Category: Sissy training

Happy Groundhog Day. Goodbye Winter Woolies.

sissy training

Today is that stupid Yankee rodent day. I hate fucking rat looking creatures but daddy says I must respect tradition. His groundhog day tradition is very much his own and it is so much more fun than watching for a shadow. Our family tradition is that on Feb 2nd Daddy will come around and check his girls pussies. If her pussy hair is thick and winter-nasty, she doesn’t get any Daddy cock. If it’s all smooth and waxed, her eager little beaver gets some winter wood. Of course, I’m joking.
Feb 2 does mean something though. It means it’s almost Springtime and time for those sweats to be packed up and all of that hair to be gone. Bikini season is right around the corner. That means you too, crossdressers and sissies. Time for the tanning bed and the wax. If you’re gonna compete for the finest cock out there, you’ve gotta get your game on.
Let me be your sissy trainer as we do our female hygiene. I can teach you step by step the best way to shave those balls, tweeze those anal hairs, get rid of that winter butt acne, and make you into an enticing and tasty little whore. Allow me to coach you. I can even pick out your lingerie and panties for you from my own wardrobe. I may be young but I know what big Daddy loves. Let me be your new best friend and teach you how to be a sexy girl.

New Lingerie for my Sissy

sissy phone sex

I couldn’t resist. V-day is almost here and I just love new lingerie. I stopped by the new VS store just to see what they had on display. Whoa, my pussy got wet just looking at the stuff. It was hotter than a panty boys dream in there. Even the cashier was looking good enough to eat in a bustier. She looked my body up and down and said she had just the thing for me. “It’ll make your man stand at attention.” she smiled. She led me down rows of silky lacy things. Matching bras and gartered surprises. Silk stockings in an array of colors. A smorgasbord of delights for the senses. Sultry perfumes. Mmmmm, I was getting giddy with desire.
And then we were there. It was a secret world tucked in the back of my mind. I was surrounded by men admiring my lace clad body. They reached for me and I felt the heat fly from their fingertips. My body was caressed by unseen fingers that made my nipples hard and my pussy slick. One beckoned me, bringing my face to his cock. I opened for him and tasted the sweetness of his pre-cum. Another lifted me, pressing me against the wall. I felt the tip of his penis touch my slit and I moaned. A shudder ran through my body and I cried out for what I needed.
Suddenly, I was back on the lingerie aisle, alone, flushed, holding a silk camisole and matching panties in my hand. I knew I had to buy it. Somewhere in Victoria’s Secret I had discovered a whole new dimension into my sexuality. I would be a goddess for Valentine’s Day. Welcome, all you panty lovers and sissy boys. This year is gonna be different. Let me show you the selection of fine panties that I have for you for Valentine’s Day. It’s the biggest panty sale of the year. Don’t miss the fun.

Mommy and her boy toys.

mommy phone sex

Sure, I’m an AB/DL mama but I’m really just a slut at heart. Being a Mommy just means that I get my pick of the youngest, hardest cock. Who doesn’t want to fuck their mom? Seriously, boys, Mommy was your first love, your first glimpse of titties, and is probably responsible for the first hard-on you ever got. If not your own, mommy, then certainly your best friend’s hot mama. So, quit denying it and let’s talk about it. I love roleplaying your mom. You get to tell me all of the juicy things that you never told your own mom. Plus, I’m way better. I take good care of my fetish boys. You want mommy’s panties? Tell me and I’ll get them for you. Fresh, smelly cunt fragranced ones that are sure to feel good on that throbber when you jerk off into them.

 

incest sex
Imagine when you were a boy. You were lying in bed and you heard your daddy driving his fat cock into mommy’s pussy. The bedsprings squeak. The headboard bangs. Your hear mama’s sweet voice begging for cock as Daddy dumps a great big load into her gash. Your hand is beating your cock furiously as you angrily jerk off. You just know in your little boy heart that you can please mom so much better than him. You want to see Daddy get cuckolded, demeaned, forced to watch as you fuck his wife. You want mommy to know that your bigger cock is so much better than his. You wanna know the truth? Mommy knows this and she is waiting for you to make the first move. She hungers for that young bull cock that can cum over and over. She rubs her own clit when she hears you moan in your room or finds her cummy panties in the hamper.
So, make that move, sweetie. This mommy is horny and hot to trot. I want to hear all of your fantasies and desires. I would never laugh at you. Let’s get off together.
Love,
Mama Helen

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Bubba is my new sissy.

