A Sissy Every Weekend. Part 1. Going to Aunt Jenny's House

This is a picture of me taken last Saturday when I visited my aunt and my cousins. And while you may think that I am a girl, I am not.  I am a boy.  But this is what I look like every weekend. Let me explain.

During the week, Monday through Friday, I'm pretty much like the other boys at school.  Of course my hair is a little longer and I'm very skinny.  Also I don't like playing sports and don't really have any friends.  But other than that, I'm just another boy at school.  

But all that changes as soon as I come home from school on Friday afternoon. "Hurry up, Sweetie!"  mother will call out as soon as I step through the door. "Time for you to change so we can get to Aunt Jenny's house."  She has already packed weekend bags for both of us and she impatiently waits for me to get dressed. It has been the same every Friday afternoon since I can remember.

I know mother was disappointed -- deeply depressed, actually -- when I was born. She is very close to her sister -- my aunt -- who has three daughters; the twins are four years older than me and Caroline who is about one year older than me.   After Caroline was born my mother had hoped desparately for a little girl of her own so that she could join her sister in endless mother-daughter activities.  But since I was born a boy, that dream was spoiled.  Or it would have been if not for my mother's determination.  Mother simply decided that I would have to be a girl when we got together with my aunt and cousins.  And we all get together -- all six of us -- every weekend. 


And if you wondering, there are no men around at all.  Aunt Jenny is divorced and mother was never married.  So I'm the only one in both our families who isn't a girl. At least not really a girl.

Sometimes I wish I didn't have to pretend to be girl every weekend. But I guess I don't really mind too much. It makes my mother very happy and I love my aunt and my cousins very much. But still sometimes I wish mother would let me be a normal boy...


So my weekends begin on Friday afternoons as I change out of my boy clothes and put on my girl clothes.  Even though my cousins and my aunt all know that I'm a boy, it was decided that I should already be dressed as a girl when I arrive at Aunt Jenny's house. That way it is less confusing for my cousins, I guess. 









I start by slipping on a pair of panties and a padded bra that makes me look like I have little boobs. Wearing just my undies, I brush my hair to look prettier and put on some mascara, a little blush and some lip gloss. 

Today, mother has laid out a white lacey top and a peach colored skirt.  The skirt is very short and I don't really like that, but mother says it makes me look very pretty. She also told me to take my blue and white purse and to wear my blue shoes with the 2 inch heel and the ankle strap. 

Mother fastened a little necklace around my neck. Then she snapped a few photos of me for her scrapbook like she does every Friday once I am dressed.  


Mother tells me that it is time to go so I get into the car and we start the 45 minute drive to where my Aunt Jenny and my cousins live.

A Sissy's Dinner Date Fantasy - Part 1

My name is Sean and I have been a sissy crossdresser all my life.  I have always kept it a secret, dressing up like a girl alone in my little apartment.  I only ventured outside "en femme" occassionally and only if I was pretty certain I wouldn't run into other people.

Night after night, I would come home to my apartment and transform myself into the lady of my dreams.  I had become very talented with my make-up, my mannerisms and my voice.  I knew that I looked very attractive and convincing when dressed.  Alone in my apartment at night, I would read romance novels and fashion magazines and watch chick-flicks on TV.  But the more time I spent pretending to be a girl, the stronger my fantasies became to actually experience life as a girl.  I became obsessed with the idea of being desired and romanced by a real man -- just like in my novels and in the movies.

About six weeks ago, when my obsession became too much for me to control, I went into action.  I created a profile of my femme self on Match.com.  It took me several hours to get it just right.  First, I picked out a few of my best girlie photos, including these two below.  I like the one on the left because it shows off my legs.  And I like the one of the right because it makes me look more sophisticated and mysterious.

And finally, just to make sure I got everyone's attention, a photo of me in a bikini!




















I came up with a back-story that sounded believable and would be appealing to men browsing through the website. I was, according to my profile, Sheila Landers, a 26 year-old junior high school teacher who had recently moved to the area.  I said I was looking for a "successful, older gentleman who was interested in a long-term relationship."  I described my interests in all sorts of girly things, like ballet and cooking.  I described in detail my idea of a perfect first date -- a candlelit dinner at a French restaurant followed perhaps by a romantic walk...I got myself excited just thinking about it!

What my profile didn't include was anything that was actually true. It didn't say that I was a 20 year-old sissy and college drop out who worked for minimum wage in a corporate mail room. It didn't say how the idea of being romanced by a man excited me and terrified me -- all at the same time!

When I was finally satisfied with my profile, I pressed Enter and posted it on Match. I didn't really know if anyone would write back to me or even notice my profile.

I needn't have worried about that. About two hours after I uploaded my profile, I had about twenty requests from men wanting to meet me. Within a week, I had over two hundred offers for dates!

A Sissy and his Mother have a Weekend Adventure -- part 3

Janey had a little headache when he woke up the next morning.  But we weren't going to let a little hangover spoil out last "mother-daughter" day in the city.  Janey wore a pretty black and white sleeveless dress, which was perfect because the day was warm.  Our plan was to have breakfast and then head to church -- going to church gives Janey the perfect excuse to get all dressed up on a Sunday morning. Then some more shopping, a light lunch and then back to the hotel for Janey to put his dresses away before heading home.

