Category: Jack Off With Mommy

Sissy Training Milf

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When you are training to be my sissy there is one main rule you must remember. I am your Alpha. Yes, I am a female, so? You call yourself a man to your colleagues but when you step into my room you’re my slave. When I get my hot black slit fucked my sissy boy better be there ready to beg to suck the cum out of my twat and clean it all up. Before you can you must also thank the man who filled me up for allowing you to taste his yummy load. You’re lucky I let you get this close to my beautiful pussy because your little dick can’t even begin to satisfy me. Even during the nastiest times you will be around to be my sissy will be in training! I refuse to rough up my delicate ass after taking a shit when I can just have my bitch clean my shit and piss with his face. Being a sissy in training has its perks though! You get to spend all the time I want you to with me!

Mommy breaks in a Sissy.

jack off with mommy

My poor little sissy. He still hasn’t learned how to properly suck cock. I think it’s time to go out and get some practice. He says no because he doesn’t want to be recognized in public wearing his mini skirt and thigh high stockings. But he’s such a pretty girl and that sweet mouth is begging to be used along with a tight little man-pussy. Oh, yes. it’s time. I saw him last night on his knees trying to suck a big black cock. He gagged and sputtered. My nigga loved dominating him and just face fucked him harder. He nutted so hard that cum came out of sissy’s nose.

So put on your pretties, your lacy thong. Get those balls shaved smooth. Cause your training starts tonight as I guide you on being the perfect little cum guzzling tranny slut. Our first stop is a local glory hole where you can learn to suck a cock correctly. Maybe after a few dozen loads pumped down your throat, you will be able to give head with some finesse. If not, I am gonna just back you up against that padded hole and let the savages rip that asshole wide open. Oh, they are gonna love that tight little boy-cunt so much!!! And I will be laughing at you while they do it!!!

Wet mommy pussy

wet mommy pussy

My guy friend invited me and my Mongols on a boat ride the other day and it was a squirting wet good time! Me and my daughters were dressed in little bikinis that our tits popped out of and my sons had rock hard cocks sticking through their bathing suit bottoms. It was hard for us all to wait until the boat took of for us to get a little crazy. My guy friend drove us far away from shore. We blasted music and opened some liquor. It was the first time that I consented for my sweeties to participate in drinking with their mama. I am glad I did. We all were sharing drinks and dancing around on one another. As the day got hotter so did things on the boat. Bathing suit tops were coming off and me and my girls had rock hard nipple that we had the boys licking and sucking. We took turns pouring vodka down one another and had the boys suck it and lick it off of us. We were doing cleavage shots. My pussy is so wet and I know my girls are too. Let’s have some fun. I am going to make us girls lay back and let the boys do the work. They can take turns sucking, licking, and fucking our pussies till we squirt!

Let Mommy Suck You

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I know I should be more modest but my mommy pussy always craves little white cock. Mommy knows she should behave and be a good girl bit it’s so hard if I see a young one riding his skateboard or jogging with their track team. The way their little manhood bounce up and down with every step makes me want to invite one in my house for lemonade. There he will be greeted with my juicy lips trying to find their way down to his semi hard cock. Mommy will take good care of him as long as by the end of his visit he gives my sticky, gooey, wet cougar pussy. I love the feeling of a hairless face rubbing in between my legs! When I’m done with that hot young boy toy he will want to visit mommy after every one of his workouts!

Tongue-jack Mommy’s Shitbox

mom fantasiesAll bent over smack dab in the middle of the room. You find me checking out my hot round milf ass. Touching my toes as that pink spider winks at the both of us. So you just going to stand there? Or do you want to tounge-jack this mommy’s shitbox? Yeah, get over here drop to them knees beneath me, pull out that tonge and work it up one side of my ass cheek and down the other. Making your way right to my asshole and drive it deep inside of me. Open wide as I ride your face with my fine milf ass. Bet you never imagined ass to taste so good did you? What’s that…you want Mommy to feed you seconds?

Mommy Phone Sex or Sissy Mom Sex?

mommy phone sexSundays are mommy phone sex days.  Mommy gets dressed up in her Sunday best. Maybe you get to see her putting on her sexy pantyhose. Or catch a glimpse of her in her sexy undergarments. Are you turned on or jealous that she gets to wear such pretty things and you can’t? A sissy mom would never punish you for wanting to play dress up in her clothes. She would actually encourage it. I have 6 sons and not all of them share the same fetishes. I have two boys that love mommy’s panties, but for vastly different reasons. One of my older sons was a panty stealer. He would take them out of my dirty hamper to jack off in them. He loved the smell of my ripe pussy, the flavor of the cotton lining. Like most teen boys, he was just curious about mommy’s pussy. Once he got to eat and fuck the real thing, he lost interest in my panties. My youngest son from my first marriage however, liked more than my panties. He liked all my sexy clothes, my shoes, even my makeup. He is a sissy boy, but I love him. I encourage dress up. Even gave him a girl’s name since clearly he is more of a daughter to me than a son. We shop together for clothes, he even fluffs some cock for me and does little sissy maid tasks. Sometimes I am a very nurturing mommy, other times I am getting off on publicly shaming my sissy boy. So if you like mommy’s panties for reasons other than mommy’s pussy, don’t feel ashamed. You just need a sissy training mommy to help you be the best sissy you can be. Who is ready for dress up time? Sissy school is now in session.

