Sissy Roommate -- Part 2 -- The First Time

As I said, I am Tank's full-time sissy girlfriend now.  I wear only girl clothes and make-up and I keep my hair long and in a very feminine style. I diet to stay super skinny.  I slather my body with creams and lotions to keep my skin soft.  I do this all to please Tank.  I haven't seen Tank all summer and he should be arriving any minute. Here are some photos Tank took of me last spring. He likes it when I wear really short skirts.

But I wasn't always a girlish sissy living only to serve a demanding, strong alpha-male. My life changed completely that first day that I met him.

"Come over here," Tank said, without even bothering to ask my name.  "I have a cramp in my leg.  I need you to massage it for me."  Tank pulled off the sweat pants he had been wearing, revealing a thin pair of nylon gym shorts.

I did not want to do what Tank was asking.  "I don't know anything about massages or..." I started to explain.

"Just do it now!" he demanded, pointing to his thigh.


I don't know why, but I complied with his order.  I figured he was an important athlete and that I should try to help him out if I could.  I knelt by his bed and started rubbing his thigh.

"Mmm.  Yeah.  That's good.  Rub harder.  Yeah," he said.  I was pleased that I was doing it right.  "You're hands are so soft.  Like a girl's."  I felt embarrassed when he said that but I kept on rubbing his thigh.

"Now jerk me off," Tank said as if it were the most natural request in the world. I was completely shocked when he said that.  I pulled away from him and said I wouldn't do that.  "Yes you will," he insisted.  With one hand he yanked down his shorts and with the other he grabbed my wrist and forced my hand on his enormous dick.  "Do it," he commanded, keeping his hand firmly wrapped around my wrist.  I was really scared and no match for this mountain of a man.  I wrapped my fingers around his huge cock and started stroking him, pumping him.  "Yeah, bitch! That's it!"  His breathing got more rapid and his dick started swelling.

"You know," he said, "You sort of look like a girl.  You got long hair and no muscles.  Yeah, I think we're going to pretend that you really are a girl."  He was really panting now.

"Use your mouth, bitch" he ordered.  No way I was going to that, but Tank grabbed hold of my hair and forced my head to his crotch.  I sealed my lips tightly closed, but with his other hand, Tank pinched my nose so I couldn't breathe. "Open wide, slut," he said with a laugh. As I opened my mouth to gasp for air, Tank jammed his dick into my mouth.  With both of his hands now tightly holding my head in place, I had no ability to move or fight back.  And in an instant, Tank's cock exploded, filling my mouth with spurt after spurt of his hot, sticky cum.

When he was done with me, he roughly shoved me away.  "Next time, wear a dress and some make-up or something so it won't feel so gay."

"What the fuck," was all I could think, as I pulled myself up from the floor and ran out of the room. 

Taking my Sissy Husband on Vacation

My husband and I are having the most wonderful vacation together.  That's me in the photo on the left, the brunette in the black dress.  But that's not my husband in the photo! That's my new vacation boyfriend, Jerry.  I met Jerry earlier this week at the resort bar.  You see my husband is not a real man like Jerry.  My husband is a feminine, submissive sissy. 

That's my sissy husband in this photo -- the pretty blonde "lady" in the sexy gold dress.  His real name is Martin, but he is living only as "Tina" this week while we are on vacation.  And as you can see, Tina landed a handsome new vacation boyfriend too! His name is Darren.

My Tina is very, very good at passing as a woman.  He works hard at keeping his body slender through a strict diet and body-sculpting exercises.  He keeps his hair long all the time, but dyed it and had it styled especially for this trip.

Don't you think they make a cute couple?  Darren is everything that my Martin/Tina isn't. He's strong, confident and decisive.  A real Alpha male! I love seeing Tina with Darren. It seems like Tina doesn't have a single idea of his own when he's with his hunky new boyfriend -- Tina seems only capable of agreeing with whatever Darren says and whatever Darren wants to do.

I love seeing how Tina behaves when he's with a real man!  That's why I planned this vacation to a singles resort.  Although we have been out together as two women many times before -- to restaurants and bars and so on -- we had never taken a week-long vacation like this before.  For Tina -- and for me -- it is a wild, new experience!