But just as we were leaving the hotel to walk over to the cathedral we ran into Janey's young banker friend from last night. 

"Janey!" he exclaimed when he spotted us.  He gave Janey a quick kiss on the cheek.  "I'm so glad I saw you.  I was going to call you later, but now I can ask in person."   The young banker looked my son up and down, his gaze lingering on Janey's sexy legs. "Wow! You look...amazing," he panted.

The young banker seemed to have lost his train of thought staring at Janey -- and Janey was so mesmerized by his romantic young banker that he had no idea what was going on.  I helped everyone out.  "Was there something you wanted to ask Janey?" I prodded.

"Oh, yes, right," he managed to stammer as he collected his thoughts.  "I have these tickets to a big charity fund-raiser on Friday night at the Downtown Yatch Club. It's one of the big social events of the year.  It is going to very nice party and I was wondering if, well, if you would be my date for the evening."  

Immediately, and without consulting me, Janey replied, "Oh yes!  I would love to go!"  And with that Janey gave his new boyfriend a big hug.

I, of course, was terrified.  Janey was quickly getting into very deep waters here and I was not at all certain that he would be able to pull this off.

Thinkly quickly, I explained to both of them that Janey and I would again get a hotel room for Friday night and that Janey could go to the party provided that "she" was back to the hotel by 1:00AM.  The banker gave Janey some more details and promised to be in touch soon.  We said our good-byes --  including a big, long kiss for Janey -- and Janey and I continued on with our ladies day out.

The days that followed that magical weekend were very difficult for Janey.  Not only did he have to change back into his boy clothes for the week, but poor Janey was experiencing his first schoolgirl crush. The emotions were so powerful.  He was simultaneously mopey and sad because he missed his young banker boyfriend and wildly excited about seeing him again at a fancy, very adult, cocktail party on Friday.

The school days passed very slowly for Janey that week.  When Friday did finally come, I let him miss school so that I could take him back in to the city to shop for a new dress to wear to the party.   We checked back into our hotel and hit the designer boutiques.  And we found the perfect dress!  It was a black, sleeveless dress with little white polka dots.  It was a faux wrap style that had a bow on one side and was cut tantalizingly low in front. The full skirt came right to his knee, a layer of chiffon gave the whole dress a romantic, elegant effect.  Janey looked stunning in his new cocktail dress.

We spent most of the afternoon getting him ready.  I took Janey to a salon near the hotel to get a mani-pedi (I knew he wanted to wear his favorite open toed shoes with the ankle strap) and to get his make-up done.  

Janey's banker met us in the hotel lobby. I thought the young man was going to die from excitement when he saw how pretty Janey looked. The banker had arranged a limo to take them to the party.  I said goodnight to the young couple and whispered to Janey to be careful.  As the limo pulled away from the curve, I gave a little wave as I watched Janey head off for his first date as a young lady.  

Of course I stayed up waiting for Janey to come back to the hotel that night. When he did get home, he was wide awake and bubbling over with excitement.  Janey had to tell me about every detail of his dreamy, romantic evening:  the music, the celebrities he saw, the food, the drinks, the pretty dresses the "other" ladies wore -- everything.  He even had to describe the fancy ladies rest room at the yatch club.  But mostly he wanted to describe how charming and romantic his date was.  How they danced together and how they made out on the balcony overlooking the harbor.  

Then Janey said, "He wants to take me out on another date -- alone -- tomorrow night."  

I knew that this charade must not continue. Someone was going to get very hurt when the truth came out -- probably Janey.  "No Janey, that is not a good idea.  I can't allow you to do that.  This is all getting very...complicated.  Just what do you think is going to happen when he finds out you aren't really a girl?"

"I already told him and he doesn't care!" Janey replied.  My mouth dropped open and I almost fell over with surprise.  "It's true," Janey continued.  "I told him that am a Sissy during the limo ride after the party.  At first he didn't believe me until pulled down my panties and showed him."

"WHAT?!?"  I exclaimed.  "What did he do then?"

"He said that if I wanted to be his Sissy that I needed to suck his cock.  So I did.  Right there in the limo.  And after he came in my mouth he told me that I suck cock better than any real girl that he's been with.  And that he wants me to be his Sissy! Isn't that wonderful, Mother?  I am so happy!  I am in love with him, Mother."   

Before I fainted, the last thought that passed through my mind was that my sweet little Sissy daughter was now a complete Sissy slut!

A Sissy and his Mother Have a Weekend Adventure -- Part 2

Janey finished doing his hair and his make-up.  He slipped on the dress I had bought him earlier that afternoon.  He looked simply stunning.  I was so proud of my beautiful sissy son.

We rode the elevator down to the restaurant.  As we crossed the busy hotel lobby, I was aware that everyone was noticing this striking, elegant and -- dare I say it -- sexy young lady as he walked past.  I'm sure Janey noticed that many heads were turning because of him.  

Unfortunately, the restaurant was very busy and we hadn't made a reservation.  The Maitre d'  suggested that we have a drink at the bar and "perhaps a table might become available."  We did as he suggested and stepped into the hotel's lounge. The bar was mostly full of men -- and it was very crowded.  When we couldn't easily find a seat, I started thinking about leaving.  But just then, two men slid off their bar stools and offered their seats to us.  


