Category: Sissy humiliation

Small dick humiliation with Felecia

He came to me with a deep dark secret that he had never told anyone. It would ruin his entire world. His family would dis own him, his brats would hate him. His wife would leave him if she ever found out. He made it seem like it was going to be shocking. I was disappointed when he told me his big deep dark secret. He liked to stick his finger up his ass while he fucked his wife. That’s it, and it was pathetic. It’s been a rough week for me, so when he made a big deal about having to have an emergency session about his dirty dark secret, then it turns out to be nothing. I was beyond aggravated. I dug my nails into the leather of my arm chair as he went on and on about this worthless secret. I told him to shut up. His eyes got wide, no one has ever talked to him like that! He went to open his mouth and I threw my note pad at him. “Shut up, I am getting a headache listening to this pathetic bull crap. Stand up right now. Grab that not pad and read it out loud to me.” He stood and cleared his throat. “I am a pathetic loser. My cock is tiny and that is why I need to bully everyone around. My wife hates me and fucks other men while I am away. I am too much of a loser to do anything about it. “When the tears started to flow down his cheeks I told him to get undressed. I made him get down on all 4’s and tied his tiny cock and balls up. I went behind my desk and told him to start reading it again. He was ugly crying now, saying how pathetic he was over and over. I slammed my big fake cock inside of his ass, making him moan like a little slut. I knew this is really what he wanted. He wanted to be humiliated. He wanted to talk about his finger play, but I knew he wanted more than just his finger up his ass! I gave him every inch!

Small dick humiliation

Tease your little sissy cock

I am so sick of dumb cocks. Its not rocket science and fucking in space. Really, If you have a penis and do not know how to use, please do me a favor and come to me for a sissy training session. If you have a small dick, cum to quickly, fuck like shit or just cannot hack it like a man, I am the solution to your inefficiency. I realized I have so many clients that really should have been born with pussies because they just cannot hack it in the world of cocks. I train my little bitches to bow, bend over, humiliate and beg for my favor because I am the master. The master at making them my sweet tittySissy humiliation Clarissa sissy maids, naughty sissy bitches and little cunt lickers for my satisfaction. I can make even the manliest wannabe man my little cunt whore and he will like it. I am so proud of them. Good little bitch, good.

Sissy Humiliation with the Biggest Sissy of Them All

sissy humiliationI love sissy humiliation calls. We have a site sissy that belongs to our bitch in charge, Levi, however we all get to poke fun of her too. What kind of a sissy are you if you can’t handle some ribbing, right? Sissies are here for our amusement and humiliation. As a mature sexy woman, I get my share of sissies, but Sissy Michael really takes the cake in the world of sissies. She is a teenie weenie sissy. In fact, Sissy Michael has such a small dick, it belongs in panties. Mistress Levi has had to put her little weenie under lock and key before too. It is just a nub! Don’t feel sorry for this sissy, however. She loves public humiliation, especially small dick humiliation. She loves to have her clit stick teased.

small dick humiliationJust take a good long look at these shameful pictures? I know what you are thinking. What self respecting man would be seen dressed up all frilly like a tinker bell transvestite? The answer to that is no man, just Sissy Michael. Let me share a shameful secret with you. This sissy is not just a sissy. She is a poopy panty princess too. Under all the pretty white lace lies a dirty secret. A really dirty secret. She is pooping her pretty little panties  underneath that pretty dress. Sissy Michael is such a loser. No make that LOSER. And, not only is she a  poopie pansy, she is a little fudge packer too.  She has an ass fetish and prances around public places like the mall begging for her sissy fannie to be stuffed. Can you imagine being at the mall and running into this crossdressing pansy begging to get a fanny stuffing? I laugh till I am crying every time I think of her being so pathetic! Mistress Levi has her work cut out for her.

Please stop by Sissy Michael’s page so you can see for yourself the most pathetic sissy in all the Internet.

