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 Sissy Every Weekend. Part 1. Going to Aunt Jenny's House

This is a picture of me taken last Saturday when I visited my aunt and my cousins. And while you may think that I am a girl, I am not.  I am a boy.  But this is what I look like every weekend. Let me explain.

During the week, Monday through Friday, I'm pretty much like the other boys at school.  Of course my hair is a little longer and I'm very skinny.  Also I don't like playing sports and don't really have any friends.  But other than that, I'm just another boy at school.  

But all that changes as soon as I come home from school on Friday afternoon. "Hurry up, Sweetie!"  mother will call out as soon as I step through the door. "Time for you to change so we can get to Aunt Jenny's house."  She has already packed weekend bags for both of us and she impatiently waits for me to get dressed. It has been the same every Friday afternoon since I can remember.

I know mother was disappointed -- deeply depressed, actually -- when I was born. She is very close to her sister -- my aunt -- who has three daughters; the twins are four years older than me and Caroline who is about one year older than me.   After Caroline was born my mother had hoped desparately for a little girl of her own so that she could join her sister in endless mother-daughter activities.  But since I was born a boy, that dream was spoiled.  Or it would have been if not for my mother's determination.  Mother simply decided that I would have to be a girl when we got together with my aunt and cousins.  And we all get together -- all six of us -- every weekend. 


And if you wondering, there are no men around at all.  Aunt Jenny is divorced and mother was never married.  So I'm the only one in both our families who isn't a girl. At least not really a girl.

Sometimes I wish I didn't have to pretend to be girl every weekend. But I guess I don't really mind too much. It makes my mother very happy and I love my aunt and my cousins very much. But still sometimes I wish mother would let me be a normal boy...


So my weekends begin on Friday afternoons as I change out of my boy clothes and put on my girl clothes.  Even though my cousins and my aunt all know that I'm a boy, it was decided that I should already be dressed as a girl when I arrive at Aunt Jenny's house. That way it is less confusing for my cousins, I guess. 









I start by slipping on a pair of panties and a padded bra that makes me look like I have little boobs. Wearing just my undies, I brush my hair to look prettier and put on some mascara, a little blush and some lip gloss. 

Today, mother has laid out a white lacey top and a peach colored skirt.  The skirt is very short and I don't really like that, but mother says it makes me look very pretty. She also told me to take my blue and white purse and to wear my blue shoes with the 2 inch heel and the ankle strap. 

Mother fastened a little necklace around my neck. Then she snapped a few photos of me for her scrapbook like she does every Friday once I am dressed.  


Mother tells me that it is time to go so I get into the car and we start the 45 minute drive to where my Aunt Jenny and my cousins live.

A Sissy and his Mother Have a Weekend Adventure -- Part 1

My son, Jamie, and I share a big secret.  Jamie is Sissy.  And while he tries his best to act like a boy at school, at home he is my Sissy daughter, Janey.  Over the years, Janey has really blossomed into a delightful young "lady" and I love the special times I get to spend with the daughter I never had.

Last weekend, we had the most wonderful adventure. After Jamie came home from school on Friday afternoon, we drove into the city, which is only a couple of hours away. We checked into our hotel and that's when the real fun began. Jamie stripped off his boy clothes, slipped on a fluffy bathrobe and started becoming my daughter Janey. Over the next hour and a half, Janey and I got ourselves all dolled up for a night in the city.

We finished doing our hair and makeup. I helped Janey zip up the new little black dress that I had bought for him. I let him borrow one of my necklaces and a fun oversized purse. Janey put on his favorite strappy platform sandals and he was ready.  Doesn't he look lovely!?!

We then went to the ballet which we both loved! Then we enjoyed a late dinner at a fancy French restaurant. It was marvelous.  The waiters fawned over my pretty daughter.  One even jokingly begged Janey for a date!  Janey was a good sport and giggled and blushed like a young lady would. 

Exhausted, we went back to the hotel where we slipped into our nighties and went to bed.

On Saturday morning, Janey decided that he wanted to wear his red dress.  It is very simple and yet so elegant.  And Janey knows he looks fabulous in it!  

We had breakfast at the hotel and then went to the art museum which had a wonderful exhibit on ballgowns from the 18th and 19th centuries.  Janey and I both enjoyed this very much.  We spent so much time at this one exhibit that we barely saw anything else in the museum. 

After we were done at the museum, we walked over to the Ritz Hotel where they serve the most delightful afternoon tea. Janey and enjoyed all the little sandwiches and sweets that were served.  Elegantly dressed ladies sat at all the other tables; some tables apeared to have mothers and daughters having tea together -- just like Janey and me!  I felt so fortunate to be able to share this experience with my special Janey.

