Tormented Sissy

Silly Little Sissy

You’ve made sure to shave, scrub and moisturize every square inch of skin. You gave yourself an enema a few hours before and have been careful to eat lightly since. You have spent hours picking out which pair of panties to wear to our meeting, and which to change into. You have prepped your new sissy outfit, making sure it’s folded nicely and packed away for transit. You have your new plug wrapped lovingly in tissue. It’s a size up from the one you usually wear, and are hoping to surprise and impress Mistress with your new ability. You also have a spa gift certificate for her, wrapped with a bright red ribbon tucked in the side of the bag. Even though you have been seeing her for twice a month, you still get nervous as you prep for our time together.

You ring the bell at your appointment time and are let in by Her assistant. You hadn’t known there was going to be a third person. You have no idea what to expect. After you remove your shoes, Her stunning assistant walks you to the cage and locks you away, instructing you to take off your male costume and push it through the bars of the cage to her. Standing naked, except the panties chose to wear for the trip over, you cast your eyes down as you feel her assistant giving you the once over. You hope she approves, and even though humiliated, your dick throbs against your panties.

“You should get that clitty stick under control before she sees it. Not very ladylike you know.”

You try to will it away and shove it between your legs, to get that perfectly flat feminine panty line, but the more you push it, the worse it gets.

“She’s going to be here in two minutes. You are going to be punished if you still have that problem.”

But it’s too late, you hear the click, click, click of her heels approach. The terror of Mistress seeing your erection, and the site of her busty assistant laughing at you makes it makes it throb and a tiny bit of pre-cum oozes out and wets your panties just as Mistress walks up to the cage.

“Looks like a slutty little sissy has wet her panties. You know that means I’m going to have to torment that useless thing. How are you supposed to be the perfect little sissy if that bulge is ruining the effect.”

“Please Mistress, you plead, I will try harder, it’s just that you haven’t let me cum in almost a month!”

I don’t care if I haven’t let you cum in a year, I don’t want to be greeted by that pathetic thing staring at me.”

You are told to slide it through the bars of the cage, and she gives it 5 good slaps with the riding crop. While the crop stings, the softness of her hand holding it in place negates the effect of the crop and your erection continues until she gives you 10 more.

Smiling, she looks down at your limp former manhood. Much better. She slides a chastity device over your soft cock and locks it in place and drops the key down her cleavage.

She instructs you to put on your sissy outfit for her and she will return for you. She wants to demonstrate your cock sucking skills to her assistant. Just the thought makes your cock once again attempt an erection, straining at the device. You slide into your new outfit, but the silky sensation of the garter belt adds to your chastity discomfort.

As you slide your pink stocking clad feet into your heels, and kneel in front of the cage door, you know more punishment awaits, because the moment she slides those crinolines up, she will see, that the punishment and the chastity did nothing to stop your erection. It’s only made it more uncomfortable.