I knew Jim was not your average kind of guy. I knew he would make the perfect office sissy the day he got hired!

Jim just had this way about him. The way he walked. He just had this natural sway to hips and when he would hang out with us ladies, he just fit in so well.

Jim was one of the girls, he just didn’t know it yet!


The Idea


So me and some of the ladies at the office had a great idea. We decided to have a girl’s night and we were going to invite Jim. This was just the start of making him the office sissy.

We planned on having some wine and just relaxing. I even hired a friend of mine to come in to do makeup and nails! We also picked out some cute outfits, along with some sexy panties and heels.

I asked Jim his shoe size during some casual conversation and let me tell you, he has small feet for a sissy to be *giggles*. I can’t wait for girl’s night!


Operation Office Sissy


The big night has arrived! Jim showed up on time and was so excited that we included him. He had no idea how much his life was going to change for the better.

We sat around sipping our wine and just having girl talk. I wanted Jim to be super relaxed (if you know what I mean). Once I knew the wine was hitting Jim just right, I decided to really get this party started *giggles*.

One of the ladies started bringing out all the cute outfits and things. I could see the gleam in sissy Jims eyes just looking at all the pretty frilly things before him. He complimented each piece and would touch them saying how soft they were.

I said, “Imagine how soft and wonderful it would feel against your skin!”. Jim blushed, but I knew we could get him into these cute outfits.


Let the Transformation Begin


Jim started to undress out of those icky man clothes. I held up 2 pair of panties for him to choose from. One pair were pink satin with lace and very girly and frilly, the other pair were a sheer black thong with a few little rhinestone embellishments. His choice will determine what kind of office sissy he is going to be!

Of course, the inner girly in him chooses the pink satin ones. He slips into them and looks in the mirror and starts turn slowly, he can’t believe how amazing the satin feels against his skin. He even let out a little giggle.

We picked out a cute pink frilly short dress….., very frilly, but I think he liked having more satin caressing his skin. Jim was beaming with joy, he even sat like a lady so we could slip on his patent leather mary jane heels. He is the cutest office sissy we’ve ever seen! but we were not done yet.


Finishing touches


Time for hair and makeup! He got to choose what wig and color he would like and he chose the light brown should length wig with the soft beach waves. He looked beautiful.

My friend styled his wig a some and then started to paint his face with shades of pinks and reds. she even added some long, luscious lashes and his nails were painted a candy apple shade of red.


Jim couldn’t believe how much he felt like his true sissy self after coming to our girl’s night. I told him he is now our office sissy, and we are going to have so much fun with him. He will be assigned tasks around the office and some naughty tasks after work hours *giggles*.


Stay tuned for a follow up blog about the after hour adventures of sissy Jim.

Jim was a frilly sissy, what kind of sissy are you?

Let’s figure it out together in a session via phone, text or skype! If you have any questions, please feel free to email me!


Masturbation Domination Goddess Madison


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