Category: 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

 

Family fun phone sex with a cucky twist.

family fun phone sex

My poor husband has such a small penis. Me and the girls tease him all the time about it. He’s a good man but he just can’t fill up a pussy. The girls don’t mind so much because they are young and tight. Daddy’s cock still fits them just fine and they are still eager to please him. But I need more. Thankfully, he is a very understanding man and allows me to find exactly what I need. A big thick 10 inch joy stick. I bring one home every month and fuck it right in front of hubs. It gets him off too, watching his wife gape wide open with a strangers cock pumping in and out. He gets so excited that he’ll have one of the girls come in and suck his cock while he watches me. In a warped way, it turns me on too because it shows my daughter what a real cock looks like. I know that soon she’ll be asking for one too.

I look up at you, my cock God, and I see the excitement on your face too. You love being the center of attention as you ram me deep and hard. The veins stand off on your big stick and the purple head is swollen. I tease you just like I tease my own spouse. I lick your full balls and gobble your shaft until you can take no more. You lift me up in your arms and toss me on the bed. I spread wide as hubs watches, his small nub rolling between his fingers. I feel the burn as you push inside and the bull thrust that bottoms me out. I scream in pleasure and in pain. You show me no mercy as you take control, growling as you slam me over and over. I hear my husband gasp as you pull out of me and splatter my face with a massive gusher of cock cream. Licking my lips, I beckon Mr. Tiny to join us. He knows what his job is and he licks every bit of cream from my face and tits. Meanwhile, you are hardening for Round Two watching my pathetic cucky lapping up your sperm. And guess what? The girls will be joining us for this round. It’s time for some real family fun.

incest sex

 

working out and fucking all in one

 

 

incest sex

 I work out making sure I keep my ass tight for my bubba to grab and spank when I’m naughty. We even have our fuck time in our work out room. This is where the magic and work happens. He actually took this picture of me. We were just about to get real nasty. We both are very strong my legs are stronger then my arms so I can straddle him and be on my feet just fucking that cock nice and hard .

He loves to see my fat ass twerk on his dick. He doesn’t even have to put it work until its his turn I love fucking my brothers dick. Then he will bend me over on our bench press and fuck my tight pink pussy. We put in work- out time and fuck time. Its a whole day process. I love getting all sweaty, working out and getting fucked makes my body feel alive. Would you want to work out with me and let me fuck your dick? Because I’m game !

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

The hazards of being a student nurse.

barely legal phone sex

I bet you wish your nurse looked like me. I’m a student nurse and I want to tell you about my day. I was required to spend 8 hours at the local hospital in Houston, getting the experience I need to graduate. We were to be assigned to care for a particular patient and manage his daily care, documenting our findings. Mine turned out to be an older man, married, who was in for bypass surgery. He reminded me of my own sweet dad.  I heard him arguing with the charge nurse about not wanting some damn student caring for him. I heard her laugh and say “Oh, but you will like this one.”  When I walked in, his mouth flew open like he had never seen a pair of tits before. He was being the model patient, letting me take his vitals and do an exam. I even let him cop a feel of titties. Next, I told him it was time for a bed bath. I went to get a tub of water and my supplies and came back to see a huge bulge under the sheet. He was grinning as I pulled the sheet back and started to wash him. I admit it, I was getting turned on. I began to wash his cock and balls and he moaned. He slid his hand up under my skirt and touched my pussy. I was soaking wet. He pulled my head down and urged me to suck his cock. I did. He had a thick cock with a mushroom head. I couldn’t resist. I climbed right up on his bed and straddled that cock, pulling my skirt up, and squatting on his thick shaft. “Fuck me, Daddy.”  We almost broke that hospital bed. He was gasping and wheezing as he blew his load right in my greedy cunt. As I hopped down and finished his bed bath, his wife walked in the door. He grinned at me as I walked out the door, still feeling his load oozing out onto my panties. Oh, the hazards of being a nurse!!!

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.

Aunt Helen loves fucking her nephews

aunt phone sex

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.