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2 ? Hurry

Background/update

In my last story, my new subject Muffin and I had our first live session. He is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professes to be most interested in being gradually transformed into a sissy maid and forced to serve in various ways.

When we first started corresponding he did not have a girlfriend, although recently he indicated he has started casually dating a woman named Tammy.

The session I am about to describe comes two sessions after the one in my last story. The intervening session was fairly similar to the first one and included additional obedience drills. I've decided to omit describing them as somewhat repetitive.

By way of closing some open ends, Muffin completed all of the homework assigned at the end of his first session. He arranged a new e-mail address and bought me a nice keychain with Muffin engraved on it.

His journal of times touching his cock seemed a little incomplete and I rebuked him for this. He pledged to do better before the session I will shortly describe.

His gift to his girlfriend Tammy was a pair of back-seamed stay-up stockings. He asked her to go out for dinner and dancing and encouraged her to wear the stockings telling her he thought she'd look great in them. She apparently gave Muffin a hard time about his motives suggesting he thought she was easy.

She did wear them however and they had a nice time. Muffin reported that they "kissed a little" at the end of the date, but she broke it off before things went any farther.

One of his homework items for the session described below was to ask his girlfriend's permission to make a further move with her during a following date.

Session plan

I have obtained a room at a designated hotel. Muffin is to arrive promptly at 5pm. I am wearing a tight, red knit, above the knee, cowl neck sweater dress, black leggings and shiny black stiletto knee boots. It is a very form fitting and sexy outfit. We will review prior assignments and will play a game to test self control.

* * * * *Session transcript * * * * *

Knock, knock

"Greetings Muffin. Come in, strip, and stick your wallet, keys, personal items and shoes in the safe in the closet next to you. Fold the rest of your clothes neatly, then crawl to kneel before me with your journal."

I seat myself on the corner of the bed. Muffin crawls naked to a spot two feet in front of me. After about two minutes, without a word, I slide my left foot forward.

(Subject kisses the toe of the left boot I have extended) "Thank you mistress for allowing me to serve you.' (Subject kisses the toe of the right boot) 'It is my honor to serve you and all women.'

"Very good Muffin, it appears you are trainable after all. Please stand."

Muffin stands, in place, head down.

I slip a blindfold over his head and adjust it.

"Can you see anything?"

"No Ma'am."

"Good, hands above your head, close together."

I stand and fasten him into padded leather hand-cuffs with limited play between the cuffs.

"Very nice Muffin, you may lower your hands. I see you have a hard little dickie for me. You must like being restrained in addition to all of your other weaknesses. The only good thing about this is it will be easier to lock this cock and ball ring on you."

Mistress clicks a ring in place at the base of the subject's cock and fastens it closed with a small padlock. A short length of leather with a small bell on the end of it has been knotted onto the ring and dangles between the subject's legs. The bell gently tinkles when the subject moves.

"Kneel before me while I tell you a bit about our plans for today. I hope you got a good look at me in my very sexy outfit because it might be the last you see of me today depending on how you do. A friend will be meeting me here at 7pm and you have some tasks you need to perform before then.

As you may have figured out, in order to leave this room in any type of presentable manner, you'll need to earn the key to the lock on your cuffs and the lock on your balls. You'll also probably want the combination to the safe to get your belongings.

I'm sure my friend will be quite prompt and will probably get a good laugh at seeing you in whatever state you might be in, unless of course you earn your way out first. I've set the alarm clock for 7 pm so you'll know when your time is up.

Lets start by reviewing your little penis journal shall we? I had some questions about the accuracy of it last time, so perhaps before I look you can tell me how you did. Can you tell me how many times you jacked off since our last session....hmmmm must have been just less than two weeks ago."

"I have only jacked off twice Ma'am."

"Twice? Really, in two weeks? A sissy like you I would have expected a number more like 20 times or maybe more. Why only twice? Were you sick? In a coma? Why?"

"Last session you Şenlik Escort seemed to be angry at my lack of control. You said I came too quickly, so I practiced controlling my orgasms Ma'am."

"Admirable, but I'm still not sure I understand."

"I edged myself a number of times, but I only actually came twice. Once last Saturday after my date and then once yesterday, so I would be able to last for you today, Ma'am."

(Opening journal) "Hmmmm. I see what you've done. This isn't really what I had in mind. You seemed to have created a bit of a loop hole between edging and actually working yourself off to completion.....let's see here, how many edges did you record....I count thirty one times does that seem right?"

"I guess so Ma'am. I'm sure you're right."

"Hmmm this really won't do at all. If more control is what you want, more control is what you'll get. You have brought this on yourself. Not cheating really, but I think a breach of my intent.

I think its time for a new rule related to your journal and handling of that tiny little cock of yours. Starting now you will only be allowed to jack yourself off three times in a week and no more than five times in two weeks. Never two days in a row either. Starting now there is no distinction between edging or cumming. If you touch it to make it hard, it goes in the journal and is subject to these limits. Clear?"

"Yes Ma'am, sorry Ma'am. I wasn't trying to cheat. I thought I was doing something good, limiting myself and all."