I know my sissy husband enjoys his time as Tina.  I know that his need to express him feminine side is far too powerful for him to resist.  And being in the arms of a strong, masculine man is so exciting for him, throwing his feminine feelings into overdrive. But tricking a man to believe that you are a real woman when you are not is playing with fire!  And Tina knows this. Each moment he spends with an unsuspecting man fills Tina with equal parts excitement -- and fear that his secret will be revealed.

Tina and Darren have been an item for three days now -- and we have three days left in our vacation.  Can Tina keep up the act for the rest of our vacation without letting Darren find out the truth?  I certainly hope so.  I expect that Darren would be furious beyond belief if he learned that the woman he was falling for was really a man.

So how does Tina manage to keep his secret? Well, the first night was easy --  just some flirting and a little pawing at the resort bar, with a brief good night kiss at the end of the evening.  By day 2, things were heating up, with some heavy making out during the day and a hand job in Darren's room at the end of the evening.  (His cock is enormous, Tina reports!) 

Today is day 3 of their steamy relationship.  I caught Tina and Darren making out like crazy earlier today -- including in the swimming pool!  Now we are all dressed up for a double date together.  First we'll have some Happy Hour cocktails, then a romantic, candlelit dinner together, followed by dancing at the outdoor bar until late. It's what happens after that that has Tina very nervous.

"You better hope he likes blow jobs!" I told Tina. "And I hope you are really good at giving them.  Because he is going to expect to get some serious action from you. And since he can't fuck you, you better find some other way to keep him interested." Tina has practiced giving blow jobs on the strap-on dildo I sometimes use on Tina's backside.  But Tina has never had a real cock in his mouth -- or down his throat.

 

Of course, I've been fucking my new vacation boyfriend every chance I get this week.  We run off to his room a couple of times during the day and of course in the evening. He is amazing in bed! And I always give Tina a detailed report on my sexual encounters with Jerry.

I really hope that Tina -- and his pretty mouth -- can keep Darren satisfied and unaware of the truth. They make such a cute couple and Darren really seems rather smitten by Tina. And I can tell Tina is really falling for Darren.

Keep your fingers crossed that Tina can really pull it off. With a little luck -- and a lot of sucking -- Tina just might come home with wonderful memories of his romantic vacation with Darren -- and a tummy full of Darren's hot, sticky cum!

 

Mother's Pretty Little Sissy Daughter -- Part 2 -- Getting Ready for a Sissy Day

*** This is a continuation of a story from 2012.  To find Part 1, click on the "Sissy Jessica" Label in the right margin of the blog.  Enjoy! ***                                                                             As you already know, I have been pushing my son, Jesse, to embrace his feminine side.  In fact, I want him to become my daughter, Jessica, full-time.  Jesse is much too pretty to be a boy I think. And I tell him that almost every day.

I encourage my little Jesse to dress up as Jessica every chance he gets.  I do everything I can to get Jesse to think of himself as a girl.  I want him to let go of being a boy and to embrace a completely and permanent feminine existence.

Jesse still goes to school as a boy, but he spends all his time at home as a girl.  He has been living this way for almost six months.  He has become so naturally feminine that it has become unbearably painful for me when he reverts to being a boy.  And over that time, Jesse's hair has started to grow out long and beautiful and his body is slender and pretty as a result of the strict diet I keep him on.

As soon as he gets home from school and throughout the weekends, there is no sign of Jesse, only Jessica.

And because he spends so much time as Jessica, he has become very girlish and feminine. And he very talented at doing his hair and make-up.  Here are some photos I took of Jesse getting ready to spend a Saturday with me as mother and daughter.  He starts his day with a warm bubble bath, soaking in a tub where fragrant oils soften his skin. The experience relaxes and prepares his body and mind for a day of feminine fun.

After his bath he applies lotions to his skin before he begins to do his hair and make-up. Since he has been doing his own hair and make-up almost every day for several months, he has become a true expert at making himself look beautiful.   

I have a fun and exciting day planned for the two of us.  First, we will go to the big shopping mall that is about 20 minutes away.   We'll shop for dresses and lingerie at the big department stores.  Jessica always gets so nervous when I push him into a ladies dressing room to try on things.  Then we"ll head downtown for lunch at a restaurant we like. 

