The Boss’s Son Ch. 03 - Lines Blur

He looked at me, seeing the anger on my face, Terry asked in that girlish pleading voice, "Are you going to hurt me?"

As I looked at Terry, the lines then became blurred. Was he wanting to be treated like an 18-year-old teenaged boy or girl, both or what?

She leaned forward and just above a whisper, she added, "You can if you want too. I like pretending I'm being forced, made to do stuff. You can do whatever you want."

She leaned back, looked up at me again and bit her lower red painted lip. This time with a kind of smirk on her face.

She likes to role play being the helpless little girl? Is this how the boys at school treat him, use him?

I stood there for a minute, looking at her, trying to digest what she had just said, what I was thinking and what I was going to do. Well if he wants to be the hapless little girl, so be it.

My reaction surprised both of us.

I reached out with one hand and grabbed the little teasing bitch around the top of her throat just under her chin. She gasped and her beautiful brown eyes opened wide. My grip on her throat, not hard enough to choke her, but enough to cause her face to turn red and for the veins in her neck to bulge.

She reached up, her hands grasping my wrist as I lifted up. The top of the soles of her high heel shoes touching the floor. I pushed her backward, her toes sliding across the carpet.

She whined, her eyes pleading, "Please Mr. Miller. Stop. What are you doing? What are you going to do to me?"

My arm straight out, I grinned at her, pushing until her back slammed into the wall. Her frail body jolting to a stop.

I released my grasp from around her throat. Her grip on my wrist loosened as her heels hit the rug. I gave her a stern look and ordered her, "Sit down Terry."

Tears formed in the corner of her eyes as she obeyed. She slid down the wall, the back of her head pressed against, causing her hair to stream up behind her.

Again, she pleaded convincingly, "Please Mr. Miller. Please!"

For a brief second, I thought that maybe I was being too rough, that this wasn't what she meant by "hurting" her.

I watched as her tight little ass hit the floor. Her knees were bent and slightly separated. Her feet on the floor, dress pushed up to her waist. Her exposed perfectly thin thighs and calves made me want to go down on her again. Running my mouth and hands all over them again.

His thighs slightly apart I could see his tiny stiff dick. Jesus, this sweet little sissified fag was hard again and his cock was pointing straight up at me. So much for me thinking I was being too rough. He was getting off on being treated like a helpless little girl about to be violated, used.

I took off my suit jacket and tossed it aside and glared down at him. "Unbuckle my pants, girl."

She looked up at me with a pained expression on her face. As she reached up and started to undo my belt buckle, she again begged, "Please Mr. Miller, don't make me do this. Please."

I smiled down at her, "Don't worry Terry, I'm not going to make you do anything you don't want to do." She looked up at me with a puzzled look on her face as her red coated fingernails fumbled with my belt. Her expression changed and her eyes opened wide as I added, "I'm going to force you to do it."

My buckle opened, she didn't need my instructions to unbutton, unzip and pull down my suit pants. My light blue boxers tented, finally some freedom for my trapped growing cock.

She pushed my pants down to my knees, reached up again putting her painted nails on the waist band of my boxers and tugged down and over my dick. She let out a slight gasp as my cock sprang up at her face. I'm not a "gifted" man, my circumcised cock is a bit longer average, 7" and when erect a girth wider than most. Jackie always said, that at first sight of my stiff cock, it would make a girl give pause.

This little sissy boy was no exception. She wasn't looking up at me now, just straight at the bulging helmet of my cock. A drop of pre-cum oozed from the tip.

Looking down at this beautiful girl, I moved the head to her ruby red lips. They parted. I felt her teeth for a brief instance and then her tongue flick off my pre-cum drop from my pee hole.

Before she could enjoy the taste, I pushed the blood-filled head of my cock past her lips and teeth. Her eyes widened. Her jaw stretched open. My invading cock forcing her head to be pinned against the wall.

She gasped for air around my cock. I pushed deeper into her face. Her small hands moved to my thighs, pushing back on them trying to stop my assault on her mouth. I shoved my cock to the back of throat. She gagged. Saliva leaked from her mouth, down her chin. I eased back a few inches and then just started to hammer her head. Each push, ramming it into the walls. Mascara-stained tears now streamed down her face. She gagged loudly with each thrust of my rigid dick. Now a steady flow of drool dripped off her chin. Her red nails digging into my thighs. Her knees parted wider, giving me a fresh nee look at her thin, nylon covered thighs.

My tie dangled below me, swaying back and forth to the rhythm of my rape of this little teenaged girls' face.

My voice, a mix of anger and lust, shouted down at her, "You fucked my face bitch, didn't you? Well let me show you what a real face fuck is!"

My anger fueled by my lust for a boy. I'm not a queer like this little faggot. I'm not. But I'm fucking this 18-year-old boys face.

The thoughts made me pump my shaft harder and deeper into her. Her head banging against the wall with each push. Her soft, silky hair, flayed around her head, framing it.

I pulled my cock back, just leaving the engorged helmet in her mouth. She sucked on it, as if trying to coax my cum from my balls. I could feel her tongue licking up and down my pee slit, tasting the pre-cum I was sure was flowing from the tip.

