Tag: 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

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.

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.

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?

Sissy Mom

sissy momPhone sex has always been a dirty pleasure of mine. I love talking to all kinds of men. I am a mature woman and a sweet mommy. I guess you could call me a nurturer and a caregiver. And you could call me a sissy mom too. It is my natural instinct to take care of you. When I met, Charlie, I knew he needed a mommy. He was an adult, but I could tell he had a secret. I whispered in his ear that I loved adult babies. His face lit up. I think I was the first to guess his secret and not shame him. He spent the night with me. I had a special surprise for him. I have an adult baby room. I babysit adult babies frequently, plus I have an ABDL nephew. I wanted Charlie to be himself. I gave him a bubble bath, then I fed him. I let him nurse on my mommy boobs. He suckled like he was fresh from my womb. I changed his diaper after he peed. He had some cummies in his diaper. That happens when breast feeding baby boys. Mommy’s cunt got wet. I enjoyed taking care of Charlie. He certainly enjoyed it too. He said it has been a decade since he could be himself in front of a woman. I hope I can make his next decade better.

Preggo Cumslut

preggo phone sex

My belly bouncing as I take that BBC deep in my cunt is all you see after a hard day’s work. My other brats are running around the bed as you best friend Michael is giving me all 10 inches of his cock and making me scream his name. Your dick is instantly hard, and you are angry and jealous of your pregnant wife getting fucked while you support her and her brats from previous affairs. But you know she craves that juicy big black nigger cock so much more than yours. After all you have an obsession with BBC porn yourself. It’s a wonder I don’t make you go on hormones and work the truck stops like my Friend Richard. The biggest Black cock Sissy I know! Now that’s the way a husband should be dealt with. Made to live as a woman, work his ass off and have to stay in his sissy room with all his pretty clothes, panties and stockings. But Richard loves every second, I wonder if the fact his wife is a BBC lover just like him is what he always needed. Now as for you, the choice to watch your lactating, heavily pregnant wife be fucked and jack off you little dick or to taste that chocolate cock, or even both, makes that little dick dance!

ABDL Phone sex Mommy

phone sex mommyI adore being a perverted ABDL phone sex mommy. I have the milky tits that are perfect for baby boys and girls that love being my littles. My teenage daughter tells me all the time that we need a new adult diaper lover to be a tiny little with her. Now she thinks in her blonde brain that all men with tiny pee-pees should be in diapers and have mommy’s tits to suck until they are ready to have a big fat meat stick pumped in those adult baby sissy cum dump mouths and/or ass holes. I asked her if she thought her little sisters would be good practice for our little sissy diaper lovers. My heathen teen slut said very bluntly if they can’t suck and get fucked by a big cock first then they can’t have the tiny cutie pies holes of her sisters. Don’t I train my offspring so well? Cum see if this mommy can satisfy your naughty ABDL needs tonight!

Mommy’s Sweet Little Sissy Boy

Sissy boy phone sexWith the house full and everyone stuck at home, it’s a lot harder for secrets to stay hidden from me. And my youngest boy has the sweetest little secret. Apparently, when mommy is away he likes to sneak into my room and dress up like me. Obviously my clothes are too big for him so for panties and bras, he sneaks some out of his sisters’ room. I found this out by waking up earlier than normal and found him in the guest bathroom modeling in front of the mirror. I gave him quite the scare and he quickly confessed everything to me. Apparently he is jealous of his sister being the only ones with pretty things, so I promised that as soon as we could, we would go have a shopping spree of our very own. Just for him so he can get pretty clothes in his own size and stop being a naughty little panty theft.