A Sissy Every Weekend -- Part 8. Out to Brunch

When I came downstairs in the morning, everyone was already up but still dressed in their nightgowns.  "I understand that you and Caroline are going to out brunch this morning," Mother said as she sipped her coffee.  "At the Hilton.  They have a very lovely brunch."

The twins were eating breakfast.  "Wow!  A second date just 12 hours after the first date.  That must be some sort of record!" The twins started giggling at that.  Even Mother and Aunt Jenny struggled to suppress a bit of a laugh at the joke.  I tried not to let it bother me.   

"Don't pick on Tiffany," Caroline said, coming to my rescue. "She only doing this as a favor to me."

"Well, let's get you girls dressed," Aunt Jenny said.  Caroline and I followed Aunt Jenny upstairs and into her walk-in closet.  "What would be good for a fancy brunch...?" she thought out loud.  She suggest a two-piece outfit for Caroline. For me, she picked out a blue dress with orange trim. It was brand new and still had the tags on it.  "Tiff, I think this will look great on you. And I have a purse and shoes to go with it.  Now you two need to hurry up and get ready.  I'll drive you downtown in 45 minutes," she said.

Caroline and I went back to our bedroom where we quickly showered and got ourselves ready.  As I slipped on my bra and placed the little falsies into the cups it struck me what I was doing. It was just as the twins said.  I was going on a second date -- with a boy.  And here I was rushing to make myself look pretty -- borrowing a fancy dress and shoes, doing my hair, putting on make-up and perfume -- all things a girls does to make herself attractive to men.  I started getting upset as I sat there at the vanity wearing just my bra and panties.  Caroline came over and slid onto the vanity stool next to me.  "Don't worry, Tiffy.  You'll do just fine today."

"It's just that...that..." I stammered.

"What, Sweetie?"

"It's just that this is all wrong.  I shouldn't be getting all dressed up to be out with a boy!"

"Oh, Tiffy, don't think about it like that.  We're just going out to have some fun.  We will have a delicious brunch at a fancy hotel and then we'll come home.  And we're doing it together -- you and me -- because we're best friends.  BFFs!  Now we really do need to hurry.  We have to leave in about 10 minutes."

Caroline's pep talk settled me down a bit.  As I finished doing my make-up I thought about what happened last night in the bedroom -- and how I hoped it would happen again.

"Come on, girls!" Aunt Jenny shouted up the stairs.  "Time to go."

When Caroline and I came down the stairs, the twins and the moms told us we both looked gorgeous.  That made me feel good.  Mother insisted on taking photos before we piled into Aunt Jenny's car and in 20 minutes we were at the Hilton.  On the drive over, I kept thinking about how Caroline had "shown her appreciation" last night in my bed.  But I was also thinking about Mark and how it was sort of exciting to be seeing him again. All of these feelings were swirling around in my head. It sort of made me feel dizzy.

Aunt Jenny dropped us at the Hilton and we went in.  Mark, Robert and Robert's parents were already in the restaurant.  Caroline introduced me to Robert's parents and Mark gave me a little hug and kiss.  I'm sure my face turned bright red when he did that.  We sat down and started looking at the menu.  Everybody ordered Bloody Mary's, so I ordered one too.  I guess they don't ask for ID at fancy restaurants like this.

I was feeling pretty nervous but I started to relax a bit after a few sips of my Bloody Mary.  As we were all chatting, I felt Mark's hand on my thigh under the table.  I didn't know what to do.  I sort of wanted to pull away but I thought that might be rude or make him suspicious. So I just let him keep feeling my soft, stockinged leg under the table.

As we chatted, Robert's father said, "Well, girls, has Mark told you the big news?  Mark is going to work at my law firm this summer.  So he'll be living with us right here starting in June."

I was speechless, but Caroline jumped in.  "Really!?!  That's terrific news!  Isn't it Tiffany?"  I nodded and managed a feeble "yes."

Caroline continued, "This will be great.  Then the four of us can go out together all the time -- all summer long!"  Mark gave me a big smile.  

I could see that Caroline was thinking about something and then she spoke up again.  "Well we have big news too!  Tiffany is going to work at my mom's shop this summer and she'll be staying at my house all summer."  None of this was true -- or at least it was all news to me.  But I certainly couldn't start arguing with her right then and there.

I managed to get through brunch.  After two Bloody Mary's I was feeling a little tipsy.  Conversation was pleasant and Robert's hands rarely moved off my thigh for the entire meal.  Robert's mother at one point told me that I was "very beautiful" and that was going to phone Mark's mother as soon as she got home to tell her what a "pretty and delightful" girl Mark was seeing.  When she said that I felt Caroline's hand on my other leg, giving my thigh a little squeeze.  "Oh God!" I thought at that moment.  "I have Caroline's hand on my left thigh and Robert's hand on my right.  What if their hands touch!"  I reflexively spread my knees apart to keep their hands from touching -- but then I realized that Mark might interpret this as some kind of invitation, so I quickly snapped my legs together again.  Anyway, Caroline moved her hand before there was any sort of contact between the two of them.

