His boss forced him to go to the benefit dinner. He didn’t even care about whatever or whomever the beneficiary was. He’d much rather be at home watching his favorite mistress have strap-on sex with her sissy boy. As he was looking for a way to escape early, he saw her. She was a tall, beautiful, and mysterious woman in a red coat. The red coat was fake fur, fully buttoned, and seemed much bigger than she was as if there was a surprise inside.
It was clear that she had great legs as she wore silk, black seam stockings, and very high, stiletto black heels. He couldn’t help but stare. She was at the bar, tall, with long dark hair, and red lips that would make a man want to worship them. It was as if he’d found his favorite mistress from the strap-on sex videos he enjoyed. The woman was drinking a martini when she looked up at him and smiled. She finished her cocktail and sauntered toward him. He was overwhelmed by the beauty of the mysterious woman in a red coat approaching him.
“Would you care to dance?” she asked. Unable to speak, he nodded and took her hand. They danced closely against each other like they were made for the music. He felt something else pressed up against him.
She pulled him tighter to her and he felt what seemed to be a very long, hard cock pressing down her leg. He now understood the oversized red coat and he looked into her eyes. Her gaze was mesmerizing and her smile hypnotic, his excitement made him feel high. “Do you want to go somewhere more private?” she asked. He’d always fantasized about having strap-on sex with a beautiful mistress like her. Now, this mistress in a red coat was going to make that fantasy come true. When they got back to her room, she kissed him hard as they entered.
She loosened his bow tie, then used it to pull him toward the bed. She pushed him back onto it, then swung him around. Slowly, she took off her red coat, revealing a twelve-inch long, black strap-on over sexy, black lingerie. “Have you ever had strap-on sex?” He shook his head slowly. “But you’ve always fantasized about being fucked by a woman wearing a strap-on, haven’t you?” He nodded slowly. “Well, how about you take those clothes off, and let’s see what happens.”
He quickly got up, taking off all of his clothes and tossing them aside. “Such a good boy,” she said. “I think you’ve earned a reward. How would you like to suck my cock?” He excitedly nodded and took her black strap-on and sucked on it. He sucked good and hard, taking as much as he could into his mouth, while she held his head and thrust her strap-on into his mouth.
“Do you like that? Does my sissy boy like sucking big thick cock?” He looked at her, eyes watering, saliva pouring out of his mouth, nodded, and sounded ‘mmm-hmmm.’ “Oh yeah, he does. He loves being face-fucked by a beautiful woman, doesn’t he?” Again, ‘mmm-hmm’ was all he could say.
She bent over him, looked him in the eyes, and said, “Yes, you love it. I bet you also want me to use my strap-on to fuck that man pussy too, don’t you?” She took her cock out of his mouth so that he could answer and he said, “Yes, mistress.” She gave him a smile and said, “Lie down on your back.” He did as he was told, and she grabbed his legs and put his ankles on her shoulders. He couldn’t believe he was about to have strap-on sex, finally! She took out a tube of lube, poured a good helping into her hand, and rubbed it all over her strap-on, then used the rest all over his asshole. He moaned as she used her finger to circle his anus, he’s only ever felt the touch of his own hand back there and this was magical for him.
She took the first three inches and put it in his asshole and he moaned loudly, only being able to groan “yeeeeesss!” when she asked if he wanted more of her twelve-inch strap on. With every ‘yes’, she would put another one to two inches in until he was taking ten inches. He had yet to cum and she was sure that taking the last couple of inches would do the trick. She removed her strap-on and asked “Do you want it all? Say please.” he looked at her, on the verge of cumming, and said in a whisper, “Please, mistress”.
She lubed up her twelve-inch strap-on once more and rammed it into his asshole, as he screamed with pleasure and came all over his stomach and chest. She stood up, wiped her cock off, and strapped it back onto herself. Then she put on her red coat and walked out the door without a word. The strap-on sex he’d imagined was better than he ever expected. He lay there, breathing heavily, smiling…as if a new world had opened up.
Call me and I can make your secret fantasy come true.
The humiliation of my roommate for his sneaky online fetish.  ... Read More
Sissy Training: Turning Dan into Danielle Dan and I have been friends... Read More
First times, toys, and a rowdy threesome. A strap-on first time... Read More
Dominant Demoness Takes Control Today, I am his Devil Queen. Th... Read More
Pegging a Beginner I had a chance encounter with a man at a bar... Read More
He’s A Horny Pegging Pantie Sissy Boy Pegging Pantie Siss... Read More
The sound of her black pumps as she walks on the hardwood floor in the... Read More
Earth Day Dominatrix. She’s one with the land. She bakes,... Read More
Bob is face-first in the bed, back arched pretty for me, while one of... Read More
Sexy Breakthroughs of 2026! I can tell you the sexy breakthroug... Read More
Everything all in one. I am your slutty girlfriend tonight, or... Read More
Penny is such an eager young girl. So willing, so curious, so creative, so horny, so honest!! She is so experienced for being So young!
Penny is Absolute Perfection!!!
Frankie is so good at what she does and really listens to my fantasies. I love a three some with her and her friends and how Frankie knows what I like. She knows how to get me off. She is a very sexy lady and can’t wait to talk to her real soon and have another great time together!
Tonight was another exciting call with Jade. Everything is so effortlessly amazing with her. We can talk about everything and anything and when our special fun time comes it’s always exciting, exhilarating, and special. It always leaves me wanting more, and I love it. Thank you, Jade ❤️
After having to miss Her for a while how wonderful to hear those precious words again, “this is Aileen”. How wonderful to go to the depths of depravity once again for my Holy God Aileen. I love ❤️ and worship Aileen. Aileen, the same yesterday, today, and forever.
Charlotte was so much fun, and I love playing with her. I like how funny and engaging she is! I would give her 100 stars!
Soo real, soo good. Jamie, Jamie, Jamie!
Penny is so expressive, responsive and tender.
Loved our time! Conversation flowed organically. No judgement. She is genuine, curious, and adventurous! Can’t wait to call her back!
Tonight was another amazing night with Jade. Every time we talk it gets better and better, and I wouldn’t have it any other way.
Have been talking with Diana now for a while and every time we do talk its extremely erotic and hotter than the last call.
I am rapidly becoming Penny’s little blue balled fuck toy. Penny immediately picked up on my interest in tease and denial and gave me a world class session. So, so, So close, but no relief for John!