Hotel Series: The Extended Session

For this session since it was my longtime slave’s birthday he booked a large suite in Center City.  Since we were to be doing a 9 hour session, I wanted to get more creative than usual and use multiple spaces, even some public play.

We began at The Chambers. After having him strip naked and shower, I put a collar on him. With leash attached, I led him to the play room. I cuffed him to the cross and began fogging him with various floggers. Then I worked my way to a fun double tailed whip I adore, then a dragon tail and finally my single tail. When I was finished, I caressed his back and ass with vampire gloves. Now he was nicely marked and reddened up, I gave him a treat and allowed him to lick my boots. I had him fetch me the water and snack bars I had him bring for me. Beating men takes energy, so I had him rub my feet as I ate and drank because hydration is important.

Next, I bent him over the bench. I cuffed his ankles and wrists to it, his thighs and waist I tied down to the bench. I don’t like much wiggling. I used one of my favorite toys, a humbler to get him just where I want him which is by the balls. I flicked those tight balls with my finger then used an electric toothbrush on them. Played with the violet wand using a few different attachments for different sensations all over his body.

I bound him to the bondage bed. I brought over a metal tray with a few syringes, needles and a bag of saline. I began filling up one of the syringes with saline , then poked him in the balls with it. I must say its a bit intoxicating. I did that about 7 or 8 more times and noticed his balls were inflating. I then did about the same amount in his dick, watching the skin stretch a bit. Now that his cock and balls were looking even more pathetic than usual, I thought it a great time for public play. After getting him out of bondage, I put a remote control cock shocker on his odd looking crotch before I had him put his clothes back on.

We went to lunch. As I snacked on lobster and escargot, I shocked his dick with the remote. We were dining al fresco so the thought of getting him caught was a delicous mind fuck. When I was finished, we made our way to his hotel room and he brought up my huge suitcase of gear. I had a friend joining us so when she arrived I got changed into something more comfortable: PVC ensemble with fishnets and boots.  I was ecstatic to break in my new leather sleep sack. I zipped him in it and laced it up leaving his cock and balls out ready to be tormented. I put him in a sensory deprivation hood also. I bound his little parts and set up all my new electro toys. I used pads on his balls, a fun head shocker with a urethra attachment and what I like to call the little lasso. With all this going on and him completely deprived of all of his senses except for the feelings of electrocution running through his cock, I took the time to catch up with my girl. We would laugh when he would sorta moan and shake when the electro machine would run through another setting.

When I let him out of the sack, I gave him a short break after all that electro. By break I mean I had him assemble the bed bondage. I attached him to it, spread eagle. I brought the rest of the bag of saline to finish off. Now I know when doing saline inflation, an IV is easiest but there is just something about poking holes in flesh I find exhilarating. Our voyeur is a vet tech and she also suggested that but agreed watching me administer those injections of saline was entertaining. When his cock and balls were about 2 times their normal size, I stopped for a bit to whip and flog them. I then used sounds on him which was not only odd to do with his inflated cock but he said felt even stranger. I proceeded to inject more. When we were finished I put 700ml in his cock and balls. I just slapped them around and played with the ridiculous looking gummy thing that was his crotch. My girlfriend just sat there laughing the entire time. I made him walk around the hotel room and jump up and down with his huge inflated balls. As he was doing this my friend and I laughed, drank champagne and ate chocolate. Such fun girl bonding that day.

 

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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.

Trampling double

I had a fantastic time teaming up with Skyler Grey for a double session recently. I haven’t had trampling session in a bit so I was excited about this session for many reasons.

We had him lie on the floor, no bondage as that really wasn’t his thing. We began running our soft pedicured feet all over his body, alternating giving him a taste of our delicious toes. Skyler is a tall red head with larger feet and I am a petite platinum blonde with smaller feet. This foot fetishist got to enjoy the best of both worlds.

