Tag: jack off with 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.

Jack off with Mommy at the Yard sale

Jack off with mommy

It was a jack off with mommy annual event in our neighborhood. My annual garage sale. I’m not a hoarder so every Spring I clean out my closet and lingerie drawer and sell it all. It’s so much fun to watch my neighbors show up, trying to be all discreet. They creep over a few at a time. And no one ever tries to haggle. They know I have the good stuff. I even have a few used toys if you’ll just ask.

You were my first customer. I was watching you out of the corner of my eye as you held a pair of panties up to yourself. I stifle a giggle as you try to tell me that they were for your wife. Your wife is a 250 lb oinker so I know that these are for you. I always suspected that you were a panty boy and now I know the truth. “I think they will look great on you.” I whisper, watching you turn red. “Shhhh, it’s our secret. Just let me know when you are ready to model them for me. I love a man who wears panties. Would you like the matching bra, too?” You look like a fish outta water as you gasp for air. I know I’ll be seeing you soon.

By the end of the sale, I have a fistful of cash and a list of names signed up for sissy lessons. Wouldn’t you like some of my sexy things, too? You can model it for me and send me pics. Mommy loves little faggot boys who beat their meat into their panties. Your secret is safe so come share with me.

 

Sissy boy punishment

Sissy boy mommy

Someone has been a very naughty little boy, catching you jerking off without Mommy’s permission is very very naughty. First things first…we have to go to the store because you are out of diapers. I put you in the back seat and strap you into your car seat making sure you can’t get out. I have a cup of water in my hand and you ask for a drink. As I am handing it to you I “accidentally” spill the whole cup onto your pants crotch area and down your pant legs. “Oh my, too late to change your pants baby, we have to get going.”
We arrive at the store a moment or two later and the water on your pants hasn’t dried. I come to the back seat and undo your car seat and say let’s go into the store. You pull on my hand a yell no at me. My eyebrows go up in an “oh really” look at you. “Get out of that car right now young man, before I take you over my knee right here in this parking lot.” You start to step out and your pants…you definitely look like you’ve peed your pants. I grab your hand, walk into the store, grab a cart and make a B-line for the diapers. I grab about four of the biggest boxes they have and load them all into the cart. I grab your hand again and pull you along to the check outs. People are staring and even laughing. Think it’s at Mr. pee pants? Or that I have a cart full of diapers that you clearly need.
I put you into the back of the SUV and start to take your pants off. “What are you doing Mommy??” I give you a stern look and tell you that I am going to put your diaper on. The look on your face and the begging that came with it was quite a lesson for you. I get the diaper under you and use the baby wipes from the car and clean you off. A passerby saw your big cock being wiped down like a baby and she looked shocked. I fasten the diaper on you and tell you to get your pants on. In the car ride on the way home I ask you “Do little boys jerk off without Mommy’s permission?” A valuable lesson for my little baby boy.

Sissy training phone sex

Come jack off with mommy on Mother’s Day!

jack off with mommyCome jack off with mommy for Mother’s Day honey, lord knows my boys did! They woke me up this morning and dragged me out of bed they were so excited! It was so cute, they made me breakfast and had it all set up out by the pool for me, wasn’t that sweet? After I ate they took turns licking my pussy and let me tell you, that had me squirming and moaning and begging for more! Nothing feels better than my sweet boys mouths on my pussy, they know just how I like it best!

mom fantasiesAfter they thoroughly licked my pussy and made me cum probably at least 10 times they said it was time for me to get fucked, I thought it was just going to be them but they invited several of their friends over to fuck me too! They now that I just adore fucking their little friends and they knew that it would be the best Mother’s Day gift ever if they all came over to fuck me! I had a house full of young men and they all wanted me. They were lined up to get some, isn’t that the cutest?

mommy whoreI had boy cocks in my pussy and my ass and my mouth and more lined up waiting their turn, I never knew that I could cum so often or so hard! I am such a lucky mommy to have boys that know me so well. They always get me the perfect gifts! I’m going to be spending my entire Mother’s Day completely naked and fucking as many boys as I can, honestly, I can’t think of a better way to spend my day. I’ll be over here in paradise, what will you be doing? I bet it’s not as much fun as what I’m doing!

Mom Fantasies For Mother’s Day Jerkoff

Mom Fantasies Eva

Mom Fantasies with the Mommy Whore of the year is what you need, big boy! I’m waiting anxiously to fuck my son and all of his milf loving friends. You won’t need to hold back with me as I am all over the filthy fun of having No Taboos about how I play and get you off.

My son loves to bring his friends around and hopes to get the chance to watch mommy fuck his friends and get filled with man spunk. After all it takes a kinky mommy whore to make these young men real Men!

