My son said he was sick. I figured it was a Ferris Bueller type thing. He just wanted to skip school and have some fun. I get it. I didn’t take his temp or anything. I just trusted what he said. I stopped home at lunch to see if he was feeling okay. I half expected him to be gone. I got the surprise of my life when I found him sucking the neighbor boy in a pair of my panties. My son was a cock sucking fag? I knew he was not interested in my mommy pussy, at least not like his older brothers. I figured maybe he was just too young and one day he would be a mother fucker like his brothers. I knew the problem then. I didn’t bust him. I did watch him polish that neighbor boy’s knob well. I got to thinking that maybe what I had here was a sissy boy. What woman can’t use a sissy boy son? I left discreetly, but when I came home from work, I had a bag from Victoria Secret’s. I showed my son all the sexy things I bought and gauged his reactions. He clearly loved the sexy lingerie I bought. I asked him if he wanted to try the items on. He looked at me like he just won the lottery. He was a natural in lingerie. I told my boy he was born to be a sissy. He has been my sissy ever since. So now I am a sissy mom but I love it.
Pearl's Phone Sex Blog
I have a sissy son so I’m a sissy mom
Sissy Mom Pearl Has A Sissy Son
I love being a sissy mom. I have a sissy boy. I knew from the time he could walk that he was not going to grow into a man. I could have forced the issue; I could have gone against his natural inclinations, but where is the fun in that? My son would have hated me, and he would just grow up to be another unhappy person in the world. My son and I have a very special relationship. I promised him if he did well on his first test of the year, I would take him on a shopping spree to his favorite store. Most boys his age like shopping sprees at The Game Stop or a toy store. Not my sissy son. His favorite shop is Victoria Secret’s. He came home with an A+ on his first test yesterday, so we went to the mall. I even let him dress up in a pink dress and Mary Janes to go shopping. He was so happy! I am not ashamed of my sissy boy. We let the ladies know he had $500 to spend on pretty things. I helped him try on sexy undergarments he can where under his boy clothes at school. I hate that I must send him to school dressed like a boy, but the school is not progressive thinking. Now he has lots of pretty things to wear under his boy clothes to make him feel girly. The sales ladies loved dressing my sissy boy as much as I do. Do you need a sissy mommy too?
Discovering your feminine side
I come from a long history of incest. It’s sort of a family tradition. Fucking my boys was never a big deal to me. Teaching them to be men and how to touch a pussy only helps them. It wasn’t until my middle son, Steve, taught me a lesson and changed my life.
Steve was always a gentle soul. He hated sports and doing stuff with his brothers. He preferred to hide in his room and watch TV. I was getting ready to go out. That’s when I noticed something funny with my make-up. It was all messed up and some of the lids weren’t tightened. I was baffled. But when I went to put on my favorite slutty dress, it was gone. A light went on inside my head. I ran to my panty drawer and opened it. All of the tiny bikinis were gone and a few bras.
I kicked Stevie’s door open and there he was. All dressed up in my clothes, wearing make-up. “I want to be a girl, Mommy.” he sobbed. I rushed to hug him, whispering. “It’s ok, sweetheart. Mommy will help you. Pull down your panties and show me your pussy.”
And that is how I became a sissy boy mommy. So, if you are like my Stevie and hiding your secret, you can come to me for gentle support and lessons on being a girl. Let’s start with stretching that new pussy. be sure to bring your toys when you call.
Panty Training
You just needed a gentle mommy’s touch to bring out your inner faggot. You were so shy and barely mumbled when I asked how I could help you. I told you by the hand and looked you in the eye. “Do you want to be a girl?” You nodded, looking at me with your luscious eyelashes. I could already imagine your slender body all dressed up as a girl. Your round ass clad in sating bikini panties. You would be a knock-out. Men would be lining up to have those full lips wrapped around their cocks or to push throbbing fuck sticks into your tight little boy-pussy.
I felt my own cunt twitch a little as I handed you a pair of panties. You tucked your teeny weenie and little shaved balls into them and you were transformed. It was time to bring out my special tools to make you into the sexy cock slurping whore that I knew you were. “Pull down your panties and show me your pussy.” I ordered, slipping my strap on over my own panties.
Hot for teacher mommy
One of my earliest Milf fantasy stories goes back to when I was a substitute teacher at a school for unruly boys. These walking bundles of hormones could barely keep their eyes off my huge tits and round ass. One time there was this older student. He was really built and always reeked of Polo cologne. He got this huge crush on me and would make comments all the time about his sexual prowess. He claimed to have a ten inch cock. With him being white, I highly doubted that.
Oh, I was a flirt back then. I wore low cut shirts and bent over those desks, giving the boys a peek. My endowed student decided to give one of my globes a firm squeeze and I promptly slapped his hand down. “Hands off the merchandise.” I warned him. His face turned red with face.
