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Lipstick and Stockings – Feminization Assignment

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Feminize Those Lips!

Feminize Those Lips!

A little bejeweled birdie has come to me with a woeful tale. According to said birdie, she’s been feeling all left out as she doesn’t care for masturbation games, and is longing for something that will help her get in touch with her feminine side.

I’m just the kind of person to make that happen.  And because I happen to be in a mellow mood today, I’ve decided to give her…and all other feminization fans, something to do over the weekend.

Things You’ll Need

In order to experience this assignment as intended, you’ll need:

a)  A pair of stockings or pantyhose.  I’ll let you decide what your preference is.

b)  A shade of lipstick that compliments your skin tone.  If in doubt, you need to call in for a beginner’s makeup consultation.

c)  A glass glass, preferably a wine glass.

Enjoy the Preparations

The first thing that you are going to do is to put on your stockings or pantyhose.  I want you to really pay attention to the sensations as you pull them up over your legs, and smooth them out.  If you are using seamed ones, that is a bonus, and you’ll need to look in the mirror to make sure that you have your seams straight.

If you have any high heeled shoes, now is a perfect time to put them on.  But if you don’t, there is no need to fret.  You can still do this assignment, and who knows….you may get a shopping assignment in the future.

Now it’s time for the lipstick.  If you need help with this, go to youtube and watch one of the zillions of tutorials by the makeup gurus on how to apply lipstick.  If you have any lip liner, use it.  I personally use and recommend clear liner, as I never have to worry about the color of it clashing with my lip color, and it helps keep things well defined.

Finally, pour a beverage of your choice into your glass.  For optimum effect, the girlier the drink, the better.  But whatever you choose, do not fill your glass all the way up.  We want to leave a space of about an inch or so.

You are to enjoy these preparations, and not rush through them.  After all, the journey is as much, if not more fun, than the destination.

Practice Being a Lady

Now that you are all prepared, you are to sit down, and cross your legs at the ankle, then draw them back under your chair, just like a proper lady.  You’ll want to keep your spine nice and straight for that.  I want you to focus on the way that it pushes your legs together, and how they feel.

Then you are to plant your left foot on the floor in front of the chair, and cross your right leg over your left at the knee.  Pay particular attention to the way that one stockinged leg feels as it rests against the other.  Lightly swing your right foot back and forth.

Pick up your glass, purse your lips over the rim, and take a small sip.  See the pretty, feminine lipstick prints that you leave behind?  In an unhurried manner, continue that around the rim of the glass. We want a thick, prominent impression, so repeated applications of lipstick are probably in order.

Pay Attention!

Live fully in this assignment.  By that, I mean be very present, and aware of what is going on in that exact moment.  Don’t get all jazzed up about how your sissy stick might want to explode all over the place.  That is nothing new.  Keep your focus on where it should be…exuding an aura of feminine grace and beauty.

Filed Under: Assignments, Feminization, Sissy Tagged With: , , ,

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Calling All Cock Suckers! Sign Up for Glory Hole Duty!

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Go on. Suck it. You know you want to!

Go on. Suck it. You know you want to!

I know you are out there. You may lick your lips in anticipation, or you may need me to grab you by the scruff of your neck and force you. But  you, pet, are a glory hole cock sucker, and you need to have anonymous tube steak stuffed down your throat.

Either way, I like it, and I like it even more when I can be on the phone with you, and listen to the sounds as you slurp happily away at your local bathhouse or adult bookstore, knowing that you are pleasing me.

Alas, For Some of You, That is Only a Dream

Some of you absolutely love the idea of being a glory hole bitch for me, but your reality keeps you from doing it.  If that describes you, fear not.  There are still things that you can do to honor me and show your willingness to do exactly what I want.  One of those things will be your assignment for today.  That’s right, you are going to simulate a glory hole.  Just because you can’t have the authentic experience does not mean that I am going to let you off  scott-free.  That wouldn’t be sporting, and I do so love a level playing field.  Except for the part that I am standing on, of course.

Can We Build It?  Yes We Can!

Since your life circumstances dictate that you cannot serve me by seeking out an actual glory hole, you are to construct one.  Points will be given for creativity, but a cardboard box will suffice if that is the best you can do.  What is important is that you have a phallic-like object sticking through the hole, and that you open up like a trooper to take as much of it as you can in your mouth.