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Sissy humiliation !

sissy humiliation

Ready! Okay! Give me a “S”, give me a “I”, give me an “SS”, give me a “Y”! What does that spell! SISSY! Look at this cute teenie weenie sissy of ours! Isn’t she just the cutest cheerleader you have ever seen. See this is our little cross dressing pansy who dresses to impress and heads all over town.

This prissy little sissy has tons of little secrets, well they are not really secrets. I am so sorry, I couldn’t stop giggling as I type this! Well, you see she is a big girl so I am just going to come out and say it!

She is such a fruity fag. She has the most pathetically cute teenie weenie you could ever gaze your eyes upon- along with itty bitty little marbles that fill up with clitty juice! I mean come on, how could you not tell- look at that short skirt!

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Who wears short skirts? She wears short skirts! Anywho, this sissy pansy cross dressing tooty fruity piggy is the most worthless of all worthless sissy girls out there in the earth. I mean with a clitty like that, who wouldn’t feel like a walking doormat.

Do not even get me started on that back door wittle pussy hole. No worries, this frazzle dazzle sissy girl gets it worked open very often! I just can not help but to tease her, letting her know how good she looks walking around embarrassingly in a cheer outfit.

I can not wait to see her bend down in that little skirt so I can giggle when her frilly little panty’s pop out! When she leaps in the air for joy and her itty bitty clitty dangles in the wind, I wont stop myself from pointing and giggling at it. She is just so pathetic, I can not help but to be captivated by her.

She knows how to werk it! Don’t you, you little panty wearing prissy pansy sissy!?

From Not to Hot, my Sissy project…

I have this awesome little sissy la la that I took on as a charity case. I cannot belive how far my fruity little tooty has come in the short amount of time that I have been sponsoring this little fairy queen for. I suppose that I could explain how sad and pathetic Sissy was when I found her. She was so sloppy looking. She didn’t know how to put her make up on and she was dressed like a bad character from a Disney movie. When I found her Sissy was sitting in a jail cell drunk off her ass and had been taken advantage of by all of the other inmates. Sissy was crying like a little faggy cry baby.

Sissy humiliation Sissy

 

I took Sissy into my home and showed her how merciful a goddess like me could be. I made Sissy clean up and take care of those assets, even that little fairy tiny tinker.  I gave Sissy some food made him sober up and I even helped Sissy get off a couple times. I put Sissy through a few tests before I really invested too much into her. I gave Sissy for explicit instructions on how to lick my pussy, jack off with my favorite butt plugs in her asshole. I showed Sissy how  Il like her to bend over when she is wearing the outfits I have picked out for her for our play dates. So far Sissy has done really good and I am very pleased with the outcome. Here is a before and after picture of Sissy. The little fairy fag I met at the jail compared to my Princess poopy pants.

Sissy humiliation Sissy

It is amazing. I can not wait to teach Sissy more and turn her into my favorite fairy faggy princess, I will ensure Sissy stays prissy and does not go back to her old ways.

Sissy maid training Clarissa

Dick humiliation and cock play

Sissy humiliation ClarissaTrying a new toy out on your favorite sissy botch’s ass is so fucking hot. I ordered a box of new toys which included a strap on dick, a bunny vibrator with an extra stong motor, a few cock rings and this ass plug which vibrated and had little silicon spikes around the rim for a little painful pleasure. My client showed up fr his nightly humiliation session and I immediately told him to get on all four and spread his pretty little ass cheeks for madam. He did so like a champ. I was feeling a little frisky, so I slammed that plug up his puckered little asshole enough that he gave me a little whimper. That made me wet fast. I love to hear my bitch, whine, cry and in pain. I then put on my strap on and face fucked him until he was so hard he had purple balls. I put my cunt up to him let him lick it until I came all over his face, I gave him a fake pussy to relieve himself into and then I sharply removed his ass plug and told him what a good little sissy bitch he had been.