The men introduced themselves as investment bankers from out of town. They were stuck here over the weekend, they explained, because they were working on some big deal. The older one was a senior partner with their firm, the younger one was a junior associate.   They wasted no time in buying us drinks and chatting us up. The younger one seemed quite delighted with Janey and was working very hard at impressing him.  I could see that all of this attention was making Janey a bit uncomfortable but I was really enjoying the older banker's flirting.  He was quite charming and I was starting to have a lot of fun.  

After his second glass of white wine, Janey started to relax.  He seemed to get into the spirit of the moment and started to enjoy the young banker's overtures.  Janey laughed at the young banker's jokes and partipated more in the conversation.

More than an hour went by when I mentioned to the older banker that Janey and I had hoped to get a table at the restaurant but that we didn't have a reservation.  "Let me fix that," replied my handsome older banker.  He walked out of the bar and returned two minutes later.  "Our table is ready," he announced.

Apparently, my new banker friend was a VIP of sorts and when he wants a table, one is immediately made available.  Before I could react, Janey and I were being seated at a table with our two gentlemen admirers.  Janey was starting on his third glass of wine (and keep in mind, he is too young and shouldn't be drinking at all!) and he seemed to be OK with this unexpected turn of events.

Dinner with our two handsome bankers was lovely.  Both were charming and fun. Janey was a perfect lady and played his part perfectly.  Maybe too perfectly.  As dinner progressed, Janey and his young banker were whispering to each other and giggling.  After the salads were cleared, I noticed the banker had his hand on Janey's stockinged thigh -- and Janey didn't seem to mind.  And while we were waiting for dessert to be served, Janey and his admirer started making out -- right at the table!  I was quite shocked but I wasn't going to interfere.  And besides, it made it very natural for me to start a little canoodling of my own with my senior partner. 

As my banker was paying the bill, Janey and I stepped into the ladies room for a quick talk.  Janey was nearly bursting with excitement.  "Mommy, I think he really likes me!" he panted.  "He wants me to go back to his room with him.  What should I do?"  

"Absolutely not, Janey.  You've had too much to drink and you have no idea what you are getting yourself into," I replied.  I had never even dreamed that Janey would feel this way about a man, worked up in a girlish romantic frenzy like this. And what did he think was going to happen if he went up the banker's hotel room? "Why don't you and your new 'boyfriend' have another cup of coffee down in the lobby and I'll come back and get you in an hour.  That should give you some time to...get better acquainted."

So after Janey and his young admirer excused themselves to go to the lobby, my senior banker and I went up to his room for a quick roll in the sack.  I expect that he was married, but I didn't care.  I was super horny and he was great in bed.

After the hour was up I put my clothes back on and went down to the lobby.  There was Janey sitting on a sofa frantically making out with his new boyfriend.  I separated them and dragged Janey back upstairs to our hotel room.  

A Sissy and his Mother Have a Weekend Adventure -- Part 1

My son, Jamie, and I share a big secret.  Jamie is Sissy.  And while he tries his best to act like a boy at school, at home he is my Sissy daughter, Janey.  Over the years, Janey has really blossomed into a delightful young "lady" and I love the special times I get to spend with the daughter I never had.

Last weekend, we had the most wonderful adventure. After Jamie came home from school on Friday afternoon, we drove into the city, which is only a couple of hours away. We checked into our hotel and that's when the real fun began. Jamie stripped off his boy clothes, slipped on a fluffy bathrobe and started becoming my daughter Janey. Over the next hour and a half, Janey and I got ourselves all dolled up for a night in the city.

We finished doing our hair and makeup. I helped Janey zip up the new little black dress that I had bought for him. I let him borrow one of my necklaces and a fun oversized purse. Janey put on his favorite strappy platform sandals and he was ready.  Doesn't he look lovely!?!

We then went to the ballet which we both loved! Then we enjoyed a late dinner at a fancy French restaurant. It was marvelous.  The waiters fawned over my pretty daughter.  One even jokingly begged Janey for a date!  Janey was a good sport and giggled and blushed like a young lady would. 

Exhausted, we went back to the hotel where we slipped into our nighties and went to bed.

On Saturday morning, Janey decided that he wanted to wear his red dress.  It is very simple and yet so elegant.  And Janey knows he looks fabulous in it!  

We had breakfast at the hotel and then went to the art museum which had a wonderful exhibit on ballgowns from the 18th and 19th centuries.  Janey and I both enjoyed this very much.  We spent so much time at this one exhibit that we barely saw anything else in the museum. 

After we were done at the museum, we walked over to the Ritz Hotel where they serve the most delightful afternoon tea. Janey and enjoyed all the little sandwiches and sweets that were served.  Elegantly dressed ladies sat at all the other tables; some tables apeared to have mothers and daughters having tea together -- just like Janey and me!  I felt so fortunate to be able to share this experience with my special Janey.

