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.  

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.  

Sissy Goes Outside Part 5

For the last few weeks, I've been with Dick every possible minute.  We spend hours in his apartment where he lets me suck on his cock and please him in other ways.  I love making him cum!  It makes me feel alive and valuable to know that I'm giving my Man the pleasure he deserves.

And now we go out together at night too, several times a week.  We go to the movies and bars and restaurants.  It is so exciting to be the feminized Sissy possession of a big strong man.  I love spending my afternoons making myself pretty for Master Dick.  And I love spending my nights being kissed and fucked by him.

I am working so hard to make myself more feminine and sexy for Dick.  I've been dieting and lost seven pounds.  And I've started taking my sister's birth control pills.  The pills have already started making my skin softer and prettier and my nipples have become very swollen and sensitive.

Dick is nice to me almost all the time.  But sometimes I disappoint him and he has to punish me.  I understand.  It is important that I learn to be a perfect Sissy and to always please my Master.  Sometimes Master Dick has to spank me if I have failed him in some way.  He seems to like spanking me, especially if we are out in public.  I am very grateful to my Master for helping me to become a better Sissy.

Master Dick had told me that he had "special plans" for tonight. So I stole this elegant outfit and strappy I I wanted to look my best for my big night with Master Dick, so I borrowed and pretty lacy outfit and sexy strappy shoes from my mother's closet. Then I spent most of the afternoon at the beauty salon and had the girls give me "the works". They even gave my hair some pretty highlights.   I feel so beautiful and feminine!  Dick almost fainted when he saw me!

Dick had made reservation at the fancy French restaurant overlooking the river.  It was all so romantic!  And then, as we were waiting for dessert, Dick got down on one knee.  The whole restaurant went silent and everyone was watching us.  Then, Dick pulled a ring from his pocket and said loudly enough for all to hear, "Will you marry me?  Would you be my Sissy Wife?"

"Oh yes!  Yes!" I exclaimed.  "Of course I'll be your Sissy Wife!"

The people in the restaurant clapped, although they seemed a bit confused by what they just saw and heard.

So now I am going to be married to my Master Dick, who I adore and worship.  I will be able to dedicate the rest of my life to pleasing and serving my Master/Husband.  I am so happy!

And it is all because my sister and her friends caught me dressing in her clothes just a few months ago.  What a lucky Sissy I am!

A Sissy Goes Clubbing

I love taking my Sissy "boyfriend" out clubbing on Saturday nights. 

We had been dating for several months when he admitted to me how he liked dressing up like a girl.  I was disgusted by the idea but agreed to let him dress up for me one evening.  Well, when he emerged from the bedroom dressed up as "Lydia", I was just amazed by how feminine and glamorous he was.  He wore a long black wig that looked so nice with his dark complexion.  His make-up was dramatic, theatrical even.  Long false eyelashes, shimmery eye-shadow, glossy bright pink lips.  Wow!

He was just delighted with the compliments I showered on him.  I told him about a hundred times how "beautiful" and "sexy" he was.  He shuddered with pleasure everytime I said that.  It was clear to me that I could have complete control over this Sissy faggot -- all I had to do was to pretend to be supportive of his girliness.

"Do you like me dressed like this?" he tentatively asked, his voice a sweet feminine whisper.

"Oh, I think we're going to have a lot of fun together, Lydia," I replied.  Just not the kind of fun you think, Sissy, I thought to myself.  I took a bunch of photos, while he enjoyed posing like a fashion model.

"Lydia, you look so wonderful, I think we should go out," I said. Sissy Lydia was shocked and scared by my suggestion.  You see, he had never been outside his apartment dressed as a girl.  I borrowed his make-up kit and made myself up glamourously, just like him.  Lydia showed me his extensive wardrobe of sexy outfits.  I dressed him in a clingy black mini dress, topped with a bright pink jacket, and some strappy sexy high heeled sandals -- what a Sissy!

