Category: Sissy maid training

Sissy Son Dressed Up and Shown Off

Sissy boy mommy

Mommy loves taking care of her beautiful sissy son. I love to dress you up like a little doll and parade you around our family and friends. I remember the first time that I dressed him up. He looked like a dream. I got him a nice, cute blonde wig braided into pigtails. Then, I put on some doll makeup on him to emphasize his features. After that, I got him a school girl outfit to put on. Now my young one looks like the sissy that I have always wanted. She looked perfect and I brought her to the family gathering. Everyone told me about how cute she is and how they wish they had a daughter like her. You are so cute and girly. You even acted like a cute girl, giggling and having fun the whole time. You are the perfect little sissy and I’m going to dress you up everyday so that I can show how feminine you are. 

Sissy training phone sex with Mommy Penelope

Sissy training phone sex

Sissy training phone sex with sweet Mommy Penelope. Have you been wanting a sissy boy mommy to make you the best slut you can be with Sissy boy phone sex? There’s nothing I want more than a sweet little baby to call my own and treat like the cutest littles sissy slut imaginable!

Come right over here and crawl in Mommy’s lap sweetheart, let me show you just how much fun we can have together. Cuddling and treating you so sweetly, and so nicely while I give you all the love and kisses. That’s how you deserve to be treated, having you so close, rubbing your little sissy clitty.

The only thing I want you to do my little love is to come to make sweet sweet cummies for me while I play with you. Mommy Penelope has laid your pretty little sissy outfit out for you, and I’m ready to show you how good little sissy babies are supposed to be treated.

Sissy boy mommy

Halloween whore

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I love going to Halloween parties. My brother-in-law always throws the most significant lavish events anyone can imagine. I’ve had my eye on him and have to admit when my sister isn’t looking, I can see him staring at me, all hypnotized. So I told myself I would seduce him on Halloween and take his cock while my sister was clueless about what went down.

My sister is a cute young thing, and I’m much older. She’s barely in her 20s, and I’ve already graduated from the 40’s club. It’s weird to be compared to her because she will always be my young sister. I’ve got a daughter older than her.

Still deep inside, rooted in me, I wanted to fuck her new husband. This streak of jealousy in me makes me fuck other women’s men. Especially those close to me. After a few hours in, I began to get my wish. I had my brother-in-law all weak and horny, and I didn’t waste any time. Yes, I got all his

yummy cock and fulfilled my fantasies. Phone sex blogs usually have my hot stories of events that have happened to me, and I can’t wait to tell you all about what other escapades I get into.

Sissy Maid Training From Anal Sex Mommy

Since i am knocked up now I need much more help, i make my sissy boy do so many things for me. Prefect for Sissy maid training, he made sure to pick up after me and clean my messes even shave my Wet mommy pussy. 

Sissy maid training

One night I was so horny that two of my favorite bulls to come over and fuck me. They took turns fucking my mouth and cunt hole. I squirted a few times and they still had not busted yet. I decided to use my sissy boy, he will be perfect for a good bull nut milking. I called him and he was still wearing the sissy panties I gave him. I told him to help mommy out and milk her friends. Like a good sissy whore, he got on all fours and started sucking cock as I guided the other big black cock in his boy pussy. I’m an Anal sex mommy so I love watching a dick go deep in an asshole. He got fucked as mommy watched making sure he did a good job. One after the other my bull friends started cumming. My sissy boy tried to swallow every drop. All I could see was the cum dripping out of his sissy gapping asshole. Mommy made sure her sissy boy cleaned their cocks with his mouth before they went home. After that she went to sleep with her sissy son cleaning her cunt.

Best Big Sissy Boy Sister Ever!

Sissy boy mommy

 

When I decided to start sissy training my son, I didn’t know that being a sissy boy mommy would be so beneficial to the entire family.  I just thought it sounded like something fun to do with my gay little boy!  Ever since I sissified my son, not only did it turn him into a real daddy’s girl, but she’s been the best sister to my other daughters that a mother could ever want!

My femboy is my oldest so, of course, all of her younger siblings look up to her and she is an absolutely perfect big sister-bro.  When they want to dress up and try on her slutty clothes, she always makes sure to give them the least cum stained stuff she has to play with.  When it comes time to put on makeup, their sissy always shares her skankiest color palettes with her younger slutty sisters to be sure to bring out their true inner whores.  I’ve never been able to put on makeup as good as she does, I’m kind of jealous!

The funny part is watching her get turned on as the littler girls get naked and change.  Her girl-cock gets hard every time they all hang out so one, if not all of, her sisters is always happy to lend a hand and let her get her femboy family fuck on!  I love watching them, she works over those young teen holes and mouths just like her father.  Strong and commanding yet sweet and endearing, and always certain to make his fuck toy cum!

I love all of my girls but there’s something about your first born that will always hold a special place in your heart.  She has the perfect attitude as the eldest sibling, the perfect slutty style as my prettiest girl and the perfect cock that makes every pussy or ass it fucks have core quaking orgasms!

