He’s in his 50s now and married for many years. No one knows his secret, not even his wife. So, obviously, his first public crossdress experience was a big deal. To his wife, the garage is the “man cave”, but to him, it’s his private girly safe place. Thankfully, his wife stays away. Over the years, he’s continued to collect more things to make him really feel like his female alter ego, Lisa. Now he stocked a room full of clothes, lingerie, jewelry, makeup, and his favorite black wig.
Surprisingly, he’s never even sucked dick before his first public crossdress experience! I got to say, I’m very proud of him for finally letting Lisa have some fun. He planned a weekend getaway, but he had no idea that he would unleash his inner cock obsessed sissy. As far as the wife knew, he was going to do some work. However, this Vegas trip was all for pleasure.
Since he was doing this for so long, his female personality was perfect. She loves to wear her red wig, silky nightgowns, nail polish, bracelets and anklets, eye shadow, eye lines, fake lashes, sexy bras and panties, and of course, a padded bra to tie it all together. He left the house in his regular man clothes. Uncomfortable button-down shirt and khakis. Of course, he wore his cute panties underneath.
Finally, Lisa was ready to play. He put the contents of the suitcase away in the closet and drawers. The perfect outfit for the first public crossdress was laid out on the bed. Finally, it was time for the sensual ritual. The evolution from Josh to Lisa. Underneath, a purple padded bra, purple lace panties, and matching purple stockings. Over that, he wore a cute, tight silver dress and 2-inch heels. Full face of makeup, all nails painted, and her wig. She felt beautiful.
Lisa checked herself out in the mirror and was filled with excitement, confidence, and determination. She cleaned up the room, grabbed cash, and went to the elevator. Several people passed by some even checked Lisa out. When she got to the casino floor, she looked around at everyone enjoying themselves. such a powerful moment to stand in a room full of strangers for her first public crossdress. Now it was time to figure out what to play, how much to gamble and see if there are any cute single boys around.
Happily, she sat next to him. It was clear he was a bit drunk. He slurred his words. They exchanged flirty eyes as they continued to gamble together. She couldn’t help but wonder if this guy knew that there was a dick in her panties. Lisa truly passed as a woman. After a few rounds of poker, the guy started to rub Lisa’s thighs. Before they knew it, their hands were all over each other.
Soon enough, they got to Lisa’s room. They went into the room and started making out. Both their dicks were hard, although the dude didn’t notice Lisa’s. This first public crossdress turned into the first dick in her mouth. She happily gave him a blowjob. The cock grew in her mouth and finally, she tasted cum.
I love making my sissies happy 😉 I’ll make sure you get fucked really well! Let’s play!
xoxo
I have a feeling my Closet Sissy Needs Daddy Without a doubt, e... Read More
Sissy Training: Turning Dan into Danielle Dan and I have been friends... Read More
You would look pretty in my silky panties, babe! Is that your fantasy?... Read More
Sissy Training Fun Hello, naughty ones. I had so much fun recen... Read More
That Little Shrimp Between Your Legs Deserves Punishment… ... Read More
Heels Are Always Part of My Rituals When you worship at the alt... Read More
My Naughty Panty Boy Loves to Play Are you willing to be a good... Read More
Symbols Of Your Servitude… You know the truth by now: you... Read More
Sissy Training Guide II Welcome back to Katrina’s sissy training... Read More
Sissy submission between Mallory and her sissy boyfriend. I stepped in... Read More
Sharing Cock is Such a Treat! There is nothing I love more than... Read More
Come Shopping with Me Underwear Fetishism was something I thoug... 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!
