Tag Archive: sissy maid training

Sissy Boy Maid Wanted

Best Phone Sex

I’m looking for a pretty little sissy to make into my new toy. I need someone who I can force into playing dress up! Pretty sissies are my favorite toys! If you want to be my new sissy slut, you have to do everything I say. You have to be my pretty faggy maid and wear a pink maid uniform while you dust and worship my rubber cock. . 

I want a sissy who will wear pretty lipsticks and will gag on my strap on! If you are a really good little fag, I’ll even bring one of my boyfriends for you to suck. I love rewarding my sissy fag toys with creamy cum! And if you’re a really good toy, my big dick boyfriend will fuck your boy pussy so hard. I love watching you get fucked on your hands and knees while I play with my wet, bald cunt. I love watching my boyfriend fill you up with cum! So, do you have what it takes to be my new toy?

Sharing My Pet

Sissy maid training

First off, if you do not know Nicolette then allow me to introduce you to her.  She is one of the kinkiest friends that I have.  A few years ago I helped her with one of her sons.  Since that time her and I have become fast friends.  She is super hot.  I mean, look at her.  Her tits are simply amazing. Now onto the story part of this blog:

Nicolette was spending a couple days with me so we could catch up on things since it had been ages since we had spent any real time together.  Our conversation turned to sex.  For some reason it always does when the both of us are speaking together.  I told her about how I can afford to now pay people to have sex for me while I watch.  How I have a new play thing who was at his Parent’s home for the Holidays, and that I started learning about BDSM.  When I mentioned that she perked up quite a bit.

She asked me if I could get a hold of my pet who I play with now and then.  I told her I could most certainly try.  I texted him and being the good pet he is, he texted right back even though he was out for dinner with his wife.  I told him that I really didn’t care that he was there with her, I wanted him here, now!  He sent back a short reply of, ‘Yes Ma’am.” Then we waited.

Forced feminizationWhile we waited we went up to my closet to pick out some appropriate apparel for our fun.  The doorbell rang and I went to answer it.  He was there, kneeling by the door to request permission to enter.  I told him not yet and yelled for Nicolette to come down.  She came to the door and laughed.  I told him he could come in, he looked confused.  He wasn’t used to having anyone with us when we played.  I introduced them and we were on our way.

We made him put on a pair of panties all while informing him of what the night would hold for him.  He didn’t like wearing the panties, but tonight he was our little Sissy and he would be trained to be our Sissy Maid.  He stood there in those panties, it was almost comical, he was truly embarrassed.  Nicolette suggested that he be punished for not liking what his Domme had given him to wear.  I told her where the gear was and she brought out everything.  Her and I decided on the canes.  He bent over while her and I took turns reddening his Sissy ass.  With each swat he had to apologize.

We then moved onto some strap-on play.  I have to say, Nicolette was a beast with that thing.  I have never in my life seen someone get fucked so hard.  She was thrusting into him so hard that I thought for sure he would go shooting out the window onto my front lawn.  She then made him clean off that which had been so violently rammed into his ass.  I went behind him and continued to widen out his Sissy pussy.  By the time we were done he was in tears from the humiliation, and Nicolette and I were enjoying seeing those hot tears running down his cheeks as he thanked us both for the lesson.

Sissy humiliation

 

Phone Sex Therapy: I Can Size You Up with a Glance

phone sex therapyDo you need phone sex therapy? Many men do. This hot sexy doctor is in. I am a doctor too. Not an MD, but a PH. D in psychology. I teach college by day and have phone sex by night. I have extensive hours and research in human sexuality and behavior. I can tell you if your wife is cheating and likely tell you why. I can tell you if you are gay, a sissy or a fetish panty wearer. I can size up men with a glance or a conversation. When Trevor was hitting on me at the bar last night, he didn’t like the fact that I sized him up so quickly and so precisely. I told him he had a small dick, that he over compensated with expensive clothes, a sports car and by flashing his money. He told me I was full of shit. I had him put his money where his mouth was by proving me wrong. I made a little wager. If he had a dick bigger than 6 inches, I would go home with him. If he had less than that, I would peg his ass in front of all my girlfriends who were with me. He took my bet. I thought for a moment perhaps I was wrong because most men would not take that kind of bet if they thought they would lose. I wasn’t wrong. He just wanted some small dick humiliation and a good ass pegging. He measured less than 4 inches. My girlfriend took off her panties and told him he belonged in panties not boxers. He put them on and I pegged his ass with a beer bottle. I didn’t have my strap-on with me. It is something perhaps I need to stash in my purse for such occasions. Trevor fell in love. Not with me, but with that beer bottle up his ass. Hardest his dick has ever been.

Spanish teacher slut

naughty teacher

The new Spanish teacher is a naughty teacher in your school. I like being the schools head slut. I’m not even a student, and I fuck more than most the girls on campus. I love seducing young guys who will do just about anything to fuck all the  students. I have no shame. I have broken so many campus relationships! Oh well, like to use my body to suck and fuck. I love being a little cum slut. I want all positions and being used and teaching you new things. After all, I am the teacher. I will sread my legs for big a cock. I have no limits and will guide you how a real whore likes to fuck. I get my holes filled at all hours of the day I get loads and pass on A’s.

