Category Archive: Sissy mom

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.

Sissy Mom Nicolette: I Love Sissy Boys

sissy momI love being a sissy mom. I have a lot of offspring from my two marriages. No two sons of mine are the same either. I have one from my first marriage who was always a mommy’s boy. He is in his 20s now and not much has changed except now he cross dresses. When he was little, he would play dress up in mommy’s sexy pretty things. I encouraged him. In fact, I would do his makeup and hair to accentuate his outfit. At the time he was my only boy. I didn’t really know how to interact with him. I wanted a daughter. He was suppose to be a girl. We were told we were having a daughter so his room was all decorated in pink and Disney princesses. That may have altered his path somewhat! Even after we changed his room to reflect a boy’s room, he showed interest in all things girlie. I knew I had a sissy for a son. I am a loving nurturing mommy, so I let him wear my panties. By the time he was playing dress up, I had birthed some more sons and they were everything he wasn’t: masculine. No shame in being a sissy faggot. When he got older, I had him dress like a girl and give head to his brothers and his sister’s boyfriends. Turned out he liked sucking cock. He was a natural. Still is a cock sucking slut. He goes to glory holes and bars to suck cock. Even the straightest of man will let him suck his dick because he dresses feminine. I have feminized him; helped him become a cross dressing sissy that gets all the cock he wants. As a phone sex mommy who loves sissy boys, I can help you too. I have years of experience as a sissy mother to my son. I love him, just like I will love you. 

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Phone Sex Mommy’s Valentine’s Treat

I will make my darlings the most amazing breakfast today. Heart-shaped pancakes, arrow-shaped sausage patties, bacon, oatmeal with strawberries and raspberries and cream. And, the coup de grace, Mommy will serve it completely naked, and let them take their fill of whatever they wish from me. Quite frankly, I wouldn’t be offended if they ignored breakfast altogether and teamed up fuck me. I’ve been so excited all morning, Phone sex mommyI haven’t been able to sleep for thoughts of what I want them to do to me racing through my brain. I keep imagining them thanking me for my hard work, and then pushing their plates forward as I fix each one. Then turning me around to bend me over and eat my cunt and ass, one of my boys walking up to face-fuck me at the same time. I imagine their fingers poking up inside of my cunt, a couple of them climbing underneath me to nurse at my tits. I can just see them taking the syrup and pouring it all over my ass and down my cunt, squirting some up inside of me, then licking it out and off of me. All of my darlings would just scramble for that sticky-sweet nectar off my milf ass. Oh, I hope they enjoy their breakfast!

Mommy and daughter fun cum time

Jack Off With Mommy RoxanneMommy loves it when she gets to eat her younglings pussy hole. I have found that I have a taste for that innocently sweet juice and the cream it gives after licking it for a while. Its like eating strawberries and cream. I like it even better because it came from me and it adds a naughty factor t amp up the intoxicating affects of arousal. The lil pussy lip so sweet and petite make my pussy wet with desire and delight. I want to pop that cherry and deflower that little hole with my tongue and my fingers until a little bit of dew drains out, then I want to lick it up and show that mouth where to make mommy feel just as good. I will direct exactly where to lick mommies cunt so that the favor can be returned. That whole hand can fit in my pussy and that wee tongue can lick mommies clit until mommy cums too.

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