Category: Sissy mom

Training my new sissy

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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

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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?

Jack Off With Mommy Dirty Boy

Jack Off With MommyHis diaper stunk so badly, it was all I could do to keep from gagging. I undid his diaper, having him lift his legs so that I could clean under his tooshie. I wanted so badly to plug my nose while I did this, but the mess was so big that I had to have both hands to clean without spreading the mess everywhere. It didn’t help that the more I wiped, the more he wiggled and squirmed, and the harder his dick got. I was so distracted by the mess at hand that it didn’t hit me, the reason his cock was getting so hard, until the last second. I didn’t make it, though, despite figuring it out. He let loose a stream of hot piss all over my face and chest. I wiped my face and chest as best I could with the wipes, then finished cleaning his tooshie. That was when I realized his dick was still hard. I asked him what was wrong, and if he needed to tee tee again, and he shook his head no. I asked him if he thought that mommy was going to play with his willy, and he shook his head yes, adding a “pwease”. I had to tell him that little boys who still make messes in their diapers don’t get rewards, and I pulled the clean nappie up over his hard dick and sent him on his way. I had to take a bath after that, and you know what I did while I was in there? I rewarded myself for a job well-done, with a fingering until I came hard.

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.

Happy Mother’s Day from your sissy boy mama

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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

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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.

Phone Sex Mommy Observer

Phone sex mommyHe loved watching. He spent the entire day following us around, and watching all that we did together. He watched as my husband ate my cunt while our middle boy ate his ass. He watched as my daughters took turn sucking their daddy’s dick and eating me out. He watched as I ate each of my girls, and sucked off each boy. Later in the afternoon, we all attended a poly-party, and still all he did was watch. He never joined in, never even touched his own cock. He just sat there watching, as I was fucked by every man in the room, filled with cum, and then cleaned up and out by my darlings. Then, and only then, did he take a turn. He walked over to my cum and saliva-drenched cunt, propped my legs over his shoulders, and pulled out the monster schlong he’d been hiding all day. He rubbed it over my clit, and then slid it right into my already-stretched out pussy. It slid all the way to my cervix, and then started pushing my cervix deeper into me with every thrust, until he was finally balls-deep in me. He started fucking me hard and fast, keeping my legs on his shoulders, his fingers playing over my clit, and he drove me to a fantastic orgasm! When he shot off inside of me, I thought we were done, but I was wrong. He pulled out, dropped down, and started eating his cum right back out of my cunt. It was so erotic!

Panty Clad Sissy Boi

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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.

Do you love pregnant pussy?

Teen phone sexDo you like breeding whores? I have always had fantasies about having a big belly and big milky tits. When I was a lil one me and my daddy used to play and every time he shot that white spunk deep inside my pussy, I would imagine my big belly. Guys love my tight little pregnant cunt, and love filling me up over and over again. I am always looking for guys to give me there cum. After I have my lil one we can have our fun with him/her too, show her how good it feels to be filled up by her/him mommy and daddy. Make our little tight pussy youngin nice and pregnant. Pregnant pink pussy is the best pussy, don’t you think?

Mommy Son Phone Sex – Trouble

He wanted his mommy so badly that he had the school calling me to come and get him before they had to do something drastic. I got him loaded into the car, and off we headed toward home. I tried to get him to tell me what was going on, but he just sat there quietly. Mommy son phone sexWhen we got home, he was at my side the moment we got out of the car. He stayed stuck to my side the entire way into the house, and only then did he let me go. He picked my skirt up, dropped my panties, and buried his face in my cunt. I fell back against the front door with the force of all his efforts, and just started to enjoy the cunt-licking that he was giving me. After a few minutes of that, he asked me to turn around and get down on my hands and knees. He drilled his dick into my cunt and started pounding my pussy hard. As he thrust in and out of me, he started to tell me about this girl at school that he had a crush on. Apparently, she’d rejected him in the harshest of ways, and everyone within hearing had started to laugh at him. The more he talked, the harder he pounded into me, digging his little fingers into my hips as he drilled my cunt. As he talked about how he’d imagined taking her and forcing her to fuck him right there, his fingers and cock were digging into me so hard that my orgasm hit and didn’t stop. My muscles flexing around him, along with the thoughts of it being her cunt he was drilling, drove him over the edge, and he let a massive fucking load go straight up my cunt. My poor darling really had a rough one.