Category: Sissy phone sex

Holiday Fun With Mommies

Since my Mommy left me when I was very young and it is Christmas time, I decided to hang out with a few Mommies that I have gotten to know really well. Hanging out with Lauren, Darla, and Devon have been such a blast with the whole Mother / Daughter bonding experience. Despite how they are all so different from each other,  they all love to take me into their family to share some kinky family fun time.

When I met Mommy Lauren, she taught me a thing or two about how she makes her money. She is a sexy stripper that loves to take off her close and touch herself in front of a whole room of horny Daddies. One night she even brought me and her baby girl to the strip club where she worked at. I was so excited how she included me into her stripping act on the stage, along with her young daughter. My cunny got so wet while she stripped away my tiny, panty while her baby girl was shaking her booty on stage.

Mommy Darla has so much fun with her sissy boy son. While I spent time with them, we had a huge fashion show / dress up day in her living room. Mommy Darla and I would be the judges while her cute, sissy son dressed up in whatever we wanted her to wear. She and I giggled at the pretty lil’ dress her sissy son would model for us. She made me so happy when she kept kissing and touching me while telling me how she wants me to model for her. 

There was something about the way Mommy Devon that got me acting so dirty in such a very naughty way when I am around her. She was a blast to play with in all of her trashy, Mommy ways. Meanwhile, her two pervy little ones would take right after her and start kissing, licking, and even sticking me. It felt so good that I could not stop squirting all over the place. She knows no boundaries of family fun time when it would get nasty. 

So I thought I would show them all how much fun I had with them by inviting them over to my house. I know my Daddy would love to play with me and my new Mommies. Oh boy! I just can’t wait til they come over and try out my Daddy’s North Pole in all of their Mommy cream, holes. Who needs a real Mommy when I can play with three naughty, Mommies instead. Merry Christmas and Happy New Year!

Sissy Blackmail

Blackmail phone sexSissy phone sex is fun for me because the sissy that calls me wants to play with Peyton too.  Peyton is a good sport about it, she is a little Princess, so she knows exactly how to handle miserable worthless fucks like him.  He wants to smell her panties and make panty soup and what not, but she has yet to give him anything.  She blackmails him into sending her money, but she hasn’t given him any panties, socks, nothing!  I am so proud of her!  Peyton is definitely turning into the perfect young lady, and she surely understands what men are willing to do for her

Peyton walked up to our sissy and let him smell her knee, then she told him she was going to tell his secretary that he gets into her gym bag when it’s left behind and he licks and smells all her clothes.  She pulled her pants down and stuck her ass in his face, but moved before he could lick her.  Peyton walked over to the couch, sat down and played with her tight little pussy while he stared at her.  She stuck her fingers in his mouth so he could taste her pretty young pussy juices.  Peyton has mastered the skill of sissy training with a small side of blackmail.  I am such a proud Auntie, even though she has a lot to learn, Peyton the little Princess is certainly off to a good start.

Our pretty little Princess Peyton can be found on our sister site YoungOnesPhoneSex.

Going To Relax And Shop

cougar phonesex darla4This week is so hectic. Even with Sissy doing all the shopping and preparing for the holiday dinner I am a nervous wreck. I am always freaking out over if the holiday diner will go well and then if I can get up early enough on black friday to make the mad rush and get the shopping done, Which isn’t easy even with my wonderful Sissy..
And then I came up with a brilliant plan! In fact the whole thing is making me creamy wet. This year is going to be a breeze.
So i went out and bought Sissy this cute little out fir with bunny ears and me this nice comfy chase lounge chair.
Fuck black friday, and Sat and Sunday I am relaxing.
Cyber Monday (a wonderful invention) I am going to put sissy in her pretty new outfit, sit back in my chair and masturbate all day, while Sissy orders all the gifts on the computer on Cyber Monday. I am going to call it Darla’s Kinky Cyber Monday.
And there you go no fuss no muss, just cum and relaxing and Sissy dressed so pretty typing away on the computer taking care of it all!

Peyton’s Lesson # 2

2 girl call phone phonePeyton and I had the pleasure of torturing our sissy again last weekend.  He wants to lick her panties and suck her ass, and he even begs to buy her panties to make himself panty soup.  The first time we played with him Peyton did very well controlling him, and staying just out of reach so he would offer more and more money for her panties and bra.  The second time was perfection!  Peyton did a fantastic job of making sure this sissy faggot did as he was told and she tortured him with her pretty little pussy and ass.  She even let him lick a nipple just to drive him out of his mind.  By the time we were done working him over he was to bring her $300 for her panties and he was going to beg her for her dirty gym sock and yoga outfit.  Peyton said she would let him have it after she worked out, and I think her generosity of offering to work out for an extra fifteen minutes was very sweet of her.  I’m sure Peyton will grow from the Bratty Princess she is now to the perfect Bitch In Charge Mistress!  You can find Peyton on our sister site YoungOnesPhoneSex

Girls, Girls, Girls….