After tea, we spent the rest of the afternoon shopping. At the lingerie shop I bought Janey some new bras and panties and stockings.  We then found some shoes for Janey at the big department store -- a pair of black patent leather slingbacks with a three inch heel and some cute sandals for the summer. Then we visited a couple of the designer boutiques and I had Janey try on literally dozens of dresses!  In the end we only bought one dress for Janey -- oh, but what a dress. 











We returned back to our hotel exhausted carrying all of our new purchases.  Since we were tired, we decided that we would have dinner downstairs at our hotel.  As we started to get ready for dinner, Janey asked me, "Mother, do you think I can wear my new dress tonight -- the one you bought me this afternoon?"

"Of course, sweety,"  I replied.  "I am sure that your new dress will be just perfect for tonight.  The hotel's restaurant is rather fancy and I am sure people will be dressed very nicely.  So yes, please wear your new dress."

We finished doing our make-up and fixing our hair.  Janey slipped on his new dress and modeled it for me.  "Oh, Janey," I sighed.  "You look...amazing."  A tear started to well up in my eye as I gazed at my beautiful, elegant son.

Two Million Page Views! Time to Celebrate with Your Sissy!

In celebration of our TWO MILLIONTH page view, I want all you Sissy Masters and Mistresses to buy your Sissy a pretty new outfit and show him off!   Use this wonderful milestone as an opportunity to display your Sissy in public in his finest, most feminine attire.  Help us educate the world on the wonders of our forced fem creations while publicly humiliating your precious little Sissy.

Sissy Pinkie's Master bought him a very special new outfit for the occassion.  Doesn't this darling little sissy look soooo sweet.  His soft white blouse with the contrasting collar.  The acres of chiffon in his little black skirt. And the cute beret and the pink purse are fantastic.  Come now, Sissy Pinkie, you should be smiling because you look so pretty in your new outfit!

But my favorite part is his shoes!  The open toes platform pumps and the lacey little anklets.  Simply perfect!  

Master is taking Sissy Pinkie out to dinner later with another Master and his Sissy.  Sort of a Sissy double date.  The restaurant will be very busy -- they will probably have to wait at the crowded bar before they are seated -- and the Sissies will have to endure lots of stares and comments from the other diners.  But first the two Masters and their Sissies are going to do some shopping at the mall.  The Masters want to show off their Sissies in their new outfits.  I'm sure the Masters will insist that their Sissies hold hands with each other as they traverse the mall.  The mall will be very crowded this afternoon and these Sissies will certainly get lots of attention.

To all you sweet Sissies and all you demanding Masters and Mistresses, thank you for reading these stories and for bringing us to two million page views.  

Remember:  Sissies are required to leave comments!  Do not disobey me!  Masters and Mistresses are kindly encouraged to share comments -- your thoughts and experiences are very important to all of us.  

Always seeking Sissy perfection,
Mistress Linda Trainer

A Sweet Sissy Escort

This is a picture of me taken yesterday.  I am an escort and I work the promenade near the fancy hotels downtown.  My real name is Robert.  But when I'm working, everyone knows me as Rebecca.

Ever since my dad ran out on us, things have been really tough for Mother and me.  Mother isn't very healthy and she can't work.  Then a few months ago the bill collectors started calling and the bank said that they were going to foreclose on the house. That's when Mother told me that she needed my help.

"Mother!" I cried, "I don't want to do that!  How can you even suggest that I do that?!?"

"But Robby," Mother replied, "It's the only way.  If you don't do this, we won't have any money at all and we'll be homeless.  And without money for my medicine...I won't live very long."


When she said that I gave in. She explained that she had seen an ad on Craig's List. There was a man named "Mr. Pearl" who was looking for "girls to entertain successful businessmen."

"But Mother," I shrieked. "I'm not a girl!"

"Well, of course not.  But you are rather...girly. I mean look at you.  Look how skinny and delicate you are. Anyway, when I described you to Mr. Pearl, he sounded very interested in  meeting you."

I was horrified and ashamed by everything she said. But I agreed to meet Mr. Pearl if it would help her.

Mr. Pearl was indeed very interested in me. He said that until I came along, he only had real girls working for him. He thought that he would find MANY clients who were interested in me since I offered something a "little different." 



Mr. Pearl and some of his girls helped get me started. They showed me how to use make-up and gave me clothes that would make me look sexy and get noticed. They taught me about all the different sex things that clients would want to do to me. I started crying at one point when someone explained about "double penetration." I didn't believe half the things they told me were true -- until I started working.

That was two months ago. Of course it was frightening and disgusting at first. But I have sort of gotten used to it and I'm earning a lot of money to help Mother.

Since then I have been working the promenade five nights a week.  I walk around, wiggling my ass and trying to attract the attention of the men who are out looking for some action.  Even though I am dressed like a sexy girl, because of my short hair most men figure out that I'm a sissy whore. While most guys are looking to be with a real girl, a lot of guys are really into doing it with sissies like me. 

On a good night I might have five or six "dates."  Most of my clients are businessmen in town for conventions.  Those aren't so bad because the businessmen are mostly pretty polite and we can go up to their hotel rooms to do it.  But some men are rough and mean.  And sometimes I have to do it with men in the backseats of their cars or in the public bathroom in the park.  The worst are the bachelor parties when I have to do a bunch of guys at the same time.  I get paid extra but I really don't like it.

