A Sissy Refresher -- Part 1

"Come out here now, Erica," Ms. Trainer called.  "Your wife and her lover are here and they are dying to see the new you."

Tentatively, timidly, Erica -- formerly my husband Eric -- entered the room.  I gasped.  My Erica was gorgeous.  He was wearing a lovely silk dress in the palest gold.  His hair was perfectly styled.  And he was so skinny!

"Don't be frightened, Erica," Ms. Trainer said gently.  "You look lovely.  There is nothing to be embarrassed about."  Despite Ms. Trainer's reassurances, Erica seemed terribly nervous.  I could tell that he was on the verge of tears.  "Come along now, Erica.  Be a good girl."   Erica walked across the room and stood in front of Roberto and me. He delicately held a cute clutch purse in his manicured fingers.

"Ms. Trainer," I said. "He's lovely.  I mean...fantastic."  Ms. Trainer smiled with satisfaction.

"I thought you would be impressed," she replied.







I had deposited Erica here just twelve weeks ago.  Of course he was already a fully feminized sissy, having gone through Ms. Trainer's transformation process some years ago.  But now he looked so beautiful, so elegant.  And so incredibly skinny.

"How did you get him to be so skinny?" I asked.  Erica was already very, very thin before.  But now -- wow!

"Well, it's not too complicated.  It's a combination of a severe -- and I mean severe -- diet, combined with a lipo/body sculpting procedure, combined with some amazing corsetry that he's wearing that I get from Japan.  It's terribly uncomfortable -- but the results are so worth it!  Erica, don't you just love wearing your corset?"

Erica spoke for the first time.  "Yes, Ms. Trainer, I love wearing my corset."  His words were barely a whisper.  He seemed so upset.  I could see tears welling up in the corners of his eyes.  And he was trembling very slightly, perched about his silver, strappy high heels.







"Ms. Trainer," I asked.  Why is he trembling like that?"

"Well," she replied, "It has been quite a difficult twelve weeks for our lovely Erica here.  He has really done his best to cooperate with our refresher program for advanced sissies.  But it hasn't been easy, has it Erica?"

"No, Ms. Trainer.  It has not been easy," came his breathy reply.

"There, there.  Try to relax, Erica.  We wouldn't want your tears to ruin your make-up now, would we?

"No, Ms. Trainer," he replied.

Ms. Trainer continued.  "Our little sissy Erica may also be nervous about what awaits him when he returns home with you and Roberto.  All of this extra training he has received is for a purpose.  And he is well aware of just how attractive -- enticing, really -- he has become.  And I think he is nervous about what you have in mind for him."

"Ah, I understand," I replied.  Of course the experience of the last twelve weeks would have been both punishingly cruel, as well as plant seeds of anxiety for what his life would be like when we returned home.

"Now come over here, Erica," Ms. Trainer ordered.  "Let me help you off with your jacket."  Erica obediently stood still while Ms. Trainer undid the buttons in the back and slid the jacket off of my sissy.

As the jacket came off, Roberto said, "Damn!"

"Damn is right!" agreed Ms. Trainer.  "That is one fantastic looking sissy!"

I couldn't believe my eyes. With the little jacket off, Erica posed there in front of us, in his strapless dress.  His shoulders were impossibly skinny and delicate.  He was obviously dying with shame as Roberto and I took in this sight.  Again, I thought Erica was about to start crying.


"Now turn around Erica.  Let's show your wife and Roberto how pretty you are from the back," Ms. Trainer instructed.  I loved how Ms. Trainer talked to Erica in a voice you would use speaking to a little child. But when speaking to Roberto and me, she would talk about Erica as if he wasn't even in the room.  There was a sly, cruel -- but also very humorous -- way to everything Ms. Trainer did with her sissies.




Erica turned around and Roberto let out an involuntary whistle.  "Oh my God!" I gasped.  "His ass...it's simply perfect."

Ms. Trainer smiled with satisfaction.  And even with his back to us I could sense Erica's deepening sense of shame as we all talked about his cute round ass.

"Erica, go back into the other room and put on one of your other dresses.  I know your wife and Roberto will enjoy seeing you model your cute new outfits."  And with that, poor Erica minced out of the room to change.

A Pretty Little Sissy for Ms. Jones -- Part 2

"Good," said Ms. Jones with a satisfied smile. "Because I want us to become very special friends." And with that she took of the blouse and skirt she had been wearing and stood in front of Veronica in just her bra and panties. Sissy Veronica's eyes nearly popped out of his head having never seen a woman undressed in real life, let alone a sexy, curvy goddess like Ms. Jones.

"Now tell me, Veronica, tell me that you want to be a beautiful woman like me.  Say it!"

