Category: Sissy phone sex

2 Girl Call Phone Sex With Darla and Jasmine

cougar phonesex darlaLast week a new family started moving in down the street. Every day I would watch and play with my pussy as the daughter carried boxes in. She has that exotic look. Long dark hair, a very cute little body and the walk of someone with a sexual appetite. All I could think about was getting in her pants while I sat here milking my pussy.
I went over and introduced myself to the family. Her name is Jasmine and her boyfriend was there too. I was hoping I hit the mother load. I invited Jasmine over to meet my son using the opportunity of her babysitting sometime.
At the end of dinner I could tell the two of them really were hitting it off. But when he said to her “Jasmine I think you are so pretty. I would like to show you how pretty I can be. Can I model for you?” I couldn’t stop cumming in my panties.
The next thing I knew he was parading around in his sissy panties and dresses looking so pretty for her. I was so proud of him.
We started talking and she really liked the little modeling show. It seemed to turn her on. I suggested that she bring her boyfriend over and we turn him into her own sissy. I asked her if she thought she could talk him into it.
She just smiled and said “For this pussy he will do anything”
Way to go girl!
We went into my room and looked threw all the sissy outfits I have and she picked out what she wanted to see him in.
They will be over in about an hour and his clothes are all laid out on my bed. I can’t wait to help her make him into her very own little sissy so all four of us can play house!

Sissy Boy

sissy phonesex darlaI love spanking my sissy and making her ass all red and hot to the touch. It makes my pussy nice and wet to see her ass in the air and hear her squeal each time I smack that tight little ass. The sound of the crack of my hand on flesh combined with the sequel of pain just makes me dripping wet.
I painted “sissy boy” across that hot, red ass and took this picture to hang in the living room for all to see. And then began to spank her ass some more, smearing the lipstick so that it looked like blood.
I made her kneel for me and worship my pussy, kissing and licking it and sucking all the cum out of me. I made her tell me how she wishes she had a pussy just like mine. How she loves me for letting her wear my panties and how much she appreciates all the silky, pretty underwear and dresses that I buy for her.
Of course she got no relief, not yet any way. later tonight I will sneak in her room and make her satisfy me again, and then, if she is good, I will allow her relief.
I love my sissy!

WTF???

hot phonesex darlaI left for the afternoon to enjoy some time with a friend. As soon as I walked back in the house there she was crying like a little girl.
WTF did she do this time? I mean I know my sissy is accident prone. She breaks things regularly, is always tripping over her self. But never is she sobbing and in hysterics like this.
It took me a good 45 min to find out what the hell the problem was, and I should have known.
I know not to leave her alone for long. I know she needs constant supervision and guidance. But fuck me I never thought she would get into such a pickle.
Pickles. Yes they are the root of this hysteria. I took all her dildos away from her last night because I caught her playing by her self and she knows that is expressly against the rules.
So what does she do? While I am gone she gets the jar of pickles and decides they will have to do. She shoved that fucking pickle so far up her vagina that she can’t get it out.
I will be damned if I am going fishing up her for a fucking pickle.
She is going to have to get her ass in the car and explain to the emergency room doctor why and how she has a pickle stuck inside her.
And I am not taking her anywhere looking like this, she best get dressed proper and fix her make up before we head to the local hospital.

National Men’s Health Month

hot phonesex darlaThinking about my sissy licking my shoes, sucking my toes, prancing around for me and my friends, my pussy gets so fucking wet and I cum so fucking hard. Bottom line is, I love my sissy, even if he isn’t worthy of me. He is loyal, and attentive and looks so pretty in the things I buy him. I would never want anything to happen to him so I always make sure he is well cared for medically and take him regularly for check ups. But this month I am being extra diligent.
I will make sure to hold his nuts and make him cough several times a week this month instead of once a week. And we must examine his prostate extra good this month to.menshealth2
I will be wearing lots of blue to raise awareness and making sure my sissy has lots of practice checking all my friends prostates while all of them get a shot at checking his, one after the other all night long, several times this month. Just the thought makes me dip my fingers into my hot pussy! Better to be safe then sorry.. Good sissies are hard to find.

Sissy Phone Sex~She Is Such A Good Girl!

darlaMy sissy loves to drink his beer. I told him I would buy him his beer but he had to do something with the cans. He couldn’t throw the cans away. I wanted something out of the money I spent on the beer he was drinking. My pussy was twitching with anticipation to see if he would meet this challenge and earn his beer.
Last week I asked him about the cans. It has been six months and I haven’t seen one beer can in the trash, not one. He just smiled and said he was being obedient and doing as he was told and I would see soon enough what he was doing. Again my twat was all worked up at the thought of him pleasing me. He assured me I would be proud of him.
Last night after dinner he sat me down on the couch, He gave me a foot rub like none he has given me to date, making me all hot and bothered and wanting to order him around.
He asked if I would sit and wait on the couch that he had a surprise for me. He wanted to model for me and make me happy. So I obliged him and sat sipping the drink he had made just for me.
He went about lighting candles and setting the atmosphere and then he disappeared in his room.
When he came out my jaw dropped, I couldn’t believe it! This must have taken some time and he must have worked late into the night while I slept to complete this. It was astounding.
He had taken his beer cans and cut them, punched holes in them and crocheted sissya beautiful dress. My pussy was dripping with joy!
He looked so proud and very stunning in his long gown made of Budweiser cans and yarn. I have to say I was very proud of him, he served me well and did just as he was told!

