Cross-dressing Dares List Thread

[Mercifulcd]

Wear a sexy maid outfit with a red thong and bra and DD and wash 2 windows in your house

My clothes:
Bras (all D cup) Pink,cheeta print and black lace
Thongs Black ,pink ,cheeta print ,black lace and red assless
shirts green tube top, blue tank top, black tank top
pants yoga, jeggings ,leather knee length frizzy skirt and 6 inch tight black skirt

have a 6 inch homemade dildo

nothing public, long

[Sissy Slut 619]

Put on a bra and a thong (both pink). Put male clothes over the top and go for a walk around your block, when you return you should fuck your ass with your dildo until you cum however, you may not touch your dick while fucking your ass

[GumdropGirlyboy]

Been a while since i did one of these. Hope you like... Let's start with latex from neck down but with bare feet, then a cute tutu or mini-skirt and bra over top. Then let's take a 'dislike' just to make it more interesting, find somewhere outdoors but secluded or dark, even a back yard or porch. Now take each toe into your mouth and suck on it as if you're giving a little blow job to each toe, counting 50 "strokes" each working from your pinky toe to your large toe and when you get to your big toe you need to stroke the bottom of your foot with a feather or something that will tickle. After you've completed that task, masturbate and massage your feet with your cum before another round of sucking each toe as described above. Would luv for you to post your thoughts and feelings if you return to this thread.

[janesg]

Start by being dressed in skirt, top, bra, panties, and heels, and be tucked.
Your task is to put on some music and do a slow sensual strip tease show until you are naked.
The catch is, you have to remove your panties first.
If at any point you get hard, then you must freeze in position until you are soft enough to continue.
Once you are naked, reverse the procedure until you are fully dressed and tucked. Your panties should be the last item you put back on.
Your reward. Should you manage to strip and redress without getting hard you may orgasm how you like. If, however, you do get hard, afterwards you must edge for each time it happened before tucking yourself again.
Recommended is that you do this in front of an uncovered window, however, use your own judgement and limits as to how you perform your strip. Enjoy :)

[BabySissy]

Wear a stuffed bra, thong, and dress and over it a big coat. Go to a store and buy something a girl needs (tampons, girl shampoo, etc.)

[SissyKija]

Wear a stuffed bra, womans blouse, thong, yoga pants and some heels. Go to the store and buy some condoms.

[TestMeMiss]

Wear slutty underwear every time you are wearing a dressing gown for a week.

[janesg]

Find some panties and put them on, wear no other clothes.
Get on your knees, and post in the Teased by Girls thread, tell them what you are wearing, and beg for some edges to do in your panties ;)

[lovedegrading]

i want you to tie some string or ribbon around your balls, tight enough to hold on without doing serious damage. Make sure there is spare string hanging down. Now dress in bra and knickers and insert a dildo or similar in your ass. Put the underwear in a bra connection wedgie. Get on your knees and attach the spare string to your big toes... you'll need 2 pieces of string otherwise attach more to the dangling end. It must be sufficiently short so as to cause discomfort if you stretch your legs by more than a few inches.

You should also have to hand 5 pairs of womens knickers. Put them ALL on your head, so your vision is impaired hopefully! Now, you must visit your bedroom, bathroom living room and kitchen all without standing up and all without removing your knickers from your head. I have no idea about your house, so quite arbitrarily I'm going to give you 3 minutes to complete this, from when you are ready to start moving. If you succeed, you may reward yourself any way you wish. If you fail, you must crawl to the bathroom, into the bath and stay there until you have both peed yourself.

Sorry for the lack of originality but i wrote up a dare without seeing cam was a limit. This however, did seem fun haha ;)

[jana-sissy]

At night, get dressed in in panties and a stuffed bra, with pants and a sweatshirt over them. Go for a walk to a secluded spot atleast 1 km away, taking a large dildo or cucumber with you. When you get to the spot, take your sweatshirt off and pull your pants down, and deep throat the dildo or cucumber for 5 minutes. If tou want added difficulty, you must masterbate and cum on your object, then suck it off.

[BabySissy]

Put on your sluttiest outfit and go check the mail, or if that is too far, stand in the door or window in it until 5 people pass.

[hunter]

Dress up as a baby girl and wet your diaper say in it for 2 hours and cry a lot

[kycats]

Wear your french maid's outfit and stand in front of a window with no blinds or curtains. You must fuck yourself with your dildo until you cum. Make sure to cum on the window, then lick it off.

[Moonspell]

Wear a schoolgirl/student outfit (with skirt).
Cover your nails. Light make-up.
Then get a good wooden spanking implement (paddle, wooden spoon, hanger), set a phone for record video, bend over, lift up your skirt and punish every cheek for 30 times.
After this you must show us photo of red bum. And you may cum, while watch video.

[Moonspell]

bump
..........................

[GumdropGirlyboy]

bump
..........................
Difficult to work out what to give you since you list crossdressing, feminization as dislikes, especially in this thread. However, since you're here I think it would be appropriate to have you dress up in panties, girl's shoes (pref heels) short skirt or dress and bra and take a drive. every 3 miles/kilometers pull into a parking lot or gas station and edge while making girlish whining and moaning sounds and saying things like "give me your hard dick daddy" and "I want hard cocks inside me". You must make at least 5 stops on the way away from your home, and then the same number on the way back homeward. (or roll three 6 sided dice for the number of stops) you may cum on your last stop before returning home.

[BabySissy]

from the time you wake up, to the time you go to sleep, i dare you to wear panties, a bra (not stuffed) and paint your toe nails. see how long you can go without anyone finding out what your wearing underneath

[kycats]

First you need to cum in some panties and save for later. Then get dressed up in a bra, panties, and a skirt. Put the cummy panties in your mouth with the cum on your tongue. Tape your mouth closed with duct tape, and tie your ankles and knees together. Write "Cum Slut" on your stomach and take a pic. Keep it as your phone background for a week. You can masterbate and cum if you want, but if you do you must smear it on your face.