Black Friday special

Sexy babeMy husband was asleep and I knew he would wake up if I tried to leave so I came up with a perfect plan, I was going to go shopping for black Friday, I knew this plan would work because he never questions me when it comes to shopping, He knows I’m an expert shopper, but the truth was I was so horny and ready to fuck, him being off and away from work for the holidays was making me antsy for real cock! I just wanted to use any type of excuse I could possibly use and run with it. It was my yearning for cock that made me lie and cheat, I have said it endless times I can’t get off with my husband and I look for cock everywhere I can, it is really not that hard to find anyways, a sexy babe who gets what she wants always, Like you guessed yep my plan worked. I went on a fucking spree. I did end up buying some stuff but the cocks I got were my highlight.

Gaping Holes

Sissy humiliationWhen you’re with me, I’m in total control. You have to check your manhood at the door. When you walk into my home I take your manly name away, you’ll be called Britney, Cindy, or Veronica. You’ll be my bitch. I’ll dress you up real sexy. A pretty dress, some makeup, and a wig will turn you into a fuckable slut. I have men lined up and ready to fuck your tight holes. You’ll be my beautiful sissy and mine to control. You’ll look good on your knees with that dress hiked up to your waist. Move those panties to the side and let me see that tight boy pussy. Spread your asscheeks apart and show me that tight butthole. Your cock is so hard I can tell you’re ready to be fucked. You walked into my home as a man, but you’re leaving as a slut with a gaping asshole.

Erotic Roleplaying and Sex Therapy With Gwen

erotic roleplayingGwen likes to do sex therapy sessions with you. She wants to hear all about your sexual desires and what kind of erotic roleplaying makes your big thick cock get rock hard. Nothing is ever off limits or taboo with Gwen. You are always free to share with her your dirtiest, kinkiest, and wildest sexual fantasies. I will never judge you. The truth be told I am a very kinky girl and your dirty little sexual secrets make my pussy soaking wet with desire. If you dream of fucking sisters Gwen wants to hear about it. If you want to be a sissy slut tell Gwen all about it. If you have a foot fetish or want to role play share it with Gwen. Gwen wants to help you live out all of your wildest kinkiest sexual fantasies, but you do have to tell her what they are before she can help you.

Cuckold Phone Sex: Shaming Losers

cuckold phone sexDo you enjoy cuckold phone sex? You must be a loser if you said yes. I love losers. I won’t fuck a loser. I married two losers so no more losers in my life. I mean no more losers in my pussy. I have no problem turning a loser into a cuckold or a clean up bitch. I also have no issues with shaming a loser. This guy I know loves to be publicly shamed for his little dick. He pays me for it too. Poor bastard. I had him over last night for girls’ night. Talk about fun. Me and 10 other hot babe size queens into small dick humiliation. We had him stand in front of us. We spent a good half hour ridiculing his little pinky dick. We wrote Loser and other such things in red lipstick on his body. The fun really happened when we dressed him up like a sissy. We even did his hair and make up. We put her in a sissy maid outfit I have for such occasions and took pictures for public shaming. We made him up load the pictures to his Face Book page so his family and friends could see what a shameful sissy loser he had become with our help. I broke out the bag of tricks so we could all fuck his little boy pussy. He cried and pleaded with us. Even claimed we had gone too far, but I knew he wanted a good ass fucking. All cucks and sissies love their asses played with, don’t they? You know what I am saying is true because if you are still reading this, you are enjoying what I have to say. Your little clitty is throbbing. Put on some panties, get out a toy and let’s have some fun.

Sissy Maid Training with Gwen

sissy maid trainingI have so much fun with sissy maid training. I always keep your little cocks in a cock ring because after all once I make the transformation of turning you into little sissy girls you no longer have a cock. You have a pussy instead. Sometimes I like to dress you up in a maids outfit and shove a feather duster up your tight little puckered assholes. I tell you that you had better do a good job dusting and laugh as you are wiggling your ass trying to dust the coffee table. You knocked a lamp off of the end table and that just won’t do. So I have you bend over and place your hands on the coffee table. I have found that my riding crop always helps you to remember to be more careful. After a dozen of well-placed smacks on that ass. I start fucking your ass with the feather duster. You are begging me to release your cock ring and allow you to cum. But I don’t. Instead, I tell you to go do the dishes and leave that feather duster up your ass. Maybe if you do a really good job cleaning I will allow you to come…..only time will tell.

Sexy Dominatrix Gwen

sexy dominatrixYou called and arrange a session with a sexy dominatrix. I told you to be here promptly at eleven o’clock in the morning. It is now twelve and I have not seen or heard from you. I am starting to think that you have chickened out. Then my phone rings and you start making excuses for being late. Which is totally unacceptable. You should have called me at the time of our appointment not thirty minutes later. By the time you finally arrive you have wasted over an hour of my time. I let you know that you will be paying me for my wasted time and this is no longer going to be a sexy domination session, but instead a sissy maid training session. You will be paying for your naughtiness. I have you take off all of your clothes and then put on a super slutty maid outfit with crotch less panties, stockings, sexy high heel shoes, and last but not least some red fuck me lipstick. Then I hand you a feather duster and tell you to start cleaning. Every time you bend over I give you a hard smack with the riding crop. Before long your ass is covered in pretty little red welts. The door bell rings and you go to hide. I tell you you had better get back to cleaning my coffee table if you know what is good for you. I open the door and one of my luscious dark chocolate friends is standing there. He notices you right away and says well Mistress Gwen what do we have here as he licks his lips. You’ll have to call me to find out what happens next.

sissy maid training

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