"Oh, yes, Ms. Jones, I want to be a beautiful woman just like you!"  Ms. Jones smiled with great satisfaction.

"Now come here, Veronica," Ms. Jones instructed.  She wrapped her arms around the sissy's narrow shoulders and pulled him close to her enormous breasts.  She kissed him hard on the lips and let her hands start to explore Veronica's skinny, smooth body.

"Now, Veronica, I want you to start kissing me all over my body," Ms. Jones instructed and sissy Veronica did as he was told, starting at Ms. Jones' neck and working his way down to her breasts, her belly and beyond.

As Ms. Jones looked into her new sissy plaything's eyes, she thought about all the fun they would have together.  She thought about how exciting it will be to attack her sweet young thing with an enormous strap-on dildo, taking Veronica's sissy virginity away from him.  She thought about how much fun it will be to invite her friends over -- men and women -- and to share her sissy plaything with them.  She started thinking about having a couple of giant studs spit-roast the little sissy -- one dick in his mouth, the other up his sissy pussy -- while she filmed it for the internet.  That thought made her pussy very wet!

"Now, Veronica, you have to understand that your are a sissy and that you now belong to me.  That means you have to do everything I tell you to do, without question or hesitation.  Do you understand me?"

"Yes, Ms. Jones, I understand," Sissy Veronica softly replied.

"What do you understand, sissy?"

"That I am your sissy and that I now belong to you.  And that I must do everything you tell me to do," the sissy repeated back.







"Good, sissy," Ms. Jones replied.  "Now take off your bra and panties and put on this condom.  I am going to let you fuck me with your itty-bitty sissy-dickie-wickie."  Ms. Jones laughed.

Sissy Veronica stripped as ordered and put on the condom.  Ms. Jones instructed him exactly what she wanted him to do to bring her pleasure.  And he did it.  She had the most explosive and satisfying orgasm she had had in years.  Sissy Veronica came as well, of course.  It was the most exciting moment of his life.





"Remove the condom very carefully, sissy, and hand it to me.  Now close your eyes, tilt your head back and open your mouth."  Sissy Veronica did as ordered without question.  And as he did, Ms. Jones emptied the contents of the condom into the sissy's open mouth, squeezing every last drop of sissy cum out onto Veronica's tongue.  "That's a good sissy," Ms. Jones breathed. "Swallow it all, every drop.  Sissies have to eat cum every day, so get used to it.  Some days it will be your cum, but many days it will be another man's cum."







Ms. Jones handed Sissy Veronica the white bra and panty he had been wearing earlier.  "Put these back on and wear them under your clothes tonight and at school tomorrow.  You better be wearing them when you come to my house immediately after school.   Do you understand?"

Sissy Veronica put on the bra and panties and got dressed to go home.  "Yes, Ms. Jones.  I understand completely."

A Pretty Little Sissy for Ms. Jones -- Part 1

This is Ms. Jones. She is a forty-ish divorcee with an incredible body and some pretty kinky ideas. While she dates a lot of men, she rarely feels satisfied with conventional relationships. She's tried being with other women and with groups -- but nothing has ever really felt completely fulfilling. That all changed when she got to know Vernon, the boy who lives next door.

Ms. Jones and Vernon have a secret that they share. Actually they have several secrets. One secret is that Vernon is a little sissy fairy who loves to dress up and act like a girl. The other secret is that Ms. Jones has turned sissy Vernon into her feminized love toy.

Ms. Jones had known for some time that Vernon was a little sissy. She had discovered that Vernon was accidentally using the Wi-Fi signal from her house to access the internet. With a little help she was able to monitor the internet sites Vernon visited and even read his emails and blog posts! Well, Ms. Jones learned that Vernon was into some wild stuff. Little Vernon was visiting a bunch of hardcore tranny sites -- including this blog! -- and was exchanging emails with some other sissies and admirers. Thinking that all his internet activity was anonymous, Vernon wrote long emails and posts about how he loved dressing up like a girl, how he longed for someone to turn him into a woman with large breasts, and on and on.

Ms. Jones found it very exciting to be the only person in the world who knew Vernon's secret. She would sometimes subconsciously touch herself as she spied on her little sissy neighbor's internet antics. Over time she found herself thinking about Vernon obsessively, finding the idea of a girly-sissy boy arousing. She decided to take action.

One day when Vernon was taking the garbage cans out and was all alone, Ms. Jones approached him. "Vernon, I have something very important to talk to you about. But I am only going to say this once so listen carefully. I know you are a little sissy crossdresser." Vernon was about to say something to try to deny it but Ms. Jones would have none of it. "Shut up!" she snarled sharply, causing Vernon to jump. "I told you to listen to me and I meant it!" she said in a growling, commanding way. "I know you are a sissy faggot and that's OK with me. I don't plan on telling your mother or anyone -- if you do what I ask of you. Do I have your attention?"

