Mistress Chronicles Ch. 02

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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 antalya 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 we were kissing serik escort 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&D mistress she might like to know that. Maybe she’d like a little advice from me about how to control you, too. We could meet for lunch sometime….that would be a nice girls lunch. Me and Tammy the four talking about training our Muffin.

Look at you. Its making you drip isn’t it? The idea of your girlfriend and mistress ganging up on you? Dominated by two women.”

“Please, Ma’am. Please. It’s….I’m sorry.”

“Ohhh lookie at all that pre cum. You are so into this….”

(More emphatically) “Please, Ma’am, I’m begging. She wouldn’t. She’s…”

“Shhhh, shhhh, there, there muffie. I’m not interested in calling her right now. But it’s nice to know how much that worries you. It’s hard to believe but Tammy is another one of your weak spots. I’m going to need to think of another homework assignment involving her.

My goodness, look at the time. We still have a lot to do this session. Today I have a little game you need to play. Are you ready? Are you ready for a game?”

“Yes. I’m ready. Thank you Ma’am, about Tammy.”

“I wouldn’t thank me yet Muffin. I’ve made no decisions on that and I will call her when I please. Please pick a number between one and ten.”

“I’ll pick five Ma’am.”

“Good. So this is how this game is going to work. We’re going to get you dressed up in your sissy maid clothes and we’re going to practice some control with a little edging. It’s interesting that you had been practicing already isn’t it?

So you picked five, so that will be five times you will need to edge. After each edge, I’ll let you beg me for a piece of pretty sissy maid clothing. Here’s the thing though. Your total time edging must total 20 minutes over the five edges. Each minute you are short of that total you will need to spend five minutes standing in the corner like a bad sissy. Understand?”

“Yes Ma’am. Ok, begin when I say go. I want to see nice firm strokes. Say ‘edge’ when you are close, but don’t stop until I say stop. Go.”

Subject begins firmly stroking his shaft up and down as ordered. The little bell between his legs beats out an embarrassing steady jingling, tinkling noise as he does so.

“Edge”

“Ok Stop. Not bad, that was four minutes and twenty-five seconds. You have a choice now. You can take a two minute break and then beg me for a pair of frilly ankle sox or you can start begging now, and then rest until five minutes are up. In any case, you will begin side escort your edge again in five minutes. Your choice?”

“I’ll rest first, Ma’am”

“Fine. Lean forward keep your nose pressed to the toe of my boot. I’ll let you know when the begging should begin.”

Two minutes pass in that position. I rub myself again at the sight of my naked submissive with his nose pressed into my boot. There was something very arousing about hearing the bell tinkle as he masturbated himself. I hadn’t thought how delightfully humiliating that would be for him. I love the sexual power I am developing, it’s very fulfilling. I can feel my juices start to flow.

“Beg me”

For a minute or so he begs along these lines. “Please mistress, please may I have a pretty frilly pair of sissy sox? I want them so much Ma’am. Please may I have them, Please?”

Mistress takes the frilly sox from a bag beside her and dangles them up to his lips, just brushing them. “Kiss them, thank me, and put them on. Then back to resting position with your nose on my toe until I say begin again.”

Kissing the sock as he takes it from my hand. “Thank you Ma’am. Thank you for the pretty ankle sox.”

Muffin commences putting them on, which is difficult with the blindfold still on and then resumes position as ordered.

“Begin your edge again.”

Subject sits up and begins firmly stroking his shaft up and down as ordered. Again the bell tinkles steadily in response to his submission. “Edge”

“OK. That was four minutes. You are up to eight minutes and twenty five seconds. Rest.”

Subject resumes resting position. I stick my hand down into my panties and begin fingering myself in my now very moist slot. I continued for almost three minutes. Towards the end I’m sure subject could hear a few moist squishy sounds as I pulled my fingers in and out of my very wet hole.

“Begin begging for earrings now.”

“Please mistress, may I have a pretty pair of earrings. It’s important for this sissy maid to look nice and I would really like to wear a pair of pretty earrings. It would make my face look very girly and soft. Please.”

“Enough. Sit up so I can clip them on you and then resume your resting position for about one minute.”

Earrings are clipped on, subject resumes his position. I roll down the top of my leggings a bit to improve my access. The faint scent of my arousal begins to float in the air.

“Begin”

Subject begins firmly stroking his shaft up and down as ordered. The sound of the bell is incredibly arousing to me as a symbol of his submission. I rub myself steadily and it feels amazing.

“Edge”

“Mmmm not so good that time. You’re getting behind. That’s only three minutes and 15 seconds, so you have eleven minutes and forty seconds with two more to go. You’ll need to average almost five minutes each to avoid the corner. Rest now. Try not to notice what I’m doing up here. Your submission is very arousing. I love a little sissy maid on her knees before me.”

I resume fingering myself making no effort to hide the pleasure I feel or be discrete. I moan several times and the squelching sound of my fingers is very obvious. As subject sits back up I can see that his hard on didn’t go down much at all.

“You may beg me for a bra this time.”

“Please mistress, please let me try a pretty bra. I’ve never had a bra before and I would be so proud to have one from you. Please Ma’am, I’d really like to wear a bra over my sensitive sissy nipples…”

“Put your arms out.” I fasten the bra around him.

“Resume your resting position.”

Seeing him with his nose pressed to my boot wearing a bra and sissy ankle socks is making my clit buzz. Its such a servile pose for him and his obedience and begging is effecting me much more that I had expected. I give myself a few more gentle rubs before telling him to continue.

“Begin.”

Muffin begins firmly stroking his shaft up and down the bell jingling at every stroke. I begin firmly rubbing myself as soon as he begins. He can’t help but notice the noise of my juices and gasps of pleasure.

“Edge”

“That didn’t take long. Two minutes and fifteen seconds. You are at thirteen minutes and fifty five seconds. I doubt you’re going to make it to the end. Go ahead and beg for your panties right now.”

His voice was a little breathy since he had clearly been holding his breath and straining to make it even as long as he did.

“Please mistress, please. Please can I have a pair of panties. You know how much I love panties. If it pleases you this sissy would like to wear panties for you. Please, pretty please…”

I let him keep it up for well over two minutes rubbing circles around my clit and occasionally laughing at him as he begs. Finally I rub the panties across his chest before placing them in his hand.

He’s dripping pre-cum and was evidently very close to cumming from his last edge. I help him a bit as he puts them on, still blindfolded

“Resting position. I’ll generously give you an extra minute or two.”

“Thank you Ma’am”

It may have seemed generous, but after he spends five minutes listening to me rub myself he may think otherwise. I lie back on the bed and briskly insert my middle finger and then another and another.

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