You get milked

Rebeccah's mother helps you onto your changing table and removes your diaper, noticing your little penis has been leaking again. She arches an eyebrow, but doesn't comment, and gently twists your plug, pulling it out.

"It's not healthy for a prostate to go for too long without doing what it... does," instructs Rebeccah's mother, as she straps a rubber glove onto her right hand. She hands another glove to Rebeccah. "Since poor sweet boy's little penis has been locked up - for good reason, I might add - we need to provide another way for his prostate to get it's exercise.

Rebeccah's mother gently inserts a finger into your rectum, and then another, after finding how easily the first went in. She then starts to move her finger tips around, as if searching for something. You feel a strange pressure, that makes your penis twitch, and at the same time makes you feel in a vague way that you have to pee.

"About two inches inside, toward the front, there's a lump," she continues, speaking clinically. "And now that I've found it, I am going to begin to gently massage it with my fingertips."

You look down and see your penis twitch with each press of her fingertips and a few drops of clear fluid dribble out.

"Rebeccah, you need to be able to do this too," says Rebeccah's mother. "Lubricate your fingers and see if you can find his prostate."

Rebeccah takes her mother's place, and having applied the lubrication, thrusts both fingers inside you at once.

"That went in pretty easily," she remarks, as she probes for your prostate. "Ahh, there it is."

The strange sensation starts again as she begins massaging.

"Mommy, how long do I need to massage it?" Rebeccah asks. She's looking directly at you and she smiles deviously.

"The massage should continue until he squirts prostate fluid," says her mother. "Which is not exactly the same as semen. It's just one part of it. Hopefully it doesn't take too long for his little penis to squirt."

Rebeccah continues to massage you, and you do feel a pressure building up, but you aren't sure if it's working.

"Do you like that," asks Rebeccah. "Do you feel like it's working?"

"It, um, feels kind of goood," you say, feeling unsure and embarassed. "I don't know if it will make me cum."

Rebeccah starts to massage with a little more firm pressure, and at the same time, teases the skin she can reach through your chastity cage with her other hand.

You let out an invoulentary whimper.

"I think he may need some mental stimulation," says Rebeccah's mother, reaching for her phone. "Let's see what I caught him looking at yesterday..."

She flicks her finger on her screen a few times.

"What do you think, Rebeccah," she asks. "Here's what he was looking at in order: Cuckold porn, adult diapers, diaper sissy, and mommy dom."

"Hmm," muses Rebeccah, trying to hold back a smirk. "That's quite a list. He was busy yesterday. Let's try mommy dom. That was the last thing he was looking at."

If Rebeccah chose that to tease her mother, she gives no sign as her mother shrugs and clicks on a link. She holds her phone in front of your face and you are **** in humiliation to watch the video in front of your fiance and her mother.

The woman in the video has huge breasts and she mentions that she's lactating. Talking directly to the camera, she offers to show her breasts and then squeezes her nipples, causing milky drops to form. The humiliation of being **** to watch in front of Rebeccah and her mother is incredibly embarassing, and at the same time arousing. The massage continues, and you start to get a vague burning sensation and a pressure building. You whimper a little and squirm on the changing table.

The woman in the video offers her nipple, instructing you to be a good boy, and nurse on mommy's breast, and if you want, you can stroke your hard little penis. Obviously you can't stroke yourself, but the thought makes the pressure build even more.

"I think we need to move this along," announces Rebeccah's mother.

She pulls the phone from your face and unbuttons her blouse, explosing a black lacy bra, which she pushes to the side so she can pull her big, soft breast from the cup. As Rebeccah continues to massage your prostate, her mother leans over you, pressing her thick nipple into your mouth, and whithout wasting a thought, you begin to suckle hungrily, drawing her nipple deep into your mouth. After a mere three sucks, you feel a fire eminate from your prostate and engulf your entire body, and you writhe, whimpering on the table, all without releasing her nipple from your mouth.

As you come to your senses, you realize you are still gently sucking the nipple in your mouth and Rebeccah's mother is stroking your hair.

"That's a good boy," she murmurs, finally pulling her nipple free.

She pats you affectionately on the cheek before putting her breast away. Her face seems flushed and she seems a little flustered.

"Rebeccah, why don't you clean up here and get sweet boy in a fresh diaper?" she says distractedly. "I think I need to take a little nap."

With that, you are alone in the room with your fiance, who begins to clean up the sticky mess on your stomach.