pretty-boy: Friday update

from pretty-boy's email to me [pretty-boy has been instructed to refer to herself as "sally" in all FB and email communications]:

Yes mistress i will try to get to the shop at weekend .but wife will be off work so i will see what i can do. I will cum and let it dry on me .

Your,toy,sally
 Mistress i must say that my ball ache now that u let me cum and been locked back up . iv not wash my cock or balls , iv left my dry cum on them.

Your ,toy sally

Mistress i cant seem to get u out of my mind all i can thing of is u giving me order . I wait to hear from all day long . I keep looking at ur blog at what uv said and i get a hard just reading it.
It the same when u message me on here . If i was single i would do anything for u .
Wish i could be take away to be a full time slave for someone to live 24/7 as there slave .
 

Your ,toy sally

 

This is so real for me to be a slave or sissy. i hope u can help me become that slave and get me to meet someone who would have me as there slave .

Your ,toy sally

Tiffany: pretty-boy's weekend assignment

pretty-boy, my sissy slave, was given two instructions for Friday and the weekend. The first was to cum all over herself and leave it there to get dry and crusty, a reminder all day of her obedience. The second - not finished yet - is to go to a women's dress shop this weekend and ask to try on three different dresses.

This is a simple exercise in obedience and humiliation that I hope the Circle will find enjoyable and that pretty-boy will find edifying.

pretty-boy: second day assignment

Good morning mistress.
I did what u told me to do, i cum over myself and eat some .
Iv now put myself back in chastity belt .
I will try to get time tomorrow to go to clothes shop and try on 3 dress as u told me to do .
I wait for more instructions from u .
Your,toy sally 

This is me this morning mistress
Your toy, sally 

Tiffany: pretty-boy (Thursday assignment)

pretty-boy is proving himself to be willing to dress up for me, so I thought I would introduce a little more play for him. I gave him this instruction:

T: tonight, before bed, you will stand with your legs spread and spank your balls with your hand 5 times. then rub until you are hard but do not cum.

A few hours later, he posted:

p-b: Mistress iv spank my balls 5 time it hurt like hell got a hardon just doing that ,my balls r throbing like mad mistress. I tuck my chastity belt of to do it mistress and have put it back on again.

That post was about 5 hours ago, he has no doubt gone to bed by now. He's kind of fun to play with, like a little doll. Here is the assignment I am sending her for tomorrow:

Beginning today, you will refer to yourself as Sally not Simon. Each message you send me in Facebook and each email you send me will be signed: Your Toy, Sally.

You have some shopping to do. First off, you will need a small and a medium sized butt plug.

Second, you will need a body suit to smooth you into an attractive form. These are examples:
http://www.barenecessities.com/flexees-firm-control-easy-up-easy-down-minimizer-bodysuit-2306_product.htm?pf_id=Flexees2306&search=&manual_cm_sp=SlotLocation-_-R7C4-_-Flexees2306

You will obtain one in black and one in tan or flesh color. If your wife already has such things, you may use those. Or you may buy similar bathing suits. They must be tight though. And it is important that they snap open and shut in the crotch.

Third and finally, you are to go shopping at a local clothing store. You are to try on three ladie's dresses, one at a time. 3 trips to the ladie's changing room. Take pictures of yourself in the mirror in the changing room each time and send them to me.

Continue wearing the chastity belt at all times.

If I am pleased with the photographs, you MAY be allowed to cum once this weekend.

XXXX
Tiffany

pretty-boy: Day 2 (Thursday morning)

This is me this morning mistress

This the other pic u wanted from me mistress

pretty-boy: Introduction

Mistress Tiffany told me to make an introduction:

My name is simon , iv want to be a slave for some time now for some 1 .
Iv been crossdressing from a young age about 10 of so .
I would like to serve a mistress or a master .
I want to be change from the person i am now to a totel slave .
I will do anything to please a master or mistress it can be anything .
I had a thought once to become a female doll slave to be used in any that please.
Have cum running out of any of my hole .
Iv never suck a cock but will if a master or mistress made me do it .
I long to be in a chastity belt that will keep me sub .

The longer am in a chastity belt the more sub i become .

I love to see pic of male change into sissy or forced fem 
it is a dream to be a slave 24/7 365 days

This is a pretty picture of me, dressed as you ordered

 

Tiffany: pretty-boy chat and assignments

As I've said earlier, I have taken on not one, but two male submissives. I wanted to give you some information on how things are going with pretty-boy. While I've decided young-bound will be my pain slave, pretty-boy will be my sissy slave. Frankly, his body is in slightly better shape and he seems less able to take pain than y-b. Plus, he seems much more of a fem type. I am more than willing to help him on his journey.

Most of his early messages to me were similar to this one: 

If ur dom would u like to control me ? I dont care what kind of slave i have to be to some1. I dont mind crossdressing or been a sissy slave ,or bondage slave as long a i can serve some1. A master or mistress

Clearly someone who could be fun to play with. I gave him these rules as a start:

1. You will begin tomorrow morning. You will masturbate onto your breakfast (whatever it is, a bowl of cereal, a piece of fruit, a pastry). Take a picture of it and send it to me at ------ Then eat it. When you wake and before you go to work, make a simple post on FB that says "Yes, Mistress"

2. You may use the toilet only two times a day. Upon first rising and between 9 and 9:15 in the evening. If you cannot use it at these times, you will hold it until the next time.

3.  No cumming without permission. You may masturbate any time you wish.

4. When you dress for work, wear ladies underwear. Send me a picture of you in your pretty panties.

He immediately agreed and added a few suggestions of his own:

p-b: I dont have a butt plug but can get 1 , i have a chastity belt if that any us. Can I wear tights as well?




Certainly is an anxious little fellow, isn't he?

XXXX
Tiffany

Welcome pretty-boy and young-bound

As most of you know, It's very unusual for me to take on male submissives. The female body is so much more beautiful and interesting. But two particular fellows on Facebook were persistent and I've agreed to take them both on for a two week trial. They are beginners and very clumsy about it, but seem reasonably bright and willing to be taught.

I've assigned one of them to be a pain slut and one of them to be a cross-dressing denial slut. I named the first one young-bound and the second one pretty-boy.

I have had chat sessions with both of them. I've also assigned them some homework. I will go back and get the chat logs and post them here. 

I hope you find their experiences so far to be as amusing. I am looking forward to the rest of our time together.

XXXX
Tiffany