The milking fetish seems to be slowly becoming more popular as of late. Which is good for me as I love it in every sense :D
If it's a woman with large breasts being milked or a man being milked it's all good :) something about it is delicious ;)
Most ideas have been covered (if only once);
There's a file where your testicles grow and you can't stand (only on all 4s), when your cock is squeezed you cum uncontrollably and it doesn't stop until they do. Focused on the pleasure until your taken to a milk farm where you are raped by a machine milked hard for hours.
There's a file which changes you into a woman that has an almost bimbo personality where the only focus is on her larger and full breasts, they feel full and keep filling until the slightest touch causes them to lactate milk. Then when the happy mindless cowgirl gets milked the process is like orgasming consistently.
Now to my point;
Why not fuse the two into a long trance? Have a start where the man is brought to a small room with a nice chair, as you sit down your given a gentle inducer that takes you into a normal trance. Then after this you are given a glass of milk and you find your mind going fuzzy and your body begins to morph into that of a slender woman with a strong back and large breasts that keep filling with milk (and drain the persons thoughts) until it is like a balloon pushing to its limits. Sore and swollen (and because the person is focused on the breasts the subtler changes can be made to the body (ie slimmer legs, squishier ass, hair loss, etc but not the pussy just yet and the cock stays). Then the person trancing you comes over and brings a bucket and begins to tease your breasts so you can tell just how overly sensitive they are.
Then the person begins to squeeze and the milk comes out and the subjects mind is being squeezed out more and more, even finding them mooing in pleasure (as the milk flowing from their breasts will be a mental orgasm). Then afterwards they are left to lie back and relax and then take them down even deeper into trance, continual as the cow breasts grow again with milk and what little consciousness is there flows there.
The tist comes over after setting down the full bucket and takes the cow's hand taking her to a hidden corridor behind the bookcase, past doors with simple numbers on, then he leads you into a room which has only a metal table the same shape and size as a massage table but with 3 holes, 2 for the breasts to hang through and 1 for the penis.
As soon as the cow lies breast down on it and they feel the penis being gripped by the table (similar to a fleshlight toy), then feeling the tist attach two suckers to the breasts. The machine begins to suck the breasts dry continually taking all the mind and thought, it begins to suck and massage the penis to force the physical pleasure to match the mental pleasure (that causes the cow to lose their mind). It will carry on and the machine could possibly lock the neck, ankles and wrists to the table so it could literally continue for at least 15mins (ie the track would actually continue even on loop at this part), not stopping. When the 15mins are up the cow will feel a tingle below the cock where the balls are (soon to be were) and the tist describes the pussy forming where the balls were (not effecting the cock mind just making it even more hard even so hard its sore), then feeling a dildo slipping into the new pussy fucking hard (the cock is effectively now a giant clit), the pleasure will be too intense and the cow will pass out (if you continue to fuck someone unconscious they will stay up so it would be a challenge at this part but do-able).
Then the subject awakens (after a gentle while to calm) in the original chair to the tist asking them if they need a glass of milk.
;)