Tag: sissy boy mommy

Mommy Phone Sex or Sissy Mom Sex?

mommy phone sexSundays are mommy phone sex days.  Mommy gets dressed up in her Sunday best. Maybe you get to see her putting on her sexy pantyhose. Or catch a glimpse of her in her sexy undergarments. Are you turned on or jealous that she gets to wear such pretty things and you can’t? A sissy mom would never punish you for wanting to play dress up in her clothes. She would actually encourage it. I have 6 sons and not all of them share the same fetishes. I have two boys that love mommy’s panties, but for vastly different reasons. One of my older sons was a panty stealer. He would take them out of my dirty hamper to jack off in them. He loved the smell of my ripe pussy, the flavor of the cotton lining. Like most teen boys, he was just curious about mommy’s pussy. Once he got to eat and fuck the real thing, he lost interest in my panties. My youngest son from my first marriage however, liked more than my panties. He liked all my sexy clothes, my shoes, even my makeup. He is a sissy boy, but I love him. I encourage dress up. Even gave him a girl’s name since clearly he is more of a daughter to me than a son. We shop together for clothes, he even fluffs some cock for me and does little sissy maid tasks. Sometimes I am a very nurturing mommy, other times I am getting off on publicly shaming my sissy boy. So if you like mommy’s panties for reasons other than mommy’s pussy, don’t feel ashamed. You just need a sissy training mommy to help you be the best sissy you can be. Who is ready for dress up time? Sissy school is now in session.

Mommy’s Boy Becomes A Real Sissy

Sissy training phone sexI told you the next time I caught you in Mommy’s panties there were going to be consequences. Knowing you could not resist doing it, no matter how many times mommy told you, I planned for such an occasion. I o into my room and get the new outfit I have bought for you. When I present you with your pretty pink dress, blonde curly wig, white stockings, and ruffly panties, you complain. You say you don’t want to dress as a sissy, you only want mommy’s panties. I tell you there will be no more half assed crossdressing. Since you want to wear panties so much. you will wear the complete outfit. Hearing the sternness in Mommy;s voice, you begin to comply. You put on the ruffly panties quickly, loving the way the satin and lace feels as it glides over your cock. More hesitantly, you put on the dress and wig. Not knowing how, Mommy helps you get into the stockings. The feeling of the silky stockings is overwhelming as it slides up your skin and I see your erection begin to grow. Mommy knew you would love this. A cute pair of Mary Jane shoes complete your outfit. You say you feel ridiculous, but your rock hard cock tells another story. Now its time for Mommy’s little sissy boy to service Mommy. My pussy is dripping wet and ready for your tongue. Oh, you thought you would fuck me? No, sissy’s don’t get to fuck Mommy. Sissy’s serve Mommy and Mommy’s friends with their tongues. You will get me prepared and watch Mommy fuck a really big cock. After I am finished I will need you to clean my pussy for me. That’s right, you will suck all the cum from Mommy’s pussy. I know you love the taste of male cum just as much as you love putting on these sissy clothes. If you are a really good boy, I may even let you suck my pussy juice off my friend’s cock. You always did want to suck a great big cock, didn’t you?

Momma’s Big Adult Baby!

Milf fantasy stories

My sweet son get’s what ever he wants. He knows how badly mommy wants a new sweet angel to gush over, and care for just like she did him when he was new to the world. God just thinking about how sweet the fresh new ones are to in this world makes my pussy wet! That is why my sweet adult son loves to dress up as a wittle adult baby! He goes potty in diapie and mommy gets to clean him up! His poopies are stinky! But I get to clean his ass, I love wiping all of his shit off his cock and balls. I am so genital with his big boy cock that he get’s hard for him mommy. Some times I get so fucking turned on as I wipe my sweet adult baby boy’s ass I have to suck his cock before I finish cleaning him.. I have to stick his big cock deep into my pussy and fuck him while he sits in his dirty diaper!!