Something outside and maybe messy for me please

[hunter]

kycats is banned so I'll take the next dare ;)

[Bdsmmsdb]

Put in your 6 inch dildo and wear your maid outfit and clean the house at least for an hour

For me I would prefer a public dare but under my clothes or in a secluded area, prefferably outside, there is snow outside, almost 4 inches

Please be creative and I will be eagerly awaiting my challenge

[rogue_9]

You are lucky that you still have snow. So you will insert your 8 inch dildo and wear your slutty tight panties and a bra under your normal clothes. Go outside and make snow angels. Make sure you apply lots of pressure to your butt whilst making them.

[laraw]

Put on nail polish, a diaper and a stuffed bra. Put on a nice dress and heels. Stay like this for the rest of the day and watch some girly shows.

[BabySissy]

Wear a stuffed bra under your clothes and use a drive trought or go for a walk for at least 1 hour.

[lovedegrading]

Roll two dice, the first determines what you wear whilst the second determines what sexual activity you'll be doing:

1st roll -
1: Genuine - try to look as womanly as possible with makeup, clothing shoes, wigs, stuffing and tucking. Get it perfect.
2: Sexy - Lingerie is a must, stockings, thongs, corsets all work well here. Make sure you have dark lipstick and heavily shaded eyes.
3: Camp - Try to look as ridiculous as possible; pink and glitter would go down well here and are really necessary to complete the look. A tutu is another must have.
4: Underwear - Just your bra and panties. Stockings/tights are also welcome.
5: Weird - Fluorescent wigs, dodgy makeup, mismatching outfits, enlarged 'breasts', anything to make you stand out.
6: Over the top - Outfits are the order of the day. from Fairy princess to sexy nurse.

2nd roll -
1) On your knees - give you dildo a kiss and then relentlessly suck until the time is up. If this is required for longer than half and hour you may take a minute out every 5 to gather yourself.
2) On all fours - lube yourself and your err 'partner' up generously. Slowly insert your dildo and gradually gather pace until you cant go any faster...after 30 minutes of going faster, slower, faster, etc you can go at your own pace.
3) Legs wide open - you can touch yourself...but only with a finger inside you and whilst you moan haha.
4) Warming it up - you'll be doing roll 1 for half of your time followed by roll 2.
5) A2M - you probably can tell...but for the slow: do roll 2 then roll 1.
6) 2 for one - if you have a plug then insert it, if not insert whatever toy you are comfortable with keeping inside you for a bit. Now you have to roll in one of the other sections (keep your duration).

[thenewslave]

This anal loving whore says:

Crossdress as fully as you can. Now spend 2 hours doing girlie stuff.... no masturbating or porn. Cleaning, ironing, are allowed, as is watching soaps or shopping if you are feeling brave

After 2 hours, go on line and google "pictures handsome men". You may now masturbate to the pictures.

[laraw]

You got to wear white lingerie including a stuffed bra, panties, garter belt and stockings and some black high heels for this. Clean the floor in one or multiple adjacent rooms and hide a release in one end. Go to the other and hogtie yourself. Include a gag and a blindfold if you like. Also hide the the release somewhere where you might get exposed if you enjoy such a thrill.

Make sure you get someone to check on you in case you can't free yourself. And play safe.

[laraw]

bumping this thread

[marystoy]

Black or red lingerie. Stuffed bra, thong, garter and hose, highest heels. Heavy, dark makeup. Wash every window in your house twice.

[madgord]

wear a super tight thong to work

[Winforce]

Put on pink panties and wear it for 5 hours straight. You can start anytime you want as long as it's not when you're sleeping.




Limits: Public,Involving Other People, Illegal, Pee/Poop, High Risk of Getting Caught,Extreme Pain,Anal,Messy/Water

[madgord]

ok i dare you to wear a dress for an hour and do whatever you need to do while wearing it such as watching tv or cooking

[laraw]

Wear a stuffed bra and matching thong under your normal clothes. Bring a bag. Go to the cinema, a film with only a few visitors. Once the lights go out. Strip all your normal clothes. Put them in the bag and throw the bag 2-3 rows away from you. You can get back your clothes 10 minutes before the credits.

[madgord]

seeing as you havent gotten a dare yet i dare u to wear a dress and go on a stroll by the park or around town

[Winforce]

i dare u to wear matching bra + thong or panties if u dont have a thong
for 1 day

[Victoria85]

Wear a stuffed bra, pair of panties and stockings for a day. Also sleep in them

[marystoy]

Wear pantyhose for two days.

[BabySissy]

Sleep in a big stuffed bra for 3 days

[dgaz]

Get dressed as a maid and clean your entire house from top to bottom, when finished, ask someone to inspect your house for dirt (dont have to be in maid uniform for this bit) - each bit they find is a day you must wear panties and bra, with painted toe nails.

[lovedegrading]

You'll be in chastity until the dare is over. Starting with panties you will continue to add one female item of clothing to your overall outfit each day. Stockings, shoes, anything in pairs must be worn at once. Different makeup counts as an item (foundation, lipstick, blush) as does jewelry. If you can make it to 7 days then you may cum using anal stimulation, make it to 10 and you are free to orgasm how you wish. if you cannot get to at least 7 you will spend 15 days in chastity. If you get to or exceed 7 but fail to make it to 10 you will have to wear panties whenever you wish to cum for the next week.

For example you could choose to wear panties and stockings on your second day, on the third panties stockings and a bra, etc, etc.

[laraw]

You should enjoy the Long Walk (http://www.boundanna.com/html/en_scen_longwalk.html) from boundanna.com.

