Ok girls it’s time for another exciting assignment to challenge your inner girl. If you have time over a weekend then take this sissy challenge and make me proud! Of course I expect you to post all the dirty little details here for ALL to see. If you have . . . → Read More: Sissy Assignment – Plugged Stripper Sissy]]>

Be my Stripper Sissy

Ok girls it’s time for another exciting assignment to challenge your inner girl. If you have time over a weekend then take this sissy challenge and make me proud! Of course I expect you to post all the dirty little details here for ALL to see. If you have pictures even better.

I like to call this challenge “The Plugged Stripper Sissy in Training“. It will require you to have a “pussy plug” and if needed something to hold that plug in unless it’s inflatable and can be inflated to remain in the girl hole. If it vibrates even better! I love vibrating inflatable plugs. If you’re not sure what to get just email me here and I’m happy to help you.

You then need a trip to the drug store to purchase a disposable douche. You’ll need to make that girlie hole nice and fresh. It’s not rocket science to figure out how to use it. (wink) If you can hold it for 5 minutes it will make you clean and fresh!

You may want to get a little lube for the plug but don’t get carried away and let it slip out.

After your shaved and clean inside and out you’ll insert your pussy plug. Now put on your girlie attire including HIGH HEELS. If you don’t have a garter strap you’ll use your panties… you take 10 one dollar bills. You place them on the floor at your feet. You then need to put on some sexy stripper music and begin to dance. You need to really bump and grind those hips girls! Every 3 min you squat down really slow and sexy to pick up one of the bills. Rub the bill all over your titties and then place it in your panties. Do this every 3 min until the bills are gone. Each time you place a bill in your panties you’ll say “Thank you Sir!”

The object of this sissy challenge is to do this without the plug slipping out. You need to clinch those tushy cheeks tight and keep it in. If you successfully do the challenge then you are permitted to rub the clitty until you cum in your panties and all over your earn money! You then dry the money and the next day you take your 10 dollars and buy yourself a pretty pair of of new panties.

If the plug slips out then no squirty for you. You must take your 10 dollars and buy me an Amazon gift card to email josephine@enchantrixempire.com Next week you get to try again until you get it right.

Good luck girls!

If you’d like to read others post and network with other humiliated sissies hop over to my group “Humiliated Sissy” at www.enchantrixempire.com Once you sign up go to groups and look for Humiliated Sissy.

Or post your report below in comments. I love getting comments from my sissies!

Ask me ANY Question

Dear Goddess Josephine,

Should all sissies wear a chastity device and if so, what is good model that you’d recommend?

Also, how should a sissy be punished if he’s misbehaved – are self spankings given at a mistresses direction and with her watching . . . → Read More: Sissy Advice: should all sissies wear a chastity device?]]>

Ask me ANY Question

Dear Goddess Josephine,

Should all sissies wear a chastity device and if so, what is good model that you’d recommend?

Also, how should a sissy be punished if he’s misbehaved – are self spankings given at a mistresses direction and with her watching (possibly via webcam) appropriate?

Thank you,

Sissy Brad

Dear Sissy Brad,

Yes, I absolutely think that an owned sissy slave should wear a chastity device. This keeps the sissy focused and mindful of his place. He should never be permitted to touch his little clitty without permission. He should also be kept in a perpetual state of arousal making his service more enthusiastic.

I prefer The Curve-(click to see it here). Unlike the CB6000 it has more venting and openings to allow air flow (this additionally create arousal) and easier to keep the sissy clitty clean. When you shower you can simply use a blow dryer to remove moisture and keep from chaffing. I like this set because it also has the number serial tags. Once a tag is placed in the lock holes it can not be taken off without cutting it. When placed on a proper cock control inspection program this is very effective.

I also think the sissy should be plugged. Anal Plug Master (Click to see) If you click the link and look at the Anal Plug Master with inflatable butt plug, you’ll see a harness that holds a butt plug into the sissy hole. This harness can also hooked to the chastity device and insures that the butt plug can’t come out. The harness locks on so that the sissy can not remove the plug.  I like the fact that its inflatable and can be used as reward or sissy punishment.

Sissy Control and Punishments

I think that any owned property, ESPECIALLY a sissy should be on a program of punishment and reward. Personally I think its boring to punish a sissy just for the sake of doing it. I prefer always engaging the sissy in assignments where he earns reward or punishment. This creates such a wonderful dynamic between Mistress and sissy.

The worse punishment is denial. In no way will I allow the little bitch to control how I enslave him. When I give punishment and reward I do it REALLY and punishment can be physical , emotional or both. Even online and phone sissies are given task and must provide adequate reporting. I enjoy watching them on cam doing humiliating or cute task. I love the look on their face when they are being punished. I’ve had sissies spank themselves with wooden spoons and paddles while on cam, however if I’m not happy with the results I make them start over until they get it right. I want that little bitch’s ass to feel sore for at least 24 hours. Everything time he sits down he’ll think of  me!

Love,

Josephine

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I know you want to feel like a sweet little prissy girl, however the reality is that you need to be trained to serve ALL of your Mistress’s needs. If you’re going to act like a girl then you need to do EVERYTHING girls do. Of course most girls don’t get any special . . . → Read More: Preparing Your Pussy for Fucking]]>

I know you want to feel like a sweet little prissy girl, however the reality is that you need to be trained to serve ALL of your Mistress’s needs. If you’re going to act like a girl then you need to do EVERYTHING girls do. Of course most girls don’t get any special training when it comes to fucking. Hopefully she won’t encounter a monster cock her first time when she loses her virginity. Lucky sissy at least gets to “train” to accept things inside of his “sissy pussy” or “nasty little whore hole”. (Humiliation and erotic embarrassment are important for sissy training )

This lesson is preparing and making sure that when mistress (or one of mistress’s friends) wants to fuck you, you’ll be able to take it without a problem.

Butt Plug and Harness

The training device I use (see above image and click to purchase or read more) is a butt plug (pussy plug) and harness. It firmly holds the plugs in place.  You can start with something small and then work your way up. Do not use baby oil. Only use a water soluble lubricant. The one I really like is “Astroglide”.  Be sure to keep that girl hole douched!

Insert and adjust the harness so it fits snug and keeps the plug firmly inside. Make sure you can bend, squat and move about freely. I normally make sure all my sissies are plugged on a regular basis to make sure they never tighten up. You can increase the size for training purposes and for daily wear swap down to a more comfortable fit.