I pushed him out the door and we took a cab to a crowded dance club downtown.  I made him dance with a bunch of guys -- while I did the same.  He kept begging me to leave -- the little Sissy was so scared and helpless!  After a couple of hours we did leave -- with two of the hot guys we had been been dancing with.  I told my little Sissy that he better behave himself, because I had his wallet, his clothes -- and photos of him that I could easily email to his family -- or his boss.  Defeated, the little Sissy got in the cab with me and our hot dates to go back to my apartment.  It was fun watching my little Sissy squirm while his "date" started putting the moves on him.  Hysterical!  And then they started making out -- I almost came watching that action.  As we arrived at my apartment I warned Sissy Lydia that he better act really girlish because if the guys figured out he was a boy, they'd kill him!  The Sissy was so scared that his secret would be discovered that he did everything I told him to do.

Well that night, Sissy Lydia gave his first blow job!  And since that night he's given dozens more to the guys we meet at the clubs every Saturday night!  She is my little pet Sissy toy that I now drag with me every time I go out!

A Sissy Girlie-Boy -- Part 6

It's been six months since Mommy made me start working at Frank's Hideaway. 

I don't cry in the car on the way to the bar anymore.  I don't care.  I don't care about anything anymore.

I take a lot a Ecstasy and I let the men at that bar buy me Cosmos and shots.  I'm too young to drink, but nobody cares.  Tonight I'm wearing a sparkly red dress.  It's very short and very clingy.  The men really like me when I dress like this.  Mommy has bought me a lot of sexy new dresses recently.   Mommy is really happy.  She has a new BMW and lots of new jewelry and even a mink coat.  But she wasn't so happy when I first started at Frank's Hideaway.  I still remember my first night at the bar.

After being fucked by Manny at my "audition", Mommy was really mad at me for screaming so much while Manny raped me.  She told me that I better learn to "shut the fuck up!"  After Manny was done with me, she told me to get myself cleaned up and that she would be back before the bar opened.  I did as she told me.  I went to the ladies room and brushed my teeth and tried to clean myself up as best I could.  I fixed my make-up and returned to the bar.  A few minutes later, Mommy returned to the bar and handed a package to Frank who was already behind the bar getting ready for the first customers to arrive.

Mommy handed me a couple of Valiums and told me to take them.  She said to me, in a very threatening way, that I better not mess up tonight.  She said that we were very lucky that Frank was letting me work there.

At a few minutes before 9:00, Mommy positioned me on a stool and again told me to do everything Frank told me and to, "...for God's sake, stop your God damn screaming!"  Mommy said she would return at the end of the night and with that Mommy was gone.

The bar was very quiet.  There were two other bar girls -- real girls -- positioned on other stools at the bar.  They were talking to each other and laughing and pointing at me.  I would learn that the other bar girls would never be nice to me.

The bar opened at 9:00 and the men started pouring in.  After a few minutes,  men started to gather around me.  It wasn't long before I started to feel some hands grabbing my ass while some other hands started to brush against my shoulders, my legs....

At 10:00, I was told to escort my first "date" of the night into the back.  I was terrified but I knew I had better do my best to cooperate.  My "date" was an older man, mostly bald, sort of fat.  He smelled like cigarettes.  He threw an arm around my shoulders while we walked to the back.

Once in my cubicle, he pulled down his pants and he said, "Come on baby, let's go!"  I hesitated, not sure what he wanted me to do.  "Come on!" he shouted.  "I only get 25 minutes!  Get going!"

His face was getting red and I could tell he was sort of drunk and getting pretty angry.  I figured he wanted a blow job, so I quickly got on my knees.   He fished his cock out of his underpants and jammed it into my face.  I closed my eyes and opened my mouth...

And that scene repeated itself all night long.  Man after man, cock after cock...I worked hard to make each man cum as fast as I could.  I knew I would be in trouble if I failed to make any customers cum in the 25 minutes they paid for.  I would rush to the ladies room in between each date and try my best to clean up in the five minutes allowed.

And then my 12:30 "date" wanted something different.  He wanted to fuck my ass.

"Get over here, bitch," he said.  "Frank said you have a problem with making too much noise, so he gave me this."  He was holding the package that Mommy had handed Frank just before the bar opened.  My "date" reached into the package and pulled out a ball gag.  "Get over here and open your mouth."

