Category: 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.

Anal Phone Sex Mommy

phone sex mommyThis phone sex mommy loves anal sex. I start my boys off with my ass. When they are young, their cocks aren’t that big yet. I have birthed six fuck buddies so my pussy is no longer tight. A little dick flops out of a well fucked pussy. My ass, is another story, however. My ass would feel tight on your pinky finger. My daughters watched their older brother fuck my ass last night. They were in amazement that anything went in that hole. So, after I had an ass full of boy cum, I turned my attention to my sweet slutkins. I am of the school of thought that when they start showing interest in anything sexual, that is when you teach them. I like to nurture natural sexual curiosity. I enlisted my son’s help. I put a girl over my lap and one over his lap. We dipped our fingers into Vaseline then fingered their little butt holes. I told my son how to maneuver his finger so to give his sister a great anal experience. Both girls squealed in delight, which is music to my ears. I love hearing them have sexual pleasure. My son started double fingering his sister, so I did the same to my other girl. Damn, both girls creamed all over us. Daddy is going to be so excited to hear that his daughters are ready to have their ass cherries popped. Their brother was jealous. He wanted to tap their asses first. To distract him from their cherry butt holes, I offered up my wet mommy pussy. I let him fuck the hole he came out of so he would fill me up with his cum. His sisters got another family treat. They got to lick their brother’s cum out of mommy’s shitter. I love family time.

Mommy son phone sex

mommy son phone sex

My son went to a party and he came home so wasted. He stumbled through the door and professed his love and claimed that he needed his mommy’s pussy so badly. He got on his knees and started to tongue my pussy licking every inch of my pussy making it sloppy wet.

I got so turned on I pushed him back onto the floor and pulled his cock out. I started sucking and swallowing his cock down my throat. I was making sure it was lubed up with my spit. He was leaking pre cum so I decided to trace it on my lips as if it was lip gloss.

His pre cum tasted so good that I could not resist wanting to suck him dry. He grabbed my hips and begged me to fuck my pussy hole. He entered his cock inside of me with one big thrust. I was taking that cock stretching me open and going balls deep inside of me.

I keep squirting all over his cock and begging for him to nut inside my pussy. I love walking around and feeling his cum inside of my for days!

Impregnation Gangbang

impregnation phone sex

 

I invited a bunch of my neighbors over for a little fun- giving them each the instruction not to masturbate for a few days. One-by-one they arrived at my house to be greeted by me in a tiny little baby-doll dress with no panties or bra. I was especially glad that you showed up. My pussy dripping with excitement, I had all of the guys sit down in my living room. “Okay boys, you’re all here today on a mission for this block-party orgy. No blowing that load anywhere but my cunt!”
All 8 of them had hard raging cocks, ready to fill my tiny clam up with their baby making juice. Stuffing up all holes with their dicks, taking two inside my cunt at the same time- I want to make a baby with all of them. They pounded me hard and it hurt so much but I love when there’s pain involved. One of them flipped me over, so I could suck his cock upside down and take it deep in my throat. I threw up a little and made a mess but that guy didn’t seem to mind. But now it’s your turn and you shoved tease my cunny with the head, but I push myself down hard on your meat-stick and you explode instantly.
Slowly the party dies down, most everyone has left except you. I whisper, “Lets make sure you get me preggie!” and your cock swells up with those words because you want to see how big my belly can get. You pull me on to your lap so I can ride, inserting that beautiful baby-maker all the way. You shoot one last load into me. I relax, keeping you inside me so that I don’t lose any of that sperm and we both fall asleep in that same position. Hours later you wake me up and tell me you gotta leave but that you’ll call before you come back over.
I’ve been sitting by my telephone for hours because I know you’ll ring me up eventually and I don’t want to miss you. When are you cumming back over, baby? 😉

Wet mommy pussy

wet mommy pussy

My son and I went on a date since we hadn’t been spending much time with one another. He was so quiet and just didn’t seem to want to hang out with his mommy. As I was driving us to the movie theater I noticed that he kept glancing at me up and down.

I was wearing a button up shirt that exposed my large perky breasts and a nice short skirt that left little to the imagination. No panties and some very sexy high heels. Let’s just say I dressed to impress. My son was to busy on his phone texting or playing some dumb fucking game that he just kept to himself.

