199 Sissy Tasks

[play safe, sane and consensual]

March 2024 – Ver. 2.0

2. Wear Panties for 24 hours.

3. Shave your from your neck and down.

4. Make a text post online (Blog, Reddit, X etc.) describing a task you have completed.

5. Post a dressed selfie to (Blog, Reddit, X etc.) (bra, panties, makeup and wig).

6. Wear nipple clamps out in public.

7. Wear a wig in public

8. Swallow two loads of own cum at the same time.

9. Edge once every five minutes for 1 hour.

10. Drink a glass of soy milk.

11. Create a Chaturbate account (or similar), and show some of your body.

12. Jerk off a Real Cock.

13. Suck off a suction cup dildo on your knees.

14. Leave a complimentary comment on a dick picture online.

15. Paint your toenails.

16. Give yourself a face full of cum (in yoga plow position).

17. Download Grindr (use a photo of yourself as a profile picture).

18. Squat once per 10 seconds for 5 minute (naked).

19. Wear a bra in public (under your shirt).

20. Vibrate yourself to orgasm with a Magic Wand.

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21. Make a Pornhub account, and make a public list of preferred Sissy videos.

22. Watch Sissy Hypno for at least 10 minutes 3 days in a row .

23. Wear Heels.

24. Swallow one load of your own cum

25. Create a sissy caption and post online.

26. Wear a Chastity Cage for 24 hours.

27. Make a Fetlife Account.

28. Paint your fingernails.

29. Do Yoga in tights.

30. Cum on a food item and eat it.

31. Suck a dildo, constantly pushing your limit (train your gag relex).

32. Complete an Achievement on Pornhub.

33. Practice Talking in a girly voice.

34. Wear a collar.

35. Put a buttplug in your ass.

36. Finger your ass, and lick your finger clean.

37. Wear light makeup in public.

38. Fuck a dildo, use a sucktion cup dildo.

39. Cam on Chaturbate or similar (panties, bra, and wig minimum).

40. Make a Reddit Account

41. Get a Facial from a Real Cock.

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42. Post a picture using a sex toy to a Blog, Fetlife, Reddit, X etc.

43. Shave pubic area.

44. Apply three squirts of Female Perfume.

45. Shave your legs.

46. Have a girl tell you that you have a small cock.

47. Perform an enema.

48. Put on girly deodorant, before you are going to the gym or other sport.

49. Spank your ass 30 times each cheek

50. Buy breast implants.

51. Get gangbanged by three or more men.

52. Get a sissy tattoo and wear it for 48 hours.

53. Shoot Professional Porn.

54. Perform a sexual act with a Real Cock over 7in

55. Get three or more facials at same time from Real Cocks.

56. Photos or video of you being Gangbanged by three men.

57. Tell a friend or family member you are a Sissy.

58. Eat cum from a pussy creampied by a Real Cock.

59. Suck yourself until you cum.

60. Eat a pussy while it is being fucked by a Real Cock.

61. Let a fuck machine pound your ass (60bpm minimum).

62. Go ass to mouth 25 times with a dildo

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63. Go 24 hours without an erection (no chastity allowed).

64. Facefuck a dildo (80 bpm minimum)

65. Swallow more than three loads of own cum at same time.

66. Watch a Real Cock fuck a woman while in chastity.

67. Tell a colleague you are a sissy.

68. Earn more than $50 camming on Chaturbate or similar in one session.

69. Get Pegged.

70. Perform a blowjob on a Real Cock with another sissy or woman.

71. Get Spitroasted by Two Real Cocks

72. Wear heavy makeup.

73. Go outside fully dressed (girly top, girly bottom, panties, bra, and wig minimum).

74. Deepthroat dildo every ten seconds for 3 minutes.

75. Tan with a bikini on.

76. Fuck a Real Cock.

77. Grow hair to shoulder length.

78. Tell a female friend you are a sissy

79. Suck a Real Cock.

80. Suck a Strap-on.

81. Post a Video on PornHub (1 minute minimum).

82. Swallow a load from a Real Cock.

83. Verify your Chaturbate (or similar) Account.

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84. Verify your Pornhub Account.

