Custom Ordered Sissy

For the Sissies that I transform for my own fun and amusement, I typically go for a slim, slinky look.  You know, teeny little waist, skinny arms, long lean legs...Mmmmm.  And with this look, I usually go for feminine, lady-like bosom, a B-cup or maybe a C-cup. 

But when I get a custom order for a Sissy, the buyers almost always seem to want really, really big boobs.  Well, the customer is always right -- and I don't disappoint my customers!

Sissy Angelique came to me voluntarily three years ago.  He wanted to be transformed into a pretty girl and had dreams of opening a beauty salon.  Well, half of Sissy Angelique's dreams came true; he is indeed very, very pretty now.  As for returning home to open a beauty salon, well, that was never going to happen. 

I had an order for a Sissy with really big tits.  And I saw that Sissy Angelique had the right physique to look awesome with an enormous rack.  Of course, he totally freaked out when I told him what I was going to do to him.  But by then it was far too late for him to regain any control of his fate.

My client was delighted when I presented Sissy Angelique -- and those huge boobs -- to him.

And now, everywhere Sissy Angelique goes, he attracts stares and lewd comments from men and disgusted looks and derisive comments from women.  And his Master delights in showing off his Sissy's majestic boobs in public, allowing his Sissy to wear only the skimpiest, most revealing tops.  Sissy Angelique begs his Master to allow im to wear a bra and to cover up his massive tits.  But why would his Master agree to that?

Young Sissy Created for Older Men

Stepmother was so excited!  Tonight, Sissy Suzette was going out on his first date -- with a MAN!

Sissy Suzette's cruel stepmother, Mildred, had been transforming her stepson Stanley from a normal teenage boy into a feminized plaything for older men.  Two years ago,  Stanley/Suzette's father ran off with another woman, leaving Mildred to care for Stanley on her own.  She decided that she would take her revenge on her husband by destroying his only son.

And so, after two years of hormones, strict training and brainwashing, it all came down to this.  Poor Sissy Suzette!  He is so terrified about being sent on a date.  He was close to tears this afternoon as Mildred helped him with his hair and make-up.   

Mildred had posted Suzette's profile on Match.com, including some sexy, glamourous photos.  The profile said Suzette was 19 years old -- and that she was interested in dates with much older men.  Well, within days it seemed like millions of men in the area eagerly responded.  Mildred was delighted when she discovered that she could subject poor little Suzette to a limitless number of romantic encounters with different men.

Mildred carefully selected outfits for Sissy Suzette that were both sexy and classy.  A rigorous diet cimbined with a little padding in all the right places gave Sissy Suzette the alluring shape of a pretty young woman.  And with relentless training, Sissy Suzette could now talk and sit and eat and walk exactly like a girl. 

It was time for Sissy Suzette's first encounter.  The date was arranged at a french restaurant downtown.  Mildred sat at a nearby table and enjoyed the show!  Suzette's date, a 50 year old executive, was practically drooling throughout dinner, ogling the pretty young thing sitting across from him.  Sissy Stanley flirted with the older man as his stepmother had trained him. 

Watching the bizarre scene unfold was getting Mildred excited.  She even felt her panties become damp as she saw Sissy Suzette's date place his hand on Suzette's stockinged knee under the table.  This was going even better than she had hoped!

When dinner was over, Mildred followed the pair out to the parking lot where the two were passionately making out, the older man pressing her stepson against the man's BMW as he aggressively kissed the pretend girl.  After a few moments, the two climbed into the man's car.  Soon the two would be back at the man's house, where Sissy Suzette would pleasure his date with his soft manicured hands and his red glossy lips.  As Mildred watched them drive off, she had an orgasm imagining her nephew Stanley sucking on his date's cock and making him cum. 

Mildred rushed home to arrange many, many more dates for her sissy nephew.

Sissy Prepares to "Entertain"

Sissy Amanda's cell phone buzzed.  It was a text message from his wife.  "Leaving now.  Home in 1 hour.  Be ready to entertain."

"Home in just one hour!?!" Sissy Amanda thought with alarm.  He stopped scrubbing the kitchen floor and raced to his little bedroom in the basement.  He stripped off his maid's uniform, sat down at his vanity and got busy making himself look beautiful.  His wife and her lover would be home soon from their romantic weekend in the country and Sissy Amanda had been instructed to always look his best when they returned.  And from the text it was clear that he needed to be prepared to sexually "entertain" them as soon as they arrived.

Sissy Amanda finished doing his make-up and took a moment to look at his reflection in the mirror before putting on his dress.  He looked at his delicately arched eye-brows, at his sexy, smokey eye shadow, at the pink lipstick that coated his soft, full lips.  He burst into tears thinking about what he had become.......

My Sissy Assistant -- Part 2

Well, that first business trip with my little Sissy stepson as my assistant worked out so well, that he is now my full-time secretary!  He now comes wth me on every business trip I make.  He makes all my travel arrangements, takes notes in meetings, carries my suitcase, everything.  He even helps me get dressed in the morning.  I know he hates being paraded around in public all dolled up in chic little dresses and sky-high heels.  But he be behaves and follow my every order because that's how he's been trained -- and because he is simply terrified that someone will discover that he isn't really a cute little girl but actually a pathetic Sissy boy.

And because he is so pretty now, everywhere we go men take a lot of interest in him.  Waiters in restaurants, taxi drivers, strangers in airports, it doesn't matter.  If they have a dick, they start hitting on him.  It is hysterical!  The poor little Sissy is so embarrassed and mortified by the idea of men flirting with him.

But of course, this is more than just entertainment for me.

On my business trips, I often have dinner with businessmen trying to get me to place an order with their companies.  They wine and dine me.  Sometimes it's fun but mostly it is just business.  But now I make my Sissy stepson come out to dinner with me.  I've bought him a dozen sexy going-out-to-dinner dresses that I make him wear.  Well, the businessmen just LOVE it!  They can't stop drooling over my stepson, especially when I have him dressed so glamorously.  And after a few drinks, these men usual start flirting with my stepson.  They think I don't notice, but some men will reach under the table to place a hand on my Sissy's stockinged knee or to stroke his silky thigh.  

And that creates all sorts of opportunities.  More often than not, these businessmen will invite my Sissy stepson up to their hotel rooms for a "nightcap."  My little Sissy knows he has to eagerly accept these invitations -- even though he is disgusted by what awaits him.  But he is both obedient -- and well trained in various "womanly arts."

As soon as he arrives in their hotel rooms, the little Sissy starts making out with my businessmen like a horny little tramp.  Then he drops to his knees to  demonstrate what an expert little cocksucker he is.  He hungrily swallows every drop of cum that is shot into his mouth.  And then he licks the men's dicks until they are perfectly clean.  

And do you want to know what the best part of all this?  The businessmen like my little Sissy assistant so much, they usually give me an extra 5% discount on my order -- as long as I promise to let them see my Sissy assistant again! 

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.

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...