An awkward conversation

When Rebeccah lets you into her bedroom, she is visibly upset and your heart fills with compassion. You open your arms and you just hug for a while in silence.

"Sometimes I hate her," Rebeccah whispers, finally speaking. "Or rather, I hate the things she does. The way she manipulates because she things she knows best for everyone. It's infuriating sometimes."

You decide to hold her and let her talk.

"Part of me hates what she has done to you. She's emasculated you, spanked you, diapered you. At this point you are so broken, you just go along with whatever she says. I wonder what she'll do next?"

"I don't think I'm so broken," you say quietly. "I go along with her because I love you and I want to be with you. She made it clear that I have to do what she says, or I have to go. If I really, really hated all of this, I would have left a long time ago."

"You mean, you like it?" she asks, which makes you pause to think whether you really do like it.

"I guess I can tolerate it," you say carefully. "At least at first, I was tolerating it. To be honest, and I want to be honest with you, I have been enjoying some of it.

You feel like you have stumbled into some sort of confession, to yourself and Rebeccah.

"Tell me what parts you like," she says. Some of the gloom leaving her voice.

"Well," you say, thinking hard. "I kind of like being diapered and taken care of. It makes me feel safe and warm, and I haven't felt that way in a long time. "

"I can understand that," says Rebeccah. "I have a confession. She kept me in diapers at home all through high school. It made me feel ashamed, but at the same time, it made me feel cared after. I grew to associate the feeling of a warm soft diaper with mommy's love, but later some of those feelings about wearing a diaper became a little more... sexual. It's all so confusing, but diapering you or watching mommy do it makes me feel turned on and jealous at the same time. And all of this probably explains a few things. Like your bedroom furniture. And how I acted like it wasn't out of the normal when she diapered you."

You are a little stunned at this revelation. It does explain things more clearly. You were beginning to suspect there was more to the story with Rebeccah and her mother.

"What other parts do you like?" Rebeccah asks.

"I guess I'm learning a little more about my sexuality," you say. "We shared a lot with each other when we were in our long distance relationship. You know I can be a little kinky, and you said you liked that about me."

"I do like that about you," she says suggestively. "Come sit on the bed with me, and tell me what you mean."

"I've never worn a chastity cage," you say, sitting next to her and holding her hand. "And I've never fantasized about being emasculated, humiliated or denied sex, but I have to admit that these things have been making me aroused. Like constantly really aroused. Like every time your mother teases me about how small my penis is, or that it doesn't get hard anymore, I feel such a strong jolt of arousal. It's probably good that I've been diapered, because my penis is constantly leaking even though it no longer gets hard."

You open your legs to show her the bead of clear fluid that has formed on the end of your soft nub.

"As crazy as it sounds," you continue, "I am getting off thinking about how my penis may actually be shrinking. I mean it scares me to think that it could be permenant, because I've always been self-conscious about my size, but it also really turns me on for some reason."

"Really? Rebeccah asks. "It does seem smaller. Is it the pills maybe? Or the chastity?"

She reaches down and holds it between her two fingers, and then rubs the drop into the skin with a third finger which makes you give a little groan of pleasure.

"It still feels good to rub it, even though it's not hard?" she asks, moving her finger in a little circle just beneath the head.

"Yes," you gasp quietly. "It might even feel better now. More sensitive."

"Ohhh," she purrs seductively. "Is there anything else you are enjoying? Tell me while I do this. I'm rubbing you the same way I rub my clit when I masturbate."

"The plug," you say, trying to think through the distraction. "That turns me on, I guess. But putting things in my butt makes me feel, I don't know, like I'm doing gay stuff."

"We know you are into women," she whispers. "That's pretty obvious. And there's nothing wrong with doing some experimenting. Doing butt stuff with a woman is for sure not gay. It's just butt stuff. And even if you did something with a guy, it doesn't mean anything other than what it is. The world has moved on from sexual stereotypes."

