Shemale Mistress Stories

Shemale Mistress Stories
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For some time I had been having these thoughts about what it would be like to experience the acts of sucking a cock and being penetrated by one. The problem was that despite my obvious bisexual infatuation with the idea, I just couldn't see myself engaging in any sexual activities with some muscular guy. The answer came in the form of a webpage about TS escorts. I contacted one very feminine looking lady and arranged to spend an over night session with her at her flat. I had explained to her that this was to be my first time for anything like this, and that I really thought that I would need her to be very forceful and actually make me do all the things I had told her I wanted to try. This, she said, would be no problem as she really enjoyed being a dominant mistress type, but whatever happened she would make sure it was pleasurable and not painful.

When I arrived at her flat, the door was opened by this stunning blonde lady, wearing a full-length robe, who led me in. After we had sorted the finance side of things, she explained to me that while I was there I was to call her 'Madam' and that I could stop things at any time by simply saying 'red no'. She then removed her robe to reveal a superb body encased in a red basque and panties that were obviously straining to contain her extra surprise.

She said, "You are my slut to do whatever I want with, do you understand?" I replied, "Yes Madam," to which she replied "Good slut! I am going to leave the room for a few minutes to make few preparations, and when I return you will be naked and on your knees with your forehead touching the floor, understand?"

I replied simply, "Yes Madam."

She left the room and I did what I had been told. After being in the assumed position for about 10 minutes I heard her return and stand next to me.

"Good little slut, now stand up and follow me." She led me to a very large bathroom and told me to get in the empty bath. "Before Madam plays with any slut they have to get clean inside as well as outside, so lay on your side, ready for your first enema."

