Category: Sissy phone sex

Babysitter Phone Sex Fantasy With A Submissive Daddy

He was late coming home from his date.  He has been single for a long time and he needed to get out and away from his sons and daughter.  After a long night of not giving a fuck of what they were into or up to they went to bed.  I kept looking at the clock and it just kept getting later and later.  I had had enough of doing this, I wanted to go out with my friends.  I was stuck in this house with a parental control on the cable so I couldn’t even watch anything other than cartoons.  My brain was going to bleed if he didn’t hurry the hell up.

He came in and didn’t even say he was sorry.  He handed me a whole fifteen dollars and told me to have a good night.  Are you kidding me? Fifteen dollars for six hellacious hours of babysitting? No, no, NO!  I just looked at him and told him that I wanted more than this.  He told me that he didn’t have anymore money, I told him then he better get back out there and tap an ATM or something because I was not satisfied with my pay. 

He told me that he wasn’t going back out in a very stern voice.  What? Nobody talks to me that way, EVER!  I put my stuff down and poked him in the chest and told him, “Listen, YOU are going to get the fuck back out there, and YOU are going to get me more money…NOW!”  He actually shrunk back.  He mumbled, “Yes Ma’am.”  I started to smile and let the anger fade from my face.  I said, “Did you just say yes Ma’am?”  He nodded his head and looked down at the floor.  I said, “Well, well, seems Dear Old Daddy is a submissive pussy.”

He looked like he wanted to cry, but I didn’t care.  I figured if I could not have cold hard cash, then he would have to work it off.  He owed me a lot more than what he tried to give me.  By the time I left he was dressed in some of his wife’s clothing that she left behind begging me to make him my very own Sissy Bitch.  He also had his first taste of man cunt insertion.  He wanted to cum so badly but he isn’t allowed to until he can get me the money he owes me.  I fucking HATE babysitting, but I love Babysitter phone sex, especially when it involves a fantasy like this.

Sissy phone sex with Charlie

I got a new playmate this weekend, and we had so much fun. I ran into this man while shopping and he was looking really embarrassed supposedly trying to buy some lingerie for his “wife”. Right!!! I saw the sizes he was looking at and they were OBVIOUSLY for his girly tendencies he keeps secret.

 

So, I cornered him outside the store and told him he had just won a free Sissy makeover! He was beet red and stuttering, and I loved every second. I told him we were going over to the M.A.C. counter and we were going to make him up like a sissy. Then I was going to make him drive us to a hotel across from the 24 hour gay club.

We got a sleazy hotel room and I got him to dress up and become a Sissy for me. I’m a Princess and only hang out with other Princesses so dress like slutty princess. I escorted my Sissy over to the club and hooked her up with a lot of cock. I had my sissy swallowing cum and had her sweet cherry popped.

Who’s next?

 

My Sissy phone sex slut Daddy

My daddy is completely wrapped around my finger, and is a really pathetic sissy phone sex slut. I like my sissy’s to be pathetic after all their manhood is none existent once they start wearing pink frilly undies.  It all started when I was a young sweet little thing and very mischievous. I would persuade my daddy to let me dress him up and put make-up on him. I would raid my mother’s drawers and make-up to dress daddy up with.

So you see I started shape my sissy slut early on and I love that he still lets me play dress up and make him my sissy phone sex slut. I started the really naughty play a few years ago as I was exploring sex. I wanted daddy to be a part of sexual exploration and he didn’t seem to mind. He was willing to let his little princess use him as I wished to use him. We had gone on a vacation together just the two of us when things took a new level.

While we were in the hotel room taking a nap, well I was napping anyway when he snuck out. Daddy had gone down to a sex toy store and picked up a few goodies. I awoke when I heard him coming in the room. I was half asleep and confused as he put a few shopping bags on the bed. He had also gone to Fredericks of Hollywood and got some things for both of us. I started peeking in the bags and became really excited. Smiling at my daddy asking if we were going to play dress up now. I could see he was very excited also.

Pulling out all the goodies I immediately started sliding my cotton panties off and my little t-shirt off as well. I was getting all giddy inside and found the stuff for me to dress in and what I’ll be dressing my sissy in. Then what really got me excited is the strap on cock I get to use on my sissy phone sex slut. Oh what a good little sissy phone sex slut I’m going to have!!! Look at these sweet frilly pretties I get to dress daddy up in!

We went and had a shower together before we started our dress up fun. I had my sissy phone sex slut daddy sponging my sweet little body clean. I made him suck my clitty and drink my golden nectar while in the shower. He is such a good sissy phone sex slut serving me so well, just as every daddy should.

Once out of the shower we got dried off and daddy rubbed my body oil all over me. I in turn also rubbed daddy down with some pretty scented oil. Daddy then sat on the toilet seat so I could make his sissy phone sex slut face all pretty. I love putting make up on my sissy phone sex slut daddy.