[Cookie lover]

Wear panties when u sleep

[Victoria85]

Wear a bra for a week

[Poopingsissy]

Roll a dice and that is the number of articles of clothing you must take off and replace with the feminine version of

The six articles you can take off and they're female version are

Pants -skirt
Underwear- panties and bra
Shirt- blouse
Shoes- heels
Socks- stockings
The last thing is just put on make up

[Poopingsissy]

I want to die of humiliatio so please be creative

[Streetwise]

Next time you go out for more than two hours wear a thong in a wedgie. No tucked in shirt to hide it. Be proud

Can I get one that is predicament.

[laraw]

My previous dare in this thread will be something for you i guess

You should enjoy the Long Walk (http://www.boundanna.com/html/en_scen_longwalk.html) from boundanna.com.

[Poopingsissy]

My previous dare in this thread will be something for you i guess

I like this dare it's yours and if your feeling risky send pics


Anything suited for a pooping sissy

[Blue Griffin]

Wearing just a skirt, bra, and makeup you have to lay on the ground in front of your door. Draw 50 pink hearts and 25 flowers on a diaper. Now either you can wear the diaper until you use it or wear it for an hour with a pair of panties on your head.

[janesg]

From when you read this until bed time you are 7 months pregnant and must dress and act that way at all times. Spend at least an hour choosing a girls and a boys name for your 'bump' and planning what their nursery will look like.

[Victoria85]

For one weekend you are a school girl, act that way and dress that way. But you were a naughty schoolgirl and got detention. Write 100 lines in a corner about what you should do better as a girl.

[supersusususus]

You shall go outside jogging while wearing a thong with a wedgie and a bra (Stuffed if you dare). Every five minute you will stop and bend over to stretch and reveal your thong for any people that may walk by. The jog must be at least 30 minutes.

[marystoy]

Wear a dark colored bra under a thin light colored shirt. Go for a 30 minute walk

[laraw]

You will wear nothing but a thong, hot pants, a stuffed sports bra and heels.

Go get a large ice from a public ice cream booth and walk the streets while licking you ice.

[mrskine30]

Roll a dice, this is the amount of womens clothes you have to wear for the weekend.

[Silicon]

Take a drive to some secluded place and change into girly clothes.
Put yout regular clothes in a bag and lock it with a padlock.
Have 2 similar looking keys* where only one of them fits the padlock.
Drive to another slightly less secluded place.
Throw one of those keys out of the car while driving.
Now you've got a couple of possibilities:
-the remaining key fits the lock and you may redress in the slightly less secluded place,
-the key doesn't fit and you return home looking fabulous,
-the key doesn't fit and you return home naked,
-the key doesn't fit and you go look for the other key looking fabulous...

*If you can tell the keys apart, put them into an envelope or sock. This way the lost key might be easier to find.

[laraw]

Wait until its dark outside or you feel safe. You will wear your pantyhoses, the swimsuit and the heels. Put on lipstick and nail polish. You are to either ding-dong ditch 2 family houses in your neighborhood(it only counts if someone opens the door) or you have to walk 4 km.

[laraw]

Bump, please make it a challenging one for this weekend.

[GumdropGirlyboy]

Let's see if I can help with a weekend challenge... Let's plan a nite out. Take a nice long shower and get your body clean, soft and smooth (be sure to give yourself a good scrubbing all over so all your skin is nicely sensitive) and lotion up from neck to toes. Then let's cover some of your 'pain' likes: use nipple clamps, aligator clips or clothespins on each of your nipples, and if you have a chain to connect them to your penis somehow that would be a bit plus. Now, breastforms over the nipples and a bra (1 size too small if you have one) and tuck yourself away between your legs under your panties. (if you have a latex suit you wish to wear under your bra and panties that's cool but be sure to have access to your bare ass). Now finish getting dressed in short skirt/top or mini-dress, heels, wig, makeup, and become as girlish as you can. Now take your favorite dildo, handcuffs and some rope and go for a drive (or long walk if you dont drive) some distance from home (I love dice rolls for time or distance but best if you determine limits yourself) Find a place where you can walk some distance from your car if you drove. Roll the dice again for the number of paces you'll walk from your car before you look for a place where you can sit (maybe a park bench or something). Sit and tie your ankles together leaving about 1 foot of rope dangling. Slide your dildo in and position yourself sitting with it buried deep inside you. Now tie the end of the rope from your ankles around the chain of your handcuffs. You can place the key wherever you feel comfortable but I'd say either under the dildo so you have to struggle to pull your legs and hands up to reach it, or maybe just under your feet. Now rock and squirm so the dildo slides in and out. If you can continue till orgasm that would be awesome. Otherwise, you can pick a time limit that you can handle before getting the key and releasing yourself, but if you don't cum while riding your dildo, once you are free of the handcuffs, you must rub your boy-clitty thru your panties until you pump your wetness all over yourself. Only then can you remove the dildo and ankles and return home. If you like this one and want a bit more challenge, do everything one nite but record all the dice rolls (or however you decide to determine times and distance) and do everything again the next nite, but double all of the numbers and require yourself to cum twice in your panties before release and return. Let me know if you like and how it goes if you do.

[Buzz9572]

Your going to be a maid for a day. Make sure to wear some nice white stockings and the locked on heels with you maids outfit. Wake up early in the morning prepare breakfast. After that do the laundry for your household. Make sure to iron everything that can take it. At midday prepare nice warm meal. After wards clean all your windows and be thorough. Now vacuum the house. During the evening prepare a little meal, to finish of your day clean every inch of your bathroom. As maids don't belong in the master bedroom, sleep somewhere else on the floor with nothing but a pillow and a thin blanket. You can change out of the outfit the next morning.

