Tag Archive: sissy boy mommy

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.

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. 😉

Sharing is Caring

Mom fantasiesMy girls and I just want to have fun. I treat my girls like best friends, we always walk around the house naked. Even when we have company clothes has to stay at the door. No matter who it is, I don’t want clothe at the door. I let them have boyfriends over and stay over night. Always have a bowl full of condoms, boy do we run out quick. I know my boyfriend Phillip get a boner every time my girl stands in front of him. I could see all the precum cumming out. I told him as long as my girl wants you could have her little tight pink pussy, but I have to join. I want to see you fuck my little girl so good. Pop that cherry daddy. I love the facial expressions she makes while daddy Phillip is fucking her. Ummm I start eating her pussy all full of daddy’s cum.. Fuck yes my favorite. I love sharing daddy’s dick with my girls.

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…

 

Good Little Boy

sissy mom

Mommy needs a good little boy to pamper and care for. I will change your diaper if I have to, make sure that little wewe stays clean for mommy.  Mommy doesn’t like dirty boys. Now while your other little friend fucks me, Im going to sit you in front of him so you can rub your little soft dickie on mommy’s clit. Then you will fuck me with your cute little dick, and watch me how good i start sucking your little friends dickie. Yummy mommy likes little soft dicks. Both of you little boys fighting asking me who is better at sucking my clit and nipples. Also asking me witch one of your dicks is bigger and gets harder. Baby no need to fight mommy is all yours, my sweet sweet boy. Of course you are my one and only, but you know mommy likes to have fun with your little friends too. Do you want to have fun with mommy baby?

Mommy Pearl’s Sissy Slumber Party

sissy training phone sexThe younger the better, the sweeter the meat. Training sissy boys is what this mommy loves the best. Sissy boy training phone sex weeds out the girls from the men. I love discovering that you are a sissy. Why wouldn’t you want to be a cum slurping little faggot? Cum tastes soooo good. And that man-pussy is just dying to be violated for the first time.

I’m the kind of mommy that you can feel safe sharing your secret with. I love your pics and watching you transform into a slutty girl. I would never break that confidence or threaten to share your pics, unless you asked me to tease you just a bit. We’ll be like like a couple of young girls sharing make up and sex secrets. There is so much that I want to teach you on how to please a man.

Be sure to bring an ass toy for our first session. You’ll be learning to suck that cock for me. I want to hear you slurp and gag. After it’s all good and wet, drool dripping onto your now worthless penis, I’ll get to the good stuff. You’re gonna bend over for mama, show me that perfect little starfish, that pucker-pussy. And I’m gonna to teach you to fuck yourself like a girl. After all, that thing needs stretched if you’re gonna handle the kind of cock you crave. And we girls all want that perfect kind of cock. The one that stretches us wide open and makes a creampie of of our girly fuckholes.

I’m here all night for your private lesson. It’s like a slumber party, but with COCK!!!

 

 

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

Happy Mother’s Day from your sissy boy mama

mommy phone sex

Happy Mother’s Day.   It’s time for your annual sissy parade. Let mom help you get all slutted up so we can expose your sissy ass to the public. Mother’s Day is the perfect day to do it. All of the moms will be wearing their Sunday finest. It’s time to roll on those silk thigh highs, put on your fancy panties and join the other women as we celebrate. I’ll be honored to fix your make-up, sissy boy.

Raising cock pleasing sissy “daughters” is my favorite job as a mother. If your own mom doesn’t accept you, run to me with open arms. I’ll embrace you and train you to be the best. We’ll tuck that little willie away in a thong and I’ll teach you to flounce that ass. Then I’ll break that boy-pussy in myself with a strap-on before I start you on real meat. Don’t worry. I’ll be easy and sweet unless you are an annoying whiny little bitch who needs some hardcore mommy ass kicking first.

You don’t even have to be a sissy to come play with me. I’m an older woman but don’t think for a moment that I will pass up some rock hard young cock. Mommy fantasies need to be thoroughly explored and role-played. If you ever had a crush on your stepmom or wondered what Mommy’s pussy felt like…….It’s time we had a talk, young man. This fine vintage cunt is aching for some boy batter . Make this a day for Mom to remember forever. I’m here with open arms and open legs. Forget candy. Mama wants cock!!!

Sissy Boy Phone Sex Mommy for you

sissy boy phone sex

Ready for some sissy boy phone sex play time, little boy? Your big, obedient mommy is here to make sure you get the proper training. I’m a no-nonsense mom who expects my boys to be able to serve any cock in town after they are trained. A rigorous schedule of feminization is followed by cocksucking lessons. Are you ready to flounce it for me, little sissy? Purse those pretty pink lips and wiggle that panty ass. That’s a good girl. Now let’s work on that pussy power.
A good sissy needs to be sweet, obedient, submissive, and able to accomodate any size size of cock. Today’s lesson is simple. Mommy is bringing out the big fuck toys and the strap-on. You are getting that first lesson in taking a cock in that new boy-pussy. Don’t worry. Mommy will be kind. It will only hurt a little. I’m not really a mean mommy. I will kiss your booboos and give you a titty. Like a real mom, I just want the best for my sissies. Don’t be afraid. Come to me and I will teach you all that you need to know. Your secrets are safe with me.

Panty Clad Sissy Boi

sissy boy phone sex

Earlier I was doing a little online shopping.  I was thinking of you as I searched for the perfect outfit.  Something pretty and perfect.  A little something to bring out the color of your eyes.  I wanted it to fit your personality.  It had to let others know that you are a cocksucking sissy boi.
You know I love dressing you.  I was thinking of the way your little clitty would fit into a lacey pair of panties.  I sat back and imagined you giving your first blow job in nothing but those cute little under things.  I thought of how your little prick would tremble with anticipation.
Funny how just a bit of shopping brought you to mind.  Now all I can think about is your lace covered dick.  I want to see you lick and suck his cock until he blows his load right down your throat…. Hmmm, looks like I have more shopping to do for my sweet little cocksucker.

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