Category Archive: Sissy boy mommy

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.

Jack off with Mommy at the Yard sale

Jack off with mommy

It was a jack off with mommy annual event in our neighborhood. My annual garage sale. I’m not a hoarder so every Spring I clean out my closet and lingerie drawer and sell it all. It’s so much fun to watch my neighbors show up, trying to be all discreet. They creep over a few at a time. And no one ever tries to haggle. They know I have the good stuff. I even have a few used toys if you’ll just ask.

You were my first customer. I was watching you out of the corner of my eye as you held a pair of panties up to yourself. I stifle a giggle as you try to tell me that they were for your wife. Your wife is a 250 lb oinker so I know that these are for you. I always suspected that you were a panty boy and now I know the truth. “I think they will look great on you.” I whisper, watching you turn red. “Shhhh, it’s our secret. Just let me know when you are ready to model them for me. I love a man who wears panties. Would you like the matching bra, too?” You look like a fish outta water as you gasp for air. I know I’ll be seeing you soon.

By the end of the sale, I have a fistful of cash and a list of names signed up for sissy lessons. Wouldn’t you like some of my sexy things, too? You can model it for me and send me pics. Mommy loves little faggot boys who beat their meat into their panties. Your secret is safe so come share with me.

 

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.

Mommy phone sex looking for her adult baby

Mommy phone sex

I must be having a huge surge of hormones, I am horny all the time, and I do mean all the time. I wake up with a throbbing pussy and I got to bed with a throbbing pussy, no matter how many times I get fucked or masturbate. Nothing seems to do the trick. So I decided to try something different. I’ve always loved the idea of a full-time adult baby. I went on tinder and craigslist to advertise for one. I received many emails and chose a few of them to check out and talk with. There are two people who seemed to have the time and desire and we set up some times to explore and see how the chemistry worked out.
Both ended up being very compatible and a lot of fun to play with. My favorite part is nursing my youngins. One of them in particular likes suckle for a long time, making my nipples huge. She can’t seem to get enough; she said they get so big she can feel my nipple at the back of her throat. The other likes changing time and Mommy quietly jerking him off while he naps.
I think I will keep exploring with my two new youngins and see what kind of sexual mischief we can get into. I would love to hear about stories you have or fantasies you have. Explore my Mommy side with me?

Lactating phone sex

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

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