The following posts are tagged with sissy assignments.


Sissies, Strike a Pose!

I read recently that the new fall look contains the one shoulder treatment! Many dresses and blouses have one shoulder bare, while the other is gathered into a pretty little strap. For those of you cross dressers who like to wear the latest trends, this may present a bit of a challenge. Many of you […]

Sissy Assignments

Buy yourself some nice pink panties… You’re gonna be wearin’ them all week and washing them with you tongue every night!If you want to discuss any of your sissy assignments in a feminization phone sex call, just clicky clicky on the button below:

Sissy Assignment

Get a bikini wax. After all, swimsuit season is almost upon us. *wink*If you want to discuss any of your sissy assignments in a feminization phone sex call, just clicky clicky on the button below:

Sissy Assignment

Purchase a toe ring. Wear it under your regular shoes. It will be a daily reminder of how humiliating it was to go into a store and buy a toe ring.If you want to discuss any of your sissy assignments in a feminization phone sex call, just clicky clicky on the button below:

Sissy Assignment

Pluck your eyebrows! Get rid of those manly straggly hairs. Then ask some of your closest friends if they noticed that you plucked your eyebrows.If you want to discuss any of your sissy assignments in a feminization phone sex call, just clicky clicky on the button below:

Sissy Assignment

Use a pink, flowered, or otherwise feminine looking coin purse for the spare change you usually carry in your pocket.If you want to discuss any of your sissy assignments in a feminization phone sex call, just clicky clicky on the button below:

Sissy Assignment

Go to a cosmetics counter and ask which shade of lipstick will go best with your coloring. Then buy that shade.Happily giggle and twirl your purchase bag as you leave the makeup counter.
If you want to discuss any of your sissy assignments in a feminization phone sex call, just clicky clicky on the button below:

Sissy Assignment

Cum onto your hand and lick your vile filth into your mouth. Do NOT swallow. Hold it into your mouth for five minutes. Swish and swirl it around your mouth. At the end of the five minutes, gargle with your cum, and then swallow it.Do not put anything else into your mouth for at least […]

Sissy Assignment

Wear pink socks cuz you’re tickled pink, all the way down to your twinkle toes!
If you want to discuss any of your sissy assignments in a feminization phone sex call, just clicky clicky on the button below:

Sissy Assignment

Cum on your face today.  If you aren’t limber enough to shoot your load in your face, then catch it in your hands and smear it on your face.  Wear it for at least 15 minutes.  If you have more privacy time, then wear it longer.
Now you’ll know what it feels like at a circle […]

Sissy Assignment

Paint nail polish on you fingernails and leave it on for at least 48 hours.
If you want to discuss any of your sissy assignments in a feminization phone sex call, just clicky clicky on the button below:

Sissy Assignment

Paint nail polish on you fingernails and leave it on for at least 48 hours.

Sissy Assignment

Complete an errand, such as shopping, with a lubed butt plug up your ass.

Sissy Assignment

Go to the lingerie store buy some sexy panties or thongs, in pink.  Tell the clerk, as you purchase them, that wearing panties makes your nipples all tingly.
If she has questions, by all means answer them.

Sissy Assignment

Shaving day.  Trim or shave your pubic hair today.
Then shave your underarms and legs.  

Sissy Assignment

Cum in your hand at work today.  Then put some of that slimey splooge on your upper lip and in some of your nose.  Walk back to your work station and leave it there until someone says something about it.  I’m sure they’ll just think you have a runny, snotty nose and tell you to […]

Sissy Assignment

Tie a very pretty bow around the base of your cock.  Wear it all day.  When using the restroom at work, use the urinal. 
Don’t try to hide it.  I wonder if anyone will  notice how you prettied up your cock!

Sissy Assignment

Wear pantyhose or nylon knee highs to work today.  If you don’t have those, then wear some pretty pink socks - lol!
I wonder if anyone will see your nylons under your pants.  Better sit down very carefully - lololol!

Sissy Assignment

Shave your forearms today. 
I wonder if anyone will notice.  Do people even notice you?

