Mommy's Pajama Sissy -- Part 8

When Tammy and Steve arrived at Steve's parents' home, Steve quickly poured himself a stiff drink.  They had already started having a conversation about exactly who Tammy was and Steve was beginning to come to terms with the fact that the beautiful girl he had been French kissing on the dance floor wasn't really a girl at all.

But Steve wasn't angry or upset.  He really mostly seemed confused and conflicted.  He had fallen very hard for Tammy and it was a struggle to incorporate this new, shocking information with what his eyes and emotions were saying.

"Do you want me to go?" Tammy asked at one point when Steve seemed to be out of questions and the silence hung heavily in the room.

"I don't know.  I don't think so. Maybe if we just spend a little time here together we can figure out what exactly we are feeling and what we should do next," Steve suggested.

So they sat quietly together on the couch for a few minutes.  Steve broke the silence saying, "God, you even smell fantastic."  That comment broke the tension and Tammy giggled a little.

"Steve," Tammy started, "I think you like me as a girl. And I know I like you. So maybe, just for the rest of the evening, we could both go on pretending that I'm really a girl."

"But what would your mother say? Do you think she wants this to be happening?  Do you think she wants you, her son, hanging out alone with an older man who, just a few minutes ago, was kissing you on the dance floor?!?"

"I think my mother has the hots for you just as much as I do. If I wasn't here, I bet she would want to be! But I'm guessing you have that effect on girls' mothers," Tammy offered. "So no. I don't think my mother would have any problem with me being here with you tonight. I think she would be happy that I've having this sort of experience with such a nice and handsome man."

Steve didn't have an answer to that. So Tammy continued, "So, if I really was your girlfriend, what would we be doing right now?"

"Making out, I guess. Is that what you want to do?" Steve asked.

"Yes!" Tammy breathed as he wrapped his arms around Steve's strong neck and kissed him hard.  And Steve kissed him back. Steve pushed Tammy down onto the couch and climbed on top of him.  Their kissing and their breathing became harder.  As did something in Steve's pants.

"If I was really your girlfriend, what would you want me to do now?" Tammy whispered.

"I'd want you to pull down my zipper and take out my dick and start to stroke it," Steve replied. And that's what Tammy did.  Tammy was amazed by how huge Steve's cock was -- many times bigger than his own little one.  And it seemed to grow bigger with each gentle stroke.

"May I put it in my mouth?" Tammy asked.  Steve could only nod.  Tammy kissed the end of Steve's rock hard dick, and then licked it, and then pulled it into his mouth.  Steve's eyes were closed and he was making quiet moaning sounds so Tammy figured he was doing it right.  "Oh that feels so good," Steve moaned.  "So good."

After playing with Steve's dick in his mouth for about 10 minutes, Tammy said, "I want you to make love to me. Treat me like a real girl and fuck me.  Please."

"Let's go upstairs to my bedroom," Steve replied.

When they got there, Steve stripped naked. "Are you going to get undressed?" Steve asked.

"Oh, no. I don't want to be naked. I need to be wearing girl's clothes to feel like a girl," Tammy explained. "Give me a minute." And Tammy exited Steve's bedroom.  A moment later, Tammy returned wearing a black satin and lace nightgown. "How's this?" Tammy asked with a smile as he twirled in front of Steve.

""Did you take that from my mother's lingerie drawer?!" Steve asked with some distress.  Tammy nodded yes with an enormous smile on his face. "Oh, God, I'm going to be in therapy for years because of you." Under the silky nightgown, Tammy was still wearing his bra and padding, so he had the shape of  a woman and Steve couldn't help but be excited by the image of a sexy woman standing before him. 

"Wow," said Steve, "You look amazing. I am so turned on right now." And with that, the two lovers climbed into bed.  Steve positioned Tammy on his side, with his bottom facing Steve.  Steve lifted the hem of Tammy's nightgown, exposing his soft little bottom.  Steve applied some lubricant and warned Tammy that it might hurts a little since it was his first time. Steve began to gently work his giant, rock hard dick into Tammy's virgin sissy pussy.  With each stroke, Steve's cock penetrated deeper and deeper into Tammy. Soon, Steve's thrusts became harder and quicker, his moaning louder, his grip on his feminine lover tighter. And as Steve came inside of him, Tammy's own little penis also exploded into the soft, silky fabric of the nightgown that was rubbing against him.  