 I haven't told Jessica this yet, but there is a huge car show going on downtown.  The streets will be crowded with people and we'll probably have to park far away.  And of course the car show attracts men -- and teenage boys -- by the thousands.  So Jessica will get plenty of attention and admiring looks -- and comments, I expect -- from the men and boys we will be walking past.

Doesn't that sound like fun?

Now hurry along and finish getting ready, Jessica.  We have a busy day planned!

Sissy Priscilla Part 2 -- A Sissy Wedding Fantasy

For the past few weeks, I have been planning a very special weekend for my sissy daughter, Priscilla.  It all started when I was at a Thrift Shop and I happened to find a beautiful wedding gown in Priscilla's size for just $20.  Of course I bought it.  Here is the plan I came up with -- as soon as it was warm enough, we would rent a little cottage in the country for the weekend.  We would make the whole weekend about Priscilla's wedding fantasy!  Priscilla was so excited when I explained this to him and when I showed him the wedding dress.  I told him how we would do his hair and make up just so and then take a million photos of him as a blushing bride.  I had a few more surprises planned -- but that was all I wanted Priscilla to know about in advance.

We chose a weekend in late April and found the perfect little cottage to rent with a lovely property for taking wedding photos.  When the weekend finally arrived, I thought my darling little Priscilla was going to burst with excitement!

We drove out to the cottage on Friday afternoon, after Priscilla had come home from school and had a chance to change out of his boy clothes and into his girl clothes.  I already had everything we needed packed in the car so off we went.  We had a light dinner and afterwards I dressed Priscilla in a lovely vintage Vanity Fair peignoir set in the softest peach.  He looked so lovely as I tucked him into bed and kissed him tonight.  I wished him sweet dreams and urged him to get a good night's sleep before our exciting Saturday.

At sunrise, I brought Priscilla some toast and tea in bed and we started our day. After Priscilla showered, we spent the next couple of hours getting him all prettied up for his wedding fantasy. He started with his hair which was now almost down to his shoulders.  I watched him as he brushed in hair out in the mirror.  He seemed so happy and so natural getting ready to be a bride for the day.

Next I helped him into the lovely vintage gown I had bought for him.  I buttoned up his dress in back.  I felt so happy having the opportunity to dress my lovely bride-daughter -- even though my only child was a boy!  Since I never had a real daughter of my own, I thought this day would never come for me.  Yet here I was -- the happiest mother-of-the-bride that ever was!

Then he finished doing his make-up and voila!  My little boy was now a lovely, blushing bride.  He looked so beautiful!  I felt so proud and so happy as I looked at my little boy-bride.  

We spent the next 20 minutes pinning a wreath of fresh pink and white roses on his head.  He insisted that it had to be perfect.  It took me about ten separate tries to get it positioned to his satisfaction.  I was astonished just how much my little boy was acting like a real bride on her real wedding day.  Finally his floral crown was just right and he was complete!!!!

I picked up my camera and started taking photos for the next two hours.  We took photos everywhere -- in the cottage and around the lovely grounds. I could tell that my sweet Priscilla was having the time of his life pretending to be a bride for a day. 

I was happy that my sissy son was having fun, but as his mother I also felt some sadness.  Of course I knew that as a sissy, my son had no real friends -- and had certainly never had a real romantic experience of his own.  Real boys shun sissies like my son.  They really have nothing in common after all and could never be friends.  And sissies are too weak and too fearful to develop meaningful relationships with girls.  So while I was delighted to bring joy into Sissy Priscilla's life for one afternoon, the fact that it was just a pretend fantasy made me a bit sad.



But I had more surprises in store for Priscilla this afternoon -- something that he would never have anticipated.  I was nervous that perhaps I had gone too far -- but I was also far too excited to stop.

 

"Priscilla, darling," I called after taking a few dozen photos by the pond.  "I think it is time for us to go back inside now."

I could see a hint of disappointment on Priscilla's face when I said that, assuming that his day as a bride was coming to close.  But of course, he had no idea what further surprises I had for him.

A Boyfriend for my Sissy Husband -- The Conclusion

By the time Danielle woke up, it was already dark out.  His eyes were blurry and his head -- and his ass -- hurt. A lot. He managed to read the clock on the end table and it said 9:25!  Danielle had told is wife that he would be home by 6:00! He had been asleep for several hours. What had happened?  Danielle fumbled for a light switch.