85. Create a sissy hypno video and post on Pornhub (1 minutes minimum)

86. Take a supplement made for a woman (ex. butt enhancing, estrogen promoting, etc)

87. Pluck Eyebrows.

88. Have a Sissygasm.

89. Give a blowjob to a stranger at a glory hole (use condom)

90. Drip fake cum on your face to make it look like you got a facial. Let it dry and don’t clean it

off for at least 3 hours (or until someone has seen you—whichever comes first).

91. Dress as slutty as you can (full makeup) and talk with at least 3 people.

92. Line up your dildos and plugs from small to Bad Dragon. Starting with the smallest and

working up, use each item to fuck your ass for at least 2 minutes each. Finish with the

Dragon and record how deep you get it into your ass.

93. Each time you need to pee, use a different room and receptacle. Some suggestions: on all

fours onto a towel, in the shower, into a glass, outside or on a balcony into a bowl…

94. Spend the evening on all fours like a good piggy. If you have a suction cup dildo, attach it to

a wall and fuck it every hour on the hour for 5 minutes. That’s the only time you’re allowed

to cum. In between it’s edging and if you need to pee it’s on all fours.

95. When you’re ready to cum, open the window and cum loudly near it. Make sure the

curtains are open.

96. See what you can trade sex for (anything but money).

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97. Open the curtains wide and crack the window. Get on all fours fairing away from the

window (so your ass is facing it). Cum loudly at least once there (more the better).

98. Free Use - put yourself out there and don’t say no to anything (safety first!)

99. Extreme hookups - try to hook up with guys with the biggest and smallest cocks, shortest

and tallest guys, super vanilla and super kinky

100. Go full femme: hair, makeup, clothing, underwear then make and post a video of yourself

doing a sexy striptease (wearing a lace mask).

101. Send some non-face nudes to a random person.

102. Try these for a week each: no touch, edges only, anal only, cum only away from home

103. Get a remote control vibe and let someone else control it while you’re in public

104. Only allowed to touch yourself with pictures of feet / feet porn. If you watch other porn,

you must stop touching yourself immediately and switch to something that repulses you.

105. Drink two large glasses of water, then edge.

106. Wearing jeans, wet yourself away from your home.

107. Wear blue jeans or grey track suit bottoms (light colours will show more btw). Then drink a

large glass of water/liquid. Wait 30 minutes and go somewhere public and wet yourself.

Then walk back to your car/house.

108. Not use the toilet to pee for a full day. Pee in the shower, sink, a bowl, outside, etc. instead.

109. Give yourself an orgasm in your car or a changing room.

110. Pee in a sink in a public restroom.

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111. Buy something in a drive thru and have your lower body exposed; cum in a cinema; play

with yourself under the table at a restaurant or bar.

112. See how much of the 16” dildo you can get inside you. Do your best at the start and end of

the week to see if you improved after a week of depravity.

113. Wear the shock buttplug whenever you’re outside the house (apart from work). Give

yourself a shock anytime you hear a number spoken.

114. Get naked in a wilderness area.

115. Cum in a cinema.

116. Go through a drive through with no pants

117. Put something massive into one of your holes—larger than you’ve ever done before.

118. Each time you go shopping, you need to buy at least one thing you could use in a sexy way

(to masturbate, use with a partner or wear). Post pics or descriptions of your purchases.

119. Make an audio recording telling what a whore you are. Cum on the recording.

120. Spill yogurt on your clothes. Wipe it off with a dry towel, then go somewhere in public. It’ll

look a lot like dried cum.

121. Purchase at least 5 items of various sizes that could be used for insertions—one of each

veg/fruit only. Carry them with you for your whole shop ideally in a clear bag or in plain

view as much as possible.

122. Wear a diaper all day without changing it. Go somewhere in public with it on before bed.

123. Get on Tinder and set it for all ages and genders. Meet up with the first person who you

match with and (safely!) make them cum. Nothing else, just an orgasm and go home.