"Why don't you kids go for a walk around the area while we finish our coffees and pay the bill," Robert's mother suggested.  The four of us went outside and walked around the downtown.  Mark took my hand as we walked along looking at the various store windows that we passed.  Caroline and Robert walked right behind us.  I felt very self conscious knowing that Caroline was seeing me holding hands with a boy. It felt strange but also sort of nice to walk hand-in-hand with this big handsome young man.

We turned down a little brick path that ran between two buildings.  Mark suggested that we sit on one of the benches. We sat down and Mark put his arm around my shoulder and pulled me close to him.  Caroline and Robert sat on a bench directly across from us.  Then Caroline and Robert started making out.  I looked up at Mark and knew that that is what he wanted to do too.  And so we did.  Mark wrapped both arms around me and we started really going at it.  I put my arms around him too.  At one point I found myself sitting on his lap as he aggressively french kissed me.  His hands started playing with my little fake boobs.  I made him stop because I was afraid that one of my falsies might fall out!

"I guess we should head back to the hotel," I heard Caroline say.  I pulled myself away from Mark and saw that Caroline and Robert were already on their feet watching our little make-out show.

By the time we got back to the hotel Aunt Jenny was already there to pick us up.  We thanked Robert's parents and said our good-byes to Robert and Mark -- demurely this time as we had an audience.

Caroline was very animated on the drive back home, telling her mother every detail of the brunch (except the making out part).  I barely said two words as the experience of the last couple of hours -- and last night -- had left me confused and exhausted.

Where would all this end?  What would the summer hold?  How will Tiffany keep his secret safe from his new "boyfriend"?  And what about Caroline and Tiffany's new intimacy?  

There is much more of the story to be told. Please let me know if you would like me to write more chapters.

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

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

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

I had no idea what she was suggesting.

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

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

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

I couldn't believe this was really happening.

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

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

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

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

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

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

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

A Sissy Every Weekend -- Part 6 The School Dance Continued

Well, the dance wasn't as awful as I had feared it would be.  In fact, I guess it was sort of fun.

Robert and Caroline and Mark and I arrived at the dance around 8:00.  Caroline's high school gym had been decorated with balloons and streamers and fancy lighting.  We spent the first hour or so chatting with Caroline's friends and their dates.  Everyone was very nice to me and several girls told me that I looked very pretty.  After a while I started to relax.

I relaxed a lot more after taking a few swigs from the flask that Robert had sneaked into the gym.  Caroline drank more than me but it didn't seem to effect her very much.  But just a few sips made me feel a little tipsy.

The band started playing some slow music and Mark asked me to dance.  I knew this was going to happen at some point but I was very nervous.  He took me by the hand and led me out to the middle of the dance floor.  He wrapped his arms around me and we started swaying to the music.  He told me that I was very beautiful and that he was having a great time being with me.  Before I could say anything back, he kissed me!

I was so surprised that I almost fainted when he did that.  I was about to pull away from him but then I realized that being kissed by Mark wasn't so terrible.  I also realized that I enjoyed how it felt being held tightly in his strong arms.  I looked up into Robert's eyes and I let him kiss me again. This time he put his tongue in my mouth!

We danced together for a few more songs.  I could feel that his dick was hard as we danced together -- it felt like his dick must be huge!  I tried not to think about that as I placed my head on his strong shoulder and wrapped my arms around him more tightly.  His hands slid down my dress and he started feeling up my bottom.  It felt strange to be caressed by another boy this way.

The rest of the evening flew by.  The music ended and it was time to go home.  We said our good-byes to Caroline's friends and got back into the car and Mark drove us home.  I let Mark hold my hand as he drove while Caroline and Robert made out in the back seat.

When we got back to Aunt Jenny's house, Caroline and Robert went up the front door to say good night.  I stayed behind in the car to say good night to Mark.  He leaned over and starting kissing me again, really hard and really deep.  I let him.

He made me promise that I would see him again before he unwrapped his strong arms from around my skinny shoulders.  I walked up the steps to Aunt Jenny's house and gave Mark a little wave before he drove off.

When Caroline and I went inside, everyone was still awake and waiting for us.  "How was it?"  "Did you have a good time?"  "How was the band?" Mom and Aunt Jenny and the twins showered us with questions.  Caroline did most of the talking and reported that the night had been really, really fun.

"Well, Tiffany, did you have fun?  And what was Mark like?" Aunt Jenny asked.  The twins were anxious to hear my answer.

"Yes, the dance was pretty fun, I guess.  Mark seemed nice enough," I blandly replied.

"Nice enough!" Caroline replied with a big laugh. "I thought Mark was going to get you pregnant right there on the dance floor!"

That made me so embarrassed that I burst into tears and ran straight up to our bedroom and fell onto my bed, sobbing into my pillow.

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.

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

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

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

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

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








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

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


















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

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

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

A Sissy Every Weekend. Part 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."

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!

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'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.  

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.

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.