Archive for the 'Sissy Lessons' Category

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Pretty Things for Pretty Boys

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I was getting ready for a date and noticed my step-son looking in through my partially open door. He was in his sleep pants and had gotten ready for bed like a good boy. I pretended not to see him as that would have wasted time and I was already late. While I was hooking my pretty white stockings to my garter, I heard a slight moan. I looked in the mirror to see the doorway and he was rubbing himself through his sleep pants.

I stopped what I was doing and told him to come in as clearly we needed to have a talk. I had a feeling from finding my lingerie out of place lately that it wasn’t Mommy he had a boner for, it was Mommy’s pretty, soft lingerie. I texted my date and told him to bring something to drink and some take out as our date had taken an interesting twist.

When he arrived my pretty “daughter” and I were waiting downstairs in our pretty lingerie. He had a huge smile on his face as he always wanted to play with a mommy and daughter. He knew it was my adorable son but he went along with the game. Jamie went to the kitchen and got our glasses and plates like a good girl wearing a sexy little sissy maid outfit. My date popped in a porn and we settled in for a night  of sexual exploration. My sissy boy sucked his first cock while mommy went and put on her strap-on. This was a night we will never forget and the first of many.

Fuck Slut Michael

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I have a little sissy fag bitch that calls me named Michael. He’s a real pathetic piece of shit. I dress him up like a little whore and then make him play slut for me. I always make sure that I have plenty of cock on hand for him. He may have a useless cock, but he knows how to work one. He is an A-class cock sucker and can drain balls like a pro, just like I taught him. One cock is never enough though. I have to make sure my fag boy has multiple dicks to give him multiple loads of cum. He takes whatever I throw at him. He loves dick and loves to have his cunt fucked but what he really loves is pleasing his mistress. He knows if he’s really, really good he gets a chance to lick my pussy and make me cum. He’s such an obedient little fuck. He takes it all and keeps cumming back for more abuse!

Let’s play dress-up!

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I see how you stare at me in my lingerie when I am getting ready for a date, daddy. I used to think it was my tight, little teen body that got your attention till I caught you one day in my room.

I came home from school early and saw that you were home. I thought I would be in trouble for ditching but then I saw it! You were in my room touching all my pretty panties, bras, camis and stockings. You were cooing and your little phone sex daddy dick was hard.

When you turned and saw me, you tried to come up with an excuse but your Princess knew better. My step-daddy is a sissy boy. I wondered just how far you would want to take this but unless you wanted me to tell mommy it was pretty much up to me.

I called one of the big black football players and asked him if he wanted his huge dick sucked. He said he would be over in an hour. Looks like it is time to get daddy dressed up all pretty and show him what it is really like to be a girl!

Playing Dress-up

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Date night is a very important night, I think. The most important night of all. When a girl gets to look good, and please her man, preparation is everything. First, a long, hot bath, to get nice and relaxed. And, of course, shaving. Under the arms, the legs, and the crotch. I have got to be nice and smooth for a nice, sexy man. After all, this date could end up getting rather physical, and being nice and smooth all over is very important. Men like a girl who is smooth and soft.

After that, hair is important, even if it is going to get all messy later, when things wind up in the bedroom. They always say “bedroom eyes”, but I think that “bedroom hair” is better. “JBF Hair”, we called it growing up. “Just Been Fucked”. All messy and tousled, from when he’s been pulling on it, from when he switches positions. But still, hair has to be perfect before the date, all perfectly coifed and styled.

Then, makeup. Oh, there’s so much makeup, so many ways to look sexy for a man. Mascara and eyeliner, to give that perfect doe-eyed look (and looking so sexy when it’s runny, from giving a deep, sloppy blowjob); lipstick, lips so perfectly painted and kissable (which will also look good wrapped around a cock!); eyeshadow and blush, to add a bit of mystery to the whole look. And nails, both fingers and toes, trimmed, filed, and painted. So dainty, so delicate, so perfect to dig into his back during sex.

Then it’s time to get dressed. Sheer, silken stockings, rolled up smooth, tanned legs; a pair of scandalously-small panties, to frame a lovely, fuckable ass; and, of course, the quintessential “little black dress”. A pair of nice, strappy high heels, and… perfect. And there’s a knock on the door; that must be him.

Go ahead, sweetie. Look at yourself in the mirror. Look how pretty you look for your date. You almost look like a real girl. You’re not a real man, so you’d better at least pretend to be a girl. He’s going to be using you like one, that’s for sure. I’m sure you two will have lots of fun on your “date”.

Little Girly Steph

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I have magically turned one of my callers into a prissy little girl. It all started out slowly with him playing with his girlfriend’s panties. He seemed to like the feel of them on his cock, well when he had a cock, LOL. The more he called the more we experimented with his girly side.

