Tag: sissy humiliation

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

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.

International Tease and denial phone sex with Christmas

Cuckolding is a fetish all around the world. My international callers love my long blonde hair. They worship my body and beg me to let them cum. I have a few favorite cuckolds who take time out of their busy lives to do a call with me. Like my caller from Saudi Arabia.

Tease and denial phone sex

He called me yesterday to wish me a Milad Mubarak aka merry Christmas. He thinks I actually care if he gets off or not. He pays $2.50 per minute to talk to me and all I do is make myself cum. If he has time at the end he might be allowed to cum. But when he gives me a gift card or two I make sure to drain his balls over and over until the very last second of his call. When my phone rings again and I hear that sissy voice from Russia I get excited!

Sexy phone chat

  “Pozdrevlyayu s prazdnikom Rozhdestva s Novim Godom” Is what the sissy voice says on the other end. My Russian sissy loves to shove vodka bottles up his sissy pussy! Oh, and my favorite little bitch who calls me to worship me calls from Iraq. He loves to dress up as a Muslim woman and walk around his village. “Idah Saidan Wa Sanah Jadidah” he whimpers as a nasty muslin man brutally fucks his sissy pussy!

Sissy humiliation

Missing Sissy..

It’s been awhile since I heard her sissy whimpers. The way she gets so excited to show off for her mistress makes me giggle. Sissy Michael loves to show off for all of us here. Its been so long since I have heard her beg her mistress to allow her to do a squirty squirt from her tiny jingling balls. Wait do you guys know who I am talking about? It’s been so long since I have written about her, you probably have no idea who I am talking about??  Well Sissy Michael Fr… I’ll keep the last name to myself, we don’t want his wife finding out again..

Sissy humiliation

Anyway Sissy Michael is one of those Fairy sissy piggie bank sluts we have. Infact she is our beloved site sissy! She dances, sings and even dresses up! Her style is amazing and she can be the cutest Adult baby boy sissy fag you have ever seen! I just wanna dress her up all cute and sweet, then set her loose down Van Buren Avenue in Phoenix, she would be the sexiest cum piggie there! Hmmm I wonder if anyone would recognize her there..

Best phone sex

Sissy Humiliation from a Sexy Babe

sissy humiliationSissy humiliation is what you get when you call me with a pathetic pinky dick. Guys try to act all macho on the  phone, but I know. A cuckolding mistress knows a real man when she sees one and when she talks to one. Losers don’t ooze manliness. I understand that you are paying for a service, however, that is not a guarantee that you get to cum. Cumming is not a right, it is a privilege. A privilege of only the well endowed. So, you are asking yourself the painful question, “Do I get to cum?” If you have to ask, then no. Men with big dicks to pleasure a sexy babe like me, know they can get the job done. They are not second guessing their manhood. Only tiny dick losers and sissy bitches trying to act like men ever wonder if they got what I need. So if you don’t get to cum, what do you get? You get a lot of things actually. You get a wake-up call about your pussy status. You get to worship a hot fine woman by licking her pussy and ass clean of any and all cum left by a real man. You get to do humiliating tasks if I deem you sorry enough to put you in the sissy category. You will get your money’s worth, because you are pleasuring a hot woman. My pleasure and my amusement are what matters the most. Consider the $2 a minute an inconvenience tax for having to deal with your pathetic ass. You couldn’t get a hot mature woman like myself to even talk to you in a bar without shelling out far more money than that first. Consider yourself lucky that you have the option to pay to talk to someone like me.

