Tag Archive: sissy mom

Sexy Phone Chat with Mommy

My husband and I love to do some kinky stuff. He walked into the house after work yesterday, and found me sitting on the coffee table, almost naked, slowly stroking my cunt. Well, he broke out his phone and started recording it. Sexy phone chatHe caught me rubbing my clit and stroking my breast, playing with my nipple. He even crawled onto the floor under the coffee table, and caught the best view of my puckered little asshole and pussy just as I slid my fingers into myself. I started fucking my fingers for him and his camera, and I watched as his cock got harder and harder, and his free hand took it out to stroke it. I got myself off, and even dribbled on the table some, before I stood up and straddled him as he lay there. He kept recording as I slowly lowered myself onto his hard dick. He caught every moment of me sliding straight down his shaft, until I could start grinding on him. After a few more minutes of him recording, I finally took his phone and turned it off. I set it aside and put his hands on my body. He massaged my tits and played with my clit a bit, then finally grabbed my hips and started to really fuck me. This was what I wanted, to feel his powerful thrusts driving my pussy straight to orgasm, and I spasmed all around him, milking his cock of every drop of cum, too. I love teasing my husband!

Late night Tranny fantasies

Sissy training phone sex

Just admit it. Sissy training phone sex is what you are on here looking for. You’re not just another hard dick looking to get jerked off.  You have some special needs and you want the perfect mommy to help you. Sweet boy, quit hiding from your desires and come tell Mommy. You see, I’ve known your kind before. My older brother and my own son are both sissies. I trained both of them to be cock sucking little sluts. I can train you too.

I mean, you’ve known from a young age what you really are. You are a closet faggot who hides the fact that you want to be a girl. You want to be dressed up. You want to be properly and gently trained. I want to hear those fantasies. I’m an older sissy mommy with experience so no shame, no judgment.

Your need to wear panties and lingerie doesn’t shock me. In fact, i will sell you some that are perfect for you. You also need an ass toy to start your training. Oh, it will feel so good and so right inside of you. My strap-on is also available to help you stretch that new pussy.

Quit trying to sleep when all you think about is cock. Bring it to Mommy and I will explore all of your faggot or tranny fantasies. You will be so pretty and fuckable.

Mom Chat – Tiny-Dick Bitch

Mom chatI don’t think I’d ever seen such a tiny dick in my life! The damn thing couldn’t have been more than about 2.5 inches. I couldn’t help but laugh at him, standing there, expecting me to do something with that thing. I had to call my husband and my 2 oldest boys in, and stand them naked next to him. The size of his cock was absolutely no comparison to my mens’ cocks. I told him how hilarious it was that he thought I would fuck that, that he thought I would be ABLE to fuck something that tiny. We all told him what a worthless little bitch he was, and how he was more of a girl than I was. Mommy whoreI showed him that my own clit was about as big as his dick. He was red as could be, but I couldn’t help myself. I told my boys to bend him over and turn him into the woman he was meant to be. The younger of our sons went first, jamming his dick into the little bitch-boy’s sphincter. He cried out and tried to pull away, but I walked in front of him and helped to hold him in place. I smacked him across the face one good time to distract from the pain and remind him that he was a little bitch-boy, and would be treated as such. He finally adjusted to the dick going in and out of his ass, and I reached down to grab that tiny little cock. His sack was so full, it was bigger than his dick, even. I let each of them fuck him, and they each came deep inside his shitbox, but I wasn’t quite done yet. I went and grabbed my strap-on, and I plunged that big dick into his ass. I fucked him for all I was worth, proving that I was more a man than he was. He went home with a lot to think about today.

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?

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

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!!!

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 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

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!

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