For Tammy, the experience was quite painful -- but also exquisite. Allowing his body to be given over for the pleasure of a real man. To feel a real man plant his hot sticky seed deep inside his body. To surrender completely to the needs of the woman that lived inside of him.  It filled him with a sense of happiness and fulfillment unlike anything he had ever experienced.

As Steve's dick began to soften, he started to withdraw from Tammy's backside. Tammy reached around and grabbed Steve's ass. "No," he said. "Please leave it inside of me for just a bit longer."

As they lay there, still wrapped tightly together, they both fell asleep for a few minutes, both feeling exhausted and content.

When they awoke, Steve kissed Tammy again and said, "I think I need to drive you home now, darling."

Don't look so sad, little Sissy!

Don't look so sad, my little Sissy Princess!  After taking a long break, I have decided to come back and add some more delicious Sissy fantasy stories!  Isn't that wonderful news?                                                          There are a few stories that I started writing down a few years ago that I will finish up and get posted.  Some are sweet and soft and romantic stories that will make all you little Sissies swoon with pleasure.  Some are a little bit rougher and scarier.  These stories will make you little Sissies squirm with fear -- and envy.                                                                                      So turn that frown upside down, little Sissy!  Mistress Trainer is back with more stories for you.                                                                                Now get on your knees and open that mouth nice and wide because I have some gentlemen friends in the next room that are dying to meet you!

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.

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."

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!

My Sissy Neighbor -- Part 4: Sweet Sissy Kisses

After working until 11:00, Anita comes back to my house to change back into Andy before heading home.  Mom always greets Anita at the door with a big hug.  She's usually in her big fluffy bathrobe because it is late, but she is too worried to go to bed until she knows Anita is home safe.

Andy's home life is more than just terrible. Andy is deathly afraid of what his father would do to him if he ever found out about Anita.  As it is, Andy's father is abusive towards him in many ways.  Andy is right to be scared, if you ask me.

Anyway, I usually hang out with Anita and chat while he changes.  I'm usually in my bathrobe too. I usually hang up his things while he gets undressed and washes off his make-up. He puts anything that needs washing, like his bras and panties and stocking, in a hamper and my mom will put them in the laundry with our stuff during the week.  (No chance of mixing up Anita's underwear with mine -- his bras are 34DD and mine are 36A!)

We talk about all sorts of stuff while he's undressing. One night, a while ago, after he had told mom and me about kissing some of the customers at the club, I asked him, "Do you like it when you have to make out with men?"

"I guess I don't mind it too much. I don't think I'm gay but I like the idea that men find me desirable and sexy. It's very exciting and..." Anita searched for a word.

"Validating?" I offered.

"Yes!" Anita exclaimed. "Validating."

Looking at Anita and talking about kissing was making me feel funny. He hadn't started taking off his make-up yet and he looked so beautiful. "Can I kiss you?" I asked.

"Sure, if you want to," Andy replied. We sat together on the edge of the twin bed that was in the dressing room. I put an arm around him and looked deeply into his pretty eyes. As I went in for my kiss, he delicately closed his eyes, just like I imagine he does with his customers at the club. I was seriously turned on!

I could smell his perfume and taste his lipstick as we kissed.  I wrapped my arms around his slender body, feeling the corset he wore beneath his dress to give him that sexy wasp-waist shape.

We made out for about 15 minutes before I broke it off; it was late and Andy still needed to change and get home. "That was amazing!" I panted. "You are so sexy! And you kiss like a girl!" We both giggled at that.

"And so do you," he replied.  "I assume."

I needed a moment to figure out what he meant by that.  Then I realized -- he had never kissed a girl before.  Poor Andy!

After that, making out became part of our routine every night before Anita changed back into Andy!  I just love kissing my sweet, beautiful Sissy Anita.