I could feel my climax building, but I didn't want to waste my cum on her mouth and face. I pulled my dick out of her indented cheeks and mouth. She looked up at me. Her large brown eyes questioning why I had stopped raping her head. Her mascara-stained black tears, etched down her checks, mixing with her thick, clear saliva coated chin, down her tapered neck onto her pearl necklace and top of her dress. God, she looked like a perfect little slut.

I reached down, placed my hands under her wet armpits and lifted her up to her feet. I leaned down, kissed her tenderly on the mouth tasting the sweet tartness of her saliva mixed with the saltiness and bitterness of her mascara-stained tears.

I then spun her around facing the wall. I grabbed ahold of her hips, pulled the towards me, forcing her to put her hands against the wall, finger flared, to balance herself. When her arms were stretched straight out, I stopped. The smooth, flawless skin of her bare back glistened with sweat.

Her breathing was heavy. Her soft perfume mixed with our sweat. I lifted the back of her dress up over her tight, smooth softly rounded ass, letting the hem rest on her waist. Her ass perfectly rounded, her skin was taut and flawless.

She turned her head and looked at me. "Oh God, no, Mr. Miller, you're too big. Please, I can't take a cock that big."

I moved my girder stiff dick between her, firm ass cheeks and ran my slick drool covered cock up and down her crack. She cooed, enjoying the feeling.

Then in one motion, I grasped the base of my cock, placed the wet tip of the helmet against her small glitched asshole and pressed forward, forcing my way past her sphincter into the dry flesh of her ass.

Her hands became fists against the wall as I penetrated her ass. Her scream filled the room. The sound only added to my craving to have all my cock deeper inside her.

I pushed into her, impaling her. She was sobbing loudly, her head down, outstretched arms and hands holding her up. I started to saw my cock back and forth inside her ass. Her crying refueling my lust and anger. Her hair on the side if her face moving back and forth to the hammering I was administrating to her sweet girlie ass.

I looked down to watch my thick dick disappear into her. I slowly inched up into her one more time until I was completely imbedded inside her ass. My cock expanded and my cum exploded into her. A warm wetness immediately engulfed my shaft and the inside of her ass. I felt her asshole contract around the base of my cock.

Fuck! The little slut was cumming too! Without her small dick being touched. The second wave of my cum escaped and I started to easily pump my cum coated still rigid dick in and out of her.

She gasped with each push, still sobbing. Her cock spasming cum onto the wall and carpet.

I held onto her hips, keeping my cock imbedded in her ass until it was completely drain and both our contractions stopped.

I let go. I pulled back and my cock slowly losing its firmness slipped out of her ass. She sobbed and slumped to her knees as her hands slid down the wall.

I realized my tie was still tied, my white dress shirt buttoned, my suit pants draped around my ankles over my shoes. I was drenched in sweat.

She turned on her knees to face me. Looked up, her pretty face covered in smeared make-up. Her ruby red lipstick smudged away. Her brown eyes inviting as ever.

She lowered her gaze to my limp cum covered cock, fresh from her ass, hanging below my dress shirt. She raised up on her knees, took one hand and cupped her tiny fingers, around my balls. Terry leaned up further and sucked my flaccid jizz coated cockhead past her small pink lips into her face.

My cock twitched but was unable to respond so soon. I just stood and enjoyed the vision and feel of this lovely young lady washing and cleaning my cock with her tongue and lips. Teasing me by scraping her teeth along its length once or twice. Her sweet, sexy, eyes looking up at me. Done, she let my clean softening dick slip out of her mouth.

Again, I reached down. placed my hands under her warm, moist pits and raised her to her feet. Kissing her tenderly on the mouth, this time tasting and smelling my own cum and her ass. Hugging her, her soft, tender, body seemingly melting into mine.

We hugged and kissed for not long enough when I eased my embrace and took a step back.

I looked down and was shocked back to reality. My cell phone stared up at me from the floor where it had fallen from my suit jacket's pocket. I had it on silent mode and there were over fifteen messages from the office plus half a dozen from Jackie. I looked at the clock by the bed. Fuck! We've been at this for over four hours. I quickly pulled my pants up, buckled them, grabbed my phone off the floor and picked up my jacket. Terry standing there motionless watching me.

Jackie messages were asking me if I was 'okay' and the office was trying to get hold of me and calling her to see if she knew where I was. There was even a message from Mr. Blake asking if I had found the disks.

I looked up at Terry. She was just staring at me. She looked confused, not really understanding what was going on. I walked over to her, gave he a soft kiss on the mouth. I didn't know what to say. I just shrugged my shoulders, "I have to go."

She sighed and asked, "You won't tell my dad, will you?"

I looked at her, a pain expression on her face. "No Terry, your secret is safe with me." I kissed her again and left.

Before I drove off, I returned the boss's text saying I would send the files as soon as I got back to the office. I texted my assistant and Jackie that everything was fine. I was caught up in traffic and would be back as-soon-as I could. I repeated to Jackie, that I was okay and I'd explain later.

Explain later? Explain what I just did? Why did I tell her that!? Oh, fuck.

Next: Jackie's turn.