A Sissy and his Mother Have a Weekend Adventure -- Part 1

My son, Jamie, and I share a big secret.  Jamie is Sissy.  And while he tries his best to act like a boy at school, at home he is my Sissy daughter, Janey.  Over the years, Janey has really blossomed into a delightful young "lady" and I love the special times I get to spend with the daughter I never had.

Last weekend, we had the most wonderful adventure. After Jamie came home from school on Friday afternoon, we drove into the city, which is only a couple of hours away. We checked into our hotel and that's when the real fun began. Jamie stripped off his boy clothes, slipped on a fluffy bathrobe and started becoming my daughter Janey. Over the next hour and a half, Janey and I got ourselves all dolled up for a night in the city.

We finished doing our hair and makeup. I helped Janey zip up the new little black dress that I had bought for him. I let him borrow one of my necklaces and a fun oversized purse. Janey put on his favorite strappy platform sandals and he was ready.  Doesn't he look lovely!?!

We then went to the ballet which we both loved! Then we enjoyed a late dinner at a fancy French restaurant. It was marvelous.  The waiters fawned over my pretty daughter.  One even jokingly begged Janey for a date!  Janey was a good sport and giggled and blushed like a young lady would. 

Exhausted, we went back to the hotel where we slipped into our nighties and went to bed.

On Saturday morning, Janey decided that he wanted to wear his red dress.  It is very simple and yet so elegant.  And Janey knows he looks fabulous in it!  

We had breakfast at the hotel and then went to the art museum which had a wonderful exhibit on ballgowns from the 18th and 19th centuries.  Janey and I both enjoyed this very much.  We spent so much time at this one exhibit that we barely saw anything else in the museum. 

After we were done at the museum, we walked over to the Ritz Hotel where they serve the most delightful afternoon tea. Janey and enjoyed all the little sandwiches and sweets that were served.  Elegantly dressed ladies sat at all the other tables; some tables apeared to have mothers and daughters having tea together -- just like Janey and me!  I felt so fortunate to be able to share this experience with my special Janey.

After tea, we spent the rest of the afternoon shopping. At the lingerie shop I bought Janey some new bras and panties and stockings.  We then found some shoes for Janey at the big department store -- a pair of black patent leather slingbacks with a three inch heel and some cute sandals for the summer. Then we visited a couple of the designer boutiques and I had Janey try on literally dozens of dresses!  In the end we only bought one dress for Janey -- oh, but what a dress. 











We returned back to our hotel exhausted carrying all of our new purchases.  Since we were tired, we decided that we would have dinner downstairs at our hotel.  As we started to get ready for dinner, Janey asked me, "Mother, do you think I can wear my new dress tonight -- the one you bought me this afternoon?"

"Of course, sweety,"  I replied.  "I am sure that your new dress will be just perfect for tonight.  The hotel's restaurant is rather fancy and I am sure people will be dressed very nicely.  So yes, please wear your new dress."

We finished doing our make-up and fixing our hair.  Janey slipped on his new dress and modeled it for me.  "Oh, Janey," I sighed.  "You look...amazing."  A tear started to well up in my eye as I gazed at my beautiful, elegant son.