Taking control and being top dog

Sissy Humiliation Clarissa

I love being in control when I am fucking a man. Nothing gives me more joy than showing him who is the boss while I ride his big fat cock and bounce my goddess titties up and own. I know exactly what I like and what makes me squirt and when I am in control I can guarantee I am going to get off and cum all over that big fat cock. I love the way a man looks at me wide eyed when I tel him exactly what I want him to do and it is even better when he is not use to letting go of control I like to grab his hair and force my tongue down his throat as I ride his fuck stick as hard as I can. I like the power play turns of him and I fighting over who gets the say as we roll around the bedroom fighting over control, sweaty, breathing hard and fuckin each others brains out. I always come out on top of course.

Tease and denial phone sex Felecia

My little sissy could not keep his hands off his tiny little clitty. No matter how many times I spanked him he just would not stop trying to rub it and get off! Can you believe how bad my sissy was being?! He needed to be punished. I dressed him up in a beautiful little frilly dress, I put a cock cage on his tiny clitty and some panties!

Tease and denial phone sex

We didn’t forget the make-up and wig! I sent him out to go get cucumbers, Bananas and some lube oh and condoms! He was so sad that I forced him to walk and take the bus to the store dressed up! He thought someone was going to take a picture of him and it be found on fb and then his wife would find out. Well if he wasn’t such a disobedient little sissy faggot then he wouldn’t be humiliated so badly! When he finally got back after an hour! He was in tears! Covered in spit, he even had this guy throw poop at him! He said it was the worst day of his life, but when I pulled up his frilly skirt I saw that his tiny clitty was rock hard and drooling!

Sissy humiliation

I knew he loved it! His punishment wasn’t over yet! I told him to tell me all the mean things that those mean people told him! I pulled out the bunch of bananas and started to fuck myself in front of him! He was begging me to let him taste me after he had such a bad day! I giggled and continued to fuck myself with that banana! Watching my little sissy cry and beg to cum! He shouldn’t have been such a bad sissy! I think I’ll keep the key to his cock cage and let him go home for the week not allowed to rub his clitty or even play with his own wife!

Domination phone sex

Mature Phone Sex Women Make the Best Phone Therapists

mature phone sexMature phone sex women make the best sex therapists. I have decades of experience counseling young boys and girls about their developing sexuality as a school sex education teacher. It seemed logical that I would take a part time job as a phone therapist. It started off with me doing this only during the summer months and winter break.  I loved doing it so much I never quit; even though my bosses at my school would fire me for  working in the adult industry. My students have the normal kinds of sexual  issues. Girls want to know about birth control and how to tell if  boy really likes them or is just using them for sex. Boys want to know how to make a girl orgasm and how to prevent themselves from cumming too quickly.

phone sex therapistAs a phone sex therapist, I encounter  far more complex issues from men, which I enjoy. Guys call me because their wives are cheating on them, usually with big black cocks. Once I ascertain that they have little dicks, I make them realize that they owe it to their wives to supply them with big dicks since they aren’t man enough to take care of their women properly. Some guys call me because they are in the closest and desire cocks of their own. I make them realize there is nothing wrong with being gay. I encourage them to swallow cum and suck cock. Some men call me because they like pantyhose, shoes and  or feet. I help them explore their fetishes and embrace them. If you like panties, you should be wearing panties. If you like pantyhose, you should be stroking your cock in a pair of silky nylons. If you like feet, you should be sucking toes and getting foot jobs. I love phone sex therapy.  Only a mature woman understands your need to be cuckolded; turned into a sissy and or forced to embrace your various fetishes.

Sissy maid training with Clarissa

Sissy maid training

Well, I found a new maid. He is so pretty and he does whatever I tell him to do. He scrubs my floors with his tooth brush and bends over so pretty as I instruct him to get on all fours and scrub harder. Oh and the pretty pink thong that I make him wear as it rides up his ass crack. I like to grab it every once in awhile and pull it up so it gets tighter and is uncomfortable for his dangling balls. Oh, plus I really enjoy when I walk in and he is not doing exactly what I told him to because at that point I make him bend over and I stick my anal beads into his tight little rectum and make him crawl across the floor because I know he secretly likes things up his asshole. By this time tomorrow my house should be fucking spotless. I am so glad I hired my pretty little maid.