 

hot phonesex darla1The boy and the sissy decided they wanted a little vacation alone. We talked about it for almost a month. I was very hot phonesex darla2resistant, not because I don’t trust sissy, I trust her with my life.But who would clean for me? Who would take care of me? Who would draw my bath for me and get me midnight snacks and give me foot rubs and brush my hair and go shopping and clean house?
And what would I do in an empty house with no boy wondering around in his pretty dresses twirling and modeling and playing tea party with me.? I mean it would be such a drag to be here just me and no sissy and no boy. I hot phonesex darla3don’t even have a fucking gold fish.
I know I sound like a whiny ass spoiled bitch. But I am spoiled and I love it.
A bunch of the girls and I got together and went to a strip club last Friday and as we were talking about it and how depressing it would be for me but how much fun they would have, they saw my dilemma.
How could I tell them no and ruin their fun just because I would be lonely.
As the night wore on and the drinks flowed more freely we came up with what seemed like a great solution.
Let the sissy and the boy go for their vacation and we girls would get together for a week long slumber party with all the trimmings. Sexy lingerie, pizza and beer, champagne and caviar, some male strippers, lots of sex toys, porn, what ever we could get our hands on that would be deviant , naughty and fun!hot phonesex darla4

Sissy Phone Sex

Sissy Phone SexSissy Phone Sex is aways so much fun, but I have a sissy that is particularly fun for me.  He likes to call and be sweet and have me dress him up in panties and dance with me.  He knows I am not a Mistress, Goddess, Princess, or even a Brat, so the fact that he calls me is very cool.  We put on nice pretty sexy panties and dance around, but mostly he wiggles.  Now I am not sure I understand how that feels, or why he likes it but its so funny to listen to him giggle when he does it.  I actually had a sleep over with some friends and he called while they were here, so I had a sexy pajama panty party!  It was the funniest, silliest, greatest thing I’ve done in such a long time.  I can’t wait for him to call back so we can have another great session of sissy phone sex!  Wiggling has never been so much fun!

Sissy Tabatha And her Sex Toys

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Oh Sissy Tabitha loves her Princess Mommy Darla. She is such fun to play with and all her sex toys are especially designed for her humiliation and pleasure just like she deserves. Last night we did an ice cold enema that gave her cramps just like her period would. And she loves her big silver hook to be inserted into her cunnie and hooked to her collar making her helpless and at the mercy of her Princess Mommy. She loves it when I make her put marshmallows in her condom before she covers her clitty so that her warm squirty squirts melt them and make her clitty all ooey and gooey. Her butt plug in her cunnie while she sits on a bench and brushes her pretty long pony tails, reciting my little phrase over and over again, “I am Princess Mommies Sissy. I will serve only my Princess Mommy. I deserve my punishment and will be her good and devoted sissy from this day forward” What a pretty and good Sissy my Tabitha is. I love playing with her and all her toys as much as she loves me using them on her.

Surf’s Up

mommy phonesex darla1Have you ever thought of what it would be like to fuck in the tunnel of a wave on a surf board? I woke up this morning from that very dream. All though it is likely an impossible feat, it made my pussy very wet and the dream was very realistic. I woke up wanting nothing more then a nice hard cock in my soaking wet pussy. Maybe when the weather gets warmer I will invest in a surf board and learn to ride the waves. Who knows I might meet a hot young surfer dude that will fuck my brains out on the beach while the waves crash in all around us and pound our bodies while he is pounding my pussy like a man who can’t get enough of the sweet softness deep in the folds of the lips that are in between my legs. We can make our own tunnel in the waves with the slick, cold surf board under us. The feel of it caressing my ass cheeks as the salt water covers me and his cum fills me up on the shore with my son watching and my sissy waiting to clean me up and take me home. Sounds like a dream come true to me.

Wanna Be My Boy Toy????

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I love having my sissy and watching her all day long in her beautiful dresses and makeup. I love buying her silky panties and girlie things and I love the way she takes care of me and trains the boy. But every now and then I get to thinking that I would like to be some ones girlfriend. I don’t know if I would stay with it for a long time, but it might be cool for a while. Just to know there is some one there for me.Someone to wine me and dine me and treat me special besides my sissy.
Oh who the hell am I kidding I could never be a girlfriend things are fine just the way they are. I love sissies to much and the joy I get from being the dominant one in the house with my submissive and loving sissy taking care of me. can always get dick I don’t need to be a girlfriend…unless of course the right one comes along. Oh who knows.

El Dia De Los Muertos

darlaOctober is the month for Halloween, but November 1st is the day of the dead. I love the celebration and all the vibrant colors. This is the celebration of lost loved ones and a day to bring their spirits back. Everything is bright and colorful from the skulls to the alters offering sacrifices to the deceased to the dress. Even the belief that the souls of the departed fly back on the wings of the colorful butterflies that fill the streets is intriguing. It is a lively and spirited holiday that makes me horny, happy and hot. I decided to teach the boy about the holiday and he is so excited. We have been fucking machines since we started talking about it and learning about it. There is something so mysterious and electric about the whole thing that it has us all ready to fuck the month away, including sissy. If you haven’t experienced the electric thrill of this fascinating holiday, you need to look into it and get on the fucking band wagon with us. I hope we don’t fuck each other to death before the day comes and we can celebrate full out!skull