My Sissy Neighbor -- Part 8: Transition to New Life

Mom and I did our best to help Anita settle down after his horrible ordeal.  Mom wanted him to go to the police, but I knew he wouldn't agree to that.

"Well, at least you are NEVER going back to that awful club."

"But I have to!" Anita wailed.  "I need the job if I ever want to move out of my house!  I can't stay there anymore.  Things are so bad with all the yelling and drinking and..." Anita took a deep breath and continued.  "I think my dad is beginning to figure out that I'm not exactly the man he thinks I should be.  And if he ever figures out about Anita, hell kill me.  I mean it!"

He continued, "I've been saving up my money so I can move out of the house.  Maybe I will move to California."

Mom and I stared at each other for a moment and then said -- in unison, "Just move in with us!"

Anita looked confused for a moment and then said, "But I can't move in here.  I don't want my parents to know I live just next door.  That won't fix anything."

Mom spelled it out for him.  "Move in with us as Anita.  Let your parents think that Andy has gone to California or Timbuktu or where ever.  Graduation is in just a few weeks.  Stick it out until then.  Then say 'so long' to your folks, pack up your car and start the long drive -- to the house next door!"  Mom seemed very pleased with her solution.                                                                                                         "But, my parents will recognize my car," Anita protested."Sell it.  Get a new one with all the money you saved up." Mom replied.                                                                                                                                                      "But what would I do all day as Anita?  I've never lived full time as Anita before," he noted.

"Well..." mother replied, "I could use help with my real estate business,  Things are really booming.  And my own daughter has no interest in real estate." She was referring to me, of course -- and it was true. She continued, "Besides, she's heading off to college in just a couple of months."                                                                                            We talked about it for a long time into the evening and Anita finally gave in to mom's proposal.  A lot of things happened over the next few weeks. Let me fill you in:

Andy graduated and told his shitty parents that he was moving out.  He dropped his few belongings at our house and then traded in his awful car for a really nice used Audi A4 sedan.  It was definitely the car Anita belonged in.                                                                                                     Anita started helping mom out with her business, handling some simple phone calls, making appointments, sometimes signing-in people to open houses.  Here are some photos of Anita that mom took during Anita's first few days showing houses.  Mom noticed right away that Anita was a natural at this.  Anita can talk to anyone -- a skill he honed at the club, no doubt.  And of course, being gorgeous didn't hurt either -- especially with the male customers.  But mom noticed even the female clients seemed intrigued by and drawn to him.  Mom started giving Anita more and more responsibility.  And by the time I went off to college in late August, Anita was studying for his realtor's license.

And for me, the best part of the summer was having Anita living with us full-time!  We kept it quiet from mom, but we found lots of time for our little make-out and hand-job sessions. One day Anita asked me to show him how to eat pussy.  I was more than happy to let him practice on me!  And he was a natural!  I have never cum so hard or so many times in my life. It was such a turn on to see that beautiful blonde hair of his between my thighs; feeling those full, lip-stick coated lips and his very talented tongue go to town on my pussy.  It was the best summer of my life!                                                                                                                   "Anita," mom said one evening before they sat down to dinner.  "We need to talk."  Anita was concerned by mom's unusually serious tone.  "Anita, you are doing a great job helping me with the real estate business.  I am so impressed by how mature and professional you are.  And I know you are going to ace the real estate license exam."   Mom took a deep breath.  "But you can't be a realtor and sell real estate under a false name.  You have to use a real name -- on your license, on your business cards, everything."                                                                                                                           Anita turned pale.  His dreamy new life as beautiful Anita, as a young professional woman starting out on a real career, seemed to have crashed.  "But I can't live like this and call myself Andrew for goodness sake."                                                                                                          

"Of course not," replied mom. "So maybe this is the right time for you to say good-bye to Andrew and become Anita.  For real.  Legally, and if you want, surgically." Oddly, this suggestion came as a surprise to Anita.  Anita sat in silence as he thought about what mom had suggested.  And then mom added brightly, "And then you can be my niece for real!"

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.

A Boyfriend for my Sissy Husband -- part 2

A week passed and it was time for Danielle's second date with his new "boyfriend," Martin.  Of course, Martin wasn't really Danielle's boyfriend - he was a man I picked to construct a wild psycho-drama for my sissy.

Danielle was all giggly and nervous before Martin arrived to pick him up.  Unlike last week when Danielle was terrified of being out with a man, tonight I could tell he was excited and looking forward to it.  Something deeply feminine and girly had been awakened by his first date.  It was as if Danielle was being flooded all at once by the emotions of a 15 year old girl!

