Tuesday, July 22, 2014

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!





Monday, July 7, 2014

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.







Thursday, July 3, 2014

A Sissy's Mother Has a Plan -- Part 2

Mr. Robbins had never experienced a blow job like this before -- not from any of his girlfriends or from his ex-wives or even from any of the hookers who worked for him. As he looked down at the reluctant sissy he was face fucking, he felt a sense of power and excitement he had never felt before. It was electrifying to have his dick sucked by a boy that was transformed into a girly love toy just for his pleasure.

The excitement was too much for Mr. Robbins. As he started to cum, he roughly pulled Sissy Billy's head into his crotch, ramming the full length of his dick far down the sissy's throat. Mr. Robbin's orgasm was explosive. It felt as if he was pumping gallon after gallon of semen into the feminized plaything in front of him. It was the most powerful orgasm of his life!

But for poor Sissy Billy, it was not enjoyable at all.  He struggled to remain conscious throughout the ordeal as the giant cock was forced down his throat while Mr. Robbins roughly gripped the back of the sissy's pretty little head. 

As Mr. Robbins slowly removed his spent cock from Sissy Billy's mouth, he had a realization. Why should he put up Billy's mother -- that gold-digging bitch -- when he could just have her sissy son instead?  He sent a text to his "driver" who was waiting outside.  "Need U 2 take out trash."

Sissy Billy was collapsed on the floor after his brutal face fucking.  He was gagging, gasping for air and sobbing all at the same time.  Mr. Robbins kicked Sissy Billy.  "Go fix your make-up, Sissy," Mr. Robbins said. "I'm not done with you yet."

Billy had seated himself at the vanity when the "driver" -- one of Mr. Robbins' thugs -- burst into the room. Mother and Billy were shocked when this stranger, this mountain of a man, stormed into the bedroom.



"What's going on here?!  Who are you?!" Mother screeched, as she tried to cover her nearly naked body.  

"Which one?" the driver asked, ignoring Mother's question.  

"The old one," replied Mr. Robbins. And while Sissy Billy sat in open-mouthed shock, the driver overpowered Mother and held a drugged rag over her nose and mouth until she was unconconsious. The driver then threw Mother over his shoulder and carried her out to the car.   

"What's...what's happening?" Sissy Billy managed.  "What did you do to my Mother?"

"Don't worry about her.  She's just going away."  What he didn't say was that Mother would soon be lying in a New Jersey landfill.

"Well now, Billy," Mr. Robbins continued. "It looks like it's going to be just you and me from now on. You're going to move into my house and you're going to be my full time Sissy whore.  Doesn't that sound like fun?" he added with a snear. 

"Maybe I'll give you some great big boobs.  Yeah, I like that idea.  And maybe I'll cut off your dick."  Mr. Robbins' own dick was starting to get hard again.  Roughly, he grabbed the sissy and bent him over the back of a love seat, positioning the sissy's little bottom up in the air. "Time to lose your sissy cheery!" Mr. Robbins said as he drove his big dick into Billy's tight little bottom.

"On, yeah! That feels great!" Mr. Robbins exclaimed.  Mr. Robbins had another explosive orgasm while tears of pain, humiliation and fear poured down Sissy Billy's face.  



Monday, June 23, 2014

A Sissy's Mother Has a Plan -- Part 1

Billy had been seated at his mother's vanity for the past two hours while she did his hair and his make-up, ensuring that Billy looked like a sweet and sexy young lady.  Heavy gold earrings hung from his recently pierced ears.  His eyebrows had been plucked into gentle arches.  His recent strict dieting had succeeded in making him very skinny and delicate looking.

He wore nothing but a darling little bra and panty outfit in the softest pink. Mother had padded the bra cups to give the appearance that Billy had little breasts.  The bra was festooned with a a large bow and long ribbon. It was a very seductive outfit.

The doorbell rang and mother exclaimed, "Oh good!  He's here!  Now don't forget ANYTHING I told you about what you are going to do tonight. Do you understand?"


Billy turned on the little vanity stool on which he had been perched.  He looked at his mother who was wearing the identical pink bra and panty set.  His anxiety was mounting by the minute.  He pleaded, "But mother, do I really have to do this? Please don't make me. Please!"

Mother was not going to tolerate even a hint of insubordination.  She needed Billy's complete and enthusiastic cooperation.  Mother stormed over to where Billy sat on the vanity stool and pointed her long, manicured finger directly in his face.  "Do NOT let me down tonight or you will regret it! I think we should both consider ourselves very fortunate that Mr. Robbins has taken such a keen interest in us.  With just a little more effort, I think he might ask me to marry him and then all our problems will be solved.  We are completely broke and things have been very hard for me ever since your lousy father ran out on us."

"But mother, please!" Billy said as tears welled up in his eyes.  "I've been good.  I let you dress me up like a girl and go out with both of you on your dates.  I even let Mr. Robbins touch me and hug me. But this is completely different. Dressed like this he is going to expect only one thing.  Sex!"

"No shit, genius," Mother harshly replied.

"And besides," Billy said through his tears. "Mr. Robbins is a bad man.  Everyone knows he's part of the mob."

That comment enraged Mother.  She slapped her sissy son hard across the face. "You take that back! Mr. Robbins is rich because of his perfectly legimate waste disposal business. Now wipe those tears away and pull yourself together." 

Mother went downstairs and let Mr. Robbins.  When she led him into the bedroom, he saw that both Mother and her sissy son were dressed in the exact same sexy outfit.  A big smile crossed his face.  "Well," Mr. Robbins said. "This is going to be an interesting evening.  Let's see what this sissy can do.  Get over here and get on your knees, sissy."

Sissy Billy did as he was ordered.  He unzipped Mr. Robbins pants and outsprang an enormous cock.  "Don't just stare at it, sissy!  Suck it!  NOW!"

