A Cryptic Enigma Christma Carol

i tried so hard

deep rollin

Dear Helga,

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,
Janice

oneeyedwilly25

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