"Martin?  Martin?  Where are you?  Did you know it is after 9:00?  I really need to get home now.  My wife is going to kill me!  Martin?"  But Martin was nowhere to be found.  Martin was long gone Danielle had slept because Martin had crushed several Ambien tablets and put them in Danielle's champagne.

Danielle ran to the bathroom and looked in the mirror.  He looked awful.  His make-up and hair were a total mess.  And there was Martin's cum caked on his face and in his hair.  "Martin!  Where are you?" he wailed again.  He looked for his purse so he could at least comb his hair and fix his make-up but he couldn't find that either.

But he did find an envelope propped up against the champagne bottle with "Danielle" written on it. Danielle opened the envelope and pulled out the letter inside and started reading it:

Dear Stupid Sissy Slut --

By the time you read this I am long gone.  How does it feel to have my semen drying deep inside your sissy ass-pussy and in your throat and on your face?  Does it feel like you've been used as a worthless sissy cum bucket?  It should.  Because that's exactly what you are.

I made you tell me that you loved me. You shouted it while my dick was up your ass! But I want you to know that you meant nothing to me.  You are just a weak, worthless sissy bitch.  Your only value is as a place for real men like me to leave our sperm.

I can't believe how easy you were to manipulate.  You believed every word I said.  I have never met anyone more stupid or more gullible in my entire life.

By the way, I took you purse and your phone.  And I took back the diamond heart necklace.  I will give that to someone I actually care about.

Good luck checking out of the hotel -- the front desk is expecting you to pay.  The room cost $950. I'm not sure how you will handle that without your purse, but I don't really care.

I am sure that you will never forget me.  But I want you to know that I have already forgotten everything about you.

Martin

Danielle had to read the entire letter twice to begin to comprehend what it was saying. And when it sank it, he began to cry.  And cry. His feelings were crushed. He collapsed to the floor, sobbing so hard that he struggled to breathe. His heart was broken and he felt like such a fool and such a failure. Martin's letter was right -- he was just a worthless sissy bitch.

The crying continued for some minutes but as his thoughts cleared, Danielle began to focus on some practical problems he had like getting home and paying for the hotel.  There was no choice but to call his wife and have her come rescue him. So that's what he did.

"Where the fuck are you?" I screamed into the phone when he called.  "You said you would be home at 6:00 and now it's nearly 10:00!  Where are you?"  I was really enjoying this.

Danielle confessed that he wasn't really downtown but instead at the Inn on the Pier and I responded with well rehearsed surprise.  Danielle had to spill everything -- his lying to me, the diamond necklace, having sex with Martin -- everything.  My anger in response was volcanic and Danielle had no defense.

I took my time driving down to the lake and picking him up.  He looked absolutely awful!  His hair was a tangled, gooey mess and his make-up was smeared. Mascara was running down his cheeks from all the crying. The girls at the reception desk couldn't help but giggle when they saw Danielle, a total train wreck, walk through the lobby. I paid the room charge which gave me yet one more stick to beat Danielle with. I had purposely parked my car several blocks away so Danielle could enjoy a nice long "walk of shame" down sidewalks crowded with people out for Saturday night.

Danielle cried and cried the whole way home.  The poor little sissy must have been near total emotional collapse with the combined effect of his extreme heartbreak and his total humiliation.  He repeatedly blubbered about how sorry he was. I remained shocked and furious -- even though he had done everything exactly the way I had hoped he would.

Danielle's waterworks had mostly subsided by the time I pulled the car in the garage.  I turned off the engine but before getting out of the car, I said to him, "You know, Danielle, you have truly disappointed me in so many ways.  Your little "affair" -- and especially your lies to me -- have changed everything. I have made a decision. From now on, you may continue to live here, serving as my maid, keeping the house spotless, making my meals, doing my laundry -- everything -- but I do not want to have to see or hear you.  Ever!  You will do your chores when I am asleep or out of the house or in our -- I mean, my -- room. Otherwise, when I am home, you are to become invisible. You will stay in the storage room in the basement, as quiet as a church mouse. That is where you will live starting immediately. And this is how things will be until -- and if -- I decide that things will change. Do you have any questions?"

The totally defeated little sissy just shook his head. "I can't hear your head shaking. I asked you if you have any questions?" I said with anger welling up in my voice.

"No, Ma'am.  No questions." my sissy whispered meekly.

