Naughty Schoolgirl

One of my favorite roleplays is the naughty schoolgirl. I just love to play the wicked little girl who Dominates dirty old men. I use my youthful appearance to manipulate men to do my bidding, and I make them endure humiliating activities to please me. When those dirty old men are with me they have to play my games!

My most recent schoolgirl session was with a professor the other day. I wore my grey jumper, white collared blouse, white knee socks, white cotton panties, and my soft soled maryjanes. I wore my hair in a ponytail with a satin bow.

I told him that he had to do everything I told him to do otherwise I was going to tell my parents how he peeps under my skirt when he thinks I'm not looking. I sat him down in a chair and bound him with bondage tape by the wrists. Then I wrapped the tape around his mouth so he couldn't make any noise. I sat in front of him and spread my legs wide, showing him my cotton covered pussy. I asked him if this is what he was always trying to get a peek of, and he nodded; eyes transfixed on my fingers playing across my pussy lips.

Then I turned around, lifted the hem of my jumper up and showed him my ass. I gave my bum a playful little slap, and caressed my ass cheek, tugging my panties into my crack. I asked him if he liked my ass, laughing when he nodded affirmatively again. I shook my butt at him, teasingly, and lowered myself into his lap. As I ground my ass into his crotch I told him what a filthy pervert he was, and how i really should tell on him and get him fired. I turned around, laughing, and straddled his lap, my dress bunched up around my hips, and rubbed my pussy down on his hard cock straining against his khakis.

I leaned over and licked the tape that encased his mouth, as I unbuckled his pants. I slid off his lap and brought his pants down around his ankles. The crotch of my panties were damp from teasing him, and I could see his erection slipping out of the flap of his underwear. I laughed at him for getting so turned on by such an inexperienced young girl.

I told him that I was getting all tingly between my thighs, and that I had the urge to rub it against something. I hopped back on him, putting a leg on either side of one of his thighs and began to move back and forth. I said that I wanted a pony ride from him, and I began to bounce on his leg muscle, making his flesh wet thru my the thin piece of cotton separating his skin from damp cunt. His cock swelled even more, and I whispered in his ear how I knew what he wanted, that he thought about putting his cock into my tight virgin cunt.

I stood up and said to him that I was giving him a choice. He could either jerk off in front of me and show me what it looked like when a boy cums, or he could lick my asshole. The look on his conflicted face was priceless! He had such a difficult time deciding what to do, but he finally settled on getting his tongue in my asshole.

I turned around and bent over the bondage bed, lifting the hem of my jumper up again revealing my pantie clad ass. I told him to start at my ankles and work his way up. He began by sprinkling kisses up my calves and then over my thighs, eventually making his way up to my ass cheeks. After burying his face into to crack of my ass over my panties, I told him he could pull my panties down and kiss my bare ass.

Once my panties were removed, he dove between my cheeks and licked my pink rosebud. He moaned and groaned into my ass, breathing in my scent, tasting me deeply. My asshole was soaked with his saliva, and I could feel my pussy lips swelling with desire. I pushed back into his face surrounding his face with flesh. His hands slid up cupping my ass cheeks spreading them a bit more so he could lick deeper into me. I scolded him for being so nasty, for liking to lick little girls. I reached around and gave him one last shove of his nose into my ass, and then sent him on his way with a wicked laugh and full balls!

Casual Friday

So, I was wondering if Big Boss was ever going to get around to reacting to my little present. I went all last week without hardly any contact with him at all. He barely paused at my cubicle to say hello, like he usually does.

But then I realized I'm in charge of this, so I took a giant leap forward.

At the end of the day on Friday I walked into his office and said I needed to speak to him, and closed his door. I sat in the chair in front of his desk, and said that I believed he had something of mine.

As I said this, I spread my legs open and showed him my bare pink slit. I wanted him to see everything, every crease, every rosy pout, the dampness of my pussy. I ran my hand up the inside of my thigh, and tugged on the graters at the top of my stockings, and spread a little wider. He couldn't take his eyes off me as he reached inside of his desk and pulled out the little scrap of red silk I had left in his office.

I told him to come around the desk and hand it to me. And his face got a little red as he walked around towards me. I didn't close my legs when he reached out to hand me the balled up fabric in his hand, but I didn't reach for the panties. I told him to get down on his knees in front of me, and to be honest, I wasn't sure he would. And then there he was, on the floor, his face a foot away from my spread pussy. He was getting a very good long look as I continued to run my hands up the inside of my legs, over my nylons, and slipping my fingers under my skirt.

He licked his lips when I told him I wanted him to slip the panties onto me. I held up my left leg, my foot right in his face, and he hooked the undies around my ankle. I lifted up my other foot, and he repeated with the other side. I stood up in my high heeled pumps, bringing my pussy right in front of his face. His nose even bumped my clit, and I'm sure his head filled with the scent of my desire. I held up my skirt, and he pulled the panties up over my soaked slit.