After tea, we spent the rest of the afternoon shopping. At the lingerie shop I bought Janey some new bras and panties and stockings.  We then found some shoes for Janey at the big department store -- a pair of black patent leather slingbacks with a three inch heel and some cute sandals for the summer. Then we visited a couple of the designer boutiques and I had Janey try on literally dozens of dresses!  In the end we only bought one dress for Janey -- oh, but what a dress. 











We returned back to our hotel exhausted carrying all of our new purchases.  Since we were tired, we decided that we would have dinner downstairs at our hotel.  As we started to get ready for dinner, Janey asked me, "Mother, do you think I can wear my new dress tonight -- the one you bought me this afternoon?"

"Of course, sweety,"  I replied.  "I am sure that your new dress will be just perfect for tonight.  The hotel's restaurant is rather fancy and I am sure people will be dressed very nicely.  So yes, please wear your new dress."

We finished doing our make-up and fixing our hair.  Janey slipped on his new dress and modeled it for me.  "Oh, Janey," I sighed.  "You look...amazing."  A tear started to well up in my eye as I gazed at my beautiful, elegant son.

Spring Break Sissy

When I told my parents that I was going to Florida for spring break, they were really worried.  They pictured me hanging out at wild, drunken parties and stuff like that.

But actually, my spring break is very different -- but my parents don't need to know that. 

You see, I am spending the entire week as Professor Wilson's sissy!


Here's a photo of me in the hot tub with my Professor and Master.

It all started last fall when I was taking Professor Wilson's Human Sexuality class.  I went to see him during his office hours one afternoon because I needed help understanding an assignment.  He closed the door to his office after I sat down.  Before I could even ask a single question, Professor Wilson asked me, "You're a sissy, aren't you?"

I was shocked and scared by his question.  The truth is that I am a closeted cross-dresser, often having fantasies of submitting myself to be feminized and controled by a dominant man or woman.  But this was my secret.  I had never told anyone this.  How could Professor Wilson possibly know?

"I asked you a question, sissy!" he shouted.  "Don't deny it.  I know what you are.  I can tell.  It's my expertise, after all.  Now I am going to ask you again.  Are you a sissy?"

I lowered my eyes to the floor, and softly answered, "Yes," unable to resist the Professor's command.

"I knew it!" he exclaimed with a self-satisfied smile.  "Well from now on you are going to be MY sissy.  That means you will do whatever I tell you to do.  You will submit to me in all ways.  Do you understand?"

"Yes, Sir," I meekly responded.  Professor Wilson smiled again.

I now visit Professor Wilson at his home every evening and every weekend.   When we are together, he is not nice to me at all.  As I walk in the door, he instructs me on how I should dress for the evening.   I prepare myself as quickly as possible -- make-up, lingerie, a dress, stockings, heels -- the works.  He then proceeds to order me around for the next few hours.  This usually includes cleaning his house, doing his laundry and making his dinner.   If I do anything that displeases him, he throws me over his knee for a harsh spanking.  

When my chores are done and he has finished eating, he has sex with me.  He often orders me to bend over the back of the couch so he can take me from behind.  If there is a big game on TV, he makes me suck on his cock while he watches the game.  Then after he cums and I have cleaned up the mess, he orders me to get out.

My Professor/Master has helped me to understand that, as his sissy, I exist for only one reason -- to serve and please my Master -- and that my feelings have no importance.  I am just an object for him to use for his pleasure.   

Now it is Spring Break and Professor Wilson has arranged for a perfect Master/Sissy vacation.  All year I have growing my hair out and Master has kept me on a strict diet so that I would look extra girlie for our trip.  He rented a beautiful condo that has a view of the Intercoastal Waterway, a big deck and a hot tub.  He packed several pretty outfits for me to wear, lots of sexy lingerie and even two bikinis!

Master has been so nice to me since we arrived at the condo!  Of course I have to do all the chores and follow all of his orders and he has spanked me a few times.  But mostly we are passing our days and night in bed or in the hot tub.  It has been so romantic!  We have been spending hours and hours kissing and having sex.  And after he is done having sex with me, he has been letting me snuggle up against him.  I feel so safe and happy when Master wraps his big strong arms around me. 

Here we are in the tub again.  I am giving him a handjob.  His enormous, hard cock feels so good in my soft, manicured hand.  I am so content and fulfilled serving and pleasing my Master.  

I wish my Sissy Spring Break would never end.

