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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Double Strap On

I had a fantastic double with Skyler Grey a few weeks back. We are both Scorpios so of course we have amazing chemistry together. It just so happened that this slave was into astrology and that was one of the reasons he wanted to book a double strap on, role-play session with the two of us.

We met him at the bar and hit it off so we decided to bring him back to our place. We chatted to get him loosened up and to get his guard down. We toyed with him, using our lady parts against him. No man can resist.  We then convinced him to let us cuff him to the cross. We each took an arm and a leg. When we met at the bar he was not expecting to be used for our entertainment. We pulled down his boxers to reveal his cock, hard of course. Even though he said he didn’t want it Skyler and I knew he did. Like with all men, we know how to get what we want from you. We rubbed our beautiful asses on his dick only to then torture him with a mechanical toothbrush. I began twisting  his cock slowly, as Skyler twisted his balls in the other direction. We laughed as he yelled out in pain. He obviously wanted to give up all his power to us, as we were going to have our way with him whether he liked it or not.

We uncuffed him and had him get on his knees as we slipped into our strap ons. I grabbed him by the hair as Skyler slapped him in the face with her cock. He confessed he wanted nothing more than to suck both of our cocks. So we gave it to him. He became a total whore for our dicks. Deep throating, getting slapped with our huge cocks and skull fucked. I told him he was our cum dumpster for the taking.

After working his mouth out, I suggested we stuff more of his holes. Skyler sat on the bondage bed and told him to come hither while jerking off her strap on. He went over to her and bent over to wrap his lips around her cock. I decided his mussy was mine for the taking. I slowly thrust my cock into him at first. I laughed seeing this slut wince. I highly doubt this was his first time at the rodeo. The faster I went, pushing harder into his ass, the faster this whore’s mouth rode Skyler’s dick. He couldn’t get enough of our cocks filling his holes. I grabbed him by the hair on the back of his head as I thrust my cock in his mussy making him call me Daddy. Another highlight of this strap on fest was Skyler and I joining hands to “Eiffel Tower” his ass. Skyler and I love Paris. He kept saying he was going to cum so as I pounded him, Skyler instructed him to jerk off in his hand and eat it. So he did. We all had quite a time that afternoon.

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…

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.”

Heavy rubber

I have a thing for latex. I feel amazing in it and it contours my body fantastically. I’ve had a few latex fetishists of recent  which has been great. I wrote about one a few months back. He also had a smoking fetish. I had a great time seeing him on a few occasions since. A latex clad domme with shiny red lips smoking is so seductive and sensual.

I also had a fun sissy who had quite a latex wardrobe while I was in San Fransisco. She just wanted to try on her beautiful gear as I dressed her up in this great wig she had. She was a vintage enthusiast and it definitely showed in her choice of apparel. Such pretty dresses! She pretty much entertained me with a fashion show and we took a bunch of pictures. I  posted one in a tweet of her bent over, strapped to a bench with me fucking her ass. Such a rubber hussy!

Another rubber slut I have seen, in addition had a face sitting fetish and  enjoyed sensory play. He had all this fantastic gear as well.  He had  latex catsuits, corsets and masks. The one I picked for him was a catsuit with blow up tits.  He told me if he had a pair of tits he would never leave the house. Typical male thought pattern.  I was in full latex, my hot red leggings and buckle top. We also took some pictures.  I love the visual latex gives especially a man in a catsuit with blowup tits and a heavy gas mask.  I had him take off the gas mask and lay on the bondage table.  I strapped him down, unzipped the crotch of his catsuit and pull his cock and balls out. I attached the electric pads of the TENS  to both balls, the under side of his cock and the head. I played with the intensity and pulse for a bit. I left it on as I put my hand over his mouth laughing as he struggled. I allowed him to breath a bit before I smashed my tits in his face and cranked up the electro to his balls. I lowered the electro before I sat on his face. I knew my latex covered crotch and ass would drive him to the edge. I took the electro up another notch. I did this for a while, bringing him to the edge with the electro and my ass to only leave him hanging. He was so engulfed in rubbing his face in my ass,  finally he could no longer control himself.