I turned around to give him a nice view of the seams in my stockings and my round ass, and told him to adjust the thong in the back so it went straight up the crack of my ass. I could feel his fingers shaking as his fingertips brushed along the smooth crack of my creamy ass, and I bent over to open my ass up a bit. I let my skirt drop when I stood back up, thanked him for returning my panties, and left him there on the floor with a raging hard on pressing thru the front of his pants!

O how I love "Casual Friday"!!! Ha!

On my day off I thought of a way to up the ante with Big Boss. When I got dressed yesterday I wore a silky red thong, a short pleated black skirt, a lacy grey blouse, and a super duper push up bra.

I knocked on Big Boss's office door just as everyone was leaving for lunch to "give him some files", that he didn't really need. We chatted for a second, all innocently, tho I did lean over the desk a bit to give him a look at my cleavage. When I was walking to the door to leave, I dropped my pen, and bent at the waist to give him a good view of my stocking covered legs and bare ass. I wanted to make sure he saw the red thong, so I spread my legs a tiny bit. I heard him gasp as I closed his door behind me! Heh heh!

It turned me on so much to tease him that I played with myself in my car. But I couldn't stop thinking about it, so I played with myself again in the restroom a little later. Then I got an idea, and wiped my pussy with the thong and put them in my purse.

Before I left work I left my soaked thong on the chair in his office! I wish I could have seen the look on his face when he found my underwear in his seat, just imagining him taking them into his hand and sniffing them turns me on. I can just imagine him wrapping them around his cock and jerking off into the red silky material. I hope he gives it a huge load!!!

Sissy Shopping

Yesterday afternoon a Domme friend of mine, Ms. S, and I were chatting on the phone about a novice sissy, Kay, who is interested in femininity training. It seems that the young ladie has been harboring these desires for years, but owing to living with a large family in an extremely conservative part of the country, she's been unable to fully express her true self. We felt she needed our help, so we decided that we needed to take her shopping.

Yay shopping!!

When we got to the mall, our first stop was the cosmetics store so we could choose the perfect colors for our new gurl. Both Ms. S and I have worked as estheticians, so we knew we needed to start with Kay's make-up and skin care first. Kay could barely control her excitement when she saw all the colors there were to choose from, but we steered her first to the appropriate skin care products and proceeded to educate her on the proper way to cleanse and care for her type of skin. After that we allowed her to pick out her make-up, advising her along the way about the best shade to compliment her coloring.

Next was the shoe store. Kay is fortunate in that she posses relatively small feet, and we were able to find her two pairs of shoes that fit her beautifully. The first pair has a low heel, that's going to be her "practice" pair so she can learn how to walk in heels. When Kay first tried them on and attempted to walk down the aisle Ms. S and I couldn't help giggling at her awkwardness. We teased her that she would have to do alot of chores in her new heels in order to improve her gait. Kay's other pair of new shoes she'll have to work up to. Those are her "inspiration" shoes, a pair of red platforms with little ankle straps. So cute!!

Kay looked so proud and giddy following Ms. S and me and to the wig store. Kay swung her bags and pointed at all the things she was going to get once her transformation progressed. Ms. S and I reminded her she still had a long way to go, but we encouraged her enthusiasm (Kay is so adorable!). At the wig store we decided that Kay need a full wig until her hair grew out, and then we could get her some clip in extensions. We left the store with a fantastic wavy blonde wig that fell just past Kay's shoulders.

Ms. S and I had saved the best for last, and we made our way to the lingerie store. I could see Kay's clit pressing against her pants making a slight bulge when she began to touch all that silk and lace. She grew quiet, and reverently ran her fingers across satin panties, lacy bras, and sheer garters. We chose a pair of see thru white panties and bra set and a satiny black bra and thong set with lace on the edges for when she needed to look slutty.

As we made our way to the check out counter Kay looked over at the garters longingly, and we just couldn't resist getting her a pair. We let her pick out which ever one she wanted, and she chose a pink mesh garter skirt with darker pink bows at the hips. She'd obviously been listening when we had told her that pink was a good color for her ( very good gurl!). Of course now she needed stockings, and we picked out one pair of nude nylons and a black pair with seams up the back because every gurl needs a pair of seamed stockings!

When we got home we had Kay give us a fashion show of all her new things. She pranced around the house in her new lingerie and practice heels. Ms. S and I giggled and teased Kay when she danced sexy for us to the music on the stereo, and we tried to teach her how to move like a lady. Kay's going to have to work on that!

We didn't allow her to try her make-up on yet, but we did show her how to use her new skin care cleanser and moisturizers. Soon we'll be able to move on to her cosmetics and hair removal, but she must be patient, and we have to be sure she retains the basics before moving on to more advanced training.

Keep your fingers crossed for our gurl, Kay!!