Reluctantly, Billy did what Mr. Robbins wanted.  He closed his eyes and put the stiffening dick in his mouth.  Mr. Robbins firmly held the back of Sissy Billy's head as he began pumping in and out of Billy's virgin mouth.

Friday, June 6, 2014

Completing My Husband's Sissy Journey - Part 3


Tonight, Marcus, Colette and I are "staying in" for the evening.  Colette prepared a lovely dinner for the three of us.  After he had finished clearing the dishes, Colette and I went up to our bedroom to get ready for the rest of the evening.

Colette took off the pretty little black dress he had been wearing and changed into a sexy outfit I had bought for him -- a silk brochade corset in the deepest green, sheer black opera gloves, and black seamed stockings. I had him slip on his sexiest shoes -- black platforms with a 6 inch heel.  He looked so beautiful as he stood in front of the mirror to brush his hair and to freshen his red red lipstick.  I noticed with great pleasure how his diet of female hormones combined with the corset was making his bottom look so soft and round.

I could see that Colette was getting nervous about what was about to happen so I gave him a Valium to settle him down a bit.  


I changed into a lacy black negilgee.  Almost as sexy as Colette's outfit but much more comfortable.



I posed Colette on the edge of a chair and invited Marcus into the bedroom.  When he saw the two of us in our sexy black outfits I thought his eyes were going to pop out of his head.  Marcus told Colette to stand and to turn around so he could enjoy the view of sexy Colette from every angle.  "That is one fine looking sissy!" Marcus said appreciatively.




























I wrapped my arms around our handsome lover.  "Well, Marcus, where do you want to begin.  Would you like us to suck your dick together?" I asked.  "Or maybe you'd like to fuck me while Colette tongues you asshole?"

"Nah," he replied.  "The sissy can wait.  I just want to have sex with you for a while."

"OK, darling.  Whatever you want.  Colette, sweetie, please go wait in ths closet until Marcus and I are done," I instructed. The combination of the wine from dinner and the Valium were having an effect on Colette. Obediently, he walked into the closet as he had done on other occassions when Marcus and I needed some alone time.  I closed the closet door and Marcus and I made passionate (and very loud!) love while Colette listened and waited in the closet. 

After Marcus had fully satisfied -- and exhausted -- me, he called out, "Sissy!  Get in here!"  Colette emerged from the closet.  "Get on the bed," Marcus instructed.



"Oh!" I exclaimed.  "He looks so pretty.  Let me take some photos before you two have sex!" I said.  I grabbed my camera and had Colette assume a variety of sexy photos on the bed.  Marcus was clearly getting turned on watching this, his huge cock already starting to get hard again.

I kept taking photos as Marcus used poor little Colette for his enjoyment, first with Colette's mouth and then with his "sissy pussy."  I have a whole collection of Colette's "action photos" posted on the web.

When Marcus was finally done cumming in my sweet little Colette, he told Colette to go sleep in the guest room so he could spend the rest of the night with me alone.  As Colette was about to leave the bedroom I said, "Colette, aren't you forgetting something?"

"Oh yes, of course," he replied. "Thank you for fucking me Mr. Marcus.  And thank you for fucking and pleasuring my wife in ways I never could."

"You're welcome, sissy," Marcus replied.  "Now get out."  And with that, Colette retreated to the little guest room for the night, a little unsteady in his high heels on account of the wine, the Valium and the serious fucking he had just had endured.







Tuesday, May 27, 2014

Completing my Husband's Sissy Journey -- Part 2

I enjoy having my husband, Colette, as my own, private lesbian lover and slave during the week.  But when the weekend comes, I'm ready to get out and really have some fun.  You see, I now have a boyfriend.  And so does my husband!  

When I first told Colette that I had taken a new male lover, he was very upset.  I let him cry for a few minutes but then ordered him to stop his blubbering.  Having a lover is what I wanted and Colette would just have to deal with it.  When he wouldn't quit sobbing I slapped him a few times until he stopped.


The very next night I invited Marcus, my lover, over to our house to spend  the evening with Colette and me.  I made Colette dress up and look his best before meeting Marcus. Here's a picture of Colette putting on his bra as we both got dressed for the evening.  Colette served us drinks and hors d'oeuvres that he had prepared.  He looked so pretty!  I know he was upset watching Marcus and me making out on the couch right in front of him.  But Colette behaved himself and worked hard to make me proud.


But that was just the beginning.  What Colette didn't know then was that I wanted Colette to share Marcus with me!  Marcus would become Colette's handsome lover too!



When I explained all this to poor little Colette, I thought he was going to explode!  He cried and cried.  He begged me not to do this.  But I had made up my mind.

So now, every Friday and Saturday night, Marcus takes his two beautiful "girlfriends" out on the town.  We go to bars, restaurants, dancing.  We even go on vacation together.  I bought Colette lots of pretty new clothes so he can look his best when we are out on our date nights with Marcus.  Here's a pretty pink dress that I think looks very nice on him.

At first it was very difficult for Colette to participate in our special "double dates."  But he cooperates because it is what I want.  














Tonight, Marcus is going to take us to dinner at the fanciest French restaurant in town.  We are celebrating our one year anniversary as a couple (plus one!)  And then after dinner we are going to go to the nightclub at the Hilton where we can dance and drink until very late.  I bought Colette a special new dress for tonight and we spent the afternoon at the beauty salon having our hair and make up done for our big night out.  Doesn't he look beautiful!  I made Colette pose for photos when we left the salon.  I think he looks pretty happy in these picture.  I think Colette enjoys being the object of Marcus's attention and desire a lot more than he admits!  What do you think?














I'm sure Marcus will be pleased that our sissy lover looks so pretty tonight.