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.  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.


  1. Tell us more. I need to know more about this sissy

  2. Happy New Year ! Thank you for the newest chapters after hiatus. They are up to your usual standards. I truly enjoy seeing a new addition to this story. Nice characters and a flowing style. More please.

  3. Please, please, please, do continue! I can't wait to get more of this story!

  4. Though I'm not a sissy, I enjoy reading them. I like the quality of your stories and the photos that illustrate them. One thing to note: sometimes you mix up who is with whom. Robert when you mean Mark.
    And yes, I want to see what is going to happen. Please write more.

  5. This comment has been removed by the author.

  6. Please write another chapter. (:

  7. Please keep Tiffany alive, want more.

  8. I love this story line I am really want to see what happens this summer.

  9. I'm Very Much looking forward to your next chapter(s)! Great so far !

  10. I enjoyed ! Any more to come ? I hope so.

  11. I enjoyed ! Any more to come ? I hope so.