Archive for the 'Sissy Phone Sex' Category

Page 18 of 45

Mommy Debi’s Little Play Thing

 I decided a few months ago I would love a girly little plaything. Not exactly a girl but close enough for her to be soft and feminine.  A close friend of mine was going away for the Summer and asked if her son could stay with me as I have so much room in my house.  We discussed the situation before she made her plans and she agreed how she always wished her boy had been a little girl.  Jen got special hormone pills for her son the next day.  By the time he came to stay with me he was already showing signs of losing his manhood.

Within a week after his dosage was upped he could no longer fit in his boy clothes as his body was changing.  I came home from work to find him sitting on my bed with girly clothes he just felt he HAD to purchase and a confused yet excited look on his pretty face.  It was time for the talk I had been eagerly waiting for.  I told him to take off all his clothes and take a good look at his body in the mirror. He was very embarrassed but I stroked his blonde hair that had grown down to his shoulders.  “Your mommy has been giving you pills to make you into a girl”, I told him.  I stood behind him pressing my big boobs against his back and kissing his neck. I explained to him that while I loved men I also wanted a girly boy to play with. I began to play with his tiny cock, rubbing it like I would my pussy. He moaned and I could feel him getting wet.

He was excited and ready to try on all the lingerie he had purchased. “Not yet, baby” I whispered in his ear. Mommy Debi is so horny and she needs to feel your sweet soft body rubbing against mine.  He laid down on my bed and I kissed my way down his smooth body. His little boobs were so yummy I could not keep my mouth off them.  I got on top of him rubbing my dripping hot cunt against his. He thrust up his curvy hips and slid his tongue into my mouth. We both came so hard and loud I imagine the neighbors even heard us. Now I have the little girl lover I always wanted.

Let’s Make Our Own Fireworks

I’ll be bringing this 4th of July in with a few big fat cocks for us. My assets are always bringing in big sticks of dynamite. The real fireworks will be going off when my little sissy sluts get on their hands and knees and start fluffing the cocks that will be banging my cunt tonight. I’ll be stuffing your mouth just like you’ll be doing at your family BBQ today. My treats are much better! I know you’re willing to do more for me and you’ll be begging me for them to explode in your mouth. You know better and that’s a big fat NO! You can clean me up when they are done exploding loads of cum in my cunt.

Sierra

Is it okay to laugh?

I have a funny new caller. Just hearing his voice cracks me up so bad I get the hiccups. He is a panty boy and I do love my panty boy callers. He likes for me to dress him up sexy and to take him to the airport. Even though I am barely legal he calls me Mistress. I am a very bad girl and some of the time I make him get drunk and try to walk in his stiletto heels. Between you and I, he falls down a whole lot.

Last time was the funniest EVER!! We were really getting into things and other panty boys joined us for him to train. He was so girly even trying to tell them what was expected of them. His voice is not what you would call commanding. Then it happened…..wait for it. He moaned out in his most girly voice ” Tell me to make love to my right hand”.  ROLFLMAO!  Then like a good slut he licked up all his cum.

Let’s play dress up. You know you want to.

Wicked little Amanda

Dress For Your Mistress

I came home from school and found my step daddy going through my things. My sexy lingerie was tossed all over the bed and floor. I threatened to tell on him for being a pervert but he begged and said he would do ANYTHING if I didn’t tell her. I was still rather confused so I told him to tell me what he was doing before I figured a punishment. He explained he wasn’t perving on me but  he loved to feel pretty and sexy in girly clothes.

I told stepdaddy that to begin he must always call me Mistress and hand over his credit cards. I mean if he is going to wear some of my lingerie then I would need lots more. He offered to take me shopping and was so very eager. He helped me pick out several silky panties, cami’s and bras. I found a few corsets and garter belts as well.

We went to the counter to pay and there was a real cute girl around my age. She said that what a nice step daddy I had to buy me so many sexy things.  “Do it”, I whispered in his ear.  “Please Mistress Amanda, don’t make me say it. It is way too humiliating”, daddy said. I told him he better do it, as the sales girl  was starting to get impatient with a line forming behind us. “These are for me, because I am a little sissy slut”, daddy said. Everyone started laughing. It was so much fun!

Sissy Faggot Bitch!

I am a Goddess. Superior to you in every way, shape and form. So explain to me why you have your hand inside your panties in my presence, you little fucking faggot? Your tiny, pathetic clitty right underneath your fingertips? You should know better than to make a wet spot in those panties without permission. You need to be disciplined.
I’m going to tie your slutty hands behind your back so you won’t be tempted to touch your pussy. There. That’s much better, but you need something in your mouth so I won’t hear your protests… Eat a dick. Take this big, black dildo, sissy… and suck it like the whore you are. I’m going to choke you with it while I slip my fingers into my own panties and make you watch me finger myself. I find it so amusing to see your eyes water and hear you gag.