My Sissy Neighbor -- Part 2: Seeing is Believing

After seeing Anita's photo, I'm sure most of you don't believe that Anita is really Andy.  But it's true.  I swear.

I told you that Andy comes over to our house around 5:00 in the evening.  Mom has turned the spare bedroom into "Anita's Dressing Room."  Anita's clothes and shoes and stuff -- and there is a lot of it -- fill the dresser and the closet. Mom found an old vanity table and a cute upholstered bench at a tag sale. She also bought a really good lighted make-up mirror for Anita.










When Andy arrives, my mom always greets him with a big hug, knowing that his own parents are such losers that he gets no affection from them. She then brings him a cup of tea to the dressing room and Andy begins to transform. Sometimes I like to sit in the room with him while he does his make-up and gets dressed.  It's amazing what he can do.  Here are some photos I've taken of Andy changing from boy to girl.

Here you can see how he's already done his eyes and eyebrows and is starting to do his contouring. You can see his hair is still pulled back the way he wears it to school.  Without his make-up on you can see how young he really is.  But with his make-up on he looks so much older and more sophisticated.  Andy told me that the manager at Club Satin believes that Anita is 26 years old.  But as you can plainly see, he is much younger than that.












The contouring he does is super complicated but it is really effective.  I've been trying to learn to do this myself, but I'm not nearly as good at is as he is.  And his finished look -- dramatic, sultry, glamorous -- is perfect for working as a hostess in a dark night club. 




And then his is nearly done.  He uses some light powder to achieve the finishing highlights.  Then he brushes out his hair and -- finally -- puts on his lipstick.  When he's done there is absolutely no sign of Andy -- only Anita.  He puts on his bra and padding, his jewelry, his outfit for the night and his 5 inch high heels.  And then he heads out into the night to his life as a night club hostess. 


He is so beautiful! 

My Sissy Neighbor -- Part 1

Andy has lived next door to me ever since I can remember.  We've been in the same grade and attended the same schools since kindergarten.  Andy has some big secrets that only my mom and I know.

Andy has always been...different.  I have known that he is a sissy for many years.  When we were little, he used to come over to my house almost every day after school.  He never wanted to play boy games or run around outside. Instead he loved staying inside with me, playing with my Barbies together, having tea parties with me and my stuffed animals, playing dress up in my mother's closet -- that sort of stuff. To me he was just like a sister and best girlfriend all in one. My mother saw all of this.  She was concerned about Andy and his sissy tendencies. But she was more concerned about his home life.  Andy's parents were a mess -- his father unemployed and abusive and his mother a big drinker.  There was always a lot of yelling going on in their house. Mom was happier when Andy was at our house.  At least she knew he was safe and felt cared for here.

As Andy got older, to other kids at school he just seemed to get weirder. When we got to high school, he had let his hair grow long and even partially bleached it.  He was also incredibly skinny and his clothes were all black and goth. He usually kept the hood of his black sweatshirt pulled up over his head.  And even if you did see he long hair, he kept it pulled back in a sloppy pony tail in a way that made him look more like a rocker than a sissy. He really kept to himself; he didn't have any friends except for me. The other kids thought that he was so odd that they didn't even bother to tease him. But I knew he wasn't so strange. He just had a secret life that he wanted to protect and being a loner was the best way to do it.

You see, almost every night, Andy disappears and his alter ego, Anita, comes alive.

Andy has told his parents that he works as a dishwasher at a restaurant on the other side of town six nights a week -- Tuesday through Sunday.  They don't bother to check up on him and since he contributes the $300 every week to help pay for the family's rent money, no one complains.  But Andy doesn't wash dishes at a restaurant.  Andy, or rather Anita, is one of the hostesses at Club Satin, an expensive "gentlemen's club" downtown. And he doesn't earn $300 per week. He earns about $1,500 every week.  It's true.

And when he's all dolled up at Anita, no one would ever know that "she" is really a "he."  I mean, just look at this photo!  He's incredibly beautiful as a girl!