Mr. Lane's Sissy

Last month, I told Mr. Lane, the counselor at my school, that sometimes I like dressing up in girl's clothing.  I thought that maybe I was crazy and that he would be able to help me.

Mr. Lane was really nice.  He said I wasn't crazy at all and that there was nothing wrong with having "girlish feelings."  He asked me a lot of embarrassing and personal questions. He asked me things like if wearing satin panties made me excited and if I ever thought about kissing boys.  I guess I answered the questions well because he was smiling a lot and kept saying, "That's good, very good."

He said that he would help me but that for my own good it would have to be "our little secret."  He told me that I should meet him at his house every day after school.

The first time I visited his house, he showed me a whole closet full of girl's clothing and shoes and wigs and stuff.  He said that it was important for me to "embrace my feminine feelings" and "explore and experience girlish things."  He showed me how to do my make-up and stuff.  He let me wear a dress and took some photos of me before I had to change back into my boy clothes and go home.

It's been four weeks since that first visit.  Everyday I rush to Mr. Lane's house as soon as school is out.  I do my make-up and put on girl's undies and whatever dress Mr. Lane left out for me to wear.  I hurry so that I can be all ready and look very pretty by the time Mr. Lane gets home.

Mr. Lane said that today would be very special.  I put on the pretty flowered dress and matching hair bow that he had left out for me.  I met him at the door when he got home and he handed me a big bouquet of flowers.  Then he hugged me and gave me a big kiss.  I didn't really like that but he said it was part of the process of understanding my girlish feelings.  Then he told me how beautiful I looked and that made me feel happy.

We then moved to the couch where he told me to sit on his lap.  I had never done that before and it made me sort of nervous but I did it anyway.  Then he started kissing me some more and running his hands all over my body.  I could feel that he was getting an erection.

"Today, I'm going to teach you to be a real girl," he said as he unzipped his pants.  "Now get on your knees."

The Sissy Behind the Curtain

"Martin!" my wife shouted, "Get out here.  NOW!"

My wife had caught me dressing up in her clothes a few weeks ago -- and she didn't like that one little bit.

"Don't be shy, Martin!" she continued.  "We all want to see how pretty you are."  My wife and her lover were waiting for me in the Master bedroom.  They both started giggling when she said that.

I had been dreading this moment.  During the afternoon, my wife had spent hours getting me ready.  First she did my make-up and pinned a curly brunette wig on my head.  Then she dressed me in a sexy red outfit including some strappy high heel sandals that she had picked out for me to wear tonight.  She even put some of her jewelry on me.



"WE"RE WAITING!" she yelled.

I reluctantly stuck my head through the curtain that separated the Master bedroom from the dressing area.  I saw my wife and her lover, both half naked, wrapped in each other's arms sitting on the bed.

"Come on now," my wife called.  "Come all the way out here.  Don't keep us waiting any more."








I tentatively pulled back the maroon curtain and stepped fully into the Master bedroom.

"OH MY GOD!" her lover shouted.  "I can't believe this!  What a Sissy!  He really does look like a girl!"

"Can you believe I actually married a Sissy faggot like that?" my wife asked.

"Now do that sexy dance I taught you," my wife commanded.  And with that, I began to sway and rock, wiggling my hips in a sort of burlesque dance.   "Oh yes!  That's soooo sexy!"  my wife yelled.  And with that, the couple on the bed broke down into fits of laughter.

After a few minutes my wife told me to stop dancing and to come stand next to the bed.  "Now you just stand there and watch while a real man fucks me."  As she said that, the two lovers stripped off the rest of their clothes.  My wife's lover was a big, muscular man with a huge cock.  I just stood there, wearing my sexy red lingerie, while he climbed on top of my naked wife and started fucking her.  I couldn't fight back the tears as my wife started screaming with pleasure, being fucked by such a masculine man. 

After they were done fucking, my wife sat up and looked at me with disgust.  "Aw, is the widdle sissy sad because he's feeling left out?  Well don't cry, sissy.  We have something very important for you to do.  Now get on your knees and clean my man's cock with that pretty sissy mouth of yours."

I did exactly as I was ordered.  As I wrapped my painted lips around this giant cock I realized my life would never be the same again.

Sissy Prepares to "Entertain"

Sissy Amanda's cell phone buzzed.  It was a text message from his wife.  "Leaving now.  Home in 1 hour.  Be ready to entertain."

"Home in just one hour!?!" Sissy Amanda thought with alarm.  He stopped scrubbing the kitchen floor and raced to his little bedroom in the basement.  He stripped off his maid's uniform, sat down at his vanity and got busy making himself look beautiful.  His wife and her lover would be home soon from their romantic weekend in the country and Sissy Amanda had been instructed to always look his best when they returned.  And from the text it was clear that he needed to be prepared to sexually "entertain" them as soon as they arrived.

