Sissy Maid

He arrived in a grey suit to which he told me he was wearing panties and stocking underneath. He apparently does this look often. I’m into it. I made him strip out of the suit. I want to see what I’m working with. The suit removal did in fact reveal pink lace panties and pink thigh highs. I ordered her to dance for me after all her job is to keep me entertained. She brought with her an adorable maid’s outfit and black pumps. I had her put them on. The transformation into my sissy maid had begun. First order of business was to clean and shine my boots with her tongue. I then removed my boots and allowed her to worship my feet. I am always in the mood for a foot massage. I will say she did not disappoint with the foot rub. I then handed her a pink feather duster and go around the room and dust the shelving and the toys. She did a good job of that as well. It’s always nice when a sissy maid takes their job seriously.

After the cleaning and foot worship I wanted to reward my maid. I tied her to the bondage bed, lifted up her skirt and shoved in a butt plug. I decided I wanted to use a bit of electro on her clit. Once the pads were attached, I sat on the maid’s face. As I cranked up the electro I began smothering her with my ass. I enjoy turning up the potency of the electro while sitting my ass more firmly on their face causing more suffocation.

I put on my strap on on and let this bitch out of bondage. This maid loves cock so I had her suck mine of course. I picked a cock similar to the one I sucked that morning which was pretty substantial. I told her this and that she would now need to impress me. This slave again did a very good job, particularly the skull fucking and licking my balls. From here I bent her over the bondage bed and began the pegging and hair pulling. After a fierce round of who’s your daddy, I made her get on her knees. I allowed the slave to touch her clit as she sucked my dick. When she came I made her rub the cum on my cock and suck every last drop off.

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Naughty thoughts

A potential slave contacted me to be punished. He stated he was having inappropriate thoughts about me. His fantasies included fucking me as well as other depravities, thoughts he was now regretting. He felt he disrespected me and needed atonement for his disobedience. I was extremely pleased he was aware of his vile nature and was now ready to take his punishment.

When he arrived he told me how beautiful I was and how utterly terrible he felt for having these fantasies about me. I had him take all of his clothing off then kneel at my feet to lick my boots. This was where he belonged at my feet under my control. My boots would be the only thing he would be licking. I ordered him to the CBT chair where is sat spread eagle. I locked his wrists and ankles to the chair. I began playfully kicking his cock and balls. I put clamps on his nipples. I picked up a flogger and flogged his inner thighs, dick and balls. Once he was nice and red I moved on to my single tail. Nice cracking sounds leaving welts and red lines all over his cock and stomach. I told him this is what he deserved for having such thoughts about me. I would never allow him to fuck me as he is beneath me. He would now only be able to suffer for me to be in my presence. I tied his dick up and began adding clothes pins. When I was finished there were clothespins around the head of his dick, up and down the sides of his cock and a few on each of his ball sacks. This is when I like to take the vibrator to the head of their dick. It’s quite an intense feeling I have been told and was again told that on this occasion. I alternated between this and pulling on the chain of the nipple clamps he was wearing. When I finally tired of listening to his screams from this I moved on to removing the clothes pins from his dick. I did this with a riding crop. Some came off easily, others not so much. When they were all off I removed the nipple clamps one at a time. After removing one clamp, I slapped his nipple with the riding crop.

I then put him in a standing bondage position. His wrists chained to the beam above him , his legs shackled to a spreader bar. I tied his sad little dick up. I then flicked it with my fingers. such a small yet intense sensation when the area is bound like that. I put a parachute on his balls. Slowly I began adding weight. I would stop only to push the weighted parachute back and forth between his legs. I put quite a bit of weight on his balls before he began sweating profusely and needed to tap out. I told him that I don’t like when men tap out early . He could never pleas me. but he knew that. He has an insatiable need to fantasies about fucking me so he will be in on a regular basis for his punishment.

