Digital rectal insertion plus VR headset

"Excellent, that's all we need. Well, then if you'll follow me." She gets up from the desk and leads you into the back. You're given a brisk medical exam, including having your height, weight, and penis length (both limp and fully erect at Alice's hand) measured and entered into a database. Your clothes are taken from you, and you're led down a short hallway through a door marked MILKING ROOM 1.

It's a small room, with the same calming blue walls and soft light as the rest of the milking salon. The middle of the room is taken up by what must be the milking table, a flat, cushioned black piece of furniture with an obvious hole in the middle.

"Here we are," Alice tells you. "Your attendants today are Marisa and Ella. You can have a seat there," she motions to a chair set along the far wall you hadn't noticed, staring at the milking table.

Alice leaves and you walk over to the chair, taking a seat and trying not to fidget. You almost jump out of your skin a moment later as two more attendants walk in, the white nametags clipped to their blue scrubs identifying them as MARISA and ELLA.

You examine Marisa first. She's tall, tan, and curvy, her dark brown hair up in a bun with tendrils hanging on each side. It's not easy to tell under the scrubs, but she looks pretty fit. She has dark features, large eyes and full lips in a round face. She's smiling at you, a friendly gesture that settles your nerves a little even as you jump up out of the chair, covering your genitals with both hands reflexively.

This draws a little laugh from the other attendant, Ella. She’s short and slim, with pale skin, her blonde hair in a short pixie cut. She has on stylish half-frame glasses, her merry green eyes sparking behind the lenses.

"Hello, sir," Marisa greets you, her voice soft and deep, glancing down at the tablet she has in her left hand. "I'll be your milking attendant for today. Let’s see… the VR headset? And digital rectal insertion. Ella will be handling that. Go ahead and hop up on the table and we'll get started."

She gets you up and lying chest-down on the table, your limp cock hanging through the hole. The collection device must be under there, your cock stirring a little thinking about what's about to happen.

"I'm going to put the headset on you now," Marisa tells you. Your vision goes dark as she fits the unit over your face and tightens up the straps. You almost jump out of your skin as she turns it on and in front of your vision appears two 3D anime catgirls.

Instead of the sensible blue scrubs of the human attendants, these women are wearing white and pink sexy nurse outfits - basically a super short dress, cut very low on their huge breasts and high on their thick thighs. They have a perfect hourglass shape with exaggerated curves, long pink hair down to their shoulders with pink furry cat ears, and most arresting of all bright pink eyes, two sets of them staring right into yours through the headset.

"Nyaaaaaa~!" they squeal, her high voices loud in the headphones. "Hello, sir! We’re Cleo, your virtual attendants. We’re here to help you relax and produce a lot of man milk! In just a moment, the milking procedure will begin. We’ll be here to help you the whole way!"

You're not sure what you were expecting with the VR headset - regular porn? a video of a guy getting a handjob? - but this isn't it. Well, it's too late to go back now.

"Sir!" the Cleos chirp. "Your attendants have indicated they are ready to begin the milking procedure!" Sure enough, you feel warm, lubed fingertips beginning to tease your half-hard cock. In the back, your buttcheeks are gently pried apart, and someone begins spreading a large amount of cool, slick lube in your back door.

The view on the headset shifts; where before both Cleos had been hovering in a white void, a perfect re-creation of Milking Room 1 fades into view. One Cleo is now seated on a low stool on your right hand side, existing in VR exactly where Marisa is in reality. You turn your head enough to see that the other Cleo is behind you, no doubt in Ella’s position.

The VR attendant’s movements match up with exactly what you’re feeling - even knowing you're wearing a VR headset, it's easy to imagine that Cleo is the one teasing your cock and fingering your asshole.

“Wow, you’re so big,” the catgirl on your right purrs as the hand on your cock changes to a strong milking motion. You get the feeling Cleo says this to all the men, but it feels good to hear anyway. You open your mouth to say thanks, but instead let out a deep moan as the one in back begins aggressively fingering your ass, insistently pressing the tip of her finger against your prostate.

"Does it feel good?" one of the Cleos purrs. You gasp back a yes, so far into the simulation you don't even consider what Marisa or Ella must think of only hearing your side of the conversation.

You feel another hand, this one on your balls, gently kneading them as her right hand continues stroking your cock. It feels so good, in fact, that in no time at all you realize you’re about to finish. Just the two hands working your cock and balls are enough, but the one rubbing your prostate is the real killer blow, a hot jolt of pleasure shooting up your spine each time.

"Gonna cum," you grunt.

"Oh, very good, sir," the Cleo on the right winks at you. "Let's see how much man milk you can give me, okay?"

"Yeah," you moan as it becomes too much. "Yeah - I - oh shit - fuck!" you howl, your hips weakly thrusting down as you finish. The soft hand around your cock continues expertly milking you as you ejaculate straight down, humping the milking table as you unleash spurt after spurt. Each time you move your hips back up, your prostate rubs against the other Cleo’s finger.

