Category Archive: Sissy boy mommy

Sissy Training Phone sex With Mommy Regina

sissy training phone sexYou know what time it is! Sissy Training phone sex Mommy sessions! Now what I like about being a sissy mommy is that I can educate you on all things necessary to be a good sissy boi! That’s right, mommy has a few things up her sleeve and is a Jane of all trades. I adore sissy men. Especially those who know what they are. Your bald pink cock is so adorable and I want to make sure you know just how to be a sissy slut for me. Your sweet little dick tucked in satin panties and hidden under a cute little dress. I will make sure you go through all things female. I am your educator and confident. I will teach you how to have your period, how to take a nice big dick and be the prettiest little sissy ever. My goal in being a sissy boy mommy is to make sure that you are submissive and on your best behavior. My pussy is ready for your mouth and My boyfriends are ready for your sweet girly ass. It’s not your fault you have a small dickie, but we can make you into a perfect play toy! Step into mommie regina’s classroom and learn how to please me. Maybe later we can do a sissy show and tell!Sissy Boy Mommy

Horny Phone Sex Mommy

phone sex mommy

I don’t like to brag, but I’m the best phone sex mommy you could ever ask for. I am loving, understanding, and I am the kinkiest bitch you could ever hope to meet. I always say that anyone is welcome to call me for some family fun, and that will always be the case. Fantasies are amazing, but if you’ve done something with your mommy for real, I would LOVE to talk to you today. There’s just something about boys who are unashamed of their love for their mothers that really gets me turned on.

So, tell me – did you seduce her or was your fun all her idea? Maybe she caught you watching her masturbate and told you to come in and help her. Or perhaps she caught you jerking off and from the things you were saying, it was clear that you were fantasizing about her.  You didn’t know dreams like that could come true, but she showed you thar they could. Which one of her holes did you get to stick your dick in first? Did you get to cum inside her? Tell me all about it when you call me. Maybe I can even be your mommy for a while.

Sunday Night Bed time Stories with Gia: Pinnochio

Preggo phone sexOnce upon a time there was a slutty little breeding whore named Gia. She was the dirtiest little whore in all the land!

One day she met a boy and he seemed sad. She asked him what the problem was and he looked down at the floor and said, “Gia, I have a small penis and no one will fuck me and I will never be a real boy!”

Gia started to get all wet in her furry little kitty because she knew she was going to make him a real boy!

She reached down and started stroking his wood. She kept stroking it and stroking it but nothing was happening. Then she got an idea!

She bent over in front of the puny penis puppet and showed him her dripping wet kitty! He got so excited that his big nose grew bigger and bigger! This made our slutty breeding whore very excited and the young boy couldn’t wait to burry his nose in her pussy!

She told him to come closer and when he did, she pinned him down and sat right on his face, forcing his giant nose deep in her ass!

His nose was buried so far in her ass as he licked and nibbled at her sweet young pussy! He wiggled and struggled beneath her as she smothered his face, grinding down on his nose!

Just then she heard a huge pop! She looked down and saw the biggest wood she had ever laid eyes on! He had built up so much pressure that his hard as oak fuck stick just popped right out!

Gia was so excited as she took ever inch of that carved rod into her swollen cunt. She squirted over and over again and the more she came, the bigger that log grew…..everyone knows wet wood swells!

And they fucked for hours happily ever after!

Join us next Sunday for Alladin’s Magic Carpet Ride!

 

Period Slave To His Mommy Whore and Auntie Whore

Mommy whore

This Mommy whore has a period slave for a son. It was my pleasure to introduce my sister the very Hot Milf Eva, to his secret duties yesterday.  See whenever I have my period my son cleans his mommy up and does all the things a woman on her period needs done. He is a very dutiful and passionate slave!  What you may ask, read on..

Eva was over at my house as my son was getting out of soccer practice. She had started a very heavy menstrual cycle and was complaining of her symptoms. She needed an orgasm and stat! I knew just what would make Eva better and My son so happy and hard! 

