Dear Diary – 008 (part 2)

As i lay there, i could hear Mistress searching through the toy box…. the box of pleasure and torment!

“… see how you like a cock in your mouth… sissy”! Mistress then pushed something rubber into my mouth and lifted my head to buckle it tightly into place. I then felt her doing something around the bandages that were binding my thighs “… Oh yeah baby, I’m gonna ride you like a bitch”!

I had no idea what Mistress was up to, but i kinda guessed it with all the verbal clues i was getting… Mistress had placed a double dildo into my mouth, the larger part sticking outwards for the pleasure of Mistress and another dildo was strapped to my thighs.

For the next 40 mins or so Mistress sat on my face, impaling herself on my dildo gag and also impaled herself on the other dildo attached to my thighs. During this riding session, Mistress was constantly tugging on the cain that was pulling on my balls, she teased my cock endlessly… but never too much to bring me to orgasm.

“Look at you… you sissy! How does it feel to be used like this eh?” I lay there in darkness only imagining what delight Mistress must have been having at my expense.

I could imagine how i looked; a grown man dressed in a really girly costume with stockings and high heels, bound to the bed with his testicles being chained and yanked up. His girlfriend mounting a double dildo inserted in his mouth and another on his thigh. I must admit, even in my mind it made a picture! I felt like such a sissy laying there unable to do anything about it and the worst part of the humiliation is that if i could have stopped her… I wouldn’t have!

I just lay there like the good little sissy I am and wriggled and writhed in pleasure and frustration at the same time as Mistress totally used and objectified my bound body. The ‘Male’ part of me joined in with Mistress’s mocking and teasing , making me feel even more of a sissy! What real Man would want to be treated like this?!?

 

Dear Diary – 008 (part 1)

Mistress had that look in her eyes last night… Like she wanted to rip me apart and devour my soul! By the time she was dressed in her stockings, high heels and latex, I wanted to be devoured!

First Mistress led me to the bedroom and had me strip down, I could see the outfit she wanted me to wear already laid out on the bed. Sensing her urgency and need, I quickly got dressed. As soon as i had my outfit on and my heels buckled, Mistress ordered me to stand and bend over.  Applying lube to my anus, she soon slipped in one of my favorite toys… the inflatable butt-plug. After a dozen pumps or so, i was starting to feel really full and then Mistress ordered me to my knees…

“MMmmm, you look soooo cute! Now lick my shoes and show me what a good little sissy you are… that’s it… good girl”!

I knelt there kissing and worshipping her fabulous black patent, drop dead gorgeous heels. I had no idea what she had in mind but she had said that she just wanted to make me helpless and use me abuse me!

Mistress then had me kiss all the way up to her pussy and told me to lick. I buried my head in deep and began licking her, trying my best to bring her to orgasm. However after only about 5 mins or so, she ordered me up and onto the bed. Mistress produced some heavy-duty bandages and first bound my legs and thighs. Then my forearms were bound together up in front of my face, rendering them useless. Once i was bandaged into place and totally helpless, Mistress then produced the parachute for my balls.

Firmly in place, the chain was then stretched and attached to the bottom of the bed, pulling my balls into a slightly uncomfortable but slightly erotic position. Mistress then placed a blindfold over my eyes, leaving me in total darkness. I could feel my heart start to race as my mind wondered at what might lay in store for me now. As i lay there bound, helpless and blind, knowing that Mistress simply wanted to use and abuse me… i kept seeing that hungry look in her eyes in the back of my mind!

Dear Diary 005

When we returned from No Mercy Manor… Mistress still had plans in store for me!

We embraced and snogged passionately as soon as we were home… still dressed from the party, we still felt really into our roles. I was ordered to make Mistress a cup of tea and a slice of toast. While mistress sat and ate, I was told to kneel at her feet and worship her shoes, then take them off and give her another foot massage.

I knelt there, obediently rubbing her feet as she finished her drink… then she opened her legs, slid her panties to the side and ordered to me lick her to orgasm. I knelt in closer and buried my head into her pussy and began flicking her clit with my tongue. It wasn’t long before Mistress was pulling my head deeper into her and telling me to suck. I was getting as horny as Mistress was and felt her nearing orgasm.

I licked and sucked for all i was worth until finally Mistress’s moans of orgasm came. Not content with just one orgasm, Mistress wanted me to carry on and so i spent another 20 mins or so buried in her pussy, bringing her one orgasm after another. Finally, Mistress pulled my head on to her lap and just lay there in that post-orgasmic state, stroking my head and face.

I just lay there and relaxed into her… her energy flowing through me… After what seemed just a moment, but was really a while later, Mistress ordered me to the bedroom. My wrists were cuffed to the top corners of the bed and my ankles were cuffed and brought upwards to clip onto the top corners also, leaving me on my back and my legs up on the headboard with my arms!

