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The Plan.....

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By (user no longer on site) OP   
over a year ago

On new years eve we went out with James, Sarah and Ben. James and Sarah had recently split up but had been a swinging couple before. Ben is bisexual and has a profile on fab but I haven't told my Mistress/Cuckoldress/Girlfriend that I've seen his cock. Now nothing actually happened that night between any of us.

We're all friends but other than knowing I'm a crossdresser they don't or rather didn't know our personal life. Something might have happened as my Mistress did actually hook up with someone but Ben inadvertently cock blocked her. This led to her later telling him that I'm fine with her being with other guys. I don't think though that she told him about the humiliation. Someone however is going to find out about that humiliation and Sarah has given her full blessing. James is all part of the Plan.

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By (user no longer on site) OP   
over a year ago

So we already knew that James is a crossdresser although we are yet to actually see him fully dress in public.

However he says that's 'the nights I get to be a slut.'

Mistress put it to him that perhaps he had a humiliation kink and that she could help him with that. The next day he was texting her addressing her as Mistress. Due to life, illness and kids we've not been able to play with this until we....well she came up with the plan. If James wanted to be her submissive first he would have to see what the roles the job called for.

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By (user no longer on site) OP   
over a year ago

So I can't tell you the plan as that would only ruin the story. I can tell you that up to now is true although names have been changed. I can also tell you that a lot of what is to happen depends on the choices of Mistress and the actions of myself. It is I that has to show what is expected you see.

Firstly I needed to go shopping and we needed to invite James out for a drink and then see where the plan took us.

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By *j and c 2Couple
over a year ago

mullingar

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By (user no longer on site) OP   
over a year ago

So shopping is easy when you have a list especially one created by your Mistress. A cute piggy outfit which really was little more that a lingerie set, pig butt plug, pig mask, pink heels with a bow, some pink fishnets and a pink party dress. I could see a theme going on here but yet to see where the plan was going. She messaged James to arrange a night out however I also had work.

"No worries" she said. "We'll meet you after work and you can change into some of it at the end of your shift."

It's not the first challenge I've been set and usually on our nights out I have to walk back exposed. I wondered to myself was this all part of the plan?

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By (user no longer on site) OP   
over a year ago

So the day arrived and Mistress ordered me to have a bath and get rid of my body hair. When I got out of the bath Mistress towelled me dry before then putting on my chastity cage.

"I've packed your bag for you. I will message you some instructions ."

"Yes Mistress" I answered meekly as I put what she had left for me on the bed. Fishnet tights that I was to wear under the lingerie set. Boringly though was jeans and t shirt. I know what you readers was expecting was for me to wear the dress but I can only imagine that was in the bag. Long pair of socks and nobody would know what I was wearing underneath my uniform.

After I got dressed I left for work. The plan was starting to unfold.

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By *ceman619Man
over a year ago

Sunderland

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