I did as he ordered and he fastened the ball gag tightly around my head.  "There," he said, "now you're ready."  He grabbed my panties and yanked them down and pushed me over the arm of the couch.  With my bottom stuck up in the air, my "date" rammed his hard dick in to me hard.  I tried to scream in pain, but with the gag in my mouth all that came out was a muffled moan.  "Oh yeah," he said, "you like that, don't you baby!"  He continued to bang away at me until he came, all the while I screamed in near silence through my gag.

And the night -- and every Friday and Saturday night since -- continued like that until 3:30 in the morning. 

Mother's Sissy Creation

Ever since Mother caught me dressing in her undies, she has been forcing me to dress up and act girlish every day after school -- and all through the weekends.  I am no longer permitted to spend time with my friends -- all of my time is spent with Mother.  She has been training me to act and move and talk like a girl.  She is making me grow my hair and my finger nails very long and she had my ears pierced.  She even plucked my eye brows to look pretty.  Even though I dress like a boy at school, I am mercilessly teased and bullied by the other kids who can see how girlish I am becoming.  The other boys call names like "Sissy" and "Faggot."

Yesterday, Mother announced that I was ready to "go public."  I didn't know what that meant -- but I soon found out.  After school, Mother worked on my hair and make-up for a couple of hours until she was satisfied that it was perfect.  Then she zipped me into bright blue halter dress that she had bought for me.  The dress was very silky and slinky and sexy.  She doused me with perfume and put some of her fancy jewelry on me.  Once I was all dolled up, Mother handed me a little clutch purse and ordered me into the car.  We drove downtown to a fancy French restaurant where we ate dinner.  I was so nervous.  I could tell people were staring at me -- especially the men in the restaurant.  Mother ordered a Cosmopolitan for me to drink to help me calm down.  Throughout the evening, Mother whispered instructions whenever I did something that was less than lady-like perfection.  I survived the experience and we drove home.

Today, when I got home from school, Mother told me that we were going back to the same restaurant.  The whole process of getting me ready started over again. Hours were spent on my hair and make-up.  Then she squeezed me into strapless black cocktail dress.  It was so tight I could barely breathe.  Worst of all, I felt practically naked.  Dressed like this I was certain to attract even more unwanted stares from the men at the restaurant. 

As we pulled up to the restaurant, Mother said, "Oh, and one more thing.  Tonight you'll be having dinner with a man named Mike Carson.  He's a 45 year-old businessman who is really into 18 year-old girls -- like you, or so he thinks!  That's right, Sissy -- tonight you're going on your first date with a MAN!  I'll be at the next table watching everything, so you had better behave perfectly.  And don't forget, Sissy, after paying for an expensive dinner, a man expects a little action from his date -- and you had better not disappoint!' 

Sissy's Night Out

I am a life-long crossdresser.  I had thought that I was so lucky to have a supportive and understanding wife.  Every Saturday night, my wife and I go out to restaurants and dance clubs as two girls.  After years of practice and lots of help from my wife, I have become completely passable as a woman.  It is so exciting being out in public as "girlfirends" with my wife. 

But tonight, as I was finishing my make-up for our "ladies" night on the town, my wife announced a change of plans.  Tonight we weren't just going out as two girlfriends, as usual.  Tonight, we were going out on a DOUBLE DATE! 

At first I just laughed, but then, to my horror, I realized that she was completely serious.  She had everything all arranged.  Her date was a handsome and successful plastic surgeon that she knew -- it was the same doctor that did her boob job last year!  For me, my wife informed me, she had found (on the internet, of course) a "big and muscular" truck driver that was totally into Sissies like me.  We were first going to have dinner at the French restaurant by the river, and then dancing at the club at the Hyatt. 

Then my wife dangled two Hyatt hotel keys in front of me.  Oh my God!  She had reserved two hotel rooms.  "That's right, Sissy," my wife sneered.  "Tonight we are both going to spend the night with our 'boyfriends.'  Since it's a first date for you, that makes you a slut!" she said with a big laugh.  "Of course, I've been sleeping with my boyfriend for months -- but I guess you didn't know that."

