Dress Up

It seemed like a fun game. A little dress-up and pretend. Sure there were rules and the penalty was a spanking if he was “naughty”, but she was paying attention to him and his penis was thinking for him. 

At first, it was just a little weird. She looked pretty and was so excited about finding him clothes and making him looking “pretty”. He didn’t know why he was even playing the game but the more she paid attention to him, the more he was pulled into the game.

It started modest but as the game progressed, he found himself dressed in skimpier, tighter, and sexier clothes by the older woman. She was thrilled with each outfit, each adjustment, and she kept touching him gently, tenderly, and sensually. 

She was searching for the perfect outfit, she told him. He tried on pants, shorts, and then dresses and skirts. The skirts became shorter and then he was standing before her only in a pair of silk panties. His hard penis strained against the fronts as she praised him for looking so pretty. He felt pretty, sexy, and aroused but also nervous. Where was this going? What did she have in mind? He realized that he had no idea how the game ended.

The outfit was frilly but also tight with stockings, delicate shoes, and a locket. The panties didn’t match and worse still, there were none that would match. She decided that he didn’t really need the panties. He was shy but she insisted that he take them off. His privates finally bared, he fidgeted wanting to cover up but not sure if that was allowed. “Oh, perfect!” she exclaimed, “let’s go get some ice cream at that restaurant you like so much.” 

He didn’t know what to say. He wasn’t leaving the house dressed as a girl and certain not naked from the waist down. He looked shocked and immediately forgot how he promised to do everything his mommy asked of him. Thinking it was a joke, he suddenly laughed. She didn’t laugh back. “I’ll just put some other clothes on,” he said tentatively. 

She just shook her head, “no, like this. It’ll be fine. Lots of little girls play dress up. You will fit right in. No one will even look twice at you,” she said with not even the slightest hint of humor. 

“I don’t want to,” he whined. 

It was the excuse she had been waiting for. Seemingly from nowhere the brush appeared in her hand as she patted her lap. “Time for spanking, I think,” she declared. “That will teach you to obey me.” 

Sure, he knew this was a possibility but suddenly he realized this was what she intended all along. Maybe he could get out of it but she wouldn’t play with him again. And she was bigger and stronger, too. Even as he nervously weighed his few options, he knew she was going to spank him.