I love pictures, so more points will be awarded if you send photographic evidence of your devotion to carrying out tasks.  It is permissible to just show from your nose down in the images.  That will be enough to illustrate that you are carrying out your assignment, and pleasing me.

That is the thing that truly matters, puppets.

 

 

Filed Under: Assignments, Cock Sucking, Feminization Tagged With: , ,

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Spring Cleaning – Sissy Assignment

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Take Ms Suffer's White Panty Test

Take Ms Suffer’s White Panty Test

Alright all you sissies.  It’s time to get to work!  It’s clear that if I don’t crack the whip that you’ll do nothing but laze about every day, browsing through Victoria’s Secret catalogs, and rubbing your clitty through your panties.

The burden of that is rather on my shoulders, I suppose.  I’ve been busy and derelict in my duties.  And Lord knows I can’t depend on you to see to it yourself.  You’d rather spend your time oooing and ahhing over the latest issue of Cosmo. But all that is about to change.  You will get off your chaise lounges, and swish your asses into gear.  Starting now.

Your Assignment – Spring Cleaning

That’s right, I said cleaning.  Get too mouthy about it, and you’ll be licking the toilet bowl clean.  Any more distention?  I didn’t think so.  So let’s get started!

If you are a sissy who actually has a French maid outfit, then by all means, put it on!  If you do not have one, then wear something black and white.  If you don’t have something black and white, then find an image on the Internet and print it out for your motivation.  Then visualize yourself in it, serving me.  That should help get you in the proper frame of mind.

First Job – Tackling the Refrigerator

Open the door.  Do you see a bunch of calorie-laden junk food?  If so, toss it.  No self respecting sissy is going to be eating that garbage.  You need to get that waist whittled down to be more visually appealing to me and whoever I decide to have you service.  If you need assistance in that area, you can sign up for my Whipping You Into Shape Program.

Next Up – Straighten Your Sissy Things

Your “sissy things” are going to vary for each of you, and since I’m not there to see what needs done, you will need to take the initiative and do it yourself.  Report what you did in the comments.

For some of you, this will mean going through your makeup, getting rid of what doesn’t work…no dear, you do *not* look good in lime green eyeshadow…sorting through the old, etc.  If you don’t have a train case, get creative.  Use a cardboard box, and let your sissy energy flow, decorating it with feminine images and colors.  If you do this option, take a picture of your creation and send it to me!  I’d love to see it.

For others, this will mean judiciously sorting through lingerie and stockings.  Have a bra with a busted strap?  Mend it!  Are your stockings filled with runs?  Keep them in the cleaning bin to use to shine my boots, and note on your shopping list that you need to buy new ones.  Are your panties all in a jumbled mess?  Fold and organize them, either by color, by style, or by fabric.  I personally like the by color option.

For the grosser sissies out there, this may mean actually cleaning your toys.  You don’t even want me to start on how disgusting it is that you’ve not cleaned your dildos since last year.  Or maybe you do, but now is not the time.  Just get busy!

Finally, Break Out the Feather Duster

Some of you sissy whores have been waiting with baited breath for this one.  You’ve been hoping that I’ll tell you to stick the feather duster up your ass and use it to dust with.

If you want to, I won’t deny you.  Though I won’t insist either, as it’s really not as much fun for me to hear about as it is for me to watch you do it on cam.

You can either do it sissy style, with feather duster protruding, or normally, but I want every speck of dust gone.  Don’t forget about any cobwebs that have formed over the winter.

When you are done, it’s time for the test.  Instead of a white glove test, we are going to do a Miss S White Panty Test.  Take a pair of white panties…a CLEAN pair, for any panty sniffers that are reading…and put your fingers inside the crotch.  Use it to glide over a few surfaces that you dusted.  Do you see any traces of dust?  If you answered no, good girl!  You can go to the reward below.  If the answer is yes, dust the entire house again, and you are not allowed the reward.

All Work and No Play Make You a Dull Sissy

Now then, if you are one of the industrious ones who takes direction well, and did as she was told, you may now reap the rewards of your hard work.  Look around.  Isn’t that nice?  Not only did you improve your environment, but you pleased me, which should be reward enough for you.

