Category: Sissy mom

Jack off with Mommy for the first time.

jack off with mommyEvery boy has a need to Jack off with Mommy. It’s important to have a strong mommy figure in your life. Maybe your mommy worked too much or maybe she was a total whore who neglected her young son. Either way, you have this craving for a mom. I know every boy needs one. Whether it’s to call for advice or to fantasize about. Mommy was your first love and you lived for a peek at her tits or a flash of skin in the bathroom. Your first pair of panties belonged to mommy. The ones you picked up and looked at. Maybe you even sniffed them, and it got your boy dick hard enough to jack off with mommy.  If you were a lucky boy, your mommy sat you down and told you all about women and sex. Perhaps she gave you a look at her tits or pussy. If you were my son, I’d have done more than that. I would’ve taken that dickie into my mouth and given you a blow job.  Or if I was feeling horny, spread my legs for a better look and perhaps even let you poke your throbber into this slit. We wouldn’t have stopped there but I’m not giving you any more details until you give me a call. Come Jack off with Mommy soon.

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?

Memories of a school nurse…

 

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I bet every boy there remembers having a crush on that cute school nurse. Not that old grouchy one but the one who filled in when she was off.  I remember those days too. I was such a flirt when it came to those boys. They would come see me for phony headaches and with fake coughs. I found that a flash of tits was the perfect medicine for these naughty young ones. There was one I that especially liked. He was a big boy, much more mature than the rest. During a rough game of kickball he took a boot to the nuts and arrived sobbing in my office. I had him lie down on the bed while I got an icepack. He was so embarrassed when I asked him to drop his pants for me to check him. OMG, this young boy was packing the meat. I touched it gently and examined it for internal bleeding. He got very quiet as I stroked it. Suddenly, it sprang to life. His poor purple cock was 9 inches long. I gasped out loud. I still had my hand around it and it just seemed natural to take it into my mouth. I told him I needed to make sure his blood flow was ok. I’ll never forget the way he pumped that boy cock into my mouth or the sweet load of spermy soup that he squirted. I can still taste the sweetness of youth. He was feeling much better after that. After that day we seemed to have more ball mishaps than ever before but none were better than my very first.

Make me cum for Mother’s Day

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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.

Mama Pearl on Being a Cock Sucking Mommy.

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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!!!

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Big boys love MILF fantasy stories

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Since I’ve gotten older, I seem to stay horny all the time. I look at all of these young men and I want them. I thought my sex drive would diminish with age but it’s burning a hole in my panties. I eye up these young studs like they are prime cuts of meat and imagine what they are packing in their jeans. I had an experience lately that should make me blush. The cable guy stopped by to fix my system. he was cute. I watched him as he was bent over on the floor working on the hook-up. I stood right over him with a short skirt on and no panties. He got a great look at my bush. “Ma’am, you look awful sexy from this position. I’d sure like to put you in another.” He was a bold one. I squatted right over his face and made him eat my pussy until I creamed. He looked up, my juice all over his face, and I wanted more. I pushed him back on the floor and unzipped his fly. His big brown cock poked out, already swollen with excitement. I took him in my mouth and gave him the best blowjob of his life. He was gasping like a fish as I emptied his balls. I forgot how fast young men can recover. He was hard again within minutes and this time he took charge. He took me right there on the floor. I was begging as I felt his fat cock shove into me. He pumped me fast and hard, his balls slapping against my cunt. He was aggressive and I felt his forearm wrap around my throat, pulling my head back. I had no idea that cutting my air off for a few seconds would make me cum so hard. He filled my hungry slit and put his cock away, still wet. I want to smell you later, he said. OMG, it was the hottest fuck of my life. I am ready for some more!!!

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Mommy Whore Shares Son For Doctor’s Day

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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!