[Two kinds]

You must dress act and be a girl for a day, this mean using The women's bathroom and everything

I have no limits so make mine fun and crazy ;)

[prettypink]

You must dress act and be a girl for a day, this mean using The women's bathroom and everything

I have no limits so make mine fun and crazy ;)

Put an ad on craigslist for cleaning services. You must accept at least one cleaning request and turn up fully dressed as a french maid

[ZoLinko]

Go fully crossdressed to the mall and go shopping for female clothes.

[Victoria85]

Dress up in your sluttiest outfit and go to a bar. There try to pick up some men who are allowed to fully use you

[Calcifer]

I love your large collection of clothing (: It's a little difficult to give you a good outfit without knowing more about what everything looks like, but here goes. You've got plenty of red, white, and blue so let's make you wear that!

Wear your red heels, blue skirt, and white shirt. For underwear, your white push-up bra should be good, along with your cutest white panties (or diapers, if you'd prefer them). If your bra isn't made to fit you, then stuff it as needed. Do you have makeup? Red lipstick to match your shoes would be great, as well as some blush and maybe some eye makeup. Matching nail polish too, if you have it. A red belt would perfect the outfit, but I don't expect you to have one. Pictures are welcome (:

Now that you look the part, it's time to act like it. Get one of your dildos, preferably the large one if it'll fit in your ass without too much preparation (I forgot to say this, but you might want to do an enema to wash your ass out before this). Like I said, this cock is going in your ass, so you ought to be a good girl and lube him up first. Place it on the ground, or hold it against a wall. You're going to give that dick a nice blowjob for 10 minutes. Deepthroat the cock at least twice per minute, and each time hold it as long as you can. Imagine that this is an attractive man, and he just let a slutty sissy like you suck his cock. Thank him for letting you suck his cock with your mouth, and beg him to let you ride his cock with your ass.

Now that you've got that cock nice and wet, it's time to introduce him to your pretty little girly asshole. Remove your panties from under your dress, and hold that cock on the ground, pointing up. Sit on it to get it in your ass, and then ride it for 15 minutes. You can start off slow, but you should be pumping it real fast by the end. Just before you finish, beg "him" to cum in your ass, and moan loudly as you imagine his hot load of cum pouring out inside of you.

Thank him for cumming in your ass, and tell him how much you loved having his big dick in your ass. Now, be a good slut and suck his cock clean. You don't have to do this, but a good girl cleans off her Sir's cock when he's done with her (this is why it's important to do an enema before you start). Oh, and if you came from being fucked in the ass, be sure to eat it all up.

[Victoria85]

Sorry that you are not getting a long dare like you deserve, but you need more female clothing.

So put on your nail polish and your panties, watch yourself for 15 minutes in the mirror like that and start some shopping after that. Online / offline, that is up to you. But every 30 minutes you should at least study yourself for 1 minute again and think about what you need/want.

[hunter]

So you can wear your pink swimsuit, and paint your nails to match if you can, then put on your school girl outfit. You can then get your biggest dildo and place it on a chair, you must then ride the dick for 15 minutes at your own pace. Then you'll have to write lines like a naughty school girl quoting "I will always take sir's big dick" 1000 times after every line you must fuck the dildo as hard as you can for 1 minute before writing the next one

Enjoy! Let me know how it went if you want

[andiman]

Go to a costume shop and take pictures in some costumes (if they don't have it, find something that is the closest):

Princess
School Girl
French Maid
Cheerleader
Fairy

[rogue_9]

Dress up as a girl the best you can and take an hour-long walk in the woods.

As a note, you should have an entry that lets everyone know what crossdressing clothes you have. Makes it easier to give you dares.

[Victoria85]

Go out for a stroll and nod to every guy you see. You can't come home till you either got a compliment from 5 guys or a kiss from one.

To do this you must be wearing a sexy dress, high heels and do your best to look as smoking hot as possible.

[andiman]

I dare you to dress up in a g-string, bra, tanktop, and the shortest shorts you can find. Give your self a bra-conection wedgie. Now do a workout dare of your choice. Keep the wedgie in 10 minutes after the duration of the dare.

[DJJ90]

Put on a bikini and heels. Fill two balloons with ice-cold water and use them as breasts. After ten minutes, lie on your back and pop the baloons

[SissyTim]

Wear big stuffed bra and panties next weekend

[VRz]

Wear a pink bra and stuff it with water balloons and wear a white shirt and pants and stay like this for at least 6 hours

[Dark_light30]

Wear your maid outfit next time you go to the store.

I only have unde garments

[Buzz9572]

wear panties for a month. No guy underwear allowed till the month is done.

[sissybeach]

wear panties, bra and stockings for a month no guy clothing allowed taste of your own medicine ;)

[Victoria85]

First off fix your link (http missing : ;)

You have to go out wearing female lingerie and go shopping, buy at least a female dress, but not before trying it on in the store

[noob37]

You are to get fully cross dressed, then cum on a piece of bread which you will use to make a peanut butter and cum sandwich. Then enjoy your sandwich.
I will be going shopping later so nothing to against my limits.

[VRz]

Wear a dress wig stuffed bra panties and and make-up

[naughty_uk_20s]

You must go on ebay and bid for at least 10 different items (you can bid low if you want), but they must be completely different. E.g. it can't be two skirts, even if they are different.

You must be crossdressed completely before you bid and must not get undressed untill all items have had their bidding ended. If you win any, you must buy it.

PM me for an outfit if you would like.

[Silicon]

Dress like an anime character (short skirt etc.) - but with a tail (plug) and cat/fox ears.
Take a long walk like that. (May be at night)

[prettypink]

Every day for the next week put a very short tight dress, stockings or pantyhose and a bra and panties on under your normal clothes and everywhere you go carry a bag with a pair of 6 inch heels in it.