I was in shock and I was terrified.  Tears started to well up in my eyes -- both from the news that my wife had been sleeping with another man and from the fact that I was being forced into a weird sexual encounter with another man.

"Oh don't look so sad!  We'll have a great time.  You'll just LOVE being out with a big strong man.  Now put a smile back on your face and finish doing your make-up right this minute!" she commanded.  "Mmmm, yes that's nice.  Use lots of lip gloss.  That pretty mouth of yours is going to get a lot of use tonight!"

"Now hurry up and grab your purse.  Our boyfriends are waiting for us downstairs.  Let's go, Sissy!"

Dressing for Sissy Success

 It's a very exciting moment when your Sissy is ready to be sent off for his first day of work.  I have made arrangements with a few local businesses to hire my Sissies as receptionists and secretaries. 

I have a wonderful arrangement with these local businesses.  For $3.00 per hour (paid directly to me of course) they get the services of a meek and eager-to-please Sissy.  I ensure that all my Sissies are well trained and so it is a real bargain for the employer.  And of course, if the boss wants some "extra service" from his newest employee, well that's fine with me.  I don't care if my Sissies spend half their day on their knees under the boss's desk with a big cock in their mouth.  As far as I'm concerned,  the boss is always right!

The only condition I place on the employers is that I insist that everyone in the workplace know exactly who and what my Sissies.  Sure, many of my Sissies could pass as just another genuinely female bimbo -- but that's not what I want.  I want everyone to know -- from the other girls in the office, to the big hunks on the loading docks, to the salesman that visit the office -- that the sweet little thing serving them is a Sissy.

When it's time to send your Sissy off to work, I think choosing the right wardrobe is terribly important.  Your Sissy's outfit needs to scream femininity.  It needs to be sexy and impractical.  It needs to show off your Sissy's new curves and as much cleavage as possible.  It also needs to be something no genuine woman would wear to the office.  In fact, I try to dress my Sissies in a way that infuriates and insults the other women in the office, making the Sissies' life just as uncomfortable as possible.

Dressed this way, there is no way that your Sissy's life won't start to get complicated.  Some man is going to start hitting on your Sissy -- maybe a Salesman visiting the office, maybe one of the janitors -- who cares.  And my Sissies are trained to never --  never ever -- say no to the advances of a man.

So here are a few of the outfits I have picked out for my working Sissies recently.  It can be so much fun to dress up your little working Sissy like this and then enjoy the show!

Sissy's First Date

The girls at the salon had great fun with me today, spending hours on my hair and make-up.  They even gave me a bikini wax.  All afternoon they chattered excitedly about my big date tonight -- my first date with a man!  I am absolutely terrified and disgusted by the whole idea.


After discovering my crossdressing secret two years ago, my wife has been forcing me to become more feminine and subservient.  She has used diet, hormones and coercion to transform me from a closeted crossdresser to a pathetic, full-time sissy under the complete control of my wife. 


My wife no longer accepts me as her husband and has recently started entertaining her new lovers in our home,  And now she has told me that I also need to have male lovers! 


That is why I have been all dolled up for my big date tonight.  My wife arranged everything.  She picked the man ("Very tall, very muscular -- a real alpha male!" she said), picked the rerstaurant and ever reserved a hotel room for afterwards.  I have been instructed to please him in every way and that I may not come home until morning.  Also -- I will be in big trouble if he doesn't ask for a second date.


My wife insisted on snapping photos while I got dressed.  She had me perch on the chair and pose for some sexy photos in just my underwear.  I forced myself to smile so as not to anger her.  She made it very clear to me that she expected me to be enthusiastic and charming at all times -- regardless of how I actually felt. 

"Enough prancing around in your sexy undies," my wife siad.  "Let's get you into that pretty dress I bought for you.  You are going to look so pretty tonight!  Your handsome date will be simply delighted!"

Just as my wife finished zipping up my form fitting dress, the doorbell rang.  "Oh, he's here!" my wife exclaimed.  I felt faint and wanted to run and hide -- but I had no where to go.  My wife handed me a cute clutch purse and pushed me towards the door.  "Now, be a good little sissy and do everything I taught you.  And maybe next week we can go on a double date with both of our boyfriends.  See you in the morning!"