Soon it was time for a name change as Scott isn’t very girly. Now his/her name is Steph. Now mind you he still loves pussy, especially when he gets the privilege of tasting his Princess Amanda.

After several sessions it was way more than panties. Steph shaved her legs, leaned how to apply makeup and dressed in full sissy slut for me. What do you think came next? Just because Steph isn’t into men doesn’t mean she doesn’t love to have her pussy filled with a big ole strapy!

Do you have secret desires that you hide from the rest of society? Then call Princess Amanda to get your fill of whatever floats your boat!

Lovers Of Lace

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A certain quiver in your voice lets me know that you have a puny cock. I also know you desire to give up your freedom? You wanna know the thing I enjoy most about playing with a little pathetic cock like yours? The power I have over little men who are begging to be used. I will always have panties on so that the next good little boy has the honor of rubbing one out into something that was so close to my tight pussy.

I love to leave a pair of my panties behind at the gym. Right in front of the mens locker room. I like to think about what horny man will find them later and stroke off his cock inside my dirty panties.

Are you worthy enough? You should find out.

I dare you panty boy!

Aubrey

Toy Box Fun

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I have my toy box ready for you. It’s time we stop the lies, stop pretending. It’s time for your transformation to turn you into my cum dumpster. I’ll be training you to take every size cock you can imagine. Stretching all of your holes making them mine. I’ll know when you’ll be ready to submit, that’s when we’ll take out my biggest and thickest strap-on. After all the lessons, you bow down and serve me. I take my strap-on and shove it in your mouth. I watch as you gag and tears roll down your face. Your a big girl sissy now, take all of it in your mouth and deep throat it. Show me you can take it. Let’s complete the transformation. I know how bad you want to suck on a big, hairy cock and having him bend you over, spreading your ass open. Letting a real man fill up your sissy holes. You’re going to make a great cum dumpster. Are you ready to become who you truly want to be?

Celebrating

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I was going to my closet to pick out the sexiest, sluttiest outfit I can find for my sissy slut. I was surprised when she came home early. I had given her multiple tasks to complete before her big party tonight. She thinks its just a small get together with a few neighbors. Little did she know, I invited her co-workers, a few of her friends. They all adore her in some special way. I poured myself a cocktail and made myself comfortable while we did her makeup and hair, she looked absolutely stunning. I then held her hand and took her downstairs where I invited our friends. I instructed her that she will be pleasing the men first. She was going to be on her knees letting them fuck her face, then letting them fuck her tight, sissy hole. The ones that seem a little shy I instructed her to jerk them all the way off until she had loads of cum all over her sissy face.
We were celebrating our one year anniversary with a glamorous bukkake facial. I could see the excitement in her eyes and I knew her clitty was twitching at the idea of being used and humiliated by all of these men. I watched as she was passed around with cum dripping down her face. She looked absolutely fabulous, she was a hit at the party.
We’ll definitely be doing this again!

Faith

Doing it All For Me

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I adore when my cock whores and panty sluts write stories for me about our calls. It pleases me to read and post them. Pleasing me is what it is all about, is it not?

I felt like I could feel you sitting on my lap, wiggling around & doing that wicked laugh of yours knowing what you were doing to my little clit.  You leaned in so close that my nipples started to go hard (and they really did).  I loved how you did my make-up and the dress you picked out for me.  Then the scene you picked out for me to be your whore & an adoringly one, walk up to the 2 studs that you just knew (goddess magic I guess) had the longest and thickest cocks and have them follow me, right behind you, up into that private bar area.  And you seem to have one in every bar in town.  I’m sure that all the bar owners are as mesmerized by you as I am.

Then came my big moment.  I knew you could hear the strain in my voice as I answered you each time.  Then when you told your Dani that it was time for her to cum, I shot such an explosion of cum that it had to go 18 inches into the air.  I know it made quite the splash when it finally came back down.  I knew you were happy with your personal (and hopefully best) cock sucking fuck whore in your harem.

Bring Your Daughter To Work Day

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Your transformation is now complete. You have become my cute little princess. I always wanted a pretty girl!

Your bedroom is decorated in pink. You now have your own panty drawer filled with every color and style of panties, but of course, you have your favorite panties. You have your little pink silk nightie and a closet full of pretty dresses, skirts and tight little tops.

Mommy loves showing you off to all of my girlfriends. We have “Girls Night” every Friday night at our hose. Mommy’s girlfriends love to spoil you and love to play with you! You are just so adorable! We cannot keep our hands off you!

Tonight, you have an appointment at the salon. We need to get your hair and nails done. You have a big day ahead of your tomorrow. Instead of going to school, Mommy is going to take you to work. You can spend the day with me and I can show you off to my Boss and all of the pretty ladies at work!

Doesn’t that sound like fun?

Mommy Morgan