Pulling out the toy box from under the bed i saw her put various anal toys on the bed. Mistress slid a towel under my ass and began rubbing lube into my hole with her finger. Then came the inflatable butt plug, I was inflated and deflated a few times, bringing me to a critical balance of pain and pleasure. Next came a dildo, which she eased gently into me. Once she had it all the way in she began to fuck me slowly with it. By now I was just lay there, feeling totally helpless and at her mercy. My legs were uncomfortable but the pleasure from the dildo was distracting me nicely.

I writhed in pleasure at her expert hands, yet a little part of me was laying there mocking myself at the absurdity of all this! Here i was, a Man, on my back taking it up the ass from my girlfriend! What kind of a man was I? Dressed like a girl and made up like a girl and taking it like a girl!?! The humiliation of those thoughts should have snapped me right out of my pleasurable bubble that i was floating in, but they didn’t, they only fuelled the fantasy of it all even more and further enhanced my submissive sissy feelings!

Then Mistress, pulled out an even larger dildo and began to pound me with it. I had mentioned my interests in fucking machines and Mistress remembered this and as she furiously pounded my ass, leaving me moaning like a girl, she began to tease me…

” I bet this is what it feels like to be fucked by a fucking machine, isn’t it sissy? Mmmm, i bet you like that don’t you” Mistress increased the speed of which she was pounding me and all i could do was lay there and take it. A part of me was loving it and another part of me was finding all very humiliating!

Dear Diary 004 – No Mercy Manor

This weekend was the fetish night at ‘No Mercy Manor’. It’s always a great place to meet up with other friends and kinksters on the scene and also proved to be a great venue for Mistress Marie to show off her new ‘sissy’!

Mistress looked absolutely stunning that night… showing off her sexy legs in those stockings and über sexy black high heels that i bought her for Christmas. I was dressed in a baby blue latex dress and baby blue heels.

My evening began with me being cuffed and tied to the large bamboo pentagram that you see in the photo…

Mistress informed me that I wasn’t being punished… she was just ‘gonna have some fun’ and was going to demonstrate her status and power over me by whipping and caning me in front of all the other people in the club. Before Mistress began, she whispered into my ear that she wanted me to be a good sissy and not moan or scream or wriggle about!

I clung to the sturdy frame hoping i would not let her down! This was the first public event we had gone to in our new roles and i really wanted to try my best to please Mistress and make her proud of me.

Luckily Mistress began lightly, working up to a more intense phase a bit later on. As i lay there helpless, against the frame being repeatedly whipped, i could not help but see myself from the point of view that the other clubbers must have seen. I know that to the casual observer it must seem absurd to watch a guy dressed as a girl allowing himself to be bound and whipped by his gorgeous Girlfriend… but to me it just felt sooo right!

Mistress ended her demonstration with the cane! I hate the cane and Mistress knows it only too well… “I’m going to give you six strokes now sissy and I want you to count each one aloud and thank me for it”

I whined like a little girl and replied as sincerely as i could muster “Yes Mistress!”

I took the six strokes and managed to count them out and thank her too! This was impressive even by my standards and Mistress let me know that she was proud of me too! Mistress let me lay against the frame recovering as she ran her long red nails up and down my back, scratching at my skin while whispering sweet sissy sentiments into my ears.

Later on in the evening, after one drink too many and the erotic sight of my beautiful and gorgeous Mistress, I could not help myself but to keep mauling her like a puppy. Mistress was not happy with this behaviour at all…. especially without permission and warned me to stop touching without permission. I managed to remember for all of about two minutes and once again started to stroke her stockinged legs and run my hands over her soft breasts… Big Mistake!

Right there in front of all the guests at our table, Mistress ordered me to kneel over her lap. I wasn’t sure if she was actually being serious at first, but when i looked her dead in the eyes, i knew she meant it. I stood there for a moment, doing my best puppy dog eyes impression, before Mistress stated clearly… “Now!” I leant over her knee and was embarrassed even further as she raised my skirt and began spanking me like a naughty school girl!

As her hand slapped away at my ass her lecture began… ” How….. many…… times….. have …. I told you…… not…… to…… touch….. without……. permission….. you naughty….. naughty…. sissy” by the end of her lecture and spanking, i was apologising profusely and was genuinely feeling a bit humbled and humiliated by it all.

“Now, if you want something to touch and stroke you can get on your knees and massage my feet as a way of making it up to me, can’t you sissy”?

Chastised and wanting to get back in Mistress’s good books i replied a very sincere…”Yes Mistress”. I dropped to my knees, barely able to look into the eyes of the other people at the table. I slipped Mistress’s shoe of one by one and gave her the massage she deserved. Knelt there, with my bum still stinging, i really did feel like a sissy! Humbled, humiliated and serving at the feet of my awesome Mistress!