How does he do this with no one else knowing?  Because my mom and I help him.  He leaves his house around 5:00 in the afternoon and drives his beat-up used car over to my house where he pulls into our garage. He then takes the next hour or so changing from Andy to Anita.  And he is absolutely amazing with make-up and his hair. He keeps all his supplies at our house: his make-up, his dresses and shoes, his bras and panties, his jewelry, his padding for his hips and boobs, the works.

His ratty pony-tail gets combed out into a pretty style that just brushes his shoulders.  His lips are crazy full and sensual.  He eyes look huge and sexy underneath his heavy false eyelashes.  Then around 6:00, when he is ready to head to work, he lets mom and me admire the finished product.  We are always incredibly complimentary about how pretty he is.  I know he likes hearing the support especially from my mom.  She tells him to "be careful" every time before he gets back into his car and drives to the club. 

A Boyfriend for my Sissy Husband -- part 4

Martin had ordered some champagne from room service which was a very good idea because even though Danielle was excited by everything that was happening to him, he was also very frightened.  The champagne helped to settle his nerves.

"Martin," Danielle said softly, "I need you to know that I've never done this before."

"That's OK," Martin replied coolly, "I've done it lots."

Danielle wasn't exactly sure how this was going to work. If he took off all his clothes, he wouldn't look like a girl anymore and that would spoil the effect for Danielle -- and maybe for Martin too. So while Martin was in the bathroom, Danielle pulled out a sexy nightgown that he managed to stuff in his purse before leaving.  He slipped his nightgown on over his well-padded bra and panties. Danielle freshened his lipstick, put on a bit more perfume and checked himself out in the mirror.  He was very satisfied that he looked pretty and sexy in his nightgown. And with his bra and pads in place, he had all the right curves.  His fantasy was intact; he was a beautiful woman about to have sex with a handsome man.  He slipped on the hotel robe and waited.

Martin emerged from the bathroom looking very sexy. He was also wearing a hotel robe. They made out for a few heavenly minutes. Then Danielle dropped his robe to the floor, revealing his sexy nightgown. Martin looked admiringly at Danielle and gave him a little wolf whistle. "Let's get under the covers," he said.  And so they did. And then the action began.

Martin took control and directed Danielle every step of the way.  And Danielle did everything -- everything -- Martin told him to do.  It started with Danielle stroking and massaging Martin's cock, which made it get stiff.  Danielle was amazed by how big Martin's cock was! It seemed to keep growing and growing the more Danielle played with it. It was at least ten times as big as Danielle's tiny penis.

Then Danielle was instructed to kiss and suck on Martin's cock.  Martin started pumping slowly back and forth in Danielle's mouth. Danielle struggled to fit much of Martin's giant dick in his mouth but he tried his best.  Then Martin's rocking started to get faster and stronger.  After a few minutes, Martin was forcing powerful, deep thrusts into Danielle's mouth, forcefully holding Danielle's head in place so his cock was snaking into Danielle's virgin throat.  And that is when Martin started cumming for the first time.  It seemed to Danielle that a gallon of hot semen was flooding into his mouth.  "Swallow it!  Swallow, bitch!" Martin growled.  Danielle never heard him talk like that but figured it was what real men say when they're excited.

Danielle's ass was next and Martin was ready to do again after just a few minutes rest.  Martin smeared lube on his dick and on Danielle's ass. He positioned Danielle on all fours and then he went to town.  For Danielle, it was very painful at first, having a giant cock rammed up his butt for the very first time. But after a few minutes it started to feel good and Danielle enjoyed the feeling of giving his man such pleasure. Just like before the thrusting start slowly but picked up speed and power as Martin's excitement built. He fucked Danielle hard.  With one arm wrapped around Danielle's waist, he used his free arm to spank Danielle's ass -- hard -- in time with his thrusts. "Say you love me, bitch!  Say it!  Say it now and say it loud!" he yelled at Danielle. Danielle didn't like being called "bitch" but he did as he was told.  "I love you, Martin.  I love you!" he said as loud as he could. As Martin came inside Danielle's ass, Danielle's little dick exploded too, spilling his cum all over the sheets.

