Tag Archives: Sissy

Who Is The Boss Now?

Everyone knows how much I love to role play. I love to assume roles of all kinds. But one of my favorites is being your sexy assistant. Just think of all the naughty, kinky fun we could have.

Lets say you are working from home, and you forgot something at the office, so you call me to bring over the files you need. I tell you that I’ll be there after lunch, but as it turns out, it would really work out better if I brought them over right now. I don’t bother to call you back and let you know I’m on my way. I figure you’ll be happy to have them sooner rather than later, anyway. Using the key you gave me, I walk inside the house and into your home office. You are nowhere to be found, so I just place the files on your desk and am about to leave when I hear a loud noise in the back of the house. Concerned about your safety and being a very good assistant, I walk down the hall to check it out. Your bedroom door is open and I peek in. There is a lamp knocked over, (the noise I heard) and you are dancing around in a sexy little panties and stockings! You’ve got your ear buds in and have no idea that I’m there. Just imagine my surprise to find my big manly boss is a little sissy cross dresser! *giggles*

I take my phone out and start taking some pictures, when you turn around and see me. You are so shocked and embarrassed – but turned on too! I can see that cock getting hard in those silky red panties. I walk over to your nightstand – certain that I will find something fun in there – and pull out a big dildo. Now, I’m gonna show you what happens to little sissies who crossdress during business hours! Who is the boss now?

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Cross Dressing Phone Sex

Get over here, you little cross-dressing phone sex whore! I know that just underneath your manly, rugged exterior, there is a little sissy bitch dying to be feminized by a woman like me. You dream of being taught how to be a proper little bitch, so when you’re all alone, you go in your bedroom, lock the door and give me a call for some intense sissy training phone sex.

We’ll start with some humiliation, because I need to remind you that you are nothing but a tiny dick faggot, and that because you are so hopelessly pathetic, you were destined to dress like a slut and take cock.

Then I’ll order you to draw yourself a bubble bath, and shave off all of the hair on your body. After you’re smooth, you need to put on the sexy outfit I laid out for you: Red, lacy panties with a matching bra. A short, tight black dress. Thigh high stockings and a pair of 6 inch stilettos.

I’ll do your hair and make-up, and then we’ll start on your walking lessons. Every sissy needs to know how to swing her hips and parade herself like a hooker.

As soon as you’ve mastered the slut walk, you’re going to really put it to work. I’m going to turn you out on the streets and you will turn tricks for me as the sexy new she-male on the block. The guys will love you. You will be irresistible. You will suck and fuck so much cock. You’ll have no problem reaching and exceeding the 12 cum load quota I set for you each day!

Cum Eating Phone Sex Faggot

Calling all cum eating phone sex faggots! Let’s get our kink on, and show me what a horny little slut you really are! Is your sissy whore hole aching for a big juicy cock? Do you want to be my bukkake slut? How about setting up a full on gang bang? I know lots of guys that would love to get a taste of my newest sissy fuck toy. The more, the merrier, right? HaHa!

I want to get you pumped full of cum. Give me the control to put you in your place, on your hands and knees, where you belong! All you have to do is admit what a dirty little skank faggot you are down deep, and confess to me just how much you want to be whored out by a trashy mistress like me, and all your kinky dreams will cum true.

Breaking In My Sissy

You’re going to be a good little whore for your Mistress tonight, aren’t you. You and I have both been waiting for this night for a long time. I’ve been training you to be such a proper little sissy. Dressing you up, teaching you how to do your make up, and instructing you how to practice with toys, until you were ready. Really ready to put it all to the test. And finally, tonight is the night! You’re going to get your first taste of big, juicy cock!

You are about to become my true little sissy cum slut. Being my sissy cuckold is what you are destined to be. You get so turned on dreaming about being my dirty clean up bitch, and my cocksucking faggot, don’t you?

Well, we’re going to see how much of a whore you can actually be because I’ve arranged for quite a wild night. I sent out a message to everyone in my contacts that I was breaking you in tonight, and they should show up here any minute for a taste of my newest little fuck whore. Tons of guys are going to be here, and you’re going to show them a good time.

I know you must be excited! I can see your sissy clitty getting hard just thinking about being my dirty sissy slut. Are you ready to suck these boys off, and taste their gooey, stick cum? Don’t forget to make eye contact while sucking that dick! Are you ready to lay on your back, with your legs spread, and invite them, one right after another, into your sissy pussy? Remember to grind up against them, pulling them into your slut hole as far as they can get!

