It was so humiliating. A store security guard caught me walking out of the department store with a pretty, expensive French bra, garter belt, panties and stockings set. I was ushered into the office of the store’s chief of security. I was scared. I was a teenager. It was the first time I had ever been in trouble.
But I couldn’t help myself. I’m pretty and I like to wear pretty things. I couldn’t afford the lingerie, but I didn’t need to steal it either. I don’t know what possessed me to do it. Perhaps it has something to do with my secretive nature. I have so many secrets. My whole wardrobe, actually, is a secret that I keep hidden until I find an occasion for dressing up. Likewise, my make-up, my perfume, heels,the falsies that fill my bra, all secret.
But I got caught. There I was in the security office. I was crying, my mascara running down my cheeks. The security chief took the bra and panty set from the guard, sent her on her way, and closed the door, leaving the two of us alone. The chief was a very large, muscular African-American man. I am a slender, petite, mixed race Asian-Caucasian.
“What is your name?” he said.
“Chrissy.”
“Last name?”
“Lee.”
“My name is Mr. Johnson. I am the chief of security here. I need to ask you a few questions. Why did you try to steal from the store, Chrissy?”
“I don’t know,” I sobbed.
“Stealing is a crime, Chrissy. I can call the police and they will be here in a matter of minutes, leading you out of the store in hand-cuffs and taking you to jail.”
The tears streamed down my face. “Please,” I said choking, “Please, don’t. I’ll do anything, please.”
“Let me see your driver’s license, Chrissy.” I fumbled with my purse, opened my wallet and produced my ID, which showed I had just turned 18.
Mr. Johnson looked at it and I could see his eyes widen.
“Christopher…Lee. You are a boy.”
Busted. Now I was really frightened. I thought maybe I could also be arrested for dressing in women’s clothing in public. I was too frightened and upset to speak.
“Do your parents know you are walking around dressed up and looking like a girl?”
“My Dad doesn’t live with us. My mom doesn’t really pay attention too much.”
“I think you might find the jail experience pretty rough,” he said. “Those guys would eat a pretty boy like you alive.”
“I… I… I… j…j…just can’t go to jail,” I stammered.
“But you’ve committed a crime, Christopher. You have to be punished when you commit a crime.”
I got to my feet, though I was wobbly on my high heels. I was wearing a button down top that I had tied right under my fake breasts so that my slender waist was exposed showing off my sparkly belly button bling ring. I like walking in the mall wearing sexy clothes and making all the boys’ heads turn as I strut by.
But now I was a mess. My make-up was totally smeared, my hair was hanging limply. Mr. Johnson got up from his desk, and sat on a sofa by the wall. He sat there with his knees wide apart. He motioned me to come to him. I walked closer. He put his hands on my hips and moved me closed still so that his knees were on either side of me. Then he slid his hands down the sides of my legs, then at about the knee, moved his hands to the inside of my thighs and moved his hands up, under my miniskirt and lightly brushed my crotch, just long enough to confirm that I was, in fact, a boy. He brought his hands from under my skirt and then unbuttoned and untied my shirt. He let it fall off my shoulders.
“So, these are not real, I’m guessing.” Out spilled the falsies, revealing my flat chest. He brushed my hair out my face. Then he unhooked my front-clasping bra and pulled it off, leaving me standing only in my mini skirt and heels.
“I need to check if you are wearing stolen goods, Chrissy. Standard protocol. Take off your skirt.”
I unsnapped and unzipped my miniskirt, letting it fall at my feet, and then stepped out of it. And, yes, I was wearing a tiny black thong with the price tag still on it.
“Chrissy, that’s stolen property. The courts and the police will punish you in a way that will destroy your life.”
I burst into tears, shaking my head, really my whole body shaking. I totally fell apart to the point where I could hardly breathe.
“Okay, okay,” Mr. Johnson said. “I think we can handle your punishment privately, right here between the two of us. Just us. No word to anyone else, ever. Understood?”
I looked at him with my doe-like mascara-run eyes and nodded my head as I choked back little sobs.
“Come closer.” I did as I was told. “Lay across my lap, Chrissy,” Mr. Johnson said as he grabbed a handful of my hair and pulled me down. I laid my slender body face down across his lap with my cute, round buttocks raised, awaiting my punishment.
“You have been a very bad little girl, Chrissy,” Mr. Johnson said as he still held a handful of my hair with one hand and with the other he squeezed and stroked my young, tight derriere. His hand lightly massaged my uplifted bottom. “This is going to hurt, young lady.”
I squirmed on his lap and adding to my embarrassment, my cock suddenly hardened, pressed against his thighs. He pulled my thong just to where my leg meets the swell of my ass, exposing me, and then I felt and heard it–a loud, burning smack, as his open hand slapped my bottom. I gave out a high pitched yelp.