Martin wasn't done.  He had taken three Viagra pills as soon as they had checked in.  He shoved his filthy dick back into Danielle's mouth and Danielle didn't protest. After several minutes of more rough thrusting, Danielle could tell Martin was about ready to cum again. Danielle prepared himself to swallow another flood of semen.  But Martin didn't cum in Danielle's mouth. Instead, Martin pulled out of his mouth just before cumming, shooting wads of hot cum into Danielle's face and hair.

Martin climbed out of bed and let out a little chuckle as he looked at the cum soaked sissy mess lying there. "Here," Martin said, handing Danielle his champagne glass, "have a drink."

 "Are you coming back to bed?" Danielle purred.  "I want to snuggle."

"Sure, I'll be there in just a minute," Martin said.  Danielle pulled the sheets up to his chin and promptly fell asleep.

4 Million Page Views! Get Ready for a Sissy Celebration!

Congratulations all you Sissies, Admirers, Masters and Mistresses! We have now reached 4 million page views! Isn't that wonderful!  I want to personally thank all of you for visiting my site and making this blog such a success.

Obviously, this proves just how many sissies are living out there -- all around the world -- in need of a firm, guiding hand to help them on their sissy journeys and to fulfill their sissy destinies.














Now it is time to celebrate!  I want all you Sissies reading this to join in our worldwide celebrations -- just like Sissy Ginger is doing.  I sent Sissy Ginger an email earlier with instructions. And Sissy Ginger is very obedient and will exactly as he is told.


First you need to do your hair and make-up. It has to be perfect for tonight.  Make sure those pouty, pretty lips are red and glossy -- your mouth will be definitely be put to work tonight!



Then put on your sexiest undies. Look at how pretty Sissy Ginger looks in his bra and panties!  Sissy Ginger has been on a strict diet for the last six months and it has really paid off, don't you think?  And he has tucked his little sissy clitty away so well -- you can hardly see any bulge at all in his pretty panties.

Did you buy a special dress for tonight?  Sissy Ginger bought two. Which do you think he will wear tonight?  I hope he picks the silver one.  I love how it sparkles!  I know he will get extra attention tonight if he wears that one.




















      








Sissy Ginger grabs his purse and his car keys and heads out to the big party. Tonight there are going to be big celebrations for our 4 million page views in LA, New York, Miami, Berlin, Marseilles, Hong Kong and Sydney! Sissy Ginger lives in Miami and  has been instructed to go to the club on South Beach that I have reserved for tonight.  The club will be filled with sissies and Admirers.  There will be music, an open bar -- and no rules!

Sissy Ginger will get a lot of attention at the club tonight because he is such a beautiful sissy. Men will be competing with each other for the opportunity to flirt with him, to dance with him, to run their hands over his soft, slender body.



Oh dear, it looks like Sissy Ginger has been drugged and taken back to some man's home.  Sissy Ginger's night is going to start getting really freaky now!  I think that's the perfect way to celebrate!  

Tell me, Sissies, how are you going to celebrate our 4 million page views?  Remember Sissies, you are required to leave comments to express your sissy feelings for all the world to see!

Lots more weird and wonderful Sissy stories coming soon!  

A Sissy every Weekend -- Part 7. After the Dance

Caroline followed me back to the bedroom.  She sat down on the edge of the bed and gently placed a hand on my shoulder.

"I'm sorry I teased you like that," she said.  "I really do appreciate what you did for me tonight.  And I would like to show you how grateful I am."

I had no idea what she was suggesting.

"Now take off your dress and put on your nightie and I will be back in a minute."  Caroline disappeared into the bathroom.

I forced myself to stop crying and dried my eyes with a tissue.  I stripped off the pretty dress, the stockings and the bra and panties I had worn to the dance and slipped on my pink nightgown.  Caroline emerged from the bathroom wearing only her bra and panties and carrying a bottle of lotion and a small towel.  "Now I want you to just lie back and relax," she said as she sat on the edge of the bed.  She looked so beautiful wearing just her underwear.  I tried not to stare but I couldn't help it.

