Category: Sissy phone sex

Hot Teen Slut Summer Can Make You a Pretty Sissy Too

Do you like hot teen sluts? You are not alone. I’m a nursing student and it appears that just about every doctor at the hospital I do my internship at loves a hot teen slut too. In particular, this hot teen slut! I have several doctors who spoil me with attention. They buy me expensive gifts, wine and dine me, provide me with top end pharmaceutical party supplies, even take me on nice weekend getaways. I recently acquired a new fan. But, he is not my typical admirer. He is what you would call a sissy boy.  I mean a grown ass man wearing frilly dresses, talking like a girl, wanting to play with dolls and shit. BIG OLD FUCKING FAG.

I knew he didn’t want to fuck me. Any so called guy wearing panties, doesn’t have anything to satisfy me with. I was wrong. He has a big fat wallet. He is giving me tributes for my time. As he should; if you want my attention on the phone or in person, and you are a sissy, you simply have to pay me in cash or gifts to make me deal with your pathetic loser ass. This doctor has a double life. Brilliant surgeon by day, total sissy fairy fag by night. Wants me to teach him how to be a hot teen slut. Challenge accepted. Money in my purse pocketed. I’m going to have so much fun not only humiliating Dr. Sissy, but dressing her up. Our first session together I transformed her into amprissy sissy nurse. Look how pretty and pathetic she is? Feel free to laugh. All my patients are going too!

Are you a sissy or a sissy wannabe? I can turn you into a hot teen slut too! I think I did an awesome job with Prissy Sissy Nurse Sophia. What do you think?

Sissy Phone Sex with Samantha and Jillian: My First Sissy Encounter

My oldest grandson has a crush on his occasional babysitter, my step niece Jillian. She is a cutie. I caught him one day smelling and jacking off with her dirty pantyhose. It was actually quite a turn on, but I worried he may be a sissy. I decided to talk with Jillian about it. She assured me it was quite normal for boys his age to like a girl’s panties or pantyhose. She said all the boys she babysits for steal her pretty soiled undergarments. They do it to smell her sweet teen pussy. She then invited me to go shopping with her and her special friend. She said she wanted me to meet her friend, so I could rest assured that my grandson was no sissy.

 Jillian told me she met this rather special girl at the mall months ago. Apparently they were both shopping for frilly underwear and pantyhose and exchanged numbers. Jillian said she was a total sissy fairy fag and once I met her I would have no doubt that my grandson was just a normal hot blooded horny teen boy. I met them at the mall and Jillian introduced me to her Sissy Fairy Fag.  I was stunned. I could not help but burst out laughing. She was in a precious baby doll dress, wearing jingly jangly jewelry, and pumps and makeup. She was even in a diaper with one of those plastic protectors on the outside. Now this was clearly a sissy. When she spoke she was quite poised and articulate, which surprised me.

Sissy Fairy Fag wanted to impress me with her babysitting skills in case I ever needed help with my grand angels.  She informed me she has been taking care of her dollies for some time now and felt it was time to be in charge of live dollies. We were in a baby store shopping for some pacifiers and toys for her when she put her Hello Kitty doll on the changing table and demonstrated how to change a poopy diaper and feed a little one. I knew my grand girls would love her. She was a life size doll. A big old pathetic sweet sissy fairy fag.  They could dress her up, put make up on her, do her nails, style her hair, sing songs together, play Candy Land, laugh at her… I felt good confident about Sissy Fairy Fag’s ability to take care of my angels. She was sort of a faggy Mary Poppins. LOL.

Thanks to Jillian, I know understood what a real fairy is all about. My grandson was far more of a man than Sissy Fairy Fag could ever hope to be, despite the age difference. My grandson likes to masturbate his cock with Jillian’s panties and pantyhose, not wear them and prance around the house playing with his little pee pee singling pansy ass tunes. In fact my grandson at his young age has a bigger pecker than Sissy Fairy Fag. She pulled her panties right down in the store to show us what a tiny little clitty she has too. I am still laughing. I’m in awe though of how someone so pathetic could be so comfortable in her skin. She had a great sissy trainer. Jillian told me, Mistress Levi made Sissy Fairy Fag who she is today. Well kudos to her. But I am keeping that hot bitch away from my sons and grandsons! I want real men in household.

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.