Category Archive: Sissy maid training

Mommy whore Daphne wants you in her

mommy whoreI’m your hot mommy whore the one you just want to pin and fuck. I got home the other day and noticed my boy was rock hard. I walked in on him watching some good old fashion porn. I wasn’t surprised he was watching it. I mean a guy his age is thinking about fucking almost every second of the day. I instantly hopped on his dick and started to ride him. It was that fast I just hopped on and made him enter me. He was so excited and ready to bust his load. I made sure I stalled him for a bit. There’s no way I’m going to allow any of my boy’s  to be minute men. Oh no, thats not happening I make sure I teach them well. I have to help them build tolerance and I know its hard not cum when momma is rocking on that cock hard, but they need to learn how to get momma off first then they can explode. The only exception is if we cum together. After a couple minutes, we both climaxed and it was sort of a mess but he’s a good helper, and was able to clean momma up with his mouth.

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.

Sissy Boy Therapy

Milf fantasy storiesYou’re up late tonight. You’ve already jacked off three times but you need some Milf fantasy stories to really empty those balls. It’s time you talk to a real life mommy who gets what you really need. No amount of phone sex moaning is going to satisfy you when what you really want to be is a sexy slut.

Think of me as your phone sex therapy mommy. Having a sissy boy of my own, I totally get your needs. The way you want to dress up. I can even send you the perfect pair of panties. Nice and fragrant, to make you think of mommy. You want to please mommy, right? So put on those panties, grab that trainer ass toy, and let’s start this session.

Tell me about that cock you crave. Is is big? Do you want to be submissive and forced to gag on it or just allowed to nibble and tease? Does mommy need to stretch that pussy first with a dildo or strap on? Or are you an eager slut who wants that boy pussy pounded hard? One call with Mommy and we can explore your special needs. Your clitty will explode in those panties. Quit denying the faggot truth and come talk to me soon.

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.

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