 

Strap on fun

A slave who I have been seeing for a few years recently booked a session. It had been awhile. He had been seeing me since he was 20 and now he was a 23 year old cock sucker. He told me how much he missed our sessions as they had helped him grow. He was now exploring his bisexuality regularly.  Cock sucking all over town. He really wanted to come in and take my dick.

I like to get him real slutty. I put this little sissy in a long red wig, red lipstick and burgundy panties. I so enjoy watching my sluts flaunt their sissy self and he is just fantastic. He loves to shake his ass and beg me to let him be my cum guzzling slut.

After his performance, I had him get on his knees. I shoved my cock down the throat of this cum dumpster. I must say he is amazing at deep throating . Loves to get slapped across his face with my cock and rub it along his lips.

I bent him over and began getting his mussy ready. I put in a butt plug to make sure his ass stayed nice and stretched for me before I shove my cock in there. I had him suck my dick a little while longer simply because he is such a slut about it. I bent him over again, removed the butt plug and inserted my cock. It wasn’t huge because he is more of a regular cock sucker not always getting pounded. Though this day he got the pounding he so desperately needed. After getting his ass warmed up, I gripped his hips and moved them back and forth on my cock. I pulled her hair, slapped her ass as I pounded this sluts mussy. She screamed in pleasure and I went harder.

When I finally took my dick out of her she got right on her knees and begged to suck my cock. I am one to never resist a little ass to mouth so I grabbed her head and thrust my cock deep in her mouth giving her every last drop of her ass in her mouth.

Our usual and frankly one of my favorite rituals with a slave is when she jerks her clitty off and cums right in her mouth. So entertaining.

My newest chastity slave

This slave was traveling about 2 hours  for a first time session with me. He told me he put himself in chastity about a month prior in the hopes of seeing me. He contacted me about an hour before  our session to say he was going to be late as his tire had popped and he was waiting for AAA. As he waited for them he text me that he wasn’t anticipating it being as hot out as it was and how the chastity device was really irritating him. Of course I found this hilarious. He ended up being an hour late for our session due to traffic and a flat tire. A 2 hour journey turned into 4 hours. He didn’t cancel and turn around but I think that he was more so thinking about being out of that chastity device. As usual a man thinking with his dick.

When he finally arrived, I had him go straight to the room we were to be in and strip. He brought with him a few leotards and stockings. He informed me he enjoys wearing the leotards under his work clothes. I had him put a green leotard. I put a collar on him and told this bitch to get on his knees. I had him lick my stilettos clean. He was just so pathetic looking in his outfit and  I already knew he was uncomfortable from sitting in a hot car in a chastity device for 4 hours, so I must now give him wedgies. He’s a whiner so after he whined about the wedgie I spit in his face. What a pathetic site, a sweaty man in a leotard with a wedgie covered in spit. At this point I decided to treat him like the dog he was and have him play fetch with me. I figured this beast was thirsty after all of this so I got a dog bowl out for him. I began by spitting in it, then I pissed in in. I told him to crawl over and lick up the contents of the bowl. He lapped it up in record time.

I again had him strip then change into a pair of shiny nude pantyhose. I put on my strap on had shoved my big cock down his throat. When I was finished skull fucking him, I bound him to the St. Andrew’s cross. Since the chastity device was bothering him, I decided to use a vibrator on him. I can not express how delighted I was to see how much all of this was getting to him. When I was kind enough to let him out of chastity, I had him get on his knees and face the wall. It took about 15 seconds for this pathetic excuse to cum not only on the floor but on the wall. I told him he was an absolute idiot to do something so thoughtless. I slapped him across the face and made him lick all his cum from the floor and the wall. I also made him clean the wall before allowed him to get dressed.