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124. Get 5 vegetables of increasing size: carrot, cucumber, zucchini, etc. Use them in your ass

from small to large later. As a bonus, eat at least one afterwards.

125. Wear your collar. Each time you cum, write something on your skin. Start with “cumslut”

and “Sissy whore.”

126. Whenever you touch your small clit, make sure you have something in your ass or on your

nipples.

127. Dress in tight clothes and go for a run/walk. Drench your top with water before you go

out—no bra.

128. Fuck yourself with a banana, then eat it afterwards.

129. Make a salad and dip each piece of it in your ass before you eat it.

130. Piss yourself first thing in the morning and wear those clothes the rest of the day.

131. Lick all toys and fingers clean after use.

132. Dress provocatively when you leave the house with no bra/underwear when possible.

133. Always wear a day collar outside the house.

134. Offer men to give them a hand job. For humiliation, the price is $5.

135. Make a list of 10 little household jobs (wash dishes, vacuum, etc). Strip and complete each

job, pausing to tease yourself between each job. Don’t do anything else until those 10 jobs

are done. If you want more, play porn in the background or a Sissy hypnosis video while you

work.

136. Spend an hour on all fours—staying off the furniture. Place bowls of food (cereal is good)

and water on the floor. Put something on your neck as a collar. Be sure to put some doggy

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 toys on the floor. You can’t use your hands, but may grind to edge. If you’re really up for it,

pee at least once like a bitch on some papers or towels on the floor.

137. Attend your online class nude from the waist down.

138. Study for 6 x one hour blocks of time wearing a plug (take a 5-10 min break between

blocks). If you don’t put in a whole hour, edge wearing your clamps and apply tiger balm

before the next session.

139. Write 10 degrading names on your legs. I’ll give you a few to start: cumslut, pain whore,

fucktoy, cocksucker…

140. Wear a buttplug out somewhere in public under a skirt or dress (no panties).

141. Edge in each room of the house in a day.

142. Wear and use only diapers for 24 hours.

143. Body writing. Add one item on your body each hour from morning to bedtime.

144. Make a slutty audio recording, and post it online.

145. While working you must have WHORE, SLUT, or FREEUSE written on areas of your body the

laptop camera can see. If you are to have a zoom call that day, the writing still exists but

under your clothes. However some small amount of the letters must still be visible.

146. Wear a buttplug (size XL) for 4 hours. Then fuck your ass with a dildo (size XL) for 20

minutes. Keep going even if you cum.

147. Wear a buttplug (size L) for 1 day.

148. Cum from anal 2 times in 1 days. Use a dildo or prostate massager (size XL).

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149. Spend 14 days in chastity while wearing kinky underwear. You can cum only from anal and

you may not touch you penis (only when cleaning).

150. Spend 7 days in chastity while wearing kinky underwear. Wear at least one piece of clothing

(skirt/dress/pantyhose/stockings/heels etc) during the day for at least 4 hours (can be hidden

under clothes). You can cum only from anal. Make sure your crotch and armpits are shaved.

151. Spend 2 days in chastity while dressed like a girl - underwear, makeup, nails, wig (long hair)

and cute clothes. Cum from anal at least once. Make sure your whole body is shaved smooth.

152. For 14 days - edge 1 time every day. If you cum, add 7 days to your time

153. For 10 days - edge 2 times every day. Keep yourself in chastity for the rest of the time. If

you cum, add 5 days to your time.

154. For 7 days - edge 3 times a day. Keep yourself locked in chastity for the rest of the time. If

you cum, add 3 days to your time.

155. Hold a 1500ml enema (any liquid) for 15 minutes.

156. Take a 1000ml enema for 10 minutes and drink at least 200ml (10oz) of piss in the

meantime.

157. Fill an enema bag (container) with 600ml of piss and run the tube down to your mouth.

Slowly drink it all up. If you tie yourself and use a gag, you can go with just 400ml of piss.

