Sissy Madison's Vacation -- Part 2

Summer was here again.  The winter had seemed to last forever for poor Matthew/Madison because he was so excited about the summer vacation he was going to take with his Mother.

This summer they were going to visit Florida for six weeks!  Mother had made arrangements for them to stay at several resorts along the Atlantic coast.  They would fly into Jacksonville, then work their way slowly down the coast ending in Miami.  And Matthew would get to be Madison the whole time!

Mother had started planning months in advance, organizing their activities and outfits for the trip.  Their first stop would be at a beauty salon in Jacksonville where Matthew could get hair extensions and long, pretty nails applied.

They would stay at five different resorts along the coast as they headed south.  Mother had researched all sorts of things to do -- sightseeing, activities, restaurants -- to fill their time.

But once they got to Florida and Madison got his hair and nail extensions, all he wanted to do was wear his pretty new swimsuits and hang out by the pool.  Last summer, Madison wore his mother's swimsuits. This year, he would wear his very own pretty swimsuits that mother had bought for him. Mother had picked out two swimsuits for her sissy son. Madison had tried them on at home and they fit him well and they securely held his breast forms. One of the suits was a pink and white striped sheath suit and the other was a blue and white polka dot suit.  Both helped to give Madison the appearance of sexy feminine curves.


Every morning, Madison and his mother would order breakfast from room service.  After eating, Madison would spend the next two hours getting ready.  He refused to go down to the resort pool until his hair, his make-up, nails -- everything was perfect. Then, by mid-morning, Madison would be down at the pool, sunbathing on a lounge chair, reading a fashion magazine and experiencing the nervous thrill of being stared at by other hotel guests -- especially all the men! He loved showing off his long, smooth legs and feeling the cool breeze and the warm sun on his exposed shoulders.  It felt so sensual to rub suntan lotion onto his soft, exposed skin.


And while Mother might have wanted to do other things, she indulged her sissy son's desire  to spend all day beside the pool showing off how pretty he looked and felt. Together they would eat lunch beside the pool.  They would go for brief dips in the pool or the hot tub.  There was nothing else Madison wanted to do.

During their stay at the first resort, Madison wore both of his new swimsuits, alternating the pink one and blue one each day. But since he was wearing his swimsuits all day, every day, Mother suggested that they take a break from the pool and go shopping for some more swimsuits for her sissy son.

They drove to a fancy mall where Mother found a style of swimsuit that she thought would look nice on Madison. It was a tank suit with thin straps and covered with cute ruffles. She found the suit in the right size in three different colors -- one in black, one in a pink check and one in blue with polka dots. 




Madison tried them all on in the fitting room. When Mother asked Madison which one he wanted, he said, "Can I have all three?" Mother simply could resist anything her darling sissy son asked for and so Madison had three new cute swimsuits to show off in.