Last night was horrible.  My last client -- number five for the night -- was insane.  He choked me and slapped me hard about a hundred times while I was blowing him -- I thought I was I going to die.  When I got home at 4:00 in the morning I was going to tell Mother that I couldn't do this any longer.  But before I could say anything, Mother told me that her new medicine was much more expensive.  She told me, as if it was good news, that Mr. Pearl had agreed to let me work seven nights a week and days too!  I cried myself to sleep knowing that I would be forever trapped as a sissy whore.  

The Sissy Debutante Ball

Mother had been dressing her son Jimmy up as "Ginger" for years.  At first Jimmy had resisted but his mother was very strong-willed and Jimmy was weak.  Over time, Jimmy stopped fighting his feminization and accepted what his mother was doing to him.

"I had always wanted to have a daughter," Mother told him a million times. "But unfortunately you were born a boy.  But just because you were born a boy doesn't mean I can't make you into my daughter." 

So ever since he was a little boy, Jimmy spent most afternoons -- and every weekend -- dressed as Ginger. And while wearing his pretty party dresses and nightgowns, Ginger and his Mother would spend countless hours doing things that mothers and daughters do.  Mother taught Ginger how to do his make-up and his hair and his nails.  They would do chores around the house like cooking and cleaning and ironing.  At night they often watch chick-flicks together while wearing their pretty night gowns.

So Ginger was brought up to be a perfect little Sissy.  But Ginger was growing up and tonight they would celebrate the lovely Sissy lady that Ginger had become.  Tonight was the Sissy Debutante Ball!

Tonight, nearly fifty Sissies, aged 18 to 20, and their Mothers would celebrate the long and sometimes difficult journey of raising a son to be a Sissy.  Mothers from all over the country brought their lovely Sissy darlings to this lavish affair at a posh hotel in New York City.  

Ginger and his Mother looked heavenly in their coordinated, custom-made outfits.  Mother wore a tailored suit of beautiful golden silk jacquard. Ginger wore a long gown -- made of the same gold silk jacquard as her mother.  Ginger's gown made him look sweet and sexy at the same time. Ginger and his mother had spent most of the aternoon at the beauty salon. Their hair and make-up were perfect.

Even though he looked very beautiful, Sissy Ginger was so nervous as he and his mother rode the evevator down from their hotel room to the ballroom below.  Sissy Ginger didn't know what to expect. 


They made their entrance when the Master of Ceremonies announced their names over the speaker: "Presenting Sissy Ginger and his Mother, Lady Annette!"  The other guests clapped as Ginger and his Mother entered the room.  Ginger was quite stunned by the applause and by the flashes of cameras capturing his big entrance. They found their seats, Lady Annette at one of the Mothers' tables and Ginger at one of the Sissies' tables.

As Ginger introduced himself to the other Sissies, he noticed there were several other tables in the ballroom that were occupied by men. Ginger asked one of the other Sissies who the men were.

"Don't you know?" answered one the other Sissies with surprise.  "After dinner is finished and the announcements are done, the Mothers will all leave and go to another room for the rest of the evening.  That's when the men are free to talk to us and dance with us and..."

"And WHAT?" Ginger asked, somewhat panicked.

"Well, they can ask us to come up to their rooms with them, of course.  And you are not allowed to refuse.  That is all part of the Sissy Debutante experience.  Tonight we become real Sissy Ladies with the Gentlemen that pick us.  Are you saying that your Mother never explained this to you?"
Poor Sissy Ginger.  He nearly fainted when he heard this.  Of course Mother had never told him about all this.  He would have been too terrified to even come here tonight.  

Tears started to well up in poor Ginger's eyes.  "Here, take this," said one Sissy offering Ginger a Xanax and a glass of champagne.  "Just relax and remember that this is what your Mother wants for you.  You need to be brave and do what your Mother expects you to do."

The other Sissy was right, thought Ginger as he downed the pill and the champagne in a single gulp.  "May I have some more champagne?" asked Ginger trying to prepare himself for the frightening evening ahead.  "A lot more."

Spring Break Sissy

When I told my parents that I was going to Florida for spring break, they were really worried.  They pictured me hanging out at wild, drunken parties and stuff like that.

But actually, my spring break is very different -- but my parents don't need to know that. 

You see, I am spending the entire week as Professor Wilson's sissy!


Here's a photo of me in the hot tub with my Professor and Master.

It all started last fall when I was taking Professor Wilson's Human Sexuality class.  I went to see him during his office hours one afternoon because I needed help understanding an assignment.  He closed the door to his office after I sat down.  Before I could even ask a single question, Professor Wilson asked me, "You're a sissy, aren't you?"

I was shocked and scared by his question.  The truth is that I am a closeted cross-dresser, often having fantasies of submitting myself to be feminized and controled by a dominant man or woman.  But this was my secret.  I had never told anyone this.  How could Professor Wilson possibly know?

"I asked you a question, sissy!" he shouted.  "Don't deny it.  I know what you are.  I can tell.  It's my expertise, after all.  Now I am going to ask you again.  Are you a sissy?"

I lowered my eyes to the floor, and softly answered, "Yes," unable to resist the Professor's command.