Vernon nodded meekly. Ms. Jones noted with satisfaction how easy it was to dominate him with just a few strong words. She also noted that even dressed as a boy he looked rather girlish, his long brown hair hanging over his rather delicate features.

"Now, I think you are going to like my proposal. Starting tomorrow, you are to come over to my house everyday after school as well as on weekends. I have plenty of girly clothes and make-up and everything you need to have your little sissy fun. I will even help you. How does that sound?"

She already knew the answer. Even though it was hard for him to admit it, the offer was like a dream come true.

The next afternoon Vernon came over to Ms. Jones house as she had instructed. She greeted him with a big hug and brought Vernon up to her bedroom where she had him undress completely, right in front of her. Ms. Jones laughed when she saw how tiny Vernon's little dickie was. Vernon was so embarrassed but completely powerless to do anything other than accept the humiliation he was experiencing.










Ms. Jones reached into a dresser and pulled out a a very pretty white bra and panty set. She explained to Vernon that this underwear belonged to one her girl lovers who was just about the same size as Vernon. She helped Vernon pull on the panties and to tuck his tiny dickie. She then fastened the bra behind his back. "Vernon," she explained, "you are going to have to learn to do this all by yourself." She then brushed out his hair and put some make-up on him. She slipped a pair of sexy, strappy black heels onto his feet. She told him to lie back on her bed as she started to take photos of him. "Do you like this, Ver..." she hesitated. "Do you like this, Veronica?" she asked. 

"Oh, yes, Ms. Jones. Very much," he replied breathlessly.

"Do you like dressing like a girl, Veronica? Are you a little fairy sissy? Well, are you?"

"Yes, Ms. Jones," he replied. "I am a little sissy fairy and I like dressing like a girl."

"Good girl, Veronica," Ms. Jones cooed. "We are going to have a wonderful time together."

As Ms. Jones continued to snap photos of sissy Veronica in his pretty white bra and panties, she asked, "Do you like me?"

"Um, yes. Of course I do," he replied.

"And do you think I'm pretty, Veronica?" she continued.

"Oh yes, Ms. Jones. I think you are beautiful. I think you are the most beautiful woman I have ever seen."

"And do you wish you could have great big, soft titties, and a pussy, like I have, Veronica?"









"Oh, yes, Ms. Jones. Yes," Vernon panted.

"Good," said Ms. Jones with a satisfied smile. "Because I want us to become very special friends." And with that she took of the blouse and skirt she had been wearing and stood in front of sissy Veronica in just her bra and panties.

Sissy Priscilla Part 3 -- Mother's Wedding Surprise

After I had taken about a million photos of my beautiful sissy son bride, I told him that we should head back inside.  I could tell he was sad when I said that, sensing that our bridal fantasy day was wrapping up.  But I had other ideas.  In fact, the fun might be just beginning!

As I said earlier, sissies have such limited lives -- no friends, no romance.  But I knew I could change that.

You see, at the same time that I was making arrangements to rent the cottage and buy flowers for today, I had also gone online to see if I might be able to find a fantasy "groom" to make Priscilla's wedding fantasy complete.  There are plenty of websites out there for men looking to meet sissies. My challenge was to find the right one.  I posted some details of what I was planning for my little sissy and, needless to say, I got hundreds of responses from horny men wanting to have some dirty action with my sweet sissy son.  But one profile stood out from all the others -- a young, tall, handsome man, clearly well educated.  He seemed to understand what I was looking for in a "dream date" for Priscilla.  I arranged to meet him in person and I liked him immediately. His name was Kurt. 

So on the day of Priscilla's wedding, while Priscilla and I were taking photo's outside, Kurt arrived at the cottage and waited patiently for us inside. When he saw us starting to walk back toward the cottage, that was his signal to come out.  Little Priscilla was so frightened and worried when this tall man walked out of our cottage and started walking straight towards us.  "Now, now, Priscilla," I reassured. "Don't be frightened.  In fact I know this man.  His name is Kurt and I invited him."

Priscilla looked so confused and scared.  Kurt confidently strode up to Priscilla.  "Hello, Priscilla," he said.  "I am Kurt.  Your groom.  Your husband.  For today." 

Well, it took some time for Priscilla to compose himself after much reassurance from me. "Come, come, Priscilla," I said.  "Play along.  This is all part of making today's fantasy complete."  After a while, Priscilla relaxed, mostly because Kurt was so charming and gentle with him.  Before too much longer, I was able to get Priscilla to smile and pose for some photos with Kurt.  Here's the first photo I took.