Danielle had begged me to take him shopping for a new dress to wear.  This was going even better than I could have dreamed!  Danielle explained that Martin wanted to take him to The Windsor for their second date.  The Windsor is a very exclusive and very expensive restaurant and after hours club with wonderful food and live music and dancing.  Danielle was all aflutter with the idea of being asked out on a date there.  I agreed to take Danielle shopping and we bought a very elegant purple dress for him to wear.

When the big day arrive, once again Danielle spent most of the afternoon at the beauty parlor getting all prettied for his date.  The girls at the salon made him describe every minute of his prior date.  They told Danielle how lucky he was to have such a handsome and charming man pursuing him and taking him out to really fancy places. Instead of becoming anxious by their chatter like he was last week, this time Danielle was flattered and encouraged by it.

Martin picked up Danielle and took him away for the evening. Here are some photos of the two of them on the grand staircase heading downstairs to the club after they finished with their dinner. It was another dreamy dinner date for Danielle -- his girly feelings completely overwhelming his natural heterosexual tendencies. 

Danielle was much more relaxed than he was on their first date.  And Martin was much more flirtatious.  After the wining and dining, the lovebirds moved to the dance floor, where Martin expertly led Danielle as the combo played a variety of slow, romantic songs.  Danielle felt so safe in Martin's strong arms.  Danielle felt like he was floating on air, twirling and swaying in his lovely purple dress and 4 inch sandals.

When they couldn't dance anymore, Martin navigated them both to a sofa where they sat.  Martin said, "Danielle, I know I only just met you, but I want you to know that I already have very strong feelings for you.  Danielle, I'm falling in love with you."

Danielle's heart must have almost stopped beating when he heard this. Before Danielle could open his mouth, Martin took out a small wrapped gift from his pocket.  "Here, Danielle, this is for you."  Danielle nervously accepted the small box from Martin and opened it. Inside was a beautiful heart-shaped pendant covered with about a dozen diamonds.

"Oh my!  It's lovely!  I...I don't know what to say.  This is all so unexpected!" Danielle managed to sputter.

"I'm sure it is," Martin said calmly as he helped Danielle put the necklace on.  "You don't have to say anything.  But I do want to see you again.  And soon.  And for longer. And for more."  Danielle looked confused so Martin elaborated. "Next Saturday, let's spend the whole day together. Here's my idea.  We can drive over to the lake and get room for the day at the Inn on the Pier.  We can get to know each other better, if you know what I mean."  Now Danielle knew exactly what Martin meant.  Danielle knew this was not something that he should agree to but he couldn't help himself.

"Okay," Danielle said.  "But I can't tell my...spouse.  I know that meeting you was all her idea but I don't think she would approve of me checking into a fancy hotel with you."

"Not a problem," Martin responded.  "All of this can be our little secret.  You can tell your...spouse...that I have planned a full day of activities together downtown, we'll go to the museum, then lunch, then a matinee...I will pick you up at 9:00 and have you home by 6:00.  And no one will ever suspect what we're up to."

"You are a devil, aren't you, Martin Rittenhouse?" Danielle replied with a wide grin, barely able to contain his delight that this handsome man was pursuing him as if he were the most beautiful woman on the planet.

There was more kissing and groping in the car before returning Danielle home.  I again was waiting in the living room.  Danielle gave me a report on his evening, delighted in sharing details of the dinner, the dancing, the music.  But he did exclude a number of details.  He said nothing about the necklace he received (he must of taken it off just before coming inside), nothing about Martin's profession of love for him, and nothing about their sneaky plan to screw around in a hotel next Saturday.

Of course, Martin kept no secrets from me.  And I fully expected my pathetic sissy husband to mislead me about what was really going on between him and Martin. Danielle didn't know it, but he was quickly digging himself into a hole from which he might never emerge. 

Uncle Jim Gets a Sissy

After my parents died in a car accident, I was sent to live with my Uncle Jim.  I had never really liked Uncle Jim.  I had always thought that he was sort of rough and maybe a little strange. I was about to discover how right I was.

Uncle Jim lived alone in a big, old farmhouse far out in the country.  His wife, Darla, had walked out on him many years ago.

