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."


Saturday, December 10, 2016

Taking Delivery of My New Sissy -- Part 1



Yesterday was the happiest day of my life. You see, I took possession of the new Sissy I had ordered from Ms. Trainer's Feminization Service. When I set eyes on my new Sissy boy, well my heart nearly stopped beating -- and my great big dick got instantly hard! 


When I arrived at Ms. Trainer's I was led into a private reception room where my sissy was waiting for me.  He was patiently kneeling on the floor, his skinny, frail little body barely concealed by a flimsy, sheer black lingerie set.  I thought he looked like a little angel.  His skin was pale and soft, his face was made-up perfectly, and his perfect titties were visible through his sheer lacy blouse.
I had gotten addicted to sissies about 5 years ago after my second wife left me.  I never had much luck with women.  They won't tolerate my abusive behavior and my insatiable need for sex. That's when I started hanging out at tranny bars and picking up sissies for one-night stands.  It was easy and I could treat them like shit -- and they seemed to enjoy it.  But I grew tired of the bar scene and the drag queens that I was having sex with weren't doing it for me any more.  

That's when I learned about Ms. Trainer's Service.  For an enormous sum of cash (don't worry, I'm rich) Ms. Trainer said she could provide me with a trained, transformed sissy that would meet my every requirement.  Well that's what she did and she exceeded my expectations.

My new sissy is simply gorgeous.  At first I couldn't take my eyes off his perfect little sissy body.  But then I noticed his big, beautiful hazel eyes.  I was entranced.  I knew I had found the sissy of my dreams!




"Your new name is 'Gwendolyn'," I announced.  "And you shall call me 'Daddy'.  Or 'Sir'  Any Questions?" 

"No questions, Daddy...Sir," my new sissy answered immediately and meekly.

"Good," I responded.  "Now, tell me about yourself.  Tell me where you come from and how you came to be here," I asked.

Sissy Gwedolyn seemed surprised by the question at first but after a moment started to answer.  "Well, Daddy, Sir," he started.  "I was born in a town outside of C..."

Before Sissy Gwendolyn could even start his first sentence, I slapped him hard across his pretty sissy face. "Nobody cares about who you were or where you came from," I snarled.  "As far as we are concerned, your entire life started today, right here, when you met me. I am your life.  I am everything.  Beyond me there is nothing.  And without me, you are nothing.  Do you understand?"

"Yes, Daddy Sir.  Yes, yes, I understand.  Please forgive me.  I am so sorry.  That will never happen again," Sissy Gwendolyn managed to blurt out knowing that he had badly transgressed.



"Now suck my dick," I commanded.  Sissy Gwendolyn did exactly as directed. As he unzipped my pants and pulled down my briefs, he gasped -- either in admiration or more likely terror -- at the size of my monstrous cock.  He quickly regained his composure and focus. He pulled his pretty shoulder length hair back away from his lovely face and went to town on my cock.  My new little sissy knew exactly what he was doing in the cock sucking department!  He kissed, licked and sucked my rock hard dick until it exploded in his pretty little mouth.  He eagerly swallowed every single drop of my cum as if it were the most expensive and delicious champagne in the world!



Sunday, September 25, 2016

My Sissy Neighbor -- The Conclusion: Honeymoon

A lot of time has passed since my last post.  And a lot has happened for my sissy sister, Anita.  The biggest news is that Anita got married!                                                                                                                                                     A very handsome, divorced lawyer (his name is Jackson) was looking to buy a home and Anita became his realtor.  One thing led to another, and before long, they were dating.  Six months ago,  Jackson proposed to Anita, giving her the biggest, most beautiful diamond ring I have ever seen!  Of course Anita said yes!  Here are some lovely photos from their "Engagement Shoot."  Isn't Anita exquisite?
 The wedding was intimate and lovely. I was the Maid of Honor and of course mom was the Mother of the Bride!  And, as you would expect, Anita was the most beautiful bride ever!!!





Here are some photos from their honeymoon in Hawaii that Anita posted.  Here she is in a lovely black and white print dress that I helped her pick out.  Anita loves how this dress shows off her every curve.  Of course, she isn't wearing a bra underneath a dress like this.  I'm sure that Jackson is so pleased to have snagged the gorgeous Anita to be his bride and to have this lovely creature hanging on his big strong arm as they stroll around this tropical paradise. And Anita told me all about the hot sex they had during their honeymoon.  Apparently, Jackson has quite the sexual appetite -- and the equipment to go with it!  Anita said their honeymoon was a continuous round of eating, drinking, dancing, swimming and fucking!   



And here's Anita lounging by the pool. She loves putting her crazy curves on display in her sexy swimsuits. She knows that every guy around the pool can't take their eyes off of her -- even when their wives and girlfriends are right there!  Just check out Anita in her blue one-piece.  It can barely contain her giant boobs!  I love it! 

I am so happy that my sissy neighbor has found her new life as a successful business woman, a beautiful, voluptuous lady, and a devoted and loving wife of a handsome man. It has been a wonderful experience for me watching this amazing transformation and journey. And through it all I guess I lost a sissy neighbor and gained a sister. 





Monday, August 29, 2016

My Sissy Neighbor -- Part 11: Some BIG Changes

As you know, Anita decided that it was time to become a woman for real.  Anita had been living an working as a female for some time very successfully.  But he made up his mind; he wanted his body to finally match the woman he was inside.  One important motivator was his love life.  Anita was attracting the attention of lots of very desirable men -- but Anita could never let a relationship develop because "he" was not really a "she".  Yet.

The process took some time.  Anita had consultations with several doctors.  He started hormones.  And several months ago he took the plunge and had the complete operating -- top and bottom, if you know what I'm talking about.  There was a tiny amount of facial surgery, but since he was so pretty already, this part was very minor.



Anyway, I was somewhat surprised -- and delighted -- when I realized some of choices Anita made.  Most obvious was his chest!  He opted for really big boobs!  And they looked great on him.  And now that he has these killer tits, he just loves showing them off.  Just look at some of these photos!  These are just two of the dresses he bought recently that put his tits on full display for everyone to see.































I was so impressed with Anita's new boobs that I decided to have a boob job too!

And Anita's dick is long gone too.  No more late night hand jobs for my sissy neighbor.  But we still see each other a lot and usually sleep together in the same bed when we're together.  But now we're not secret lovers.  We're sisters.  Although I will admit that when we are alone together getting ready for bed, I can't take my eyes off of her amazing body as she gets undressed.  I think she knows I enjoy looking at her; she always takes her time and ensures that I have a good view as she gets dressed and undressed.