Saturday, August 23, 2014

A Sissy Every Weekend -- Part 5. The School Dance

"Oh please! Oh please! Oh please!" Caroline begged.

"No!" I said. "Why can't one of your friends do it?"

"Because they are all going to the dance already!" Caroline explained.

"Well then ask one of the twins to go!"

"I already told you. The twins are upperclassmen and they aren't allowed at the Freshman/Sophomore Spring Dance," Caroline responded.

"This is crazy!" I insisted.  "I am not going to a prom!"


"But it's NOT a prom!" Caroline insisted. "It's just a school dance. Robert's cousin, Mark, is visiting from Arizona next weekend.  Robert's parents say that Robert can't go to the dance unless Mark can go too.  Please, Tiffany!  If you don't go as Mark's date, then Robert can't go with me. PLEASE!"  She looked like she was about to cry.

I hated seeing Caroline so upset.  I knew that going to the dance with Robert was important to her. "Oh, alright. I'll go. But only as a favor to you."

"You're the best, Tiffany! Thank you!" Caroline gave me a big hug and then ran off to call Robert and let him know that she had found a date for his cousin.







The week went by quickly and the Friday of the dance arrived.  Mother took me out of school early so that I would have plenty of time to get ready for the dance.  When we arrived at the house, Aunt Jenny had already laid out five or six of her nicest dresses for me to choose from.  Mother suggested that I wear the tailored, sleeveless, pink dress with a blue floral pattern.  I slipped it on and it fit perfectly.  At 5:00, a lady arrived at the house to do hair and make-up for Caroline and me. We were finally ready at 7:00 when our dates, Robert and his cousin Mark, arrived.  I was surprised to see that Mark was driving Robert's family's car but then remembered that Mark was a couple of years older than us and had a drivers license.

It turns out that Mark was very tall and and handsome. And he seemed to like how I looked too.  When we were introduced, he came right up to me and gave me a kiss on the cheek.  Nothing like that had ever happened to me before!  I was really embarrassed because everyone was watching when he did that.  But it also felt sort of nice.

Mother insisted on taking pictures of Caroline and me with our dates and then we headed off for the dance.



Tuesday, August 12, 2014

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

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

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

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

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








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

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


















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



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


























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




Friday, August 1, 2014

A Sissy Every Weekend. Part 3. Saturdays on the Sidelines


I don't wear fancy dresses all the time when I visit Aunt Jenny and my cousins. The twins are really good athletes so we spend a lot of time, especially on Saturday mornings, watching their soccer or field hockey games.

When we go to watch their games, I dress very casually, like a girl my age would.  If the weather is warm, I might wear shorts and maybe a little jacket or sweater. Caroline and I stand on the sidelines, with my mother and my aunt, cheering my twin cousins on.



















And while we stand there on the field, we will often run into Caroline's friends from school.  Since I visit every weekend, some of Carolne's friends have gotten to recognize me as Caroline's out-of-town cousin.  Mostly it's Caroline's girl friends that we chat with on the sidelines.  All of Caroline's girl friends are nice and I don't mind talking to them. And of course, no one suspects that I am not a girl.


But sometimes there are boys from Caroline's school that hang out on the sidelines with us too, including Caroline's boyfriend, Robert. He's OK, I guess, but mostly I'm just jealous of him.

There are other boys that talk to us too and some of these seem to take a lot of interest in me.  Sometimes they try to flirt with me and it seems like they are always looking at my legs. That makes me really uncomfortable. I don't like it when men or boys look at me in that sort of hungry way.  And it seems to be happening more and more.  But I work really hard at staying calm. I fight the fear and disgust that builds up in me when boys try to hit on me. I use all of my  strength to stay in character as Tiffany so no one will know my secret.
















Today, we watched the twins play in a State semi-final championship game.  It was very exciting and the twins' team won.  There were a lot of fans at the game, including a couple of boys who wouldn't stop trying to flirt with me.  After the game was over, the twins headed off to the locker room. Mother, Aunt Jenny, Caroline and I then went to get mani-pedis. On the drive to the nail salon, Aunt Jenny said, "Well, it seems like the boys in this town really seem to like Tiffany a lot!"

I thought I was going to die when she said that.

"I know!" Caroline agreed.  "Did you see how Tommy Murphy was practically drooling all over her?"

"Stop it!" I shouted.  

"I'm sorry, dear," Aunt Jenny said.  "I didn't mean to make you uncomfortable.  But you are very pretty and that's what happens to pretty girls like you."

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.