No sooner had I brought my suitcase into the house the Uncle Jim announced, "You won't be needing your old clothes.  I got plenty of better clothes for you to wear.  You see, when Darla ran out on me, she left all her old things.  And so now you can take Darla's place.  So why don't you go upstairs and put on one of Darla's pretty dresses while I go out back and burn your old clothes."

I began to protest but Uncle Jim started beating me.  Hard.  I was no match for him; I was small and weak and he was huge and strong.  It didn't take long for him to wrestle my suitcase away from me and to drag me up the stairs to Darla's old closet. He picked out a dress and threw it on the bed.  "Now get changed like I told you to!" he shouted.  "There's underwear and make-up in those drawers and there are pretty shoes in the closet.  Now hurry up, get dressed and get your ass downstairs."  He hit me again before he slammed the door behind him and stomped down the stairs.

I was paralyzed.  I started crying as I sat on the bed, looking at the flowery dress that was lying there. Then I smelled smoke.  I looked out the window and true to his threat, Uncle Jim was burning my clothes in the back yard.  I knew I was in big trouble and that I had better start cooperating or something really bad would happen to me.  I put on one of Darla's bras, a pair of her panties, the dress and some shoes.  I put on some red, red lipstick and some rouge on my cheeks.  I took a deep breath and headed down the stairs to where Uncle Jim would be waiting.

That was nearly a year ago.  I have been living and dressing as Darla all day, everyday, since I arrived.  My hair has grown longer and I am now better at doing my make-up and walking in high heels. Uncle Jim calls me Darla and expects me to do everything a good housewife does. I cook and serve three meals a day for him. I scrub the floors and wash the windows. I vacuum and I dust. I do Uncle Jim's laundry. My chores are endless. I hate my life. As I do my chores, hour after hour, day after day, all I can think about is how wonderful and free my life used to be, when I was a normal boy. But that life is behind me now. I am the Sissy housewife/slave of a demented monster.

Uncle Jim gets very mad at me if he catches me daydreaming or not doing my chores vigorously enough.  And he gets furious if he thinks I don't look pretty enough or if I don't sound and walk and laugh enough like Darla did. And when I disappoint him he throws me over his knee and spanks me brutally.

And after I have cleaned the the house from top to bottom and after I have put away the dinner dishes, I have to put on one of Darla's nightgowns and take care of my "husband's" sexual needs.   No matter how awful my household chores are, nothing is as awful as having Uncle Jim's giant naked body on top of me, kissing me and feeling me up all over. But worst of all is when I have to do the things that he says Darla refused to do. I have to put Uncle Jim's cock in my mouth until he gets ready to cum. Sometimes he likes to cum in my mouth and make me swallow it.  But mostly, he likes to pull It out just before he cums and shoots it all over my face. After I clean us both up, Uncle Jim usually climbs on top of me again and falls asleep. That's when I usually start crying until I fall asleep, getting a little rest until my life as a sissy housewife/slave starts again in the morning.  

The Sissy Debutante Ball

Mother had been dressing her son Jimmy up as "Ginger" for years.  At first Jimmy had resisted but his mother was very strong-willed and Jimmy was weak.  Over time, Jimmy stopped fighting his feminization and accepted what his mother was doing to him.

"I had always wanted to have a daughter," Mother told him a million times. "But unfortunately you were born a boy.  But just because you were born a boy doesn't mean I can't make you into my daughter." 

So ever since he was a little boy, Jimmy spent most afternoons -- and every weekend -- dressed as Ginger. And while wearing his pretty party dresses and nightgowns, Ginger and his Mother would spend countless hours doing things that mothers and daughters do.  Mother taught Ginger how to do his make-up and his hair and his nails.  They would do chores around the house like cooking and cleaning and ironing.  At night they often watch chick-flicks together while wearing their pretty night gowns.

So Ginger was brought up to be a perfect little Sissy.  But Ginger was growing up and tonight they would celebrate the lovely Sissy lady that Ginger had become.  Tonight was the Sissy Debutante Ball!

Tonight, nearly fifty Sissies, aged 18 to 20, and their Mothers would celebrate the long and sometimes difficult journey of raising a son to be a Sissy.  Mothers from all over the country brought their lovely Sissy darlings to this lavish affair at a posh hotel in New York City.  

Ginger and his Mother looked heavenly in their coordinated, custom-made outfits.  Mother wore a tailored suit of beautiful golden silk jacquard. Ginger wore a long gown -- made of the same gold silk jacquard as her mother.  Ginger's gown made him look sweet and sexy at the same time. Ginger and his mother had spent most of the aternoon at the beauty salon. Their hair and make-up were perfect.

