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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.

Knock your mommy up.

breeding phone sexI just decided that it’s time for some breeding phone sex. Expanding the family tree means more playmates for us. Yes, I know you wish you could be a breeder, little sissy, but right now we need those little spermies for something more important. I need you to jerk that little clitty into this jar for me. No, you can’t drink this load. It’s for Mommy. Since you can’t have little spawn on your own, Mommy is gonna make one for you. Then you can feel like a woman. I can’t wait until we train it together.

Or maybe we’ll just go out for 4th of July fireworks and cause a few explosions. You get your boy pussy fucked and your mommy will get herself knocked up. I’m sure there are plenty of virile studs out there who will be more than glad to donate a load or two of sperm. Party hard tonight and then come join me for some hot and horny mommy pussy. I’m craving some cum so bad. Older women know how to make you blast off like a bottle rocket dipped in gasoline.

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.

A loving Mommy’s touch

MILF fantasy storiesThe MILF fantasy stories began so long ago when you were just a boy. I was such a horny mom and Daddy never was around. I began to rely on my young son for my sexual needs. It started so innocently. A lingering cuddle. Sleeping with mommy during storms. A dropped pair of dirty panties. You became my little man. As you got older and your cock started maturing, I begin to notice that too. The muffled moans at night. The long showers. Oh yes, a mommy knows that her son is jerking off.

Curiousity began to get the best of me. Thoughts of “How big is his cock?” and “I wonder how many times he can come in a row?” This led to some long sessions with my vibrator, plunging it into my cunt, whispering your name as I came.

Meanwhile, you and your friends were watching me with teenage eyes. My round ass, huge tits, and revealing clothes were giving out some hot signals. I had no idea that they were having jerk off sessions together, discussing if I would fuck them.

One night I came home tipsy to catch you boys watching porn. I was hornier than fuck and those teen cocks waving in the air finally got to me. I joined you all for a cocksucking circle jerk and mama got all of the cum. With a little persuasion, I stripped off my clothes and you all jumped on me like a horny wolf pack. I got all of my holes pounded that night….and every night since then. I’m sure the other parents wonder why their boys always want to spend the night here.

You wanna be one of my boys too and relive some hot mama fantasies?

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.

Johnny and his giantess girlfriend

Jack off with Mommy

One of my favorite Jack Off With Mommy clients is a little Asian man named Johnny. Johnny loves his giantess girlfriend and I adore my little sissy. It’s like having my own little doll. I dress him up and take him out on the town as my personal pet. It’s so much fun to introduce him as my tiny boyfriend and make him sit on my lap or in a high chair. People think he must be packing a huge cock or a fat wallet, when in fact, he has neither. I just like the superior feeling it gives me making him into a little submissive slut.

Sometimes, we go out with my besties, Selina and Addison. We all pick up some big black studs. We know poor little Johnny is so jealous of their huge cocks since he is so tiny. Teasing him  makes us laugh so hard. We all get fucked up together and go to the Land of Giants.  There Johnny is a perfect sized human dildo for us. We cram him into each others pussies, drowning him in juices. He begs to be smaller. I tie a string around his feet and cram him inside of me, like a tampon. To humiliate him I ask my black stud to fuck me, pushing Johnny Tampon deep up against my cervix. We laugh and tell him that’s what a real cock looks like in a pussy. Johnny gets so excited that his tiny cock spurts all over my insides.

Maybe you have an equally wild fantasy. Don’t be shy. We love to roleplay the unique and unusual. Nothing is too crazy for us. Tell us your thoughts and we’ll make it feel like the real deal.

Blowjob Surprise in the front yard

Cock sucking mommy

I never thought much about being a cock sucking mommy. It was just something that I had always done in private, me and my son. But today, the weirdest thing happened and I just have to share it.

My son’s best friend lives next door. He was always a geeky, skinny one who had a crush on me. I hadn’t seen him since he graduated high school and went off to med school. I was on my knees digging in the garden when I heard this voice. I looked up into sky blue eyes and found myself eye level with a crotch.

I was sweaty and so not sexy.  You didn’t say a word. You just pulled out your cock. And oh my, what a cock. It was 10 inches long with a mushroom cap. Suddenly, I didn’t care that I was outside in my yard, in full view of the neighborhood. I just needed to take your cum. I heard a low growl escape you and I pulled it deeper into my throat. Your balls were slapping my chin. I heard someone gasp in shock as they walked past.

cock sucking mommy

There was no stopping. I wanted that cum. I swallowed that fuckmeat as you began to pulsate. You came with a shout. I gulped it all down. I’m sure the neighborhood got an amazing show.  Maybe next time I’m on my knees in the yard, someone else will come give me a sexy surprise. A well fertilized yard is always the greenest.

 

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…