I certainly hope you agree with the naughty mommy fun there is to be had with me. I am always seeking young hard cocks to pound my pussy and ass all night long and my son loves a well fucked mommy cunt.

Mommy Son Phone Sex – Punishment

Mommy son phone sexMy middle boy had a fit the other day the like of which I have never had with any of my angels. He was screaming at the top of his lungs, crying, throwing things. I soothed him as best I could with words, and gradually worked my way to holding him, soothing him. When he quieted down to just sobs and clung to me, I stroked his head. I pulled my shirt open and he immediately latched on to my tit, sucking for all he was worth, draining my supply. As he nursed, I dropped his pants, and I whispered into his ear that he had been a very bad boy, and I was going to have to punish him for his poor behavior. I smacked each of his little butt cheeks several times, causing more tears to roll from his eyes, and more sobs to wrack his body. Finally, I was finished punishing him, and I felt the need to soothe him. I ran my hands over his cheeks as he finished draining the one tit and switched to the other. I spread his little cheeks and ran my fingers up and down his crack until I started massaging his taint. He started moaning on my tit as my finger started to tease his little ass hole. I stuck my pinky into his ass at the same time that my other hand found his cock, which was already hardening. I started stroking him and fingering his little sphincter. I stroked him and fucked his tight ass until he jizzed all over my tummy, then made him lick it up and share it with me. I hope we don’t have any more such problems.

Jack off with mommy for cheap!

Come jack off with mommy sweetie, you know you want to! Right now you can jack off for cheap too, just be sure to ask me for one of our specials! I have them all listed below, I’m sure there is one that will be perfect for you!

jack off with mommyMy boys are really just too, too sweet! Do you know what they did for me this morning? They made me breakfast in bed and it was absolutely delicious! Fresh coffee, a toasted bagel with cream cheese and a bowl of fresh fruit served by two completely naked little boys. What could be better than that? They were kind of impatient for me to hurry up and eat so I knew that they had something else planned for me… I swear these little cuties are very bad at keeping secrets!

mom fantasiesTurns out they just wanted this mommy pussy, they were bribing me with breakfast to get me in a good mood! Isn’t that so cute? Like they really needed to bribe me in the first place! I love giving them my pussy! I let them take turns sucking my clitty and fingering my juicy hole until I came… then I made them sandwich me between them so I could have one lil cock in my pussy and the other in my ass! I wish I could wake up like this every day!

mom phone sex

The Man of the House

Mom fantasiesYou’re the best son in the world. You’re not a little boy anymore, you’re a man. Now that your father has left you’re the man of the house. It’s your responsibility to take care of the manly duties. Mommy needs you to take care of her sexual needs. Come lick and suck on my sweet pussy. Lay back and let me ride your handsome face. Stick your tongue out as far as you can, tongue fuck me. If you eat my pussy really good I’ll return the favor. Mommy loves sucking cock. Hold the back of my head, baby, feed me your big dick. Fuck my face, put your hard dick in my throat. Mommy loves her baby. Don’t cum yet! I want to ride that hard dick. Let Mommy bounce up and down on your stiff cock. Take really good care of your Mommy. I need your dick every single day.

Your adult baby butt is mine

Jack Off With Mommy

You have been such a naughty little shit today. Talking back, not doing what you are told. I think some discipline is in order for a baby brat like you.

And just your luck we are having company tonight.

I make you put on your most frilly over adult diapers type of panties. I put a nook in your mouth so that I don’t have to hear any more sass from you. I tell you to crawl out to where the guests are seated and have to be the baby you are. The crying starts in front of the guests and I’m not too happy. I guess being displayed in front of the guests isn’t enough incentive to behave. I grab a chair, sit down and tell you to lie across my lap. In front of everyone, I take the back of your diaper off and give your ass a bunch of hard smacks. Your ass is turning red, bright red. I give a few more just to make sure it stings some and put your diaper back on. Have you learned a lesson about being a brat today? A bit of humiliation in front of a bunch of people should keep your sassiness in check…or it will escalate and go even further beyond that.

Mommy son phone sex

They always love to jack off with mommy

jack off with mommyMy boys love to jack off with mommy and now their friends do too! See, I have one perverted landlord, he loves boys, all boys, but my boys especially so he asked for a special video and in return I get free rent for a year! How could I resist an offer like that? I had my sons get a bunch of their friends together for a sleepover so I ended up with about a dozen boys in my house and I told them all that I wanted to play a really fun game. These boys all know that I am a dirty mommy so they were ready for whatever I wanted! Anyway, I had them undress and all start jerking off, the ones that could keep themselves from cumming the longest all got blowjobs from me, isn’t that the best game ever? My landlord was so happy with the tape too, seeing all those boys jerking off and me sucking all that little boy cock was the best thing he’d ever seen!