Sissy Assignment

I want you to put two slightly melted ice cubes up your ass.  Now put a dildo in your butt (or a wooden spoon) and fuck yourself. 
Quit crying.  Your mascara will run, sissy!

Sissy Assignment

For all correspondence at work, from now on use a glittery pink pen!

Sissy Assignment

Cum in your hand, then rub your cum all over a dildo.  If you don’t have a dildo, then why don’t you!?!  At any rate, use a substitute for a dildo, be it a cucumber  or whatever.  (Geez, you really SHOULD have a dildo!)
Then suck that cum covered stand-in cock til it’s all clean.  Doesn’t […]

Sissy Assignment

Take a container yogurt to work some time this week for a snack or lunch.  Before you eat it, go into the restroom with it.  Go into a stall and stick your dick in it and cum. 
Then clean up and take it into your break room and eat that extra creamy yogurt.  Gotta get used […]

Sissy Assignment

Fuck yourself in the ass 3 different times today.

Sissy Assignment

Dress up your penis today.  Use a waterproof marker and make a little smilie face.  Or, if you have a small wee wee, make it a sad face or a mad face.   You know it would be alternatingly sad and mad at  being so small!
Improvise and put some material on your  lil buddy and make […]

Sissy Assignment

Go to a nail salon and get a manicure.  Yes, even men get them.  Ask for a very shiny clear nail polish, with a hint of pink to be put on after your manicure. 

Sissy Assignment

Here’s another sissy assignment:  Buy a hand lotion with a feminine scent.  Use it daily especially before meetings when you will have to shake hands with people.

Sissy Assignment

Hi, sissies!  Here’s another sissy assignment:
Cum in a condom.  Then carefully suck out the contents.  Swish it around in your mouth and hold it for one minute.  You need to get used to this man slime taste, and lots of it!
Bon Appetit!

Sissy Assignment

This is a sissy humiliation assignment:  Carry around something like a banana.  I want you to put it on your desk at work, or in your locker.  Then when it’s break time, I want you to look lovingly at it, no matter who is around.
Sniff it, smell it, kiss it.  Say:  “I love my banana.”  […]

Sissy assignment

Hi, sissies!  I hope you all had a fab New Year’s!  I also hope you’ve made your sissy resolutions!!  If any of you want to share them, please do so.  You can put them in the comment section on this particular blog entry.  This sissy blog is set up for me to approve the comment […]

Sissy Assignment

The next time you go to work, you will wear a pair of control-top pantyhose under your guy clothes.  No excuses! 
If you don’t have pantyhose, uh…why?  You’re a sissy!  You should have a nice pair of control top pantyhose!  Don’t just sit there, go buy some now!

Sissy assignment

Hi, girlies!  Here’s another sissy assignment:
Wear a lubed butt plug up your arse at work today for at least 2-3 hours.  Do you wonder if you walk funny?  Do you wonder if people will notice something is different about you?  They probably do!

Thursday’s sissy assignment

Here’s anonther sissy assignment:
Go to a female dominated work place - like the restaurant Hooters, or a lingerie shop. Ask someone who works there for an application for  employment.  If  you’re too chicken, say it’s for your wife/girlfriend.  If you’re really wanting to be humiliated,  say you’ve always dreamed of working in a place like that.  […]

Thursday’s sissy assignment

Here’s anonther sissy assignment:
Go to a female dominated work place - like the restaurant Hooters, or a lingerie shop. Ask someone who works there for an application for  employment.  If  you’re too chicken, say it’s for your wife/girlfriend.  If you’re really wanting to be humiliated,  say you’ve always dreamed of working in a place like that.  […]

Wednesday’s sissy assignment

Hi, bi-curious sissies.  Here’s another daily sissy assignment:
Put a dildo in the freezer for a half hour to an hour.  I don’t want it frozen, but I want it cold!  You have to get used to being butt fucked by even the most distasteful of cocks.  Hahahahaha!
Use a condom; you don’t want frost bite.

Sissy assignments

Here’s a sissy assignment for you:
Shave your public hair into the shape of a little heart.
Have fun!  Maybe it’ll make your little sissy clitty appear bigger.  LOL!