Category: cross dressing

Mila 1-844-332-2639 Ext. 220     Kayla Cumsalot 1-844-332-2639 Ext. 357

Mommy Kayla and I had a plan when my little brother came home. We were going to turn him into the baby sister I had always wanted! When he got home, our plan was set in action. Mommy Kayla and I always have so much fun together, and this was no different. He put his bag down once he came in the door and I made sure to wrangle him into submission for us. I did want a BABY sister after all, so first step was getting him into that diaper. I held his – ahem – HER legs up and Mommy Kayla slid that diaper under her!

Continue reading “Mommy Kayla Makes Sissy Baby Wish Come True!” →

Manipulative Rhonda 844-332-2639 ext 446

Do you know why men are cautious of me? The answer is easy. I always get what I want and do what I want. And right now, Rhonda Needs a Virgin.

Time for some age play, guys! I want you to remember what you were like when you were young and oh-so innocent, desperate for even the smallest amount of attention from any girl at school. Were you still a virgin in college? You’ll tell me all the details of what you were like. It’ll help you get your mindset to what I want—young, innocent, desperate, and easy to manipulate.  That’s when I’m going to do what I want to get what I want.

Continue reading “Rhonda Needs a Virgin” →

Sissy Shopping Spree

*LUCY* 844-332-2639 xxx- 221

I know you love wearing panties but when was the last time you really gave into your desires and had a sissy shopping spree? Because I definitely think you need to do it more often. I love all things lingerie so filling my closet with new, sexy things to wear is the best way to spend the day. So tell me, are you an experienced panty boy or are you one who’s looking for a new mistress?

I adore panties too and I would love to discuss your favorite styles, colors, fabrics, and all of those fun things. I wonder if we have some of the same favorite types. We could totally wear them together on calls. I have a very extensive lingerie closet so I’m sure we have a few of the same panty sets. I guess we’ll find out when you call me, and we get to know each other.

Continue reading “Come With Me For A Sissy Shopping Spree” →

Vivian 844-332-2639 ext. 254

Diapering my sissy next door neighbor is not how I thought I would be spending my Monday morning yet here we are. I wonder if his wife knows how naughty he is. He is usually so quiet and reserved yet he sure is a closet perv.

All I wanted was a cup of sugar to make a cake. I went next door expecting the missus to open the door and instead the hunky husband welcomed me in instead. The wife was out of town and Bobby decided to play hooky from work.
He’s a big flirt and as we did the whole small talk thing he peppered me with compliments. I came over in a robe covering sexy pajamas but when the robe slipped open I didn’t bother to close it. He had quite the view of my cleavage and my nipples were rock hard.

I didn’t want to tempt him too much. I am a naughty neighbor but I don’t want him to report back to his wife that I was disrespectful. I got up to leave and “accidentally” tripped spilling sugar all over both of us. As he jumped up and started to wipe sugar off his pants I heard that all too familiar crinkly noise.

Instantly I get excited. It’s been too long since I’ve played and I am going to take advantage. I apologize profusely and attempt to help. There goes that sound again and this time he knows that I know. Continue reading “Diapering My Sissy Next Door Neighbor” →

Zesty Zoey 1-844-332-2639 Ext 403

Our firm is full of high-powered female lawyers.  We wear power suits and fill the men around us with trepidation and intimidation.  In our firm, all the lawyers are women, and we only hire men for secretarial work.  Recently, we hired a new secretary.  He’s already on the right tract as he showed up wearing ladies slack, an ambiguous blouse, and ballet flats.  A week into his employment all the partners met to pull straws.  I pulled the longest which meant that I won and it was my turn to transform the male secretary.  He was about to become completely feminized.

Continue reading “Transform the Male Secretary with Zesty Zoey” →

Saving My Brother-in-Law

Mama Felicity 1844-332-2693 Ext 270

My Sister has been complaining about her husband a lot lately. He recently lost his job and has been moping around their house like a bump on a log. He isn’t looking for a new job and isn’t taking care of the house to pick up the extra slack his situation has caused her. She’s had to pick up extra shifts and is always exhausted.

While she was venting to me, I pondered how to help. I decided to go to their house the next day when she was at work. I’d have a little “talk” with my dear brother-in-law and see If I couldn’t set him on a happier path for their marriage.

Continue reading “Saving My Brother-in-Law” →

Jemma – 1844-332-2639 ext 303

For myself, the reason why I love being a pillow pal is because it can sometimes be a nice escape from reality. In my opinion, unlike traditional role-play and cosplay, I feel different. Due to the fact my head and face are completely covered by my pink unicorn suit.

Obviously, I don’t speak for everyone, but I think lots of people agree with me. Wanting to have a place where all my pillow pals could party with me, I decided to throw a Monters Inc.-themed party. Of course, dressing as a monster was not required, people could come in any kind of suit they wanted. However, I was hoping some people would come as monsters.

Previously, I had purchased every flavour of Ciroc, I had also baked a few monster-themed desserts. Although, the party would be catered. Not to mention, I invited about 100 of my closest pillow pals.

Once everything was ready, I was very excited for my guests to arrive. Completely blown away once they did, there were foxes, bunnies, birds, unicorns, and all kinds of different animals. Not to mention, lots of people came as monsters.

Continue reading “Jemma’s Monsters Inc Party” →

Mila 1-844-332-2639 Ext. 220

I was cleaning up a friend of mine’s place while he was on a work trip. Nothing crazy, just dusting and re-organizing his linen closet, doing some laundry. He was so busy and I thought that he could use the help! But when I clean, I like putting on some music. So I logged on to his computer to put on a playlist. But what do I come across? He left his browser window open on the last tabs he was on. And I couldn’t look away! This guy I have known for years loves to be a sissy baby. So I made a plan for the sissy baby I now had in my hands.

Continue reading “Sissy Baby Discovered!” →

Mila 1-844-332-2639 Ext. 220

I love babysitting my little boys! They’re always so respectful and listen to everything I have to say. Very obedient, they don’t want to make their mommies upset when I tell them how our day went! I always have a good time with them. Of course, when they are naughty they get a good spanking from Miss Mila and no goodbye game, but when they are good? Oh boy! I make sure they know they have been good. How else are they supposed to keep being nice little boys? Now, how do I reward them? Well, it depends on the boy. But, there are some constants in my games.

Continue reading “Babysitter Mila’s Games” →

Rhonda 844-332-2639 ext 446

Rhonda’s sissy slut phonesex makes all the small clittys hard. I love my sissy femboys who need encouragement from a Dominant Mistress! With you all dressed up and ready to tackle the biggest cocks is the right mindset. I need you to be in! Your back door pussy was made to be used. I really enjoy the sluttiest and stupidest whores around! I have a new one who I added to my stable of sissy ladies recently. Dirty panties and sanitary napkins for her fantasy aunt-flow!

Tampons shoved up her pussy are pre-used by me! I always surf the crimson wave very hard! This special Sissy, I’ll call Betty, has an ass that is so blown out that she needs to keep it corked! Little Miss Nasty, if you ask me!  Sissy Betty takes the tampon cardboard plunger and pushes that applicator up in there very deep! Her booty sucks it right up! Continue reading “Rhonda’s Sissy Slut Phonesex” →