Category: Sissy training phone sex

Sissy Boy Mommy For The Holidays

sissy boy mommy

I love having you as my sweet sissy and being your sissy boy mommy. Especially around the holidays it’s fun, because I get to dress you up in pretty Mrs. Santa and elf outfits. You look so cute, on your knees by the tree sucking the cocks of mommy’s boyfriends. they love coming over and having your mouth on their big dick. And you know my one friend loves when you bend over and spread your ass cheeks all the way apart so he can slide his massive cock in your pretty lil sissy pussy. It always makes him feel so good. Mommy is so proud of you for being a good slut. That means you’re going to get a really good present this year. I can’t tell you what it is, but let’s just say you’ll be really excited for it. I’ll tell you when you call mommy, but here’s a hint – it’s long, chocolatey, and it’s probably going to leave a big, juicy mess all over your face. If you’re interested in finding out what I got you, then just give mommy a call right now.  You are totally gonna make a mess in your panties and I’m going to have the best time watching you!

Wet Mommy Pussy For A Sissy

Wet mommy pussy is an exciting thing for the naughty Sissy girls. Girly Sissy boys love to wear panties and lick a mommy twat. The best is a creampie mess in the honey pot of their mommy owner. I love my sissy son and get excited having her lap up the seed from a big hard bull cock. You know the first time she got the taste of another mans seed in my mommy cunt was when she was a sweet young thing, I trained her early on to enjoy my mommy pussy. My son was always loving to wear lipstick and dress up in mommy’s pretty things. I have managed to really cultivate this lad into such a good sissy slut and am so proud of my sissy son.

Wet mommy pussy

Whenever I am at home with a nice big alpha male cock fucking my mommy hole, my son is listening and trying to watch. He loves the sloppy sloshing sound of my mommy pussy getting penetrated and fucked into a wet frenzy of a mess. My son knows better than to disturb us. He knows that alpha bull dick is not going to want anything to do with his cucky ass. Not unless he comes in the room dressed like a sissy slut and ready to be a little bottom beta whore for that alpha daddy dick.

ABDL Mommy Phone Sex Regina

mommy phone sex

Are you an adult diaper lover who needs some sweet mommy phone sex? See I have a few favorite diaper boys, {you know who you are} who need mommy to feed them with her big milky tits and change some stinky diapers. I don’t mind stunky boy butts because mommy gets to pay with little peters and have some fun as I change their pampers.

Stroking a small dick on a diaper lover makes mommy so wet! I just know that small pee-pee men all should be in panties or diapers 100% of the time. As a mommy who adores pink bald cocks you should be hair free when you come (Cum) to me in a pamper or pair of panties. I don’t mind wanking a short itty bitty peter but you have to appeal to my P-mommy side at least a little. Or you could write me something like this in my email, and I will go gaga for a sissy slut! 

 

“ I’m working from home today, shaved balls, shaved boy pussy, bubble bath, cotton bikini panties with little blue and white flowers. Working at my desk, my big black suction cup dildo is stuck on my desk top and I am dreaming of you, having me, get up on my desk, slide my panties down around my ankles to suck it and fuck it then cum all over that big black dick and suck it clean for you. Pretty please.”

 

Nothing gets a sissy boy mommy off like An ABDL boi or a sissy writing her poetry such as this!

Huge Tits Phone Sex Mommy

huge tits phone sexYou like huge tits phone sex? This mommy has boobs. No milk anymore, but we can pretend. My oldest son likes to fantasize about knocking me up. That ship sailed a few years ago, but it is still fun to role play. My son was missing mommy last night. He called me up and asked if he could pay me a late night visit. He ended up spending the night. I was not home alone, but his half siblings did not compete for my attention. My oldest son has lots of fetishes and one is being an adult baby. He is not a lifestyle adult baby. But he likes to wear diapers and nurse on my big mommy jugs. I will admit, I struggled at first with his fetish. I mean he has a big cock. He has a great job. He is a handsome man. I thought maybe I was not a good mom and fucked him up somehow. He told me that because I was such a good mom, because I was so nurturing that he wants to pretend to need me to care for him again. How sweet is that? As he was in my arms nursing, I masturbated. I thought about all the what ifs. What if he had knocked me up and we had a girl to raise in the incest way. I massaged his cock like a good mommy whore. It was a tender mommy son moment. Sure, I love a hardcore fucking from any of my boys, but I love the sweet moments just as much.

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

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.

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.

2 Mommies Are A Naughty Fantasy

2 girl phone sex

It’s always fun to team up with Peggy for some mommy time with our Sissies. You should try letting two mommies help you out with that training in being the best little cock sucking sissy faggot. Who can train  sissy better than a hot sexy mommy and sizzling mature MILF duo. It is the best way to get the attention you desire and the guidance in having two cock whores teach you how to please dick. I’m a sexy milf that will always share a cock with my son and make him the best cock sucker. I even dress him up sometimes and put sissy panties on him and make him take a good pegging from myself and my mommy friends. He adores the attention of mommy’s MILF girlfriends. He really loves it when they show up with cummies in their cunts for him to eat out. It’s ok, you can be a sissy and eat pussy. You should learn to clean up your mommy’s, sissy trainers or Mistresses pussy after they take the BBC you crave to take. It’s your first step in becoming the perfect sexy sissy slut.

Sissy training phone sex

Pregnant Mom Giving Sissy Maid Training

Sissy Maid Training

 

 

Sometimes a pretty little fag like you needs a mom who can give you the sissy maid training you deserve! A very pregnant mommy who has huge titties filled with milk as a reward for doing so well. I can barely move with this brat inside me. I require the tightest panties and littlest cock cage on underneath as you are washing dishes. I want you to only have a little frilly apron on and come and rub your cage covered clitty on my hand whenever you need to ask a question of mommy. I will give you a drink after the full set of silver utensils is polished to a mirror shine. You can gulp mommy tit juice and rub my belly full of your little sister as you try to hump mommies leg. Then I want you scrubbing the tub and having your pretty ass up in the air as I move your panties to the side and stick your horse tail butt plug deep in you. Pulling and pushing until your tiny cock is bulging and hurting against your chastity. Satisfied I inspect the toilet and discover my sissy maid fag has left some dirt inside. I pull out the switch and demand that you lick the toilet clean with your tongue now! NO more milk until you learn to be a good sissy maid. You are my bitch and mommy Gabby controls you!