I had stayed over after class to finish my lesson plan. The students were gone. I didn’t hear anyone walk in. Then boom. I was slammed face down onto my desk. My skirt was flipped up and my panties were yanked down. I felt something large and wet press against my furry gash. I wiggled to escape but instead felt a huge cock ram into my pussy. I tried to scream but a hand was clamped over my mouth. He fucked me fast and hard. As he leaned down to whisper in my ear, I caught a faint whiff of Polo. I screamed out loud with the force of my own orgasm as he dumped a massive load of cock cream deep inside of me.
Put these lace panties on and confess.
I’m a real life mommy but being a Sissy boy mommy is my favorite role. Guiding little faggot boys into being girls makes my pussy wet. You just need a little guidance, young sissy, and soon you will be what you’ve always known you are.
I pulled the strap on over my panties, marveling at my huge cock. You were bent over in front of me, trembling in fear and arousal. “I’ll be easy.” I whispered, as I pushed my fat cock head against your pucker-pussy. You gasped just a little as I gave it a nudge, opening you. I squeezed your round ass cheeks as I shoved a little deeper. “Squeal for me, sissy. Tell me what you need.” You gave a little faggot moan and arched that pussy higher. “I need fucked, mama.” “What do you want?” I demanded. “Cum. I want cum. “Louder.” You squeaked louder. “Please. I need it so bad.”
I pumped that little bitch until your boy pussy was raw and you loved it. Now pull those panties up and feel the cum seep from your wounded hole. It’s time for round two.
Sissy Boy Therapy
You’re up late tonight. You’ve already jacked off three times but you need some Milf fantasy stories to really empty those balls. It’s time you talk to a real life mommy who gets what you really need. No amount of phone sex moaning is going to satisfy you when what you really want to be is a sexy slut.
Think of me as your phone sex therapy mommy. Having a sissy boy of my own, I totally get your needs. The way you want to dress up. I can even send you the perfect pair of panties. Nice and fragrant, to make you think of mommy. You want to please mommy, right? So put on those panties, grab that trainer ass toy, and let’s start this session.
Tell me about that cock you crave. Is is big? Do you want to be submissive and forced to gag on it or just allowed to nibble and tease? Does mommy need to stretch that pussy first with a dildo or strap on? Or are you an eager slut who wants that boy pussy pounded hard? One call with Mommy and we can explore your special needs. Your clitty will explode in those panties. Quit denying the faggot truth and come talk to me soon.
Mommy does BBC training
This will make you Jack off with Mommy for sure. I got a sample of the fun we’re going to have in our sissy training class. I hand picked some big black studs who love to break in a new sissy pussy. Oh, we’re talking 10 inches of throbbing nigga meat. I’ll have you all dressed up for your first date with them. Mama will get down on her knees to demonstrate the techniques you need to learn. You better get that big dildo out and practice stretching that boy pussy so you can accommodate this much girth.
Bend over, little sissy, and show us your faggot hole. My nigga wants some of that cherry. It looks so tight. He’ll make you squeal like a real girl as he humps that pretty ass. Let me demonstrate on how to eat this much cum. These guys are known for their potent semen. Open that mouth wide, you’ll only be able to gulp that first squirt. Let it dribble over your lower lip, down your chin. Stick out your tongue and show him his cum. Now swallow and smile like a good faggot slut.
You’re almost there. Now bring an ass toy and let’s practice stretching your new boy pussy. Soon you’ll be able to handle unlimited meat sticks all night long.
Knock your mommy up.
I just decided that it’s time for some breeding phone sex. Expanding the family tree means more playmates for us. Yes, I know you wish you could be a breeder, little sissy, but right now we need those little spermies for something more important. I need you to jerk that little clitty into this jar for me. No, you can’t drink this load. It’s for Mommy. Since you can’t have little spawn on your own, Mommy is gonna make one for you. Then you can feel like a woman. I can’t wait until we train it together.
Or maybe we’ll just go out for 4th of July fireworks and cause a few explosions. You get your boy pussy fucked and your mommy will get herself knocked up. I’m sure there are plenty of virile studs out there who will be more than glad to donate a load or two of sperm. Party hard tonight and then come join me for some hot and horny mommy pussy. I’m craving some cum so bad. Older women know how to make you blast off like a bottle rocket dipped in gasoline.
You say Sissy like it’s something bad.
I’m not your regular old run-of-the-mill mommy. My specialty is tranny girls, sissy boys, and playing dress up. Plus good old fashioned spankings for naughty boys. When you need a real mommy with experience, you need to come get some tutoring from me. I will make you into a real life sexy slut. I love getting your pics and showing you exactly what you can become. Bring a toy for our calls and we’ll stretch that new boy pussy to handle the biggest cock. Mmmmmm, I know you love cum.
So, go raid your wife’s or daughters panty drawer. Or order some from me to play in. This mommy is going to teach you the ropes. Don’t be shy, little sissy. I can tell from the way you walk that you’d make a natural slut. With that round little ass and cock sucking lips, you’ll get more cum than you can handle. All you need is a little training and you’ll be on your way. I’m your new non-judgmental mommy and I will bring out the best in you. Don’t be shy. Share your fantasies and come get off with me. I know that little clitty needs some attention.