As I laid back, Caroline lifted the bottom of my nightgown.  She squeezed some lotion onto her palm and began to gently stroke my little penis.  I had never felt anything like this before.  Here was the girl I loved so much, wearing only her bra and panties, giving me a hand-job!  My little penis instantly became erect.  As Caroline stroked me I tried not to think about how much different I must be than her boyfriend Robert.  Robert was big and strong and masculine; I as dainty and feminine, my skin was soft and my cock was tiny.

I couldn't believe this was really happening.

Caroline stopped pumping for a moment.  "Now don't make any noise, Sweetie.  We can't let anyone know what we are doing.  Do you promise to be quiet?"  I quickly nodded in agreement.  Caroline resumed playing with my cock with her soft, lotion-covered hands.

"Does that feel good, Tiffany?" Caroline whispered into my ear as she continued to pump my little penis.  "Ohhhh, yes," was all I managed to reply.

And then I started cumming.  My little cock just exploded, spurting and spurting, over and over.  Caroline smiled down at me while I orgasmed.  "Well," Caroline said.  "It looks like someone really enjoyed that!"  She kissed me on the forehead and went into the bathroom to wash her hands.

When Caroline returned she again at on the edge of my bed.  "You really were wonderful to go to the dance with me tonight."  She stroked the my cheek with her soft fingers.  "Now get some sleep."

She moved to her bed. "Oh, by the way.  Robert's parents have invited you, me and Mark out for brunch tomorrow morning.  I already said that we are going. It will be fun and I know Mark will enjoy seeing you again.  And if it all goes well, who knows, maybe I'll be able to show you how grateful I am again."  With that Caroline turned off the light and climbed under her covers.

Caroline was completely manipulating me.  She knew she had me under her spell and I was powerless to resist.  Tomorrow I would be out again -- with a boy who thought I was really a girl.

I struggled to fall asleep, but when I did, I had dreams about Caroline -- and Mark.

A Sissy Every Weekend -- Part 4. Going to the Mall

On Saturday afternoons, after the twins are done with their sports, we often go shopping. Sometimes we take taxis to the glitzy stores downtown.  Other times we all pile into Aunt Jenny's big SUV and drive to the malls just outside of town.

The girls and my aunts just love shopping! They can try on shoes and dresses for hours. I guess I don't mind going along with them too much. When we go to the fancy stores, they always insist that I try on lots and lots of dresses. Sometimes it seems like they think I am some kind of living Barbie doll to play dress-up with.

Someone will always find some pretty dresses in my size. Then two or three of my cousins will pile into the fitting room with me while I strip down to my bra and panties. Then the girls will help zip me into the dresses. There is a ton of giggling and they love to take photos of me as I model the outfits they found for me. 

This weekend we went to the Galleria Mall where there are several big department stores. Here's a photo of me wearing  a fancy designer dress that I tried on at Nordstrom's that I could never afford.








Here's another dress that the girls insisted that I try on. I struggled to squeeze into this tight, clingy red and orange mini-dress. 

They all said that this dress made me look "so hot!" and that "guys wouldn't be able to resist me wearing this dress."  I don't mind dressing up like a girl, but I don't like it when the girls start talking about how "sexy" I am or how I must "really turn men on" and things like that. That kind of talk always makes me very uncomfortable. But even when I tell them to stop teasing me that way, they often keep doing it anyway.


















Then Aunt Jenny found this sweater and skirt set and suggested I try it on. Everyone said I looked cute in it and I thought it looked nice on me. Aunt Jenny said it was on sale and she insisted on buying it for me.  

Our next stop was Neiman Marcus. All of us tried on the summer dresses that were on clearance. Here's me in a pretty striped dress that everyone thought looked cute on me. Mother said it was a very good deal so she bought it for me.

Our last stop was Saks. Everybody tried on a bunch of outfits there. Aunt Jenny tried on a pretty blue dress but didn't like how it looked on her. She said that it would probably look better on me. So she dragged me into a fitting room and stripped off the dress. Wearing just her bra and panties, she helped me put on the dress she had just been wearing. When I came out of the fitting room, Mother and all of the girls gushed over how pretty I looked. Aunt Jenny insisted on buying it for me. As the sales lady was wrapping it up, Aunt Jenny said, "It's the perfect dinner date dress, don't you think?" All the girls giggled when she said that and I turned bright red.

