Tag: sissy training

Lesson 452: Ass To Mouth

I will never forget the first time a man pulled his dick out of a tight brown ass and shoved it in my mouth to suck clean.

It never occurred to me that Harley had never seen ass to mouth action until today.

kinky phone sex lilly1I was enjoying a lovely threesome with my friends, Jim and Teresa.

As always, Harley gets to watch even if he can’t be actively involved.

Teresa was laying on her back with Jim deep inside her tight ass and me licking and sucking that hot pussy of hers when suddenly Jim pulled out and I guided him into my mouth.

I heard Harley moan from where he sat. I instantly realized he had never seen this or tried it before.

After sucking Jim off a little, I asked him and Teresa if they minded helping me with a Sissy Lesson and they both agreed.

Harley took my place licking Teresa’s pussy while Jim continued to work her ass. This time he waited until he was about to blow his load before pulling out and sticking his dick in Harley’s mouth.

I couldn’t help cumming as they blew their loads together, Harley all over the sheets and Jim in Harley’s mouth.

A Bad Boy Must Wear A Diaper

Ageplay phone sexYou have been such a bad boy. My girls and I know just what to do with you! Bad little boys deserve a spanking. Turning you over my lap, each one of my daughter’s giggle as they deliver one spank each to your bottom. When it becomes my turn, I deliver three swats to the bottom in quick succession. My spanks are firmer than the girls and leave your bottom pretty and pink. Since you can’t hold your alcohol like an adult man and wet yourself, we are going to treat you as a baby. I take the diaper out and begin to put it on your bottom. You protest, but Mommy Gladys will hear none of that. I tell you to hush up with your complaints. The girls love the site of a grown man reduced to an baby. As you begin to speak again, I remind you that babies cannot speak, and put a bottle of milk in your mouth. If you are a good baby Mommy Gladys may let you nurse from her breasts, but you must be a very good baby to earn that privilege. Now don’t you look cute in your little diapee and sucking your bottle! You sulk, pretending to be embarrassed at the situation. I know you are enjoying it though, since I can see the lump in the front of your diaper. That baby cock is getting all hard isn’t it? Yes, I know you love having Mommy Gladys take control. You especially love having your “sisters” see you this way. I leave them in charge as I walk out of the room. From the living room, I can hear them taunting and making fun of you. You think this is humiliating? If this doesn’t teach you to be a good boy, the next step is to take you in public, my little baby boy.

AB/DL Mommy for the brat in you.

mommy phone sex

I’ve been an AB/DL mommy since I started here. I’ve built up a very nice nursery of little boys who need mothered. Being a special mommy has always been natural for me. In fact, my big tits have never stopped producing milk since my own son was born. I love nursing. The feel of a hot mouth pulling my nipples makes me so horny. Sometime I have to slide a hand into my panties to relieve the ache. One of my boys is just precious, a little sissy brat. He loves to be dressed up like a girl. Frilly dresses and lacy panties are the only thing he wears. Sometimes he prefers a diaper but always the kind for little girls. I spoon feed him in his jumbo high chair. That makes him take a great big poopie in his Pampers. I get his mess cleaned up and it’s bathtime. I get to wash his little dick and balls and he always gets hard. He grunts and coos because he knows it’s playtime. I rock him in my arms, sliding a finger into his panties. He giggles because his cock is hard and he loves to play with it. I gently slip a lubed finger right into his boy-pussy and begin a slow stroke. “Fuck my pussy, mommy.” he cries out as he jerks his cock. I don’t stop until he blows a big load of cum all over my tits. Then he sucks it all off. He drifts off to sleep with one hand on his cock and his thumb in his mouth. I know my boy will wake up with a raging hard-on and Mommy will be waiting with legs wide open.

sissy training

 

Harley’s Magical Fantasy

kinky phone sex darla1He was an odd looking little boy wondering in the forest. He was an out cast because he wasn’t like the rest of the boys and he was trying to figure out where he belonged. How he fit in.
Suddenly the heavens opened and it began to storm. He was drenched and cold when he saw the castle in the distance. Running for it in search of shelter he knocked on the heavy wooden door.
The door was opened by a handsome Prince. When he saw the awkward boy he laughed at his awkward appearance and refused to offer him safe haven.
The boy smiled and told him not to judge a book by it’s cover. There is always more to a person then meets the eye.
Just as the Prince was about to close the door a sorceress appeared behind him and pushed him inside. Placing a glass cover on the table she waved her magic wand and an enchanted rose appeared under it.
The glass was sealed by magic and the Prince’s appearance began to change into a hideous beast.
The sorceress told them that they must remain in the castle together for ten years. Each year a pedal from the enchanted rose would drop. At the end of the ten years the last pedal would drop and the rose would wilt. If the Prince could open his cold heart and love for what was on the inside and not on the outside they would both be saved, if not they would both be doomed.
As time passed the Prince learned that the boy had a heart of gold and was kind and loving.
Just before the last pedal dropped the Prince opened his heart.
Something magical happened. The Prince transformed back into his old handsome self, the boy transformed into the beautiful Princess that had been locked within and his hideous penis appeared under the glass sealed away for all eternity.
Sissy Harley became Princess Hailey and she and her Prince lived happily ever after.

Sissy Fun

kinky phone sex darla1The transformation is so beautiful. He walks in wearing his man clothes and his discomfort is viable. Poor dear hates the way he has to pretend all day every day. My heart goes out to him. I have his pretty little pink girlie clothes ready for him. The lacy little baby doll number with matching bonnet make his eyes light up with delight. I undress him and coo sweet words of encouragement as the transformation begins. As I dress him up he becomes a new person. My sweet little sissy. Timid and shy yet so comfortable in her new skin. The role she was born to live. She knows with me she is safe and accepted and my sissy is finally home. I lay her on the bed and pull her little clitty out of her pretty pink plastic panties and begin to rub it. I tell her how beautiful she is and how much I love her. Responding to my touch and my gentle words of encouragement it won’t be long before she squirts for me. My pussy is wet as I hold the spoon to her clitty waiting for her to fill it up so I can feed her the gooey goodness. incest phone sex darla

Sissy Loving Mommy

kinky phone sex darla1Being a sissy loving mommy is what I was born to be. I can’t resist a sweet sissy. The need to please me and be my little girl. The desire to be pretty all dressed up in frilly clothes. The way they wiggle when they walk and the soft lilt in their voices. I love shopping for silky panties and pretty wigs. I love doing their nails and toes in matching nail polish and fixing their make up to perfection. Transforming a sissy and bringing out the girl that they long to be brings me a satisfaction that I can’t explain. I understand their need to stop living as a fake boy and to blossom into the beautiful girl that they are deep down. Mommy Darla is here for you. To hold you tenderly and love your true self. It makes my pussy so wet to see the change as it happens and to watch your eyes go from a dull stare to bright and twinkly. I hope to see you soon my sweet sissy. Mommy is always here for you.

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.

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.

kinky phone sex

 

 

 

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

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.