I got so annoyed that I grabbed his phone and chucked it out the window. This just made him more upset. I pulled over on the side of the road and told him to calm the fuck down and promised that I would make it up to him. We got to the movie theater and surprisingly it was empty.

Well it was 11am on a Tuesday so go figure. The lights dimmed and that’s when I went to town on my son. I grabbed his hand and placed it, on my bald wet cunt. I helped slide his fingers inside me as I began stroking his cock. I took of my shirt and bra so I could show off my nice mommy titties and pretty much gave my son the stare. He Could not resist me at all.

He unzipped his pants pulled out his cock and began fucking my nice milk jugs. I allowed him to penetrate my tits with his cock as long as he allowed me to lick and suck the top of his cock head. I leaned over a seat exposing my nice wet holes and begged my son to fuck them and fill them up with his delicious cum.

I didn’t care if people walked in and saw I really needed to my sons cock inside of me. I made him fuck me through the whole movie until my pussy was sore and filled. I guess I need more dates with my son since this one was obviously a success.

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.

 

Dirty Mother-In-Law

Mother in law phone sexI knew I wanted to fuck you the first time my daughter brought you home. I welcomed you into my home with a tight hug, making sure you felt my huge tits against your chest. We had a normal “get-to-know-you” conversation, the whole time in my head I’m picturing me on my knees with your cock in my mouth. My daughter is too young, she doesn’t know how to please a man like I can. I was wearing a short sundress with no panties, and when my daughter went to the kitchen for drinks I spread my legs and flashed my pink pussy. Your face turned beet red and I giggled. My goal is to get you alone and fuck your brains out. This cougar wants your dick in her asshole. Let me really welcome you into our family. You’ve had my daughter now it’s time to have the mother.

Mommy Son Phone Sex with Pearl

mommy son phone sexWhat can I say? Mommy son phone sex just feels damn good. I love young cock. And these boys need a mom like me to train them. Don’t you remember the first time that your mommy put your cock on your cock. Maybe she was washing your balls or helping you put on your underoos. her soft fingers touched you and suddenly, that was all you could think about. You were so turned on.
You lie awake that night with your hand on that cock, jerking it raw. Mommy’s soft tits pressed against you when she said goodnight and you almost creamed your sheets. You moaned out loud. You didn’t see me in the doorway in my short gown. I was smiling and you knew you were busted. “It’s alright, sweetie.” you whispered as you slipped into bed beside me. I felt your hand touch my cock as you drew my head to your breast. Tonight would be the first of many…..

Phone Sex Mommy Voyeur

Phone sex mommyTwo of my younger darlings had disappeared, and I was trying to find them when I heard some very sexy-sounding noises coming from my bedroom. I figured my husband was watching a sexy movie, and I almost walked past the door, but decided to peek in anyway. I found the two I was looking for, both naked on my bed. They were watching the tv intently, looking at each others’ bodies, trying to imitate what they were seeing on the screen. He told his sister that she was too small up there, trying to grope at her non-existent tits. I leaned against the door frame, just watching, seeing how far they would get. She knelt on the bed, next, and he stood up, balancing himself for a second. She grabbed his dick, looking at it like it might bite her, then glancing back at the tv. I guess she was satisfied that this was what she was supposed to be doing, because she opened her mouth and ran it all the way down the length of his little cock. The first couple of strokes, he complained about her teeth, but then she figured out how to suck instead of trying to gobble it, and I watched my son get so hard. His little pecker was still small, but it was beautiful, too. It wasn’t much longer before she lay back on the bed, and he crawled down between her legs. He looked at the tv, and then back down at her little cunt. He spread her lips apart, I guess to make sure it really looked like it did on tv, and then shrugged and touched his tongue to her clit. Then, he started to imitate the man on the tv, running his tongue up and down her gash, over her clit and ass, sliding a finger or 2 into her cunt. By this point, I was finger-fucking my own pussy right there in my hallway. By the time he pulled himself up over her and started trying to work his cock into her cunt, she was moaning and groaning, pleading for orgasm, not that she realized it yet. When he thrust up into her, they both went wide-eyed, and then it was on. He was pumping hard and fast, uneven strokes, just trying to make the feeling that he could tell was coming come faster, and she was holding on for dear life, bucking her hips up and down. They came together and I exploded all over my hand and down my thigh.

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