Tag Archive: sissy maid training

Breeding whore mommy

wet mommy pussyBreeding whore is what I have always been and now my boys are in on a serious bet. They want to know who can fuck momma the hardest and the best. Most importantly they want to know who can impregnate me the fastest. It has been quite the journey and the whole thing has barely started. I was up last night fucking for a total of 7 hours. This momma is totally exhausted. I have been getting cock after cock. With little to no break. I have been pounded at all hours of the day. I really believe the mission has been completed. Now it’s only a matter of time to see who had the winning swimmer. I should have known this would play out this way my boys are such fierce competitors. They are addicted to fucking me. It started out with just eating me out and me rubbing and sucking their cock. I would eventually rub my tits on their cock til they ended up cumming in bliss. Now it’s getting more extreme and they are enjoying ejaculating inside mommas cunny. I have my bet on who is going to win the challenge but I am also very excited to be participating and reaping the benefits of my boys hard ons.

Panty Training

Sissy boy mommy

You just needed a gentle mommy’s touch to bring out your inner faggot. You were so shy and barely mumbled when I asked how I could help you. I told you by the hand and looked you in the eye. “Do you want to be a girl?” You nodded, looking at me with your luscious eyelashes. I could already imagine your slender body all dressed up as a girl. Your round ass clad in sating bikini panties. You would be a knock-out. Men would be lining up to have those full lips wrapped around their cocks or to push throbbing fuck sticks into your tight little boy-pussy.

I felt my own cunt twitch a little as I handed you a pair of panties. You tucked your teeny weenie and little shaved balls into them and you were transformed. It was time to bring out my special tools to make you into the sexy cock slurping whore that I knew you were. “Pull down your panties and show me your pussy.” I ordered, slipping my strap on over my own panties.

Put these lace panties on and confess.

sissy boy momI’m a real life mommy but being a Sissy boy mommy is my favorite role. Guiding little faggot boys into being girls makes my pussy wet. You just need a little guidance, young sissy, and soon you will be what you’ve always known you are.

I pulled the strap on over my panties, marveling at my huge cock. You were bent over in front of me, trembling in fear and arousal. “I’ll be easy.” I whispered, as I pushed my fat cock head against your pucker-pussy. You gasped just a little as I gave it a nudge, opening you. I squeezed your round ass cheeks as I shoved a little deeper.  “Squeal for me, sissy. Tell me what you need.”  You gave a little faggot moan and arched that pussy higher. “I need fucked, mama.”  “What do you want?” I demanded. “Cum. I want cum. “Louder.” You squeaked louder. “Please. I need it so bad.”

I pumped that little bitch until your boy pussy was raw and you loved it. Now pull those panties up and feel the cum seep from your wounded hole. It’s time for round two.

Mommy does BBC training

Jack Off With Mommy This will make you Jack off with Mommy for sure. I got a sample of the fun we’re going to have in our sissy training class. I hand picked some big black studs who love to break in a new sissy pussy. Oh, we’re talking 10 inches of throbbing nigga meat. I’ll have you all dressed up for your first date with them. Mama will get down on her knees to demonstrate the techniques you need to learn. You better get that big dildo out and practice stretching that boy pussy so you can accommodate this much girth.

Bend over, little sissy, and show us your faggot hole. My nigga wants some of that cherry. It looks so tight. He’ll make you squeal like a real girl as he humps that pretty ass. Let me demonstrate on how to eat this much cum. These guys are known for their potent semen. Open that mouth wide, you’ll only be able to gulp that first squirt. Let it dribble over your lower lip, down your chin. Stick out your tongue and show him his cum. Now swallow and smile like a good faggot slut.

You’re almost there. Now bring an ass toy and let’s practice stretching your new boy pussy. Soon you’ll be able to handle unlimited meat sticks all night long.

You say Sissy like it’s something bad.

sissy momI’m not your regular old run-of-the-mill mommy. My specialty is tranny girls, sissy boys, and playing dress up. Plus good old fashioned spankings for naughty boys. When you need a real mommy with experience, you need to come get some tutoring from me. I will make you into a real life sexy slut. I love getting your pics and showing you exactly what you can become. Bring a toy for our calls and we’ll stretch that new boy pussy to handle the biggest cock. Mmmmmm, I know you love cum.

So, go raid your wife’s or daughters panty drawer. Or order some from me to play in. This mommy is going to teach you the ropes. Don’t be shy, little sissy. I can tell from the way you walk that you’d make a natural slut. With that round little ass and cock sucking lips, you’ll get more cum than you can handle. All you need is a little training and you’ll be on your way. I’m your new non-judgmental mommy and I will bring out the best in you. Don’t be shy. Share your fantasies and come get off with me. I know that little clitty needs some attention.

Show me those panties!!!

jack off with mommySometimes you just need to Jack off with Mommy. I’m a sissy boy mom. I love taking you wanna-be sluts and making you into cum slurping little faggots. I know you steal my panties or maybe your own mama’s, or your wife’s. They have no idea on how to deal with a sissy like you, but I do.