Make me cum for Mother’s Day

jack off with mommy

It’s Mother’s Day and I can’t believe the party my boys threw for me. All of my little sissies did the hottest lingerie show for me. I have way too many pairs of panties myself so I let them raid the panty drawer.  Let me know if you want to buy some for yourself. Then you can really jack off with mommy as you wear your special sissy panties that I hand pick for you. Feel how your cock swells when  you put them on. That’s because you really are a girl at heart. A girl with a penis is a great thing. Let me show you what I mean. I want to see you bent over with your panties down as mom guides a hard dick into that boy pussy. I’ll teach you how to fuck and suck so you can be the hottest sissy around. Mommy will break you in right for Mother’s Day. Bring that ass toy with you. You’re gonna need it.

Mommy Specials for you.

jack off with mommy

Are you ready for something special? How about a hot phone sex special? You never called me and now is your chance to see if I can rock your cock. A good mama always give her boys the “special.” I’m a very naughty mommy and I love incest phone sex and all of those things that young boys fantasize about. Remember trying to get a peek of mom’s tits? Or those times you snuck that pair of dirty panties back in the hamper all gooey with your cum.

Don’t be a shy guy. I’m a sweet mom who dotes on her boys needs. I know how to handle a young man who is afraid to tell mom how much he wants her. Let’s do a horny roleplay and I’ll be the mommy you wish you had. Let me take your virginity or introduce you to my strap-on. You’ll always have fun when your mommy is like me. Newbies always welcome. I cater to cowards.

mom fantasies

Mama Pearl on Being a Cock Sucking Mommy.

cock sucking mommy

Every young woman needs a cock sucking mommy like me to teach her the ropes. There’s an art to cock sucking and once a girl learns it, she will never want for anything. Men love a girl who is good with her mouth. He’s more than just a meat popsicle you know. This is aimed at my cock loving sissy boys, too. Listen to this experienced cock sucking mommy and I will teach you to give the best head ever. If you are shy, go to your local glory hole and practice on some anonymous cocks until you learn to swallow and feel confident with your technique.

Take some advice from Mama. I will train you right. Cock sucking can be great. Once you get a big meatstick in your mouth, pumping away, you’ve gotta know how to handle it. Slurp it, make some noise. Moan. Whimper. Don’t be quiet. Sound is like gasoline. It adds heat and fire to that blow job. Keep that tongue moving. Swirl that head, suck those nuts, use that hand to make things feel tight and juicy. Don’t just be a bobbing head doll. Fondle and tickle those sacs while he fucks your tonsils. Slide a fingertip into his shithole and see how he reacts. If you don’t get your make-up smeared all over your face, you’re not doing it right. Next, work on that gag reflex. Men love to make you choke on that dick but no one wants to get puked on….Well, most don’t…but that’s another blog!!! Learn to swallow that beast. Let those balls slap your chin. When you feel them draw up tight, you’re almost there.

You’ll hear him begin to moan. Some men beg. Stop several times and make him wait. It’ll make him cum so much harder. His fingers will clutch your hair and he may grab your head and push himself into into your mouth, faster and deeper. Now wait for your prize. Yes, that cum is your reward. Slurp up every drop, roll it around in your mouth, show it to him. Wear it or share it!!! Let it dribble down your tits. Now swallow and smile. He’ll be in love, sweetheart. Take it from an experienced cock sucking mommy who wants her little girls and boys to give and get the best blow job ever!!! Take it from mama. It works!!!

jack off with mommy

 

The sissy and the mother in law

mommy phone sex

I knew that my son in law was a sissy from the day my daughter married him. I had been staying with them on vacation when I figured it out. She was at work. I found him in the bathroom hand washing several pairs of panties. “So, does she know the truth yet?” I asked him. He turned shades of red. “What do you mean?” he stammered. “You’re a panty wearing sissy and you’re washing these so she doesn’t find out that you borrow them.” I giggled. I saw his cock rise in his shorts as he realized that he was busted. “Come with me.” I said. I opened up my suitcase, revealing dozens of panties. “Take what you want. I understand.” He hugged me hard. I slide my hand into his shorts, feeling his silky thong. “I know exactly what you need.” I opened my overnight bag and brought out a strap-on. His eyes got huge.

