Learning my place in the relationship

Monday morning had arrived and my diaper was full, Mistress was very pleased as she removed it and put my chastity device back on for the day. “Good boy” she cooed again, “Im very proud of you, you need to do that everytime your in your diaper, soon you won’t be using toilets anymore once I figure out what kind of daytime diaper to buy for you so you can wear them to work”.  Well that’s some great news to start your day huh? She told me she would be home around five, left me no specific instructions other than I had to plug myself as soon as I go home, and keep it in until she took it out.  I got home a few hours before she did, plugged myself with the medium plug and laid down to take

a nap with my panties holding it in place (she threw away all of my boxers). I woke up an hour later with the strange urge to want to make her proud; I quickly cleaned the whole house then returned to her bathroom. Suddenly I got the idea of wanting to make her proud again, so I attempted to plug myself with her largest plug to better prepare my “hole”. I had no luck getting it in, so I began to look at other ways to get ready. She had made it pretty obvious she would be “fucking me” tonight, I knew even though I hated being plugged, it would make sex a lot easier for me…the lesser of two evils? She had told me get out her largest dildo for her harness “King Kong” is its nick name. It’s 7 inches long and a few inches around, it’s a really good size, though I know she’ll be getting larger ones as my training progresses. I attempted to stick King Kong inside me to see how bad it hurt; pretty bad was the outcome, though I knew I would survive.

When she got home she immediately checked to make sure I was plugged, satisfied we sat down and ate dinner, which followed by a surprise for me. She led me into the bathroom and explained it was time for me to lose all of my body hair. I literally got sick at the thought, I’m a guy, my legs have hair…my chest has hair…my ass, well you get the pattern. She then covered everything in Veet, I couldn’t believe she was making me hairless! It didn’t really hit me until she began scraping it off with the tool. What lied underneath was smooth skin, for the first time in my remembering life. I was shocked. “Sissies aren’t hairy, you have to be sexy, your arm pits are soon”. I really couldn’t comment much, I think this really hit me that she was very serious about feminizing me as much as she could. She had joked about getting me fake silicone breast which glue on, I never took those comments serious until now. “You’ve always had a great ass, but damn it looks good now”. She continued to compliment her work. I looked at my reflection in the mirror “From the back down, from behind you look like a freaking girl!” I thought silently to myself, you have no hair, your wearing a thong, your ass is showing off a pink plug…what have you gotten yourself into.

“You look so sexy, get on the bed now” she firmly stated. After applying lotion to my new skin, she attached my ankle cuffs to a small 14inch spreader bar, then attached my cuffed wrist to the middle of the bar; I was laying on my back “Hog tied” if you will. Wrapping her hands around my thighs she pulled to the edge of the bed, so she could have full access to her “sissy hole” as she continued to call it.” Removing the plug she blind folded me and asked if I was ready. Explaining how she was not going to gag me this time because she may want some of my feedback. Looking back I wish she would have. She positioned herself in front of my rear, I could hear the lube spreading before she entered me. I realized she wasn’t using “King Kong” rather a smaller dildo, about the size of my actual cock. I failed to mention she removed the chastity device as well.

About two minutes into her being inside me, she began to pick up the pace, and all the while grabbing my cock and stroking me rhythmically while she continued to pound me. I was lost in a see of pleasure, it began to feel so good, I didn’t understand the feelings. Granted I’m horny as all get out despite the fact its only been five days. She continued, “Does this feel good”

“Uh…huh” was all I could stumble to get out.

“Do you want to get off?”

“Yes please” I said.

“Do you like me fucking you”

“Yes I do, can I please get off??!!”

“No.” she said calmy.

Then I made my fatal mistake, I tried to top from the bottom…a big no no. I started begging for anything, even a ruined orgasm. She poured more lube on my cock and got a little too much; she noticed it but I made the mistake of telling her she messed up. Right there she pulled out of me, said alright that’s enough… “You just couldn’t shut up and now it cost you, into the shower, then into your diaper and off to bed”.

I was so freaking mad! Then it started to hit me “You just got made because she wouldn’t jack you off while SHE was fucking YOU”. “That felt somewhat good???” What’s happening to me?

Tuesday was uneventful, typical chores and hypnosis files followed by another evening of me in a soggy diaper. Falling asleep with my face in her ass (which I don’t mind, she has a perfect ass, I mean perfect) she reminded me to plug myself when I get home Wednesday afternoon. I know she’s going to get the strap on out again. I just can’t grasp…am I looking forward to it? Or dreading it? We’ll see tonight…

Sissy Debbie