Then I exploded on him, slapping him violently across the face until my hands hurt. "I told you that I don't want to hear you! What part of that didn't you understand!?!" I was screaming out loud but laughing inside.

The poor confused sissy just bowed his head in total subservience demonstrating that he understood.

"I'm going to bed now. After I'm upstairs you can get out of the car. In the morning after I leave for the day, you can move your things out of the master bedroom and into the basement."

And then for the coup de grace. "Since you were unfaithful to me, I have decided that I am going to have an affair of my own."  Whatever color was left in Danielle's face drained away immediately.  He was devastated. I had succeeded in completely breaking him!  I had restored the proper balance to our dominant wife/submissive sissy husband relationship.

I smiled as I thought about Danielle's diamond heart pendant, hidden from view, hanging between my breasts.  Just imagine how Danielle will feel when he learns that I am going out with Martin next Saturday night!

A Sissy's Dinner Date Fantasy - Part 2

Within a week of posting my profile, over 200 men had written to me!  I read every single message that I received. Then I carefully studied each man's profile and photos and I wrote flirty notes back to several of them. It didn't take long before I had actually scheduled a date with one of them!

For my very first date I had selected a man that seemed particularly promising. He name is Mark Jensen and he was in his mid-40s, divorced and a bank executive. He described himself as being six-foot-two and in excellent shape. And best of all were his photos! He was very handsome, with strong, chiseled features. His dark hair had a bit a grey at the temples.  One of his photos was taken at the beach -- with his shirt off exposing his muscular chest and shoulders!

We exchanged several emails and then we talked on the phone. I had practiced my girly voice and he didn't suspect a thing. In fact, he said my voice was sexy. And at the end of our conversation we agreed to meet for a date on Friday night!

I couldn't stop thinking about my big date all week. Even though I owned two pretty dresses that I could have worn, I decided I needed something even more special. I went to Macy's and spent $400 on a gorgeous black dress and another $200 on some sexy sling-backs with 3 inch heels.

On the night of our first date, I met Mark at Le Maison, the fanciest French restaurant in town. He was already sitting at the bar when I walked in. He looked just like his photos -- tall, handsome, sophisticated. He seemed very happy when he saw me for the first time. He gave me a quick peck on the cheek as he greeted me and the Maitre d' walked us to our table.  

My dinner date was just heavenly. Mark was a perfect gentleman and I felt like a perfect lady. He ordered a very expensive bottle of wine which was wonderful. We chatted about this and that. Mark mentioned several times during dinner that I looked very pretty -- which made me blush each time. Being with Mark made me feel like I was one of the beautiful, enchanting women in the romance novels I had read. 

We had a second bottle of wine and our conversation became flirtier. I was having so much fun -- it was like a dream come true.  

As dessert was being served, Mark got out of his chair and gave me a big kiss -- right there in the restaurant! It was so spontaneous and so romantic!

After dinner, Mark walked me to my car in the parking lot. But the evening didn't end there. We made out in the parking lot for another twenty minutes. Mark pressed me up against my car while he frenched me hard. He was so strong and forceful. I could feel his dick getting hard as he rubbed against me. It was so exciting!!! His hands even drifted up to feel my breasts -- he had no idea he was squeezing silicone falsies. He practically begged to see me again on Saturday, but I said no -- not because I didn't like him, but because I already had other plans for tomorrow night!

You see, I had already arranged a date with another man for the very next night!

After I got home from my exciting first date as a girl, I put on a sexy nightgown, some soft music and made myself cum, looking at Mark's profile photos, imagining that our wonderful date hadn't ended in the parking lot.

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!

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's DisneyWorld Vacation -- Part 3

Stepmother and I awoke early and drove to the Magic Kingdom.  My visit to the other parks had been...unusual.  In the end,  I guess I had fun -- even though Stepmother made me go dressed as a girl.  I had dreamed of visiting DisneyWorld all my life and so far it was even better than I had imagined.  And Stepmother had never been nicer to me than she had been over the past couple of days.  But today we were going to the Magic Kingdom -- the very heart of DisneyWorld.  Stepmother had me dressed as a girl again.  I was wearing the black tank top and capri pants that I had worn to Epcot.  At least I wasn't wearing the flowered sundress she made me wear yesterday!