When you are alone and not at home or when it is safe to do so you may take off your outer clothes and put the heels on. You must do this for a total of 30 minutes every day (they don't have to be continuous you can add up 2 minutes here and there).

[laraw]

Put on a gag, nail polish and a stuffed bra. Put on a nice dress and heels. Stay like this for the rest of the day and watch some girly shows.

[Einstienium99]

Wear a leotard or one piece swimsuit under your clothes for a week. Must show someone at least once over the course of the week.

[matty8567]

you must wear panties and a pair of tights under your clothes for the next two weeks.

[GumdropGirlyboy]

Visit public restroom anytime you're out shopping or whatever and completely undress to use the toilet (or if you're using a urinal you must drop your pants and underwear to your ankles)

[andiman]

wear your (stuffed) bra, panty, stockings and a blouse out for 15 min walk.
Masturbate 2 times while doing so. And when you get back home cum in your pantys and wear them for the rest of the day.

[magnick]

Start the new year in fem undies. Wear stuffed bra, panties and tights for the whole night.

[chrs]

Start the new year wearing a tight dress or skirt and stockings, no panties or pantyhose. you have to put a dildo in your butt and are not allowed to hold it in with your hands, when it drops out give it a passionante kiss and put it back in. you may remove it after 1am jan 1

[hunter]

Well lucky for you, you get to go out NYE dressed as a girl. Mini dress panties stockings and heels! Remember till home do you part (with your heels or clothes)

[chrs]

public is a limit ....

[hunter]

Have fun staying at home then

[Sissyboy705]

Wear panties with a mini skirt

[Sissy Trisha]

Put on lipstick and go to store - buy anything

[Victoria85]

No likes/limits and giving small dares hmm
Wear a bra at least three days a week for the next year

[greatspanker]

you have to go commando in mini skirt for 50 hours in the next 14 days in public

[hunter]

So happy NYE for you, hopefully not much planned because you have to spend it dressed as a slutty school girl from 23:00 to 01:00 must make sure your make up is on point too and spend some alone time with yourself towards the end like good girls do

[prettypink]

Go to your favorite semi public place, put on your pvc dress and lock your heels to your feet. Yell out Happy New Year as loud as you can and change your clothes back before anyone sees you.

If you want to make it harder Cuff your hands behind you and leave the keys for cuffs and shoes at least 30 feet away from you in opposite directions.

[laraw]

You got to wear white lingerie including a stuffed bra, panties, garter belt and stockings and some black high heels for this. Clear the floor in one or multiple adjacent rooms and hide a release in one end. Go to the other and hogtie yourself. Include a gag and a blindfold if you like. Also hide the the release somewhere where you might get exposed if you enjoy such a thrill.

Make sure you get someone to check on you in case you can't free yourself. And play safe.

[UsedBoy18]

wear women's underwear for a week, or a dress for one hour (in public)

[SissyCrossCum]

Wear high heels everytime you're at home for one week, or walk with them for 1 hour in public. (You can be crossdressed if you think it could pass better in public)

[Sissyslut591]

Give yourself a bra connection wedgie and go out in public

[SissyTim]

Wear just a thong and a bra. Now walk around the outside of your house for 15 minutes

[laraw]

Your going to be a maid for a day. Make sure to wear some nice white stockings and the locked on heels with you maids outfit. Wake up early in the morning prepare breakfast. After that do the laundry for your household. Make sure to iron everything that can take it. At midday prepare nice warm meal. After wards clean all your windows and be thorough. Now vacuum the house. During the evening prepare a little meal, to finish of your day clean every inch of your bathroom. As maids don't belong in the master bedroom, sleep somewhere else on the floor with nothing but a pillow and a thin blanket. You can change out of the outfit the next morning.

[sissyfitz]

Gutted :( Wish I had gotten the above, ah well.

Black Bra
Black Thong
Long white skirt
White Pantihose
10" heels
Black corset over dress

Send me a picture if you are comfortable with this.

[SissyTim]

For the next week, you are to act like a girl whenever you are alone. Apply heavy make up every morning, wear stuffed bra, nail polish etc. Wear you frillyst clothes all the time you are home.

[Carstein]

Glue a pair of stockings and suspenders to your skin and wear them under your normal clothes until the glue wears off

[Itchynugat]

Get tarted up for clubbing in a short dress, makeup, and heels. Then, dance as sexy as you can for one an hour of floor time. You can takes breaks as needed, but break time doesn't count against dance time, and during dance time your ass is Moving!

[>Sam]

You have a choice,
Either you must dress up in a maid costume and clean your shower using your toothbrush,
Or you must dress up as a female, hot, plumber and pretend you need to fix your shower!

[dgaz]

You should wear panties everyday and keep your toenails painted bright pink for 5 days

[Victoria85]

You have to wear a bra for a full week, no taking off for anything.

[prettypink]

Dress like your avatar but with your highest heels and tie yourself to a chair for an hour

[marystoy]

Wear thong panties for one week, no excuses!

[Victoria85]

Go for a walk in your most xtreme clothing for 15 minutes

[Blue Griffin]

Get crossdressed in your favorite outfit and get into your favorite bondage position on your bed. Stay like that for die roll x 10 minutes.

[Einstienium99]

Wear a tight crossdressing outfit and go outside for 10 minutes

[SissyTim]

Wear your leotard and do this (https://www.youtube.com/watch?v=E40tZSMaEoQ) workout.

