Tag: sissy phone sex

Sissy Princess Training

Sissy Princess Alert!!  It always makes me smile when a Sissy phones me to let me know how pretty I am, and how they want to be just like me.  I have had that happen more than a few times.  Because of that, I am going to start offering Sissy Princess Training Sessions.  These session are for the truly Girlie-Girl Sissy.  I will teach you how to properly wear perfume, which perfume to use, how to take care of your nails, how to take care of your clothing, how to take care of your hair, how to do your hair, how to wear make up, and the proper way to apply it.  The most fun though, will come when we shop together!  We can look at all the pretty frilly things online, and I will choose something for you to buy.  Of course there will also be “girl talk” about men, how to masturbate like a girl, how to suck a cock (but only for those who are interested in such things, not all Sissies want to have a dick in their mouth).  Usually I am very much the mean girl, but if you know you are a Sissy, then why should I not help you to be the best Sissy you can be?  Also, if you would like, there can be assignments given to you that you would have to complete. This involves you sending me pictures to my email so that I can see the progress, or to make sure you have actually done the assignment.  OMGOSH I am so excited!  This world needs more Princesses, and especially Sissy Princesses. xoxoxo

Sissy Phone Sex

Peyton is turning out to be a beautiful young lady!  Over the years she has learned the fine art of tease & denial, and I couldn’t be more impressed with her.  Princess Peyton has listened and understood that the way to a man’s heart is through his cock.  I know the way used to be through his stomach and what not, but I know that’s not the case.  Peyton was over visiting when this panty waste asshole Adam came over, and all Adam wanted to do was get in Princess Peyton’s pants.  She noticed right away and used it to her full advantage.  She shook her ass, bent over in front of him, and sometimes she even walked a little too close and rubbed up against him.  His cock was throbbing and pressing against his jeans so bad that he was visibly uncomfortable.  Adam tried to grab Peyton, but she quickly moved out of his path and told him that if he ever hoped to even touch her arm then he was going to have to provide much more to her than some lame ass cock that is hard.

Sissy Cocksucking Cheer Squad

He was so excited to be invited to Jasmin’s house for a Homecoming Party after the Football Game.  I honestly do not think he had ever been invited to anyone’s party, especially not a Rah-rah and Jock party.  Four of us; dressed in our cheer uniforms; walked up to him while he was standing at the locker and gave him the invite.  At first he didn’t take it because he thought we were joking around with him.  I told him that his name is on the invite but if he didn’t want it we could just switch out the name on the invite.  He snatched it out of Madyson’s hand, he even smelled it; eww. lol

As we walked away, I looked back at him, he was watching us walk down the hallway back to our group of popular friends.  Just to be ‘sweet’ I blew him a kiss, he didn’t know what to do, so he just blushed.  We were laughing so hard.

We had him sit down on the sidelines with us as we cheered for our football team.  All of us took turns sitting with him, explaining the moves, or just chit chatting about classes.  By the end of the game he was completely relaxed.  He even was invited into the locker room with the guys so that they could all leave together to get to the party at the same time.  Us girls left before hand to make sure everything was set up.  Two hours later the doorbell rang, the guys came in, along with him.  The look on his face as he saw us all standing there, in our panties and bras, pom-poms on our hips, ready to cheer.  The guys pushed him to the front, he was laughing, and smiling…that is, until we started our cheer.

The little shit actually started to cry!  He went to leave, but trying to get through a wall of linebackers just doesn’t work that well.  He was pushed to his knees, as one by one, all those yummy football player cocks came out.  He really did put up a fight, but it was like an ant trying to take on The HULK.  He took those cocks, sucked each and every one, swallowed load after load, there was no mercy given. By the end of the night, he was completely humiliated.  We pushed him out the door with cum still sticking to his tongue.  I wonder what he did when he finally got home, and had to look his parents in the eye.  What he said when they asked him how the party was.  The number one thing I wonder though, is if he fell onto his bed and jacked off thinking back to what had been done.  Judging from how hard he looked in a pair of Madyson’s panties that we made him wear, I am pretty sure that is exactly what he did.

 

 

 

 

 

                 

 

Playtime With My Fagtoy Professor

My fagtoy professor has been looking at me funny every day since school has started, and I couldn’t figure out why.  I realized he is a sissy slut fagtoy who needs to be shown how to embrace his kink so he can suck cock like he wants to, no like he needs to!  I knew exactly how I was going to help him.  I asked him to tutor me because was struggling, and when he agreed I handed him a piece of paper and told him to meet me there tonight at 7:00pm and our tutoring would begin.  He stood there shocked because he knew my tone immediately changed.  When he showed up at the coffee shop I led him to the back room and sat him in a chair.  I locked the door and removed the picture from the wall.  He looked shocked but I could tell he knew exactly what was happening.  I told him he was going to suck and fuck every cock that came through that glory hole like the fagtoy he is, or I was going to beat him with my flogger.  My fagtoy tried to resist, but almost immediately changed his mind and he had the time of his life sucking and fucking all those cocks for 2 hours.  When he was done he begged me to keep being his Mistress because he needs to be humiliated and forced to be the fagtoy he loves being.  I think we will have a ton of fun together.