I made mommies boy Robbie hurry to shower when he got home, making sure he only kept his towel on! He questioned but did as he was told, always good in a slave. I laid some old towels down on the couch Eva looked perplexed. When Robbie was right in front of us, I spilled the beans. My son was going to clean her pussy up! Eva took off her skirt and pulled down her black panties. Spread-eagled on the couch My period slave of a son went to work cleaning every last drop of her bloody heavy flow right up. He even removed her tampon with his teeth. And like most women, myself included Eva was trying not to pee as her tampon was removed. But I encouraged her to piss right in his mouth. Now Eva Pushed his head deep in her bloody wet mommy pussy and gushed all over that boy’s face.

I had never been so proud as he unwrapped a super-plus tampon and made sure the sting and angle was perfect. And yes he used his teeth to insert it! I was so proud that after he repeated with my own period cunt, I had to rush and get my Handy dandy strap-on! Eva Had taken full advantage of the situation and was in a hot 69 sucking his very hard cock and inserting a tampon in and out of his back door pussy. I forgot to mention when mommy is on her period so is he! It was so fucking hot with my tampon string hanging down and Eva Riding his face with her plugged pussy that we made his dick shoot straight up in the air! It was all over us! Cum to Eva and Me if you need any type of mommy phone sex period lessons!mommy phone sex

From Son To Sofia A Sissy Boy Phone Sex Transformation

sissy boy phone sex

My son asked to become Sophia recently and this is his sissy phone sex story.

“Don’t forget what mommy shows you. You’re going to have to impress daddy if you want to be a female.” I grinned at my boy who was transforming into a princess. It had been a week since he asked to become mommys girl. I had quite the feat finding clothes and panties and even cute high heels for him. We had trained in the ways a girl walks and all the other fine femme things.  I know you’re dying to know how else I trained him! I started slow with my handy dandy Jesse Jane strap-on. A little slobbering on the end and a few gagging sessions had me convinced he was ready. I had him taste his daddies cum from my mommy cunt every morning. I would 69 him, (excuse me her) and suck that clitty so pleasure would be associated with the taste of daddy cum! 

And now it was time for this sissy by mommy to Introduce Sophia to daddy for her final test at being female! Oh, Daddy was pensive, after all he was going to have another beautiful female to fuck. I purposefully left out the part where Sophia’s ass would become her pretty pink pussy. 

After a good cocksucking session I was impressed but as daddy looked at me I knew it was time. I brought Sophia across the bed and pulled her red panties down. She tried to buck away as I spread ass cheeks so daddys big cock could force fuck her brand new tight pussy! Watching My Sissy girl moan and beg daddy not too had me so wet. I spit on sissy sophia’s ass and helped guide that cock deep in her tight ass pussy. It wasn’t long before she was giving us spurts of cum from her clit.

 If you need that first jump into sissydom this phone sex mommy can help you.

Horny and So Pregnant for mommies boy

pregnant phone sex

Mommy was oiling up her big belly when you came and put your arms around it and gave your little sister a kiss. I give you a big drippy drink of my lactating tits and you hum as you suckle. I tell you that soon you need to share your milk, and you get a frowny face. Oh but my sweet Angel face mommy has something creamy for you between her legs! I push your head down and lay back on the bed, I make sure you eat your cummy yum yums, but tell you to leave a little for lubrication! Now climb up here and hold on to your sister in my belly. Put that boy cock in me and rock back and forth on this waterbed belly! Did you enjoy mommies boyfriends cum yums? Yeah baby hold on as she kicks she loves when you fuck your own preggo mommy! You feel your dickie go squash in that left over load. Now where are you pretty panties I bought you. After you give me squirts you put on your panties and do a dance and show me that beautiful boy ass as you finger it! Way to go my sexy bad little boy. You and sissy will have so much fun as mommies slutkin pets!

Hot Sissy Boy Mommy

sissy boy mommy

I didn’t mean to become a sissy boy mom. It just happens when you enjoy molesting boys and girls in the same way. Tight holes meant to be filled. Filled with my fingers , a cock, a strap on and the best Cum loads! I enjoy older P-men using sissy boy ass. Girls are supposed to be soft and sweet little daddy’s playthings. But a boy turning into a faggy man slut because he was ass fucked. That shit is the hottest to this mommy. I have one sissy boy who will probably be the biggest cock sucker, taking hundreds of cocks by the time he is done with college. And  have one boy who enjoys being the top. The bottom feeding men need him and his donkey dick shoved up their little tight intestines. He loves fucking mommy pussy and making his brother his clean up bitch. I love squishing out a big load of hot man cum from my ass and pussy into his queer little face. Oh I coddle him after, I am not that mean, these milky momma breasts are full of love for my mommys boy! But at the end of the day I love a good P-man and young cock. If he has to pay for mommies fetishes that’s the way it needs to be. It doesn’t matter if you are a hot P-man, or a sissy boy, mommy will be here for you! Cum and jack off with mommy Regina.

