One boring October evening I was scrolling the internet looking for ways to earn some extra cash prior to the holiday season. I happened upon an ad that stated I would be paid for testing out a "milking machine" designed for the sake of draining prostate fluid/semen from males for various purposes. This sounded intriguing and like a chill side gig. I was also excited to see that they'd pay me $500 per milking session. I was sold. I contacted the number on the ad and set up my appointment.
The next day, after work, I arrived my testing appointment just before 5pm. I was greeted by a nurse and was told to fill out some privacy forms and other health questions. Upon completing these, I was soon taken back to the milking room. Here, the nurse told me to strip completely naked to which I did on command. Here I stood completely naked and semi erect in front of her. I then slipped on my wig. She then told me to lay down on the milking bed, which I did. She then strapped my legs down with straps and then strapped my arms down as well. I was securely nestled in these straps and couldn't escape if I tried. This vulnerability got my dick fully erect.
She smiled and said "good boy". She then told me she was going to go get the guys who will be conducting the milking and told me to hang tight. As if I could go anywhere.
A couple of minutes later, two guys walk in. Both roughly 6 feet tall with muscular frames from what I could tell. Both fully clothed in normal casual wear. The first guy introduced himself as Randy, he appeared to be Puerto Rican with very masculine facial features, clean shaven, with dark curly hair. The second guy, Charles, appeared to be from somewhere in the middle east and had a trimmed and well defined goatee.
Randy placed a milking device over my penis that resembled a glass penis pump that was connected to a glass canister via a suction tube. This felt freaking good. Charles then lubed my asshole and placed an aneros vice 2 prostate massager inside. Both the milker and the prostate massager were turned on to full power.