Category: Sissy mom

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!

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.

Sissy Boy Mommy Wants to Play

sissy boy mommy

Oh, I just love being a sissy boy mommy. When my son was younger, I walked into my bedroom one day and caught him wearing my panties and jerking off. He was embarrassed for some reason, even though I’d been playing sexually with him and his siblings for a long time. I told him he had no reason to be shy and that if he wanted, I would help him get dressed up in more than just panties. He reluctantly agreed and we went into my closet to find some lingerie and a nice dress for him to put on.

After he was all dressed up, he asked me if I would get my strap-on cock and fuck him. I was SO happy because I’d been hoping that one of my sons would be into that! I told him to bend over and I squirted some lube on his pussy and started to slide inside him. I got so excited that I reached down to touch my pussy and came almost instantly. Do you want to hear more about the things I did with my sissy son? Call me and I’ll tell you how I pimped him out to all of my male friends with enormous cocks.

Sissy Maid Training Mommy

Sissy Maid Training

I’m a slutty, slutty mommy who believes in sissy maid training for my sons to be disciplined for me. It makes me so happy when I have the opportunity to transform my sweet sons into little  sissies who cater to their mother’s every whim. My baby boy’s clitty is absolutely darling, and dressing him up in adorable frilly dresses with matching stockings, panties, and training bras is just too much fun! To make me happy, he said he wanted to do anything, so today he is my little maid and I can play with him however I please.

It’s the most adorable little French maid ensemble I’ve ever seen. He looked exquisite in his short skirt and thigh-high white stockings. I had ordered him to draw me a nice warm bubble bath, and since he was such a good boy, I let him wash my huge milky tits as well. Next, he proceeded to take care of Mommy’s hair. It felt really nice to be pampered by my son in his sissy outfit. Now that he did such a good job of taking care of me, I allowed him to enjoy himself after I had finished drying off. Until he came right in his panties, I rubbed his little peter through his sissy slut panties. Now for step two of Sissy boy phone sex with mommy Regina, Finding a cock to train him on, Mommy does have a nice big strap on to help open up that ass.

My Phone Sex Blogs Reveal I am a Dirty Mom

phone sex blogsIf you read my phone sex blogs, you will see I am a fan of incest. You will also discover that I love younger men. I married a man only a couple years older than my oldest son. They went to high school together. My husband is in his 30s and I am in my 40s, but we have a great marriage and a son and daughter. My husband never asks me for favors, so when he did, I jumped at the chance to help him. He hates to ask me for things because I put him through law school. I never look at it like he owes me though. I mean he knocked me up in my 40s, so I owe him. Anyway, his nephew needed a place to stay.  The boy came out as bisexual to his parents, one of which is my husband’s sister, and her asshole husband kicked the boy out. Of course, I would let him stay with us. He is older than our son and daughter, but still in high school. As of now, I have an extra boy in the house. One who likes cock and pussy. That is like music to my ears. I think men should relax more and take cock in the ass sometimes. It always leads to a good ball draining. I caught my nephew by marriage in my lingerie drawer last night. He thought I was going to kick him out. Hell, no. I assured him he was welcome to be himself around us and free to play with any of my sexy things. I can be a sissy mom now with him in the house. I dressed him up in some stockings and a garter belt with matching bra and underwear. Then, I pegged his ass.  A bisexual sissy boy in my house will be a wonderful addition.

No competition

milf chat

My mind races with all the milf chat fantasies you possibly might have. I like to think about young boys and seduce them and make them have the best cumulative ever. I’m a young hot mom, and when I move into the suburbs, I don’t mesh well with the other moms. Especially the moms that have boys that are older and completely legal. When they hit 18, it is my kryptonite. My pussy begins to squirt at the thought of showing a little boy how real women can rock your world.

Get ready to enjoy the premium pussy of your dreams. It is about to get wild with me. I’m going to rock your world and your cock.

Don’t ever for a moment think you will have a better experience with those barely legal chicks. You need a hot young milf like me to show you I’m hotter than the girls 10 years younger and the ones 10 years older. I’m at that sweet spot where I’m young enough to pass for an older coed and old enough to be your English teacher.