One call with me and I will own your little faggot hole. I’m sweet to my newbies but I won’t be so easy when it comes to breaking in that pussy. It’s your secret desire to be a girl and I plan to Ass-ist you. Here’s my orders. Shave those legs and those nasty fuzzy balls. Steal some panties or I can sell you a pair or two. Grab your butt plug, dildo, and lube. And you will also need a glass.

We’re going to have a roleplay and it’s gonna feel so real. I will tease and demean you, gently at first. Once we get that boy-pussy all nice and wet, you’re gonna fuck that pretty booty for me. Or maybe I’ll pull out my training strap-on. Then I will get rougher and call you names. You know that makes your clitty swell in those panties. When you can’t take any more, you’ll cum in that glass for mommy. Then I will give you two choices. Drink it like a good little cum slut. Or freeze it and make it into a cum-sicle for our next call. Yummy frozen cummy for my panty boy.

Come meet your new sissy mommy for that special training that I know you need.

Sissy Lessons with Mama Pearl

Sissy maid trainingSissy maid training classes are now in session, boys. Sign up now to learn to be that cum slurping little faggot that deep down you really want to be. In my special tutored classes you will meet our sissies who want to be just like you. Together we will dress up and do our make-up. You will transform from masculine guy to a sexy, flouncing girly-girl.

Lesson two will be playing with a variety of ass toys. Bring your favorites and show the class how much cock you can take. We got to get that boy-pussy stretched wide open. No man wants to fuck a cry-bebe faggot. You need to take that fuck stick to the hilt and love it.

Lesson three. We will practice on each other. Learn how to approach and flirt to get your needs met. Lots of roleplaying to get you feeling good and confident. Bring that sexy lingerie and those lace panties and learn how to rock them. High heel or stilettos required.

Lesson four is the best. I will have some sexy tranny-loving men with large cocks come in and show you how it’s done. I will fuck and suck and demonstrate on these meat sticks before I allow you to join in for your first taste of another man’s cum.

Are you ready to begin your new life as a tranny? Come join Mama Pearl for some therapy and education.

Late night Tranny fantasies

Sissy training phone sex

Just admit it. Sissy training phone sex is what you are on here looking for. You’re not just another hard dick looking to get jerked off.  You have some special needs and you want the perfect mommy to help you. Sweet boy, quit hiding from your desires and come tell Mommy. You see, I’ve known your kind before. My older brother and my own son are both sissies. I trained both of them to be cock sucking little sluts. I can train you too.

I mean, you’ve known from a young age what you really are. You are a closet faggot who hides the fact that you want to be a girl. You want to be dressed up. You want to be properly and gently trained. I want to hear those fantasies. I’m an older sissy mommy with experience so no shame, no judgment.

Your need to wear panties and lingerie doesn’t shock me. In fact, i will sell you some that are perfect for you. You also need an ass toy to start your training. Oh, it will feel so good and so right inside of you. My strap-on is also available to help you stretch that new pussy.

Quit trying to sleep when all you think about is cock. Bring it to Mommy and I will explore all of your faggot or tranny fantasies. You will be so pretty and fuckable.

Training my new sissy

jack off with mommy

Jack off with Mommy while I teach you how to be a sissy success. Mommy knows what ti takes to be more than just a dress up game. You have to become a real girl. A slut. One that can please men with your cock sucking skills and a love for cum.

“Mommy, how can I be a real girl.” you ask. “Can I wear your clothes?” Sweetie, it’s more than just wearing my clothes. Any boy can put on women’s clothes. You just look like a drag queen. You have to learn how to wear those clothes. I mean wear them like a woman. With class and a flounce.

And your cock sucking skills need work too. You look like a pig slurping at the trough. Any whore can do that. You need “the look” as well as the skills. Look at him with those big eyes, nibble a bit, leave him waiting for more. Now take that meat rod down your throat. Deeper. Oh yeah. Now gag just a little. Make him feel like a man. You’ll get that cum that you crave so much.

I can teach you this and more. Come on, little sissy. No one has to know your secret except us. Be the best sissy that you can be. Just reach out to Mommy…

 

Sissy training phone sex with Mommy Pearl

sissy training phone sexI’m ready to start your sissy training phone sex lessons. I’ve known since you were a boy that you were special. The way your sweet ass wiggled when you walked. The way you lisped your words. That little flounce when you were pissed. But it wasn’t until my panties started disappearing that I figured out the truth. At first I thought you were just like your older brother, stealing them to jerk off into. But I snooped while you were at school and it blew my mind. In a small set of plastic drawers in the back of your closet, I found your secret stash.

It was filled with beautiful lingerie and panties. I recognized some as mine and some as your younger sister’s. I had wondered what you spent your allowance on and now I knew. There was a box of makeup and Ebay receipts. My son was a sissy. OMG!!!  I snooped a little more and found one of my old vibrators. I put it to my nose and got a faint whiff of ass. I giggled to myself, thinking of you fucking yourself, wearing your panties. I quickly put everything away.

Tonight is ours, my sissy boy. Your sister is sleeping over at her friend’s place. Your brother has another week of college. It will be just me and you tonight as I reveal what I know. Tonight we will start your transformation into the cock sucking sissy that you desperately want to be. Mommy has a big black strap-on and a wicked smile on her face. Your secret is safe with me.

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