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Great Story , (personaly wish it was me ;-)!)
Great story very Hot! What did they do the rest of the night? Please have a second part.
Very well written. Very graphic. I loved the ending. I would have loved to read what happened in the shower.
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My first time meeting with a dominant Tgirl.
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It was now a couple of years since my first and only meet with a tgirl. I met an Asian woman a few years ago and I was very much in control, she sucked me, I rimmed, fucked her and I promptly left. Being a straight guy I felt kind of weird about the experience and decided it would best be a one time thing, something to tick off and I forgot about it for a while. Eventually my initial curiosity started to grow again and I started to watch an increasing amount of TS porn and came across videos were tgirls would dominate guys. I was kind of shocked by this but also kind of turned on. It was something totally different to anything I had seen, let alone experienced and I found myself imagining what it would be like to be a toy for a dominant TS mistress. I began to look online on swingers sites looking at various mistresses who were looking for slaves but had never met any. The ones I liked the look of weren't in my city, plus I didn't know if I was ready, I thought this might be something way out of my comfort zone.
One day I was browsing on the site and to my surprise, one of the mistresses I had fantasised about before happened to be in my city that weekend. She was Brazilian, 5'5" tall with long black hair, looked feminine but was very well endowed and apparently very dominant. Without really thinking I sent her a message, I explained that I was a curious sub guy and I wanted to serve her. She messaged me back with her phone number and told me to send her naked photos from the front, behind and more face pics. Immediately, I stripped down, got my phone out and did as she said sending the pictures. After a few minutes my mistress replied, she was pleased and she said she liked "young, inexperienced slave boys" and that she would message me when I was needed.
I had largely forgotten about this and didn't really expect anything to materialise these messages. In my head this was still very much just a fantasy but two days later I was home alone, it was the evening and my phone screen lit up. It was her, the message read "Slave, you are to come to me and serve me at 11pm" and attached was an address as well as instructions of what to do. I had been summoned and was panicking as to what I should do, who knew what she would do to me? I was thinking, could I really go through with this? What would people think if they found out?! Then again, when would I get a chance to live out such a fantasy again? Plus I had now promised myself to this mistress. It was now 10:30 and I stopped debating the situation, put on my coat and left.
The address was about a 30 minute walk from mine and I looked it up following maps on my phone. Those 30 mins raced by, my mind occupied with the thought of what could happen to me and I text mistress that I had arrived and approached the hotel building . I opened the front door which was open just as she said it would be and the reception was totally empty, nobody was there. I started to walk up the stairs, my legs trembling slightly and I finally reached the top floor as instructed. A door wide open, awaiting my arrival stood in front of me, I took a deep breath and walked in.
I took two steps in and my mistress stood facing me. She looked a lot like her photos, perhaps slightly more muscular than I had imagined but nevertheless good. She wore knee high boots, a leather corset, black stockings and a short black skirt. She welcomed me in and asked me how my journey was, speaking in a thick accent with quite a soft yet demanding voice and I replied nervously telling her it was fine. She beckoned me further towards her and I took a few steps forward. She was quite clearly looking over me and after a few second of silence she spoke. "Remove your clothes" she demanded. I looked at her then replied "yes mistress" and did as she said. I took off every last piece of my clothing and stood in front of her totally naked. Next she pointed to the bed and instructed me to sit on all fours in the middle of it and face the wall. Now I sat totally exposed and my mistress walked around me, inspecting my nude body, I started to feel increasingly vulnerable. She did not say much but soon I felt her presence over me, she put her arm up to my neck and attached something. She had attached a dog collar around my neck and I was now on a chain, she pulled it side to side testing it and I moved with it. Satisfied she got onto the bed kneeling in front of me. It was very clear I was no longer in control, I started to feel very submissive and part of me wanted to leave but I felt an overwhelming need to obey her.
She yanked my chain towards her, pulling my face towards hers and she kissed me deeply, her tongue in my mouth. Suddenly she stopped and maintained her grip on my chain but moved away to look at me in the face. "You're going to be my bitch and do exactly as I say" she spoke commandingly. I couldn't believe I was actually in this situation but I replied "yes mistress", however, I doubted wherever this was even a question at this point. "Good boy" she replied and she relaxed her grip allowing my head to look down once more. As my head retuned, I came to realised whist she was kissing and commanding me she had lifted her skirt and moved her panties. A huge cock was now exposed, looking me in the face, it was rock hard at least 8 inches, very thick, with a huge curve. I knew what she wanted and before I could say anything she pulled my chain hard towards it and my mouth opened around it. It was huge, much bigger than my own and although this was my first time I began to suck it the best I could, taking as much of it into my mouth as possible. She was enjoying it and began to thrust into my mouth as I sucked causing me to gag loudly. Then, she suddenly pulled her cock away and pulled my chain, looking me in the face. "Tell me you love sucking mistresses cock" she demanded. "I love sucking your cock mistress" I stuttered, in disbelief of what I was saying. She pulled me back down to carry on and I felt extremely humiliated but continued to pleasure her.
