Category: Sissy training

Aunt Helen loves fucking her nephews

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Wow, do I have some hot nephews. My brother and sister both have young boys and they are looking fine. I was checking out the bulge on my teen nephew this weekend. We were all in the pool and he was wearing a Speedo. His lithe body and young muscles had me soaking wet. My little brother saw my jaw hanging open and laughed, knowing what I had on my mind. We had always been a sharing family and nothing was too taboo. He had lost his virginity to me so why not his son, too. Perhaps he would enjoy participating in the training. I knew his wife would not be pleased so we waited until she went to bed that night before we talked. When he walked into my bedroom with his son that night, I knew I was in for a treat. Dad showed his son my pussy and what to do with his cock. In the end they were both buried in me. One in my mouth and one in my cunt as they fucked me back and forth like a father-son competitive event. I went to sleep one happy aunt knowing that our family tradition was being carried on.  Every nephew needs a horny aunt like me who is total cum freak. I’m hoping the other one will be home tonight so we can have a third cock for even more family fun.

Grandma phone sex and her cucky son

 

“Shake them big titties. Let me fuck those stripper tits.” he moaned as he slid his cock back and forth between my watermelon breasts. I may be a grandma but I can still rock that cock!!! I love them young. My son still keeps Mama well fucked but I need more. I have a big cock fetish. Big, thick and juicy. I don’t discriminate on race or age. Bring me a small dick and I’ll put you in panties and cuckold that ass.

grandma phone sex

I remember the first time I saw you and your jumbo cock. You were a bit shy and I could tell you weren’t experienced. I made the first move, placing my hand on your thigh. Once you warmed up, though, it was like holy fuck. I pulled that fuck-monster out of your pants and my furry cunt got all wet. I wrapped my lips around it and tasted your pre-cum. You were grabbing my hair, trying to push the entire thing down my throat. I slurped and gagged, trying to keep up with your thrusts.  “Show me your pussy, mama.” you whispered. I kicked off my leggings and you gasped when you saw my wooly bush. Most young girls wax that hair off so I knew that you’d never seen one like mine before. I stretched out on the couch and spread my fuzzy lips. You were on me in seconds, pushing that 10 incher into me while you sucked a big tit. I felt your girth stretch me open and I knew I was addicted. It was nothing like my son’s 7 inches. I’d never be satisfied with that again. You began to pound me hard, pushing it in to the hilt. My pussy squirted as I came hard. I felt you began to throb. That beast was gonna blow!!! You began to whimper, “Mommy. Mommy. I need to cum.”

Just then, the door opened and my son walked into the house. Seeing the size of your cock, he sat down into a chair and pulled his small one out. The fun was just getting started.

Cougar Phone Sex

cougar phone sex darlaShe is a few years older then me and Harley loves her. I have used her a couple of times as a sitter and I liked the way she let’s Harley dress up and become Hailey. She seems to enjoy the way he changes and becomes sweet and feminine. Last night I came home early and heard them in Harley’s room. looking in I saw my sweet little Hailey laying on her back on the bed. She had his little clitty in her mouth and a hand between his legs playing with his little mangina. The sight of this older woman pleasuring my little boy. his little body squirming under her touch. I felt the rush of cum soaking my panties. I wanted to join in but I didn’t want to interrupt. I was captivated by the sceene in front of me and ha my hands down my panties finger fucking my horny pussy. Just as I was thinking that  Harley was definitely going to have to lick mommy clean later. He turned his head and looked at me with that angelic smile. He knew I was watching the entire time. joining the cougar in front of me and my sweet little sissy, I walked in and sat on his little face letting him lick me clean while she finished sucking his clitty and fucking his little mangina. Feeling his tongue feverishly working my pussy while I wiggled around was driving me crazy but when he moaned into my cunt I let the rush of cum cover his face and I felt his body jerk as he let his squirty squirt fill her mouth. This is the stuff that hot ass cougar phone sex is made of. Won’t you join us next time, we would love to have you play with us like a good sissy should.kinky phone sex darla1

Mommy sex for diaper boys

mommy sex

My pussy tingles as your lips touch my breast. What a good boy you are today. I can feel you hungrily suck my milk from my udders. I rock my boy back and forth, planning out the  mommy sex activities for the day. Next is bath time and Mama can’t wait to wash those boy-parts. Soapy little balls and oh my, what a big cock. Let’s get you all rinsed off and dry you all over. Then it’s playtime with Mommy.