brother / sister phone sex

Just a small runner in my pantyhose and my day was ruined. Now I had to pull them off and put on another pair, trying not to tear the new ones with my freshly manicured nails. I tossed the torn offenders in the trash and headed out the door to class.
I got home a bit early and the house was quiet except for a strange little sound, like a youngster giggling. Walking past the kitchen, I noticed that my torn panty hose were no longer in the trash. This was too weird. I snuck upstairs, thinking that maybe someone had broke in. I moved cautiously down the hall, hearing the falsetto getting louder. Then it hit me!!! Bubba had taken my damaged pantyhose from the trash and was up to something. I peeked through the door and nearly fell over. That asshole had pulled my pantyhose on and was wearing a pair of my dirty panties on top. He has also managed to stuff his fat feet into my favorite heels and was strutting like a faggot in heat. I threw the door open and he nearly fell over. His cock hung limply through a tear in the panty hose, allowing him access to it. I could tell that he’d been jerking off all day.
“So, you wanna be a sexy bitch, Billy?” I tried to act tough. “How bout I tell Daddy what you did today?” He began to whimper. “Please, sissy, I just want to be a girl. I’m not like other boys. I’m a panty boy, a faggot bottom.” I turned white. How did I miss this? I went to him and hugged him. I had a sister and she needed cock. I ran to my room and returned with my vibrator. “Come here, babe. I wanna break you in.” The look on his face was priceless. His cock began to rise as I lubed up the thick dildo.
We spent the rest of the day in his room. I stretched his new boy-pussy and taught him to suck cock. Finally, I fucked him up the ass as he jerked off. It’s gonna be so much fun having a new playmate to dress up and fuck. I can barely wait until he gets his first piece of real man-meat served right up the ass. I’ll be right there to suck the cum from his newly violated pussy. It’s what a good sister does for her cock-loving Bubba.

incest sex

A fun night out with “Allison.”

kinky phone sexWatching him flounce across the floor made me giggle. He really needed a girl like me to help him. “Oh, Allison, you are doing it all wrong.” I said, tucking his cock back into his panties. “If you wanna learn to suck cock, you need some lessons.” Allison, of course, was all fucked up and called me a bitch. I leaned in closely and whispered in her ear. “Baby, you know you want this big dick, right? Let me show you how to get it.” I approached the big bull nigga and slid my hand into his baggy pants. He flashed a gold tooth and looked at us. “Mmmmm, fucking white meat. You gonna give Daddy some head?” I took at Allison and she flushed red, obviously high and horny. I nodded towards the back room and he followed us. “Ok, Allison, here’s your chance to get some BBC.”She whimpered a bit as I rubbed the blacksnake against her cheek. Allison opened wide and a sprinkled a little meth on the cock and shoved it in. I heard her gurgle as the big nigga began to violate her face. Fondling his nutsac, I urged him to feed my bitch. It was all Allison could do to keep up with the pistoning meatstick that pounded her face. I reached into her panties and stroked her cock as she got her fill of man meat. Our black joystick began to moan. “Eat my cum, you white ho. Swallow it.” Allison’s hot little mouth was filled with gobs of fuck sauce as she humped her own load into my hand. I licked it clean. Her jizz was delicious. Knowing that I had helped my friend get some cum really made my night. I was juiced and ready to find some of my own now. Allison and I were hot to trot tonight!!!

sissy training

Footie Fucking Specials

barely legal phone sex

I was at the mall shoe store when I saw the cutest shoes. They were sexy wedges like you would wear with a short sun dress. I had such gotten a pedi 30 mins ago so my feet were looking great. I wanted to try them on. I wandered in to the dead store, looking for a salesperson. It was like a ghost town this early in the day and finally a lone employee crawled out of the back. His eyes lit up when he saw me. “Welcome. How may I help you today?” he smiled. “I’d like to try on a pair of shoes, the wedges in the window.” I said. “May I check your size?” he asked, pulling out the measuring device and taking my foot into his lap. Without thinking, I wiggled my toes and set off a chain reaction. With wide eyes, he looked at me and I felt my foot touching a large, hard cock. “I’m sorry, ma’am. Let me go get your shoes.” he whispered. I decided to jack with him. I took some lotion out of my purse and poured it over my feet, rubbing it in quickly, leaving them slippery. When he returned with my shoes, he took my foot into his lap, eyes widening when he felt the smooth lotion.
“Ooooh, you have such pretty feet.” he said, kissing them. “Show me.” I whispered, wiggling my toes obscenely. His face was fiery red as he took out his cock and rubbed it against my silky soles. I could hear his breath as he held my soles together and fucked me like a foot pussy. My own cunt was wet and I reached up under my skirt to touch myself.
Thank God no other customers came in, because we were lost in footie heaven. He blew a huge load of cum all over my feet as my pussy gushed. I love the way it squished between my toes as I slipped into my new shoes, bought with his employee discount. I had a feeling that I was gonna be doing a lot more shoe shopping in the near future.

