Category: Sissy humiliation

A Lesson In Obediance

domination phone sex reneeMy pussy twitched in unison to the sound of my riding crop across his chest. My nipples hardened as he twitched and lowered his eyes in shame. He dared to look me in the eye knowing that he is my slave and I am the Mistress. The thrill of his whelping flesh before my eyes and his instant erection from the crack of the riding crop creates moisture between my legs. “How dare you look at me when you have not been given permission to do so! On your hands and knees NOW!”  I slowly walk around him with his eyes obediently lowered I run the crop down his back to his ass, now covered in goose bumps. Lifting my crop high I lower and the sound of it hitting his flesh causing him to twitch sends tingles through my body. I hear a sniffle escape his lips and I smack his ass again with displeasure. “Take it like a man and stop your whimpering or you will never be allowed to cum!” Giving him a third smack I see the small drops of blood begin to rise to the surface of his skin. His twitching cock responds to the punishment just like a good little slave. Grabbing the ball gag I shove it into his mouth roughly and I see a small drop of blood escape his lips. “It is going to be a long night for you. Never displease your mistress. Do you understand?” Nodding his head in affirmation I smile while retrieving a vice for his cock, one of the many instruments I will use to administer his punishment tonight. Renee is no where to be found and Mistress Tabitha is in rare form tonight.

Sissy Domination Phone Sex Sessions with Mistress Farah

sissy humiliation tiny dick loserI love sissy humiliation. I have a good friend, Goddess Levi, who called me today, to talk about this particularly pathetic sissy she owns, who is aptly referred to as Sissy Fairy Fag. SHE is the kind of sissy perfect for sissy domination phone sex, which both Goddess Levi and I so thoroughly enjoy. I laughed hysterically on the phone with her as she told me stories about her little piggy mascot. Now, I have trained and dominated many a sissy in my life, in fact I have several sissy servants, but her SISSY, is the queen of the sissies; queen of the fags; queen of the losers. Since Sissy Fairy Fag is somewhat of a house sissy to the women at my company, I have no problem telling you about some of her pathetic antics so you can shame her too.

sissy domination phone sex fairy fagPersonally, I love a sissy who dresses elegantly, which this particular sissy does. However, when a sissy makes a mess in her frilly panties like a bad little girl, is not elegant at all. I cannot help but shame that sissy for being a pathetic poopy pants. Goddess Levi, like most of us dominant sissy mistresses, must shame and punish any sissy who cannot hold her business properly. Sissy Fairy Fag makes public messes, then sits in her own excrement like dirty girl. If one of MY sissies made a big nasty stinky mess like that, not only would I rub her face in it to teach her a lesson, but I would take pictures to share on our social media. We have Facebook and Twitter accounts perfect for public shaming of nasty, dirty sissies. Goddess Levi went on to tell me all about the humiliating tasks she has made her Sissy Fairy Fag do. As I was listening to her tell me story after story, I got aroused. Sissy humiliation makes me wet. And of course it reminds me that my clit is bigger than any sissy dick.

sissy maid training fairy fagsA sissy trainer is always on the lookout for new recruits. But, I dominate my sissies. I will take control of a sissy’s everyday life, even bathroom time. I will own my sissies, and outward signs of ownership will be shown. I am fond of bedazzled collars and leashes. My sissies will obey and serve me, however I deem fit, even if that means sucking dong and having sexual relations with my other sissies.` Sissies will seek my permission to do anything and everything. I have both phone sissies and real time sissies, so don’t think for a moment that if you call me, I don’t know what I am doing. And with that being said, don’t ever think you can dictate how our sissy sessions go. When it comes to sissies, you will do as I wish, and if you don’t, I have many unpleasant and embarrassing ways to break you.

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Sissy Maid Stories with Maggie

sissy maid stories sexy sissy trainerDo you have your own personal sissy maid stories you can’t tell many people? Well , you can tell me. I love sissies. My parents only had me, so I had no siblings. However, I did have my very own sissy to play with, Serena; a friend of my parents who essentially had no dick, but wanted to be a part of their wild Hollywood life style. She was given to me as my personal servant/play thing. Twenty years later, and she is still serving me. When I was younger she made me my meals, cleaned my room, did my shopping, played games with me, even took me to and from school. My parents of course made her wear a French Maids outfit and curtsey every time she was greeted or I gave her an instruction. I was a little bossy bitch, still am, so I had so much fun ordering Serena around. I loved sending her to the store to buy me things like tampons and lube. I’d even send her to the adult store to buy me vibrators.

