Tuesday, June 26, 2012

My Sissy Assistant -- Part 1

After my husband ran off, I started having awful problems with the rotten stepson I was left with. I travel a lot on business (I am a fashion buyer for a famous department store) and he was getting into all sorts of terrible trouble when I was away. A friend suggested that I have him feminized because sissified gurly boys are so much better behaved.

Well that's what I did.  I sent away to have him transformed.  It took about a year and the results were amazing. Not only did I now have a cute, feminine "stepdaughter," but he was now completely obedient and compliant.  He would do anything I said without any reservation or complaint.  He was completely broken.  I understand that he had been subjected to some rather strict behavior modification during his year long conversion.

I was, of course, delighted. I could now leave my femmy stepson at home while I traveled without worrying.  When I would return home from a trip, my home would be spotlessly clean and he would greet me with a delightful little curtsey to welcome me home.

During one particularly busy period, I was falling behind in my paperwork and I asked my Sissy stepson to do some filing in my home office.  He did it perfectly.  I soon had him keeping track of my appointments and filling out expense reports for me.  I suddenly had my own personal Sissy Assistant!

I decided to take my Sissy with me on a two-week west coast trip and it worked out wonderfully!  No one was surprised to see a senior buyer like me followed around by a sweet little assistant.  But of course, my Sissy had to dress the part.  So I bought several fashionable outfits for him to wear.   Here are a few of the dresses I had him wear on his first trip with me as my secretary.  Doesn't he look adorable!

I knew he hated it, but he was too well trained to complain.  At first, I know he was scared that someone would find out that he was not a pretty girl but actually a sissified boy.  And I constantly threatened him that someone would figure out his secret unless he behaved with girlish perfection.  But of course, his feminization was so complete that no one would ever guess he wasn't a girl -- unless you pulled down his panties.

Monday, June 18, 2012

Afternoon Sissy

Whenever I am home alone, I love playing dress-up.  I raid my mother's closet, her lingerie drawer, her make-up, jewerly, perfume -- everything.  She even has a long curly wig that I use to complete my look.

I love dressing up like a girl.  I feel so feminine, so free, so alive.  I love getting my make-up perfect and slipping on the wig.  I especially like wearing my mother's sexy lingerie.  Dressed like this, I enjoy staring at my pretty reflection in the mirror looking back at me.  Sometimes I take photos of myself, like this one, that I can look at late at night when I'm in bed.

But today, disaster struck.  I had the house to myself all afternoon -- I thought.  My mother was at work and my older brother was at football practice.  I was all dolled up, wearing my mother's light pink, lacy nightgown.  I was in the living room, dancing to the radio and watching my performance in the big mirror, when all of sudden in walked my brother and three of his friends from the football team.

"What the fuck!?!?" my brother shouted wen he saw me.

"Who's that?" one friend asked.

"That's my faggot little brother," he answered.  The other boys howled with laughter when they recognized me.

"He sure is pretty," the biggest of the friends said.

"Hey," another one said. "Even though practice was cancelled, I think we can still get a workout this afternoon, if you know what I mean."

"Go ahead," my brother said.  "I don't care.  Do whatever you want with him."

And with that, the three boys dragged me upstairs to my bedroom to be their "Sissy Girlfriend" for the afternoon.  Thet took turns having sex with me while the others held me down.  I tried not to cry, but they were really rough with me and it hurt a lot. 

When they were done with me, one of them said that I was cute enough to be a cheerleader -- and if I was a cheerleader then I could get fucked by the boys on the team all the time.

Hmmm.  Maybe I will...