He could take much more than I have seen in some time which was just wonderful. We  walked all over his stomach and chest, both of us at the same time. Skyler would trample his stomach as I stood on his chest putting my foot in his mouth. She would sit her beautiful ass on his face as I would jump up and down on his chest. He would struggle a bit to breath into her ass as I jumped.

We were dancing on him and doing yoga. We had such a great time. I thoroughly enjoyed standing on his chest with one foot and using my other foot to step on his neck . He wasn’t into edge play per say, just the amazing feeling of being crushed by beautiful women. At some points I sat on his face as Skyler jumped around on his chest. At another point I stood on his face and at another Skyler and I both had a foot standing on his face and chest. We both of course had to step on his cock a bit and shove our feet down his throat. We also would sit our asses on his neck. He got a great view and smell of our luscious asses this way as the other would trample his stomach and chest.

Virgin Golden Shower

I recently had a session with my youngest twink yet. Freshly 18 years old. He wasn’t sure if he wanted to explore too much but he had a few definite interests. I was thrilled he was trusting me with his first experience.

What a sweet little twink he was. When I opened the dungeon door, there he was standing there naked. After putting on some music, I turned to him and began the first bit of training. I had him get on his knees, head down ass up. I put my platform boot on the back of his head and informed him to memorise this position.

I put cuffs on his wrists and ankles. With a spreader bar, I tied his legs and arms to either end of the suspension frame . I then placed my ass right above his face. I teased and taunted him dropping my ass on his face then bringing it back up. I finally sat on his face, smothering him. After a while he began to struggle and I could feel him attempting to breath in my ass as I moved around to keep him from taking any deep breathes. I laughed as he struggled more, then I sat up. He was tried desperately to catch his breath and when he did he was smiling. What a little pervert. Just what I like. I just kept sitting on his face for a longer about of time. I so enjoy listening to slaves struggle to breath in my ass.

I then decided to change it up and wrap him in plastic. I ripped open the area of the plastic by his crotch and pulled his cock out of the plastic. I began to use a vibrator on him to take the torture up a bit. I sat on his face and held him don tight as I also used the vibrate on his pathetic dick. Virgins are just so fun. I wrapped my thighs around his head in scissored him rubbing my ass right in his face. I began spitting in his face and in his mouth. I stepped all over his pathetic little cock to then make him lick the taste of his dick off my feet.

He had mentioned he was thinking of trying a golden shower. I absolutely delight in pissing down the throat of my pets. Giving them their first taste of the nectar of a goddess especially. I stood over him and began pissing right down his throat. I was well hydrated so this virgin definitely got the most amazing first shower. Lucky boy.

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.”

Bitchy sister role-play

Over the years I have done many different role play sessions. This one involved myself and another dominatrix as the sisters of an overweight boy who wanted to tickle his sisters’ feet.

The scene started with my “sister” and I sitting on the floor in one of the dungeon rooms reading a magazine. Our “brother” comes over to see what we are doing. The slave wanted us to be mean bitchy girls who did nothing but torment their brother. As soon as he comes over to see what we are doing, we don’t even try to hide our disgust. We humiliated him because of his weight, how annoying he is and we want him to go away. We told him to sit in the corner an leave us alone. Myself and the other mistress sat on the floor on the other side of the room away from him to finish reading our magazine. Of course here he comes, our annoying brother. He sat on the floor with us by our feet. We ignore him, so he starts tickling our feet. Being tickled is not one of my interests but this role play was such a great time, I had no problem when he asked to incorporate his interest. We scream and yell at him, kick him and slap him when he tickles our feet. He just won’t stop and won’t leave us alone. We notice him getting hard. We make fun of how gross he is to be getting a hard on by tickling his sisters’ feet. We just ripped into this pervert and his micro dick, slapping him every time he would touch his dick and try to tickle our feet. We then tackled him and started tickling him. We held him down and made him sniff our feet. The 2 of us had a ton of fun shoving our feet in his mouth and trampling him.

I really enjoyed this psychodrama. The scene wasn’t scripted. We both knew his interests, hard limits and how he wanted to incorporate the mean sister role play. I love exploring the depths of people’s fantasies.