Now, she still does whatever I want and need, but I whore her out to my lovers also. I think it is so much fun to make her clean the sheets after a real man and I have fucked our brains out, leaving the linens drenched in cum. She will be in the kitchen making us food for after our fuck fest, and I will summon her up to the bedroom to immediately clean the sheets, and I will sometimes force feed her my cum drenched panties to wash by hand, well, by mouth! I even make her clean my pussy and my lover’s cock with her mouth too. It is so amusing to watch Serena curtsey with a mouth full of cum.

sissy maid training hot gfeWhenever I summon my sissy she comes. Does whatever domestic or not so domestic task I require. Been with me for over 20 years. I love my sissy like I would a sibling, but she is getting old. She tries her best to keep up with me and my sundry lovers, but I believe a need another sissy to assist me with the day to day tasks I am simply too hot to bother doing. So I am now excepting application s for a new sissy. No experience necessary, just a willingness to serve and the ability to follow instructions properly, without complaining. Serena had no experience, and I trained her as a little girl to be one of the best sissies around. I turned a rather alpha male into a silly little song singing, cum guzzling, frilly dress wearing, curtseying, fairy fag, sissy maid. I can train you to be the best sissy around too.

You Might Be Submissive….

phone humiliation ReneeWhen he invited me over for dinner I thought nothing of it. We had been friends through the law firm for a long long time. I had never known of him dating any one and just assumed he was gay.

We had a pleasant evening and he cooked a great meal. As always the conversation was casual small talk. But for some reason he seemed a little off. Kind of edgy. While he was cleaning up after dinner I excused myself to the rest room. I couldn’t resist the urge to peek in his bedroom as I walked past. Curiosity took over and  I slid the dresser drawer open and was stunned to find a drawer full of knee pads. I was now certain he was gay and attributed his strange behavior to him wanting to tell me but not being sure.

The night was drawing to an end and I still sensed something so I  offered to return the favor and cook for him the next night.

I had just come home from the pet store and buying my two dobermans new spiked collars and leashes. They were on the table when he arrived. I offered to make us a drink and when I came back in the room he was holding them with a look in his eyes that was very familiar. Tabitha had seen it many times.

He followed me to the kitchen to help with the final preparations for dinner. All the while hinting at something but not coming out with it. When he opened the utensil drawer to retrieve a serving utensil for dinner I noticed him eying and touching several utensils in a longing way,

After dinner as we were carrying our drinks to the living room I held up my glass and said in a loud and commanding way, “Bottoms up” He hit the floor with his ass high in the air.  After a minute he looked up at me and said he was just following orders.

That is when I found out he had heard about Tabitha and was a submissive. He was trying to tell me he wanted me to be his mistress and didn’t know how to ask.

The moral of the story is, if you have a drawer full of knee pads, you are envious of the dog’s new collar, you are aroused by the utensil drawer and you hit the floor with your ass in the air when someone makes a toast, you are probably a submissive.

Foot Worshipping Sissy Boy

I’ve ordered you some panties. A lacy black thong, cut super small. Don’t worry, your little clitty will fit just fine. I’ve got a bra for you to put on, and a dress, and I’ll do your makeup and put on your wig! I’ll step back and take a look. What’s missing? Ah! Your shoes. I’ve got the perfect shoes for you, but you know what? I’m wearing them. Foot Fetishes

Get down on your knees, sissy boy. The shoes I want you to put on, are currently on my feet, and you need to clean them. With what, you ask? Your tongue, of course! You will look so fantastic, so pretty, my little sissy pretty boy on my arm. The shoes will complete the outfit, but first they must be cleaned. Start at the toes. Suckle my toes the way you wish to suck these perfect tits. Now lick the tops of the shoes. There isn’t much, just a little strap at the toes, but ugh, there’s dust. That won’t look good on your toes. Now run your tongue up my insteps, however you’d like. You love my dirty feet, don’t you, faggot? Now there are straps running along the ankles, clean them well. You have to look so pretty. Alright, once they are clean, I’ll take them off and slip them on your feet. Now what color shall we do your toenails? I’m going to do purple, a perfect sissy color. Now between the thong, the skimpy dress, the makeup, the wig and the shoes, we’re ready to go out on the town with you as my pretty boy.