[wedgieslave62]

Wear any type of panties u want preferably something pink and a pair of shorts over them the looser the better now go out for a walk in the park and every 10 feet pick up a decent sized rock and pUT it in ur pocket do this for 30 minutes each time ur pants fall u must do 10 jumping Jacks b4 pulling them back up

[wedgieslave62]

Bump bump usually don't like doing this but it's been a few days

[Nimina]

Wear a thong (whale tailed) with a shirt that perfectly reaches where the waist of your pants are. Go to your local supermarket and make sure you reach for a few things on the top shelf and bend over for a few things on the bottom shelf.
Make sure at least one person is in the same aisle as you while you do this (although they can be looking at something and therefore distracted).

[Blue Griffin]

Wear thongs until you have completely transitioned.

[PrincessHannelie]

dress up as similar as possiblelike little girl. roll a dice:
stay X * 10 min. like that..

i like dressing as princess.

[Thomps4991]

Dress as a princess and stay like that for the whole day

[Adi-Row1]

Put on dress and thong, and tie yourself up however you want

[Jacob69]

Where a different girls outfit each day for a week (how long u wear it is up to you) but u must send me a pic of u each day in your outfit
Kik jacob_fredson69

[marystoy]

You must wear pantyhose for the next week.

[wedgieslave62]

Wear bra anf panties(preferably bright colored) under a white tshirt and shorts that areally a size too big and go to the mall to buy some clothes make sure u try them all on in the changing room with the door unlocked

[wedgieslave62]

Usually dint like doing this but bump

[janesg]

Put yourself in a bra connection wedgie under your normal clothes for an hour, spend at least 10 minutes of that time outdoors

[topryan]

Wear a stuffed bra and thong for 2 days in public

[snowpro2000]

use a tampon in your butt, and wear panties over it for atleast 2 hours.

[wedgieslave62]

Get completely cross dressed and tie ur ankles and wrists together until u pee ur self

[sizi]

Dress like a balerina or a gymnist for the day. Put on a tutu or a leotard, tights, slippers or some really girly shoes. Put on the girliest and most revealing pair of underwaer u can find under the leotard/tutu or go commando. Every 30 mins you must do a ballerina or do a gymnastics performance to a girl band song of your choosing

[marystoy]

Wear a bra and panties 24 hours a day for two weeks. When alonedd heels.

[SlutAmanda]

Watch a chick flick while giving a blowjob to any phallic object.

[hunter]

Watch a full length porn film whist dressed in heels, stockings, mini skirt and bra with a dildo or similar up your bum and with a gag in your mouth, you must also while the film in on be tied on you bed hog tied until the end of the film. You can only undress after watching another 3 films over 2 hours long of your choice

[SissyMattison]

Get crossdressed in your sluttiest outfit with makeup to match. Get a dildo and watch a full length porn film copping everything the woman does

[marystoy]

Wear the sluttiest outfit you have and dance for 15 minutes in front of a window where you could be seen.

[marystoy]

Bump, bump, bumpity bump

[supersusususus]

https://www.google.se/search?q=prostitute&source=lnms&tbm=isch&sa=X&ved=0ahUKEwiVi7DS95vPAhWJYZoKHY_IDigQ_AUICCgB&biw=1366&bih=662#imgrc=330wspXIvnTFcM%3A

Get dressed up in an outfit like one of the two in the picture above, if you don't have the clothes, buy them in a local store during the day. Then at night you get fully dressed up with makeup and your new outfit and go out and walk along the streets. If someone mistakes you for a whore and wants to buy sex, it's up to you what you do! Good luck and be safe! :)

[Bobcat]

http://pictures.4ever.eu/tag/5242/prostitute

stand on a main Connor for 20 min

[PrincessHannelie]

lets revive this.

you will be a girl for two days whenver you are at hime alone.

[GumdropGirlyboy]

Just hoping to breathe a bit of life into this thread. Semi-public and no mess for me please

[PrincessHannelie]

okay, so just wear femal underwear a day long.
and next time try to give me a dare.

[JohnSmith56561]

wear a onepiece swimsuit under your clothes for 2 days and even shower with it on

[SissyTim]

Wear your pink fishnet bodysuit for 24 hours.

[ThongSissy]

Wear a white tee shirt with a pink bra under it and buy some lube.

[andiman]

Take a panty and a bra and stuff it.
Wear your boy clothes over it and go for a walk.
On the half way wear a lipstick of your choice tonally back.

[supersusususus]

Roll A dice, the number you get decides hos many articles of Female clothing you Will Wear while walking to the store to buy a carrot. You may cover your sissy clothing however you want, e.g. Jacket ovet the Female top IF you roll 4.

1: panties
2: 1 + bra
3: 2 + stuffed bra
4: 3 + Female top
5: 4+ leggings
6: fully crossdressed

When you return home you Will blow your carrot and cum on IT while Only wearing your sissy clothes. After that you Will lick IT clean and roll the dice Again, 1-3 means you re-do the dare tomorrow, 4-6 means you're free.

[Darkmark]

Dress as a maid and clean your house from top to bottom.

[wedgied]

Wear tights everyday for the next 2 weeks.

[raynacd]

weara dress and go for a walk

[hunter]

Wear full makeup and then wear a bikini and heels for the next 48 hours

[andiman]

wear a bra, panty and stockings for 1 week under your clothes.
When you are at home you can only wear girls clothes or stay nude.

[ark_nekko]

For the next week you have to wear/do the following

Instead of male boxers, you are to wear panties.
Paint your toe nails any girly color.
When alone, you must add a bra and a girly top, and also try to work on your feminine voice.

These things don't seem difficult to do. But after a couple of days it can get to you. I wish you the best of luck

[raynacd]

spend all alone time for a week crossdressed

[Victoria85]

You can't wear male underwear for a month

[chrs]

Dress up as a maid (panties, bra, stockings, uniform) and clean your house/flat with a butt plug in, moving up a size in every new room then cum on the floor and lap it up

[JNoller]

Whenever you are out, you must have panties on. If you are wear pants, wear leggings as well. This is one month

[ark_nekko]

I dare you to buy eyeliner and mascara at a store, and wear it every day until it runs out.