I notice the wet spot on your frilly little knickers is growing bigger. This calls for serious punishment. I roughly stand you up and pull those panties down and remove the wet dildo from your mouth. I slide it across your pussy, pretending I’m going to be gentle… but you need it rough. I shove it swiftly into your sissy hole and start pumping it in and out of you, telling you what a little fucking depraved faggot you are. I release the bonds from your wrist and tell you to play with your clitty. That’s right… you do it behind my back, so you might as well show me to my face. I laugh as your clitty starts to squirt, making a tiny little puddle. Clean up that mess, sissy. Clean it up with your tongue.

Small Penis Humiliation

I say penis for a reason. You don’t have the privilege for “it” to be called a dick or a cock. I don’t even think penis even suits you. With losers like yourself, I like to dress you up in panties and show off your little clity. I really can’t hold back the laughter when I see you strut around like a little loser sissy.

You and your clit are totally worthless to me and if it wasn’t for my amusement and entertainment you would be gone.

I won’t deny that you are good for some things. For instance, having you there when I bring one of my black boyfriends home. I take you into my bathroom while my black lover waits and I dress you in one of my sexy pair of panties. I get out my favorite M.A.C lip stick called Relentlessly Red and I put it on your lips and then write on your chest “BLACK COCK SISSY SLUT”

I have you go out in the living room greeting my friend  wearing only panties with your hot red lipstick and my note on your chest. I make you suck his big, black cock while I get ready for him.

I like hearing you gag from in the living room while I slip on some sexy lingerie and heels for my black stallion.

I guess having a small penis does come with benefits but you might not agree at the time you’re being choked by my 13 inch black beast.

In the mood for a panty boy

I’m at home, feeling a little bored and wishing I had a little sissy to entertain me. I love to take those confused little panty boys and play with them. I bring them in and dress them in my pretty lingerie. They try to resist, but I can see that bulge in my silk panties. They love it. The last thing they need are pretty red lips. How can you be a proper slut without red lips? I sit back on the couch, propping my legs up and command them to stroke for me. I want to see them fill my pretty silk panties with creamy cum. Sometimes I’ll invite some of my girlfriends over to watch with me. We sip wine, point and laugh. They always stroke furiously, wanting to cum so the embarrassment will be over…. but I have a surprise for them in the end. Once they shoot their load, I make them take off those panties and clean up every drop…. yum.

Professor Sissy Slut

School is finally almost out for the year. Daddy said if I kept my grades up he would pay for  me and my friends to tour Europe. Of course daddy is doing this to help me with my BA of Arts degree.  Don’t get me wrong going to Barcelona, Prague, Paris and London to see the galleries is unreal. We just have to plan things out so there is plenty of time to party.

I only have problems with one of my Professors. This “problem” needs to be handled quick as daddy has a meeting in a few days before he books our flights and hotels.  Today is the day I seduce Professor Jacobs.  I have been sitting up front in the sexiest little outfits trying to get his attention all year. He hasn’t once looked the slight bit interested in me.

I quietly knocked on his office door but there was no answer. I opened the door and peeked in and saw the reason he has no desire for me. Professor was down on all fours wearing panties and a bra taking cock in both his holes. The boys looked familiar I am pretty sure they were a grade younger than me in high school.  I quietly watched so no one knew I was there then started taking loads of pictures. It was hard not to laugh but the more evidence to ruin him the better.  When the boys were finished with Professor Sissy Slut I let them all know I was there.  The boy ran out and I told Professor just how things were going to be. He stood in front of me with cum dripping out of his fuck holes completely red faced.  He agreed to anything I asked for and sat at his desk still in panties writing a stellar letter of recommendation to show my daddy.

First Time For Everything

My step-brother has been having some problems with my parents. He had asked if he could stay with me for a few days to sort things out. When I was going out last night I knew he was going to have some friends over. I was totally fine with that. What kind of trouble could they possible get into? When I got home I was shocked! I walked into my bedroom to find him and his friend standing in front of my mirror wearing my clothes. They had the nerve to wear my dirty panties! I was so mad I made them strip down to nothing but the panties. I took a few pictures just in case I need to blackmail them. It’s so much fun being big sister. I could see that no one at my parents house teaches them a lesson. I sat down on my bed and each of them took turns laying on my lap while I gave them spankings. I was teaching these filthy perverts a lesson. If they want to continue to  play with my clothes and make up they need to ask permission first.

They are only to wear them around my house on the weekends so I can turn them into sissy sluts.

Callie

A Glamorous Transformation

Your beautiful, glamorous, and classy. You’re truly a queen. I have transformed you into a beautiful elegant woman. Not to mention, I’ve trained you to be the best cock sucker in town. So obedient and always ready to please. With a snap of a finger you drop to your knees. Your beautiful red lips inches away from his throbbing cock. Your elegant hands and your freshly manicured finger nails wrapping around his enormous package. I love how excited you get. Your face glows as you look up at him batting your eye lashes while you take him in your mouth like a good sissy slut.

I’m so proud of the woman that you have become.

Faith