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Phone Sex Terapist Maggie Can Transform You Into the Perfect Pretty Sissy

phone sex therapist sexy gfeWhen you have a job like this, you find yourself being a phone sex therapist. Guys call me all the time to share their deepest secrets and darkest desires. You see many of you have things you just can’t tell your wife or your girlfriend. You fear they will not understand you. I talked to a guy this morning who likes to wear women’s panties and pantyhose. He is a big corporate type, but if anyone knew he had girly things on under his Armani power suit, he would not be taken seriously. He asked me if I thought he was a sissy. I asked him what size dick he had, if he likes cock and if he dresses in pretty frilly things.

He has a 2 incher, which is more like a clit. He fantasizes about going to glory holes and wants his wife to share her lovers with him. But he has never worn more than panty hose or panties. I gave him some tough love. He is a sissy in waiting. He just needs a little help with his transformation. I am going to be his sissy phone sex therapist. He has a series of feminization assignments from me to become a full fledged sissy. First order of business, shave her entire body. In fact, I talked with her while she shaved her chest, arms, legs, back, cock and balls, even under her arms. A sissy has a smooth pretty body just like me. I forbade her to use manly deodorants or sprays. A sissy smells like a girl. She is to wear Bath and Body Works body spray and wash, a floral scented kind. She must buy girly shampoo and start using Secret deodorant. She also needs to start using feminine hygiene products in her pretty pink panties.

We talked for quite awhile. She seems really eager to become my sissy. Of course I assured her I would be with her for every step of her transformation. When she calls next, we are going to do some online shopping for the perfect sissy maid outfit. Baby steps. A good sissy, a lifestyle sissy, is not born over night. Do you have the dedication to become the perfect sissy? Do you have the obedience to submit to a sexy sissy trainer? Can you complete tasks and assignments in a timely fashion? If you answered yes to all three questions, then you can have the privilege being trained by me. I’m a sensual sissy trainer, but I can be quite cruel and humiliating if you don’t follow through with your tasks!

Call me and let the transformation begin. You know are a sissy at heart. You just need the right mistress to reach your potential.

Cuckold Phone Sex with Maggie: Are You a Lover or a Cucky?

cuckold phone sex hot gfeCuckold phone sex is a way of life for me. In my world there are two types of guys. The ones you fuck and the ones you don’t. Lovers and cuckolds. I have both in my life. You see I consider myself a hot babe. I’m the whole package: beauty and brains. I have the body to get the cock I want and the brains to never settle for cock I do not deserve. Size matters with me. I have this fellow doctoral student who wants to fuck me. Sure, he is good looking and smart. Qualities I like in a guy. But, he has a 2 inch dick. That isn’t even something worthy of being called a dick. It’s a clit stick. He has been persistent in getting in my panties. Actually, he has been a bit cocky no pun intended. Insists he will be the best fuck I have ever had. Such bravado needs to be taught a lesson in humility. I invited him over; let him think I finally caved.

I poured us some drinks, suggested we move things into my bedroom. I asked him if he had ever experimented with some light restraints? Convinced him it would be much more intense if I tied him to the bed. Foolish boy. Once I had him tied up, I walked over to my bathroom, and let the real man come out to play. A fellow student, but an appropriately hung one. This guy had 9 thick hard inches, making him about 5 times the man of Ms. Clit Stick. I simply explained the difference between a man and a sissy; between a cock and a clitty; between a lover and cuckold. He was the later.

cuckold phone sex creampieI got the real man on the bed with me, right next to my little cucky. I swallowed his shaft, struggling to get every inch of him in my mouth. If you are sucking a real man’s cock, you almost never can get it all in your mouth. It is one of the measures of true manhood. Another measure is when he fucks you, it hurts. His cock is so big that it stretches your pussy and ass out. A little cucky boy a woman NEVER feels. If your woman says, “Are you in yet?” Then you should realize you aren’t lover material. I fucked my lover in front of my cuckold. Let him fuck my ass too. He did all the things to me my cucky wished he was man enough to do to me.

He didn’t seem to be enjoying the show. He was having trouble accepting the reality of the situation. When my holes were filled with premium stud seed, I squatted over the face of my captive cucky. Told him all he was good for was fluffing and cleaning up. Pushed that cum right in his mouth. Sat on his face until he was forced to tongue the jizz out of my asshole. My lover just laughed at him. Even tossed him a pair of my panties to wear home. It was a great night for me. I put a tiny dick loser in his place; got fucked by a well hung boy; and fed that loser my creampie. My cuckold likely didn’t enjoy his evening, but guess what? I don’t give a fuck. Don’t try to fuck me if you don’t measure up. There are only two kinds of men in this world. Lovers and cuckolds. Which kind are you?

