Category: cross dressing

Babysitting Silky

Valerie 1844-332-2639 Ext 243

One of the greatest parts of being a babysitter is exploring the world of make-believe and fantasy! When I’m babysitting, we can play dress up and be whoever we dream to be. That’s what happened when Silky’s mom asked me over to sit for them. When I arrived, Silky suggested we play dress up because her mom had a closet full of beautiful, soft things. We tiptoed into her mom’s beautiful room, I looked over the vanity which was lined with expensive perfumes and lipsticks as Silky pushed open the closet and showed me all of the beautiful pieces of lingerie and robes in all types of delicious fabrics.

I could see Silky’s eyes growing wide as I asked her to show me all of her favorite things. She shared with me that her mom didn’t know she liked playing in her pretty things, and I told her that the secret was more than safe with me. We’d clean up and put everything back in perfect order…after we had our fun.

Continue reading “Babysitting Silky” →

Little Clitty

Posted 8 months ago by Writer

Alex 1-844-332-2639 Ext. 425

I can see what you have going on in that pair of panties. When you bend over, showing that little sissy ass off for me to look at. You know that I like to see how slutty you look bent over like that, ready for me to pimp you out and make you my own little sissy attraction to the cocks around the world. It’s not just me that can see it, and it isn’t a bad thing by any means. That is the one thing sissies have on us ladies. A nice, engorged clitty ready to be rubbed and toyed with all night long.

Continue reading “Little Clitty” →

Mercedes 844-33-CANDY Ext 423

 I knew you were weak when I first met you. You were so eager to please me, to do anything to get in my pants. And now, I finally have you right where I want you: on your knees, begging for my cock. You have it in your head that it’s my pussy you’ll finally be tasting… but you won’t be getting that tonight. Oh no, I have something much better in store for you. I pick up the strap-on I bought earlier today, the one with the thick, veiny dildo attached to it. I slip it on and adjust it, making sure it’s just right.

Continue reading “Wanna Have a Taste?” →

clothes

Anna 844-332-2639 EXT. 203

Mommy Anna sat her Sissy Slut Bob down. She said they needed to talk. She told him that he needed a new wardrobe. ‘’Gotta look the part baby, your clothes are tattered and torn’’. ‘’You’re right,’’ said Sissy Slut Bob, ‘’my clothes have gotten torn up and ripped from being such a good Sissy Slut for you. I could use some new outfits.’’ ‘’That’s right,’’ said Mommy Anna ‘’And you gotta look nice so you can go out there and make me lots of money!’’

Continue reading “Sissy Slut Bob’s Shopping Spree” →

Miqala 844-332-2639

Every PSO has calls they really enjoy. I had an amazing call recently, and I want to share. I love Breastfeeding my Baby. Sometimes I get babyboys, other times, babygirls. My recent call was a babygirl.

He came to me as a man, so I started by stripping away his clothes one item at a time. Reminding him how I am stripping away his adulthood and his manhood. I could feel him surrendering to my soft Mommy voice, his voice becoming softer and lighter, and I started seeing the babygirl coming out.

Continue reading “Breastfeeding my Baby” →

Sherry 1844-332-2639 ext 399

It was Friday, it’s been a grueling week and the nights have been long. I decided to take my time tonight.  Something strange was in the air this evening. I could almost taste him as I walked along the sidewalk. I closed my eyes took in a deep breath and started whispering in his dreams. His scent made me quiver in delight. Continue reading “Chronicles of Sherry- Training Day – Part I” →

Sherry 1844-332-2639 ext 399

It’s in the middle of spring walking along the parkway. I am wearing a stunning purple strappy sundress and tan wedged heels. My hair was all curly and pulled up in a sexy bun wearing my glasses. I can smell the manly musk in the moonlight air, wondering where it will lead me too. The night is still so young, should I give in to my urge or should I wait?

 

Continue reading “The Park Bench” →

Rita and Avery Put You In Panties

Robotic Rita 1844-332-2639 Ext 413

As soon as Avery and I discovered you had a tiny little stiffy, we forced you into panties. We couldn’t stop giggling because you were so flustered and nervous by two hot brunettes pushing you around. It was easier than it should have been, honestly.

When Avery said you were cute and I touched your arm, we almost thought you would cream your undies before we put you in panties. It was my idea to peel off Avery’s panties; I just slinked them down her legs under her short skirt without revealing any of her sweet pussy. Even though you wanted to see it so badly! You know you’d never even have a chance with either of us, so you let us bully you!

Continue reading “Rita and Avery Put You In Panties” →

Summer Fun

Avery 1-844-332-2639 ext. 228

I am so ready for some summer fun this year! And since it’s officially summer that means you need some sissy dress up time so we can update your wardrobe. It’s the time of year for pretty summer dresses, bikinis and super, tiny shorts. Just think about how many guys you could attract by showing off those sexy legs of yours.

Do you wish a pretty girl like me would dress you up and teach you how to be a sissy slut? One of my favourite things to do is totally transform someone from a masculine guy into a pretty woman. I mean, you won’t be as pretty as me when I’m done with you, but you’ll definitely be passable once I work my magic.
Continue reading “Summer Fun With My Sissies!” →

Miqala 844-844-332-2639 ext 447

Hello, sissy darlings. So, I had to fire my housekeeper, and I’ve decided that instead of hiring the same old/same old type of maid, I’m going to indulge my feminization fantasy. And that means I need a new sissy maid! Do you want to Be My New Sissy Maid?

I am very particular about my household cleaning, and because of that, I go through housecleaners rather quickly. It seems like this is the perfect opportunity to indulge my kinky side and get my house cleaned, too. So, do you think you have what it takes to wear that French maid costume and clean my house from top to bottom?

Continue reading “Be My New Sissy Maid” →