Category Archive: Sissy mom

Phone Sex Whore & Daughter

Phone sex whoreShe came into the study as I was cleaning up after a hot session with my husband. My wet mommy pussy was still dripping cum, as I hadn’t gotten to that part of the cleanup yet. She walked up behind me, wrapped me in her arms, and pulled both of us onto the desk for a sexy cuddle. Since my husband had just finished plowing me over the top of this same desk, I got even more hot and bothered. She told me she wanted to thank me for helping try to get her pregnant, and pulled me back so that I was over top of her. She settled my dripping, cum-filled cunt down over her face and started tearing it up! Her tongue danced over my clit, across my gash, and then dove deep into my pussy. She cleaned every drop of her father’s cum from my pussy, and still worked me over. She didn’t stop until she had me screaming her name and squirming all over her face from the orgasms I was having. Then, she pulled me back down to her level, kissed me, and said that I was the best mommy ever. Oh, the joys my heart can bear!

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!

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.

A loving Mommy’s touch

MILF fantasy storiesThe MILF fantasy stories began so long ago when you were just a boy. I was such a horny mom and Daddy never was around. I began to rely on my young son for my sexual needs. It started so innocently. A lingering cuddle. Sleeping with mommy during storms. A dropped pair of dirty panties. You became my little man. As you got older and your cock started maturing, I begin to notice that too. The muffled moans at night. The long showers. Oh yes, a mommy knows that her son is jerking off.

Curiousity began to get the best of me. Thoughts of “How big is his cock?” and “I wonder how many times he can come in a row?” This led to some long sessions with my vibrator, plunging it into my cunt, whispering your name as I came.

Meanwhile, you and your friends were watching me with teenage eyes. My round ass, huge tits, and revealing clothes were giving out some hot signals. I had no idea that they were having jerk off sessions together, discussing if I would fuck them.

One night I came home tipsy to catch you boys watching porn. I was hornier than fuck and those teen cocks waving in the air finally got to me. I joined you all for a cocksucking circle jerk and mama got all of the cum. With a little persuasion, I stripped off my clothes and you all jumped on me like a horny wolf pack. I got all of my holes pounded that night….and every night since then. I’m sure the other parents wonder why their boys always want to spend the night here.

You wanna be one of my boys too and relive some hot mama fantasies?

Johnny and his giantess girlfriend

Jack off with Mommy

One of my favorite Jack Off With Mommy clients is a little Asian man named Johnny. Johnny loves his giantess girlfriend and I adore my little sissy. It’s like having my own little doll. I dress him up and take him out on the town as my personal pet. It’s so much fun to introduce him as my tiny boyfriend and make him sit on my lap or in a high chair. People think he must be packing a huge cock or a fat wallet, when in fact, he has neither. I just like the superior feeling it gives me making him into a little submissive slut.

Sometimes, we go out with my besties, Selina and Addison. We all pick up some big black studs. We know poor little Johnny is so jealous of their huge cocks since he is so tiny. Teasing him  makes us laugh so hard. We all get fucked up together and go to the Land of Giants.  There Johnny is a perfect sized human dildo for us. We cram him into each others pussies, drowning him in juices. He begs to be smaller. I tie a string around his feet and cram him inside of me, like a tampon. To humiliate him I ask my black stud to fuck me, pushing Johnny Tampon deep up against my cervix. We laugh and tell him that’s what a real cock looks like in a pussy. Johnny gets so excited that his tiny cock spurts all over my insides.

Maybe you have an equally wild fantasy. Don’t be shy. We love to roleplay the unique and unusual. Nothing is too crazy for us. Tell us your thoughts and we’ll make it feel like the real deal.

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…

 

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