Cuckold Phone Sex with Claudia * Watch My Pussy Get Pounded

Cuckold Phone Sex Claudia Tonight it was time for my Cuckold Phone Sex callers to be delighted as I began to tease my tortured limp dick loser cucky hubby for them. One by one, I picked up my phone and let my callers know just how small the hubby’s dick was. We laughed as they would tell me what I should do to punish him for thinking he would please me with that tuft of skin! I eventually just let in my huge cock fuck toy and told the hubby to take a good look at just how much my sweet cunt was being stretched out.

I threw a pink pair of panties and told him to put them on, it was time for him to be a good panty pansy faggot. Only when he is wearing his panties can he touch his sissy clitty. Stroke it through those pink panties as you watch cock after cock take my cunt and pound it hard like a real man would do! Once that real man unloads his spunk inside, Cuckold Phone Sex Claudiathen he can suck the cum out of my cunt. I love when a real man fucks my pussy. I love watching his big balls swing back and forth and smack my clit. I love the slick shaft, drenched with my cunt juice as he slides it in and out of my honey pot. I love when he talks about how small my cucky hubby is. Dishing out so much of our Small Dick Humiliation during our hot fuck sessions really gets my juices flowing, and I love watching the pain on my sissy hubby’s face! It is so hot! Cock after cock I will take, and he will get them nice and hard for my cunt, like a good cucky.

I know there are many of you out there with huge cocks, wouldn’t you love to show a limp dick loser just how a real man fucks a real woman?Cuckold Phone Sex Claudia

I am going to run out of batteries

Sexy Babe ClaudiaThe hubby had to work late, so I don’t even have him to keep me amused! Boy will he pay when he gets home. Especially since when I get bored I get antsy. I start going through things that I probably should not. I started to go through his things, trying to think up what I could punish him for. That is when I found something odd in his shaving kit. He has been worried about his performance it seems. I found a bottle of pills. What do I do? I take one. Find out later it is generic for Viagra. Old fucker.

Now I am horny so dam horny. He sure is gonna be paying for this. My sweet cunt is literally drenched each time I move! I try to get a hold of many of my friends. It is Superbowl Sunday! I am not sure I can get anyone on the line. So here I lay, naked in bed, with my toys in hand. I have been cumming all afternoon and would love for a dirty young, old, married, horny guy to give me a call. I have a million things running around in my head. Ready for this?

An Indecent Proposal: Small Dick Humiliation with Maggie

small dick humiliation goddess gfeThis weekend, I got a bit tipsy at a department party. A professor of mine offered me a special assignment as his research assistant for some extra money. I told him about my new job as sexy GFE phone girl. I guess he thought that meant I was easy and a sure thing. He pulled his pants down almost immediately and threw $30 on the his desk. I didn’t know what was more funny. The fact that he thought he could fuck me for $30 or his tiny little clitty I had to squint to even see? I told him I wouldn’t shake his hand for $30. I have done plenty of escorting. Just to have me on your arm in clothes will cost you a minimum of $1,000. For $30, you can go fetch me a chai from Starbucks, which you pay for of course.

I think my professor was mistaken by my California girl next door appearance and thought I was a sweet pushover. We had a come to Jesus talk. I proceeded to call him a pathetic sissy fairy fag loser for thinking for a moment with a dick smaller than my pinky finger, I would fuck him, even for money. No amount of money makes me waste my time on pin dicks. I’m book smart, and sex smart. I know what a woman like me deserves and it’s not a shrinky dick. I explained this little thing called sexual harassment. You see universities frown on it. Gives the school a bad reputation. Just like asshole professors with tiny dicks who don’t know their place, give sissies a bad name.

sissy humiliation perfect breastsTenure can be taken away nowadays. I suggested he pay me for that research job, but do all the work. And in return he gets to be my sissy maid. He will fetch me my morning Starbucks, pay for my bi weekly manis and pedis, clean my house, do my laundry, clean up my doggie’s poo, maybe even eat my hot ass and cunt if he proves to have any oral capabilities besides slewing bullshit. Oh yeah, and he can keep his tenure, and his wife. I hope she has a boy toy, because no way her hubby is satisfying her.

It is amazing how quickly men can clean their act up when presented with the loss of their jobs and family. Prancing around in panties and a French maid’s outfit singing about your little dicky while being a hot student’s bitch doesn’t seem so bad after all. I’m gonna have so much fun with this one!

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