Sissy Amanda finished doing his make-up and took a moment to look at his reflection in the mirror before putting on his dress.  He looked at his delicately arched eye-brows, at his sexy, smokey eye shadow, at the pink lipstick that coated his soft, full lips.  He burst into tears thinking about what he had become.......

Afternoon Sissy

Whenever I am home alone, I love playing dress-up.  I raid my mother's closet, her lingerie drawer, her make-up, jewerly, perfume -- everything.  She even has a long curly wig that I use to complete my look.

I love dressing up like a girl.  I feel so feminine, so free, so alive.  I love getting my make-up perfect and slipping on the wig.  I especially like wearing my mother's sexy lingerie.  Dressed like this, I enjoy staring at my pretty reflection in the mirror looking back at me.  Sometimes I take photos of myself, like this one, that I can look at late at night when I'm in bed.

But today, disaster struck.  I had the house to myself all afternoon -- I thought.  My mother was at work and my older brother was at football practice.  I was all dolled up, wearing my mother's light pink, lacy nightgown.  I was in the living room, dancing to the radio and watching my performance in the big mirror, when all of sudden in walked my brother and three of his friends from the football team.

"What the fuck!?!?" my brother shouted wen he saw me.

"Who's that?" one friend asked.

"That's my faggot little brother," he answered.  The other boys howled with laughter when they recognized me.

"He sure is pretty," the biggest of the friends said.

"Hey," another one said. "Even though practice was cancelled, I think we can still get a workout this afternoon, if you know what I mean."

"Go ahead," my brother said.  "I don't care.  Do whatever you want with him."

And with that, the three boys dragged me upstairs to my bedroom to be their "Sissy Girlfriend" for the afternoon.  Thet took turns having sex with me while the others held me down.  I tried not to cry, but they were really rough with me and it hurt a lot. 

When they were done with me, one of them said that I was cute enough to be a cheerleader -- and if I was a cheerleader then I could get fucked by the boys on the team all the time.

Hmmm.  Maybe I will...

Mother's Pretty Little Sissy Daughter -- Part 1

The day I caught my son crossdressing was the happiest day of my life.

I had come home early from work and found my son, Jesse, sitting at my vanity, putting on make-up.  He was wearing one of my cocktail dresses -- and my stockings, my high heeled sandals and, it appeared, my lingerie.  He hadn't heard me come in, so I just stood silently in the doorway watching him put on mascara, blush and lipstick.  He was completely mesmerized by his own ladylike reflection, completely entranced by the girl in the mirror. He did a very good job with his make-up; clearly he had done this many times before.

Of course, Jesse was very upset and embarrassed when I announced my presence after enjoying the show for several minutes.  He started spewing all sorts of pathetic explanations and denials.  I tried to calm him by saying that it was OK.  He settled down enough that he even let me help him finish doing his make-up.   I encouraged him to stay dressed while we ate dinner.  I treated him like a girl throughout the evening and he seemed to enjoy the experience.

So why was that the happiest day of my life?  Because I had always wanted a a daughter -- and now I had one!

That was two months ago.  Ever since that fateful afternoon, I have been working day and night to convince my little Jesse that he is too pretty to be a boy and that he was always meant to be a girl.  When he is dressed as a boy, I treat him mostly with indifference and I react harshly to any little mistake he makes.  But when he is dressed as a girl, I shower him with the affection he craves and I lavishly praise his every girlish accomplishment.  In this way I have lured him -- trapped him -- into more fully embracing his feminine side, using my love and affection as bait. 

He is now in the habit of changing out of his boy clothes as soon as he gets home from school.  My son Jesse becomes my daughter Jessica for the evening.  And all through the weekends.  He has become proficient doing his own make-up.  And with my coaching, his mannerisms and his voice have become delightfully feminine as well.  He now has a closet full of his very own dresses and his drawers are overflowing with his own bras and panties and stockings.

Recently, I have started taking my daughter Jessica out of the house at night.  We've started going to restaurants and movies together.  Tonight we are going to the ballet!   I even bought him a pretty new dress to wear.  He's very excited.  Here's a photo of Jessica doing his make-up for our big evening out.  Doesn't he look sweet?

I can't stand the idea of not having my daughter Jessica with me all the time.  I have all sorts of ideas for how we can spend more mother/daughter time together.  I'm hoping that by spending more time as Jessica that Jesse will more fully embrace life as my beautiful, sweet little sissy daughter.    