Even though he looked very beautiful, Sissy Ginger was so nervous as he and his mother rode the evevator down from their hotel room to the ballroom below.  Sissy Ginger didn't know what to expect. 


They made their entrance when the Master of Ceremonies announced their names over the speaker: "Presenting Sissy Ginger and his Mother, Lady Annette!"  The other guests clapped as Ginger and his Mother entered the room.  Ginger was quite stunned by the applause and by the flashes of cameras capturing his big entrance. They found their seats, Lady Annette at one of the Mothers' tables and Ginger at one of the Sissies' tables.

As Ginger introduced himself to the other Sissies, he noticed there were several other tables in the ballroom that were occupied by men. Ginger asked one of the other Sissies who the men were.

"Don't you know?" answered one the other Sissies with surprise.  "After dinner is finished and the announcements are done, the Mothers will all leave and go to another room for the rest of the evening.  That's when the men are free to talk to us and dance with us and..."

"And WHAT?" Ginger asked, somewhat panicked.

"Well, they can ask us to come up to their rooms with them, of course.  And you are not allowed to refuse.  That is all part of the Sissy Debutante experience.  Tonight we become real Sissy Ladies with the Gentlemen that pick us.  Are you saying that your Mother never explained this to you?"
Poor Sissy Ginger.  He nearly fainted when he heard this.  Of course Mother had never told him about all this.  He would have been too terrified to even come here tonight.  

Tears started to well up in poor Ginger's eyes.  "Here, take this," said one Sissy offering Ginger a Xanax and a glass of champagne.  "Just relax and remember that this is what your Mother wants for you.  You need to be brave and do what your Mother expects you to do."

The other Sissy was right, thought Ginger as he downed the pill and the champagne in a single gulp.  "May I have some more champagne?" asked Ginger trying to prepare himself for the frightening evening ahead.  "A lot more."

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.

My Perfect Sissy Housewife

Two years ago, my husband finally admitted to me that he was a crossdresser.  Of course, I had figured that out years earlier -- but I just waited patiently for him to finally admit it to me.  And during those years of waiting, I had been thinking long and hard about how I was going to deal with my husband's crossdressing.

So when he finally said something, I let loose with my well prepared list of demands.  I started by telling him that, from now on, I would be wearing the pants in the family.  My career was really taking off and his was going nowhere.  I decided that I would like to have a sweet little housewife taking care of me and my home full-time.  That would be his job from now on.

And he would not be just any housewife.  Oh no.  He would take the role of a traditional, obedient, submissive homemaker from decades past.  He would live and dress the part.  Every detail would have to be perfect and to my liking -- from his pretty hair-do, to his pleated skirt, to the sheer hostess apron tied aroung his trim little waist to the smile on his pink, glossy lips as he went about his chores.  His endless chores!

At first, he tried to protest but he was simply too much of a sissy to fight me.  I started implementing our "lifestyle changes" right then and there.  I made him hand over his license, credit cards and passport -- and watch as I ran them through the shredder.  Within a week, I had him empty every closet and drawer of his old clothes and reminders of his old life, which I refilled with his new homemaker fashions.  Within a month, we had moved to a new town to make it easier for us to restart our life as a high powered lady executive and her devoted, old fashioned housewife and partner.

That was two years ago and my husband is now been completely transformed, in body and mind, into the gentle, doting housewife I wanted.  He has become completely proficient at doing all his housewifey chores, from cooking, to cleaning,to giving me footrubs, to preparing my martini when I get home in the evening.  Here he is doing the laundry.  He takes such pride in being the perfect housewife.  Look at how happy he is knowing that he is pleasing me.

I have recently started dating one of the senior partners at my law firm.  He will be coming over to my house tonight for a romantic dinner that my hubby-housewife will prepare and serve.  If the date goes well, hopefully my sissy will be serving us breakfast in bed as well.






'

Sissy Gets Ready to go Out

Two months ago, my little sister had caught me dressed up in mom's clothes and make-up when she came home early one afternoon.  She said that she would tell mom and dad -- unless I did exactly what she said from now on.  I guess I had always been a bully to my little sister and now was payback time.

Since then, we've been playing "dress up" almost every night.  After dinner, we run up to her room where she makes me practice doing my make-up and styling the wig she made me buy.  She makes practice walking in high heels and sounding like a girl when I talk.

