Sissy Madison's Vacation -- Part 1

Every schoolboy loves summer vacation.  But nobody looks forward to summer vacation as much as Matthew. That is because Matthew is a Sissy. And Matthew's Mother lets him be "Madison" all summer long!

In the past, Matthew mostly stayed at home during the summer, enjoying his free time wearing pretty dresses, high heels, jewelry and purfume around the house. Mother was always delighted to spend time with her sissy son, and encouraged him to be as feminine as he wanted to be.

Last summer, Matthew and his Mother did something new. They went on vacation to southern California together as mother and daughter for two weeks! As two ladies they did everything that tourists do in and around LA. Matthew even visited Disneyland as Madison which was great fun.

During their last few days in California, Mother suggested that Madison try wearing a ladies swimsuit and go to the hotel pool. Madison didn't have any swimsuits of his own, so Mother let him borrow one of hers. Madison squeezed himself into Mother's blue and white sheath suit. Mother carefully positioned Madison's breast forms into the cups and used a little make-up to give the appearance of some cleavage.

At first, Madison was nervous about going down to the pool in nothing but a skintight swimsuit. He felt so exposed -- practically naked. And yet he was thrilled by his own reflection in the mirror. After another hour of ensuring that his lipstick, his hair, his nails were all perfect, he worked up the courage to head down to the pool. He slipped on a pair of Mother's high heeled sandals, grabbed a towel and together they rode the elevator down to the pool level.

They found two lounge chairs near the deep end of the pool. Poor Madison was still so anxious about being in public in a ladies swimsuit that Mother ordered him a pina colada, which seemed to help. After some time -- and a second pina colada -- Madison started to relax. He began to see that his secret was safe even wearing nothing but a ladies swimsuit.  

And the more Madison could relax, the more he enjoyed the experience of being one of the pretty girls lounging around the pool, his soft pale skin exposed to the sun and to the breeze and to the eyes of all the other hotel guests. Madison wasn't aware of it, but Mother noticed that some of the men around the pool were staring -- or maybe leering -- at her sissy son.


Since that first experiment was so successful, the next day Mother suggested that they do it again. This time Madison  would wear Mother's black sheath suit. Together they worked to ensure that everything was prefect and that Madison looked like just another pretty girl going for a swim before they left their hotel room.   

This time Madison was much more confident. He knew he looked pretty and feminine in Mother's swimsuit. 

After lounging by the pool for an hour, Mother suggested that they walk to the cafe by the marina for lunch. Madison slipped on Mother's sandals and off they went. As they walked, this time both Mother and Madison became very aware of the stares he was getting, especially from the men they passed. This attention from strange men made Madison a bit uncomfortable and nervous -- but it also felt flattering and a bit exciting...

As they ate lunch, Mother announced that she had already been thinking about next summer.  Since this two week "Mother-Daughter" vacation had been so much fun, Mother said that she thought the two of them should do it again next summer.  But instead of just going away for two short weeks, she thought next year they should go away, to Florida, for six whole weeks.

Madison, of course, was delighted by this idea. He leapt from his chair and gave his Mother a sweet sissy hug!