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

young-bound: Report

Hello, I did it. When we went to bed, I started sex with my wife. I kissed her all over and get her naked. After kissing her whole body, I reached her pussy. I licked it softly and harder and it took not long, until she came. I was dressed all the time, so she could not touch my dick. She was not happy about, but i told her, that it is her day today. I also didn't jerk of myself, because i didn't know how to explain.

I hope, I did it well!?

- K

Tiffany: young-bound chat

These are some highlights of my chats with young-bound. They date back to late February, before I decided to take him on. 

young-bound writes: Hi, would you like to add me? Would really be happy about it. I also would like to meet you on Skype, if you want. I would do what you want me to. Thank you. K

I  expressed some minor interest, to which young-bound responded: I am just a beginner, so you need to teach me everything. Is this a problem? I would like to do videochat with you and you force me to do the things, anythings that you want to see from me!? K

I asked him some simple questions and he gave immediate replies:

T: Tell me what kinds of equipment you have available for CBT.

y-b:  I could take my wifes dildo, clothes-pegs, maybe you have any other ideas?

T: Send me 3 photos of yourself. (He did send but I am not releasing those to the public.)

T: When was the last time you masturbated? What was your fantasy or whose orders were you following?

y-b: The last time i masturbated was on Wednesday. I was thinking of a friend, that came into our sleeping room. She get naked, put one hand over my mouth and the other hand was searching my dick. As she found it, I tried to take her hand, but i couldn't, because i was tied. Slowly she brought me over the edge.

At this point, I did not contact him for two weeks as I was not very interested in taking on a male submissive. At some point in late March, a friend online told me some things she was doing with her male sub and I became curious. 

I re-initiated contact with K

y-b: I'm fine. Nice to hear from you, how are you?

It turned out he was at work. I decided this would be a golden opportunity to test his commitment. I asked him for some details about his office and co-workers, then began playing with him.

T: I came across your emails and noticed you were online. If you are a very good boy, I might pay you some attention. Are you near the start or the end of your shift?

y-b: Just started.

T: Do you know what it means if I tell you to "flick" your finger against the desk? or "thump"?

y-b:  I think i know it. Why?

T: You do not ask questions. I ask questions. Understood?

y-b: Yes, sorry.

T: very good. now, let's make certain you know what it means. Thump the desk.

y-b: It hurts.

T: Yes it does. Do it again.

y-b: Done. Hurts really more.

T: Now get up and walk to the men's room. Bring your mobile.

y-b: I'm there

I had him go into a stall and close the door.  I told him to "stand facing the door, feet where they would be if you were shitting. drop your pants." When he was naked from the waist down, I had him flick his left ball. I asked him how much it hurt on a 1-to-10 scale. He told me "5".  I had him do it again until he felt it was "7". He obeyed.

Once I felt he had a good idea of the pain he was going to endure, I told him to squat a little, then open his mouth round, like he was waiting for a cock. He did it. He send me a pic from his phone. He looked so absurd standing like that, vulnerable and exposed. I was satisfied with his willingness to obey orders. 

Now, I had to test his willingness to hurt himself on command. I instructed him to flick his ball sack 5 times on each side. In just a few minutes, he typed:

y-b: Done, but I'm getting too loud.

T: the flicking? or the moaning?

y-b: The moaning

He passed that test too. I asked him if he was aroused. He reported his cock was stiff and he was in pain, holding himself up by leaning against the side of the stall. I teased him, asked him if  he'd like me to suck his cock, make the pain go away, distract him. He said yes and begged to be allowed to jerk off. I let him rub his cock exactly 5 times, then stop. I made him flick the head 5 times.  He was crying by the time he finished.

y-b begged several more times to be allowed to jerk off. I told him no. But I gave him an option. He was to go home after work and lick his wife's pussy until she came. Her could jerk off as long as his tongue was better her legs. But that was all.

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