As we approached the Magic Kingdom we drove past a giant banner that read "Happy Halloween!  Disney Costume Contest at 3:30 and Parade at 4:00!"  I had forgotten that today was Halloween.

Stepmother drove past the entrance to the Magic Kingdom parking lot and drove up to one of the big hotels at DisneyWorld .  We parked and went into the hotel.  I kept asking Stepmother where we were going but she wouldn't answer.  That's when I noticed that we were following signs to the "Bippidi Bobiddi Boutique".  When we arrived at the "BBB" I discovered what it was:  It is a little "salon" where Disney employees dress little girls up in Disney Princess costumes and make-up for their visit to the park -- this is all true.  And Stepmother was registering me for an appointment!

"Well hello there.  You must be Alice," said a perky lady in a Fairy Godmother costume.  "Good thing you made a reservation," the lady said to Stepmother.  "We've been booked solid for today since August!  All the girls want to be dressed as Princesses on Halloween. " 

I was terrified.  What was Stepmother doing?  Was she crazy?  There was no way I was going to put on some kind of costume and go to the Magic Kingdom.  Besides, this was for little girls -- like 5 year olds -- not for teenagers.

"Stepmother," I whispered urgently, "I don't want to get dressed up in a costume!  I'm not doing this!"

Stepmother roughly grapped me by the arm and dragged me to a quiet corner.  In a low and threatening growl she said to me, "Don't you dare argue with me.  Who do you think you are?   You are going to do whatever I tell you to do.   Or do you want me to show your father the photos and video of you prancing aroung Disney Studios in your pretty little sundress?"

Oh no!  Anything but that!  I was completely trapped.  I couldn't say a word.  I just stared at the floor, completely defeated. 

"I thought so," Stepmother said with a wicked smirk.  "Now start co-operating and don't make me angry.  And besides," she continued with a softer voice, "We're far from home and no one will ever know."

And so I went back to the lady at the front desk.  "Is everything alright, sweetie?" she asked me.

"Yes," I replied softly.  "I just thought that I was...too old to do this."

"Oh nonsense," the lady replied with a laugh.  "We get big girls in here all the time -- especially on Halloween."

  "Now, who do you want to be dressed up as today?  Snow White?  Cinderella?  Ariel?" Stepmother asked.  I could see that she was enjoying my humiliation.

"I...I...I..." I just could think or speak.

"Oh I know," the salon lady said.  "All the teenage girls want to be Alice in Wonderland.  And your name is Alice, isn't it?"

"Oh yes, that sounds perfect!  Don't you agree, Alice?" Stepmother replied.

I just stood there, numb.

Before I knew what was happening, I was led back to a small cubicle where a couple of ladies started working on my outfit and my make-up.  First they pinned a long curly blonde wig on me and put me in an outfit with a short skirt and stripped tights.  Stepmother made me pose for some photos before announcing that she wanted to see a different outfit and a different wig.

Then they tried a long straight wig on me.  Stepmother took more photos.  I was close to tears.  But my nightmare continued. 

No, my Stepmother said, she didn't like this one either.  She also shot me a look that clearly said to put a smile back on my face -- or else.

Then the ladies brought out a longer, more feminine Alice in Wonderland costume.  The dress fell to just below my knees and it had puffy short sleeves.  The outfit included a flouncy petticoat and a ruffly apron that was tied snuggly around my waist. They added a long wavy blonde wig with a big velvet bow.  The final touch was a pair of high heeled Mary-Janes.

"Perfect!" my Stepmother proclaimed when they showed her this look.  "Oh Alice," she gushed.  "You look just lovely!"

And so we left the salon and walked through the hotel and entered the Magic Kingdom.  It was awful.  People kept coming up to me to take photos -- and Stepmother insisted that I oblige.  I was made to pose with strangers while friends and family snapped photos.  It seemed like an endless parade of teenage boys wanted to have their picture taken with me.  Most threw an arm around my shoulders.  A few grabbed my ass or surprised me with a kiss as their photo was taken.

With all the attention and posing for photos, I didn't even get to go on many rides.  We mostly went on the kiddie rides like Small World and Teapots and Dumbo.  Stepmother wouldn't let me go on the more exciting rides.

