Tag Archives: Crossdressing

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?


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!

Whoring Out Your Husband

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Do you suspect that your husband is a little sissy? Have you caught him masturbating into your panties? Well, I know for a fact that your husband is a faggot bitch that thirsts for real cock! He’s such a little sissy phone sex slut. He calls me after he’s dressed up in your lingerie, and wearing your make up to tell me all about how he wants to get down on his hands and knees to suck off a BBC while I pound him from behind with my thick, veiny strap-on! Then he gets really kinky and confesses to me that he wants to be tricked out, taking on dozens of strange cocks a day just to fatten up my bank account. He’ll get a cut of it, of course, but only enough to buy new sexy outfits to show off for his johns. After all, we don’t want him wearing yours forever. Yours are sort of outdated and not nearly as whorish as I prefer anyway. But what can I expect from a boring old hag like you?

I think it’s a great idea to pimp him out. I mean, if he’s already dressing like a little fuck slut, sucking and fucking cock, he might as well make me some cash in the process. I just can’t decide how to do it. I mean, there’s craigslist, of course, and street walking. Even on a slow night that could bring in a good chunk. I could also put him up in an adult book store, in one of the video booths, and have him ready and waiting by one of the glory holes. Maybe we’ll just do all three. Variety is the key to any successful financial venture, right? Oh, and affordability. That’s important, too, so we’ll make sure he’s a cheap whore. $10 for the guy to pop his load in his mouth, and $20 for full service with that little sissy bitch sounds reasonable, right? Hahahaha!

If you want to become one of Jamie’s cheap whores, call now!

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