Tag Archive: sissy mom

Impregnation Phone Sex with Mommy

Impregnation phone sexImpregnation phone sex, Sissy mom, Phone sex milf, Phone sex mommy, Mommy whore, Wet mommy pussyMy darling, my second oldest girl, has decided she wants to get pregnant again. So, her husband and I planned a lovely evening for her. We fed her a fantastic meal, and allowed her to prop her feet up and get comfortable while we did the cleanup. Then, we worked together to make her completely comfortable, stripping her slowly as we massaged and kissed each and every inch of her. When we finally had her naked, we took our time making sure she felt loved, pampering and kissing her face, tits, and finally her pussy and ass. We propped her hips up on a thick pillow, and her husband slowly filled her pussy with his cock. As he was sliding into her, I was gently massaging her tits, kissing her, and watching him stretching her pussy out. I worked my hands down to massage all across her abdomen, pressing gently in. I could feel his cock working its way in and out of her, and I enjoyed the feeling of their joining together beneath my hands. I kept massaging her abdomen with one hand, but moved the other to start gently massaging at her clit. He did a great job of following instruction, keeping his dick moving at a nice, slow, steady pace. I could tell it was very hard for him, that he wanted to have his way and fuck the ever-loving shit out of her, but he showed his self-control that day. Between his moving in and out of her, and my massaging her, she got off several times. Then, and only then, did I allow him to plow her hard. And he did! He had her tits bouncing up and down, her abdomen flexing repeatedly with the brutality of his thrusts. When he finally came, deep inside of her, he shuddered with it. I made her stay like that for a while, hips in the air, letting that baby-making juice work its way deep inside of her. We hope that she finds out soon that she’s expecting!

Put these lace panties on and confess.

sissy boy momI’m a real life mommy but being a Sissy boy mommy is my favorite role. Guiding little faggot boys into being girls makes my pussy wet. You just need a little guidance, young sissy, and soon you will be what you’ve always known you are.

I pulled the strap on over my panties, marveling at my huge cock. You were bent over in front of me, trembling in fear and arousal. “I’ll be easy.” I whispered, as I pushed my fat cock head against your pucker-pussy. You gasped just a little as I gave it a nudge, opening you. I squeezed your round ass cheeks as I shoved a little deeper.  “Squeal for me, sissy. Tell me what you need.”  You gave a little faggot moan and arched that pussy higher. “I need fucked, mama.”  “What do you want?” I demanded. “Cum. I want cum. “Louder.” You squeaked louder. “Please. I need it so bad.”

I pumped that little bitch until your boy pussy was raw and you loved it. Now pull those panties up and feel the cum seep from your wounded hole. It’s time for round two.

Sissy Boy Therapy

Milf fantasy storiesYou’re up late tonight. You’ve already jacked off three times but you need some Milf fantasy stories to really empty those balls. It’s time you talk to a real life mommy who gets what you really need. No amount of phone sex moaning is going to satisfy you when what you really want to be is a sexy slut.

Think of me as your phone sex therapy mommy. Having a sissy boy of my own, I totally get your needs. The way you want to dress up. I can even send you the perfect pair of panties. Nice and fragrant, to make you think of mommy. You want to please mommy, right? So put on those panties, grab that trainer ass toy, and let’s start this session.

Tell me about that cock you crave. Is is big? Do you want to be submissive and forced to gag on it or just allowed to nibble and tease? Does mommy need to stretch that pussy first with a dildo or strap on? Or are you an eager slut who wants that boy pussy pounded hard? One call with Mommy and we can explore your special needs. Your clitty will explode in those panties. Quit denying the faggot truth and come talk to me soon.

You say Sissy like it’s something bad.

sissy momI’m not your regular old run-of-the-mill mommy. My specialty is tranny girls, sissy boys, and playing dress up. Plus good old fashioned spankings for naughty boys. When you need a real mommy with experience, you need to come get some tutoring from me. I will make you into a real life sexy slut. I love getting your pics and showing you exactly what you can become. Bring a toy for our calls and we’ll stretch that new boy pussy to handle the biggest cock. Mmmmmm, I know you love cum.

So, go raid your wife’s or daughters panty drawer. Or order some from me to play in. This mommy is going to teach you the ropes. Don’t be shy, little sissy. I can tell from the way you walk that you’d make a natural slut. With that round little ass and cock sucking lips, you’ll get more cum than you can handle. All you need is a little training and you’ll be on your way. I’m your new non-judgmental mommy and I will bring out the best in you. Don’t be shy. Share your fantasies and come get off with me. I know that little clitty needs some attention.

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.

Older posts «