"I knew it!" he exclaimed with a self-satisfied smile.  "Well from now on you are going to be MY sissy.  That means you will do whatever I tell you to do.  You will submit to me in all ways.  Do you understand?"

"Yes, Sir," I meekly responded.  Professor Wilson smiled again.

I now visit Professor Wilson at his home every evening and every weekend.   When we are together, he is not nice to me at all.  As I walk in the door, he instructs me on how I should dress for the evening.   I prepare myself as quickly as possible -- make-up, lingerie, a dress, stockings, heels -- the works.  He then proceeds to order me around for the next few hours.  This usually includes cleaning his house, doing his laundry and making his dinner.   If I do anything that displeases him, he throws me over his knee for a harsh spanking.  

When my chores are done and he has finished eating, he has sex with me.  He often orders me to bend over the back of the couch so he can take me from behind.  If there is a big game on TV, he makes me suck on his cock while he watches the game.  Then after he cums and I have cleaned up the mess, he orders me to get out.

My Professor/Master has helped me to understand that, as his sissy, I exist for only one reason -- to serve and please my Master -- and that my feelings have no importance.  I am just an object for him to use for his pleasure.   

Now it is Spring Break and Professor Wilson has arranged for a perfect Master/Sissy vacation.  All year I have growing my hair out and Master has kept me on a strict diet so that I would look extra girlie for our trip.  He rented a beautiful condo that has a view of the Intercoastal Waterway, a big deck and a hot tub.  He packed several pretty outfits for me to wear, lots of sexy lingerie and even two bikinis!

Master has been so nice to me since we arrived at the condo!  Of course I have to do all the chores and follow all of his orders and he has spanked me a few times.  But mostly we are passing our days and night in bed or in the hot tub.  It has been so romantic!  We have been spending hours and hours kissing and having sex.  And after he is done having sex with me, he has been letting me snuggle up against him.  I feel so safe and happy when Master wraps his big strong arms around me. 

Here we are in the tub again.  I am giving him a handjob.  His enormous, hard cock feels so good in my soft, manicured hand.  I am so content and fulfilled serving and pleasing my Master.  

I wish my Sissy Spring Break would never end.

Sissy Gets Ready to go Out

Two months ago, my little sister had caught me dressed up in mom's clothes and make-up when she came home early one afternoon.  She said that she would tell mom and dad -- unless I did exactly what she said from now on.  I guess I had always been a bully to my little sister and now was payback time.

Since then, we've been playing "dress up" almost every night.  After dinner, we run up to her room where she makes me practice doing my make-up and styling the wig she made me buy.  She makes practice walking in high heels and sounding like a girl when I talk.

She told all her friends about what a sissy I was -- and how I was really cute when dressed up like a girl.  Tonight, my sister told me, was going to be my "coming out" party.  She was going to take me, along with three of her friends, to a fancy club downtown where they never check IDs of cute girls who want to go in.  I'm the only one old enough to have a license, so I have to drive.

Mom and dad went out early to go to a party so we spent most of the afternoon getting ready.  My sister picked out my outfit for the evening from mom's closet -- a fancy gold and white Lily Pulitzer dress and a pair of strappy high heels.  She helped me get my wig and make-up just right.

"Hmmm," she said with a smile while looking me over when we were done.  "You know, Michael, you really do look like a pretty girl.  I don't think any of the guys at the club would ever guess that you're really a boy when they start flirting with you.  Just be careful when they start feeling you up."

When she said that, I broke down into tears, panic suddenly overcoming me.  "Please don't make me do this!  PLEASE!"

"Oh for God sake STOP CRYING!," my sister yelled.  "You're ruining your make-up!  You are such a big sissy!  Get it together and fix your make-up before the girls get here!  NOW HURRY!"  She slammed the door and went downstairs.

I stared at my reflection in the mirror.  My sister was right -- I did look like a pretty girl.  And she was also right about me being a big sissy. I knew I had to obey my sister or she would tell mom and dad.  As I started redoing my make-up, I tried to imagine what it was going to be like, being in a fancy nightclub in a pretty backless dress, sexy stilettos and glamorous make-up, knowing that men would be trying to talk to me and buy me drinks and...other things.

"Michael!  I mean Michelle!" my sister yelled from downstairs.  "Hurry up!  The girls are here!"

I dried my tears and fought to calm myself down.  I fixed my mascara and finished putting on my bright red lipstick.  I grabbed my little clutch purse and headed down the stairs.

When my sister's friends saw me, they screamed with delight.  They all told me how pretty and sexy I looked.  They said that all the guys would be drooling all over me tonight.  I enjoyed hearing the girls say that I was pretty -- but talking about the men at the club made me feel  sort of sick to my stomach.

One of the girls said, "And when you're giving some guy a blow job tonight, be sure to swallow every drop.  You don't want to get any stains on  your mother's pretty dress."

The girls howled with laughter at that.  I almost started to cry again.

"Time to go, Michelle," my sister said.

Blonde Sissy for Black Master

When the world middleweight boxing champ wanted to get his very own sissy, he came to me. He was a black man, amazingly strong and fabulously wealthy.