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Phone Sex Mommy Nicolette is a Sissy Mom Too

phone sex mommyI want to be your phone sex mommy! You can be any age you want too! As a P mommy, I have played with sons of all ages.  And I have sons of all kinds. Currently, I have a school boy who thinks he is a school girl! Naughty little boy who likes to wear mommy’s panties.  He had an accident at school yesterday that tore his jeans during recess. The whole school saw that he was in women’s panties and laughed at him. They called him a sissy. He ended up in the principal’s office. I had to go bail him out of jail. I have told him time and time again, he can wear my panties at home, but never at school. School age boys and girls can be very cruel. The principal suggested I get him counseling. Like the principal never stole a pair of his mother’s underwear before. Every guy goes it. Doesn’t mean they are gay or even a sissy. Some boys  just like to feel close to mommy’s pussy. Some like the feel of the silk on their little dicks. Some realize they have little dicks that get lost in boxers so prefer the tight fit of mommy’s panties on their junk. I asked my son when we got home, why he disobeys me by wearing my panties to school? He told me he thought he might be a sissy. I asked him how he even knew about such things at his age, and his response was from you on the phone! He has been listening to me be a sissy mom for all my phone sissies. Luckily, my boy toy husband is very open minded. When I told him that his son thinks he is a sissy, he didn’t shame him or even punish him. He just pulled out his cock and ordered his sissy son to suck daddy’s big dick. Sissy school is in session at my house!

Sissy Mom Nicolette: Springtime is for Sissies

sissy mom springI’m a Springtime sissy mom. What does that mean? It means that as the temperature gets warmer and the flowers begin to bloom, I start to clean house. But in my house, that means something different than just putting winter clothes away. It means getting sissy boys ready for the new season. My friend Gloria has a son who we think was born in the wrong body. He is no man. When he was knee high, he was wearing mommy’s panties and playing dress up in her clothes. I would come over and he would be prancing about in high heels wanting us to join his tea party. Gloria just laughed it off as his experimental stage, but I knew he was a sissy boy even then. My best friend has resisted my pleas to just make him a full fledged sissy. We had lunch the other day, and I begged her to bring him over for my springtime cleaning ritual. She finally agreed. Springtime is for sissies!

sissy boy phone sex springWhen they arrived, I slapped a collar on Derek and informed him his new name was Denise. He appeared scared and aroused simultaneously. Every woman can use a sissy in her life. They make excellent maids, bitches and fluffers. It is when they are in that girl not ever going to be a man stage that they are annoying little whiny ass fuckers. They need a dominant mommy to convert them to full fledged sissy and become their master. They need my springtime ritual. Denise was held down while I fisted her back door pussy. I wanted to pop her sissy cherry while Gloria rubbed her little clit stick with the vibrator. A sissy’s first cum is special. Just as special as a sissy’s first fuck. I let her mommy take her tight virgin ass with a strapon while I fucked her pretty little mouth with mine. Tag teaming a sissy is so much fun. After a sissy’s first fuck, comes dressing the sissy. I had a pretty pink frilly springtime dress laid out with a white bonnet and some white sandals. Gloria couldn’t believe the transformation. Thanks to my sissy springtime ritual, she now has a full time sissy who will cook and clean for her, plus pamper and amuse her; even procure cock for her and clean up her cream pies. A sissy is a dominant mommy’s best accessory. Are you ready for your conversion? Sissy boy phone sex awaits you.

Phone Sex Mommy has a Wet Mommy Pussy for Horny Boys

phone sex mommyThis phone sex mommy loves talking to boys who crave their mommy’s pussy on their dick. Maybe even their mother in law or best friend’s mom. Mommies come in all types. I have fucked my own brats. I have fucked many of my sons’ friends. Even fucked my husband’s brother and father. Guys like a hot MILF who has no limits like me. The sad reality is that very few men act on their impulses to fuck their mother. They are afraid of the reaction. I mean what is the worst thing that could happen? She tells daddy and you get an ass whooping? Sometimes a good spanking is pretty hot, for both of you. However, what is the best thing that could happen? Your hard cock slides inside your mommy’s warm wet cunt.

I have all sorts of mommy’s boys who call me. Some just want to fuck their mommies. Others actually do have that coveted incestuous relationship with mommy. Some men I talk to have a hot relationship with their wife’s mother. This is actually very common. For others they are or have fucked a best friend’s mom, an aunt or even just a hot MILF at some point in their life. Some of my phone boys are men, some are sissies . But every single one is a mama’s boy of some sort.

wet mommy pussyFace it, mommies are hot. We give birth. We have big tits. We have a wet mommy pussy that tastes and smells so yummy. We have experience. We are nurturing. We are disciplinarians. We are horny. We have no limits. What is not to like about a hot mature woman? I spend my days on the phone helping men like yourself have the sexual relationship with the mother in your life, but I spend the nights playing with my brats. I have young and older brats to play with and a boy toy husband with mommy issues who likes to watch and participate. So trust me, I have the experience and knowledge to help you fuck the mommy in your life.