I just finished milking Reg for the first time and it went fairly well. With him on all fours and panties at his knees I put my rubber glove on then applied lube to his anus. I worked my fingers in to find the prostate. I bought this small vibrator not much bigger than my finger but longer. When I inserted it then turned on the power setting Reg trembled a few times. I pulled his cage and all between his legs and massaged his balls up and down while letting the vibrator do it thing. In a few minutes sperm started dripping so I turned up the vibrator causing Reg to move again.
That was a better setting as I massaged his balls the sperm started squirting then stopped then squirted again. A few minutes later it all stopped with about an ounce in the cup. I thought that was pretty good for a first time. Reg didn't feel the sperm coming out so no pleasure and no pain. He did say it was a little uncomfortable but it didn't hurt. When I showed him the sperm he was surprised that he didn't feel like cumming at all. I let Reg know I liked doing that and especially knowing it was good for him. I left Reg there for a minute the came back with my strapon already with lube on it.
With Reg on all fours I spread his legs more and gave him a pillow for his head. I let him know I had my strapon ready so he was to remain in that position. All Reg said to me was please don't Janice which is when I inserted the head into him. I had to tell Reg to stay still twice so the next time I slapped his ass hard. Having his attention I started to fuck him slowly and not very deep at all. You would think I was killing him with the sounds coming out of his mouth.
Using a small dildo has its benefits allowing me to go further with each pump. Before long I was fucking Reg slow and steady with him begging me to stop. Helga if you saw the dildo you would laugh at him crying over a 6" skinny penis.
I stopped pulling it out slowly with Reg thanking me for stopping. It was clear to me he was faking it but that is okay when I buy a larger dildo I won't be stopping. I said to Reg he should feel pretty good having been milked and fucked in the same night.
Somehow he was laughing with me. I gave him a hug telling him I was proud of him for a first time. He then let me know he didn't want that anymore. There was no way I was backing down So I reminded him I am the Mistress and I decide when he gets fucked.
When I heard yes Mistress Janice I knew my point was received loud and clear.
Thanks a bunch,
Thank you for your letter Janice. Great to hear, it is a necessary task, owning a sissymaid does come with a few responsibilities, not many, but good health is one. Of course being milked is humiliating for them, well, now many things will be, so that doesn't matter all that much. One fun thing I might suggest is that you place a mirror in front of him if you can so you can see his face while being milked and being pounded, it can be a real turn on to see his expressions, the other thing is, he can see himself being controlled. A pretty photo of you might do as an option.
He didn't want you to do this again, pretty funny, he seems to be under some form of delusional thinking he has a say in any of this. A good strong pegging will disabuse him of that notion toot sweet.