Oh, don’t you wish those days were still here. Playtime with Mommy was so much fun, but now you’re too old. Still, when you were a teen you lusted over Mom, hoping to catch a glimpse of bare flesh, a boob, or God forbid, a look at that hairy pussy. jacking your cock in the shower, you imagined her coming in to dry you off like when you were a boy. The feel of her soft hands on your flesh is enough to make you hard all over again. Watching Mom sleep, you imagined pining her down and forcing her to take your large teen cock, magnificent in its glory. She would never touch Daddy again if she ever got a taste of your young meat. Only you could satisfy her. You’d be moaning, “Mommy, oh Mommy, please.” as you poured load after load into her sweet slit.

Mommy bends over in front of you again and you almost blow your load. Does she have panties on? She smiles at you and you wonder if she can read your mind. Does she think of your cock in bed at night when you spasm and moan out loud in your sleep. In your mind, she comes to comfort you, holding your face to her breast again and finally, she gives you what you need. That hot milf pussy.

sissy phone sex

Sissy Training my Son

sissy training

My son came to me last night with a strange request. He had been having some homosexual urges and he wanted me to help him explore them and give him some sissy training. We’ve always been very open minded and a sharing family, so I agreed to help. I sent to the store with a list. Panties, lube, and an enema. I bet the cashier was thinking wicked thoughts when she rang him up!!!

We started with the enema. No one wants to mine for poop so you gotta be clean. Once his colon and rectum were cleansed, I brought out my vibrator and the lube. Starting with a small one, I worked him up to an extra large black cock. Still, he wanted more. I began to think he was a greedy little faggot when I brought out my jumbo strap-on. I just rammed it in, making him squeal like a little bitch. Mama is a good sissy trainer but my boy was insatiable. He begged for more and bigger meat. His tight round ass up in the air really got me turned on. I knew exactly what he needed. A good old-fashioned fisting. I closed my fist, looking at it, wondering how much he could take. We were about to find out.

A squirt of lube and I was ready. My hand slid in to my wrist and he didn’t even wince. “More, Mom. More.” he moaned. I pushed farther and farther, halfway up my forearm and it still wasn’t enough. A milky juice began to flow from his asshole with each plunge of my hand. A little more and I was buried to the elbow. His ass was rocking now as he greedily took it all. I slipped my other hand in my panties to diddle my pussy. I was creaming now watching my greedy faggot son get what he needed. My arm was suddenly gripped by his sphincter muscles as his prostate began to twitch. I knew his cock was gonna blow and I had to get out of there. As I pulled my dripping arm from his ass, my horny boy blew a huge load all over himself.

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Here Cums Sissy Cottontail

kinky phone sex darlaLet me share Harley’s favorite bed time story with you.

Once upon a time there was a boy. He always knew he was different, not like the other boys. He would sneak into his mommy’s room and admire all her pretty things. He longed to wear the pretty jewelry and have beautiful dresses just like hers to wear. He would daydream about being able to dress up and go out into the world as a pretty girl. Time passed and he grew up, got married, had girls of his own and worked as big time lawyer. But he couldn’t deny the inner sissy fighting to get out. Yearning for a Mistress he started calling phone sex lines and soon found Princess Levi, the Mistress of his dreams. Finally he became the Sissy he had always dreamed of. Mistress Levi gave Sissy permission to dress in frilly dresses and to wear jingly jangly bracelets and pretty gold hoop earrings. She sent Sissy out once a month for a special day of prancing around in public. A day of humiliation and shame just as she deserved. Sissy grew to love her Mistress so much that she became a piggy pet and the Tinkerbell Transvestite mascot for all Mistress’s girlies at Fuckalicious, Finally Sissy had a home and lived happily ever after being outed as the Fairy Faggot she had always been.