At 3:30, Stepmother brought me over the to the back of Cindarella's castle.  It was time for the costume contest.  I told Stepmother that I didn't want to watch the contest, but she wouldn't listen.  But then I realized that I wasn't watching the contest, I was entered in it.  I was up on a big stage while hundreds of cameras flashed and people clapped.  And to make a long story short, I won first place in the the teenage girl category. 

Before I knew what was happening to me, I was standing on a parade float standing next to the tennage boy winner -- a tall, dark haired boy named Eric who dressed up as Prince Charming.  We we instructed to stand on the float, to wave to the crowds, while holding hands!  I tried to find some way out of this embarrassing ordeal, but of course Stepmother wouldn't hear of it.

So there I was, dressed up in a pretty Alice in Wonderland costume, being featured in a parade going down Main Street USA at DisneyWorld.  Thousands of people were staring at me, clapping and cheering.  Of course, thousands of cameras and video cameras from all over the world were capturing my moment of shame.  And all the while I was holding hands with big tall teenage boy.  Oh dear!

And just when I thought my parade nightmare was ending, as we stepped off the float there was a crew and cameras from the Disney Channel there to interview me.  They asked me dozens of silly questions and I gave short, simple answers in my girlish voice as I tried to sink into the floor.  And then they asked, "So, Alice, what do you think of your Prince Charming?  Isn't he handsome?  It's every girl's dream to be with a handsome Prince Charming, don't you think?" 

Oh God! "Uhhh, uhhh, uhhh," I stammered, "Yes, I guess so."  I blushed a deep crimson.

After what seemed like hours, I was released from the TV filming.  Stepmother and I went back to the salon where I returned my costume and changed into my other clothes.  I was exhausted, humiliated and very angry with Stepmother for doing that to me.  At least this ordeal was over.  I was so happy that we were on our way back to the hotel.  That's when Stepmother said, "I was talking to Eric's parents and since the two of you looked so cute together, we've decided that we will all go out to dinner together tonight.  Isn't that nice?"

"But Stepmother!" I shrieked.

"Oh don't worry, Alice sweetie," Stepmother answered.  "I picked up a really cute dress for you to wear tonight!"

HAPPY HALLOWEEN!

Sissy Ginger's Tears

Poor little Sissy Ginger tried to fight back the tears as he stepped off his Master's plane.   Wearing nothing but his prettiest bra and panties, Sissy Ginger walked to the Jeep that was waiting at the edge of the runway.  His Master's guards and driver were enjoying watching the humilated and completely exposed Sissy make his way to the waiting car.  

Six months ago, the Master had forced his sissy to undergo extreme feminization surgery and training.  The sissy's face had been sculpted into a thing of great beauty.  His body carved into graceful, delicate curves.  The massive doses of hormones had given the sissy small, soft, lovely breasts that were now filling out his elegant French brassiere. 

Sissy Ginger's lips were very sore from the collagen treatments he had just received earlier that day, but that was not why he was crying.  Nor was he crying because he was forced to parade around outside in front of his Master's rugged and leering employees wearing only his pretty lingerie.  No, Sissy Ginger was crying because he knew that he would probably never be allowed to leave his Master's private island.  He was now trapped here to serve his perverted and cruel Master as his permanent sexy sissy love slave.

   

Sissy goes to the bad part of town

All dolled up and wearing one of his prettiest party dresses, Mistress drove poor little Sissy Sabrina deep into the bad part of town.  It was already past midnight and the streets were mostly deserted.

Without a penny or a credit card in her purse, Sissy Sabrina would have to find her way home somehow.

"Please Mistress," the Sissy pleaded.  "Don't leave me here.  This area is so dangerous and we're miles from home.  I can't be out in this part of town dressed like this -- especially this time of night.  I'll be completely defenseless.  Please, Mistress, please!"  Sissy Sabrina started crying, overcome with fear with what was about to happen to him.

"Hush now,"  Mistress demanded.  "Nobody wants to hear a Sissy complain.  You look so pretty and so dainty, I'm sure some man -- or men -- will offer to help you.  Maybe you'll meet a nice man who will be happy to drive you home in exchange for wrapping those pretty lips around his big hard cock and slurping down all his cum!  Or if you're really lucky, maybe some man will take you home with him, keeping you safe in his bed until morning."  The Mistress was laughing at her own cruel joke.

"Now get out of the car, you sissy faggot, and I'll see you at home in the morning -- maybe."