Dear Diary – 002

Well since signing the ‘Sissy Contract’ last week, I have been pretty horny and really pre-occupied with femdom / sissy related stuff. This kinda led to me breaking one of the rules in the contract…. “No masturbating without permission”.

Well yesterday Mistress came over to settle the account and give me another taste of what being her sissy meant.

Mistress had me wear the cute little polka dot sissy dress you see in the picture, with some white lacy stockings and black patent mary-jane heels. Then she attached a pink collar with pink wrist cuffs attached. Once again i found myself kneeling between Mistress’s legs using my tongue to bring her to orgasm. I love being dressed like a total sissy on my knees worshipping my Mistress!

Then i was taken to the bedroom where i was to be punished for being a ‘naughty sissy’. I begged and pleaded that Mistress would not punish me too harshly as it was our first proper punishment session… thankfully, at least for this time, she did take it easier on me than i deserved.

With my legs spread wide in the spreader bar, trying to keep balanced in my heels, i was pushed forward on the bed and the short chains attaching my wrists to my collar were only just long enough to put my hands on the bed to support me. Mistress had me beg to be punished!

“I have been a naughty sissy Mistress, please punish me Mistress…” Mistress had put the mirror in front of me as well so i could watch my humiliation and punishment as it happened. The hard wooden paddle was not forgiving and the first stroke took us both by surprise. I struggled throughout the six strokes, but was able to maintain my composure. Mistress thought that i had taken it well and caressed me telling me that I had been a good sissy 🙂

Then, leaving me bent over, bound and unable to rub my stinging rear, Mistress lubed up the inflatable butt-plug and gently slipped it into my ass. After inflating me, Mistress unbuckled my ankle cuffs from the spreader bar and had me kneel and kiss her feet. kneeling there, kissing her feet with my ass inflated, was quite horny and also humbling. It does help to re-enforce the dynamic as me as her submissive sissy and Mistress as the one on charge and the one to be worshipped, for kneeling there, i really did start to feel a bit like a ‘sissy’!

After kissing her feet and licking her to orgasm a few more times… Mistress attached the spreader bar again and bent me back over the bed. I watched Mistress fasten on her strap-on and start to lube it up, all the time telling me that she was gonna fuck her sissy!

The deflated plug came out quite easy after i had been stretched out a bit. Mistress eased the dildo in and slowly started to work it in and out. It wasn’t long before Mistress was pounding away at me telling me ‘what a sissy i was’ and that ‘i was her sissy bitch’. All the time i was watching myself getting fucked and also watching Mistress fuck me in the mirror!

After Mistress had had a few orgasms, my cock was aching for some stimulation, as watching myself getting fucked like this was pretty fuckin horny. Mistress told me i had to beg for the pleasure! so i begged for the privilege of playing with my cock as i was getting fucked in the ass! It wasn’t too long after that that I exploded into orgasm, with annoyed Mistress as i hadn’t asked permission to come.

Mistress left me there bent over as she removed the strap-on and cleaned herself up. I was left to look at my reflection in the mirror as the euphoric high was slowly being replaced with the cold hard reality of it all.  Oh the shame of it! but then that would make me horny again, then i would feel ashamed that i was getting horny over feeling ashamed! Wow! what a mind trip!