I transformed a young man into a perfect sissy sex toy for him.  Sissy Tammy's body had been forcibly feminized to perfection.  Sissy Tammy was petite, blonde and completely terrified of his new owner, who has made Sissy Tammy's life a nonstop nightmare.

Master enjoys using Sissy Tammy as his own living sex doll, forcing himself on his defenseless little sissy whenever and where ever he wants.  Master likes to pick his sissy up in his big strong arms and fuck him in mid air, roughly bouncing his sissy up and down, again and again, on his rock hard cock.  Poor little Sissy Tammy feels like he is going to be split in two every time Master rams his huge cock into his tight little Sissy pussy.  Sissy screams in pain with each thrust, but the sissy's sceams just get Master more excited.

After Master is done filling Sissy Tammy's ass with gallons of his hot cum, Sissy Tammy crawls between his Master's legs and carefully licks his Master's massive dick clean.  If Master gets hard again, then Sissy Tammy gets to swallow another load of his black Master's seed.  And when Master tires of having his enormous dick sucked, he lies down on his king sized bed for his nightly massage.  Sissy Tammy has been trained to expertly massage his Master's strong, muscular body.

Oh dear, it looks like the massage is making Master's dick hard again.  Get ready for another fucking, Sissy!

Poker Night Sissy

Every Friday night, Master invites five or six of his friends over for poker night.

Master insists that I get all dolled up in a fancy cocktail dress, 5-inch heels and sexy make-up.   My strapless dress barely covers the large breasts Master forced me to get.  He says I have to look my best when his friends are over.

At 8:00 the guests begin to arrive.  I greet them at the door and take their coats.  Always keeping my eyes lowered, I inform them that I am the "sissy of the house" and that I have been instructed to serve my Master's guests in whatever way they require.  As I say this, I can feel their hungry eyes on my exposed cleavage.  I can tell they are smirking at my humiliation and submissiveness.

For the next four hours, I serve them drinks and snacks.  The men play cards and drink and smoke and laugh.  Mostly they ignore me, but they often grab my ass or squeeze my boobs when I am serving them. They say mean things to me and call me "whore" and "slut" while they fondle me.  When I'm not serving the men, I stand silently in the corner and wait.

Then, promptly at midnight, the men put down their cards.  The game is over and they count their chips.  They carefully figure out who won, who came in second, third, and so on.  Then they line up, the winner in front.  It is now time for me to do what I have been dreading all evening.  I drop to my knees in front of the winner, I pull down his pants and I open my mouth.

The night's winner jams his big dick into my mouth and I suck and lick it eagerly the way Master trained me. The winner's dick get bigger and harder.  He roughly bucks his hips, ramming his cock in and out of my mouth for several minutes.  Then he grabs the back of my head and forces his cock down my throat.  And then he explodes.  He blasts his hot, sticky cum into and I swallow it all.  All the other men hoot and shout as they watch the winner cum in my mouth.

"Next!" Master yells to everyone's amusement and the next man in line drops his pants.  I put his cock in my mouth and let him rape my face.  I repeat this until each man has unloaded his sperm into my mouth.  And for being the night's winner, I have to give the first man a second blow job.

I feel sick and disgusted, with the load of several men in my stomach and on my face.  "Get yourself cleaned up!"  Master yells at me.  "What a whore!" he adds to the amusement of the others.

I race to the bathroom and quickly wipe off my face and redo my lipstick.  I rush to get the men's coats and to see them out.  They usually have something mean to say or enjoy one final laugh at my expense as they leave.  With the final guest gone, I get busy cleaning up after the night's game.

With the house clean and the clock striking 3:00, I enter Master's bedroom where he has been sleeping.  I pull back the covers and begin performing my last blow job of the night on my Master's massive cock.  "You are such a filthy little sissy slut," Master mutters, half asleep, as I begin to cry.

New Sissies at the Beach

Last week I took my two newest Sissies for a day of fun at the beach.  It was a holiday weekend, so the beach was very crowded and my Sissies attracted a lot of attention!

These two fell into my clutches just a few weeks ago.  They are just at the very beginning of their transformations.  Their boyish haircuts are just starting to grow into more sissyish styles -- although I already dyed their hair to a prettier, more feminine color.  They are still very confused and frightened by their captivity and forced transformations.

My newest Sissies were horrified when they saw the outfits they would be wearing.  But their protests subsided after a few whacks with my hairbrush.

And aren't they absolutely darling!?!  I just loved dressing these two up in these identical sissy bathing suits -- with the matching sissy cover-up.  The high waisted panty (with an adorable little bow!) and the training bra tops are simply devine.  And the little pink heartsare just perfect for little Sissies.

I love this photo.  The Sissy in front is about to start crying as I just ordered him to take off his cover-up and let everyone see him in his pretty Sissy bikini!

Sissy Pets -- Part 3

Sissy Timothy was forced to try on all three of the dresses selected by the saleslady and to model each of them for his Master.  Master expressed his opinions in an overly loud voice, ensuring that other shoppers would hear and take notice.

Master was very pleased with the first dress, the flowered one with the open back.  "Oh yes," he practically shouted, "He looks so cute and sissyish in that dress.  I definitely want him to have that dress."