I think he will learn to love his new life as Jessica.  Don't you?

After School Sissy -- Part 2

Stepfather arranged for a lady to come the house to help me look the way he wanted me to.  She was waiting for me at the front door when I got home from school.  We went inside and she had me take off all my clothes.  With her help, I put on a pair of mother's panties and one of her bras.  She gave me a set of breast forms that filled out the cups of mother's bra and she laced me into a tight corset to give me a "prettier shape."    She sat me down at mother's vanity and for the next two hours she gave me a thorough lesson in putting on make-up.   I was taught how to do everything: putting on foundation, plucking my eye brows, putting on fake eye lashes, mascara, eye liner, blush -- everything!.    Here's a photo she took of me while I was practicing putting on lipstick.

When she was satisfied with my make-up, she had me put on a silky flowery dress and a pair of strappy high heels that she picked out from my mother's closet.  And lastly she pinned a long wavy blonde wig that was styled to look like my mother's hair.  When the lady was done with me, I didn't just look like a girl, I sort of looked like my mother!

But she wasn't done yet.  She stayed for another hour, giving me lessons on walking and sitting and even talking like a girl.

By the time the lady left, it was almost 6:00, so I had to hurry to get Stepfather's dinner ready before he got home.  It felt funny being being dressed up like a woman but I was in a rush and I didn't really have time to think about.  It was a little hard to move quickly wearing my mother's high heels.  I also tried to be careful not to spill anything on mother's pretty dress.

When Stepfather came home and saw me with my new look, including my glamourous make-up, my big boobs, and my nipped waist, I could tell he was very happy.  He was very friendly and relaxed during dinner.  After dinner, he invited me into the living room to watch TV with him. He had never done that before!  He insisted that I sit really close to him on the couch.  He even put his arm around me.  That seemed kind of strange, but it sure was better than being beaten with his belt!

That night was two months ago.  Since then, I've been dressing up in mother's clothes and doing my make-up, just as the lady taught me, every day after school.  I do my chores and make Stepfather's dinner.  And even though I don't like dressing up like a lady everyday, Stepfather is very nice to me all the time, so I guess I don't mind too much.

But recently, when we watch TV together after dinner, he's been making me sit on his lap.  He wraps his arms around me and I have to lay my head on his shoulder.  Sometimes he kisses my neck which feels really weird.

  

Sissy Goes Outside Part 2

I wasn't happy at all with the outfit the girls had picked out for me.  They had dressed me in a black bra, a while mini skirt and a very sheer blouse.  I felt half naked in the short skirt and sleeveless top.  I had also complained because I didn't like how everybody would be able to see my bra right through the blouse, but my sister just told me to shut up. 


The girls drove me to the corner of Church and Walnut.  I was so scared that I started to feel dizzy.  My sister told me not to cry or I would mess up my mascara.  When we arrived, the girls pushed me out of the car and handed me a black purse to carry.  They said they would be waiting for me at Parker Street, about a ten minute walk away.  The girls were laughing as they drove off.

I started my walk.  At first my heart was racing.  I had never been outside dressed like this.  The air felt cold on my bare arms and legs.  I was very aware how sheer my blouse was and that made me very nervous.  But after a couple of minutes I started to relax a bit.  There were no other people out on the sidewalk and the few cars that drove by didn't seem to notice me at all.  I was even beginning to enjoy the feeling of being out dressed like a girl.  I slowed my pace a bit, stood up a little taller and even tried to put a little wiggle into my hips as I walked.

Before long I was only about two blocks away from Parker Street, my destination.  I could see the girls in their car waiting at the corner.  They started shouting to me things like "You're almost here!"  and "Just a few more feet to go!"  I smiled.  I had survived my ordeal and my secret would be safe!

But it was at that moment that I realized that I was passing in front of the Tasker brothers' house.  Ben Tasker was a senior at my high school and was on the football team.  His older brother Dick worked at the gas station.  Both of them were big, mean and stupid.  And in the blink of an eye, Ben and Dick were standing on the sidewalk in front of me, blocking my way.  "Well look at this," said Dick.  "Looks like we caught outselves a Sissy walking around our neighborhood."

"Yup," replied Ben.  "At first, I didn't believe it when the girls called us.  But here he is, on our sidewalk, just like the girls said he would."


It had all been a big set up.  I had fallen right into my sister's trap.  At that moment I heard the girls drive off, honking their horn and laughing as they left me there with these two thugs.


"Well, let's get you inside, little Sissy," said Dick as he roughly grabbed my arm and started to drag me towards the front door.  I tried to squirm free, but then Dick slapped me hard and warned me to be "a good little Sissy, or else!"  I was too terrified to resist further.