I would like mine to involve taking a picture

[Born2BaSissy]

Wear a bikini, heels and fisnets, very heavy makeup and what you consider the sexiest wig. Go for a walk in a crowded place until you get someone twice your age to take a picture of you with their phone.

[Born2BaSissy]

Bumping the thread. How mean can you be?

[Shuol]

I dare you some posture training.

Put on panties, a butt plug, and high heels and go for a 15 mins walk. You must walk like fashion models do.

[ark_nekko]

Use tape to tuck your balls and dick away. After that get dressed in panties, the tightest girly jeans, a bra and a fitted male shirt.

From there I dare you to drink 2 liters of liquid, and go 6 hrs with out having to pee/un tuck

[PrincessHannelie]

you will be fake pregnant for a day. and you will dress as girly as possible. tutus, pink dresses, braids :)

[PrincessHannelie]

lets revive this. my post still counts.

[wheelsoffeathers]

Plan a fake wedding for youself while wearing your Wedding gown & bridal crown+veil

[sissysubbb]

Dress as a schoolgirl and do your homework which is watching a slutty makeup tutorial and following it

[kycats]

You may either
A: Get dressed in your favorite outfit and full makeup and watch/listen to sissy hypnos for 4 hours.
or...
B: Go to a department store like forever 21 and find someone willing to pick an item of women's clothing out for you. Buy whatever they choose if it isn't too expensive.

Public dare for me please

[Feminizedboi]

Wear your sexiest outfit. Put on full makeup but do it badly. Go to your favotite cosmetic counter and ask the lady for any products/suggestions to improve your look.

[hunter]

put on your tightest outfit then lock that on you and freeze the keys, youre not allowed to let the keys start to melt for 24 hours

[Feminizedboi]

For 3 days, when you are home you must be in heels, micro dress (or micro skirt and crop top) and red lipstick.

[Feminizedboi]

Bumping the thread.

[Feminizedboi]

So this is dead. 😞

[Twill]

Go to the mall. Wear tight fitting jeans, a white top, and a white bra. Get a makeup artist to apply mascara. You may walk around with a jacket, but while you're getting your makeup done, you must remove your jacket.

You must send me separate photos of your outfit, and a closeup of your makeup-ed eyes (no need for full face).

[hellothere]

Put on a thong and bra in a bra connection wedgie for 24 hours.

[hellothere]

Bump bump bumping

[welshdresser]

Wearing bra and knickers under your normal clothes, go to a clothing store and try on some trousers and a t shirt in the changing rooms. Come out and check yourself in the mirror if you dare. Bonus kudos if you go to a shop that sells male and female clothes and you try on a skirt and top. PM me with whatever you do.

[subaddict5]

put on thong panties, bra (preferably stuffed). Put some nettles in the front. you may not remove the nettles until you have cleaned your entire house/flat in your most feminine dress.

[Sabina]

I am think about sexy sissy and good punish for you to sleep tonite in bed.

Dress in red garterbelt and stocking better if heve fishnets, no panties but bra with DDD fake tits. Underbust corset try stict to tie.
Add miniskirt a slutty one you chose and crop top. Heeled pump shoes to bed all long of the nite. Best with straps around ankle if heve.
This was the easy part dear Chloe! Make not illusion.

Now some bondage: metal or posture collar, not want you choke or strangle but must for you to be not comfort. Big must hold if all nite. Choose carefully this passage.
Becouse you tie to it with rope the metal anal hook and pull good the rope that you feel if all inside.
You tie ankles crossed, put drool gag or ring gag and put the biggest dildo between fake tits and imagine you give Tithonus becouse like the sluts when do it.
For better nite, tie wrists behind back yourself and allow only you hump pillow,
Yes to edge at lest 3 time
No to orgasm. For sure no!!!

Good nite Chloe, not stain with lipstick or make up or cum the pillow in the your bed

[Sabina]

Gently bump it.
Plese not make regret me of doing!

[Spacepieeater]

lets start with black lace bra and thong. the the bra stuffed sized DD then over top that black cupless corset with suspenders with them addict to the black stayups with lace top. black stretch female T-shirt with the pink miniskirt. then add Black super high sandals thin ankle straps. 16cm heel and 4cm platform.
because you gave bondage here your: start with metal large ring gag 5,2cm with black straps. then add the large cone black 12 x 5,3 cm (3 at thin point). then make your legs into into a mermaid tail. then tape one hand about your head so your standing. stay up there for a hour.

[jackjac]

Fully crossdressed make up and all edge 5 times finger yourself for 5 minutes edge five more times then ruin an orgasm before rubing in on your face and in your hair no washing until you've managed to cum again through anal

[andiman]

Roll a die:

1 - Panties
2 - 1 + Bra
3 - 2 + Skirt
4 - 2 + Dress
5 - 4 + Stockings
6 - 5 + Make up

Roll a die and multiply it by 10, you must stay like this for x amount of minutes.

[ExhibCouple]

Here's one I did.

Put on stockings under your pants.
Put a skirt and heels in a bag and put them in the trunk.
Go for a drive and find a place where you can get out and trade your pants for the skirt and heels.
Lock your pants in the trunk
Go for a drive until you can find a place to change back into your pants.
The longer the drive the better.

I've done this where I've locked the heels on my feet and need to drive to a location and retrieve the key before I can remove them.

[Sismaster]

Dress in a bra and thong. Make sure the thong is nice and high up you bottom. Stuff your bra with the biggest water balloons you can fit in them. Now it's time to do some exercises. 10 press ups 20 sit ups and 30 star jumps. Everytime a balloon falls out you have to add 10 more of that exercise. If you pop a balloon you have to replace it, spank your bottom 10 times and then carry on.

