Jackie Begins her Transition

He stood up and walked behind her ass on display, with her tiny caged clitty dangling between her legs. He admired the ass, especially now that he knew that it belonged to a boy, and gave it a light slap. He massaged her cheeks for a minute before placing his hard cock on her ass. He pumped it up and down her soft butt and said, "Beg for it."

She moaned and looked back at him with begging eyes, "Oh please! I want it in me. I want to feel you deep in me."

So he planted one more light slap on her cheek then positioned his head at her sissy hole. With both hands he grabbed her hips and began to push in. She was still pretty tight but she had gotten to the point where it no longer hurt for long. It was almost immediately to ecstasy for both of them. He kept pushing, waiting for her to tell him to stop. He expected that she wouldn't be able to take all of him, but he was wrong. She began to moan deeply as he penetrated her inch by inch. Until finally his crotch pressed into her ass and his entire cock had skewered her.

He held it there for a moment before pulling back. She was still moaning and she could feel his grip on her hips stay tight. He began to pump. His cock thrust in and out of her sissy hole faster with every push. He went all the way down and almost all the way out with every blow, each time tickling her G-spot and making her feel warm inside. As his thrusting got faster and faster, she began to shake forward and back onto his rod. Her little clitty began to swing back and forth between her legs. Her ass beginning to clap against his crotch.

They fucked for twenty minutes. Jackie was used to longer with Martin, but since it was Robin's first time in her ass she expected him to pop quick. He grabbed her hair and held her against him as he came deep inside her ass. She moaned in bliss as he did so. They held it there for a few moments before she pulled herself off his dick. She turned and kissed him. She whispered into his ear, "You just came in a boy, how does that make you feel?"

And he grabbed her ass in one hand tightly, shaking it and said, "You're no boy. You're a bitch. You're MY bitch."

They kissed some more and he left. She cleaned herself up and finished what she had to do for the night until Martin came home. She made them dinner and they enjoyed their time as they watched a movie until late. They went to bed and Martin fucked her in doggy style for half an hour. Jackie drifted off to sleep next to her first lover and thought about her second. She couldn't help but smile at how promiscuous she was being, and at how much she was loving her new life. She fell asleep thinking of sex.

The next day went a little like the day before. She woke up and kissed Martin goodbye. She went back to sleep for another few hours before actually getting up for the day. She prepared herself, dressing in a nice sun dress with some slutty makeup and four inch heels. She went downstairs and began her chores. She worked until one, and as she was planning to change into some work clothes to go work on her garden Robin walked in the door. He saw Jackie dressed as she was, standing in the kitchen and immediately walked up to her and kissing her. He grabbed her ass and while kissing began to move her back for the couch.

She was taken off-guard by this but had no objection. She sucked again for a while, then he fucked her ass like he had the day before until they both climaxed. They sat on the couch and cuddled for maybe forty minutes. They discussed things, life, and what she was hoping for. He asked her what she wanted to do with herself, and though she had never thought about it fully she responded, "I want to do what I'm doing now. Staying at home and being fucked."

"You want to be a stay at home wife then?" He asked her.

"I guess. If you can call me a wife."

"Of course you are. You'd be one smoking wife."

She just smiled and kissed his cheek. They sat in silence for a minute or two before he said, "Who's wife?"

"I don't know. Whatever guy I fall in love with I guess."

"What about me?" He said, partly joking.

"Hah," She laughed, "You're awesome but to be a stay at home wife you need a husband who can provide. You gotta have a pretty good job for that."

"Well I'm gonna be a basketball star. If that's not a provider's job then I don't know what is."

She just giggled and stayed silent. They spent a few more minutes with each other before he had to leave. She finally went upstairs and changed into her work clothes to go do her garden. After that the night finished much like yesterdays. Except now she was thinking about what Robin had asked her. She knew she couldn't live with Martin forever, and she did mean what she said she wanted to do. So she wondered who she could find to settle down with. Robin was a good fuck-buddy, but she didn't consider their relationship to be heading toward anything serious. She didn't really enjoy his type for much more than what she was already getting from him. That thought, however, hit her with a strange sense of curiosity. She didn't know what her type was. Maybe she needed to find out.