Sissy Strap On Stories
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Sissy Strap On Stories
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cdCindy1
on November 24, 2021 at 5:47 pm
Roxie
on November 24, 2021 at 8:43 pm
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Chastity
Mistress Phone Sex
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I first chatted with Tatiana a couple of months ago when she contacted me via Skype. She said she had seen my profile on Sissy School and asked me if she might “bother” me with a few questions to see if we would be compatible for a session or even ongoing training.
I quickly realized that Tatiana was already very well trained and was very well versed in most sissy-related things. She could put together a pretty outfit, walk in high heels and follow instructions. Also, at the time she was participating in Locktober and had plans for No Nut November. No wonder she found herself dreaming about sissy strap-on fantasies!
Best of all, Tatiana told me that her manhood had been stripped away after years of training with other Mistresses through Sissy School. And she described herself as “ incredibly submissive and a good student .” But, she was still in need of sissy training and humiliation with someone who is strict by nature. She had read and liked my blog and said that she thought I might be a good fit. And I agreed!
After a few sessions, I got the following excited messages from Tatiana – “Omg! Ms. Roxie, I had such a wet dream with you in it that I woke up leaking! And my aching clit is desperate for release.” I, of course, thought that was great! And so did my ego… Apparently, in Tatiana’s strap-on fantasies, I was super sexy and a total badass. And I was wearing thigh-high leather boots and carrying a riding crop. So, do you think I actually wrote a whole blog post about this dream? Of course I did!
I invited Tatiana to tell me all about it at our next session and it really was a good dream. She started off by saying that “it was an obscure dream but it felt so real. We met at a bar and the next thing I knew I woke up in a dark red room and felt a tightness around my clitty. I looked down and I was in a tight pink chastity belt!”
I jokingly commented that a dark red room sounded both sexy and creepy. And she told me to be quiet and let her finish the story. I’m joking, of course. Sissy Tatiana would never speak to a Mistress like that – especially when describing her sissy strap-on fantasies! Anyway, she said that the next thing she remembered was me, Ms. Roxie, coming out into the red room with the aforementioned leather boots and riding crop plus a black leather corset.
I then demanded that she get dressed up in what I had laid out on the bed. It was a slutty French maid outfit with 6” heels. It was the whole sissy production; panties, bra, fishnet stockings, wig, makeup, and the outfit. And finally, I told her that something was missing and gave her a breastplate that must have had at least size F breasts. And to make them even more noticeable, they had very large, protruding nipples.
After getting fully dressed and locked up, I had her clean my house. Now, those are my kind of sissy strap-on fantasies! Upon completion, I called her into my room where she found me wearing a huge thick strap-on which looked to her like it was nine inches. I started by having her suck and gag on it and eventually flipped her over and started to fuck her sissy pussy . And “that’s when I woke up,” Tatiana said.
I told her that her dream was extremely hot and also that I had noticed that I never actually used the riding crop. That it must have just been for show. But Tatiana said that I had in fact used it – to spread her legs before I started using the large dildo on her. And that I used it several times to tap on her pretty pink chastity cage. As any good Mistress in sissy strap-on on fantasies should!
Well, my sexy perverts… What did you think about Tatiana’s dream? It was pretty hot, huh? I think I came across as pretty badass too… And, to my knowledge, it is the first time anyone has dreamed about cleaning my house.
She is thinking about writing a blog post for me, which I think is a great idea. She’s already tossed out one idea to me – something science fiction related. Sci-Fi and sex are a great combination!
I’d love for you to leave me a comment below letting me know your thoughts. About this sissy strap-on fantasies blog post or anything else you want.
Can’t get enough? Craving more? (Of my blog) – here is a good place to start :
Now that you and I have had a few calls which have truly been wonderful, I had my first dream about you last night. After our calls yesterday (including the 2 mistress dick pic review), your beautiful and sexy presence appeared before me. You were dressed similar to this blog post with black leather boots and leather corset (but red not black, to match your hair). I was dressed in my sexy lingerie, a French maid’s outfit, blonde wig, high heels and make-up.
The interesting part of this dream was that my wife was standing next to you. She had a big smile on her face because you had just told her that her sissy husband is a faggot cocksucking bottom bitch. You told her that the big black strap-on you were wearing was for me to show her how good a cocksucker I really am. I was both humiliated but also very excited to have you help me to finally come out to my wife as a sissy faggot and to also tell her that I want to be her cuckold.