She told all her friends about what a sissy I was -- and how I was really cute when dressed up like a girl.  Tonight, my sister told me, was going to be my "coming out" party.  She was going to take me, along with three of her friends, to a fancy club downtown where they never check IDs of cute girls who want to go in.  I'm the only one old enough to have a license, so I have to drive.

Mom and dad went out early to go to a party so we spent most of the afternoon getting ready.  My sister picked out my outfit for the evening from mom's closet -- a fancy gold and white Lily Pulitzer dress and a pair of strappy high heels.  She helped me get my wig and make-up just right.

"Hmmm," she said with a smile while looking me over when we were done.  "You know, Michael, you really do look like a pretty girl.  I don't think any of the guys at the club would ever guess that you're really a boy when they start flirting with you.  Just be careful when they start feeling you up."

When she said that, I broke down into tears, panic suddenly overcoming me.  "Please don't make me do this!  PLEASE!"

"Oh for God sake STOP CRYING!," my sister yelled.  "You're ruining your make-up!  You are such a big sissy!  Get it together and fix your make-up before the girls get here!  NOW HURRY!"  She slammed the door and went downstairs.

I stared at my reflection in the mirror.  My sister was right -- I did look like a pretty girl.  And she was also right about me being a big sissy. I knew I had to obey my sister or she would tell mom and dad.  As I started redoing my make-up, I tried to imagine what it was going to be like, being in a fancy nightclub in a pretty backless dress, sexy stilettos and glamorous make-up, knowing that men would be trying to talk to me and buy me drinks and...other things.

"Michael!  I mean Michelle!" my sister yelled from downstairs.  "Hurry up!  The girls are here!"

I dried my tears and fought to calm myself down.  I fixed my mascara and finished putting on my bright red lipstick.  I grabbed my little clutch purse and headed down the stairs.

When my sister's friends saw me, they screamed with delight.  They all told me how pretty and sexy I looked.  They said that all the guys would be drooling all over me tonight.  I enjoyed hearing the girls say that I was pretty -- but talking about the men at the club made me feel  sort of sick to my stomach.

One of the girls said, "And when you're giving some guy a blow job tonight, be sure to swallow every drop.  You don't want to get any stains on  your mother's pretty dress."

The girls howled with laughter at that.  I almost started to cry again.

"Time to go, Michelle," my sister said.

Mother and her Sissy Son Plan a Trip

"But mother," Eric protested.  "I don't want to dress up like a girl!"

"Oh, not this again," mother replied with a sigh.  "Stop your fussing and let me see how you look in the blue dress.  Hmmmm.  That's very cute on you.  The skirt has a pretty flare.  Now hold the skirt out like you're going to curtsey."

"Marvelous!" she exclaimed as she took another photo.  "That dress will be perfect for when we go shopping in New York City next weekend."

"But mother, PLEASE!" he said.  "Why do I have to be dressed as a girl when we go to New York?"

"As I've told you a million times," mother replied impatiently, "You are going dressed as a girl because you are much too pretty to be a boy!  And besides, a mother/daughter trip will be such fun!"

Ever since Eric had been a little boy, his mother enjoyed playing dress-up games with him.  He didn't mind too much.  In fact he even enjoyed it.  But recently, mother had been insisting that Eric spend more and more time dressed up as "Erica". 

"Now try on the black one with the spaghetti straps," mother instructed.  Eric did as he was told.  He didn't have the spine to stand up to her.  And deep inside, a small part of him enjoyed being feminine.  But things really were beginning to go too far, he thought.

He slipped on the little black dress and his mother zipped him up.  "Oh my!" she squealed.  "That is just ADORABLE on you.  Turn around and let me see.  Oh yes.  You are simply lovely in that! That will work for going out to nightclubs.  You will certainly get a lot of attention looking like that!" she teased.  Eric hated it when she said things like that.

Eric started getting angry.  "And I hate wearing my hair like this!  I look so...girlish all the time.  All of the boys at school make fun of me.  And they can tell that I shave my legs when I go to gym class."

"Oh don't pay any attention to those silly boys," mother said dismissively.  "Sweetie, that's the way teenage boys get when they see a pretty girl and start getting...excited."

"MOTHER!" Eric shrieked.  "I'm not a pretty girl!"

"Hush now," mother replied calmly.  "Don't be silly.  You are very VERY pretty!  Now try on the long sleeve wrap dress."

Again, Eric complied.  He was too much of a sissy to fight back. 

