Category: Sexy dominatrix

The Smallest Dick

Small dick humiliationI started dating this new guy a few weeks ago, his name is Mike. After a few dates I was ready to fuck Mike but he kept putting me off, and saying he wasn’t ready. I finally had enough and demanded he tell me why he didn’t want to fuck me. That’s when he pulled his pants down and showed me the smallest dick I’d ever seen. I couldn’t help myself, I laughed. I laughed hard, like fall to the floor holding my belly laughing. His face turned bright red and he had the smallest erection. That made me laugh harder. My sister was staying with me and my laughter woke her, she knocked on my bedroom door wanting to know what was going on. I told her to come in and see for herself. Mike tried covering himself, but I made him show my sister and she too fell to the floor laughing. Small dick men are hilarious!! Do you have a small dick?

Sexy dominatrix, breaking in the new employees

Sexy dominatrix

I am a cuckolding, trophy wife to a sissy. My hubby is a very successful business man and is very demanding in his office environment. My job is to break in the new employees that come in. Not for my sissy husbands amusement, but for my own.
I love strapping on a cock and teasing their pussies, letting them know that my hubby’s name might be on the building, but I’m the boss of what goes on in the office with keeping everyone happy and things running smoothly. If I didn’t, there would be crabby chaos from work long hours and not getting the sexual release that is needed.
So I train all the new people, men and women. A new secretary started a few days ago and I brought my strap on to welcome her to the company. She has such tiny little perky tits and nipples so sensitive. My sissy watched from his desk chair and I allowed him to jerk off. I ran my hands lightly over her skin just barely grazing her nipples. They got so hard she told me they were pulling and aching. So I made sure to play with them even more. She was wet from me making her undress slowly in front of me so I slid the strap on into her tiny tight pussy and fucked her until she came all over the dildo.
I made sure the new girl came a few more times before wrapping things up. After she was dressed she expressed how fun this place would be to work if fucking was a daily task on the office agenda. Great! We have a dedicated new employee.

Small dick humiliation with Loretta

Small dick humiliation

I love cock! Just not my husbands tiny worthless pinky dick! I need big hard cocks in my holes! I love getting my asshole stretched open by a big hard cock! All while making my tiny dick loser cuckold hubby watch! He sits there and rubs his tiny pathetic cock while my tight ass is getting pounded by a big hard cock! My poor tiny dick husband can’t cum yet. He has to wait! He has to wait until this big fat cock fucking my tight asshole makes me cum! He has to wait till that cock fills up my dirty little hole with his salty spunk load! Then my husband has to eat the cum out of my freshly fucked ass while he rubs his tiny worthless cock. Then he can cum.

Sissy maid training Rob

Sissy maid trainingI think I might have a new sissy go play with. Her birth name is Rob but I’m thinking of a new and more appropriate name. She is an eager, sweet, sissy with a baby face and a head of beautiful light red hair. I have already bought her a sexy maid uniform and a slutty hoe dress to wear when going out. Like right now, she’s face-timing me as she sits in a park. Dressed like a good slut and sucking this stranger’s cock for “tribute” and confirmation to what a good sissy slut she is. The stranger had his fingers in her hair using her throat like it’s a flesh light. My sissies eyes watering and making her mascara run as she gags around this strangers cock. It’s so much fun, she is almost like a puppy. So eager to please even while being abused.  I can’t wait to see just how far I can push her and how much money I can make by making her my whore.

Cuckold phone sex with Loretta

My husband wanted to have sex. I told him I had a headache. I told him to go take a long shower and jerk his own cock. He slumped away and got into the shower. I giggled to myself as I started to rub my pussy. I was horny as fuck, I just did a line before he came in here. His tiny cock was hard and he wanted to know if I was willing to have sex. HAHA! I’m not high enough to let him stick his tiny cock inside of me yet. I know he will make himself cum in the shower and I’m gonna start playing with my pussy doing line after line.

Cuckold phone sex

The higher I get the more willing I am to let my husband pay me to have sex with him. I heard him cum and turn off the shower. When he walked out he saw me fisting my pussy! I told him I changed my mind and was ready to fuck. I told him to get hard. I laughed as he tried so hard to get his raw cock hard! He must have rubbed his cock so hard in the shower! Now its so tender he can’t even get it hard!! 

Be a bad sissy, to be my good sissy bitch

Sissy Humiliation ClarissaHave you ever had a sissy that did so well you did not have anything to punish them for anymore because they were such a good little bitch, you just cannot punish them. One of my sissy maids is so perfect and does everything that I say that I just cannot seem to find anything to punish him for, so I have been having to make stuff up. I will punish him for licking my asshole to slow, when he was doing it just fine. I have punished him for getting saliva on my boot after I told him to lick it. I kind of feel bad but it is his fault he does exactly what I want. I think I need to tell him to disobey me so I have something to yell at him for and put his cock in a nice vice grip contraption. Its no fun if I cannot toture his cock and balls a little bit, but I want a reason to do so. I am ordering you to be a bad sissy, just to prove you are my good little sissy.

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

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.