The rest of the dream is you showing my wife (with your boyfriend’s assistance) that I suck real cock (and I’m quite good at it), that I swallow cum, and that I can take a big thick cock up my sissy man-pussy. You cuckold me with your boyfriend and teach my wife how to do it so that I can eventually become her full-time cuckold husband. She thanks you for exposing her gay husband’s secret and for teaching her how to control me. I also thank you for doing so.
We can talk about this further in our next call. I can’t wait.
Until then, I remain your loyal sissy faggot bitch,
cdCindy XOXOXOXOXOXOXOXOXOX
Wow – that is quite a comprehensive dream. Your mind covered a lot of ground! It’s nice that even in your dreams you take the time to wear a pretty outfit and do your hair and makeup. It’s the little things… And I’m happy to speak with your wife at any time and reveal all of your dirty secrets to her. My usual rates apply Lol ????
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A strap-on punishment is precisely what he was asking for. Really, he knew the rules. Poor little Joey knew he was putting his ass on the line when he talked back to me. He knew his role in my house is to play a sweet, subservient little sissy bitch called Jenna. I picked that name out for him, and he has loved it ever since. However, something got into his head that made him think he was a regular alpha male. I couldn’t let that be. If I let him keep thinking that, he would fall entirely out of touch with his feminine side and all the things he enjoys as Jenna. So while he broke several of my rules and deserved punishment, I was also looking out for him.
What more could I do? HIs little ass begged for a spanking. His little rebellious streak came in one day after he’d spent the weekend with his guy friends. It was a treat for him. I allowed him to go out and enjoy himself and have some drinks with the boys. His friends, of course, are oblivious to all the pink lace and makeup that he likes to wear at home. It’s his little secret. However, when he came back from his weekend adventure, he forgot how to act! He failed to call me Mistress, and he even wore his regular clothes around the house. I couldn’t let that stand, so I told him to change. That’s when he first backtalked.
He was my little sissy bitch. I could not let him backtalk me and walk off as if nothing happened. So, I instantly opened one of my drawers to grab this big wooden panel. I specifically picked the one with all the studs on it, knowing that his ass really needed a special kind of beating today. At first, he resisted even that. Though he was craving that spanking, he was a misbehaving sissy, and he needed a much worse punishment. I started with his flogging, yanking his pants down forcefully to turn his cheeks bright pink with traces of red. The studs on the paddle always left little welts that he loved to feel. It would leave him struggling to sit down for at least a week.
However, we both knew that wasn’t enough. So I led him along to the bedroom, where the real fun was waiting for us. As soon as we stepped in, the roles rightfully returned. He knew I was coming up with a strap-on punishment for him. I ordered him to go strip down and lay on the bed on his stomach. He did just as I asked. Once I grabbed my toys from the closet, I ordered him to prop himself up on his hands and knees; ass presented to me. He did just as I asked and later held his cheeks open for me so that I had clear access to his little butthole. A strap-on punishment was coming for him, and he knew it. He’d been craving one all along, or he wouldn’t have mouthed off like he did.
As I lubed up the head of the strap-on, and his tight little ass, he couldn’t hold back his moaning. He was craving it. I bet he daydreamed of fucking his friends and of getting them to fuck his ass as hard as I did. The second the head of my cock slipped against his cheeks, he grunted in sheer delight, and I rammed the strap-on in. It stretched him out with every inch. I picked my biggest cock to fuck him with. It was a solid twelve inches, and thick all around, at least two inches in diameter for the girth. The big, bulbous mushroom head was stretching his ass out every time I entered him.
I made sure I pulled out every inch of it, just to torment him. The head came out with a delicious POP every time, and I’d ram it back into him just to make him sore. I even taunted him about taking videos and pictures of it, and how I’d send them to his friends. His friends didn’t know a single thing about him and his past-time as Jenna. However, Jenna loved the thought of all her friends finding out. She frequently daydreamed of all the humiliation phone sex she could have if they ever really found out that she was such a sissy slave.
I’d already taken him on a stroll around the mall to do some shopping. I paraded him in front of everyone. He loved being a humiliated sissy slut , and there was so much more left to explore with his fantasies.
Kali is a sexy, young latina raised in Los Angeles.. She uses all her gifts to tease the guys, making them melt in her hands just from hearing her sweet, silky voice. Seducing men double her age, or more - the older, the better. She'll use her soft lips to whisper little temptations to you in Spanish. You'll find yourself daydreaming, aching for the way she moans your name and pulls you into the darkest of your fantasies. No one has to know.. It will be your secret. Come indulge in the bad girl that you've always secretly wanted.. Want to see more of me? » Click here to go to my page.
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