Daddy is all pretty now with his face all made up to be my sissy phone sex slut  and all we need to do now is dress her up. I loved the frilly pink teddy and matching panties for sissy phone sex slut muffin daddy. He even picked up some sexy pink thigh high fishnet stockings to go with her sweet  sissy phone sex slut outfit. Oh she’s so pretty now in all her pink and lace. Such a tasty sweet sissy phone sex slut I have.

I put on the leather bustier and black fishnet stockings with a sweet pair of black lace panties to finish it off there are a pair of black stiletto heels. And my favorite part of it all, my new shiny purple strap on cock which makes controlling my sissy phone sex slut all the more!

 

Pathetic Sissy Pet Pays for it All!

I laughed so hard when I heard about Mistress Levi blackmailing her pathetic little sissy! We have a fabulous vacation planned, and this useless little piggy is going to flip the bill — that’s what I love to see — a sissy who knows her place! Awww… poor little wimpy thing, she never thought twice about obeying her Mistress Levi. Your Mistress is going to yank you around by that nose ring while you make little piggy sounds and beg for more! All us girlies get to have fun in the sun and then giggle about the blackmail nose ring Piggy Pet every night while we drink our cocktails on the beach.

You better do eveyrthing Mistress Levi says, you little sissy, and make this our best vacation yet. No excuses. Put your little dress on, and wish you had panties as glorious as ours. Sit in the corner and face the wall, and daydream about what it would be like to be worshipping your Mistress in the sunshine. That’s something you will never get to do, Piggy Pet! You will be stuck at home, hoping Mistress Levi has some time for you, waiting and wishing…

If only you were a pretty grown up, like we are – but you can forget that. Stay where you belong little baby Piggy Pet, stay home alone and suck your fingers raw thinking about what Mistress Levi and her girlfriends are doing without you! Each evening, before you go night night, you say three times that you wish you were as amazing as her. Wish it with all your might.  You will never be, you’re destined to be a little sissy forever!

Blackmailing A Nose Ring Piggy Pet Is Fun!!

Do you know what it is almost time for? Vacation!!  Luckily for us Goddess Levi has trained her sissy piggy pet well.  That’s right, that sissy fairy is being blackmailed to pay for the whole company to go on vacation. We all know she is going to do it. She knows what will happen if she don’t.  Everyone will know her name and not just her face. The world, her family, friends and everyone at that big successful job of hers.  Instead of being branded with the letter A, she’ll wear an outfit made just for her. It will have BLACKMAIL NOSE RING PIGGY PET all over it. Might even make her wear her poo poo make up. When I say outfit made just for her, I don’t mean one of those cute fancy dresses that, that sissy fairy fag likes to wear. Nope! It’ll be something to lower her standards even more. Dress will be a mess, no pretty high heels for you!  Poor nose ring piggy pet. I bet that would make her all sad and she might even cry, just like the little crybaby sissy she is.

She is our house sissy and we love her dearly but she knows Mistress Levi is in control and she must do what she is told or she will not like the consequences. So be a good blackmail nose ring piggy pet and pay for us to go on vacation. You know Mistress Levi looks after ALL her girlies. I wouldn’t like to be on the wrong side of that situation. But then again the sissy piggy pet deserves it anyways.

Sissies on Parade!

 

 

My older sister and I returned home from shopping, and what did we find?! Her husband in some kind of outfit…dressed like a sissy!!! We were both shocked and I looked at my sister, worried about how she would react. She started laughing and said, “Well, okay, then. I guess we’ll have a fashion show!”

My sister told her husband to get out all of his sissy little clothes and lay them on the bed. We put together several ensembles while we demanded that Sissy put on some make-up. “Are you sure this is all?” my sister asked. Sissy’s head bowed and he returned with a Little Bo Peep outfit! “Oh, now we have to start with that one!” She told me to go get the camera; we were going to make a fantastic video of our fashion show. You should’ve seen Sissy’s eyes! They got so big, but I think it was partly from excitement. My sister and I also placed our own clothes on the bed; we began modeling for the camera. My sister brought a bottle of wine; and, by the second bottle, she and I were throwing off our clothes and just making Sissy parade in them.

We’d walk or crawl down our catwalk, but Sissy had to prance in his outfits. My sister plopped on the bed and spread her legs. “Fuck me, Sissy,” she growled. I moved to leave but she told me not to go and threw me a strap-on. I put the harness on and pushed the dildo against my clit…and it began vibrating. Sissy started fucking my sister and I pushed the cock to his asshole. It was already open and ready but I took my time because each time I pushed it further, the vibration became stronger. By the time that I had the entire cock buried in Sissy, I was cumming. I collapsed on Sissy and we were all lying on top of each other, a human pile. It was so much fun and I can’t wait to watch the film!

 

Not a Chance, LOSER!

Donald lives next door to me and texts me damn near every day. He always sends me pictures of his cock and tells me how bad he wants to ram it in my shit hole. UGH. He thinks he has a chance with me because I let him watch me as I masturbated once. I was so horny and got off to the idea of some creep peeking in my window. I seductively licked my lips and blew him kisses as I dug my fingers deeper and deeper inside my pussy. The only reason I did it is because I felt bad for him. I got completely sick of him texting me every day so one day I texted him back, “Cum over.;)”. I KNEW for a fact I wasn’t going to give him any nookie but why not play with this pathetic dork.

