Madison had spent the last few hours in the company of a handsome lifeguard who had taken a lot of interest in Madison after seeing him lounging around the pool in his new blue bikini.
Madison had just returned to the hotel room, and was telling Mother about his evening.
"And what about your new lifeguard friend?" Mother probed.
"Well," Madison began tentatively. "He was really funny and really nice to me at the bar. He paid for my drinks. Then when I told him I had to leave, he insisted on walking me back here from the pub. So..."
"Yes?" Mother prompted.
"So, we walked back along the beach together. He put his arm around me while we walked. At first I was surprised and I almost pulled away. But then I decided that it felt sort of nice. It made me feel safe and protected. And then he kissed me. It made me feel dizzy when he did that."
"And then?" Mother asked, barely able to believe what she was hearing.
"Then he started kissing more. A lot more. It felt so good. Oh Mother, I'm so confused. I know I'm not really a girl, but something happens when I'm with him."
"It's OK, darling," Mother comforted. "I think it's lovely that you're experiencing feelings that women have. He's very handsome and strong and masculine...It's only natural that he would make you feel some girlish, romantic emotions."
After a moment Madison continued, "He wants to see me again. Tomorrow is his day off and he wants to take me out on his friend's boat for the day. I already said yes. Is that OK?"
"Of course, darling. That sounds lovely. Now get some sleep so you will look your best for your big date tomorrow. I think you should wear your leopard print bikini. I think you will look nice in that."
In the morning, Madison put on his new bikini and slipped on a lacy cover-up and his high heeled sandals. He packed a small bag with his lipstick, his sunglasses, his sunscreen and his hair brush. Mother walked him down to the marina where the lifeguard was waiting on his friend's boat.
"Welcome aboard!" he said as he took Madison's hand and helped him step onto the boat. Madison waved good-bye to Mother as the lifeguard maneuvered the boat out of the marina. As they got into open water, the lifeguard stripped off his tee shirt and Madison slipped out of his cover-up. Madison tried not to stare at the handsome lifeguard's tan and muscular body but he couldn't help himself.
The lifeguard offered to let Madison steer the boat for a while. Madison stepped up to the steering wheel and the lifeguard moved in close behind him. As Madison held the wheel, the lifeguard wrapped his strong arms around Madison's little waist. Madison shuddered when the lifeguard began kissing his neck. As the lifeguard pressed himself tighter against Madison's back, Madison could feel the lifeguard's dick stiffening. Madison moaned softly with excitement.
Once they were out in open water, barely in sight of land, Madison and the lifeguard moved to the cushioned benches in the back of the boat and resumed the passionate hugging and kissing that had begun last night. Madison became feverish feeling the lifeguard's strong, hard body pressed hard against his own soft, skinny body. The lifeguard's enormous erection was not well concealed by the nylon swim trunks he was wearing. Completely swept up by the romantic feelings he was having, Madison pulled down the lifeguard's swim trunks, freeing his massive cock. Madison wrapped his delicate, manicured fingers around it and began pumping gently. He then lowered his head into the lifeguard's lap and put the now rock-hard dick in his mouth.
After fifteen minutes of stroking, kissing, licking and sucking, the lifeguard could resist no more and exploded in Madison's mouth, blasting his hot semen down Madison's throat. As the lifeguard came in his mouth, Madison also shuddered with an orgasm, even though his little penis was tightly tucked between his legs.
Before their day at sea was over, Madison would make his lifeguard cum again two more times. Madison felt so fulfilled pleasuring this strong masculine man.
As they returned to shore, Madison could see his Mother waiting on the dock. "Oh dear," thought Madison. "Whatever will I tell Mother about what I did today?"
Madison was having the most wonderful summer of his life. Spending all day, everyday, lounging and sunning himself beside a crowded resort pool wearing a pretty ladies swimsuit was like a dream come true. And the more time he spent pretending to be a pretty girl in a swimsuit, the more his confidence grew.
On the evening that they arrived at their hotel in Miami, Mother suggested to Madison that he might like to try a different style of swimsuit. Mother was going to take Madison to a local mall to go shopping, but as they walked through the resort, they noticed some very cute swimsuits in the window of one of the boutiques off the hotel lobby. In particular, the boutique's window displayed several high waisted bikinis that Mother thought might look wonderful on her sissy son.