A Sissy Every Weekend. Part 2. Girls Night Out

It is Friday evening, and once again I am dressed up like a pretty girl. Here's a picture that mother took of the outfit that I am wearing tonight. Everyone is telling me that I look lovely, and even though I am really a boy, I feel beautiful. Maybe I was born to be a sissy.

But I am getting ahead of myself. Let me tell you how I got here.

Every weekend, mother and I drive to the city where her sister, my Aunt Jenny, lives. Aunt Jenny has a 4 bedroom townhouse.  Aunt Jenny has one bedroom and the twins share a bedroom.  When we visit, mother sleeps in the guest room and I share a room with my cousin Caroline. Of course everyone knows that I am really a boy, but everyone treats me like I am just another girl. Some years ago one of the twins had decided that my name should be Tiffany, so that is what I am called.









Today, mother dressed me in a short pink skirt and a cute lacey top for the drive to my aunt's house. When we arrive there, everyone greets us warmly. Aunt Jenny runs up and gives me big hug and kiss. She tells me how pretty I look and how much I was missed during the past week. Mother then joins her sister for cocktails in the living room while I go join my cousins in the den. Usually my cousins are watching TV or playing video games when I get to their house.

My cousins are all super nice to me.  They treat me like a girl cousin. But they know I'm a boy and sometimes I think they feel sorry for me. When I arrived tonight, the girls all said hi to me.  Then Maddie, one of the twins, said, "Hey, I think that skirt used to be mine."

"Yeah," Caroline retorted,  "But it looks much better on him than it ever did on you."  The room fell silent.

"Oh sorry," said Caroline to me when she realized what she had just said. I'm not to be called "him" when I visit.  "I didn't mean to tease you."

"I know," I replied honestly.  I knew she was trying to tease her older sister, not me.

Living as a girl in a townhouse with five girls/women every weekend, I often see just about everyone -- my aunt, my cousins -- in their underwear...or less. Since Caroline and I share a room, I see her getting dressed and undressed every day that I am there. She doesn't mind.

Since all of my cousins are older than me, I have an enormous collection of hand-me-down clothes: pretty dresses, cute shoes, lacy underthings. That's why Maddie recognized the pink skirt I was wearing had been hers. I also have some of Aunt Jenny's old clothes. And of course, some things have been bought just for me.

After a little while, Aunt Jenny came into the den and announced the plan for the evening. "Great news, girls," she announced. "I got tickets for the ballet tonight!" All three cousins squealed with delight. "Now you girls go get changed. Wear something nice and be ready to go 20 minutes."

Caroline and I went to our room. She stripped off her jeans and t-shirt and started rummaging for a dress to wear. She looked amazing in her bra and panties. I tried not to stare but I couldn't help it. I had a terrible crush on her, but she had a real boyfriend and could never feel the same way about me.  

I opened the armoire that held my girl clothes and pulled out a pretty black blouse that I hadn't seen before. It had sheer sleeves and a collar and cuffs that we covered with rhinestones. "Oh, that used to be my mom's," Caroline said as she saw me looking at it.  "That would look great on you. Maybe pair it with that blue print skirt you wore to the restaurant a couple of weeks ago." I found the skirt and agreed that it would look nice. I took off the outfit I had been wearing and slipped on a pair of smokey black stockings. I put on the blouse and skirt and asked Caroline how I looked.

"Wow," she said. "You look fantastic.  Here, let me help you with your lipstick." She  grabbed a tube of "Bombshell Red" lipstick and painted it on. "Wait until the others see you!" see said excitedly.

When I stepped downstairs where the others were waiting, they all fell silent when I walked into the room. I thought something was wrong. Finally, after a moment, mother said, "Oh, Darling, you look BEAUTIFUL!" All the others agreed.  It made me feel all warm inside to be the object of so much attention and affection.

Mother insisted on taking about a hundred photos of me and my cousins. Mother spent so much time taking photos of me that we were almost late for the ballet!