I have really enjoyed having  the chance to come up with a variety of scenes for all these latex lovers. They have all been so different and such absolute  fun in there own way.

Degradation

I recently sessioned with a new humiliation whore.  He asked that we start from the door, that I greet him in a demeaning way. He let me know he pretty much had no limits as far as degradation and wanted me to make him my sissy bitch. I named him Daisy.

I answered the door and there he was. This was going to be easy. Tall, skinny, glasses. I closed the door behind him, looked him up and down, and told him I could smell the sissy on him. I ordered him to follow me to the black room. I told him to remove his clothes and wait for me on his knees as I picked out a few toys for us.

I grabbed a hot pink lacy number, red satin panties, brunette wig, black heels and some red lipstick. Nice and slutty. I opened the door and there he was. He was truly pathetic. Very dainty and tall. I made him put on the panties. They were a small and they fit his little ass! I put this little whore in the heels and told Daisy to dance. She started twerking immediately. I could not hold back my laughter. I mean this bitch is seriously trying to impress me and will obviously do anything to entertain me, even if that means completely humiliating  herself. I love the power I have.  I had her take a break from dancing so she could put on the hot pink number and wig. I then put a ton of red lipstick on her. I told Daisy to start twerking again. I got behind this skank and spanked her ass. Told Daisy she was mine for the taking. She  told me she wanted to be my whore, suck my cock and get fucked hard by me. These were things I already had in mind. I ordered The whore to her knees and I put on my strap on. I slapped her across the face. The slut told me she liked it rough. I spit in her face telling her she needs to be prepared for all the cum that is going to go all over her from for all the dicks she would be sucking. I grabbed the back of her head and this bitch went to town. Deep throat queen! When my slut would start choking on my cock I would spit in her face.

I had her bend over a bench and spread her legs. I began gently but once this bitch got into it she was riding my cock hard. I spanked her ass with my thrusts. When I was through with her, I had her get on her knees in front of me. I made this bitch suck my strap on. I told her she was such a whore she wants to eat her own ass.  Daisy loved the taste and would eat anything I told her.

I had this repulsive whore  lay on the floor. I put my  toilet chair over her head. I had an extra special treat for my slut. I had my period. I pulled down my panties and sat on the toilet. I reached down and pulled out my tampon. Nice and full of my special sauce. I stood up and looked at Daisy from the opening of the toilet. Told her to open up and I slid the tampon in her mouth. Daisy  closed her mouth and swished my bloody tampon around a bit. She looked funny with just the string coming out of her mouth. I told her to open her mouth as I sat back on the toilet. I knew she was thirsty after having that cotton tampon in her mouth. I pushed out a little of my nectar and then I farted right in her face. I really wish it was a bigger fart but at least it was a bloody one. I  began pissing down Daisy’s throat again. She drank some of it even with the tampon in her mouth. She did get quite a bit on her  face and in her hair.

When I was finished I stood up and looked down. There she was with her mouth open and a huge piss filled tampon in her mouth. I allowed her to clean wipe  off a bit. I told her she could take a shower. She said she didn’t want to. I am so elated at the levels of abasement this whore is willing to go. As she was getting dressed I told her that instead of a shirt she had to wear the pink nightly. I told her to cover it with her jacket  and stop for milk on the way home. Before going into the store she must open the jacket and take a picture. I walked her to the door covered in my piss. I had her kneel before me at the door. I told her to send a picture from the store. I slapped her, spit in her face and through her out.

About 20 minutes later I receive a text and pic from the pee pee boy. I text him I bet everyone can smell my piss on you. Don’t you know this whore couldn’t get enough and contacted me the next day to be a butt fucked, tampon eating piss whore! I had alot of fun with this one and I am sure there will be more stories of utter humiliation.