my ass, slowly at first, then over a short period of time I worked my way to going as fast as I could while as slowly as I could, I jerked off.

Since My master has not said I could cum I decided to alter the very last part to fit my needs. As I neared my cumming point I stopped and just fucked my ass as hard and fast as I could while sucking my fingers as if giving a blow job for a few more mins. My arm got very tired so thats when I decided I was done. :) I felt sexy though and just laid there for a couple mins while I regained my composure. Pulled my thong back up and being a little more daring bc of how much I really wanted to cum, I actually walked back home on the sidewalk with my shirt buttoned up but unbuttoned and tied at the bottom like a girl would do. :) I was scared shitless, but dam was it exciting. Luckily only 3 cars passed me hehe.

Thanks for the dare.

Neptune
08-16-2009, 06:10 PM
I may try this dare later. I'm not a huge fan of cross-dressing, but you put a great deal of thought into the dare.

The best part is the re-rolling mechanism: it adds an extra element of risk-management and seems quite innovative (forgive me if it's been used before).

fetish18
08-19-2009, 03:23 AM
3. Bikini Cut

1-3: Bra

1. Above The Knee

3. Unbuttoned Button Up

2. Tight Shorts

5-6: Sexy Boots

5.
Put on a show. Get some stripper music going and slowly, slowly strip. Get a dance going. Smack your ass. Spread your legs. Do the splits if you can. Tease, tease, tease. [Whip out the webcam and tape yourself for your brand new dance movie. You don't have to share it with anyone, but just be sure to keep the copy saved for at least a week. Watch it at least once.]

lol