“You little bitch, we can’t have you screaming here.” he yanked the thong down my legs and stuffed it in my mouth. His left hand was now over my panty-stuffed mouth as he proceeded with hard spanking of my poor young bottom. Tears ran down my face, I struggled, but I was helpless in his strong arms, and my cries were muffled by the thong that filled my mouth. My cock was fully erect and hard. And so was Mr. Johnson’s. I’m sure each of us was feeling the other as we rubbed against each other. Slap, swat, slap, he peppered my buttocks with his open hand. My muffled shrieks turned to whimpers.
My buttocks were scalding hot, inflamed, bright red. Mr. Johnson pulled me up and off his lap, but I sank to my knees, crying, spitting the thong out of my mouth, heaving for breath.
“You’re such a little pussy. Get on your feet and put that stolen thong back on,” he demanded. Shaking now in pain as much as in humiliation and fear, with trembling hands I pulled the thong back up my legs, though my hard cock poked up from the low waist band.
He handed me his handkerchief. “Wipe your face, Chrissy, brush your hair, and re-apply your make up. I stumbled back to my purse, got my make up kit and went to a mirror on the wall. I faced the mirror, my back to Mr. Johnson. In the reflection of the mirror I saw him admiring his handy work. I arched my back and thrust out my reddened buttocks as I leaned toward the mirror. I love putting on make up and think my face is my nicest feature. I applied lipstick, puckering my lips, then the eye liner, mascara, shadow, a touch of rouge. I felt Mr. Johnson’s eyes on me as I caught his reflection in the mirror. I saw his eyes move from staring hard at my ass to looking at my face as I transformed it in the mirror. I liked that he was watching me apply eye make up. No one had watched me doing that before, and it felt sexy.
“Even if you don’t have tits, you have a sexy ass and a cute face, Chrissy, a lot prettier than most girls.”
He watched as I brushed my long hair, fluffing it, making it cascade around my shoulders.
I turned to face him. I batted my eyes, showing off my long lashes now that everything was back in place, eye make up no longer running down my cheeks. I am half Thai, Amerasian, and my face is naturally feminine and with make up is beautiful. My eyes are almond shaped, dark, and with shadow I can flirt pretty outrageously and love doing just that. I have pouty lips that are made for lipstick. A little rouge on my cheeks completes the pretty, feminine picture. I easily pass as a pretty girl.
“I am now going to video you wearing the stolen property. He took out a video camera. “Walk back and forth in front of me,” he said. There I was in wearing only a thong and high heels. I walked back and forth as Mr. Johnson filmed me. I felt myself responding to the camera, putting an extra little sway in my hips as I walked. My buttocks were still smarting with hot pain, but it felt like a glow that created a indescribable pleasure mixed with the hurt.
“Now put on the other stolen goods,” he said. He handed me the French lingerie set, but withheld the French panties. “Keep the thong, put on the rest.” I took off my heels to roll the stockings up my legs. Then, I attached the garter belt around my waist and clipped the stockings on. I put on the fancy, black bra with red lace highlights. I quietly reached to my discarded bra, found the falsies and put them in the French bra to fill it out.
“Walk,” he commanded, as he started videoing me again. “Swing those hips, Chrissy.”
I did the super model runway walk that I had long practiced, my feet crossing with each step.
Mr. Johnson stood up. He had a tripod and now set the video camera to face the sofa. I could see a huge tent in his pants. Then, he walked to me. He took me by the hand, and led me in front of the video camera. He took my head in his strong hands, his fingers lacing into my long silky hair. He tipped my head back, and kissed me. My lips parted and he worked his tongue muscle into my mouth. I felt myself melting as his hands moved down my back and cupped my tight, pretty, but still smarting ass. I let out a deep moan. I’m sure he could feel the heat of my reddened buttocks on the reddened palms of his hands.
Mr. Johnson grabbed a handful of my hair and pulled me so that I swung around and now faced away from him. He whispered in my ear. “It’s time for more of your punishment, Chrissy.”
“Y-y-y-es, Sir.”
He pulled me close to him and I could feel the hard swell of his club-like cock against my tight, hot round little butt.