kinky phone sex

I Am Honored

kinky phone sex darlaShe took her time finding just the right one and that one was me. She just wants to serve me in every way she can. I am so flattered that I will have her at my beck and call at all times. So far she has been such a good sissy that I went out and bought her three pretty new dresses with matching panties and accessories and three new nighties. Tonight she cooked me a wonderful meal, made sure I was comfortable after diner while she cleaned up and then took me to my candle lite room where she  laid me down and gave me the best massage and pussy licking ever.  it was the most relaxing and pampering evening! Now that my pussy has been licked clean and I am drifting off to sleep, I am thinking about what tomorrow will bring.

Cruising with Mommy on the Good Ship Lollipop

mommy phone sex

Just got back from a cruise and Mama is feeling good. You’d never believe what I met on this ship. A whole group of AB/DL sissies!!! Yes, a group, and they had no mommy chaperone with them. I knew this was my opportunity so I introduced myself as a mommy. I saw the eyes light up as they took me back to their connected room. Poor little boys had no one to take care of their needs. Seems that mommy bailed out at the last minute. I immediately pulled out a milky breast, fed the hungry ones, and did diaper changes. They were soon goo-goo’ing happily as I stroked boy cocks and made them cum while being rocked. The whole cruise totally rocked as my boys paid for everything. Sitter fees are high, you know. I spent most of the nights in their rooms, milking swollen cocks of their cum. There’s nothing like some mommy sex to make a boy sleep good.
Wanna hear more details or do an around-the-world cruise with Mama, give me a call. I will sing you lullabies, and rock you to sleep right between my hot mommy thighs.

A well dressed Pet must have a collar.

grandma phone sex

It’s Dress up your Pet Day and mine has the cutest outfit ever!!! I bet you thought I was gonna have a chihuahua in a sweater or a poodle in a tutu, right? My pet, however, has 2 legs, is obedient, loyal, and even does tricks to make people laugh. I first found him as a little panty thief, stealing my lacy things and jerking off in them. I busted that ass hard and made him wear them, and he has been my personal pet ever since.
Today he has quite the wardrobe. Studded collars, jeweled muzzles, an e-collar to punish him (AKA Cone of Shame) He has frilly lace dog panties, sweaters with hearts. He even has a tuxedo with the cutout for his wee-wee. Every girl loves a sharp-dressed pet!! I even put on some doggie cologne to get rid of the man-smell.
Lessons have trained him to be obedient and punishment is often given. No one wants an unruly pet. I’m a firm owner who doesn’t hesitate to bust ass with a shoe, a rolled newspaper, or my bare hand. Are you ready for your new owner, sissy? My kennel has plenty of room for a nice little doggie like you. Is your bark worse than my bite? sissy training

Feasting on some Man Flesh

kinky phone sex

What my eyes can behold. It’s the Feast of fabulous Wild Men Day. That means that me and the girls are headed off to see the strippers tonight. Hot bodies and maybe even some harder cock. Us girls have it made. We can run our hands all over these luscious men, bury our faces in balls, and let him hump our ass. Maybe you’d like to be my dream man, sweetie, and shake that cock for me. Stick it right in my face and let me breathe on those balls. My tongue flicks out quickly, tasting a drop of pre-cum from your head. I smell your musky man smell and my pussy weeps just a little. You pick me up and bend me over, grinding your semi-erect cock against my panty clad ass. I throw money at you, screaming for more. You push my head down into my BFF’s lap, making me “eat” her pussy. She grabs me by the hair and I realize that she likes it. I am on fire now, dancing, grinding, with all of the other horny bitches who are drooling over young, firm bodies. My fantasy takes over and we are all naked, smooth pussies, titties quivering. You dip your cock into us, one by one, and then force us to lick you clean. Finally, you order us to our knees, jerking your massive fuckstick, balls drawing up tight, until your purple mushroom explodes onto this row of cum-starved, horny sluts. Your cum rains down on us like a firehose, our tongues extended, ready to taste your bounty. Just a bunch of girls out for some hot sexy men!!! Hope our men never find out!!!