Sunday, February 4, 2018

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.

Tuesday, January 23, 2018

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.

Sunday, January 14, 2018

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.

Tuesday, January 10, 2017

Sexy Beach Sissy

Sam is a total sissy.  He loves dressing up in his sister's clothes and pretending that he's a girl. He used to do it only around the house when his parents were out.  But now that he has his driver's license, he likes to go out in public as "Samantha."  Sometimes he goes to bars and clubs. Sometimes he'll walk around the mall or the park.  But his favorite thing to do is to hang out at the beach.

He saved enough money working part-time jobs to buy an old VW van.  This is both his car and his dressing room.  Every day during the summer, he leaves the house early in the morning as Sam. He drives to a quiet place to park and climbs in the back of the van and transforms into Samantha.  He fixes his shaggy black hair in a way that looks cute and feminine.  He does his make-up -- he loves wearing lots of bright red lipstick!   He puts on a bikini with just enough fabric to hide his fake boobs. And he wears a super tight panty under his bikini bottoms so that he is perfectly flat and smooth in front. Lastly, he puts on some dangly earrings and sprays himself with a flowery perfume. Once he is satisfied with his look, Samantha continues the drive to the beach.

On most days, Samantha arrives at the beach before there is any real action there so he hangs in the van and listens to the radio. There are a bunch of regulars that are also around early in the morning -- maintenance workers, cops, vendors, lifeguards -- heading into work. Samantha knows a lot of these men by name and a bunch of them go out of their way to swing by the van and flirt with the pretty brunette girl for a little while.  Samantha's favorites are the cops and the lifeguards.

Sometimes if the cop or the lifeguard is especially cute, Samantha will invite him into the van to make-out. The really lucky ones get to go into the back of the van where Samantha will wrap those pouty, red, slick lips around their cocks and suck them off.

But that's just the start of Samantha's day.

By now the beach is starting to fill up. Samantha grabs his towel and sunglasses and heads out across the quickly warming sand. The trick for Samantha is to find the right spot on the beach where he will attract a lot of attraction from the boys hanging out there.  He knows that sometimes big groups of older boys hang out on the stretch of beach just past the pier. There are fewer people out there and it's a perfect place to throw a football around.  Samantha will find a promising group of boys and place his towel just near enough that the boys will definitely notice him.  It never takes long before one or two brave boys will venture over a strike up a conversation with the cute brunette laying on her towel.  A little flirting, a little giggling and Samantha will easily hook one unsuspecting boy.

"Would you please put some sunscreen on my back?" Samantha will ask a guy he is interested in.  No boy has ever answered "no." Samantha gets a rush of sensual pleasure feeling a boy's strong, rough hands spreading lotion on his soft shoulders and back.

Some of the boys get the chance to go for a walk down the beach with Samantha.  Samantha likes how it feels when a big strong boy wraps his arm around his skinny, exposed shoulders. His pulse quickens when a boy pulls him close as they walk side-by-side. It makes Samantha feel so feminine. The walk along the beach often leads to some making out under the pier.  Samantha likes pressing up against a strong young man while they make out.  He especially likes feeling his admirer's dick get hard as they kiss.

And the luckiest boys -- the most handsome, most muscular, most studly ones -- get invited back to the van for a special treat. He starts off by getting these boys aroused with his mouth, licking and sucking their dicks until they are nearly ready to cum, But before they do, Samatha quickly repositions himself so that the boy is on top of him. With his soft hands he finishes the job so that that boy shoots his hot cum all over Samantha's flat, exposed, lotion covered belly.  

The boys at the beach don't know Samantha's secret. But now you do. So would you go into the back of the his van with him if he invited you? Of course you would.

Saturday, December 31, 2016

Never too Late for Sissies

I often hear wives say, "I wish I had feminized my husband years ago. Now it's too late."  That is nonsense! It is never too late to feminize your husband. Just look how lovely Sissy Jessica is in his bikini!

