Then we will take turns sitting in the bachelor chair, and YOU will do a lap dance for awhile. You'll have to wiggle your slutty ass, wobble around in the high heels, bounce around on your plug, squat down and open your legs and rub your hands all over your thighs and up the tops of the stockings.
Good morning my slut,
Welcome to a long week of pantyhose and lingerie torture combined with the worst, most humiliating chastity enforcement program ever.
What a way to start the day, don’t you think?
It occurred to me this morning that you have been far too macho lately, far too masculine, and I have been extremely easy on you with regards to cock control, panty training and chastity. You cum too quickly, you masturbate on a whim, and you don’t even get hard anymore when I slip you into black french cut panties.
I think you need a little re-training. And after some thinking about it, I have come up with a week long plan to really straight you out (so to speak) and also fulfill one of my hottest fantasies about humiliating you in front of beautiful women who are total strangers.
But before you read this email, you must go into your briefcase. I have hidden a pair of black sheer pantyhose in there. You will use the pantyhose to bind up your cock and balls very tightly, spreading your balls apart, making that dick that belongs to me completely stiff in your panties.
You’ll feel the sheer material trussed around your ball sac all day and constantly be reminded of me. I’ll be binding you exclusively with pantyhose, stockings and panties (for gags) all week long to remind you that you are, first and foremost, a SISSY WHORE.
And as if that isn’t enough, your dick will get no relief. You came last Tuesday, and that will be the last time for a long, long time.
But don’t think you won’t be close a few dozen times…
**
Ok, panty boy. Are you ready for the long week? Are you sitting there in your big leather chair, naked from the waist down except for those tight panties and your balls pumping and pulsing with the pantyhose wrapped tightly around? To make sure you are doing a decent job, I demand pictures. I have put my digital camera in your briefcase also, so I expect a set of pictures in my email box by noon. Make sure I can see the flesh of your ball sac pulled tight.
And if that isn’t enough, I might make you start hanging weight from your ball sack, making you sit on the very edge of the chair and tie your stapler to the pantyhose and let it slowly sway back and forth.
Oooh, now isn’t that hot. It’s enough to make me want to come down and sit on the edge of your desk and reach out with my high heel, giving that dangling stapler a little shove to get it really swaying.
I’m in a sadistic mood. You will suffer for me all week, suffer to get me off, to make me wet. And by the time Friday comes, you will be begging for release. Because every night I am going to sit on your face and play with your nipples under your bar, every night I am going to ride your face to orgasm and smear my juices on you but give you no release at all.
I’ll lock your cock and balls in a tight metal chastity device by Wednesday, one that will not even allow erections. You will piss sitting down like a sissy girl, and wear pantyhose during your power meetings and hope no one sees the bulge in your crotch when you stand up to present.
Such a fucking pathetic little sissy! I know your pussy will be wet, and so tight, and ready for fucking by Friday. You will beg me to violate your slut hole, and I will give you what you need.
But only after humiliating you in the worst possible way. In front of beautiful women. In front of total strangers.
I get wet just thinking about it. My creamed panties might make their way down to your office for you to clean them out with your mouth and return to me at the end of the workday for inspection.
Do you want to hear what I have planned for Friday?
**
On Friday night you will wear a new, tight pink teddy with pink panties and white thigh high stockings with garters. The smooth, thin pink plug will be firmly in your ass, and possibly locked on with a butt plug harness, I have not yet decided.
You’ll wear pink toenail and fingernail polish to accent your outfit, then be allowed to put on some bluejeans and a nice shirt, and prepare yourself to look stunningly handsome for our night on the town.
I am having a limo pick us up at 10pm. I will be wearing a skin tight elegant black dress with gloves, my hair pulled up in a high ponytail. I will be dressed to kill and you’ll be my stunning escort.
We have reservations for a night of entertainment at Carmichael’s. You do know what that is, don’t you slut boy? It’s the premiere strip club in San Diego. We will take a drive down the coast and I will lead you into the club by my pinky underneath your collar.
