Sissy Madison's Vacation -- Part 4

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?"