Category: Sissy boy mommy

Oh Mommy, can I have your nipples again to fall asleep

Mommy son phone sex

My baby boy’s nap time is just about over, so I decide to wake him up my own Mommy way. Lying there peaceful I straddle your diapered cock and start grinding my pussy over it. His eyes are opening and he looks afraid almost like a deer caught in headlights. I keep grinding on his diaper covered cock and tell him Mommy is only here to make you feel good. I lay down next to him and put my nipple to his lips and instinct to feed takes over. While he feeds I open his diaper up and see if he is wet and needs changing. As I pulled the diaper off he wasn’t wet but his cock was certainly at attention. I grabbed his big hard on and started to stroke while he sucked my tits. He sucked for a while until he needed to cum. “So how would you like to cum baby, on my tits, on my ass or just me jerking you off nice and hard and see where it shoots?” “Mommy, can I cum in your ass?” “Well of course sweetie.” I turn around and let him slip my panties off, I spread my ass nice and wide, he fucks my ass, pounding and thrusting until he grabs my hips so tight and has to fuck in short little strokes as he cums. “Oh Mommy, can I have your nipples again to fall asleep?” Anything for my babies.

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.

You Need to be Punished

Sissy Boy Phone Sex

You’ve made Mommy very upset, Son. I had one of my fuck buddies coming over to screw my brains out, but then I get a call from school that my bastard brat got into a fight at school and I had to come pick you up. My fuck buddy backed out because of you, so now you have to be punished. The pregnancy hormones are really sending my libido into overdrive today and I needed that cock I had coming over. So you just had to do for now.

I threw you to the bed after stripping you. You got on all fours as soon as I commanded it because you heard the anger in my voice. Grabbing a belt from my drawer, I bent you over and slapped that little, bare bottom until it was tomato red and you were crying. Then I took one of my dildos and jammed it into your ass. How does that feel, you little cock sucker? You squealed as I fucked your boy hole, begging me to forgive you.

Now that my pussy was wet, it was time for you to make up for what you cost me. I laid back and told you to eat Mommy’s cunt. I was already so horny from the runt kicking inside me that having you lick my honeyhole made me cum pretty fast. But I still wanted you to fuck me, so you kneeled as you stuck that little pecker in my slit. Humping me until you were panting and shaking, you busted a nut inside Mommy. I got the cum I wanted, and you hopefully learned not to ruin Mommy’s plans anymore.

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?

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.

Getting My Little Sister Pregnant too!

Breeding Whore

 

Now that I’m all full of baby batter, my little sister is super jealous and we both want you to help her reach her goal of getting preggie too! You can take us both at the same time, switching between our tight teeny holes and filling us up with your juices. Skip the ass play this time, babe- we need you cumming inside our pussy. Over, over and over again! It’s going to be so beautiful to see us both mature together, right? Watching out tummies start to stick out and titties get puffy. Lick the milk from our nipples and stick a dildo in our cunts so none of the cum comes out. Make sure you get us pregnant! No faking it, no playing around- we both want to see how full you can us. We’re both home alone right now and would love to play. We can take tuns holding each other down for you. I’ll put my knees on her arms and make her suck your juice out of my cunt! Then when it’s finally my turn, she’ll sit her ass right on top of my face and make me lick her asshole till it’s clean as can be. Hurry! Play house with us before mom & dad get home. 😉