Tag Archive: sissy boy mommy

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.

Sissy boy mommy sex with Daphne

Sissy boy mommy

I caught my little man going through my panty drawer! He was sniffing my panties. I stood there watching him. He turned to see if he was alone. I hid behind the door trying not to breath hard. I waited until I thought he was turned around. I looked back to see him naked, pulling up my sexy lacy panties over his hard cock. It was hot watching him put on my panties. It was even hotter watching him pull out my thigh high pantyhose. He started rubbing them over his face, sniffing them and rubbing his cock. He put them on one by one. It made my pussy dripping wet. Watching him rubbing his cock in panties. I watched and waited. I watched him cum in my panties and put them back in the drawer. I slipped back outside and waited a few minutes. I walked in as if nothing happened to find him asleep on the couch. I knew he was faking. I went right into my bedroom and ate all of his cum out of my panties! 

Sissy boy mommy

sissy boy mommy

I love boys that cater to every demanding call that I have. I am a nurturing mommy especially to my boys that are feeling a little whimpy from time to time.

For instance, my sweet boy today decided to be such a wittle wussy today! I stuck a big pink pacifier in his mouth and made my sweet little diaper boy wear his princes pampers.

He is such a little princes at times. I get such enjoyment out of him not being a real man and needing to sit in his soiled diaper all day long and wait for mommy to give him attention.

My little pamper princes is such a sissy it is laughable. “She” constantly needs supervision and someone dictating her every move, so when I can not attend to her needs, I get my sitter to help out from time to time.

I love dressing my sweet little pamper wearing sissy up and making her into the perfect little diaper wearing bitch. She belongs in diapies and that is wear she shall stay!

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. 

phone sex mommy

This Sissy Mom Loves Our Site Sissy and All Sissies

sissy momAs a sissy mom, I attract all sorts of losers, but I have yet to attract a sissy as pathetic as our company Sissy. Our company mascot is a Sissy, owned by our boss, Mistress Levi. On occasion, we are invited to help shame the most pathetic pansy of them all, Sissy Michael. This sissy is such a fruity fag too. She has clothes especially made for to wear in public because she loves being shamed by total strangers, especially young girls. I was showing my daughters pictures of the site Sissy in her various outfits and they could not contain their laughter. Seeing Sissy in a cheerleading outfit was enough to make them share the pictures on their social media accounts. My eldest teen daughter captioned a picture “Sissy maid training in session.”  She was begging for me to get the company sissy to come over and be her personal servant.

sissy maid trainingI had to break her heart that it doesn’t quite work that way, but I promised I would find her a local sissy for her very own. But, I did have to explain to her that there will never be a sissy quite like our company sissy. Our site sissy has a teenie weenie that is often under lock and key by Mistress Levi. Sissies should only touch themselves when granted permission, but some sissies like this Sissy are just too shameful to be allowed to play with their minuscule little dicks. Our sissy even has her own site. I showed my daughters her site as well as blogs other women hear have done over the years about her. This pathetic cross dressing pansy has dressed in baby garb, frilly dresses, cheerleading outfits, formal gowns and even a play boy bunny outfit. She is a total disgrace to the gender she was born.

sissy boy mommyOur site sissy poops her panties; prances about in public begging to be shamed and loves to be humiliated by sexy women and total strangers. This sissy boy mommy is grateful that she does because she gives me a lot of entertainment.

Wittle sissy baby needs to be humiliated!

sissy boy mommyThe boss lady here has her very own sissy mascot and from time to time we all humiliate her. I haven’t done so before now because I try not to ever be too mean, but once I saw her baby pictures I just couldn’t help myself! Hahaha this little sissy baby is really a ridiculous sight! She sucks her thumb and wears little frilly pink baby clothes… she even wears a diaper so that she can fill it with her poop and sit in her shame all day! Is it really any wonder that we all laugh at her?

sissy momI mean just look at her! She is a hoopy earring wearing, panty pooping little sissy bitch! What could be more laughable than that? The funniest part of all this though is the fact that this sissy fairy faggot right here pretends to be a man at work every single day! Can you believe that anyone would believe that a little prissy sissy baby like this could possibly be a man? She’s even married! Hahaha The thought of a baby like this being someones husband really cracks me up! This is a sissy that needs to be dressed up and paraded about town in her poopy shame! She needs to be forced to wear a diaper in public so that everyone can see and smell her shame!

sissy training phone sex

Little cock and big cock

Family fucking Roxanne I took my little bambinos out to eat last night for dinner because I had made a little extra money from shaking my ass on that pole and my baes were starving since the weak before was skimpy, but I guess I still did not have enough to cover all of dinner. I did not know what I was going to do. Thank god that the manager enjoyed trip over to the Philippines for paticular reasons if you catch my drift. He had a taste for much smaller cock. I had my son with me and he had to do some “extra” work to help me cover the bill for dinner. I thought it was going to bother me seeing such a small dick and a larger dick playing together but it actually turned me on quite a bit. MY son took it like a champ and only cried only a little bit. I may see if we can get free food elsewhere too and have my boys pay more often.

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