"Well there's the mistake isn't it. Thinking. Thinking with your little head too, no doubt. Let's also change this journal. You don't need to record anything other than your little wank sessions. It will be a jack-off journal I suppose.

When you record it I want lots of details? how you did it, what made you want to do it, what you thought about when doing it, how long it took, how you cleaned up, every detail of your little session. It will no longer be a private pleasure, you will share every bit of it with me.

Don't even think of cheating, I will know if you don't record every session and every detail. I can crack a sissy like you in a second. Your face and the lie detector between your legs would give you away. You've failed with this journal twice already. There won't be a third time."

"Yes Ma'am. I understand."

"Well my plan was for you to worship my boots for one minute per orgasm, but clearly that won't do. I'm not sure how to judge thirty-one edges if those should count more or less. I'm going to say you have seventeen minutes of boot worship, fifteen minutes for the edges and two for the actual times you came. You may start now, I'm sitting right in front of you. You may kiss and lick my boots, but do not slobber. Begin."

Muffin begins actively kissing the toe, top and sides of mistress' boot. His bell tinkles occasionally as he adjusts position. I flip though the journal for a minute or two then hike up my dress and begin gently rubbing myself through my panties and leggings ? his mistake has given me a delightful idea, which I am sure will prove quite entertaining and I am aroused thinking about how he will respond.

After the allotted 17 minutes:

"That will be quite enough, you may stop. It's time for you to answer a few questions. I've been looking at your journal and I think you need to provide me a little more detail about your two actual jack-off session. Maybe you can begin with the one last night where it says you were thinking about me. Why don't you describe your fantasy in detail hmmmmm?"

(Blushing beneath the blindfold) "Yes Ma'am. I was just thinking of you and our last session. How pretty you looked at our last session, your sexy black stockings and the heels and I imagined that you had forced me to be your maid and to serve you and I kept thinking of what that would be like and eventually I couldn't control myself and just came in my hand."

"Do you think I like the fact you masturbated while thinking about me? Do you think that pleases me Muffin?"

"I'm, I don't, I mean, I guess I'm sorry Ma'am."

"You're not sorry Muffin, don't lie to me. I know pretty sissies like you get little submissive thoughts in your head and can't control themselves. I know that. That's why you're all hard right now aren't you. You're hard from kissing my boot and hard because I'm making you kneel before me. I'm sure if I ordered you to cum on my boot you would beg for the chance to do it and then beg me to lick it up afterward. I know you are weak and have no control.

Maybe you should tell me about this little session after your date. With Tammy I suppose. Tammy "the four", with the cute butt. Tell me about that session."

"Um, well, yes Mistress, of course Ma'am. It was Tammy. We had gone out and it was nice and we went back to her place"

"You whacked off at her place? Really?"

"No its, well, Ma'am you....my homework was....you know, to ask for permission. So after the date we went to her place and Şenlik Escort Bayan we were kissing and I asked her if it would be ok if I rubbed her breasts and well, she didn't want to at first but then she said O.K. So I did and....."

"What about her, did she take care of you? Did she give you a few strokes on the old sissy stick."

(Red faced) "She did, she rubbed me there a little, but then just when it seemed like things might go a little farther she broke off and said that was enough. She said it was her period."

"Hmmm. The old "on my period" excuse. I'll bet. More likely she got a feel of your little thing and decided it wasn't worth it. Could that be it?"

"I don't know Ma'am. I hope not. Anyway she had me worked up, so I went home and rubbed one out."

"Rubbed one out thinking about pretty Tammy. Tammy the four. I'm sure she'd have been very proud of that. She probably doesn't get guys rubbing one out thinking about her very often. Maybe you should tell her? Tell her how hot she made you. I'm sure she'd help you out next time. What do you think?"

"I doubt it Ma'am. Tammy's not like that too much."

"She seems like she'd be a good tease and denial mistress for you. Would you like that Muffin? Would you like Tammy to control your orgasms? Make you beg for them?"

"I don't think so Ma'am....she....I don't think."

"Do you know her phone number Muffin? Have you learned it?"

"Umm yes, yes Ma'am."

"Good. Maybe I should give her a call and tell her what kind of boy you are. Tell her how much you like to serve women? How you whack off thinking about her. How about that..."

(Very nervous) "No, no please. Please don't Ma'am."

"I think maybe you should trade one of your locks for her phone number. What do you think of that?"

"Please Ma'am. Don't do that."

"Yes, I think that's quite a fair trade. You give me the number and I'll release your cuffs. That's the deal. Stay in the cuffs or give me the number. You have a lot to do still and the clock is ticking. The number for a lock or you can decline and see what other opportunities present themselves. Which is it?"

(Head bowed submissively) "I'm sure I shouldn't but her number is 555-1234, Ma'am. Please go easy on me, please."

Bending down I unlock the hand cuffs.

"You need to trust me Muffie. I've always been fair and discrete. I might not even call her right away. I might save it for when you displease me and I'm sure you will sometime.

I bet she would like to know how you've been training to be a sissy maid though. As a budding T