Small Boy Cock Mommy phone sex

mommy phone sexWouldn’t it be nice to try some of Mommy phone sex pussy? I’m sure I’d be delighted to show you everything Mommy enjoys. You know what time it is, letting Mommy Regina play with that sweet little boy cock, time!. Where have you been hiding my baby boy dick? It should have grown nice and fat by now! Let Mommy take a look. Oh well fuck baby, that dick just never grew did it! That’s okay mommy likes small peters, I don’t understand how your daddy has suck a big fat cock and you don’t. Remove your underwear and sit back while Mommy demonstrates what Daddy enjoys. Mommy takes the baby cock in her hands and jacks it off so easy! Look at your wee sister. She doesn’t understand what mommy is doing to your peen, thank goodness it’s small, otherwise might have frightened her! Massaging the little cock up and down, making it bigger and bigger. But it just barely grows! No baby mommy wont tell no body how teeny tiny it is! Just like when you were a tot! Mommy suckles your dinkie and takes the whole thing and our cute little balls in her mouth! Now it’s your turn to suck wet mommy pussy! Mommy lets you crawl between her thighs, revealing her Milf cunt. Isn’t that a cute little button over there? That’s a clitty, and you can rub it between your fingers and with your tongue. That’s a fine young man! You’re doing fantastic! When you kiss her pussy like that, Mommy likes it! Oh? You want to fuck mommy? But I wouldn’t get any pleasure out of a small peter like that! I look to your sister, on the other hand i might have a hole small enough for you after all! I guess the question of the day is any p sissy boys with wittle dicks ready for mommy Regina?

hottest milf in town!

wet mommy pussyMy MILF cunt is all filled up with cum. That’s just the way I like it. The way I figure it if I keep my pussy filled with

a bunch of swimmers all the time, I can keep myself pregnant with nice big tits swollen with milk all the time.
Today, the chance for cum came by accident because four teenagers from the community college were
walking the neighborhood offering to wash cars to raise money for their softball team. I told them they
could do something else for me.
Before long, I had a young cock in my throat and a young cock in my cunt!
I made sure the boys knew they could take my throat or my pussy or my ass but when they were ready
to explode I wanted all their seed right where it belonged, in my hot little mommy pussy. So, I got my
throat fucked and my ass fucked and my pussy fucked but all the loads went right in my babymaker.
You know what else? There’s something wonderful about younger men like that. They can cum more
than once! I didn’t get four loads in my pussy. I got eight! When they left, I gave them ten bucks to wash
my car after all and I made them promise to come back tomorrow.
Tomorrow they’ll be bringing the rest of the softball team.
God! I’m so fucking horny I can’t stand it. I need it tonight. I need someone to put more swimmers inside
of me.

Sexy Sissy Boy Mommy Regina


sissy boy mommyThe best part about being a sissy boy mommy is the spankings! My boy was being watched by his uncle Steve and I got an unexpected phone call while I was out with the girls! My son had called to tell me that Uncle Steve was very upset with him and to look at my Snapchat! My son was naked wearing my brand new expensive Nylons! Naughty, naughty boy. I made sure to let him know that uncle Steve was going to spank him when I got home to go to mommy’s things! Plus, he shouldn’t wear only nylons and no panties or bras! If your going to be a little sissy fag, you must go all in! I raced home thinking of the spanking that young tight boy ass was going to get. My mommy cunt was soaked and all this mommy slut could think of was how to punish my boy more. My sissy boy son didn’t expect me home so soon. He was in my make-up and wearing my heels just shaking his pink balled little cock like it was 1999! I pulled him by his little weenie right to his Uncle Steve, who looked pleased to spank my young sissy fag! I made my brother steve Strip to his Skivvies and I dropped my little black dress revealing little covering my hot milf body! I told my son as he got spanked that he would be pleasing my cunt and Uncle steve. I might be a sissy mom, but I have needs too. And my little faggot son made me miss a good dick, so i was going to masturbate while he was spanked red like an apple!sissy mom

phone sex whore stepmom

 

phone sex whore

My stepson hears me be a phone sex whore. This has been my guilty pleasure, but I love that he hears me get so many guys off, and I love that I know he’s jerking his dick. I tease him all the time after a call. I am usually wet and fucking horny, so I go ahead and mess with him for a bit. I haven’t let him get his rocks off with me just yet.

I like to tease boys and want them to beg practically. I have a special place in my heart for boys that are about to become men. I like to help them cross over, so I do admit I like being their first.

I know that from that moment on, they will always compare every girl to me. Quite frankly, no girl will ever even meet the standards I set. My stepson will forever have the longing for my pussy even after I am long gone from the picture because I don’t like to stay in a marriage for long. I like to target my next victim.