"That's it," Cleo eggs you on. "What a good boy! You came so much!"

Post-orgasm her hands go from divine bliss to an uncomfortable overstimulation, and you have to stop yourself from squirming. She doesn't let you go soft, using just the tips of her fingers to keep you hard. The other Cleo doesn’t remove her finger, but she does stop moving it, just resting the tip against your prostate.

“He just needs a minute,” the rear Cleo tells the one seated to your right smugly. “I could make him cum just from this.”

“Oh, stop it,” the other Cleo breezes back. “We need his balls completely empty, and that means using all our weapons on him!”

“Yeah, yeah,” rear Cleo giggles, jabbing her finger forward. You cry out, your cock hardening in the other Cleo’s hand. “Ready for round two, Cleo?”

“Ready, Cleo!”

The catgirls attack you again. The one on the right keeps talking to you: “We need all of that man milk, sir, so no complaining! Three more to go, sir!”

The second climax comes on only a little slower than the first. There's no clock in the room, but you feel like it's under 60 seconds before you feel yourself getting close again. The hand on your cock speeds up, the one kneading your balls harder and more insistent. The finger up your ass now has just the tip moving, aggressively mashing against your prostate.

"Here we go again," Cleo purrs. "I want another big one from you! Show me how much you can cum!"

It’s too much. You cum again, hips bucking weakly against the table, emptying your balls straight down into the unseen collection device. You savor your orgasm as long as you can, three hands sending you to heaven for a few wonderful moments as you cum and cum.

"Don't even think we're done yet," Cleo tells you sternly, seeming to sense your thoughts. "You have two more to go, sir. You know, I'm really not asking much of you. All you need to do is lay there and cum, you know? I don't want to hear any complaining. In fact, why don't you say, 'Thank you Cleo'?"

"Thank you Cleo," you mumble, far past the point of embarrassment or wondering what Marisa and Ella are making of this. Cleo seems pleased, at least, grinning at you and purring.

“Hey, what about me?” the Cleo behind you demands.

“Thank you Cleo,” you mumble to her.

“That’s better,” she purrs. “Well, now it’s time for number three!”

You're not sure you're ready, but she's proven right as your cock begins to beg for more. The one on your right switches back to her milking grip, applying faster, rougher stimulation. Having cum twice, it takes a little bit longer to get close to number three, but getting there is never in doubt.

"Here we go, sir," one of the Cleos announces as you feel yourself getting close. "I know you must be tired, but I want another big one from you. You aren't allowed to leave here with anything left in those balls, do you hear me?"

"Uhhhhhhh," you moan back, the pleasure crowding out any higher thought. "Fuck!"

"I'll count it down for you. Five, four, three, two, one - cum!"

You climax on command with what little you have left, managing a half dozen weak spurts as the hand on your cock does its best to milk every last drop out of you, the one in back expertly rubbing your prostate generating so much sensation you’re not sure you’re ever going to be able to cum without it again.

The discomfort after you're finished this time is the worst yet, and you can't imagine you have anything left to give. You're considering saying you want to stop, but once again Cleo seems to know exactly what's going through your mind.

"Just one more," she orders you, kindly but firmly. "I know my brave boy can manage one more, can't he? That's right. You just let us handle everything."

In the end, you're too tired to get up, just moaning into the table as the Cleos continue working you. This time when the milking Cleo switches back to her main grip, it's as fast and as hard as you've ever experienced. The other Cleo matches her pace, ruthlessly fucking your ass with her finger, stopping for a second at the end of every stroke to hammer your prostate like an angry woman hammering a doorbell.

The stimulation is so strong it's almost uncomfortable, and you writhe on the table, gasping and hammering it with your fists as the Cleo’s hands bring you to number four.

"Last one!" both Cleos chants as you cum, feeling like you're shooting dust, not sure if anything is even coming out. "Last one! Last one!" Your cock spasms weakly, drawing fiercely on the empty well of your balls. When you're finished, the hands finally leave your cock, leaving you a sweaty mess on the table.

You just lay there trying to catch your breath as both Cleos bids you farewell: "That concludes today's service, sir! I hope to see you again soon!" They blow you a kiss and vanish a second before the VR headset is removed.

Marisa and Ella have disposed of their gloves, and Marisa helps you off the table. With a smile she tells you that you'll be paid up front, and you wave away her offer of helping you back to the changing room, holding on to a little shred of pride as you manage to hobble out of the milking room, back to the changing room where you get dressed.

You head to the front desk where Alice is waiting for you: "Oh, sir! I hope you were satisfied with our service today. Just a moment and I'll add up your payment for today." She stares intently at her screen, adding up your results. "There we are. Congratulations, you've earned $100!"

Not bad! You take the five crisp $20 she hands you and stick them in your pocket. With a smile she tells you to come back any time. You leave to go home, your head clear and your money problems a little less, even if you feel like your ass is going to be sore tomorrow.