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

Virgin Holes

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When I need a good chuckle, I look at the collection of all the pictures you small dick losers have sent me. One of them really catches my eye. It’s the smallest shriveled up dick I’ve ever seen.

He’ll never function as a real man, no one wants to play with anything that small. The first time he showed me his pathetic pictures, I couldn’t help but to bust out laughing. I literally had tears in my eyes, it was so funny.

I explained to him many times. Not only is his small worm dick hilarious but his only purpose in life with a dick that small would be serving as somebody’s bitch. Pleasing real men with big cocks.

I was on a mission for him. It was time to get his virgin ass fucked by a massive thick cock and turn him into my cum guzzling faggot. He’s been dreaming about this day since he first realized he needed to put his two fingers together to masturbate.

It seemed very scary for him but I would never let him go through this alone. I let him him feast on my nipples while he opened his virgin hole. It was scary and it hurt a little but I promised him that the pain would always turn into pleasure.

Transformation

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I bet you feel lost and confused at times maybe even wanting the need to feel appreciated and accepted for your natural beauty. I know the desire is aching to come out. You’re ready to show the world how beautiful you are. Come to Miss. Cameron and I will make everything better with no questions asked. I want you to feel like a diva. Let’s get you dressed up in a beautiful corset with a sexy pair of panties. I can see the sparkle in your eye when you slip on the panties, you start to get excited when you feel the material against your clitty. I know, it makes you feel so girly when I take you under my wing. I’m not only going to teach you about make-up and clothes, I’m here to guide you into giving up all of your rights to me. Turning you into my devoted sissy whore who belongs on her knee’s in complete submission. Begging and moaning for more cock. You’re my cock whore and you’ll suck only the cocks that I provide for you. The sight of your pretty pink lipstick smeared all over your pretty face is absolutely priceless.

Your face get’s fucked and I humiliate and guide you in the right direction. Indulge in that hot jizz dripping down your beautiful face. If you’re a good girl, you  know I’ll feed you some more.

xoxo Cameron xoxo

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