Category Archive: Sissy humiliation

Schools In And Daddy Is Cuckolded Once Again

cuckold phone sex

Daddy has gone the whole summer getting little of this cuckold phone sex teen.  I have been so busy running around getting hard body older men at the beach I have been seriously slacking on his cuckolding. SO when I got my new schedule and saw that the Assistant Principle was a sexy black stud of a man, I had an Idea. I dropped my purse and stuck my ass in the air so this BBC hiding stud could see the lips of my cunt from under my skirt.  Mr. Assistant Principles hand came up and grabbed my ass. I guess my slutty whore Rep was known already! Yay! I backed up to him and I saw daddy peeking in the window as I was put on the desk and had Mr. BBC lick my pussy right in front of tiny dick daddy. I even gave him a little wave. daddy was dying to touch his stick dick but couldn’t in the hallway. I loved it when daddy was almost humping the window as I quickly got a load of BBC cum up my tiny sexy twat. I grabbed my purse went to get daddy and told him he could suck the cum outta of my cunt in the car if he put lipstick on for the rest of the day.  Just a little sissy humiliation I will make sure daddy goes full sissy mode later.

Itty Bitty Dick

Sexy babeI am your superior and I love fucking men especially big black men right in front of you. Letting you watch their huge cocks slither in and out of my beautiful Pussy. You know your itty bitty little dick will never compare to the 12 incher penetrating me making me squirt everywhere making a huge mess. Your only good for the clean up on us both. Sucking his cum out of my sweet pussy and cleaning off his massive BBC. Tasting my sweet pussy on his dick. We make fun of your small dicky. Your balls are like marbles and his balls are like hard 8-balls. He laughs at you and I laugh at you. I told him you had skill with your mouth and tongue and he is taking full advantage.

Eveylyn Dishes Out Some Sissy humiliation

Sissy humiliation

It seems that sometimes it takes sissy humiliation to keep your ass in check. I am having you meet me today at my home. I have decided to take you on as my personal sissy slut. I have already bought everything needed for your transformation.

When you called I gave you specific step by step instructions of things I wanted you to have done before you arrived. You called me from your car whining as usual and telling me you did not want to reimburse me for the items that I purchased because you had bought somethings yourself. I told you we would discuss it when you get here.

I think it is time for me to teach you your place in this relationship. When you arrive I tell you to go into my room undress and fold your clothes up neatly then place them in the chair. Next I want you to get down on your hands and knees at the end of the bed and wait for me. I give you a few minutes to contemplate your future.

I walk into my room with riding crop in hand. I smack your ass extremely hard causing you to scream out. I lean over and grab your hair yanking your head back. Then I whisper in your ear that you need to understand who is in charge. That you are my little sissy slut bitch and you will do what you are told when you are told or there will be extreme consequences.

Then I ask you fi you want to discuss finances and you reply no ma’am. Looks like you might be a fast learner after all. I tell you that your earlier drama has cost that cute little ass of yours and that you are to remain in place for your spanking. I smack your ass a dozen times leaving it covered in bright red riding crop marks.

Best phone sex

I tell you to reach back and pull your ass checks apart. With one hard push and no lubrication I shove a big black butt plug up your ass. You cry out please Mistress Eveylyn take mercy on your sissy slut, but your cock betrays you as it is rock hard and oozing pre-cum. I send you into my bathroom and have you sit on your sore plugged ass while I start doing your hair and makeup.