Madison was very excited by the idea of wearing a two-piece swimsuit. The helpful saleslady found the bikini in Madison's size in several colors and patterns and Madison picked the three he liked best. In the fitting room, Mother helped him try on the bikinis. Mother made Madison go out into the store wearing the bikini to see himself in the big mirror. The saleslady said that he looked "very chic." Some other customers stopped what they were doing and looked approvingly at the lovely young lady in the cute two-piece who emerged from the fitting room.
In the end, Madison picked out three suits that he liked the best and Mother bought them. Madison was thrilled with his new bikinis. That night he had trouble sleeping because he was so excited that tomorrow he would be wearing one of his new two-piece suits around the hotel pool. He decided that he would wear the black one first.
When tomorrow came and Madison arrived poolside in his new bikini, he started getting a lot of attention almost immediately. Maybe it was the swimsuit or maybe it was just that the men in Miami were more assertive, but Madison was attracting men like moths to a flame!
As soon as Mother and Madison sat down, one of the pool boys started trying to flirt with Matilda. And during lunch, the waiter tried to get Madison's phone number. And later that afternoon, a young businessman brazenly walked up to Madison's lounge chair and started talking with him. At first all this masculine attention made Madison uncomfortable, but after a while he started enjoying it. It made him feel extra feminine and beautiful.
The next day was more of the same. This time Madison wore his new blue bikini. And again, the men seemed to emerge from everywhere trying to get his attention. At one point, a photographer working for the hotel asked to take Madison's picture and asked him to strike a few fun poses while he took pictures.
Towel boys, waiters, other guests -- men of all ages -- were flirting with Madison. It was all just a harmless game and Madison played along. But that was about to change.
After Madison and Mother returned from lunch, one of the lifeguards came over to where they were lounging. The lifeguard was tall, blonde and very handsome. Wearing only his tight red swim trucks, his perfectly muscular physique was on full display. When he started flirting with Madison, Madison turned bright red and was barely able to stammer a reply of any kind. Mother watched all of this with great interest and a little bit of worry. After a few moments, the lifeguard moved on, leaving a confused and embarrassed Madison to sort out what had just happened.
"Well, he seemed nice," Mother innocently observed as they both watched the hunky lifeguard walk away.
"Huh? Oh, yes, I guess," Madison answered distractedly.
For the rest of the afternoon, Madison couldn't stop thinking about the lifeguard. He couldn't even concentrate enough the read his Cosmopolitan magazine.
As Mother and Madison were preparing to head back to the room to get ready for dinner, the lifeguard reappeared. This time he was wearing a tee shirt and baggy shorts, which was somewhat disappointing to a very bewildered Madison. The lifeguard explained that he had just gotten off work and that a few lifeguards and some other off-duty hotel staff were going out to a pub just a short walk from the resort. He asked if Madison would like to join them. Madison began to blush uncontrollably.
Madison couldn't speak. So Mother jumped in. "Well, Madison, I think that could be fun for you. I'm sure you would enjoy spending some time with people more your age. You do want to go, don't you?"
Struggling to make sense of his emotions, Madison replied, "Umm, yes. I do think that sounds like fun."
"Great!" the lifeguard answered enthusiastically. "Are you ready to go now?"
"Here, Madison," Mother said as she handing her son a beach cover-up to wear over his bikini.
"Are you sure you don't mind, Mother?" Madison asked, searching as much for guidance as for permission.
"Of course not dear. Now you have fun. I'm sure it will be just fine." And with that, Madison slipped on his high heeled sandals and off he went with the lifeguard.
When Madison arrived back at the hotel room a few hours later, he was a little drunk and very, very excited. He started telling Mother about his evening -- about the other people he met at the pub, how nice the lifeguard's friends were, the music that was playing, what he drank. Mother was happy that her darling sissy son had enjoyed himself. But she expected she wasn't hearing the whole story.
"And what about your new lifeguard friend?" Mother probed.
"Well..." Madison began tentatively, nervous about telling Mother everything that happened that evening.
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.
