Wednesday, December 31, 2014

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,  It was fairly secluded.  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.



Wednesday, December 24, 2014

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.