Dear Diary – 003 (part2)

While i stood there in the shower getting all clean and smooth for my Mistress, I thought about how easy it was for me to slip into ‘sub-space’ or ‘sissy-space’ even. It’s a part of me that i have always kinda kept locked up and hidden and now Mistress had a key to it. That excited more than anything, but also gave me butterflies too!

After my shower, Mistress sat me down and applied make-up and found a me cute little pixie wig to wear.  I then put on my black nylon seamed stockings and heels and had to put on the short pvc maids dress that Mistress seems to like me in… then i was lead to the front room.

First Mistress cuffed my wrists behind my back and cuffed my ankles to the spreader bar. Then had me bend over while she inserted the inflatable butt plug. After inflating it a bit, Mistress then placed a ball stretcher ‘parachute’ to my balls and pulling tightly, fastened it to the spreader bar. Inflating me a little more and testing the tension on my balls… mistress placed a two penny piece on the door and told me hold it in place!

“Now sissy… For your punishment, I want you to hold this in place until i tell you otherwise” My offence was masturbating without permission… again!

Mistress then jiggled the chain pulling at my balls and inflated me even more, making me move around in a mixture of pain and pleasure. I dropped the coin a couple of times while my head steadied itself and as punishment, tasted Mistress’s favorite crop as punishment.

Standing there, trying my best to hold the coin against the door while my balls were being pulled and my ass inflated to the point where is was both pleasurable and uncomfortable, was maddening!

Mistress began teasing me again… “look at you sissy! it looks like you are actually enjoying this, aren’t you? Its suppose to be a punishment you know, not a reward”!

Mistress struck my ass with her crop a few more times and inflated me even more. When i dropped the coin again, mistress lifted my skirt up and started to crop the end of my cock! I hate this, but my cock seems to love it and responds by swelling to maximize the pain even further!

After a few more tugs at my balls Mistress once again put the coin up against the door and told me sternly not to drop it again or else! My body was already shaking and my legs were like jelly and all I could do in my sorry state was put my whole face up against the door to ensure i did not drop the coin. I stood there shaking and groaning as my balls were aching from all the pulling and my ass was making me gyrate in discomfort and pleasure. Eventually, all the stimulation, pleasure, pain and frustration made my jelly like legs really wobble and i dropped the coin again. I felt the sting of the crop before i heard the coin hit the floor! The pain focused my attention away from all the other torments on to the line of fire. Mistress then teased, tortured and tormented me a while more, mixing pleasure and pain, before getting me to sit down on a chair in the middle of the room…

Mistress vanished briefly allowing me time to catch my breath and try to steady my mind, Mistress then returned with the chastity device and had it securely in place before my cock started to swell again…

Dear Diary – 003 (part1)

Well, a lot happened last night! So much so, that i am still trying to process it all.

Mistress Marie arrived wearing her sexy leather boots and catsuit! Mistress had a coat over the catsuit and got a few looks at the petrol station on the way over! So once her coat was off, Mistress was already in the role… The evening began with Mistress stripping me naked and chaining me inside the shower cubicle.

Standing there naked with my toe nails painted a bright pretty pink and chained to the shower piping with Mistress cat-suited and booted felt hot. I felt so vulnerable and exposed and well, naked, standing there shivering a little from the cold.

Mistress Marie then filled the enema bag and hung it from the shower railing. Then she inserted the nozzle up into my ass and turned the flow on. All i could do was stand there and let it happen. As the bag slowly drained and started filling me up i could feel my stomach starting to murmur. Mistress just stood there looking really hot, highly amused with her ‘handiwork’ and basking in my obvious discomfort.

To make matters worse, Mistress then began dragging her nails slowly down my back, twisting at my nipples and biting deeply on my neck. Occasionally Mistress would spank my arse or ‘her’ cock and even grab and yank my balls uncomfortably downwards. Despite my predicament of being chained up and my stomach slowly bloating from the enema bag, my cock was oozing pre-cum.

Mistress eased back on the teasing again and stood back to admire her dribbling sissy in the shower. When the bag was empty, Mistress removed it and told me to hold it all in for a while… again she stood back and basked in my discomfort and obvious pleasure from her teasing and torment. I love the way Mistress is able to push my buttons and in no time at all, can have me a frustrated dribbling mess just begging for more!

After standing there teasing and mocking me for a while and occasionally laughing at my sorry state, Mistress went to get the keys for the chains and padlocks. Once unchained I was then allowed to finally empty myself. Mistress even managed to make this more embarrassing as she stood and watched me empty myself for a short while!

After emptying myself, I was ordered to get a shower and make sure i was all clean and smooth everywhere!

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!