He later wrote me about the amazing time he had and how he wants to serve me. He asked if I would oversee him the next weekend via text and phone as he was going to stay in his basement, chained to the floor in chastity and a leotard. I agreed and what a ridiculous 2 days it was. I had him send me pictures of himself through out. when he asked for permission to use the bathroom I told him to go out in the yard. Fearing he would be seen by a neighbour, I informed him his only other option was to piss himself which he did. He is a whiner so of course he kept saying that the basement floor was cold to sleep on and how he smelled terrible. I am glad I wasn’t there to smell him after 2 days of no shower and pissing himself in a leotard and pantyhose.

From the slave’s perspective

This is another one of my slave’s sharing our session from his perspective.

Footboy’s Story of Humiliation:

“I have had the pleasure of serving Mistress Isadora a few times now. Each time gets better than the previous session which is why I keep coming back for more (I have told her she has become like an addiction for me).
Upon contacting Mistress for the first timjust outlined a few of my interests, mainly humiliation and an insatiable foot fetish. Mistress did not disappoint with just those few details I provided.
Mistress was so warm and welcoming when I entered the dungeon for the first time. After some small talk, she had me strip naked and get all on all fours, she informed me going forward that she expects someone as pathetic as me to greet her in that way all times going forward.
The verbal assault and physical humiliation took off from there. She called me every name in the book (bitch, slut, etc). all while teasing me with her feet. After a while of forcing me to clean her boots (with my tongue of course) she finally allowed me to remove her boots and start kissing and licking those beautiful bare feet. She could sense that I was getting too excited but told me she was not done with me. She walked me on my leash into the bathroom and told me to enter the tub. Mistress then proceeded to put these ridiculous bunny ears on me and urinated all over my pathetic body. She informed me I could finally release and needless to say it took a matter of seconds after one if the most incredible times I had ever had.
I have seen Mistress many more times since then like I said. She just keeps getting more creative each time. A few additional highlights have been surrounding food play. She has had me being cupcakes and then proceeded to shove them in my ass. Of course I have been made to eat them after pulling them out. She has also made me cum on them and the consume every last drop. All the while the verbal assaults just keep getting better, one of my all time favorites was “how pathetic…you need my toes in your mouth to cum.” Just the way Mistress said it, pushed me over the edge.
Mistress has also taken me in public a few times which takes it to another level. She has forced me to rub her feet in a restaurant while chewing her food then spitting it into my drink which then I was required to drink. We have been on shopping trips as well where I am expected to buy Mistress some items her gear desires which if course I would never say no to. However, she of course requires me to carry all the bags as well as her purse! I definitely feel shame as I know people think I’m a loser but like I said Mistress us an addiction so I’m more than happy to do anything she asks me to do.
After writing this, I feel the urge to schedule another session soon to see what other creative ways beautiful Mistress Isadora has come up with to further humiliate me.”

Entertainment

I had a sweet little humiliation slut come to see me the other day. It was his first session and although he had many online experiences this would be his first real time session. I just love popping cherries! He also really enjoyed strap on. He wanted nothing more then for me to tell him how worthless he was as a man. He was game for everything I suggested. He told me how honored he was to be in my presence and be able to swallow my spit. He was such a slender thing so of course I put him in a pair of ruffle panties. He wasn’t so terrible to look at so I made him dance for me. My own little private dancer. He looked so ridiculous shaking his hips in those panties. Then he got lucky. I told him to bend over the bench and I cuffed him to it. I pushed those panties to the side and showed his mussy who was boss. When I was through with him, he wanted to entertain me more. I told him I wanted him to stick his fingers in his mussy and eat it, which he obliged and enjoyed of course. Toward the end of our time I told him I wanted him to jerk off and eat his cum. He said “Mistress can I just jerk off into my own mouth?’ He said this was something that he did often. Fine by me! So there he goes throwing his legs behind his head, jerking his pathetic cock. I have never seen a slave so flexible. I asked if he did yoga. He said he didn’t he has just always jerked off this way and has  tried to suck his own cock. A few stokes later  he blew his load in his own mouth! Now that’s what I call entertainment.