[andiman]

lay out a nice set of Pink womens underwear (bra,thong,slip and maybe corset). then a pair of shorts that are loose and a white t shirt. Dip the white t shirt in water so it becomes slightly transparent and put it on. Now put the shorts on but make them sit low on your waist. Then go for a run.
Just go somewhere you have a chance of being seen and stay there for 10 mins.

[andiman]

bumping this... :)

[hellothere]

Put on a bra, panties, and a dress then take a ride to a fast food restaurant. Order two burgers and place one in each bra cup. Drive around for at least 30 minutes before heading home.

[Daddy09800]

Complete this dice dare

https://www.getdare.com/bbs/showthread.php?t=48384

[thehyte]

Go to a clothing shop and buy panties & stockings. After buying them put them on right away (eg. public toilet) and don't take them off until the next morning.


Would love to get some like this (night drive & walk), feel free to add anal/bondage/...

Here's one I did.

Put on stockings under your pants.
Put a skirt and heels in a bag and put them in the trunk.
Go for a drive and find a place where you can get out and trade your pants for the skirt and heels.
Lock your pants in the trunk
Go for a drive until you can find a place to change back into your pants.
The longer the drive the better.

I've done this where I've locked the heels on my feet and need to drive to a location and retrieve the key before I can remove them.

[andiman]

wear nice womens underwear under normal clothes, go for a walk, with some heels in a bag, go to a forest or other quiet place, then strip down to ur girls clothes, put ur heels on and put ur normal clothes in the bag. Leave the bag with ur clothes in where you are, and walk away.
see how far u dare to walk away from ur bag before running back

[Appelt685]

Go buy panties and a mini skirt and change into them in the bathroom

[EnigmaticBunni]

go to a public washroom with a female outfit in your backpack. once there change into the outfit and take 3 selfies and send each one to 3 people on here or kik. (so 9 messages in total) before changing

[subaddict5]

Dress up as slutty you can, then make out with yourself in the miror for 5 minuites. Then edge, and remove one arricle of clothing, then make out with the mirror agiain and edge and remove until you are left with only underwear. You may then cum. If you cum before you are fully naked (except underwear) you must lick it up and start over from the very beggining.

[Sophiehogt]

Paint your nails (at least toes), wear women's underwear for the next week, and each day you must wear some form of women's clothing that is somewhat embarrassing, but only when home.

[Mr.sissyboy]

Dress up fully as a girl with makeup, nails (if you want), underwear and a dress and go somewhere in public where you’re hidden and take a picture. Keep it as your screen saver for the next 2 days.

[andiman]

For the next 3 days you must wear bra, panties and nude pantyhose or leggings you can hide them under regular stuff but you can't take them off!

[andiman]

A little bump...

[HerewegoII]

For the coming month, at home you will only wear female clothes, a wig and make up.

[PantyhoseLover]

for the next 3 days you have to sleep in your sluttiest outfit.

[andiman]

black panties, suspenders, stockings and bra under your work clothes for a week

[sissyxresser]

For the next month you will be wearing panties pantyhose and bra under your clothes when driving you will be in in high heels as well. No male underwear and no socks when home you will be in dress or skirt and high heels

[Sabina]

You heve 3 month from today, to prepare you mentally and phisiclly for go put complete en femme one day and shopping in store for shoes and for dresses and blend in like women
It inclusive also drive car dressed and with high heels on.

Write good report of the day in blog or your one new thread if preferre

[Sabina]

Bumpy bump this one

[hellothere]

Before you start you must get a lock and key if you don’t have one already. Place the key in your backyard in the furthest corner. Put on a bra and thong with pantyhose over top of that. Put on a dress and fasten a belt around your waist so that you can’t take the dress off. Fasten the lock on the belt so that you are stuck until you retrieve the key from the back yard to unlock yourself.

[MrPaul]

Fill up a bath wit moderately cold water. Enough to be uncomfortable. Then insert something anally, and dress up in some girls clothes you don't mind getting wet. Then tie your ankles and thight together and your hands together infront of you so that you can get out of the tub when the time is up. After 15 minutes you may get out only if you have pissed in the tub and came twice.

[hail]

Take a panty and a bra and stuff it.
Wear your boy clothes over it and go for a walk.
On the half way wear a lipstick of your choice tonally back.

[hellothere]

Go to a store and purchase a new pair of panties. Once you pay for them, head to the restroom and put your new panties on before heading home. Keep your new panties on for at least 24 hours.

[hellothere]

Put on a stuffed bra, panties, stockings, and a dress and walk out into your backyard during the day. Walk out a minimum of 25 feet beyond your door.

[Dutchvirgin1995]

Lock all your male clothes away and put the key in a timed lock box. Have the box locked the entire weekend. Enjoy wearing girly clothes all weekend!

[hellothere]

Wear a panties and a bra under your normal clothes for 24 hours.

[Sabina]

Wear a panties and a bra under your normal clothes for 24 hours.

Why you not do exactly the same, but add nylon stay up stockings and even garterbelt, and no covering with normal socks
If you very daring, not sheer nylon, but fishnets which is more difficult to cover

[KEDA]

You're gonna be stuck as a sissy. Get yourself a lock of some kind. A padlock would be great. Now you can do this with multiple kinds of clothing. I recommend high heels with a strap that you can lock together, a corset, or female pants that you can lock together. After locking your clothes on, throw the keys of your little lock randomly in your front garden, and good luck finding them!

[Lotoloto]

You should wear a thong wedgie that can be seen for a week

[Lotoloto]

Pushing this thread

[hellothere]

Wear a Bra-connection wedge to sleep tonight.

[hellothere]

Bumping this thread.

[hellothere]

Bumping the thread again.