Category: Sissy boy phone sex

Periods and a sissy boy mommy

sissy boy mommy

Baby boy woke up to this sissy boy mommy having her period. As we all know when I have my period my baby boy has his too! I had a special surprise planned for him on this monthly though! I had saved my period blood up and mixed in some theatrical blood so it would go farther. As I rubbed my boys shoulders to wake him and told him that he needed to help mommy because she got her period. Oh he was so eager to clean up my early morning menstruations too! 

My boy went and got my Tampon and used his mouth to lovingly clean up mommy and even got a drink of piss for his efforts! He made mommy cum so much that I rode his face until I screamed!  I think the best thing is always when he tears open that tampax with his teeth and uses his mouth to push it up inside of my bloody mommy pussy! Then it was time for my boy to have his “period”. I loaded up a nice tampon with mommies menstrual blood and shoved it up that boy pussy! I made sure he had a few extras and a maxi pad for his panties before he went to school! Do you know why my boy gets a period? He is mommies sissy boy and I have a nice big fat dick waiting on him for when he cums home to help mommy with her period some more! Mommy had the biggest cock on teh block for some mommy son phone sex!

Using Nephew’s Big Cock

Fucking my young ones is not the only fun I have I fuck my sibling’s young ones too. My favorite is my brother’s youngest son, my nephew has a big cock surprisingly for such a young man.

Milf chat

The first time I saw it was when I walked in on him taking a piss. It caught me of guard and I just stared at it wondering how big it gets when it is hard. I had to find out, so one night when I stayed at their house I snuck into his room. He was sleeping so I slid my hand into his boxers and I stroked his cock trying to get it hard. My nephew woke up and was surprised to see me there. I told him to be a good boy for aunty and let me do what I wanted. I got his cock hard and slid my cunt right on it, I fucked him and used his big cock until I came on him hard. Making him my sissy boy sex toy. I squatted over his face and told him to clean auntie’s wet cunt. He lapped away at my pussy licking up all my juices. It felt so good and I was so relaxed I started pissing ion his mouth I heard his gargles but I didn’t stop. I told him to clean up and get in bed before anyone woke up.  

Surprised By My Kinky Sons

Mommy son phone sex

My cunt was pulsing and throbbing I needed to masturbate, I hurried home thinking about my big dildo I like fucking when I don’t have someone around. As I opened the door, I could hear moaning noises. I walked towards the back room where the moaning noises came from. I opened the door and I saw my youngest son on his knees with my oldest son’s big cock in his mouth. His head was back with his eye closed so they didn’t notice me there. My pussy was already turned on I lifted my skirt and started rubbing my clit. I rubbed it and fingered my cunt and let out a moan, it startled them and they both jumped up. I told my youngest son to keep going as I walked towards them, he did as I asked and I took my oldest son’s hand and put it right on my wet cunt. He started fingering my cunt as I watched my son getting head from his brother. He went deeper into my pussy as I saw his dick go further into his brother’s mouth. Then it happened I started squirting on his hand and face and that drove him over the top he started filling his brother’s mouth with hot gooey nut. I’ll make sure to come home early more often.  

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! 

ABDL Lactating phone sex

lactating phone Sex

I’m not one to brag but I have brought a boy to his knees with my tits. Thats why I am the perfect mommy for ABDL lactating phone sex. My tits leak when I see a lad in a diaper. Now even if you try to hide it I will still see that you are wearing a diaper under your clothes. I saw you in the grocery store looking at those Pampers crawlers. You snuck behind the pole in the Aisle and did a poopy! That’s right mommy Regina saw your face twist up and you let loose a stinky bowel movement. I thought to myself that This boy shouldn’t be buying his own diapers, where is his ABDL mommykins? I followed you to the check out as you counted out change. I asked if those Pampers were for you and you got so embarrassed and tried to run away. I paid for your butt wear and Tossed in a pack of wipes and some butt cream I had picked up. I knew you needed special attention, love. I caught up to you and told you I would bring you home. I tossed the diapers at you and put your bike in my Truck. You were helpless as I tossed you in the back seat of my extended cab and changed your ass right in the parking lot. You were so soggy and dirty. I decided right then to bring you to my house and made you call your own mommy. No one knew you were a secret diaper wearing ABDL lover. You mommy was surprised but said she would be ready to take care of your age play needs after the weekend I was going to have with you. I wish I would have found you sooner, because the way you latched onto my teet and let me play with your cocklette every time I changed your dirty poopy ass just made me so happy and wet. This is why every adult baby diaper man needs milky huge tits phone sex with mommykins!

