Archive for the 'Sissy Lessons' Category

Page 15 of 33

A Panty Boy’s Excitement

Your so excited when you return from the mall with a handful of shopping bags. You can’t wait to tell me about all the things that you had bought. I listen to you beg me asking me if you can please try on all your new panties. With a smile, I agree to let you put the new panties on and walk the walk in front of the mirror. They are actually going to look perfect on you when your on your knees sucking some big, fat cocks. I walk you into a room full of thick massive cocks that are all straining against their zippers waiting to cum out and play. I know what a dirty cock sucking panty boy slut you are. You are so eager to get the first cock in your mouth. I would never just let any cock get a hold of your sweet sissy holes. They need to be the best cocks in town. Get up on the bed and get that sissy ass way up in the air and show all those cocks how you work them deep in your tight hole.

Are you ready to squirt your girlie juices for me?

Mommy Debi’s Little Play Thing

 I decided a few months ago I would love a girly little plaything. Not exactly a girl but close enough for her to be soft and feminine.  A close friend of mine was going away for the Summer and asked if her son could stay with me as I have so much room in my house.  We discussed the situation before she made her plans and she agreed how she always wished her boy had been a little girl.  Jen got special hormone pills for her son the next day.  By the time he came to stay with me he was already showing signs of losing his manhood.

Within a week after his dosage was upped he could no longer fit in his boy clothes as his body was changing.  I came home from work to find him sitting on my bed with girly clothes he just felt he HAD to purchase and a confused yet excited look on his pretty face.  It was time for the talk I had been eagerly waiting for.  I told him to take off all his clothes and take a good look at his body in the mirror. He was very embarrassed but I stroked his blonde hair that had grown down to his shoulders.  “Your mommy has been giving you pills to make you into a girl”, I told him.  I stood behind him pressing my big boobs against his back and kissing his neck. I explained to him that while I loved men I also wanted a girly boy to play with. I began to play with his tiny cock, rubbing it like I would my pussy. He moaned and I could feel him getting wet.

He was excited and ready to try on all the lingerie he had purchased. “Not yet, baby” I whispered in his ear. Mommy Debi is so horny and she needs to feel your sweet soft body rubbing against mine.  He laid down on my bed and I kissed my way down his smooth body. His little boobs were so yummy I could not keep my mouth off them.  I got on top of him rubbing my dripping hot cunt against his. He thrust up his curvy hips and slid his tongue into my mouth. We both came so hard and loud I imagine the neighbors even heard us. Now I have the little girl lover I always wanted.

Is it okay to laugh?

I have a funny new caller. Just hearing his voice cracks me up so bad I get the hiccups. He is a panty boy and I do love my panty boy callers. He likes for me to dress him up sexy and to take him to the airport. Even though I am barely legal he calls me Mistress. I am a very bad girl and some of the time I make him get drunk and try to walk in his stiletto heels. Between you and I, he falls down a whole lot.

Last time was the funniest EVER!! We were really getting into things and other panty boys joined us for him to train. He was so girly even trying to tell them what was expected of them. His voice is not what you would call commanding. Then it happened…..wait for it. He moaned out in his most girly voice ” Tell me to make love to my right hand”.  ROLFLMAO!  Then like a good slut he licked up all his cum.

Let’s play dress up. You know you want to.

Wicked little Amanda

Boys Will Be Girls

Girls can be so mean to little boys sometimes. I always was and that will never fucking change. Jeffrey from across the street is playing house with the girls again. He is wearing pink shorts, a Hello Kitty tee and the girls have put his hair in pigtails with pink bows. It is so very entertaining but since they are young there is a few things they would never think to make him do. I have a few hours to kill so I think it is time he felt what it is really like to be a girl.

The girls have gone inside leaving him alone as usual. “Come over here”, I call to him. Yes, Ms Brianna”, he says shyly. I ask him why in the world he is dressed like a girl. He turns a pink shade to match his bows and explains to me that mommy likes him dressed like that.  “I see, so mommy wanted a little girl, not a boy” I ask him. Then Jeffrey slips and tells me a secret. He told me that he is mommy’s little whore. I had a feeling he was already broken in. Over milk and cookies he tells me about the strap-on mommy used. I make a few phone calls and soon my little sissy boy will have a real daddy’s cock instead of mommy’s strap-on.  A girl needs to learn, doesn’t she?