"Oh my! Oh my!" mother said.  "You look so sophisticated in that dress."  She had Eric put on a pair of black lacy stockings and she slipped a necklace around Eric's neck before taking some more photos.  "That dress will be perfect when we go out to dinner.  I made reservations at some of the best restaurants in New York while we're there."

Finally mother had Eric try on vintage black dress with sheer sleeves a feathery trim around the neckline.  It was a beautiful, exquisitely feminine dress.  Mother took several photos and purred, "Oh Erica, darling.  That dress is just heavenly on you.  You look so beautiful."  At that moment, mother decided that Eric would wear this dress to his interview at the New York Sissy Academy.  Mother desperately wanted Eric to attend their famous one-year "Total Conversion" program so she could at last have the daughter she always wanted.  Eric didn't know anything about this part of the weekend plans.  But Mother was so confident that he would be accepted to the Sissy Academy that she had only purchased a one-way plane ticket for her Sissy son.

My Sissy in the Tub

I have always loved my husband very much.  He has always been kind and gentle and generous with me. 

But after his second heart attack, I insisted that he quit his high pressure job and make some...lifestyle changes. 

That was three years ago.   Now, with my guidance, my husband who was once a powerful executive has been transformed into the most delightful and feminine Sissy gurlfriend. 

Here we are in the tub enjoying our time together.  His pale skin is soft and smooth and so beautiful.  His hair has grown long and is now a lovely shade of red.  And his breasts!  They are magnificent!  I simply can not resist playing with them. 

And our love life has never been better.  Of course his little tiny cock can't even get hard anymore.  But my husband can spend hours with his face between my legs bringing me orgasm after orgasm with his talented little tongue.  When that isn't enough for me, I let him fuck me with a strap-on.

And when it's his turn for a little pleasure, I wear the strap-on, sometimes still wet with my juices, and fuck his little sissy pussy.

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.

New Sissies at the Beach

Last week I took my two newest Sissies for a day of fun at the beach.  It was a holiday weekend, so the beach was very crowded and my Sissies attracted a lot of attention!

These two fell into my clutches just a few weeks ago.  They are just at the very beginning of their transformations.  Their boyish haircuts are just starting to grow into more sissyish styles -- although I already dyed their hair to a prettier, more feminine color.  They are still very confused and frightened by their captivity and forced transformations.

My newest Sissies were horrified when they saw the outfits they would be wearing.  But their protests subsided after a few whacks with my hairbrush.

And aren't they absolutely darling!?!  I just loved dressing these two up in these identical sissy bathing suits -- with the matching sissy cover-up.  The high waisted panty (with an adorable little bow!) and the training bra tops are simply devine.  And the little pink heartsare just perfect for little Sissies.

I love this photo.  The Sissy in front is about to start crying as I just ordered him to take off his cover-up and let everyone see him in his pretty Sissy bikini!

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?

Rotten Stepson becomes a Perfect Sissy

When I decided to have my stepson transformed into a feminized, obedient Sissy, I had no idea where this would lead.  Mostly I was sick of his rude behavior, his back talk and his laziness.  It was such a relief when I had him sent away for his year-long transformation.

When I first brought him home I was totally amazed by his transformation.  Physically he had been completely changed.  He was now a pretty, delicate, completely feminine little Sissy.  His hair was long and had lovely coppery highlights.  He had lost twenty or thirty pounds -- maybe more -- and was developing the sweetest little breasts.  Everything about his body and appearance was now so girlish.  But his physical transformation was nothing compared to his mental transformation.

He was now utterly and totally obedient to me.  He seemed to have no desire other than to please me. He was such a delight to have around the house.  He needed no instruction to keep the house spotlessly clean, to prepare my meals, make my bed -- everything!  I let him help me dress and undress me and even bathe and massage me. He would never speak unless spoken to.  When I would enter a room, he would stop whatever he was doing, lower his eyes to the floor, and curtsey to me.  It was marvelous.

But over time, I developed a strange attraction to my litle Sissified creation.  He was so devoted to me and took such good care of me.  I soon started to enjoy my Sissy in more...intimate ways.   I had my little Sissy joining in my bath and in my bed.  I enjoyed running my hands all over his soft little body.   I enjoyed pressing his naked body against mine, letting him play with my big boobs while I played with his tiny little titties.  And best of all, I loved feeling his sweet little mouth and tongue on my pussy.  I hadn't realized how thorough his training had been!

Who knows?  Maybe I'll get my Sissy stepson some big sexy breasts so he can be more like me.  I bet he'd like that!