158. Go in chat or online and request 10 lewd tasks to perform. Take photos/videos while

performing them and share them with the others.

159. Do a 1 hours live stream and perform any sex acts others request in chat (use a mask).

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160. Go outside and take a 30 minute walk wearing at least one of the following: fully dressed as

a girl or in latex / wearing a tail, animal ears and a collar / wearing chastity cage, a buttplug

and a small vibrator / wearing a rope harness, clothespins and cuffs.

161. Spitroast yourself for 30 minutes with two suction cup dildos (sizes L and XL)

162. Fuck yourself in the ass with a dildo (size XL) for 20 minutes. Leave it in and then give

another one (size L) a 15 minutes blowjob with at least 50 deepthroats.

163. Insert a dildo size XL in your ass and leave it in. Then deepthroat another one (size L) for 5

seconds - 15 times.

164. For a period of 1 days - wear animal ears, a collar and a tail. Drink and eat from a bowl on

the floor. Walk on all fours. Sleep in a cage. You may have four 30 minute rests.

165. For a period of 4 hours - wear animal ears, a collar and a buttplug tail and tie yourself in a

bitchsuit position.

166. Spread your sex toys or other objects (20 minimum) around your apartment so that they

could easily be reached by a toddler. Apply animal ears and a buttplug tail. Tie yourself in a

bitchsuit position. Start collecting your toys one by one by bringing them to a common place

with your mouth. You are done when all the toys have been gathered at one place. You have 3

hours.

167. Wear four pieces of fetish clothing or a catsuit for 1 day.

168. Wear a full catsuit (bodysuit) made of out latex/leather/pvc or vinyl for 12 hours.

169. Wear a full catsuit (bodysuit) made out of latex/leather/pvc or vinyl and a gas mask for 6

hours.

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170. Insert a 8.5mm x 80mm sound 30 times.

171. Insert a 11.5mm x 120mm sound 10 times.

172. Wear a catheter 7.5mm x 70mm for 3 hours.

173. Masturbate to the point of orgasm and continue all stimulation for 5 minutes after

cumming.

174. Masturbate to the point of orgasm and continue all stimulation until you cum again.

175. For a period of 7 days edge 3 times a day but don't cum. Then on the last day cum 5 times.

176. Give a blowjob to a dildo (size L) for 45 minutes and use cum (real or fake) as lube. Reapply

it every 5 minutes.

177. Deepthroat (23cm/~9inch) a dildo (size XL) 40 times in one sitting. After you're done

deepthroat it another 10 times for 6 seconds each.

178. Use a squirting dildo (size L). Give it blowjob for 15 minutes with at least 30 deepthroats

(19cm/~7.5inch). On your last one, deepthroat it as far as you can and squirt 50ml of fake cum

down your throat.

179. Gag yourself with your fingers 10 times.

180. Make a clothespin zipper that runs from one of your breasts, around your navel and back to

the other breast (20 clothespins minimum). Keep it on and spank your ass until it becomes red

(50 times minimum). Then pull the zipper hard and fast.

181. Attach clothespins to your nipples and insert a buttplug/vibrator/dildo in your ass. Tie

yourself in a hogtie/frog-tie/mummy-tie for 1 hours while blindfolded and gagged.

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182. Go in chat or online and request 10 slave tasks to perform which preferably include

bondage and pain. Spank your ass hard 20 times and your balls/pussy 10 times for every task

you refuse.

183. Wear a different Pantie color for each day of the week…or a different style for each day. For

example, Monday can be pink or thongs and Tuesday can be purple or fullback panties.

184. Dresses up as a Sissy and take lots of photos! Send it to a partner or online friend, they can

use that as “consensual blackmail” in the future.

185. Take a friend to the mall and shop for some sexy panties together.

186. Suck A Big Fat Cock, this is something that every sissy maid should be able to do! Start small

with a small vibrator or dildo before you move up to something bigger. When you are ready,

you can move on to the real thing. But be sure you get lots of practice in before trying it on a

real cock so you will not embarrass youself.