Remembering The First Time

jack off with mommy Since the other night when “Mrs Jones” made sure to add a special twist to the end of our role play, I can’t stop dreaming about that day so many years ago.

As my eyes close I am transported back to that hot and muggy afternoon in the woods.  It was the end of summer and we wanted one last fling before we started our last year of high school. A camping trip by the river sounded like a great idea. One of my friends had just gotten a beautiful German Shepard and insisted that he come with us “for our protection.”

That afternoon I went out to the woods like normal to relieve myself. Making sure I was in a well secluded spot, I used the little shovel and dug a hole before pulling down my shorts and panties and squatting down. I heard leaves rustle behind me and I remember being annoyed that one of the boys had followed me. Suddenly I felt his cold nose sniffing my ass. Before I knew what was happening, I felt two heavy thuds on my shoulders and a stab of pain as his cock entered my ass. I couldn’t scream out. What if someone came? I would never hear the end of it. I am not sure when I realized that I liked it. No I fucking loved it! My fingers were in my pussy and it was soaking wet. He was hitting it hard and fast, panting in my ear. I felt his dick growing inside me, getting fatter. A sensation that I had never felt and it felt so fucking good…I started to cum all over my fingers in hard squirting spurts and I felt him shoot inside me. I had to hold myself up, I was panting and out of breath. I had never had an orgasm that made me squirt before. It was very intense.  That is when I realized that he was stuck, his dick had gotten mighty fucking big.

I was glad that we had that time so I could collect myself before returning to the group. I knew this was just the beginning of my experimentation….

If he had known that bringing home the the beast for “my protection” would make my knees weak and my pussy wet as it took me back to that camping trip, and ultimately changed our Mr and Mrs Jones role play, I wonder if he would have gotten him for me sooner…..

 

 

Mommy knows how to take care of you!

jack off with mommyAwwhhh baby boy, don’t you worry, Mommy knows just how to take care of you! I have been around the block more than a few times so I know exactly what that cock needs and I am so not afraid to give it to you! I will suck your balls dry and fuck you until you simply can not fuck anymore! Mommy will make you feel oh so good… and I will teach you a thing or two as well. It is very important that a boy like you learns exactly how to treat a woman, trust me all of your future girlfriends will thank me! I have everything you need right here baby, so what are you waiting for? Mommy doesn’t want to wait here all day!

Guide to pussy play

Mom phone sex (2)

 

  Mommy has been showing the little ones all about pleasing herself when there is no dick around. I shove my little toys in my pussy to hit my spot and then I show the girls. I walked in on Lilly practicing last night she was on all fours ass up pussy up just like I am. I walked in saying how proud I am that she is learning how to please her self as well as taking my direction. Her pussy looks just like mine and mommy is so proud . I sure did make a trio of hoes and pretty pussies. Wet, tight, sexy pussies at that. Aaron my long time friend loves to have the girls sit on his lap and watch mommy play with her pussy while he plays with their little bald pussies. Its a great show I love talking about and that’s why I do phone sex. Its a great experience. Lets talk about what id make the girls do to you. This is what I love to do. Make everyone happy, be a great sex guide and fuck. Who doesn’t like to study pussy and play with it. 

 

 

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At the Beach with my Boys

Milf fantasy stories

I took my favorite boys to the beach.

It’s my favorite place ever. Especially when I get to watch my son and his friends run around in soaking wet shorts and no shirts.

It’s such a sexy feeling. Wearing a bikini, getting all that sun, watching those young things run around. All those muscles shiny with sweat and those shorts that stick to their young cocks showing the outline.

It makes my pussy so wet to think of Max, Kyle, and Ronin all touching. Sucking. Fucking.

It’s easy to get them to cum to me when I’m horny. I just take off my bikini top, stretch all long like a cat. Let my nipples get warmed up in the sun.

I never have to wait very long before I find one of those handsome young men pressed up against me. Grinding a hard cock against my hip as they sucked at my breast, fingers reaching down my bikini bottoms and touching my pussy.

Then another set of hands and lips. These ones kissing my stomach, pulling my bikini down over my ass and down my legs. Stripping me naked as the sun is blocked out by the last boy. I take off my sunglasses to look at my three Adonis and all their cocks hard and dripping precum for me.

Max always starts first, moving himself between my legs as Ronin moves himself over my mouth while takes my hand, jacking himself off with it over my tits.

I love all these boys. Fucking me on a beautifully sunny day on the beach.

It’s the best vacation that a mommy can ask for.

Lots of swimming, sun, fucking, and sand.