Sissy phone sex with Morgan and Madison

Morgan&Madison 10Last night, my Mommy Madison and I got a call from the most unexpected kind of caller. It was a sissy that called and wanted to role play with me and Mommy Madison. So this is how the story goes … Mommy Madison and I came home from shopping and the moment we walking into the house there is a silly guy wearing our bra, panties, and Mommy’s new sexy high heels. Mommy Madison and I were shocked at what we saw and began to laugh at the silly sissy. Then Mommy started scolding sissy for dressing up in our sexy clothes but at the same time we told sissy that she looked pretty. However, Mommy Madison sad that it is spanking time and I would get to use my own paddle on this sissy. Yay for me! So we had that sissy bend over and pull down my panties that she was wearing so I can spank her booty. Then Mommy Madison went to go get her nine inch strap-on so she can pound sissy a new booty hole. I help spread open sissy’s booty cheeks so Mommy can stuff sissy. We had so much fun together punishing this naughty silly sissy for wearing our panties.

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Submissive Phone Sex Sissy

hot phonesex darla6I love having my sissy at the beach with me. I knew just what I was doing when I told him he was coming with me for the week. He was so excited, he knew he would be my slave and I knew I would keep him in the hotel room at my beck and call. Waiting on me hand and foot like a good sissy should.
Sissies are so submissive they make the perfect little cabana girls. I always have a fresh drink in my hand. She rubs oil all over my glistening naked body as I tan. She fans me when I am hot and waits on me hand and foot.
And I love the looks she gets when I decide she has been good enough to go out on the beach for a sissy break.
At night I bend her over and fuck her sissy ass pussy and release all my tensions before she gives me a body massage as I go to sleep.
I love my submissive little sissy!

International Clit Awareness Week

clitIs this a joke? Oh no my sweet little sissy. You can celebrate with us this week, while we make everyone aware of our clitoris in all it’s budding glory.
I will play with your clit this week but first you must earn it my little sissy. Come to me and get on your knees. Reach up and grab my ass, a cheek in each hand and squeeze tight as you pull my bud to your lips. Lick my clit softly, gently at first. That’s right, can you feel it getting harder and more swollen as you darla7awaken the bud? Now it is time to suck it between your lips, pull it into your mouth. Suck my clit the way you want me to suck yours later this week.
Now reach your hand down to your cock, peeking out of the top of those silky little panties you have on. That’s right, there you go, touch your self. Rub that sissy dick of yours. Keep it hard for me I want to watch you jack off while you give my clit the attention it deserves.
You will be doing a lot of jerking off this month my sissy. Because not only is this International Clit Awareness week, but May is International Masturbation Month.
Coincidence? I think not!

Pitiful Little Sissy

hot phonesex sissyMy friend let me borrow her sissy today. He was so pretty in his little white frilly tutu with his hair all done up and his makeup nice and thick and whorish. I made him look at himself in the mirror thinking his dick would get hard at the site of himself all dressed up for me. But to my dismay when he turned around I didn’t see a hard on. I made him bend over my knee and I pulled up his tutu and spanked his ass until it was red and hot to the touch for not having a hard dick and still I could not feel a hard on against my legs. By now I was very angry at him and I let him know what a sad and pitiful fucking sissy he was. He started crying and tried to tell me he did have a hard on. Thinking he was lying to me on top of everything else I began to yell and cuss at him for being such a worthless piece of shit sissy. When I made him take off his tutu and looked at him standing there with his tear stained face and that miserable little thing between his legs I could not stop laughing. His fucking dick was not even as big as a fucking chicken nugget and the damned thing was hard. I made him stay naked all day playing with that fucking little itty bitty dick of his, laughing at him all the while. I made him my bitch and he did anything and everything I told him to. I am borrowing his ass again soon because that shit is hilarious. I had planned on letting him lick my pussy while I fucked his sissy vagina, but he is to fucking pitiful to deserve my superior pussy. His new nick name is McDicky, the fucking thing looks like half of a chicken McNugget. Fucking pitiful! Couldn’t even be in a fucking brats meal….

So Obedient…

hot phonesex darla5I love when I get a new sissy to play with. I finally invited my co-worker to the house for a friendly meal. Or so he thought. After dinner I made the boy go put on his baby dolls and clean up the table and the kitchen. Every so often bending down to rub his little dick threw the silky panties that he was wearing. I could tell my new sissy had no clue how to react.
He excused himself to the bathroom and of course I was just a minute behind him. I closed the door and took the razor and shaving cream out of the medicine cabinet. I told him that I had noticed him looking at me at work and I had my eye on him as well. The dick in his hand that was peeing, got rock hard in a second. I knew I had him!
I got nice and close and whispered in his ear that I like my men clean shaved and silky smooth just like my nighties. He didn’t say a word as I rubbed shaving cream on him and began to shave every inch of him.
 When he was nice and bald I led him into my room and took out an especially cute little pink and black lace baby doll with nice little panties and instructed him to put them on. His dick had to ache by now as hard as it was!
When he turned around I started rubbing his huge cock threw the panties just like I had done earlier for the boy. As soon as I could feel him spasm and knew he was going to cum I stopped.
I led him back into the living room and made him get down on all fours for me in front of the boy. I watched as the boy got behind him and began humping his ass cheek until he came in his little girl baby doll panties like a good boy. All the while I am rubbing and fingering my wet pussy.
After praising the boy and sending him off to bed I tell my new sissy that he will do my bidding from here on out and he will dress just like this for me. Everything is going to be on my terms. I can tell that the idea more then pleases him. But it really wouldn’t matter anyway.
I lift my foot to his face and begin caressing his mouth with my toes, moving down his chest to his waiting dick.
“I want you to cum for me now. But I am not going to fuck you yet, you have to earn that, my pet. So get up and fuck my leg like a dog would. Hump me till you cum in your silky panties.”
She did very well for her first lesson…there will be another one tomorrow.