187. Go out to the bar, a dive bar or a gay bar the guys that go to that scene are exactly who you

want to approach. Go there and try to talk to some guys while wearing your sissy outfit. Your

sissy task for the night is to ask at least 3 guys if you can suck their cocks. Ideally, it’ll be

something like in the bathroom or in the parking lot. Make sure to record everything.

188. Dress up in a pretty outfit and go to the local mall. Your task will be to go to the makeup

desk at a big department store and ask for some help or advice on picking out some new

makeup. Pick up a concealer or do your eyelashes or pick out a new lipstick. Wear a vibrating

butt plug and turn it on when you ask for help.

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189. Dress up as a princess – this works best if you are going to some kind of costume party at a

bar or house party. The sissy goal for the night is to make out with someone at the party in

your sissy outfit. And remember: you need a picture or it didn’t happen.

190. Servicing your mistress’s bull is one of the great pleasures of life! After all, you are taking

care of the person giving your Mistress so much pleasure. Learn what he likes and put your

blowjob skills up to the test. After all, you must be a good fluffer for her.

191. A good sissy should take proper care and groom herself. And this means all body hair as

well. So shave/wax those legs, armpits, arms, back, chest, and pubic hair! A favorite is going to

the salon to get a real waxing. Now only is it humiliating, but it will be painful too.

192. Go out to the salon, or to the movies. The catch is you must be wearing a vibrating butt

plug that. Imagine being out in public and having a sissygasm. Then you’d have to hide your

wet spot or else everyone can see.

193. Why does he have holes if they aren’t meant to be used…There’s nothing like bending over

and have her taking your ass. And don’t forget to call her daddy while she pegs you! In fact,

say “thank you, daddy” every time she thrust into your sissy hole. A pegging session is always a

great way to submit.

194. Shrink your “dick”. The best (and most fun) method to accomplish this is with chastity.

Long-term chastity can effectively shrink your manhood. Why? Well, when you go a long time

without an erection, collagen, smooth muscle, elastin, and other erectile tissues will begin to

deteriorate. Over the long run, this can result in a loss of penis length and girth along with

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 weaker erections. All in all, chastity is very effective, painless, and a fun way to shrink your

manhood. With each passing month, your manhood is getting smaller and smaller.

195. Train to be as feminine as possible. Makeup is in the advanced tier because it requires more

work and skill as opposed to putting on a pair of panties/thongs. But that’s no excuse not to

train to get good at putting on makeup. Watch a bunch of makeup tutorials on YouTube

before getting some practice in. After every practice, rate your makeup skills from a scale of 1

to 10. And if you’re not improving, put yourself into chastity for longer to incentivize yourself

to improve your performance.

196. Cum in your chastity cage. It’s kind of like having a ruined orgasm. The cum kind of just

dribbles out like with a creampie pussy. Now, keep in mind, you have to be REALLY horny in

chastity to be able to cum like this.

197. Do a Twitter RT Game. Creating a Twitter re-tweet (RT) game is also a great way to get

exposed. For example, you can do a chastity RT game by posting a photo of dressed as a

chastity sissy all locked. Here would be the terms of the game:

Comments = 3 days in chastity

RTs = 2 days in chastity

Likes = 1 day in chastity

Make the game last 20 minutes and see how many comments, RTs, and likes it can get.

This is kind of like “crowdsourcing” your chastity sissy lockup.

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198. Record a video of sucking a big fat cock. Don’t forget to make the cock owner you’re you

instructions/tips and call naughty things while you’re doing the dirty deed. Watch it on repeat

over and over again. That’s perfect if you want to edge…

199. Go through airport security…with your cage on. Now, for most airports, going through with

a plastic/resin chastity cage *should* be fine…keyword: should.

But you never know if you will set off the detector at airport or if the security guards want to

do some extra screening. However, just the thought and idea of being caught like that should

get your heart racing at 1000 miles an hour. What would you say to the security guards? That

you’re wearing a chastity cage? Would they request a private screening?

Oh…it’s so humiliating just thinking about that conversation haha.

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