"This is going to be fun!" shouted Ben.


"I get to go first," said Dick as he shut the door behind us.

Sissy Goes Outside Part 1

I liked dressing up in my older sister's clothes and I did it whenever I was home alone.    First, I would put on one of her bras and a pair of her panties.  Next I would go to the bathroom and do my make-up and fluff up my longish hair.  Then I would go through her closet, trying on her dresses, skirts, blouses and shoes.  I even dressed up in her nightgowns and bathing suits.  I would pose in front of her full length mirror, admiring my feminine reflection.

That's exactly what I was doing when disaster struck.

I was all dolled up in my sister's make-up, underwear and a party dress.  The dress was my sister's favorite.  It had a feminine, white ruffled top, a black skirt and a wide belt that gave me a sexy shape.  I was also wearing her sexy new peep-toed pumps with really high heels.  I felt so girlish and sexy.  I was posing and admiring my reflection in her big mirror when I heard a girl's voice scream, "Oh My God!"   I spun around and saw my sister and two of her friends standing behind me. My sister's friends started laughing uncontrollably.  My sister shouted, "What the fuck are you doing in my clothes?!?"

I was too shocked to speak so one of her friends answered for me. "Your brother is a total sissy faggot!"

My sister glared at me for a minute and then said, "Don't move."  She went downstairs followed by her friends. I was so afraid and confused and ashamed that I that just stood there as she ordered.

A few minutes later the three of them returned.  "Well Sissy," she said, "I'll make you a deal.  I won't tell Mom and Dad about this -- but you have to do something for me."

"Sure," I said eagerly.  I would do anything to keep my parents from learning about this.  "What do I have to do?"

"It will be easy," my sister replied.  "All you have to do is to walk down Walnut Avenue, from Church Street to Parker Street." 

"You want me to go outside?  Dressed like this?" I exclaimed.  I had never even thought about going outside before.

"No!  Not in my favorite party dress.  We'll pick out something cute and appropriate for you to wear.  Now don't be such a Sissy," my sister said while her friends giggled.  "Walnut is a quiet street.  Now get into the bathroom so we can fix you up."

I really had no choice so I complied.  And my sister was right -- Walnut was a quiet street.  I should be able to do this.

Well, the girls teased me mercilessly as they made me  strip down to my sister's bra and panties.  They  went to work on my hair and make-up and made me look really pretty -- much better than I had ever done myself.  Then they picked an outfit for me to wear.  The girls helped me dress and then ordered me into the car.  Now I stated to get nervous and I said that I had changed my mind.

"Too late, Sissy!" my sister snarled.  "Shut up and get in the car."

I started to cry as the girls shoved me into the back seat of the car.

A Sissy's Place is in the Home

Poor little Sissy Tina.  Three years ago I sold Sissy Tina to a Master who firmly believes that a Sissy's place is in the home.  So much so that Sissy Tina hasn't been allowed out of his Master's home since the day he was purchased.  In fact, Sissy Tina doesn't even own any real clothes -- just sexy lingerie to wear around the house!

And doesn't Sissy Tina look absolutely delicious in this lovely white ensemble? Sissy Tina's Master has purchased literally hundreds of exquisite lingerie sets for his Sissy.  White ones, pink ones, black ones.  Little baby doll nighties, heavily boned corsets, sweet little teddies.  And maribou slippers with four inch heels -- in colors to match every outfit. 

Sissy Tina doesn't even have any clothes to wear when his Master invites company over.  Sissy Tina has to parade around in his lacy and frilly undies while everyone ogles -- and fondles -- his very exposed and marvelously feminized body.  Poor Sissy Tina wants to die of shame.

And Sissy Tina's Master enjoys having his silky little Sissy perched on his lap.  Poor Sissy Tina has to just sit there obediently and perfectly still as his Master runs his big rough hands all over his Sissy's soft skin.  And Master also enjoys the fact that his little Sissy is also dressed for sex whenever Master is in the mood!

If you had a Sissy of your own as pretty as Sissy Tina, would you allow him to wear clothes in your house?  Of course not!

Cornered Sissy

It was time for the evening fun to begin. After enjoying the dinner that his Sissy had prepared, Master Night ordered his Sissy to stand beside him.

"Strip," he ordered.  Sissy Dawn knew better than to resist his Master's instructions. But he hesitated for just a moment thinking about the "game" his Master would want to play as soon as his soft white skin was exposed.

Master Night would tolerate no such hesitation. He instantly slapped Sissy Dawn's bottom with all his strength, nearly knocking his feminized boy toy to the ground. "I said strip. NOW!"