MILF Phone Sex Women Love Sissy Humiliation

milf phone sexMILF phone sex keeps me pretty busy. There are so many young studs who know a mature lady is the best fuck. On and off the phone they know this. I thought I won the lottery when I picked up twin college studs Friday night. I sometimes go into this little dive bar near my house because it attracts the local college boys. Cheap drinks and cheap whores lol. Well, I am not cheap. I am rather sophisticated, but I love being a dirty whore for young guys and big cocks. The twins bought me shots all night and flirted like their life depended on it. Flattery goes a long way with me.

sissy humiliationWe got back to my place to fuck and I got smacked with disappointment. I thought I was going to be able to  take the “fuck brothers” off my bucket list that night. They were twins and so hard to tell apart, that was until they got naked. One boy had a huge cock, the other had a clit stick. One boy got fucked, the other got sissy humiliation. I don’t settle for just any cock. I know what I like. I know what I need. As his brother fucked me like the stud he was, I made loser boy kneel beside me and suck on my panties. “That is as close as you will ever get to my pussy, loser” I laughed at him.

cuckold phone sexClearly, he was shamed, but I could tell this was not the first time these studs had been in this situation before. In fact, I was pretty sure that the brother fucking me with a 9 inch dick was enjoying cuckolding his own brother. He even ordered his brother between my legs so when he busted his nut in my cougar pussy, his brother could clean me up easily. Kinky brothers. That really turned me on. The stuff that cuckold phone sex fantasies are made of, happened in my bedroom Friday night.

Sissy maid stories: the cock, the cage, and the plug

Sissy maid stories

I’ve been having so much fun training my sissy maid. It’s becoming my favorite activity next to fucking you.

Of course with our new little toy you’ve gotten a lot more attention to your cock.

Like right now. I was enjoying the site of our little sissy maid on her knees. Wearing a latex maid outfit that left little to nothing to the imagination. Her little bitch clit throbbing in its cage as it tries to get hard. I giggle as I watch it, poor pathetic little thing.

Her cock was in your mouth.  She was fucking her own throat with such vigor that you couldn’t help but lean back, your eyes rolling into the back of your head. A pool of spit on the floor between you, our sissies tears ruining her makeup and her bright red lipstick was smeared all over your cock and her mouth.

I pressed the button to the remote control vibrating jeweled anal plug in her pussy and watched her quiver. She moaned around your cock making herself gag and try to pull off of your cock. I giggled as you grabbed her by the hair and forced her back on. Fucking her mouth with short hard thrusts until your groaned.

She was quivering, her hands open and close, Gagging and choking around your cock as you force your cum down her throat.

When you let her hair go she pulled back, coughing and gagging. Tears streaming down her cheeks as she gasped for breath. When she got some control again she swallowed hard and looks up at you. “Thank you sir.”

The Best Phone Sex is Sissy Humiliation

best phone sexThe best phone sex for me is with sissies and cuckolds. Why? Because I get to be a mean bitch. Over the weekend, I met this man. We actually went to college together, but lost touch over the years.  Face Book reunited us. I agreed to meet him Saturday for drinks. Attractive man. Educated, articulate, nice and a wealthy.  Just not very masculine. I figured his more feminine voice and mannerisms were from low testosterone, which usually means small dick. I was right. He had a 2 inch willy at best. When I saw it, I burst out laughing. The gall of any man who thinks he can fuck me with a shrimp dick pisses me off. I gave him a healthy dose of sissy humiliation that began with putting him in a pair of my panties. Anything less than 5 inches belongs in panties because it will swim around lost in boxers. I am a sissy trainer. Sometimes guys come willingly to me for help on becoming a sissy, sometimes they need nudging like my college pal. He was an old friend. I couldn’t delude him into thinking he had anything that could please a woman.  That’s just setting a man up for failure. Sissies can become a very integral part of a woman’s life if they just get a little training and accept their fate. The sissy training began with panties and an honest conversation about cock size. We discussed ways he could still please a woman without actually fucking her since that would be no pleasure at all. During training, he couldn’t stop rubbing his nub. I smacked his hands away from his dick several times before I put him under lock and key. Sissies are here for a woman’s pleasure.  I only allow a sissy to touch his willy as a reward for something quite remarkable. My sissy in training can barely lick my pussy. Until further notice, he is under lock and key. I love being a sissy trainer. He will learn to worship my pussy eventually. At least if he ever wants to touch his dick again, he will.

sissy humiliation