But because I am feeling generous today, I’m going to allow you an additional reward.  You get to lie back on your fresh sheets….I know that you changed them without being told…and you are going to let your mind have the fantasy that gets your sissy stick so hard that it seems as if it will explode.

Then you will let it explode, focusing on me the entire time.

After your breathing and heart rate have returned to normal, you can leave a nice, detailed comment, sharing with me what your fantasy was about.

 

Filed Under: Feminization, Sissy Tagged With: , , ,

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My Sissy Goes on an Adventure – Her First Public Outing

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For starters, I’ll say that in my mind, the term “sissy” when applied to this caller, really doesn’t fit.  I define the terms this way:

Sissy = Obvious guy in over-the-top, frilly clothing, making no attempts at passing

Feminized = May still obviously be a guy, but the intent is being passable, and becoming as much like a woman as they can

Your mileage may very; those are simply my definitions.  However, since the caller in question uses the term sissy to refer to herself, that is what I’ll use as well.

At any rate, my sissy was going on a business trip, and wanted me to plan some adventures for her.  She and I have a pretty in-depth caller/Mistress relationship, so it was fun to plan her itinerary.

Miss Thing, who we’ll call Sissy X, had never been out in public before.  Also, even though I had sent her scores of you tube makeup guru videos, she was still in need of some hands-on makeup application training.  So I decided that we’d combine a trip to the mall with a trip to MAC.  (For those of you who aren’t following along, I’m speaking of this MAC, not this MAC)

I called ahead, and found out that this particular MAC was one that had private, one-on-one lessons with makeup artists who had been pre-qualified to do them.  The artist would do half of Sissy X’s face, then Sissy X would have to do the other half.   I thought that sounded like a great way to out herself a little, as well as a chance to get some expert application advice.  So she was instructed to call in and book the appointment.

Sissy X is a true slut, I know that the whore in her had visions of twitching her ass down the middle of the mall, in a micro mini, fishnets, and platform shoes.  I dissuaded her from that notion by letting her know that our fantasies don’t always play out in reality, and that a first time outing in a mall setting was probably best suited to something casual that would allow for ease in changing rooms and allow her to blend into her surroundings.  We ended up going with some nicely-cut khaki slacks, a pretty print blouse that buttoned up the front, and heels that did not scream “stripper”.

But before Sissy X got to the mall, she made a scheduled stop to pick up some titties.  I had hoped that she could get some beautiful forms, but the store that I was sending her to had those by custom order only. Since I was feeling impatient, and as this was a rare opportunity for her to get away, we ended up going with bra inserts.  Never one to go small when she can go big, Sissy X ended up getting 42D tits.  She picked up a new wig while she was there also.

So not only did she have a pretty new blouse to go to the mall in, she had new boobies to fill it out.  Her first stop was MAC, and the makeup artist did a phenomenal job.  Sissy sent me pics after, and if I didn’t know it was her, I would have not realized it without really looking hard.  She also got quite the haul, picking up about $500 in product while she was there.

Then it was off to the races at Victoria’s Secret.  It was loud in there, and I had trouble hearing lots of what was said.  But I did have the fun of hearing her tell the sales girl that she was shopping for herself, and asking about what size she needed.

Sissy X had business to attend to, but managed to squeeze in a trip to Fredrick’s of Hollywood to pick up a corset and some assorted other goodies.  I was on the phone with her at the time, and it pleased me that the sales people all seemed to take her in stride.

Her last night on travel, we had a session where I watched her on cam.  She showed me all her pretty things as we talked, and then I let her take her clitty out of it’s chastity cage.  She had not been allowed free play or orgasm for 7 weeks, so I decided it was time to celebrate by letting her release.  And what a release it was!  Sissy X embraces my philosophy that a good girl does not leave a mess, and she eagerly cleaned up every drop.

I let her have freedom to play with it that night, then told her she needed to pack her clit away when she packed her bags for the return trip home.  It was a great adventure, and I’m sure not the last that we’ll have.

Filed Under: Chastity, Cum Eating, Feminization Tagged With: , , , ,

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