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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Latex

I have a thing for latex that is shared with some of my slaves of course. I have one in particular who has some amazing gear. I was thrilled when he asked me to pick a catsuit and thigh high boots for our next session. We have similar taste .

We each changed into our latex in separate room. When I came into his room there he was in a black latex catsuit with the same thigh high boots he had gotten me. I allowed him to clean, polish and shine my latex. I enjoy the ritual. he then shined my new boots with his tongue.

I locked him to the St. Andrew’s Cross. I unzipped the croth of his catsuit and pulled out his cock and balls. I rubbed my shiney latex ass all over his cock. I then turned around, grabbed it and twisted it. He moaned and I laughed. I love the feeling of twisting a cock in my hand. I made him eat what drips out of his pathetic cock. I used the vibrating toothbrush on the head of his dick. The CBT continued with cloths pins and a vibrator on the head of his cock. I so enjoy watching slaves squirm, alternating pain and pleasure.

I ordered him to the bondage bed and hogtied him. I slid my dick in his ass and trusted slowly at first. When he begged me to fuck him harder I pounded his hogtied ass faster and harder. I love hearing him squeal. I banged him so hard in all this latex I thoroughly broke a sweat. Before I let him out of the bondage, I let him sit up a bit and lick the sweat off my chest then lick my cock clean.

Next, I tied him down to the bondage bed, legs spread. I hooked this electric slut up to a cock ring and a loop around the head of his dick. I then sat my latex clad ass right on his face. Feeling him try to breath as I move my ass around. Love how it just slide back and forth on his face. I enjoy over stimulating my whores and used a vibrator and I was sitting on his face. His pathetic dick was so hard and purple when he finally came on his latex.

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.

She likes to entertain

I session out of a fully equipped dungeon but I do like when slaves bring their favourite toys. It is a new experience for both of us. This sissy brought a few of his own outfits. I always find this hilarious because I know this bitch has been wearing this outfit around the house or these lingerie pieces under his day to day clothing. His particular outfit of choice is a leopard triangle bra top with a matching thong and sarong. The sarong has coins on it like a belly dancer.

As I sit there and have her explain her ensemble to me, she can not resist touching herself and showing herself off. What a whore. Just what I like and so perfect to have entertain me. I had this slut slip into a pair of black heels. I put on some belly dance music. I told her to show me how she was going to win my attention. She started swaying her hips, touching herself. That little whore’s clitty got harder every time I threatened to use her every orifice as a cum dumpster. I needed to slap her hands from rubbing her clit. As she sway her hips I got behind her and thrust my hips up on her ass. I lifted her short skirt and spanked her.

She brought knee pads with her so of course we are going to use those. One they were on I also put her in a collar with a leash. I made her crawl to the bathroom as I led her on the leash. I ordered her to lick the toilet like the piggy bitch she is. She went to town licking the entire bowl,  lid, and enjoyed a bit of fresh toilet water as to not dehydrate. As I led this pig back to the room I yelled “swine” and flogged her. I though it similar to to “shame” for you GOT fans.

When I got her back I pulled her thong to the side and plugged up her mussy. I then put on my strap on. I bent her over the horse and locked my piggy down. I shoved my big cock down her throat. You know where this goes and that’s only a taste…

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.”

New Explorations

One of my slaves who I have been seeing for over a year,  requested a forced bi session. I was totally down for it but unfortunately due to schedule restrictions I couldn’t make that happen. My sweet little slave wanted to see me either way. He is more than fine with sucking on my cock and getting banged by me.

I figured since we were unable to to explore the new forced bi aspect of our play, we could incorporate other kinks. This little sissy is still somewhat new but he is open to exploring things with me. I decided that I wanted to lock him to the St. Andrew’s cross. We usually stick with alot of feminisation so  I wanted this session to be a little different. From there I reminded him he was my little sissy play thing, a toy for me to use for my own enjoyment as I pleased. His little clitty got rock hard when I said that. I applied a slutty shade of red to his lips and tied up his clitty. He is a sissy slut after all. I took out the violet wand, something I had never used on him before. I ran  the wand up and down his inner thighs. I could tell he was enjoying the sensation so I cranked it up a little more. I brought it up to his nipples and gave them a little zap. I ran the wand down the from of his body to his bound clit. I began at the head and went down his shaft, around underneath and his balls. He was moaning the entire time. I then blindfolded him. I rubbed my tits on his chest saying this is what real tits feel like sissy.  I used the electric toothbrush on his nipples and bound up clit. I alternated using the violet wand and electric toothbrush on this blindfolded bitch.

I unlocked his arms and legs then told  him to lay on his stomach on the bondage table. I hogtied this little sissy. Such a vulnerable  position. I put on some gloves, lubed up his mussy and began loosening him up. I started with a small butt plug which slid right in. I knew I could get in a much larger one so I did. I let him out of  the hogtie and told him he had to keep that butt plug in as he got on the floor. I tied his arms behind his head and a spreader bar to his legs. This slut kept the butt plug in the entire time. For a reward I told him he was now going to have both his holes plugged. I knelt over his head and began to skull fuck him. When I was finished using his face I untied him and allowed him to jerk off into his mouth. I just love how we end every session with him in some yoga pose cumin in his mouth.