Mommies Pee Pee Panty Boy!

preggo phone sex Johnny loves Preggo phone sex with a naughty dirty mommy!

He comes to me wearing his cute girly panties being mommy’s little dicked baby boy.

He wants to pee in my mouth and drink from my big milky momma tits. Johnny is just as nasty as Mommy Gabby! I drink his small pee pee’s golden nectar down like its soda.

Then he giggles and says “Mommy! I want to pee all over your big pregnant belly!” 

I tell him how absolutely filthy he is as he begins to spray me all over my tits and belly. He rubs it in like lotion and says he wants to ride my belly now. Dirty Johnny! Well that means he wants to get on top and pump , pump, pump mommies pregnant pussy!

So I let him slip and slide as I reached back as far as I possibly can and put a finger in his little boy butt! “Is it okay mommy if I give you my cummies!!??”  he squeals when he is almost there! Of course it is mommies little anty wearing pee boy! I am your preggo mommy whore after all!

Pump. Pump. Pump! 

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!

Training With Mommy

Phone Sex MommyMommy has been touching herself all day thinking about the dirty and naughty things to do with you! I think you need some extra training before I let you get fucked and before you can taste your sweet mommy pussy again. Start jacking off that pretty little cock you have! So small it could be a clit for my little sissy boy! Your mommy loves playing with you! I need to feel and see you get hard while you rub off and I’m sticking toy after to into your sissy boy ass hole. Come play with your unforgiving mommy and let’s see how much more naughty and dirty fun we can have while you become mommy’s little fuck toy baby!

Indulging Mom Fantasies with My Son

Mom fantasies Not one to ever deny a boy’s mom fantasies, I think it’s important to let you in on my dirty life! As a Stepmom with a son whose birthday falls close to mine, I decided to take him out for a treat. A vacation away from daily life and a cheating husband. I decided why not spend his money on a mom and son fuck than at a nice resort! I’m talking manicures, pedicures, facials and mud baths. My step son and I have been fucking for a while behind his fathers back, so a fancy dinner and a big California king bed soon called our name.


I hop in shower with my step son and he pees on my legs. That gets this mommy angry so I lay him back and tell him, Let me give you a real shower, a nice golden shower! Now we have to get clean all over again and we soap each other up and start French kissing. I’m too horny to deny him and his cock! I dry off and go back to the bed , “close your eyes, don’t open them until I’m ready.” (wearing a black garter belt and black fishnets and black stilettos cup less bras lifting my tits ) I grab hold of step son’s dick, and put us in a 69 position. Can you imagine my beautiful pussy in his face as Mommy sucks her step son off? He loves my pussy and I love being his cock sucking mommy. I love the way he sucks my clit grabbing it between his lips and pulling until I drench his young face!

Now I have a surprise for him! “Close your eyes ! Get up! Okay baby boy now open them!” I am holding a real doe work inside me, my cock standing straight up “mommies got a stiffy!” Do I make you a hard mommy?” He babbles at me as he is ready for mommies Big hard-on. I pull his legs up after he sucks it to get it all lubed and I fuck my step son with his legs up and fucking him on his back, my tits bouncing on his chest until he gives me those cummies I so desperately want form him as his sissy bot mommy!

Mommy Son Phone Sex in Pantyhose

mommy son phone sexMommy son phone sex is what I love most. I am a sweet nurturing mommy, but I have a mean mommy side too. Maybe not so much mean as dominate. One of my sons is bisexual. He is my middle son. He loves fucking his mother. But he also loves wearing my sexy lingerie and getting pegged in the ass. I know it is not for all men. I have two very straight boys. I love all my sons equally. And if one of my boys needs mommy to put on a strap-on, I will do that for him. A mother’s love knows no bounds. I am a mother who truly has no limits. My middle boy came for a visit last night. Sometimes he wants to fuck me. And sometimes, he wants me to fuck him. It was that kind of mood last night. I can be a mommy slut and a sissy mom to my son. I took him into my room to try on some of my pretty things. Now that the state is back open, I am making the best of shopping. I went to Victoria Secret this week and spent close to a grand on pretty underthings for me and my special son. I am an old school mommy. I still wear stockings and pantyhose. I like to have matching bras and panties. I adore corsets, garters and baby doll nightgowns too. My boy loves to wear my pantyhose. Do you like pantyhose? There is no shame in admitting that you do. They feel very silky against your package, tiny or big! My son has an 8-inch cock, but he still loves to put on my pretty panties. I dressed him up last night and pegged his ass for hours. He came all over my pantyhose. I can peg your ass too if you need a sissy boy mommy.