Small Dick Humiliation in the Club

small dick humiliationSmall dick humiliation was what he deserved. I am in my forties. My days of praising little dicks like they are the greatest gift to my pussy are long gone. Seriously, the audacity of this guy to think he could fuck me with three inches pissed me off. What happened was that I was out with girlfriends Friday night. This loser was buying us drinks. I guess he thought that entitled him to something more than a thank you. When I went to the bathroom I guess he misread the signal. There was no signal. I had to pee from one too many Pixie stick Martinis. He followed me into to the bathroom and pulled his cock out. Erase that. What he had was no cock. He whipped out his clitty. He expected a blowjob in the john. I am not a drunk college girl. I am a mature hot sexy woman. I don’t blow clit sticks in the bathroom of clubs. Now, if his cock was thirteen inches, that is a definite possibility. But, an inch worm, no way. I laughed at his small nub. I pulled off my panties and tossed them in his face. I explained since he had a clit, he belonged in panties more than me. He had this indignant look on his face like no woman had ever laughed at his micro penis before. I couldn’t stop laughing. I took some pictures with my camera phone, so my girlfriends could have a good laugh too. Oh, my god, he started to cry like a fucking pansy. He claimed I was so mean. He was the one who had the archaic view that buying me drinks deserves head in the bathroom as thanks. Seriously loser, what the fuck? Let his experience be a warning to you. Don’t think any woman will be so grateful for martinis that she will blow your short stack in a club bathroom. I can buy my own martinis.

Domination Porn Becomes Reality

Domination porn

We have had several sessions using erotic hypnosis to help you control when you cum, but it is not really working. During our latest hypnosis session you admitted to watching Domination porn. Things are making so much more sense now. I don’t think you really want to build up your stamina. What you are really craving is to be someone’s cuckold.

After all not only do you not seem to be willing to do what it takes to please a woman sexually, but your cock is really just barely average in size. Then there is the fact that you are quite whiny. I think it is time for you to admit to yourself that what you really want is to be made into a cuckold sissy slut.

I think that I could turn you into the perfect cuckold of every woman’s dreams. Your full pouty lips would make a perfect cock fluffer. Not to mention how cute you would look in a pair of hot red panties and black high heels. I know you long for someone to dominate you. To force you to suck another man’s cock. I have just the perfect man on stand by to call into this session.

I make you lick and suck on his great big cock. I grab you by the back of your head and force you to deepthroat his cock even though you gage. Once I am satisfied that his cock is hard enough for my pussy. I have you stop. I realize that you have already cum in your red panties and tell you to go sit in the corner where pathetic little sissy cuckolds belong. I want you to watch his big thick cock sliding in and out of my hot wet pussy and see how a real man uses his cock to bring his woman to screaming orgasm before he cums.

Then while I sit back and smoke my cigarette enjoying the satisfaction that comes with a good fuck, you can come over and clean his big white creamy cum pie out of my well fucked cunt. I expect you to stick your tongue deep inside my hot cunt and make sure to clean every last drop of his juicy cream pie out. After all that is all that you are worthy of being.

Cuckold Phone Sex

cuckold phone sexCuckold phone sex is my favorite kind of call. Guys ask me what I am into. I am into a lot of things, but honestly, nothing turns me on more than fucking big dicks and shaming little ones. My ex-husband number two has been trying to get back together with me. Not sure why, because he knows I am a cock size queen. He thinks it was some sort of phase I went through and that with Viagra helping old dicks get hard, I would let him back into my bed. I let him back into my bedroom, but not how he was wanting. When I told him to come to my bedroom, it was so he could watch me fuck a younger stud. A younger stud with a bigger and thicker cock. I was riding Tom reverse cowgirl when Dave, my ex-husband, walked in. He started yelling about what a cunt I am and how I will never change. He stopped dead in his tracks when I asked to see if he has changed. All his new bravado, I thought perhaps he had grown a few more inches since I last saw him naked. My laugher was uncontrollable when I realized he his dick had shrunk not gotten bigger. My lover told him to put some panties on to cover up his shameful clitty stick. My ex was never good with small dick humiliation. Are you? I mean, any man, my exes included, is stupid to think a size queen would suddenly stop caring about dick size. If anything, over the years, I have become more of one. I get older, but my cocks get longer. I think my ex finally came around to accepting the fact that the only place he has in my world is as my cuckold.  Think you will learn your place easier than my ex?