"That was so hot when you came on my dildo," she says, her voice husky with passion. "And you seemed to come really hard when I told you it looked like you were being fucked by a real cock. Like really hard. I don't know why but it gets me off thinking about you being a little butt slut like that."

You feel your face flush, and it takes a moment for you to regain your composure, especially since she is swirling her finger against you like that.

"I just remembered that I came in here to talk to you about your date," you say finally.

"Oh, yeah," she says, slowing her finger and sounding suddenly sad again. "I should just refuse to go, and take my spanking."

"You know," you say thinking and talking slowly. "I'm only worried that you will like him better and not want to be with me anymore. I don't even feel that jealous thinking about you being out at a resturant with him or whatever. A little bit, but not that much. I just don't want to lose you."

"I would never leave you for someone like that," she says sincerely. "I don't want to leave you for anyone."

You nod, thinking about that.

"That makes me feel better," you say. "Maybe you should go. I think your mother might be right and it might hurt your career if you don't. It's just one date, right?"

"I'm not sure," she says, biting her lip pensively. "He's been flirting with me for a while, and before I met you, I guess I flirted back. I'm worried he will just think I'm being a tease if I let him take me out and, you know, nothing happens. I'm worried that if I don't put a stop to it now, it could be harder to stop later. You know?"

"Then again," she says, musing. "I don't want to have to look for another job now. And I need to use this one as a reference."

"What if you just string him along?" you say. "Eventually he might get tired of the chase and give up. At least it will buy you some time."

"True," she says. "But he's probably going to try to kiss me and get handsy with me at the very least. How will that make you feel?"

You have to stop and think about that one.

"I guess I could be okay with that," you say. "I would be a little jealous, but I know you love me in the end."

"Does this change your mind?" she asks. She scrolls on her phone and then turns it to show you her screen.

There is a text bubble that says "I can't wait for our date Saturday" and beneath that is a picture of a hard cock. It looks like it is large, veiny and thick. You let out a breath.

"That's a big cock," you say. "Wait, he sounds like you already agreed to a date..."

"Not exactly," she says, blushing. "He just assumed I would accept, even when I told him I would think about it. I told you he's cocky."

She has been rubbing her finger under the head of your penis during this whole conversation and she holds up her finger, showing you that it is coated with clear fluid.

"Hey, how come you started dribbling like crazy when I showed you his cock?" she asks suspiciously. "Is it from looking at a picture of a cock, or because he sent me a picture of his before our date?"

Now it's your turn to blush.

"I guess because he sent it to you before your date," you mutter uncomfortably.

"Is this situation turning you on?" she asks, looking at you directly and making you feel bashful.

"Maybe?" you say. "I think it is turning me on. I'm sorry, that's weird, isn't it?"

"Yes, that's weird," she says, seeming to be thinking it over. "But I like that you're weird. If I go on this date, we should talk about what might happen, so we will be prepared."

You nod, and she goes back to teasing the underside of your little nub.

"What if he tries to kiss me?" she muses. "What should I do?"

"I guess you should just go with it," you say.

"You're dribbling again, just talking about kissing," she teases you. "What if he wants to grab my breasts?"

"I guess I would be okay with that," you murmur.

"Inside my bra?" she asks.

You nod again. Your face feels like it is starting to burn.

"My panties?" she teases seductively. "You are dripping wet down there. Will you be okay if he wants to put his hand in my panties? Rub my pussy?"

You let out a little moan, as she plays with your nub.

You nod slightly.

"Was that a yes?" she asks. "You are okay if he plays with my pussy? Tell me out loud."

"Yes," you say. Your voice cracks and you lick your lips. She is rubbing you in quick circles now, her fingertip sliding wetly over your sensitive head.

"What if he wants to put that big cock in my pussy?" she whispers seductively. "Should I let him?"

Your hips start to convulse and you start to come. Your little penis squrts on her hand and the floor and you are left laying on your back, trembling and gasping.

She puts her two cum covered fingers in your open mouth and you impulsively start sucking on them.

"I'll take that as a yes," she says quietly.