He worked his hands inside my bra and began pinching my nipples. It hurt, but as soon as he did it, my own cock popped straight up again, sticking out from the front of my thong. His teeth sunk into my earlobe. I squealed in pain, and writhed, but he just pulled me tighter against his body. He yanked me over to the arm of the sofa and threw me across it so my pretty buttocks were again pointed skyward. One of his hands was on the back of my neck, pushing me down. I could hear him fumbling with his pants with his other hand. He kicked my legs apart and stepped closer. I felt his huge, hot, meaty cock hard up against my ass cleavage. He tried to penetrate my tiny, tight little virgin hole, but I was tense, my butt still throbbing in red-hot pain, and not in any way ready for an assault by such an enormous thing. I begged and pleaded. “No, please, no, Mr. Johnson, You’re gonna split me apart, No, no, no, oh, oh, no, please.” His cock, slick with pre-cum slid up and down my ass cleavage, but no farther in me.
Mr. Johnson stepped back, grabbed my hair and spun me around the other way, so I was now facing him. He pushed me down onto my knees. “Suck it, baby,” he commanded.
I was face to face with a monster of a dick. I was greatly relieved that this baseball bat was not forcing its way into my ass, but I didn’t think I could begin to take fit more than a small portion of it in my mouth. He held the back of my head and forced me to take his monster cock deep in my mouth, pushing into my throat, so I was gagging and gasping for air. My mascara became a mess all over again as tears again ran down my cheeks.
I looked up at Mr. Johnson as he fucked my mouth, my eyes begging him to relent. I was grunting and gasping. Mr. Johnson was grunting too as he thrust his cock deep into my mouth. I was sputtering, gagging, desperate.
Suddenly he grabbed me by the hair and dragged me over to the sofa. Mr. Johnson flung me face down on the sofa, then straddled me. He opened up the drawer on a side table, and much to my surprise he had a bottle of lotion. He slathered lotion on his monster cock and squirted a big gob of the cool lotion on my burning hot bottom and between my ass cheeks. “You need to learn to relax, honey child, and take Daddy’s cock like a good little girl,” he whispered in my ear. My head was spinning from the confusing and exciting mix of Mr. Johnson’s power, control, strength, and dominance and little signs of gentle tenderness. He did feel like the Daddy I never had and always wanted.
“Oh, Daddy, please make me your pretty baby.”
Mr. Johnson gently massaged the wet, cold lotion on my round ass cheeks, bringing great relief to the sizzling hot skin from his spanking. I moaned in ecstasy and relief as he squirted more cooling lotion on my poor little bottom.
I started feeling dreamy and relaxed. That ended suddenly, however, when Mr. Johnson jammed his middle finger into my bottom. It felt huge. He began working it around, pushing it in, pulling it out, rhythmically, getting my hips to move in sync with his hand. His other hand was cupped around my throat, making me feel totally and completely at his mercy. He could squeeze and kill me in a second, he was meanwhile giving me the most intensely painful pleasure I had ever experienced because the moment had come when he slipped out his finger and the next thrust was his thicker, harder cock penetrating my virgin bottom. I couldn’t help but yelp out a scream. His hand moved from my throat to my mouth and he used it to stifle my screams. I was in pain, yes, but the screams were as much in pleasure as pain.
“Take your punishment, little bitch babe.” I gasped and cried. More thrusting. “Slutty little girly thief.”
“Please, Daddy, no,” I begged. But he kept up his thrusts and my only means of survival was to join his rhythm and move in unison with his in and out penetration of my boy pussy. Although relaxation was the farthest thing from my mind, I began taking deep breaths and consciously relaxed my sphincter muscles
“Yes, Daddy, do me, Daddy,” I was completely infatuated with the feel of Mr. Johnson’s big hard cock penetrating my virgin ass. I wanted nothing more than to submit to his power and to feel his passion. I was, indeed, Daddy Johnson’s little slut.
He thrust deeply, his body rocked and spasmed as he came in giant spurts deep in my boy cunt. He rolled off me. I couldn’t help but gasp in admiration at the size of his cock and the gorgeousness of his muscular, dark body.
“Dance for the camera, Chrissy.” The video camera was still running. “Use the lotion on yourself.”
I began a slow belly dance, all hips, as I smeared lotion on my slim torso, my nipples, and down until my hands found my own hard cock. I stroked myself as I swayed my hips, feeling so sexy under Mr. Johnson’s gaze and with the camera recording me. “Cum for me,” he ordered. I swiveled my hips as I stroked my cock. He kept videotaping as I brought myself to orgasm.
“Clean yourself up, Chrissy. And I’ll pay for the lingerie you stole and give it to you as a present.”
“Thank you, Mr. Johnson.”
“When we’re alone together, Chrissy, and I hope we will be many time again, call me ‘Daddy.'”
“Yes, Daddy.” I batted my eyes and gave a little curtsy.
“You also need to go to the doctor’s and get a prescription for female hormones. I want my baby to have pretty breasts.”
“Yes, Daddy, I’d like that, too.”
It was the beginning of a new life with a Daddy now in my life for the first time.
Proudly signed,
Willing Wimp