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My Boyfriend's Complete Feminization

As you may recall from my earlier story Coed Mistress's First Experience With A Sissy Boy, I came home to a very interesting surprise from my college boyfriend of 3 months. Who could have guessed that my surprise was not just roses and a box of chocolate, but something much more intriguing? How many of my sorority sisters could ever say they walked in on a sissy girl in the making?

So when my last story ended, my boyfriend had just stood up in front of me, wearing nothing but a matching bra and panty set that he had found in my lingerie drawer. How sweet he looked in the pink and purple ensemble...but something was truly missing.

As I sat there looking my boyfriend over, it came to me that perhaps I should give him a bit more of a makeover. Maybe I was cut out for this feminization Mistress bit after all!

I was enjoying the blush on his cheeks as I stood up and led him into my bedroom. My room, mind you, was the ultimate picture of all things feminine and girly. This was the perfect room to turn my boyfriend into a pretty little bimbo sissy girl. Resistance to my transformation of him was completely futile, and he knew it. I sat him down at my makeup table so he could look at himself in the large mirror while I sorted out a few things.

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Sissy Boyfriend Gets Feminizing Makeover

Now let me set the scene here. My bedroom was doused with an abundance of pink and frill. The soft pink walls were covered in pictures that would make even the manliest of men let their minds drift to all things soft, silky and feminine. A large four-poster bed sat in the middle, complete with a fluffy pink and white comforter and sheer pink canopy. One wall was lined with shelves of heels that would make any girl wet with excitement, and the carpet was white with pink hearts. My boyfriend’s mind must have been reeling when I finally returned from my closet. I tossed the clothing on the bed before he could see what I'd picked out.

I pulled my desk chair over to the makeup table and turned him around to face me, again with my mischievous smile giving away my naughty plans for him. When I reached over to grab my foundation, he looked at me with his eyes wide open.

"W-w-what are you going to do to me?" he asked, squirming in his seat.

I just smiled and told him he better sit still like a good sissy boy. I could feel myself transforming into a sensual but strict mistress right before his eyes. I giggled quietly as I started to slowly apply the foundation to his face. He, on the other hand, sat there in total shock.

I made sure to put on a heavy dose of eyeliner and a thick swipe of eye shadow before I reached for the blush to dab on his cheeks. I sat back admiring my handiwork and pondering for a moment what this sissy boy was missing. Ah-ha! The missing touch was simple...bright red cock sucking lipstick.

I stood up quickly and grabbed his hand pulling him to his feet swiftly, then twirled him around to look at himself in the mirror while I grabbed my camera!!! He stood there looking into the mirror in awe; he was slowly turning into a real sissy girl. I saw him touch his face very lightly, so as to not smudge my artwork, but to assure himself that it was, in fact, his face he was staring at in the mirror.

I told him to turn around and face me. I already had the camera to snap a picture, and in a swift click, I had captured not only the image of my feminized sissy, but also the look of shock and awe on his face!

An Outfit Made For A Sissy Slut

I grabbed his hand, half-pulling him over to the bed to show him the outfit I had picked out for his special upcoming moment. It was a tight pink micro-mini skirt, and a sheer white top to show off his pretty bra to our guest who would be arriving soon. I told him to get dressed while I walked over to my shoe wall and picked out some super-hot 6 inch pumps, also in bright pink.

As I was walking back over, I took a good look at this poor sissy boy, just about to start his sissy training standing, somewhat awkwardly, before me in the outfit I had told him to wear. Perfect!

I handed him the 6 inch pumps, and he looked at me with his mouth agape and his eyes practically bulging out of his head. “I...I can’t walk in these--" he trailed off yet again before finishing the statement as I glared at him.

He knowingly took the heels and sat on the bench at the foot of my bed. Once he had the shoes on, I told him to hop up and practice walking for me. He stood up, wobbling in his new shoes before taking a few duck-like steps. I walked over and gave him a slight pop on his ass, making him to stand up straight.

"Now, try again with more grace," I commanded, my excitement over his transformation into a coerced cock sucking slut growing exponentially.

Just as he was getting the hang of walking in the beautiful high heels, there was a knock at a door. I just smiled as he froze mid-walk, turning to face me with a look of sheer fear and complete shock in his eyes.

"I have a special prize for you tonight," I laughed, then stood up and headed out to answer the door.

I stopped at the door of the bedroom and beckoned for him to follow me. He hesitated at first, but then I gave him a look like only a strict Mistress could. He was almost instantly on my heels.

Wondering who was at the door? Head over to the third and final installment of my story, From Sissy Slut To Coerced Bi Slut to see how this story ends!

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For sissification and feminization phone sex sessions, visit us at Sissy School, or call us Toll Free from the UK at 0-800-014-8421. We look forward to helping you bring out the Sissy inside!