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Good day for a milking

I wrote this some time ago and remembered I had yet to post it. I’ve recently become interested in prostate milking and I thought I’d try writing an erotic piece about it. Feel free to tell me if I got it all wrong.

“Do you know what today is, darling?”

I observe the expected confused look on your face without emotion, but it’s with delight that I note the blush that first begins to creep up your neck and colors your ears before settling in your cheeks.

“It’s my milking day, Mistress?”

I smile more because of your blushing than your remembrance of the proper salutation.

“Good boy. That is correct. Today is your milking day. Are you excited, boy?”

The blush deepens.

“Y-yes, Mistress.”
“As you should be.”
“Now run along and clean your bottom and pee if you need to.”
“Yes, Mistress.”

I retrieve plastic gloves and lube and lay out a towel at the end of the bed. I watch as you reenter the room several minutes after I sent you out.

“Are you clean, boy?”

Without word, you walk toward me and bend over with your bottom in my face, legs slightly apart. I pull on a glove and spread your fleshy cheeks. Your asshole is pink and clean. With a little gentle prodding, I convince your anus to open a little so I can get a better visual confirmation.

“Good boy. You please your Mistress.”

Smartly, you do not move from your position until I tell you to. We’d had trouble with that in the past, but after a special punishment session you’ve gotten much better of late.

“You may assume your position at the foot of the bed, boy.”

You move until you’re standing at the foot of the bed, your legs farther apart than when you’d bent over in front of me, but not far enough that you would lose your balance. You lean forward and place your palms on either side of the towel. Your cock and balls dangle above the towel, waiting for that moment when the fluid leaks out.

My first glove long discarded, I slip on another one and grab the bottle of anal lube. I step behind you and first massage your ass cheeks. I stop when you start to move against my hands.

“Have you forgotten you place, boy?”
“N-no, Mistress. I’m sorry. I won’t move again.”
“You had better not. I would rather not get out the cane, but you know I will not hesitate if it is necessary.”

A whimper escapes your mouth.

“I promise I won’t move, Mistress. There won’t be a need for the cane, although I well know it’s ultimately your choice, Mistress.”

I smile at your obedience, at your ass in the air for me, awaiting the pleasure I can either give you or withhold.

“Now this is going to be a bit c—“

You gasp before I finish the sentence. I love making you think I’m giving you a warning, a chance to steel yourself against sensation, but instead I catch you off guard and elicit another whimper. I lube your lovely little puckered asshole and begin working my index finger inside, going slow but steady, always gauging your reaction. You relax and open to my touch, sighing once my finger is all the way inside. I twist my finger around hearing you moan for me. Your muscle clenches around my finger. Losing yourself in the moment you push back against my finger trying to make me fuck you. I slap your ass with my other hand.

“I told you to hold still, boy. I will end this right here and now and get the cane.”
“Oh, no, Mistress! I’m sorry. Please, please don’t stop!”

I slap your ass again, harder this time to drive the point home. You cry out but don’t move again. I angle my finger inside your ass searching for the little round bulb that is your prostate. It isn’t long before I find it but I pull back after that initial touch, my finger not quite there…but just there, not moving. I turn my attention to your breathing. I know you. I know you’re aching for me to caress that spot, to coerce those milky drops from your cock.

I wait a moment longer and then I move that slightest millimeter further and run my finger around the sides of that bulb. You groan, low and sensual, and your legs begin to tremble slightly.

“How does that feel boy?”
“Oooh, good, Mistress. So, so good.”
“Stroke your cock, boy…gently…slowly.”

Your cock is semi-hard. You grasp it and stroke it just as I ordered. Your anus clenches around my finger reflexively. You moan and I increase the pressure on your prostate just a little; your ass clenches even harder.

“Keep stroking your cock, boy. You’re going to release your milk for me, aren’t you, boy?”
“Unnhhhh, I hope so, M-mistress.”

I keep circling and applying slight pressure to your prostate.

“Stroke your cock a bit faster, boy. I don’t want to be doing this all day.”

You obey, your hand pumping faster. Your moans are beautiful. I know that you’re close.

“Mistress? My cock is leaking out the drops, Mistress.”
“Are they landing on the towel?”
“Ohhhhuhhh, yes, Mistress. I feel like I’m going to come, Mistress. May I come, please?”

I ignore your plea for a minute, relishing your sweet torture.

“Ask again, boy.”

Your voice trembles.

“Ahhh, please, please, may I come, Mistress? May your boy come, please?
“You may.”

I continue massaging your prostate and you keep stroking your cock. After a few strokes, you tense and go up on the balls of your feet.

“Ohhh ahhhhh, I’m commming, Miiistresssss!”

You shoot your cum onto the towel as I continue my massaging motions.

“Fuuuuuck, too much, too much…”
“Not enough! Keep stroking, boy!”

You cry out in a mix of pain and pleasure but you stroke yourself dutifully.

“Nothing more is coming out, Mistress, but I feel like I will come again.”
“Then do so, boy!”

Within seconds you’ve come again.

“Any cum this time, boy?”
“No, Mistress.”
“Good. Remove the towel from the bed and then lie down on it.”

You do as you are told on shaky legs. You lie down on your side and I crawl onto the bed, moving to spoon you. I stroke my hands over your body.

“Good boy. You pleased your Mistress very much.”

31 Responses to “Good day for a milking”

  1. Fred Bloggs says:

    Once I realised what was going to happen I don’t think my cock I would be dangling …
    I think I could be tempted to wiggle my ass just to get caned …
    But you have it correct, that’s very good!
    And I think I just discovered another reason to get State side real soon.

  2. Kristi says:

    Ha! Thank you! I’m very glad you enjoyed it. :-)

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  27. A brill post please keep going thanks