Got Dick?

small dick humiliation

I knew you needed small dick humiliation the moment I set eyes on you. That fucking power suit and those ray bans don’t hide shit! You thought a nice dinner and some caviar could get your pathetic excuse of a dick some teen pussy? I have been around the world and I have never seen an itty bitty weenie like that.  Three tiny inches and I can put my pearl ring around it with ease. No wonder you go for power and money because you have never been able to satisfy a women’s pussy with that clit stick! Omg, Its so fucking cute, adorable, baby-sized dick, omg so fucking funny. Not even bite-sized! Get your ass over here so I can at least see if your pussy eating skills are worth training you. Well, You can do better, why don’t you go pick out three nice pairs of my prettiest panties. Yeah, you will be buying me more. We need to go scouting for real dick baby. My fuck holes cannot exist on licking alone now can they?  I bet you have an ass fetish or a fetish for your ass being fucked. Either way, you are now my sexy fucking bitch. Bow to your mistress and procure me large thick cock. Let the cuckolding games begin!

Cuckold Phone Sex Date

cuckold phone sexCuckold phone sex was a favorite this weekend with me.  I think men crave slut wives more in the summer. Women wear less clothing in the summer, which means more men check them out. Face it, you enjoy men checking out your wife. You may even like it more than she does. It is not just husbands who enjoy the attention women garner either. I was on a date Saturday night with a man I met a few months ago. We have been dating casually. We have not yet fucked because he has an average cock. It is not huge, it is not small. He is within my cock size parameters to fuck, but just barely. He is handsome, intelligent and wealthy, just not hung. He is a very good pussy eater, so that scores him points. We went to a dance club after dinner. Some young stud was checking out this mature sexy babe. I wasn’t sure Eric noticed, but he did. He made a point to tell me. In fact, he talked about it more than I did. I began to wonder if he liked to watch. I asked him some questions about his first marriage. He admitted his wife had lovers and he watched. That made him a cuckold, but there are degrees of cuckolding. Some men suck cock and get fucked in the ass. Others just watch and maybe get some sloppy seconds. Eric was the later, so I brought the stud home to fuck. I have cuckolded many men in my life, including 2 ex-husbands. Eric was the first man who didn’t fall into the first category of cuckolding. He had an okay cock. He didn’t deserve sissy humiliation. He got to stroke his cock and watch a college boy fuck my mature pussy for hours. For being a good voyeur, I let him eat my creampie. Just when I was thinking about dumping him, he proved himself useful.

I need Big Dick

Small dick humiliationI can’t help that small dick humiliation turns me on.

I need Big Dick!

Is that too much to ask for?

So if you have a clit dick, an itty bitty weenie, I am going to humiliate you.

Plain and simple. I have no time for little dicks , unless of course you want to spoil me and let me fuck the biggest thickest dicks right in front of you. Maybe you should put on some panties you pathetic no cocked loser. Be my flaming fag bag finding this hot teen big humongous cock. Suck and stroke those big dicked men that you are so fucking jealous of, loser.

That stump is not going near my Pussy or ass. I think you should take a nice juicy THICK cock in your man Pussy so you know how my Pussy feels bitch. And if your lucky and buy me nice things I will let you be my cum dump. Lick it out like a good boy


My Brother’s Got A Tiny Secret

Phone humiliationSo school is out for the Summer and I figured a visit home wouldn’t be to bad of a idea. I’m honestly glad that I did. So someone must of forgot to tell my brother that I was going to be coming home. I knew he was home cause he car was in the driveway. I left myself in and I could hear the tv on upstairs. It wasn’t until I got near his door that I could make out he was watching porn. *Giggle* I only opened the door cause I was curious what my brother was packing he is always talking himself up. But once I opened the door and saw him jerking his hand up and down about just a inch II couldn’t hold in the laughter. I couldn’t even see his cock. Completely hidden by his hand. He was so embarrassed he just shut down. *Giggle* Honestly maybe he was suppose to be a girl, my clit gets bigger then that little sausage.

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