Tag: sissy mom

Anal sex mommy loves cummies deep inside her brown eye

Anal sex mommyMy life can be summed up by calling me an Anal sex mommy. My ass is perfect for catching big thick creamy loads. As I tell my slutkins, ass play is a natural part of life and it feels so good to be opened up. Do not be shy when you come see mommy regina, I like it up my ass and it’s okay if you do too. But even if you don’t want a finger or tongue up that beautiful asshole, mommies are available for use! 

Although I do love when my brats get tied up to a pole and that as sis creamed with Peanut butter for some very naughty roleplays! I digress, all This sexy Milf wants you to know is that I love butt fucking in every situation.   So come on down and let me show you how much I love a good ass pounding.

Anal sex mommy loves your cum in her shit hole!

Pull aside my black panties and look at mommys tight little ass pucker. You may give it a kiss or just lube it up with my honey. I sure will suck you hard and ride your cock a little before you push in my brown eye.  Mommy wants to hear your moans and feel your pleasure as I slide up and down your shaft. I’ll be sure to cum with you, and then we can do it all over again.

Jack off to my Horny milf pictures and feel yourself slipping in this milfs ass! Doenst that feels so fucking good as i moan and cry out how good your cock feels inside my shit hole. Bend me over an take what you want right now, Mommy Regina is waiting for you. 

Fuck a Milfs ass hole and let loose all that yummy cummy!

mommy Regina is your anal cum dump!

Anal sex mommy has a sissy slut following in my footsteps

Anal sex mommyAn Anal sex mommy like me has an addiction to being an anal whore… Such an addiction I just so happened to rub off on my son! He loves getting his pussy fisted and I found out for the first time when I walked in on him fucking himself with my dildo. He thought he would be in trouble so I had to promise him that I wouldn’t tell his father. If his father ever found out our son was a sissy he would have probably beat the brakes off of him… Luckily, he didn’t find out until my son was well overage! My boy showed up for our Christmas dinner this year with his cock inverted and a set of double-D implants. My husband’s jaw nearly fell off his face but it was too late to shame our boy for his faggot ways.

Being a Sissy mom has always been such a fun adventure for me.

My boy or shall I say girl and I have taken on many cocks together. I mean, after all, he wanted me to keep his dirty secret and well I used that as an excuse for him to keep mine. I taught him how to suck and fuck, all those tricks my boy does, he got from his mommy. I was the reason for his first anal fuck! One of my tricks was over and well he wanted a piece of my son’s tight ass. I without a doubt put him up for the offer… I got myself an extra wad of cash on top of our original pay. My son had no idea his cunt was paid for and still doesn’t until this day. I sat back and whipped my clitoris as I watched my boy get his mangina stretched by a real cock for the first time!

My Wet mommy pussy was filled with a hot load after he got through popping my boy’s cherry and I must say it was one of mommy’s best fucks ever.

Sissy boy mommy Tina enjoys turning stray boys into sissies

Sissy boy mommy I am a Sissy boy mommy! My boy loves being pegged… He gets so excited when I bring horny men home with Big black cocks to share with him. I found out about his sissy ways one day after catching him prancing the house in my used panties. He wanted his fresh little clit to smell just like momma’s pussy. That’s when we dug deeper into exploring his sexuality! I introduced him to my sex dungeon and all of my toys… He confessed to fondling his asshole using his fingers… But I told him I had something much bigger and better than that. I slipped into my self-thrusting strap-on dildo and had him gag and drool all over my sex toy.

This was only the beginning of Sissy maid training, he was soon dressed in lace daily and left to do all the womanly duties around the house.

This was how he earned his next serving of creamy cum! His behavior depended on his serving, whenever he was a naughty sissy slut. I tease him with my drooling cum filled cunt; while telling him how good it felt to have my pussy stretched. He is to then get down on his knees and I instruct him to give momma a cum clean up. When he is on his best behavior I always make sure to bring home a nice meaty big black cock. His feminized moans always let me know how thankful he is to be able to serve his newest daddy. Being a Sissy mom is the best thing that has ever happened to me!

Wet mommy pussy tastes so delicious!

Wet mommy pussy

Wet mommy pussy tastes so delicious! I’m horny mommy and proud sissy trainer! I’m here to show you all the fun and wild ways to find ultimate sissy pleasure. Whether you’re in it for the pleasure or for the humiliation, it’s a delicious experience! I’m 100% confident that I can provide you with that, baby!

