Category: Sissy phone sex

Another Day On The Job

cougar phonesex darlaHave you ever wondered what I am doing on my end of the phone when you call? I know you have a raging hard on. Your dick is in your hand and you have been browsing my pictures building up your fantasy to share with me. Longing for the money shot. Needing to shoot that hot load and feel the relief and satisfaction.
Well it is much the same on this end. I make sure that I am dressed in a hot and sexy out fit as I sit in my office at my desk. My pussy longing for a new fantasy. The phone rings and my nipples stand at attention straining as I fantasize about your mouth, wet and warm sucking and nibbling them till they can’t get any harder.
With each new hot and sexy voice I touch my pussy lips and rub my clit until it is swollen and sensitive.
With each new fantasy I pump my pussy hard and fast waiting and wanting to cum with you, enjoying my release and yours.
Every so often I call in my sissy and she will lick me clean so that the next load is fresh and flowing.
I love closing my eyes and imagining you there, looking at my pictures naked or in a soft sexy pair of panties stroking that cock f or me and sharing your fantasies.
So there you have it, another day on the job.

Sisssy Phone Sex Birthday!!!!

cougar phonesex darlaIt’s my Sissy’s Birthday! She has been with me for almost a year now and she not only takes excellent care of me, but she is training my boy to be a sissy better then I ever could. I wanted to show her my appreciation and do something special for her for her birthday.
I had it all planned out, a party with her friends. Lots of food and fun. I was already figuring things out in my head. But when i asked her what she wanted for her birthday (thinking she would give me a gift idea) she asked if she could have anything she wanted, with in reason. When I said yes she surprised me.
She said she always fantasized about being gang banged by 8 big, strong, strapping guys. She dreams of me watching and getting all hot and horny while she gets banged one after the other only to have it all end with me humiliating her in front of them all and banishing her to her room fr the evening.
I have to admit that her fantasy makes me hot as hell. She doesn’t want a cake or party or anything else only her fantasy.
So after much arranging and a week solid of interviewing possible participants. Tonight is the night it all comes together. At exactly eight they will begin to arrive and she will be finishing up her make up and out fit.
At 8:30 I will present her to them and I will take my place to watch the show.
I can’t wait to see what she will wear, I can’t wait to watch them take her and I can’t wait to humiliate her and send her off to her room in shame.
Happy Birthday Sissy!

Kinky Phonesex To Remember

kinky phonesex darlaI can’t stop thinking about my kinky adventure yesterday. I have done some pretty kinky shit in my time but yesterday took the cake and I can’t keep my hands off my pussy. Every time I think about it I cum again.
I was driving down a long country road on my way home when I saw her. She was tall and blonde and walking with a back pack out here in the middle of no where. As I passed her I fully expected her to put out her thumb and try to hitch a ride, it was miles before any sign of civilization. But she didn’t.
As I passed her and glanced in the rear view mirror I was struck by her beauty, she was fucking HOT. I had to pull over.
I got out and asked her if she would like a ride. She hesitated at first but accepted finally.
At first she was very quiet but as she opened up she told me that she was headed to the bus station but her bus wasn’t scheduled till tomorrow. She had spent all her money on the ticket and would be sleeping at the bus station till her bus came in.
I offered for her to spend the night in my guest room. I figured I could sneak in her room and get a peek of that hot fucking body of hers. I told her she could eat dinner with us. Explaining to her that it was my son and my sissy and I and there was plenty of room.
When I mentioned my sissy her facial expression changed and I couldn’t tell if she was offended or intrigued but she took me up on my offer any way.
After dinner my sissy cleaned up and as always served us after dinner drinks and began my nightly pampering massage as we sipped our drinks and relaxed.
As the drinks flowed I told my sissy to take care of our house guest as well and he began massaging her as well.
One thing lead to another and the more we drank and the more relaxed we got she confessed that she was leaving town because some one had found out her secret and in a small town she couldn’t take the chance of other s finding out.
I never in a million years imagined what came next. She stood up, dropped her dress and showed us that she was a hermaphrodite. she was born with both a dick and a pussy and was the perfect specimen standing there naked before me.
I fucked her last night while my sissy watched. I then let him pleasure her with his mouth and hands while I watched. I fucked her deep into the night while my sissy waited to clean us up and bring us refreshments in between fuck sessions.
I was sad to see her go this morning but last night was a night I will never forget!

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!