Little Dicks…

I love begin fucked by a big huge cock, but playing with a little dicky dude is fun too.  I obviously don’t let them fuck me, but I do let them cum eventually.  We will go to the mall and the little dicky boy will buy me anything I want, and he will get himself a nice little sissy outfit.  All my sissies have to wear little skirts, tube or tank tops with tights lace panties and sexy shoes.  I usually prefer crotch less tights so it’s easier to get to the ass or should I say little bitch boi pussy that needs a cock shoved inside of it.  I have a 9 inch strap on that I use if I don’t have a real cock available to fuck my bitch pussy boi’s ass.  I prefer to have a real cock around, but when I get to use the strap on I get excited and make my little bitch suck it and deep throat that hard plastic strap on cock!  I haven’t had anyone say no to me yet so they must all like it!

My Chin Strap Dildo

Chinstrap dildos are so much fun to play with, when I find a guy whose cock is less than 4 inches long I bring this out.  I know it’s going to be fun for me because his little tiny dicky is going to be wrapped up in a rubber band because cock cages aren’t that small and he would fall out of it.  I will knot up his little dick that’s really more of a clit, yes we will call it his clitty in a rubber band then I will strap the chinstrap dildo to his face in such a way that as I am using him he can’t touch me with his tongue.  I can’t let anyone with a cock that small taste my delicious pussy, so once its in place I rub my clit all over the tip of the dildo to get it wet.  I lower myself onto the dildo ad I finger my clit and get more and more excited with each thrust.  Before you know it I am bucking up and down fucking and using his pathetic face while his little clitty is trying to break free from the rubber band.  I reach over and slap his clitty so hard that it breaks free from the rubber band and cum oozes out of his little hole and he begins to cry.  He just had his first ruined orgasm!  It was so amazing I think I will have to do it again.

Sissy’s First play date!

My little friend Justin needed some help coming out of the closet. Everyone seemed to know he was gay but Justin! So we got together and got him toasted! I mean we got him so drunk he could barely stand. We dressed him up like the little sissy slut he is. Got out the camera and let him strut his stuff in front of me. And that was it! A sissy was born! Justin just shined for all of us. He danced and sang and pretended to be the woman he really is! It was so easy to Justin to take her fist cock. We barely had to offer it at all. Our little faggot dropped to his knees and  took that cock and downed the entire things like a pro! And I got the whole thing on tape… I cant wait till our new sissy watches it tomorrow. I am sure she will do anything we want to make sure that video isn’t shown! LOL. Tomorrow she becomes a real woman. Because I want to see that faggot get fucked and beg for more! Everyone knows she will.

Honey is the Key

Henry came over again today. But this time I decided he needed to learn how to be a good slut before I fucked him. I had him dress in a pretty pink ruffled dress. And black stockings with some shiny fuck me pumps. I told Henry to get on his knees and get ready to learn to be a good cock sucker. At first he just gagged and sputtered. I cant have a cock sucking cum whore if he cant suck cock. I had to get a little tricky. I got a bottle of honey and poured it over my strap on. Then I told him he didn’t get fucked till he sucked off every drop. Honey is so hard to suck off. Henry had to really suck hard. That honey was the trick to training my cock sucking cum sponge on how to be a good little whore. After he sucked every drop off I turned him around and fucked his tight little ass like the whore he was proving to be.

Getting dressed for the first time.

After I had so much fun at my party yesterday I thought I would take the day off. But I was pleasantly surprised when Henry showed up at my door. His little virgin ass loved the way I fucked him. I figured he would be looking me up but I thought it would be a few days. The way he was standing there.. so timid and weak. He couldn’t even make eye contact. It turned me on so much I was ready to go! I told him to come inside and take his clothes off. When he had them off I threw one of my pretty dresses at him and told him to put it on. I found my favorite pair of fuck my pumps and tossed them to Henry. I could tell he wanted to tell me no. But I didn’t give him the chance. I got right in his face and told him to take his damn clothes off and put on his slut clothes! I was ready to fuck my new slut and he had to get ready for me. It turned me on so much seeing him tremble as he was trying to slip into that dress. When he slipped those fuck my pumps on I couldn’t wait any longer. I pushed him over my bed, making sure he could see himself in the long mirror. And started to fuck his ass so good. I made him beg me to fuck him harder. And I didn’t stop till we both came so good. He is going to be such a good slut for me

Wild West Party

I got to use my new strap on today. I went to a wild west party. Most girls were riding their boy toys like stallions. Bouncing up and down on the big stallion dicks. I love watching all the fun. But for me. I wanted more. I had to look hard until I found my cowboy. He was sitting on the couch watching all the girls getting fucked so good. I could tell how turned on he was. I was wearing my new strap on. So I walked straight up to him and told him to get on his knees. I was ready to mount my stallion. I could tell he almost came on himself looking at me. He did exactly what I told him. Dropped straight to his knees And let me shove my big dick right in him. I rode my stallion hard and fast. By the time I was done I had a line of young stallions waiting for me to break them in. And I fucked each and every one of those ponies.