I pride myself on being an expansive, no-holds-barred teacher in sissy training. I know all the tricks and I’m not afraid to go all out. You need to get the most out of your experience. I love to be creative and make sure that there’s always something new and fun to try out every session. My goal is to help you discover a part of yourself that you never knew existed.

Let this Sissy mom show you how to really use the tools of the trade to properly suck, lick, and fuck until you can’t take it anymore. Not only that, but I also take pleasure in teaching you how to properly take cock like a true sissy, so that you can experience the full range of pleasure that sissy training has to offer.

I can guarantee that you’ll be truly aroused, and perhaps even a bit ashamed of your own debauchery, after you’ve gone through a session with me. With my help, you can feel secure in knowing that you’re making the best of your sissy fantasies and desires.

All in all, I’m here for you, sissy. Say my name and call me to book your next session for some of the hottest sissy training around. Just think of all the amazing cum that will ooze out of your pussy hole after a few hours of my unique style of training. Cum-draining orgasms and fulfillment await. So come on over and let mommy Ireland show you who’s boss. Call for Sissy training phone sex!

 

Huge tits phone sex Mommy Loves Gay Pee-pees

Huge tits phone sex

Huge tits phone sex Mommy Loves Gay Pee-pees!  As a mommy piggy whore I understand why men sometimes love cock. I’m stroking my wet milf pussy to a gay peepee with a dildo in his faggot fuckhole!  I’m such a dirty piggy whore! I love cock and cum so much! I want your gay peepee to blow for cock now! Listen up I have major skills with strap-on fucking and consider myself a peg queen. I would make a mommy sandwich out of you with one of my son’s big cocks. Go ahead and get dressed up with me and a nice big fat tranny cock. I love the stories my men tell me of cock sucking cum eating fags. 

Huge tits phone sex for sissy fag pee pees

Anal sex mommy Regina is a fag hag and I love my gay boys sharing cock with me. Even better when Mommy can dress them up first to be her sissy slave! Men who are exploring taht bi-curious side need a Hot milf to show them even if you have a big fag pole you can still have fun with other big cocks. So get ready to look like a pin-up bitch and get that mouth and ass pussy used up when we have some sexy fun together.

 I want you to feel my strap-on deep inside you. I want to explore every inch of your tight ass.  Let me hear you moan as I fuck you harder and harder. Beg for more. The hottest is you screaming my name as I fuck you into oblivion.

I’m waiting for you to come and explore your bi-curious side with me. Let’s have some amazing fun together. I’m ready to welcome you with open arms right into these big tits.  I’m an experienced Sissy mom and I know just how to drive you crazy with cock. Mommy iswaiting for you to come and explore your pegging side with me. What are you waiting for I’m strapped and ready.

 

Sissy boy mommy Ireland is going to pimp out your pussy!

Sissy boy mommy

Sissy boy mommy Ireland is going to pimp out your pussy!  I’m your mommy and I’m here to make sure you’re the most perfect sissy slut you can be. I’m going to dress you in the softest, silkiest, lacy panties and ensure your little clitty is tightly caged. Everyone will gasp when they see how cute my sissy slut looks in her pink dress and pretty face as if I had created my own little China doll.

I want you to adapt to the role perfectly, so I’m going to teach you everything there is to know about being a sissy breeding whore. There’s no need to worry, I’m here to take you each step of the way. First, I will take you to a group of select men of my choosing, they will be ready and waiting for you. You will have to take on one cock at a time. Show each man what a filthy little whore you are! They will fuck your face so hard, all that pretty little make up will be smudged. I think you would look absolutely adorable!

I’m sure you’ll become an expert slut in no time. After all, I’m not just teaching you how to be my little sissy slut, I’m teaching you how to be everyone’s sissy slut. Once you’re fully trained, you’ll be able to take orders from any man. If it’s humiliation, BDSM, or forced feminization men love, your sissy slutty training will turn you into a sex toy they can’t resist.

Most sissies complain about how hard it is to be the perfect slut. That’s where I come in. I will keep you on track with daily sissy lessons. We’ll role play, talk about the kinds of humiliating attire and spicy punishments that make them weak in the knees. Before long, you’ll just have to show off what you learn and they’ll be obsessed. So, are you ready to answer your mommy’s call and become the best sissy slut you can be? I think so!

Sissy Boy Mommy Nicolette Loves Playing with Femboys

sissy boy mommyI find being a sissy boy mommy rewarding. None of my sons grew up to be sissy boys. However, they all have friends who enjoy feminization and other sissy boy things. And guess what? I enjoy encouraging these boys to be themselves. Nothing wrong with wearing mommy’s panties and sucking cock if that is what you want.