Mary had been married to Jeff for over 20 years. Mary knew Jeff was a crossdressing sissy, but she didn't mind. She enjoyed having a husband with a feminine side who listened to her, doted on her, enjoyed shopping with her. But as Jeff experienced some set-backs at work and was starting to consider early retirement, Mary decided it was time for some changes in their lives. Mary decided that they would both be happier if Jeff took his sissy-ness to the next level and became a woman full-time -- or at least a sissy version of a woman.

Jeff resisted at first.  But that's the good thing about sissies; they have no spine and no ability to push back. So in the end, Jeff did exactly as Mary ordered and became Jessica.  And weren't the results fabulous!  Jessica looks ten -- maybe fifteen -- years younger than Jeff did when his transition began.  And look at him now!  He looks totally hot as a woman, even in a skimpy bikini.

But Mary wasn't done yet. She also decided that both she and Jessica needed to have real men in their lives. Jessica was horrified -- distraught -- by Mary's suggestion.  Jessica cried and protested but to no avail.  Mary got her way as always.  

It was easy for Mary to find countless older men online who wanted to have a sissy of their own. She eventually selected Terrence, a wealthy divorced businessman, for Jessica.  Mary arrange all the details for their first meeting and subsequent dates.  It worked out perfectly. Once in the presence of a real man, Jessica easily and naturaly slid into the role of the woman in the relationship.  That was eighteen months ago. Now Jessica is embarking on the next exciting chapter of his life -- as Terrance's wife. That's right! Jessica and Terrance got married last month and those bikini shots were taken on their honeymoon!

Jessica is in heaven being the pretty, obedient and subservient housewife for his husband.  You can see how happy he is being feminine and domesticated and servile to a real man.  He spends hours every day making himself pretty. He derives total fulfillment by being the object of his man's desire -- and by satisfying that desire with every part of his feminized body.

Tonight, Jessica and Terrance are having a double date tonight with me an my new boyfriend.  Jessica is making dinner for all of us -- for his husband, for his ex-wife that feminized him and for his ex-wife's lover!  Could there possibly be a greater expression of what it means to be a total sissy?

So my friends, as you see, it is never to late to help your sissy fulfill his destiny!

Saturday, December 17, 2016

Taking Delivery of My New Sissy -- Part 2

I kept my spent dick in my sissy's mouth until it started to go limp.  Sissy Gwendolyn expertly and eagerly cleaned every drop of cum off of it with his well trained tongue.

"Take off your top," I directed.  "I want to see your titties."  My new sissy obediently did as his master instructed.  

"Now I 'm going to fuck your pretty little sissy ass-pussy.  How do you feel about that?" I asked.

"Oh, please, please, please ram your enormous cock up my sissy-pussy," my new sissy pleaded desperately.  My dick sprang to attention once again.  I was going to fuck the shit out on this sexy sissy plaything.

As my new Sissy wiggled out of his sheer black lacy top, I was able to admire just how perfect and feminine his little sissy body was.  I took a moment to drink in his long skinny legs, his pale, soft skin and those incredible titties.  The room had mirrors everywhere -- even on the floor -- so I could enjoy the sight of my new plaything from several angles at once.  This was the best moment of my life.

Just look at my perfect Gwendolyn in the picture to the right.  I did fuck him right there.  As I fucked him he started crying, either from the pain of my giant cock up his tight little ass or from the humiliation of being another man's sex toy.  I smiled at the thought that both were true. I must have dumped a gallon of my hot sticky cum in his ass!

And then it was time to take my sissy home. While Sissy Gwendolyn and I were getting acquainted, Ms. Trainer's staff had move Gwendolyn's few possessions into my car.

"Would you like us to dress him before you take him to your car?" one of Ms. Trainer's assistants helpfully offered.

I thought for a moment.  I knew there was a heavy snow falling outside and a bitter cold wind.  "No thank you," I replied.  "He can walk out to my car dressed exactly as he is."