A Surprise Milking

I find you reclining on the bed, maybe looking at your phone, but you put it down and look up at me as I come closer. I just got back from work and am still dressed for it--a red turtleneck and a black knee-length skirt and leggings--while you're just laying there in a t-shirt without even underwear on, your cock hanging out loose between your spread legs.

"Is this an invitation?" I ask, but before waiting for a response, I get down on my knees next to you and take your cock in my left hand while reaching under it to try to find your balls with my right. Because of the way they're hanging loose beneath you, I can't see them initially, and wonder how small they are, but when I find them I'm pleased to discover that they are actually quite large and plump, even though they're hanging loose and low.

I kiss your foreskin-covered glans and then reach under your shirt with my left to rub your stomach and nipples while I continue manipulating your balls with my right. When you start to reach down to touch your cock yourself, though, I say "No." firmly while grabbing your arm with my left hand and pulling down on your balls hard with my right.

You start to say that you just wanted to pull back your foreskin and rub your frenulum while I play with you, and I have to remind you, "You know the rules. First, your foreskin is to keep your glans fully covered at all times unless I give you specific permission to retract it, or do so myself. Second, when I'm playing with you, you aren't to touch yourself at all: you're mine, and that means your body is mine to handle as I see fit."

You murmur out a soft "Yes, Miss." and I release your balls. I get up and open the drawer where I keep the ropes for tying you up, and I pick out four short lengths. I begin to tie each of your wrists and ankles to a corner of the bed frame as I continue, "These rules are for your own good, you know. When I found you, you were such an obsessed stroker-boy, constantly playing with your nice, big cock to the point you couldn't focus on your work, or on pleasing a partner."

"Some Mistresses probably would've had you circumcised really tightly, so you couldn't get as much pleasure from masturbating. But I recognized that you have a wonderful foreskin, and I wouldn't want any harm to come to it."

"So, instead, I decided to use your foreskin as a sort of chastity rule: you're never allowed to retract it without permission. After all, you're a horny, big-dicked boy, not a woman with a nice, proper little girldick like I have that stays out of the way unless I get aroused. You need a reminder to keep you from touching your cock all the time, and having your foreskin in place is a good reminder."

With that, I finish the last knot and you stare up at me and whimper a little as you lay spread-eagle on the bed. I kneel at the bedside and return to my previous position, with my left hand reaching for your nipples under your shirt while my right hand grabs hold of your balls and tugs down on them. I place my thumb and pinky on your nipples and start to press down, while my fingertips begin to press into your scrotum and massage the base of your penis through the skin.

You moan a little as I dig my fingers deeper into your scrotum and perineal pouch, moving them in rhythm with the fingers on your nipples. Your cock starts to stiffen a little and I bend my head down to nuzzle it with my nose, but since it's full-length even when flaccid, we don't need to worry about any unauthorized glans exposure. I notice that you're producing a lot of precum from the treatment, but I don't say anything or lick it away, even though it looks tasty.

I let my fingers dig into your nipples as I press harder into your perineal pouch, until your cock starts to twitch a little. "Hmm, looks like you're getting quite excited," I say, "but I don't want you to cum quite yet." I pull my left hand out from under your shirt and release your balls and scrotum as you look at me with a pleading face and mumble "Soon, Miss?"

"Not yet," I say in a slightly comforting voice as I reach down into my purse--I hadn't even managed to put it down after getting back from work before I saw you laying there so invitingly--and pull out the toy that I'd purchased on my way home. I slide it out of the box below the level of the bed, so you can't see what I'm doing, and reach into the same bedside drawer I got the ropes from to retrieve a tube of lube.

I put lube on the toy and bring it up between your legs, keeping my body in the way so you can't get a good look at what I'm doing as I start to kneel over your crotch, brushing my hand on your pubes and cock as I do so.

"You know," I begin, "I to like to make sure you're properly drained of cum on a regular basis. It reduces the risk of prostate cancer, and also makes you less likely to have a relapse into stroking yourself without permission." I squeeze the skin and muscle around your right nipple, digging in with my fingernails, as I continue. "But I'm not sure it's good for you to have orgasms from your genitals all the time: you should be trained to do without them. So I'm going to try something new today."

With this, I look deep into your slightly confused and concerned eyes and touch your outer anal sphincter with the tip of the toy I bought. "You know, I think prostate milking might be a good idea for you"--at this, your eyes go wide--"you can release all the cum you've been storing up without getting orgasmic relief." With this, I press in with the toy and you obediently open enough to let it in.

"I think you'll like the prostate massager I picked out for you, too. It's smaller-diameter than the strap-on I use sometimes: see how easily it slipped in!" I let the massager rest inside you and bring my other hand to touch your cheek and ruffle your hair a little. "Such a good boy!" Then I return my left hand to its position on your nipples while I use the right to adjust the massager until I hear you moan and know I've found the right spot.

I rub your prostate gently at first, but increase force and speed a bit with time, and do the same with my fingers, which are now digging into your nipples a bit with their nails. You struggle a little against the bonds holding your wrists and ankles in place and moan louder, but I comfort you: "There, there. You're almost ready to produce some milk..." and, just as I finish, your cock--foreskin still properly covering the glans--twitches and starts to dribble thick, white cum onto the bed.