Well, after the first photo was done, I was able to take about two hundred more as I asked them to pose in various locations around the pond.  With each passing moment, Priscilla became more relaxed around Kurt and seemed to ease more naturally into his role as the petite bride to Kurt's manly groom.

"Now a kiss!" I shouted.  Priscilla was shocked when I said this.  Kurt wisely went in for a gentle peck on Priscilla's forehead.

"Oh that won't do at all!" I cried.  It's time for a real kiss."  And I guess Priscilla agreed.












Kurt pulled Priscilla hard against him as Priscilla closed his eyes and allowed Kurt to kiss him for a very, very long time. I was delighted to see my little sissy son experience romance for the first time in his life.  I took dozens of photos of this lovely embrace.



We went back inside the cottage where I insisted that Kurt and Priscilla act out a wedding ceremony while I took even more photos.  I had arranged for some wedding flowers for the living room to set the mood.  

"Do you, Kurt, take Priscilla to be your wife?" I intoned.  "I do!" said Kurt while Priscilla beamed.


"And do you, Priscilla, take Kurt to be your husband?"  "Oh yes, I do!" replied my eager and delighted sissy son.  "You may kiss the bride." I instructed Kurt.  And Kurt did as I told him, scooping Priscilla up in his arms and kissing his lovely bride.



















"And now for your first dance as husband and wife!" I shouted and pressed play on the CD player.  John Legend's "All of Me" began to play.  Kurt expertly led Priscilla around the living room in a gentle, slow, romantic dance.  As the song came to an end, I decided it was time for me to make my exit.  "Well, three's a crowd," I said.  There's a light dinner and a bottle of champagne for you two in the refrigerator.  I will be up in my room.  Have fun.  And congratulations!"  Priscilla giggled as I left.


At about 6:30 the next morning I heard Kurt leave the cottage and drive off in his car.  I came downstairs and found Priscilla, in his vintage peach peignoir set, sipping on a cup of coffee, looking rather disheveled -- and a bit embarrassed.

"Well, well, well," I said. "And how is the new bride this morning?"

Priscilla waited a moment, finally answering, "A bit sore, actually."  We both broke out in laughter when he said that.  I gave my sissy bride son a great big hug.  

"I hope you enjoyed your wedding fantasy, darling," I said.

"Oh yes mother.  That was the most wonderful day -- and night of my life."

Kurt continued to be a frequent visitor at our home after Priscilla's sissy wedding.  But those are stories for another time.

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.

Sissy Priscilla Part 1 -- Mother's Sweet Sissy Daughter

I have always known that my sweet little boy was a sissy.  At first he tried to hide his interest in everything girlish from me.  But I could always tell that he was more interested in girly things than a little boy should be.  He so enjoyed sitting with me at my vanity as I did my make-up and standing next to me in my closet as I picked out what dress to wear.  He was fascinated with my lingerie, my perfume, my hair curlers -- really everything that was feminine.                                                                                                                                          I knew that he secretly tried on my clothes when he thought I didn't notice.  When I thought he was ready, I spoke to him about it.  I reassured him that I didn't mind if he wanted to play dress up at home.  I told him that I thought it was sweet that he had feminine feelings and interests.  I urged him not to keep this bottled up inside and to feel safe letting his girlish feelings out at home.  At first he tried to deny what I was saying, but it didn't take long for him to crack and to admit the longings that were deep in his young heart.

These are some photos of what my son looks like now when he is at home.  Isn't he adorable?  He is so naturally feminine and girlish I sometimes forget he isn't really a girl.  He spends his days at school as a boy but after school and on weekends, he is my daughter, Priscilla.  I let him borrow any my clothes if that's what he wants to wear -- but he has a closet full of pretty outfits and drawers of lingerie of his very own. Priscilla is simply the sweetest little girl any mother could dream of for a daughter.  I don't know who is happier that there is a young girl in the house -- Priscilla or me!

For the past few years, I have been encouraging his to let his hair grow out.  His hair is now long for a boy, but I don't think anybody notices or cares; these days it seems like anything goes.  What's important to us is that his hair is now long enough that he can style it to look pretty and feminine when he wants to be Priscilla. I even take him to my beauty salon when he needs a haircut.  My stylist does such a nice job with his hair.  

We have such fun together as mother and daughter.  Here is a photo I took when Priscilla and I spent a weekend in the country.  We stayed in a cute little bed and breakfast, went antiquing, shopped for crafts and clothes.  In the evening we went to a state fair that really fun.  I noticed that a lot of the teenage boys at the fair were "checking out" Priscilla as we walked around together.  Can you blame them?  Of course not! My Priscilla looks adorable!  No one had any idea that the pretty young girl in the beret was actually a boy.