Sissy Timothy and the saleslady retreated to the changing room where Sissy Timothy tried on the second dress.  It was very, very short, in a pale gold satin, with ruffles at the shoulders and a huge bow at the neckline.

"I like this one too," Master bellowed.  "That dress is just perfect for a sissy.  Look how feminine it makes him look."  Sissy Timothy wanted to sink into the floor as other shoppers began to take more notice and crowd around.















It was time for Sissy Timothy to try on the third and final dress.  The dress was white with generous black-trimmed ruffles running across the neck and shoulders.  It was very short and fitted in a way that made his waist look tiny.  While Sissy Timothy changed into the third dress, the saleslady slipped out of of the fitting room, returning a moment later with a pair of platform sandals.  "These will look nice with that dress," she said as she helped Timothy finish changing.  

Once again, the saleslady grabbed the Sissy by the arm and dragged him out to show his Master.  "That one is my favorite!" Master exclaimed as Timothy emerged from the dressing room.  "Why so sad, Timothy?" Master asked loudly.  "Aren't you happy that I'm helping you be such a pretty Sissy?"  Timothy was near tears as the onlookers started laughing at the spectacle.  "We'll take all three dresses for my Sissy -- and the pretty sandals, too!" Master announced.  "Don't bother changing him," Master said to the saleslady.  "He can wear that one home."

Sissy Pets -- part 2

Sissy Timothy hated going to his ballet lesson.  He was in a class of 9 and 10 year old girls.  He was forced to wear a peach colored leotard and a ruffled tutu.  Master always watched his ballet lesson, enjoying Timothy's humiliation as well as ensuring that Timothy was trying his hardest to learn to dance.

After class ended, Master took Sissy Timothy to the mall to go dress shopping.  Poor Sissy Timothy was still wearing his leotard as they walked into the dress departmant at Macy's.  Master found a sales lady and explained to her, "My Sissy and I are going to take a cruise together and I would like to get him some cute dresses to wear to dinner.  You know, something sweet for a Sissy."

"I think I understand what you might be looking for," the helpful saleslady said.    She disappeared for a few minutes and returned with an arm load of dresses.  "Let's see if any of these will work."  She proceeded to hold the dresses up in front of poor embarrassed Sissy Timothy, while his Master commented on which ones he liked best.  Having Master's approval on three of the dresses, the saleslady grabbed Sissy Timothy by the wrist and dragged him back to the ladies fitting room.  And to Sissy Timothy's surprise, she joined him in the room and closed the door behind them.

"Now, let's get you out of that leotard," the saleslady said.  Sissy Timothy hesitated.  "Come, come now," the saleslady chided, "Nothing to be ashamed of.  No 'men' in here," she said with a grin and a wink.

Sssy Timothy's face turned bright red as he squiggled out of his leotard.  The saleslady couldn't suppress her laughter when she saw Sissy Timothy standing there in his training bra and Hello Kitty panties. 

Sissy Timothy tried on the first of the dresses, a short, floral dress with a mostly open back.  He almost started crying when he saw his reflection in the mirror and how completely sissified he had become.

"Oh, that's adorable!" the saleslady said.  Let's go show your...gentleman friend."  Again, the saleslady grabbed Sissy Timothy by the arm and dragged him out of the fitting room.

Sissy Pets -- Part 1

During the past two years, there has been a hot new trend for Sissy owners and collectors. Instead of ordering big breasted, totally transformed artificial girls, some Masters are now ordering partially transformed Sissies. Allowing no surgery and often no hormones, these Masters like to own a forcibly sissified boy who they keep in a permanent state of sexual limbo and torment.   Although these Sissies sometimes have long hair and wear make up, these femme boys are not allowed to pose as girls. They are  Sissies. They are often dressed in cute little Sissy outfits and don't even get to have a girly name.  I call these things "Sissy Pets."


"Sissy Timothy!"  Master bellowed in the crowded restaurant, attracting as much attention as possible. Sissy Timothy scurried back to the table having checked his Master's coat.   Poor Timothy's face was bright red, feeling every eye in the restaurant staring at him as he raced back to his Master's table. The other restaurant guests laughed seeing Timothy in his humiliating sissified state.  His outfit was Sissy perfection -- a silky blouse with an oversized collar,  shorty-shorts, sheer anklet socks and platform sandals.  He was near tears having his sissification being displayed so publicly.

Master ordered their dinners in a loud voice.  "I'll start with a vodka Martini and then I'll have the steak. My Sissy will have a glass of skim milk and the mixed greens, no dressing. I need my Sissy to keep his girlish figure!" he added to the delight of everyone in the restaurant.

While they waited for their food, Mster took out his cell phone and snapped his fingers twice. Sissy Timothy leapt to his feet and immediately began to massage his Master's broad shoulders, while Master conducted some business on the phone.

When their food arrived, Master put away his phone and told Sissy Timothy to sit.  "Sissy, I have some fun plans for us for tomorrow."  Sissy Timothy looked up from his salad with dread.  "After your ballet lesson, I thought we would go to the mall and buy you some pretty new dresses.  Wouldn't you like that?"

"Yes, Master, I would like that very much.  Thank you," Sissy Timothy obediently replied, horrified by the idea of it.  The other restaurant guests listened to the conversation with amusement, fascination and confusion.