Phone Sex Mommy Blakely

phone sex mommy

If you have talked to me before, then you already know I love being a phone sex mommy. But if you don’t know me, then hello! I’m Blakely and I LOVE talking about your fantasies that revolve around fucking your mom. Hell, I have had fantasies about fucking my own sons (and maybe I’ve even done it – I’ll tell you later) and it turns me on to tell you about all of that. Maybe we can even come up with some really dirty mommy and son fantasies together. I think this goes without saying, but I don’t have any limits, so we can do anything you want to do.

I’ve always dreamed about being the first women to fuck my sons. I wasn’t, but the thought of it has gotten me through many long and lonely nights. Just me, my vibrator, and my dirty thoughts. But it would have made me so happy to be able to be the woman to first put my mouth on those young cocks. The first woman to spread her legs and have their teenage cocks slide inside me. Do you want to hear more about what I’d love to do to them? Call me and maybe you can stand in for my son and get this mommy pussy.

Jack off with mommy During Strap-on play

jack off with mommy

I have been told I am the most well hung mommy in the neighborhood. That is because I give it good with my strap-on as my younger son likes to jack off for mommy. I am a domesticated MILF with a wild side. I believe that every young man who is effeminate should try my cock.  I know that he loves watching me fuck his brother and stroke his little dinky. It just turns me on so much to cum on my son’s big hard cock, while my little one gets off on it. I made him a mommy and brother sandwich today! Him on my fake dick and sucking his brothers big dick.  I just love the extreme differences in those cocks. I have my cute little sissy boy and my well hung manly son both right here for me every day. My well hung son gets all the mommy pussy he can handle and even my ass when he needs something tighter. He is way to big to fuck his little sisters. But that’s okay I have a small feel-doe that I out up in my pussy to fuck tiny twats. That does not mean my sissy son and girls don’t suck big brother off! Little mouths in training to be good cock suckers. And when we are all tuckered out form fucking I read them a bed time story and let them drink my hot warm milk. I even kiss cunny and dickies before they go night night. I love being very good p mommy slut who always puts her brats first. I might even be a mommy deviant! Big cock, small sissy cock, and tiny twats are all I ever think about. Every man should have a dirty mommy phone sex hottie like me to jack off too!

mommy phone sex

Mommies Period Boy! ( Nasty Milf Phone sex )

Milf Phone Sex

Your milf phone sex whore is a nasty slut. I love to train my boys to serve the most basic of women’s needs. That is him dealing with mommies period for me. That’s right I make my son clean mommy’s pussy and change her tampons for her. He crawls between my legs and removes my bloody tampon with his teeth. It is such a sensual experience to have him slurp and lick me until I am completely clean. Unfortunately for him mommy is bleeding heavy and needs a super plus tampon today. I prefer the Kotex sport and I make him get it and crawl back with the new tampon between his lips. Now he needs to spread my pussy lips and insert that fresh tampon right up inside me. We like the ease of the cardboard applicators and with a kiss to my pussy he shoves that applicator up and straightens my string out.

On days like this I need my son every three hours and sometimes before that. When he goes to school I time my changing so I have a very full tampon of mommy blood and a slightly messy pussy for him to clean. Recently your nasty mommy phone sex slut has been making him due the duty of understanding just how much a woman goes through. My period clean up boy gets his very own tampon, to go to school in. Normally its a clean one and he has to text me when he changes it. But here at home I do something even a little more extreme. I make him wear my used messy one around her. I want my perfect sissy slave son to know somewhat what it feels like to be a woman. It is more than having a tiny clit stick, he needs to experience the period with mommy! 

Don’t you want to please your perfect mommy too baby?

Older posts «