Category Archive: Sissy mom

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…

 

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?

Jack Off With Mommy Dirty Boy

Jack Off With MommyHis diaper stunk so badly, it was all I could do to keep from gagging. I undid his diaper, having him lift his legs so that I could clean under his tooshie. I wanted so badly to plug my nose while I did this, but the mess was so big that I had to have both hands to clean without spreading the mess everywhere. It didn’t help that the more I wiped, the more he wiggled and squirmed, and the harder his dick got. I was so distracted by the mess at hand that it didn’t hit me, the reason his cock was getting so hard, until the last second. I didn’t make it, though, despite figuring it out. He let loose a stream of hot piss all over my face and chest. I wiped my face and chest as best I could with the wipes, then finished cleaning his tooshie. That was when I realized his dick was still hard. I asked him what was wrong, and if he needed to tee tee again, and he shook his head no. I asked him if he thought that mommy was going to play with his willy, and he shook his head yes, adding a “pwease”. I had to tell him that little boys who still make messes in their diapers don’t get rewards, and I pulled the clean nappie up over his hard dick and sent him on his way. I had to take a bath after that, and you know what I did while I was in there? I rewarded myself for a job well-done, with a fingering until I came hard.

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!!!

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