Category: cross dressing

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.

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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.

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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” →

Rhonda 844-332-2639 ext 446

I’m a good wife. I decided to get a Holiday Gift for My Cuck. See, as many of you know, I am from a small town where the cheerleader married the quarterback and then got married, white picket fence and all that. Only, my jock husband had a terrible secret. His tiny dick was so disappointing. There was no way he could please me. So we came to the city and made him my cuck.

With Christmas coming, I decided to get him a very special gift. I started on a Saturday morning.  First, I dressed my 6’2″ muscular executive of a hubby in his cleaning clothes. I found the French maid outfit on eBay. Hard to find one his size. But I get him all dressed, watching his cheeks turn pink. Then I bent him over and plugged up his ass. Pulling up in white panties, I gave him a little slap on the ass and told him to get to work. I love watching him do the housework in heels, a French maid’s outfit, plugged up and so eager to please. Continue reading “Holiday Gift for My Cuck” →

Naomi 844-332-2639 ext 216

There is something I want to do with you. I don’t really care if you are eager for it, but being such a pathetic bitch, I know I can get away with doing anything to you I want. I want a Happy Little BBC Threesome with you, me, and a Big Black Cock.

I’ll invite you over first. So just you and me alone, knowing what is going to happen. I might dress you up in thigh-high stockings, a short skirt, and a pink bra under a white blouse. No panties, of course. We don’t want anything in the way of your BBC, do we? Look at you, all pretty and dressed slutty for your new lover.

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Miqala 844-332-2639 ext 447

I absolutely love Dressing Up My Sissy Girl. See, I know you. The real you. Yeah, sure, you dress like a man and act like a man around other people, but we both know that’s not the real you. The real you is more tender, delicate, and perhaps a little shy. It won’t happen when you are peacocking like a man. No, when you show everyone how strong and dominant you are, a part of you is breaking, crumbling, because it’s all fake. You are a fake man. I know what you really are, and so do you.

You, sweetheart, are a sissy at heart.

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Rhonda 844-332-2639 ext 446

Want to Play a Kinky Game with me? Let’s do it. We’ll get all comfortable, curled up on opposite sides of the couch, and stare into each other’s eyes as we share a drink or two. We’ll play “I Never,” perhaps. Have you ever played?

It’s easy. I’ll mention a sexual position or maybe an exciting excursion to explore sensual fantasies, and you’ll tell me if you have ever done it. You must tell me if you’ve thought of it if you say I Never. Then you can do it back to me. See, Easy peasy. And as we share libations and relax more and more, the deeper secrets we’ll spill. Continue reading “Want to Play a Kinky Game?” →

Rhonda 844-332-2639 ext 446

Rhonda Cheating with Permission is fun. Though, saying I have permission is a bit of a misnomer.  My husband had no choice but to acquiesce. Out there in the big world, he is a powerful man who can boss his subordinates around, but not here in the house. See, he has a terrible secret. His dick is way too small to bring me any pleasure. He knows this, I have reminded him of it often. So, I cheat. And because my husband is too weak and pathetic to stand up to me, that means I have permission.

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