Happy Easter Sissy Cottontail!sissy training sissy

Submissive phone sex with Sidney

Submissive phone sex

My brother likes this tiny little pussy and ass. He loves to lick me from my clitty all the way down to my cute little starfish hole. He loves tongue fucking both of my holes! He rubs my little clitty  with his fingers. I love how he works my clit and my pussy hole at the same time as he tongue fucks my asshole! Getting me ready for his cock. He loves it when I suck on his cock as he does this to me. I sucking his cock getting him shiny and wet with my spit. When he is ready to fuck my tight little asshole, he rubs the head of his cock all over that little starfish hole. It makes my pussy throb when he teases my asshole. I spread my ass cheeks open showing him my hole as he slides his cock inside of me. Stretching my tight asshole open inch by inch makes me moan. He slapped my ass as he slides his cock in deeper tonight tight asshole. I love getting butt fucked by brother. Then cleaning his cock off with my mouth after he fucked my dirty little hole.

Photo Finish

kinky phone sex darla1I love when he comes over and takes pictures of me. As an aspiring photographer he likes to play with light and angles and things and I love being his subject. There is something about it that makes my pussy wetter then hell Add to the mix the fact that he is very fem and I just can’t get enough. I can’t help that I love men that are feminine, shy, soft spoken. I fantasize about what my boy is going to be like when he gets older and my mind wonders in so many different directions. Standing here with cum soaking my third pair of panties so far and we haven’t even been shooting for an hour, I know this is going to be a long night for me followed by the usual get together between him and Harley that I get to shoot.

Happy St. Patrick’s Day!!!!

grandma phone sex

Kiss me, I’m Irish. Aren’t you excited it’s nearly St Patrick’s Day? I love those parties and drinking green beer. Corned beef and cabbage and leprechauns. I’m gonna dress up in my favorite skirt, the one that shows off my big round ass. Going to go find me some cock and let him fuck my puckered hole. I have to laugh. Can you imagine ass fucking after a night of drinking beer and eating cabbage? Kinda gross but erotic at the same time. My older son really used to get off on fucking me in the ass and making me fart on him. He said it felt amazing…that warm blast of air and the way my asshole tightened up. An ass like mine is made to be used that way. It’s like a huge cushion,a real lucky charm, made to be grabbed, squeezed, slapped, and rode hard. Grab double handfulls of cheek as you slide your throbbing cock inside, pushing as I gasp. Don’t stop now. I want my ass fucked full of cum. Can you handle a dirty older woman like me? It’ll be your LUCKY day when this hot momma gets through with you.

mommy phone sex

Humiliation Style Spring Cleaning

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Mommy woke me up Sunday with one goal in mind for the day and I was so not having it. Spring Cleaning? What the fuck is that? Why should I have to clean…?! I immediately thought of a solution…Why not make someone below Mommy and I to clean it? That’s right! Daddy! I laughed and told Mommy my idea, and she was pleased as we went to tell him. We wanted to dress Daddy up Good. We really wanted him to be all cute while doing the spring cleaning…meanwhile Mommy and I planned to sit out by the pool in our bikinis. Just waiting for our friends to come over. These are some of our favorite friends, they all have 12 + inch cocks and they’re so big and magnificent that no one could refuse them. Mommy and I know it’s hard for Daddy to keep cleaning when he can see his wife and daughter getting gangbanged by the thickest dicks you’ve ever seen. Daddy will just know that his is too small and worthless and all he can do is clean like a little pathetic tiny cocked loser. Meanwhile Mommy’s putting her time with some real men to good use and I am following suit, being whores together is our favorite pastime – that and tormenting and humiliating Daddy!

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