Category: Sissy maid stories

Naughty maid phone sex whore

Naughty maid phone sexSissy Boy called me up for some naughty maid phone sex. He has been such a dirty sissy cuckaholic and needs his whole entire house cleaned from top to bottom from all of his sexual antics. A bunch of his big black dick friends came over to play with his sissy pee pee all night last night and clearly they have made a huge ass mess that needs to be tended to. He’s such a horny sissy, his little cock is constantly twitching just dying to be played with! He called me up and begged me to come and help him clean up the mess. Of course I showed up all dressed up in my sexiest maid outfit. My tits were pushed up and looking phenomenal as usual. My ass was nice and big & juicy, when I bend over you have the perfect view of my slutty fuck holes. Even though i’m there to help Sissy Boy clean, I am also there to totally humiliate him and make fun of all the filthy, nasty things that i’m gonna make him do! I’m looking like a total fuckin goddess as I strut around in my sexy high heels. I drive Sissy Boy crazy. He has never been this close to a real life princess before. I may be a maid but I still own him and his pathetic little pee pee. In fact, I think i’m gonna invite those big black cocks back over to his house because I want to create a little bit more of a mess and have a little more fun with him before I get down & dirty and scrub his place clean. Sissy Boy is all dressed up in his prettiest lingerie and looks like a total little whore. I shove his panties to the side and plunge one of those huge anaconda cocks inside of his asshole while another goes into his mouth. He has one in each hand while he strokes them hard. I have to whip out my phone and take pictures so that I can always remember how fucked up Sissy Boy is, lol! Sissy maid stories sure are fun to tell and talk about, especially with this special Sissy Boy!

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

 

Sissy Maid Stories With Clarissa and I

 

sissy maid storiesSissy Maid Stories are so fucking pussy wetting! Clarissa is The best Mistress Trainer around. She holds my pussy to the highest standards. When I came for my session Clarissa Had her best sissy Nathan in a maids uniform that was so short you could see his little dick in its cock cage. My, My, was it straining and bulging out everywhere like playdough. I asked her where she got such a tiny cage to make his 3 inches sweet and bulging like that. Turns out Clarissa makes her own because she has had so many needle dicks and the industry can’t keep up with the shrinking cock department of humiliation. Clarissa was so sexy it made my Bisexual teen pussy ache so bad, I knew I shouldn’t dare but I came up behind her and reached around and grabbed her gorgeous tits. Clarissa grabbed my hand commanded me to my knees. ” A Good Mistress must always start as a sub and I will teach you to be my submissive bitch!” She pulled her panties to the side and made me lick and slurp that cunt and had her Sissy Maid Nathan bring her a glass of Merlot and Ky Lube. “Ass in the air slut!”  She was drinking her wine as She made Nathan Sissy bitch boy with the tiny cocklett bring her a huge black butt plug. : This Time I will Lube it, Learn your place or I will make you pay C.J.” My ass was reamed over and over until I was breathless. My pussy came on her command. I know we are some sexy hot women and I love being trained to be a good Mistress By Clarissa! We need sissy boys, come to play with us!

sexy hot women

Latina tease

ass sex pornBefore I got into the sugar baby lifestyle, I was using my body and looks to get exactly what I wanted. I had just started working as a tutor for a wealthy family. The man of the house was very intrigued by my hot body and my sexy latina look. I was fucking him for bonuses. He loved ass sex porn and enjoyed making me watch it like a good slut. I would have to strip naked for him and let him fuck my tight twat. I love having that big cock deep inside I just kept begging for more. Each inch going in had me needing it. I was getting addicted to that daddy cock. It was like no other cock I had gotten up to that point. I was fucking pathetic dweebs my age who couldn’t make me orgasm like an older guy with experience. I especially loved fucking him in his bed where he would sleep with his wife. It was taboo and had me going every time.

My husbands younger brother

ass fetish

My husband was telling me that he needed to bring over one of his brothers. I was very irritated and didn’t like the idea; I hated the fact that his brother was such a bum. I have heard stories, but I’ve never met him. I knew he was about 22 and such a troublemaker. I knew he was going to be around the house not doing a thing.

Knowing he would be a fly on the wall present for all my rendezvous had me nervous. I was frustrated I knew it was going to put a damper on my plans.

When I was introduced to him, I saw something I didn’t think I’d see, my husband’s younger brother was everything he wasn’t.
He was handsome, and I could already tell he was well hung.

The chemistry was instant I was already wet as can be within seconds of meeting him.
To my surprise we hit it off, he was quite the Joker and told me all about his ass fetish.