Instead of one of my sons bringing me a sissy boy this time, my husband did. His best friend from college is a lowkey sissy boy, but his wife will not indulge that side of him. Sadly, I hear that from my callers too. Well, that is why I am open to helping sissy boys like Tyler. I can be any boy’s sissy mom on or off the phone. Tyler’s wife even gave her permission for us to have some fantasy playtime. So, we ran with it.

Tyler saw my sissy wardrobe and he looked like Charlie when he first entered Willy Wonka’s candy factory. I mean this boy looked amazed. His eyes were as wide as the sky. I encouraged him to feel everything and wear what he wanted. He put on this lace catsuit I own and blossomed into a pretty girl. Do you know what happens to sissy boys when they put on something sexy like that? They transform. And they crave cock.

Sissy Training Mommy Helps You Suck Cock

Now that Tyler looked more like a Taylor, I needed to find some cock. I love my husband, but he never wants a male sucking his cock. I doubted he would want his BFF sucking his rod wearing his wife’s sexy garments, LOL. So, I took Tyler to a local glory hole. Usually, this cock sucking mommy is the one on her knees waiting for random cocks to peek through the holes.

Not that day. My pretty sissy boy blossomed in her feminine outfit and sucked cocks for hours at that seedy glory hole. I beamed in pride watching Tyler finally get some dick. I even helped him set up a Grinder account. Since his wife gave us permission, I am going to make sure Tyler gets all the cock he wants when he gets sissy time.

Maybe your wife is not as open minded as Tyler’s wife. But that does not matter. We can still enjoy some discreet sissy phone sex.

Sissy Boy Mommy Nicolette Enjoys Panty Boys and Sissies

sissy boy mommySissy boy mommy Nicolette loves panty boys. I kind of earned that nick name a few years ago when I caught my middle son’s best friend in my panty drawer. The boy grew up to be a panty wearing sissy boy. Although he is an adult now, he still enjoys visiting me for some special play time. And I never mind his visits.

To this day, Mark still claims that no mature woman has a closet like mine. I am an old school woman. I grew up in the 80s when women loved pantyhose, stockings, thigh highs and sexy little outfits. However, my oldest daughter puts on a thong and calls that lingerie. Nonsense. Lingerie should entice men, feel comfortable on a woman, and leave something to a man’s imagination. Men require a nice visual for erections. I consider it part of foreplay to dress pretty.

So, when Mark discovered my sexy closest, it awakened the sissy boy in him. And I never mind being a sissy mom. When I discovered his love for panties, bras and hosiery, I nurtured it. A good mommy recognizes when a boy needs special encouragement. However, Mark and I bonded when he was a teen boy. Now, our relationship has blossomed into something very special. He lacks a woman like me in his life. His own parents tried to beat the “gay” out of him.

I Love Sissy Boys

Mark appears to me less gay and all sissy. Although he does transform into a pretty sissy when he visits me, he does not demonstrate much interest in glory holes or cock sucking my lovers. He just likes the freedom to dress up and prance around in my sexy undergarments. When he comes over, I let him pick out any outfit he wants to wear, and I help feminize him with a wig and makeup.

Mark would make a lovely Maria. Naturally femme body. Soft curves and skin. High cheek bones. Beautiful features. Sissy training phone sex helped Mark get in touch and nurture his femme side. And I enjoyed being along for the ride. Perhaps you might enjoy my big sissy closest too?

Mom with big tits lets it all hang out last day of summer!

Mom with big tits

Queenie the Mom with big tits lets it all hang out on the last day of summer! Such a mommy whore with her pussy in the sun for all to see. Last day of summer and there’s no stopping Queenie from flaunting her sexy milf body before the winter months. It’s also the last chance for any curious neighbors to sneak a peek at her sunbathing nude. When she does catch someone watching boy does she give them a show they will never forget. There has been a good amount of cookouts at Queenie’s house this summer, and the holiday season will fill the house with more extended family for Queenie to fuck. That means more hot milf stories for you.

Huge tits phone sex, Queenie’s tits and you in the middle

Huge tits phone sex with your favorite P-mommy Queenie and her hardcore nasty milf chat about being the big boobed, super sexy ass, p-mommy and how she fucks all that ask for a piece of milf pussy pie.

It’s never really hard to get laid at Queenie’s house, Topless girls and bottom less boys scamper around all day looking for something or someone to hump until they cum. I myself am no different, when I get aroused I will stop and begin to please myself wherever I get horny but luckily my house is full of cock willing to service me like the good mommy I am. Feel free to come on over for dinner sometime, we usually have pussy