I opened my door greeting him with nothing but a tank and panties on. His pecker instantly got hard and began bulging through his pants. I laughed right in his face. What a loser! I tossed him on the bed and mounted him making sure to push my tits against his chest. He began grabbing my ass and trying to slide his fingers in my tight hole but I told him to not fucking touch me and slapped him across the face. I wanted this pathetic loser to really think he had a chance so I can let him down as harshly as possible.

I stroked his tiny penis with my hand and got really close to his ear. I nibbled on it then stuck my tongue all the way in. Next, I began to whisper, “It’s never going to happen” but as soon as I said “It’s” he screams “CUMMING” and let off a huge load in his pants. OMG how gross, right? I let him know that was the closest he would get to fucking this pretty Princess and to stop fucking texting me. I told him how much of a fucking loser he was for making such a mess in his pants. No wonder he never got any pussy.  Even though I was degrading him, for some reason he had this stupid grin on his face the whole time. I called myself setting him up for failure and showed him that hot piece of ass like this doesn’t fuck with losers like him. However, the grin on Donald’s face told me he had won a small personal victory that evening.

 

It’s so Hot to be a Princess

Not only is it hot to hear someone call me Princess, it’s also hot to know that they are correct.  I am the mother fucking Princess!  Being a Princess such as myself comes with a lot of perks.  I get a lot and I do mean a LOT of pretty sparkly things sent to me!  How fucking great is that?  Especially from my sissy dolls.  Most of them want me to make them just like me!  Which I am happy to do because I am perfect, and helping them to try to achieve the level of perfection that I have makes it a good deed and makes me happy. It gives me Jesus points, and who the hell doesn’t need some Jesus points?

One thing that all Princesses need is a type of Tiara!  The more girlie the better.  So many of my sissies have Tiara’s.  They wear them for me when I watch them on cam.  Some of them go all out, and have their full gear on for me, which by the way I just LOVE!  They prance and prim for me.  We work on so many things together.  Like how to do their hair, how to dress, how to do their make up, how to make it look like they have some sissy tits.  You name it, we do it.  One of the things they have a hard time with is walking in something with a heel.  No lie, every one does. The first time I wore five inch heels I almost fell over every time I tried to take a step, but then I found out there is a secret for walking in high heels.  I share that secret with my sisses!  They are amazed by what an immediate difference it makes for them. Next, are the shoes.

When they learn how to walk in very very high heels then I have them save their pennies so that they can get a wonderful pair of blinged out Princess shoes.  All Princesses need sparkling heels to make them a true Princess!  They are always so excited to show me what they bought, and I am thrilled to see the shoes.  I love shoes, and I am absolutely flabbergasted by people who do not.  I guess it’s a Princess thing.

Fem Friends

Peyton called and said she had a special friend that wanted to come over with her. I love it when she wants to come play with the girls and I because she is such a good sissy training slut and her feminine male friends are so much fun to play dress up with. She showed up early in the afternoon right after the girls got home from school. Her friend was so shy staring at our girlie clothes with a look of envy in his eyes. I told Peyton to take him to my room and feel free to let him wear anything in my closet and drawers. The girls and I took off our clothes down to our matching silky underwear and got ready for our play date. They know what Peyton’s friends like and they love playing with them. When they finally emerged from my room, her friend looked stunning and the transformation in her attitude was like night and day. It always amazes the girls and I how different Peyton’s friends are when they come over as boys, shy and introverted, but when they put on silky sexy girl clothes with makeup and heels and are free to be who they long to be, they are completely different people, happy and carefree and not shy or introverted in any way, They are finally comfortable and themselves. He was now a she and she joined us with a big grin on her face, Peyton had done her make up to perfection. Wearing a pretty pink little teddy of mine with a guarder belt and thigh high hose, she was simply beaming! We had a wonderful afternoon and we all played with her clitty and mangina (as she calls it). By the time they were ready to leave, the girls and I were very fond of her, so much so that I even told her she could keep the clothes she borrowed and told her to come back anytime, with or with out Peyton.

Did You Say Bidding?

 

Today at the college library I ran into the hottest older man ever. Soon after I told him that I wanted to taste him we headed to a hotel. I gave him such an hot nasty fuck session that he offered to do my bidding as long as I would allow him a weekly fuck and suck. His first task was to put up flyers for a sports party he would give at his house, his expense. No girls are allowed except me of course. The guys showed up in groups and my man was a perfect host but he was in for a shock. During halftime I put him on his knees, naked in the center of the table like a ham on a platter. I announced the new half time event. Within less than a minute the poor guy had cocks inside every opening on his body. Hard rods were choking him, stretching his ass, smacking his face, just fucking dicks everywhere. That older guy swallowed so much cum his tummy hurt. His ass was bleeding and leaking mass amounts of sticky man juice. I sent him to make our drinks without a shower. He will be a walking cum magnet for the rest of the night. Best party ever!!!!