"Yes, Master, Sir," the Sissy quickly answered, practically ripping his pretty little dress from his body. "Sorry, Sir.  I apologize for being so slow."

Sissy Dawn's frilly sundress now lay on the floor. The Sissy stood before his Master wearing only his sexy bra and panties. His enormous breasts were practically spilling from his strapless bra.  Master admired the Sissy that had been sculpted exactly to his specifications.  He enjoyed knowing how humiliating it was for his ultra feminized Sissy to be on display wearing nothing but his beautiful, lacy lingerie.

"That's more like it," Master Night said, as his hand began the rub his Sissy's pantied bottom.  "Do you like it when I do this?" Master Night asked.

"Oh yes, Master," the Sissy replied breathlessly, just as he had been taught. "I love it when you fondle me."

"That's because your such a slut," Master answered with a sneer. "You disgust me. Did you know that, Sissy?"

"Yes sir," Sissy Dawn replied. "I do not deserve the privilege of being owned by you."

Master smiled at his Sissy's total submission. Leering at his nearly naked Sissy, Master Night said, "Let's play a game of hide-and-seek." Sissy Dawn's heart started racing with fear. "Ready, set, GO!"  Master shouted.

And with that, Sissy Dawn started racing through the mansion, his big boobs bouncing as he tried to run in his high heeled sandals.

"Ready or not, here I come!" Master shouted, just a few seconds later when the Sissy had only reached the foyer. Sissy Dawn sprinted as fast as his sissified body would let him. He ran through the formal dining room and through butler's pantry. He made it to the study and was about to run up the back staircase when Master caught up with him.

"Sissy, I'm disappointed. That was too easy. I don't think you were even trying," Master said.  "Oh well, I won again!"  And with that, Master pulled the taser from his pocket.

"Please Master, no! Not the taser!" Sissy Dawn pleaded as he backed into a corner of the room, desperate to get even a few inches away from his insane Master and his taser.

"Now Sissy, you know the rules," Master replied sternly.  "If I can find you in less than ten minutes, I get to give you a stingie."

"Please Master!  NO!  It's not fair..."

Master had heard enough. He jammed the taser into his Sissy's crotch and gave his Sissy a long, nasty shock.  Sissy Dawn screamed and collapsed on the floor. And because he was now angry with his Sissy, Master gave another shock to each of Sissy Dawn's giant tits.

Sissy Dawn writhed on the floor from pain. Master took advantage of this to kick his nearly naked Sissy.  Sissy Dawn sobbed uncontrollably as he lay helplessly on the floor.

"The rules are the rules, Sissy. Dont you forget that!"  Master said as he unzipped his pants.  "Now let's have some more fun..."

Sissy's Anniversary Surprise

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Sissy's Sexy New Lingerie

 "Oh Sissy Belinda!  Come here!" my Wife shouted from her bedroom, ringing a bell that could be heard throughout the house.  I had been dreading this moment all night. 

Four hours ago, before going out on a date with her new boyfriend, my Wife handed me a box from a fancy lingerie shop downtown.  "There is a very pretty new bra and panty set in the box.  I want you to be wearing this and looking your sexiest when I get home.  And I want you wearing this pink bow in your hair.  And this lacey glove.  Do you understand?"

"Yes, Ma'am," I meekly replied.  And while my Wife was out on her date, I dressed in the outfit as ordered.  I carefully tucked my pathetic little cockette away to ensure there would be no unsightly bulges.  I worked very hard to make my hair and make-up look sexy too.

My wife had returned home about an hour ago and was entertaining her new lover in the Master bedroom.  I had been waiting in silence in the laundry room, which was now also my bedroom.   And now I had been summoned.

I raced up the stairs to my Wife's master bedroom because my Wife hates to be kept waiting.  There I found my Wife and her lover sitting in bed naked, breathless from having just made love.

"You see, Charles, you didn't believe me.  This is my Sissy husband.  I call him Belinda now," my Wife explained to her muscular and handsome lover.

"No way!" he exclaimed in disbelief.  "That hot chick was your husband?"

"Well, unfortunately, technically he still is my husband, but you neededn't worry about that."  Then to me she said, "Well don't just stand there, Sissy Belinda.  Show us what you got.   Give us some sexy poses and show us what a pretty and pathetic little Sissy you've become.  I want to take some more photos of you."

As instructed, I struck several provocative poses, while my wife snapped away with her camera.  I could see the sheets cover Charles' lap begin to stir as I did my thing.  Obviously he was enjoying my performance and getting excited.