Good! Then get on your hands and knees in front of the door, so your slutty little ass is the first thing they see when they walk in. I hear a car pulling up now!

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Ass Eating Sissy Slut

I know that you’re nothing but a fucking sissy boy slut. I know you want me to use and abuse you like the piece of trash you are! It makes you so hot to be such a skanky slut for me. And I’m going to make you prove just how well trained my little cum whore is tonight during the gangbang I set up!

I’m going to make you fluff every cock that shows up tonight. You’re going to be on your knees, dressed like such a little sissy fuck whore, sucking cock after cock! And then you’re going to lay down beside me, and get fucked! We’re both going to get pounded by nice thick shafts until we’re completely full of cum. But even as the last guy pumps you full of jizz, we’re not done yet, because I have something else in store for you, my filthy sissy!

I know you crave the taste of cum. You will do anything and everything to get it, won’t you? You don’t care if it is straight from the cock or if you have to suck it from out of my dirty, gaping ass. Well, at least that’s what you’ve always said, but we’re going to test that last part tonight, because I am going to make you get down on your knees and clean my stretched out, sloppy, filthy fucking ass. You are going to prove to me and everyone else that is watching what a dirty little sissy whore you are, and slurp the cream pie straight from my nasty asshole! Lap up ever last dirty drop of that salty jizz, you ass cleaning little sissy slut! 

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BBC Cuckolding

I always get a kick out of cuckolding phone sex. You don’t have to explain to me that you have a tiny dick. It is pretty much a given when a phone sex sissy like you wants to talk about some big, thick stud fucking your wife. Don’t you wish you were as well endowed as he is? Don’t you wish you could make your wife cum as hard as he does?

Well, you aren’t and you can’t, and there is nothing you can do about it. So you have to wait at home like a good little cuck, while she goes out and finds a REAL man to bring home to do what you couldn’t even begin to.

While you’re waiting for her, you watch the home videos you’ve made of her with other lovers. That clitty of yours gets so hard watching her get fucked, doesn’t it? And you know it is just a matter of time before she comes home with a new toy to play with. You know just the kind she’ll bring home, too. He’ll probably be young and black, with at least an 8 inch cock. That seems to be her type.

She’ll want to degrade you in front of him. That seems to turn her on the most. And since it is the only way you can please her, you’ll happily comply when she orders you down on your knees to fluff her new BBC fuck toy. You’ll do anything she demands, because you know that if you’re a good boy, she’ll let you eat that cream pie. And if you’re really lucky, she might just let you put your cock in her pussy after he has filled her cunt with his salty cream. It doesn’t matter to you that the only reason she does is because she wants to humiliate you more, teasing you about how she can’t even feel you inside her freshly fucked cunt. He stretched her out so much, and you’re just too small. But you like it better that way, anyway, don’t you?

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Glory Hole Slut – Glory Hole Phone Sex

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It’s okay for you to admit to me that you love glory hole phone sex. I have been to the booths in the back of the adult book store a few times myself. Not actually sucking or fucking the stranger cocks that poke out from behind the wall, but I’ve been there to encourage a few sissies that were a little to hesitant to go on their own.

I’ve noticed that when you walk into the room, you can always smell the scent of old sex. The stale, pungent odor of sweat and semen seems to radiate from everything. And sometimes the floors are so coated with jizz that your shoes stick to the floor. Most people would be so grossed out they wouldn’t dare to step foot in a place like that, but to cocksuckers like you, that’s part of its filthy charm, isn’t it? I mean, after all, you are looking for a downright dirty encounter, and if that doesn’t fit the theme, I don’t know what would.

I want to hear about all the naughty things you do in those video booths during our glory hole phone sex call. I think it is really hot to hear how got down on your knees in that dark, nasty room and sucked whatever the cock of whatever man decided to use your whore mouth. I want to hear about how you dressed, and if you were a good little bitch for the men that wanted to fuck your tight, puckered asshole. I want to know how many men you made cum, and where they came at! Or, if you need someone to encourage you to be the filthy little cum slut that you know you can be, call me and I’ll encourage you to go in there and take it like a good little faggot ought to.

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