I could tell he liked what he saw because he couldn’t stop checking me out since the moment he stepped in the front door.

When my husband was gone one morning, I would soon realize the extent of it. I woke up to someone pulling my panties down, and just going down on me.

I honestly thought it was my husband using his pathetic charm on me, the only way my husband knows how to get me off is with him eating my pussy, so I assumed it was him, but then I saw that it was his brother.

I couldn’t deny that I was wet as can be even if I did tell me to stop he would call me out. I let him finish up, and then I gave him a return because honestly, I just imagined his big beautiful cock in my mouth. You can imagine how much fun we had whenever my husband would be out the door from then on.

My brother in law

Edgeplay phone sexedgeplay phone sex

My husbands younger brother has been staying with us for a bit. I don’t have any shame in my game because I wait till my husband is headed to work to change my outfit real quick. My young brother in law is here from the service and isn’t working. He is recovering from a knee injury, so the rests a lot and is always around. I have been a sweet sister in law because I still take him to physical therapy and the gym to recover. I know he loves latinas and I don’t mind being a latina tease. I have even made him watch me play with my pussy. I caught him staring at me one day and told him if he didn’t sits and watch me rub one out I would let my husband know of his little peeping tom ways. I loved how beet red he got and how he almost busted out of his pants at the sight of me rubbing my cunny. You can say my brother in law, and I have gotten a little closer lately. 😉

A New Whore

Sissy humiliationI pimp sissies. I take manly men and turn them into sexy feminine bitches. Right now, I’m looking for new bitches to add to my stable of whores. I’ll put you in sexy lingerie and makeup, and you’ll finally feel like a proper woman. But putting you in sexy clothes is only half of the transformation. The last step is you on your knees with a big cock in your mouth. I’ll have the men lined up, waiting to feel your lips around their cocks. Are you ready to be my new whore? I know you’ve thought about sucking dick. So quit daydreaming and let’s make it happen. There’s only one rule, always remember who’s the boss. I’m your pimp, I’m in control. You will obey me or get punished. When I say something, you listen. Call me and you belong to me.

Sissy Boys Love Sucking Cock

Sissy humiliationI need a sissy boy.Can I dress you up in pretty lace panties? I’ll give your mouth something new to do. Let’s makes some money together. You could be my new girlfriend. Guys really like it when there’s two of us. I know exactly who to call, Raheem, has is a big spender. We could get on our knees and share his big black cock. Run your tongue up and down his chocolate sex stick. We’ll have to take turns deep throating. We have to remember to keep our eyes up because guys really like eye contact. When we have Raheem’s cock has hard as a log, we’ll bend over and give up some pussy. I’ll lick your boy pussy and leave it sloppy wet and Raheem’s cock will slide in a lot easier. I’ll hold your ass cheeks apart and help guide his cock into your tight hole. You’ll need to be a good sissy boy and moan like a porn star as he pounds your boy pussy. You and I are going to make a ton of money. Are you a sissy boy?

Dirty Little Secret

Sissy humiliationI know all of your dirty secrets, things that would shock the people closest to you. I’ll keep your secrets if you’ll be a good boy and obey. My car note is due, and you’re going to make me some money. Put on this wig and makeup, I’m going to turn you into a beautiful sexy slut. Slip our sexy ass into these black lace panties and high heels, because I have a room full of big black dicks. Get down on your knees and crawl into the room, you’re a sex animal. Black dicks will surround you, do your best to take care of each one. Open your mouth and suck and lick each huge veiny cocks. Use your hands to stroke these long thick cocks until they’re nice and stiff. Make my money and no one has to know that you’re a cock sucking faggot. I can see that your cock is hard, you love black cock! I wonder what would your loved ones think if they found out about your dirty little secret.

Sissy Boy

Sissy humiliationYou look so beautiful in that dress. And that wig and makeup have turned you into a gorgeous woman. Put on these heels and become my sissy boy. I have special guests coming over and you’re the entertainment. When we hear the doorbell ring, I want you to answer the door and pull them into my home by their cocks. Tell them you’re here to serve and please. Drop to our knees and suck those cocks like a good sissy boy. It was a really good idea putting red lipstick on your lips because they look so good wrapped around that big black cock. Get those cocks nice and hard because you’re going to give them your boy pussy. Get down on your hands and knees, put your ass in the air, face down onto the floor, and offer your tight asshole to my special guests. You are my sissy boy and I pull your strings like a puppet.