We spent the rest of the afternoon breaking that new boy pussy in. He took every inch I gave him and begged for more. I loved his whimper as he gave up his cum, his legs over my shoulders like a good little girl. I think it’s going to be a fun week here as I continue his lessons. Tomorrow we are playing dress up and this weekend we have a date with one of my special friends who loves breaking in virgin ass. I can barely wait to guide that thick cock right into his new pussy. He’ll be wearing my pink thong panties as he gets fucked.

Milf chat with Mommy Pearl

milf chat

Both of my sons were in for my birthday this weekend. I was so happy to see them together. They took me out to dinner and went we got back, one of them brought me a glass of wine. I was relaxing on the couch when both of them came in the room together with a cake, singing Happy Birthday. “Blow out the candles, Mom.” they laughed. They were both naked and very erect. My older son, Brad,  has a long dick and my younger one, Matt, has a fat juicy dick. They came over to the couch and pulled off my dress before I could say a word. My young one sucked on my nipples like a titty brat. The older went to my pussy and had my panties off before I could protest. I just settled back and let them give me my gift. Total devotion from my boys. Brad buried his face right in my cunt and began to lick it. Matt slid his fat cock between my titties and fucked them, letting me have a taste. It has been so long since I’ve fucked them together. They gave me so much pleasure growing up. Brad flipped me over so he could penetrate me from behind while Matt moved to my mouth so I could suck his cock. They fucked me back and forth like a Mommy sandwich. I was moaning and my pussy was in heaven. They switched places and I felt my younger son really stretch me out. I couldn’t take much more. “Fuck Mommy, please. My sweet boys, I want your cum.” I cried. And they gave it to me all right. One gushed in my pussy while the other one gave me some nice cream for my cake. Mmmm, I can still taste him on my lips. And boy, did we have fun sharing that cake later. What a creamy mess!!! Best birthday ever.

Mommy sucking dick with Daphne

Mommy sucking dick

I know you watch Mommy sucking dick in the hallway mirror. You are supposed to be in bed. Instead you are rubbing your cock while watching mommy sucking this big black cock. You are not being a good boy and you know what Mommy does to Bad Boys. You watch Mommy dominate her her Sissy boys and make them suck big black cocks. You know that Mommy loves have a nice big thick nigger dick in her mouth just as much as she loves having it in her pussy. You also know that Mommy loves watching little sissy fags like you sucking on big cock. You are being such a bad boy, do you need a spanking from Mommy? Mommy will spank your bottom until your little ass is all red. Then Mommy will make you choke on his big black cock getting nice and wet. And he’s going to take that big cock and rub it all over your tender ass, and make you his bitch. No do you want to be a bad boy or do you want to be a good boy and do as you’re told? Mommy loves it when you’re a bad boy.

Mommy Whore Shares Son For Doctor’s Day

mommy whore

It was time for a check up for the boy. You discover he has on satin panties and ask him about them. Embarrassed he replies that he just loves the way they feel. You admit that he does look rather sexy in them and that they showcase his young cock nicely. You tell him he needs to remove them for the exam. He does and you inspect his parts. You comment that his ass looks a bit stretched and you need to check to make sure everything is ok inside. That is when I notice the bulge in your pants and realize this will not be a routine doctor’s visit.

You use your finger to inspect his ass and decide you need something that can reach deeper to check it out really well. You give me a wink and I know what you have in mind. Since it is Doctor’s Day and you are being so nice, how could I refuse yo this pleasure? Actually, I wouldn’t refuse you anyway. A dirty mommy whore like me gets off on watching her little sissy boy get abused. I watch as you take your cock out of your pants. You use the KY to prepare his ass and your cock. I finger my pussy as I watch you begin to push that bulbous head into his tight little ass. He whimpers, partly in pain, part pleasure. You begin to stroke your cock in and out of his ass. You and he both look like you are in heaven and I finger my sloppy wet pussy even harder. You say that his ass seems to be fine and you need to check his tonsils. You pull out and move to his mouth, proceeding to fuck that sissy mouth with your dirty cock. I watch you and I stroke my clit even harder. I am on the verge of coming when I see you start filling his mouth with your cum. I wait for him to finish swallowing and then sit on his face and ride it to my own orgasm.

What a fun way to celebrate Doctor’s Day! Best of all, the visit was free!

sissy boy mommy