As I continued mistress now began to feel my body and grab my ass, spreading my cheeks and playing with them. I felt and heard a hard "smack" as she spanked me aggressively and I may have let out a moan had mouth been able. This continued for some time until I felt two lubed fingers enter my virgin hole. I had never experienced anal other than maybe a finger and she started to slide them in and out of me whist I had my head buried in her crotch. It felt ok, not unpleasant, but strange and I started to groan as she worked and loosened my tight ass. "You've been fucked before haven't you?" mistress questioned. I told her I hadn't but unconvinced she called me liar. I promised her I hadn't and she said "I'm going to be your first then slave". She then told me to beg her to fuck me. "Please mistress will you fucked me in the ass" I exclaimed humiliated with a bright red face. Pleased she got up put on a condom, covered her cock in lube before smearing my hole in lube still using her fingers on me.
She instructed me to lay on my side and she lay behind me, her cock between my ass cheeks. I could feel the tip of it pressed against my hole and she slowly started move with increasing pressure into me, before I knew it I had given way and her head was inside me. I let out a yelp but In and out she started to pump slowly until she was managing to fuck me. It did hurt and could feel my hole being stretched hard but I was just about managing. After several minutes I was now commanded to do the work and I moved my ass back and forth feeling her slide in and out of me. I felt extremely submissive, not only was I being fucked I was now doing the work, riding her. Finally she commanded me to my knees pushed my head to the floor and pulled my ass cheeks apart exposing me even more. Now in doggy she slid herself back into me and grabbed me by the hips fucking me harder than ever before. It felt good but at the same time my ass burned. She then pulled my hair so hard I moaned in pain and she made me shout, telling her I love being fucked by her until she let go. Embarrassed I complied and after a while to some relief she stopped fucking me.
She now lay on her back, removed her condom and was still hard as a rock but briefly turned her attention to my cock. "Be ready to cum" she instructed, "when I cum your going to swallow my load and cum at the same time". I started to play with myself for a little whilst mistress watched and after she was convinced I was close she forced my mouth back over her dick and I sucked away. Mistress was now close to cumming as well and started to moan. Faster and faster I sucked mistress and played with myself and before I knew it her cock twitched hard and she shot a load into my mouth. Accepting I swallowed taking it down before allowing myself to taste it and simultaneously I came over her leg and the bed sheets.
Satisfied that I had completed her task she allowed me to go to the bathroom to clean up myself and soon after I got redressed, thanked my mistress and left. The walk home was painful, each step a reminder of what I had just endured. Altogether the experience was every bit as extreme as I had feared but also hoped it would be and again I thought it best a one time thing. Only time will tell if it stays that way.
Wow. Excellent story. Something to aim for
loved the part when they both came at the same time
I know it and you know it that this isn't going to be a one time thing. Before long you'll be craving another plowing by a HOTTTT Shemale. It's just a mater of time and availability. There are plenty of will Shemale escorts who travel and if you befriend them they'll make a point of stopping in your hometown to a romp. It's a BIG business.
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I had heard some intersting comments about this S and M club and so I decided to go by and check it out.
I walked in about 9pm and things were just starting to get warmed up. I sat down with a beer and looked up at the main stage where a gorgeous raven haired dominatrix with an enormous set of tits was asking for a volunteer who needed to be disciplined.
I thought what the hell, "why not give it a try" after all that's why I had come here.
As I approached the stage I figured maybe she would tell me to take my pants down and give me a little whipping and then send me red faced back to the audience
So I was completely surprised when as I stepped onto the stage she told me to take off all my clothes and then kneel in front of her.
Although somewhat taken aback I reluctantly complied and knelt in front of this beautiful buxom Godess.
She told me that her name was Mistress Raven and that I was to address her properly at all times. I replied "Yes, Mistress Raven". Then she told me to get down on all fours and slowly turn around.
As I did so she said, "Well, what have we here you filthy slut. Is that a butt plug in your ass?" - "Yes, Mistress", I said. "So you like to get fucked in the ass, do you?"
Then she put handcuffs on me and attached a five foot long bar to my ankles with cuffs so that my legs were spread wide open.
As it was almost impossible to kneel with my legs spread so far apart she attached the chain of my handcuffs to a chain hanging down from the ceiling and pulled the chain up until I was upright.
She then grabbed a paddle with holes in it and started to pound my ass again and again until the pain was excruciating.
As she continued to hit me she cried out, "Do you like to suck cock, bitch?!" I figured that if I said what she wanted to hear maybe she would stop hitting me for a while so I cried out "Yes, Mistress Raven!" - "Yes, Mistress Raven what you dirty slut?" - "Yes, Mistress Raven I like to suck cock!" I yelled loud enough for everyone in the room to hear.
She stopped hitting me, came around to my front and said "Well, my little bitch your Mistress has a nice surprise for you."
Then she took off her short leather skirt and staring me in the face was an enormous throbbing cock that was getting harder by the second.
She grabbed me by the hair and said "Suck your Mistress you filthy whore!" I was stunned but didn't see as I had any choice so at first I didn't do anything.
Then she took her big cock in her right hand and pulled my head up by my hair with her left hand and started to rub her thick hard prick against my lips. "I think our little slut is being shy", she said to the audience.
At that point she reached down and attached a pair of alligator clips to the crown of my penis and held up a button for me to see saying "How do you like this?" and pressed the button. The pain was unbelievable, I thought I was going to pass out.
After the shock was over she said "You will suck me and you will like it or your prick will get zapped until you pass out from the pain."
I then realized that there was no other way and opened my mouth to suck Mistress Raven's huge piece of meat. Then she said, "Well slave how do you like it now?" I answered terrified, "I love sucking your sweet cock Mistress Raven!"
I slurped and sucked and took it all the way to the b
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