Category: Sissy training phone sex

Sissy Boy Mommy Slut

sissy boy mommy

Halloween is the best time in the world to be a sissy boy mommy. I love dressing my babies in the cutest little outfits. This year, I am making one of my sissies go as sexy baby yoda. Can you even imagine how fucking adorable that will be? But it’s not just cutesty outfits that my little ones are going to be wearing. You know that there are going to be some sissy boys who are all dressed up like nasty little whores. One of them is going as a sexy nun and she’ll be blessing every fucking cock she comes across.

If you walked into a party and a nun is down on her knees sucking dick while her asshole is getting pounded by a big black cock, you’d probably get really excited, wouldn’t you? I think you’d be hard pressed to not want to walk over to her and tell her that you want to sin. But if you can think of another sexy little outfit you’d want your cock sucker to be wearing, call me and tell me all about it. I’ll make sure to get one of my sissy babies down on her knees faster than you can even imagine!

He eats Wet Mommy Pussy

wet mommy pussy“You know mommy loves you right?” I told my little son as he was eating my wet mommy pussy. He moaned and whispered he loved me too. “You taste so good mommy, I never want to stop!”
I squeezed my legs tight and trapped his little head as I began to orgasm on his face! He squirmed and wiggled and tried to get away, I couldn’t help myself, it was involuntary and as I finally released he was mad at me!
“Oh pookie bear momma is sorry, it just felt so good! Come here and let momma nurse you and play with your weewee.” My big boy jumped up in my lap and began sucking and that just made me horny all over again! I knew I would have to get my big vibrator out and fuck myself as I nursed. I switched it on and began playing with my already tender clit. My son popped a nipple out of his mouth and asked if my toy felt good. “You want to see?” I said as I began teasing his little weewee. He giggled and squealed as mommy had a devilish idea! I teased that little booty hole until I popped the head in and he cried out, “Ohhhh Mommy! Don’t stop! I love you mom, It feels so good!”
This sissy boy mommy loves you too, sugar ass!

P-Momma Has Yummy Juices

This p-mommy loves playing with her little man, I love when he crawls in my bed and wants to cuddle. I stick my hand in his pants and play with hi tiny ball peepee and his little pink balls while I rub my hard clit.

Sissy boy phone sex

You know mommy likes and gets excited when you suck on mommy’s clit like a lollipop. I’m a nasty perverted p-mommy so I have made sure to show you how to use your little hard peepee to rub on momma’s clit. When I’m ready I get your mouth right on my wet cunt hole and I squirt right in your mouth, making you take very last drop of mommy’s wet pussy. I even use you as my toilet and give you my warm golden juice. Sometimes I make you drinking it and sometimes I give you a golden shower. Momma loves how much you enjoy my hot wet messy juices. 

Mommy Whore Eva Is Back!

The best kind of mommy whore is one with no limits. Yes, I am back after my Summer Vacation! I was a complete fucking tramp and loved every second of it. But i have missed my wonderful lovers here and to some I spoke with before leaving I promised I would be back! So, yes guys mommy is back!

Now I need to give the back story for any new guys here! You see my son has a great fucking time being my cucky. Yes, that’s right, I let my son join me when I am taking that bull cock. He used to spy on me and jerk off. I caught him one time and my lover thought it was the funniest thing. It was really his idea. He said to me, “let’s make him a mommy pussy licker and cock sucking bitch boy”. I loved the idea and my son soon became aroused at the situation. He truly was and still is a mommy’s boy. I have had him fucking my sloppy cunt, cleaning up the creampie and even sucking my pussy off of some big bull cocked lovers of mine.

Mommy whore

How it started was like this. We invited him in the room and to position himself under me. You know sixty-nine only with him  not getting his cock sucked. Nope, he cleaned my mommy creampied pussy. Not only did he clean the cum from my cunt but he also sucked my cunt juices from that bull cock lover. Eventually after some fun we got into dressing him up in stockings, panties and even a bra. Sometimes he would even wear a wig. Every time he sucked a cock though we make his lips a sexy whore shade of red! Now doesn’t that sound like a thing only a naughty mommy would do?

Fuck a preggo belly button

pregnant phone sexYou would think my little boy who loves panties would want nothing more than some mommy cunt. wrong his little tiny penis is content to fuck mommies belly button. And you know that leaves that panty clad ass in a prime position for some ass fucking by his brother. I always tell him its okay baby, make some yummy cummies in my pregnant belly button, while mommy lets him fuck your little pink puckered poop shoot! I have to coo and tell baby boy Jon Jon that mommy likes it when he gets fucked in the ass and he makes a big pool of cum right in my very deep belly button hole! 

Of course my older son gets his rocks off in Jon Jon’s ass and I have my ass fucked little man sit on my face so I can clean it all out! I shove his little sisters panties in my wet cunt and tell him to go up inside me and fish them out with his mouth! I never said I wasn’t a filthy skank of a mommy. 