Dress For Your Mistress

I came home from school and found my step daddy going through my things. My sexy lingerie was tossed all over the bed and floor. I threatened to tell on him for being a pervert but he begged and said he would do ANYTHING if I didn’t tell her. I was still rather confused so I told him to tell me what he was doing before I figured a punishment. He explained he wasn’t perving on me but  he loved to feel pretty and sexy in girly clothes.

I told stepdaddy that to begin he must always call me Mistress and hand over his credit cards. I mean if he is going to wear some of my lingerie then I would need lots more. He offered to take me shopping and was so very eager. He helped me pick out several silky panties, cami’s and bras. I found a few corsets and garter belts as well.

We went to the counter to pay and there was a real cute girl around my age. She said that what a nice step daddy I had to buy me so many sexy things.  “Do it”, I whispered in his ear.  “Please Mistress Amanda, don’t make me say it. It is way too humiliating”, daddy said. I told him he better do it, as the sales girl  was starting to get impatient with a line forming behind us. “These are for me, because I am a little sissy slut”, daddy said. Everyone started laughing. It was so much fun!

Mommy Morgan Has A Pretty New Dress For You!

Your transformation is almost complete.

You are so beautiful!

You are so precious! My Precious Baby Girl!

You look like a younger version of me when you are wearing my panties and stockings. Those special vitamins have given you such a cute girly figure! Your hair is getting longer in the back. Let’s go to the salon, so you can get your hair and nails done today.

When we get home, I have a special, wonderful surprise for you. Your first party dress!  It is a sweet little floral dress. It is tight on top to show off your new budding breasts and the skirt part of the dress flies up when you twirl. It is the perfect dress for my special Princess!

Can’t wait to put in your new dress!  You are my beautiful doll! We are going to have a party with my best girlfriends and show you off to them!  Going to be the Best Party!

Love you, Baby!

Mommy Morgan

In the mood for a panty boy

I’m at home, feeling a little bored and wishing I had a little sissy to entertain me. I love to take those confused little panty boys and play with them. I bring them in and dress them in my pretty lingerie. They try to resist, but I can see that bulge in my silk panties. They love it. The last thing they need are pretty red lips. How can you be a proper slut without red lips? I sit back on the couch, propping my legs up and command them to stroke for me. I want to see them fill my pretty silk panties with creamy cum. Sometimes I’ll invite some of my girlfriends over to watch with me. We sip wine, point and laugh. They always stroke furiously, wanting to cum so the embarrassment will be over…. but I have a surprise for them in the end. Once they shoot their load, I make them take off those panties and clean up every drop…. yum.

First Time For Everything

My step-brother has been having some problems with my parents. He had asked if he could stay with me for a few days to sort things out. When I was going out last night I knew he was going to have some friends over. I was totally fine with that. What kind of trouble could they possible get into? When I got home I was shocked! I walked into my bedroom to find him and his friend standing in front of my mirror wearing my clothes. They had the nerve to wear my dirty panties! I was so mad I made them strip down to nothing but the panties. I took a few pictures just in case I need to blackmail them. It’s so much fun being big sister. I could see that no one at my parents house teaches them a lesson. I sat down on my bed and each of them took turns laying on my lap while I gave them spankings. I was teaching these filthy perverts a lesson. If they want to continue to  play with my clothes and make up they need to ask permission first.

They are only to wear them around my house on the weekends so I can turn them into sissy sluts.

Callie

A Glamorous Transformation

Your beautiful, glamorous, and classy. You’re truly a queen. I have transformed you into a beautiful elegant woman. Not to mention, I’ve trained you to be the best cock sucker in town. So obedient and always ready to please. With a snap of a finger you drop to your knees. Your beautiful red lips inches away from his throbbing cock. Your elegant hands and your freshly manicured finger nails wrapping around his enormous package. I love how excited you get. Your face glows as you look up at him batting your eye lashes while you take him in your mouth like a good sissy slut.

I’m so proud of the woman that you have become.

Faith

Sissy Boy Time

Isn’t it fun hanging out with me? Getting all dressed up all pretty and delicate. I love the black lace panties you picked out. You’re really starting to show your true colors by the way you pick out your clothes now. They are the perfect fit to hide your cock under that sexy red dress you picked out. It know it makes your cock hard thinking about what you would wear this very second. Brand new sheer silky stockings going up your legs, looks perfect and so long and shapely. I know your sexual appetite is building up. I have so much in store for you this weekend. Your just going to have to call me and find out.
Whatever path we go down. I know you will be squealing with pleasure.

~Princess Paris~