The Mistress

The next day, your head was in Carrie's lap. You were jerking off to porn, but she wasn't letting you cum today. She was stroking your hair, watching Fox and Friends, waiting. She'd set you up last week with a doctor, and you were finally receiving hormone replacement therapy to start your own journey. But just the medical treatment wasn't going to be enough. You needed a guide.

At 10 a.m. on the dot, there was a knock on the door. You looked up at Carrie, concerned.

"It's okay, sweetie. This is Mommy's friend," Carrie said reassuringly. She patted your head, and went to the main door. A minute later, Carrie reentered your room, accompanied by a 4'11 perky Korean female.

"Sweetie, this is Jezebel Nguyen. She's Mommy's friend. She runs a sex shop on the west side of town. She's going to be helping you with your transition, since Mommy has a wedding to plan." Jezebel was wearing six inch leather boots to add some height. She had pretty golden skin, long dark hair, and a nose and tongue piercing. She took a long moment to appraise you, finally looking at your aching dick.

"Is she fully erect?" Jezebel asked Carrie. Carrie nodded. Jezebel took out a measuring tape. She started by measuring your pee pee.

"Hmm... 4.75 inches. Smaller than I thought, but she isn't going to be fucking anything. Is she ready to cum?" Carrie laughed.

"She's been ready to cum all morning." Jezebel sat down, petting you, just like Carrie did.

"Cum on, sweetie...cum for me." You started to stroke harder, your eyes rolling back on your head as you watched the bears fucking the boys on your laptop. After a moment, you stained your belly with watery cum.

"That's a good girl. You're quite feminine you know. More so than many boys already on HRT. Are you working out?" You shook your head. "We'll need to fix that. Carrie ... I mean ... Barbie, can we get her an elliptical? She'll need to do lots of squats too. Donkey kicks. Got to get that booty in shape for a boyfriend." She smiled, as if you were both in on a secret.

"I've overseen the transition of a few special girls now. And I know all about you and Barbie. How you used to date. How you wanted her to start seeing your Daddy instead. And how he's got that big engagement ring on her. So no secrets between you and me, hm?" You nodded. "Stand up, darling." She measured your penis, soft and weak now. She thought for a minute, pulling out a flat chastity cage, one that made you appear nonexistent down there. She carefully cleaned your penis, almost clinically, then fit your cage on.

"That's a good girl, not your first time." She measured your waist, your hips, your bust. "Not much body hair. Nice. We'll get that shaved off next time. Do you want to go shopping with me, Carrie? I need to get her some panties and nightwear."

"Maybe next time ... I came over just to make the introductions. Oh, and sweetie ... you can call Jezebel Mistress. And Jez -- my stepdaughter prefers to go by Joanie."