Sissy Boy Mommy And BBC

sissy boy mommyAs a sissy boy mommy I know all about the wants and desires of men who desire to transform into beautiful women. Women who were once classified as men who need a big black man to bring out the woman in them. I, as a Cis gendered female love BBC and am not shy about my experiences and often share dick with my own sissy sons. SO it cums as no surprise that I am a promoter of transgender rights and sexual experiences. I just had the most beautiful experience with Sissie TJ who is an older Trans woman who gave me some websites for those that are curious questioning and Queer oriented. We talked about my son’s transformation into a full time woman and the love of a big black cock. We talked about things like the Esprit conference and the first transgender surgeon who specializes in trans surgeries. So if your closeted or curious about a big black dick in your back door pussy. And anything in between just know that this mommy is very inclusive! And filthy! Let me help you be the sissy or trans female you were meant to be. Even if its just here with me so you can cum! 

My boy is a man

wet mommy pussy

It is my boy’s big 18th! Yes, he’s legal and ready to have some of this wet mommy pussy. I have counted down for this day for a while now. I can’t wait to show him what it means to be a man. My boy is handsome, and he has quite the big cock. Mommy is going to devour it and make it cream. My mouth on his cock makes me wet as can be, and It’s time you learn how to please mommy with your tongue and your cock. You are one lucky boy to be able to have such a hot mom that’s willing to treat you this way. All your friends have always wanted to fuck me. Now you can brag about the nasty incest mommy you have and indulge in all your dirty fantasies with me.

Panty Thief!

sissy boy mommyAs a sissy boy mommy I know all about panty thieves! My boys tell me about their first-time playing with mom’s or sister’s panties. Stealing from the laundry room, hampers and right out of drawers and closets! It all started with a deep inhale of that musty pussy and ass. Cocks hard as they stroked with dirty panties and then it happened! They tell mommy of their curiosity about the feeling of silk panties on their sissy cocks. So they would of course try them to realize that they felt soft and good. The moment the fabric caressed that cock it got hard. Family panties and Wife panties are the norm for my cross dressers. They even go so far as to sneak into a neighbor’s house to steal her dirty under things from her. Clean or dirty would do; just any random pair really. Sometimes they are even caught! That’s my favorite part! My dirty boys tell me when they began to wear undies, and how they cant stop now! My panty wearers put them under their nice suits, to the bar and even to Sunday school. I know of a couple of boys who wear panties constantly, and it’s getting worse each day: adding a bra, stockings, or pantyhose along with a garter belt. As an anal sex mommy; I know just what is coming next for these “men”. I tell them to buy a butt plug, bullet, or vibrating dildo! Get dressed in their slutty lingerie for me. Let me transform them into the town’s best cock-sucking sissy. Can you dress like the perfect slut? Let me get you all dolled up with a bright red lipstick for Mommy Regina!

Sissy Boy Mommy Wants to Play

sissy boy mommy

Oh, I just love being a sissy boy mommy. When my son was younger, I walked into my bedroom one day and caught him wearing my panties and jerking off. He was embarrassed for some reason, even though I’d been playing sexually with him and his siblings for a long time. I told him he had no reason to be shy and that if he wanted, I would help him get dressed up in more than just panties. He reluctantly agreed and we went into my closet to find some lingerie and a nice dress for him to put on.

After he was all dressed up, he asked me if I would get my strap-on cock and fuck him. I was SO happy because I’d been hoping that one of my sons would be into that! I told him to bend over and I squirted some lube on his pussy and started to slide inside him. I got so excited that I reached down to touch my pussy and came almost instantly. Do you want to hear more about the things I did with my sissy son? Call me and I’ll tell you how I pimped him out to all of my male friends with enormous cocks.

Sissy Maid Training Mommy

Sissy Maid Training

I’m a slutty, slutty mommy who believes in sissy maid training for my sons to be disciplined for me. It makes me so happy when I have the opportunity to transform my sweet sons into little  sissies who cater to their mother’s every whim. My baby boy’s clitty is absolutely darling, and dressing him up in adorable frilly dresses with matching stockings, panties, and training bras is just too much fun! To make me happy, he said he wanted to do anything, so today he is my little maid and I can play with him however I please.

It’s the most adorable little French maid ensemble I’ve ever seen. He looked exquisite in his short skirt and thigh-high white stockings. I had ordered him to draw me a nice warm bubble bath, and since he was such a good boy, I let him wash my huge milky tits as well. Next, he proceeded to take care of Mommy’s hair. It felt really nice to be pampered by my son in his sissy outfit. Now that he did such a good job of taking care of me, I allowed him to enjoy himself after I had finished drying off. Until he came right in his panties, I rubbed his little peter through his sissy slut panties. Now for step two of Sissy boy phone sex with mommy Regina, Finding a cock to train him on, Mommy does have a nice big strap on to help open up that ass.