Matchmaking Trap- Part 3: Donna

They were rapidly eliminating his excuses. He knew that they all wanted him to become a woman, for both his sake and Deanna's. Well, he'd seen the army slogan, "Be All That You Can Be" once, and that seemed to sum up the issue. He had more potential as a woman than as a man, plain and simple. If you can't be hot as a guy, why not turn heads as a girl?

"Alright, I'll be your girlfriend, if I can't be your boyfriend!"

"Splendid! We can start today! You were always rather cute, so making you a girl just makes better use of your assets.", Deanna stated.

"What's my new name?"

"Donna. Logical alteration of Donald, or Donny, as it were.", Chad suggested.

Deanna and Roberta nodded their agreement.

"Well, Chad, I'm a slave, so I can't keep him as a slave, can I? We can be lovers, but he needs a master or mistress better suited to the task of controlling him. I'm too submissive for that."

"I'll own him here, and Roberta will dominate him at her place, just like you."

"Sounds like a great plan, son. However, if we're going to turn 'Donna' here into a girl, we should stop using masculine pronouns, shouldn't we? She needs to learn to think of herself as a woman."

"Agreed. Donna is her name, and she shall be referred to in the feminine from now on."

"Okay, so, Donna, we need to start feminizing you right away, ok? We'll start with undressing, if that's fine with Master here."

"Very good, slave. That will work. Donna will take off her old, masculine clothes, now."

"Donna" did as she was told. She stripped down to total nudity, revealing, sure enough, the smallest cock Chad had seen since puberty.
She really did belong to the beta male category, and soon she would be a female instead.

"Alright, Deanna, I want you to take her into the bathroom and shave all of that unladylike hair off of her body. Get her nice and smooth."

Shaving him took a while, but Deanna knew what she was doing. She eventually had him completely bare of body hair of any kind, except above his neck, of course. The beard would have to be dealt with by electralysis. Meanwhile, however, wax would do. Donna winced in agony as she ripped the stuff off his face, but he let her do it anyway.
Finally, it was time to apply makeup, and she did an expert job, as she was a stylist.

"Okay, now. Look at yourself in the vanity mirror and see the lady you're becoming, alright?"

Donna did so, and she saw that she really was looking more feminine by the minute. Her hair was even re-styled in a feminine way, which was all that Deanna could do for her, given its shortness. She was looking at a woman, it really seemed, and she had to admit that it made her hard to see her own reflection. She was getting aroused by a woman besides Deanna for the first time in months, and that woman was herself!

What could she do? She wanted to thank Deanna for doing this for her- turning her into a lovely, graceful woman. She moved over to kiss her ex-girlfriend, and was pleasantly surprised at the passionate liplock that followed. Deanna was kissing her back, more erotically than she had ever kissed during their relationship. Obviously, the Pygmalion-like work was having an effect on its creator, who was excited by the woman she had made out of Donna.

"I see that Donna interests you alot, Deanna.", Chad said from behind her.

"Yes, Master. Donna is much sexier than Donny, and she is truly ready to be dressed up as a girl and fucked like one."

"You want to fuck Donna in a lesbian manner?"

"If that's ok with you, Master."

"It is. Fuck Donna in the ass with the strap-on."

"Yes, Master."

Deanna then led Donna by the hand to the master bedroom, where she took out the dildo with a thigh harness, and began to put it on her.
Donna was looking rather worried, but Deanna assured her that one day she would get her turn, although that wouldn't happen while she still had a dick.

"Your dick is not going into this pussy ever again. You are a woman now, and women don't shoot sperm into pussies. No masculine behavior is permitted after today, because you are a lady, and a lady behaves in a feminine way."

She directed Donna to lie down on the bed, on her stomach, and then she mounted her, taking the lube first and applying it to Donna's virgin butthole, before she inserted her dildo into her bowels. She began to ride her rather fiercely, apparently unconcerned about the inevitable pain of the initial sodomy. Fucking Donna's ass was an incredible new high, as she found herself spanking and fondling those smooth, reddened cheeks. This shaved bottom had a wonderful feel to it, and Donna was evidently beginning to enjoy the experience.

Deanna kept butt-fucking Donna for what seemed liked a whole day to the poor transvestite, but soon, the prostate was showing its reaction. Donna's cock grew, and she suddenly ejaculated, in a way that would be considered premature, if she was going to penetrate a pussy. 

Deanna looked at the amazing scene in front of her. She was butt-fucking a man who looked more like a woman, and the transvestite was cumming from the excitement. This made Deanna cum herself, and then she heard chuckling and giggling.

Chad and Roberta were clearly enjoying the sight of Deanna's ex taking it up her ass. Chad winked at Deanna, and she blew him a kiss. There would be no more question of who was the man Deanna loved, because the only rival was now her woman instead.