Inside you will find the most beautiful women in the world stripping to the hottest dance music, and we’ll be sitting right in front. You’ll keep your hands down and behind the chair unless I order you otherwise, and I’ll make my way around selecting some of the most sexy ladies for your humiliation in the back room.
I’m sure many men will ask me if I am one of the ladies stripping; that happened the last time you and I went to a club. Of course I’ll just tease them by stroking a finger under their chin and showing off my ass as I turn and walk away, telling them I’ve got pussy on the mind, not dick.
And pussy I will find. I’ll be picking three ladies for a private showing in the backroom, sissy boy. And you’ll have to deal with the humiliation and fear when they see just how you are dressed underneath those macho, macho clothes!
**
You know I have been increasingly bi-curious lately, and so this night will give me the chance to explore a little pussy for myself. I will have my toy bag with me in case I get into a full-on scene with one of the ladies, but my main goal for the night will be to sit back, pleasure myself, and watch the ladies laugh and giggle at you when they unzip your pants and reach down.
But first you will have to tell them.
We’ll go the back and they’ll put you on the bachelor chair in the center of the room. By then I’m sure you will be rock hard, because I will have ordered many lap dances at the start of the night, and tipped the girls extra to shake their ass in your face and make you stick your nose in their crack to lick the back of their thong. By then they will already be calling you “ass boy” behind your back.
In that chair you will be forced to remain silent as I mingle with the ladies, sipping champagne. I have already decided I will choose a blond bombshell with huge tits, a very sexy, alluring dark brunette or perhaps Asian sex machine, and a red head who just LOOKS like she is femdom. And you know how gorgeous they will all be.
And I’ll also have three thousand dollars in cash to ensure we have a very nice time. Taken right from your savings account, of course!
This may take some time, because I plan to enjoy myself with the ladies while you squirm in your chair, dreading the moment that they will find out this sexy, masculine man is in a pink teddy underneath his clothes.
Maybe I won’t even tell them until I go into the toy bag and pull out your sparkly high heel pumps! And when they squeal with delight and grab them to see if they are for one of them, they’ll realize how big they are, then look at you, and burst out laughing.
Or maybe I’ll make you tell them. I’ll say, “Ladies, my boyfriend here has something he is dying to tell you. Go ahead dear. Tell the ladies.”
How will you word it? Will you just blurt it out? “I’m wearing panties. I’m a total sissy. I’m in a pink teddy with stockings and I haven’t cum in two weeks. I’m pathetic.”
Oh, to watch you squirm in the chair and watch these lovely ladies smirk at you will be sheer pleasure.
Then, to watch you stand up and slowly strip. How ironic, stripping for strippers! You can bet we’ll all laugh at you and it will be my bright idea to make you STRIP like a real slut, having to flaunt your manly body as you do it, looking like a Chippendales male dancer at the start, and ending the routine looking like Miss Priss of 1999!
You’ll then be standing there, humiliated, your panties bulging, as I have the ladies investigate you. That’s when I’ll tell them about your chastity program, and about the plug in your ass.
You know how the odds work. Odds are, one of them will be femdom-curious, or a full fledged domina. That’s when the toys will come out. I wonder which one will put on my strap on and fuck your ass while we watch? Who knows!
Then we will take turns sitting in the bachelor chair, and YOU will do a lap dance for awhile. You’ll have to wiggle your slutty ass, wobble around in the high heels, bounce around on your plug, squat down and open your legs and rub your hands all over your thighs and up the tops of the stockings.
How humiliating. I can’t wait to see you try to pull it off.
**
Of course, I can’t predict how the night will end. Maybe one of the ladies will join us in the limo for a drive around the city. Maybe I’ll tie you up and make you lay on the floor while the ladies take turn sitting on your face. Maybe I’ll show them all how to dominate sissies.
I’ll have the camera though, and I intend to get some pussy.
You will never cum, that’s for sure. You’ll be brought home and caged up and maybe I will let you sleep in the bed.
I’m sure you’ll be exhausted. So you had better prepare yourself all week long for a very long night on Friday. I am going to make you really suffer.
Affectionately,
Mistress Akasha
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