"And Charles, Sissy Belinda doesn't just look and act like a girl.   Oh no, he also sucks cock like a girl.  Isn't that true Sissy?"

"Yes Ma'am," I replied shamefully.  This was not the first time that my Wife had brought a lover home and forced me to "entertain" him.

"Well then, don't just stand there. Get over here and wrap your lips around this," she commanded as she threw back the sheets.  I gasped with when I saw her lover's monstrous cock.  My wife roared wife laughter seeing the shock on my face.  "Get busy Sissy!"

Sissy's First Date

The girls at the salon had great fun with me today, spending hours on my hair and make-up.  They even gave me a bikini wax.  All afternoon they chattered excitedly about my big date tonight -- my first date with a man!  I am absolutely terrified and disgusted by the whole idea.


After discovering my crossdressing secret two years ago, my wife has been forcing me to become more feminine and subservient.  She has used diet, hormones and coercion to transform me from a closeted crossdresser to a pathetic, full-time sissy under the complete control of my wife. 


My wife no longer accepts me as her husband and has recently started entertaining her new lovers in our home,  And now she has told me that I also need to have male lovers! 


That is why I have been all dolled up for my big date tonight.  My wife arranged everything.  She picked the man ("Very tall, very muscular -- a real alpha male!" she said), picked the rerstaurant and ever reserved a hotel room for afterwards.  I have been instructed to please him in every way and that I may not come home until morning.  Also -- I will be in big trouble if he doesn't ask for a second date.


My wife insisted on snapping photos while I got dressed.  She had me perch on the chair and pose for some sexy photos in just my underwear.  I forced myself to smile so as not to anger her.  She made it very clear to me that she expected me to be enthusiastic and charming at all times -- regardless of how I actually felt. 

"Enough prancing around in your sexy undies," my wife siad.  "Let's get you into that pretty dress I bought for you.  You are going to look so pretty tonight!  Your handsome date will be simply delighted!"

Just as my wife finished zipping up my form fitting dress, the doorbell rang.  "Oh, he's here!" my wife exclaimed.  I felt faint and wanted to run and hide -- but I had no where to go.  My wife handed me a cute clutch purse and pushed me towards the door.  "Now, be a good little sissy and do everything I taught you.  And maybe next week we can go on a double date with both of our boyfriends.  See you in the morning!" 

A Stepmother's Sissy

After my father's death, my evil stepmother sent me away to feminization clinic in Brazil.  There, over the course of 18 months, I was forced to undergo a total transformation from a normal teenage boy to sexy submissive sissy.  The feminization clinic was part hospital, part bizarre finishing school and part hellish concentration camp.


I was awakened extra early today and taken to the salon, where over the course of several hours my hair and make-up were done in a very glamorous style.  Then I was brought back to the Administration building where my trainers dressed me in this very fancy lingreie. 

As several bracelets were slipped on my wrist, I heard my stepmother's voice coming from the next room.  I had not seen her since she had imprisoned me in the clinic a year and a half ago.

"That's right, Sissy, your Stepmommy is here.  She can't wait to see what we've done to you!  Time for your big debut," one of my trainers said with a cruel smile.

"Well hurry up and get out here!" my stepmother commanded from the next room.  "Don't be shy -- no reason for my new stepdaughter to be bashful in front of her stepmother," she cackled.

I was frozen with fear, horrified by the idea of parading aroung in front of her in my bra and panties, my complete sissification on full display.

"Get out there and behave yourself -- or else," the trainer threatened, brandishing the cattle prod he always carried. 

I swallowed hard and braced myself for the humiliation that awaited me.  I nervously parted the beaded curtain that hung in the doorway and made my entrance to the other room.  There was my horrible stepmother, seated on a sofa snuggled up close to a man I had never seen before.

My stepmother squealed with delight when she saw me.  "Oh my Gawd!" she exclaimed.  "It's even better than I could have dreamed.  Look at you, you pathetic sissy faggot.  What a little sissy slut you must be, prancing around in your girly undies for everyone to see."

"Isn't this wonderful, Roberto," my stepmother said to the man next to her,  "Now that my loser stepson is gone forever, I will inherit all of his father's millions.  We are rich, Roberto!" she said giving him a big hug.

"Well, time to go home Sissy.  Today you start you new life as my personal handmaiden, my own fulltime servant tending to my every need.  Won't that be wonderful?" she teased.

"We will dress her and bring her to your limo," the trainer helpfully offered.

"Oh heavens no," my stepmother replied.  "She doesn't need clothes.  She looks so lovely just the way she is.  Come along Sissy, get in the car.  A new life awaits!"