 

Sissy Christina Takes Vegas

sissy boy mommyMy dick eating sissy wants to get pimped out in Las Vegas & my Mami friends are so ready to play! Sissy Christina would do anything to have her hot pink snatch obliterated by a big black daddy. While we are away, Christina will be my sissy boy mommy bottom for the weekend. When we get to the strip, Christina will be wearing nothing but a neon green g string and a cheetah print tank top! I need everyone to know this bitch came to Vegas to make secrets and get creampied! When I introduce the ladies to my sissy they are going to want a pussy licking demo to see if she is worthy of getting Mandingo dick. As pedestrians walk by they’ll see 4a flock of big titty Latinas taking turns face fucking a little dick sissy! If her mouth works well, we will pull out our phones and dial up the black studs we use to fill our holes. Men are dogs so I’m sure they’d love their new fuck meat! Sissy Christina will finally get all the attention she desires when their multiple nigger dicks are slapping her in the face! These hung horses don’t have time to wait and will bombard her with all the dick she can take. When we are done with her she won’t be able to sit down for a week! 

Sissy Maid Training For Sissy Mommy Boy

Mommy was giving her son some sissy maid training.

Sissy maid training

When my boyfriend with a big black cock came over. He dragged mud on my floor from his boots and right away my sissy boy showed how he has been trained right and came out in his made outfit ready to clean. He bent over, exposing his crotchless sissy panties as he licked the mud of those boots. I pulled my great big mommy tits out and my boyfriend started sucking them. I signaled for my sissy boy to come over. I told him to be a good sissy slut for mommy and suck new daddy’s dick. He came over and I guided my boyfriend’s cock deep into my sissy boy’s mouth. Watching my son sucking his new daddy’s cock gave me a wet mommy pussy. I started fingering my cunt hard while watching but I wanted more. I pulled my son’s face off his new daddy’s cock and rubbed my ass on it. My boyfriend’s big black cock was wet and sloppy, he pushed it into my asshole. My sissy boy watches me be an Anal sex mommy. He loved watching mommy get fucked in her asshole by a big black cock. I grabbed my sissy boys face and pushed into my cunt as i got my asshole fucked. I came so hard my pussy squirted all over. That is when my boyfriend started filling my asshole with cum. My sissy maid son spent the rest of the night cleaning our cummy mess up.

Sissy training phone sex With Mommy

Sissy training phone sexYour mommy has a task for you baby. She wants to do Sissy training phone sex and for you to put on this cute little blue dress that she has on. I’ll take it off nice and slow for you, that way you can see all of your mommy’s body.

Good job sweetie! Oh, no, you can’t be talking that deep baby. You’re just a little girl! Train your voice more for mommy. Now mommy is going to cage your little cock and it’s going to stay on all day. A caged sissy, that’s what you are.

Mommy’s little pussyboy. Let’s get you your favorite wig now, baby. Oh! Aww, you’re already getting hard from this. My little sissy is so pathetic. It hurts? That’s because your caged baby. Now let mommy put on your favorite wig.

Look at how pretty my baby is for mommy! What a good boy. Try not to make a mess on mommy’s dress, honey. I know that you’re leaking pre-cum outside your cage. If it gets on the floor you have to lick it up. Hehe, I love training sissies.

They’re all so helpless and adorable. As your mommy I will make sure that you get the best training out there, and I will fulfill many desires from my sissy little girls. You’ll be a good girl for mommy, won’t you?

Scat family

wet mommy pussy

I heard some commotion come from my son’s room. I could hear him clearly saying that mommy’s pussy smells so good and how badly he wanted to fuck me.

I didn’t want to startle him, but he saw me, began to freak out, and profusely began apologizing. I smiled and told him its okay once I did that, it was like a switch flipped.

My son began to dominate me and tell me to bend over and smother him with my ass. I couldn’t believe what I was hearing, but I did as he commanded and let him lick and smell my ass juices. My boy’s cock was rock hard, and he wanted to pounce. He began to tell me to fart in his face. My god, what a request, but worse is I tried to fill his mouth with my farts. My boy kept telling me how much he loved the chocolate crusties.

That’s when his little sissy brother came in and disturbed us. He motioned me to get him to come over and make that sissy his bitch. I told my young son to bend over cause if he wanted to be a girl, he must follow orders. There went my oldest boy, and he began to do the same to my sissy baby.

The family affair wasn’t over till the house baby girl came over for her ass lick. My daughter came over, and he too began to pound her ass with his tongue.

The cherry on top was me giving him some soft chocolate serve. I made him come back to me and start over. He went wild, eating my ass and probing my asshole with his tongue. Mommy had Mexican food earlier, so I couldn’t contain myself and began shitting all over his mouth. He swallowed every bit.

Caught My Sissy Nephew Sucking Cock

I walked into my nephew sucking a cock. When they saw I was there they didn’t stop.

Sissy boy phone sex

His friend’s big black cock was ramming into my nephew’s mouth. It made my pussy twitch, and I grabbed my nephew’s head. Shoving it down, making him choke on his friend’s BBC. I pulled my big mommy tits out and made his friend nibble and suck on them it made me want to just get fucked. I pulled my panties down and told them to fuck me. As my nephew’s friend rubbed his cock on my wet mommy pussy hole my nephew was licking his asshole. It made his cock twitch inside me. I yelled for my nephew to lick his ass more and when he did, his friend pounded my cunt hard. I rubbed on my clit bouncing my pussy back on his young BBC. When I started cumming on his cock I felt him tighten up and then I knew he was about to fill me up with nut. My nephew noticed he was giving me a big creampie and pulled his friend’s cock out my cunt. He wanted to taste his friend’s nut. Since he wanted it so bad, I made him clean my cummy cunt like a good sissy maid.