[Bi] My Boss's Spanking Appointments

He called me into his office alone once, after work was over and telling me it was to 'work overtime'.

I went in and shut the door. He was more casual, genuine smiles.

"You won't be needing to call in that little girlfriend of yours, cucky. Just you and me this time."

"Y- yes sir."

I sat.

He looked at me and smiled.

"You're going to start squatting more."

Oh no.

I had a feeling of dread.

He nodded. "Yeah. It's important for the company that everybody be in good health, and represent the company best. And with you I'm just not seeing that. In fact I'm thinking maybe your lack is worthy of a bit of motivation. Stand up and come here, Timmy."

I awkwardly stood, walking around to his desk.

He grabbed my hips and turned me, pushing my hands against the desk.

Oh NO.

He gripped my belt and slowly unbuckled, looking me in the eye. He smiled. He pulled it off and clunked it down, before moving his hand to my pants and ripping them down quickly, exposing my boxers. He frowned at them. He put a hand on my ass and looked at me. "You were panties from now on."

I gulped. I tried to speak and he shook his head. "Wasn't a question cuck."

"Y- yes sir."

"Get some nice pink panties, red ones, black ones. Make sure they fit your ass. Measure it, get an exact size, then get a size erring on smaller. That way, well..." He smiled teeth. "Your full potential. And squatting weekly if not twice."

"Yes sir." I said.

"Good." He replied. "Now. Bend over, and arch your back."

He made me, pushing me down anyway. I gulped and panted.

His hand pressed against my ass and he moaned, smiling as he rubbed it. "Although you must have squat at least a little before... this is a nice fat ass cuck, for a straight man. Say thank you."

SPANK

I jumped. The spank felt... good.

Oh no.

It felt good.

"Th- thank you Mister Johnson sir."

SPANK

I was getting hard. He moved to touch and feel up my balls and cock, must have known it would happen because he smiled feeling the small hard-on and laughed.

"Good boy. Fuck getting hard at getting spanked by your boss I just can't... so fucking pathetic. You know how pathetic you are boy?"

SPANK

"Y- yes sir."

"Oh? You do? You're not just saying yes sir? So you do know how pathetic you are enjoying getting spanked by the man who fucks your girl?"

SPANK

I shivered. He groped my cock and laughed, smiling.

I gulped. "Y- yes sir. I do..."

"Well good. Good boy. Now."

He pat my ass and snapped his fingers to follow him. He sat on his chair and pat his legs.

"Come on. On Daddy's knee now."

I gulped. I slowly moved to lie on his knees.

He felt my ass and grinned, rubbing up and down. "You're hard, cucky."

"Y- yes Daddy..."

Why the fuck was I calling him Daddy so much? Why was I so hard?

SPANK

"Good boy. From now on, when Daddy spanks you, just like this - and we might have to do this weekly to see your ass progress. You're going to call me Daddy okay bitch boy?"

"Y- yes Daddy. Th- thank you Daddy."

SPANK

He laughed and moaned, feeling my cock and spanking me with the other, slowly patting my cock and leaving it alone before spanking me again. Slowly, but decisively. "You're pre-cumming. You're going to cum against my leg sometime, boy."

SPANK SPANK

I feel a moan leap from my lips as I kick submissively girly, my cock straining to throb and cum a thick load all out, but the sensation is in my cock not my balls. It's not enough.

"Y Yes Daddy! But- But- I- I can't!"

SPANK SPANK SPANK SPANK SPANK

"You can't WHAT? Be polite."

"Ah! I can't cum s- sir! I can't cum just from getting spanked by you!"

He tilted hi head to me and gripped my chin, before growling lowly at me with his deep voice.

"Suck on this big nigga dick and say that to my face, pussy."

I moved to kneel and desperately unbuckle his bigger belt and pull open his pants and see his big fucking cock spring out to slap against my face. I jumped and looked at it. Bigger than mine by fucking three times.

I slowly stroked it and he-

GRABBED my head and pulled it to the cock, before I had to suck or get prodded as I took the cock in my lips.

"Say it. To my cock cucky."

I looked into his eyes with a glare, as if that mattered any masculinity being fucked away in my mouth. He made me sound stupid as he fucked before I had moments off his cock to speak.

"I can't-"

GLORP GLORP

"C- cum-"

SCHLURP SCHLURP

"To just being spanked s- sir..."

SPANK

"Suck on these big nigga nuts and say it again cucky."

"I- I can't- aghhh..."

He pins my hands behind my back and I feel an aggression I have never been capable of giving to women.

He spanks my ass while I moan - and suddenly stops. That's it.

"You can go now, cucky. Go home to your girlfriend."

I stood and walked out with a red ass, puzzled. I looked at it in his big mirror seeing two big red marks and feeling sickly proud that I had taken so much ****.

Then he called me in again. I squat that week, twice, hurting my legs but hoping it would be enough. He praised me for it but still spanked. No ending to it.

Time and time again. He calls, I go over, he plays Blacked porn and spanks me. But nothing else. No fucking, no sucking, just threatening me.

I bought red panties and black panties and he ordered lace instead. I bought those. He smiled and snapped the panties against my ass tight around it as I revealed them, laughing at the sight of them.

He spanks me, humiliating me, taking videos of it, making me look at the camera, but never makes my face leave the darkness, or fucks my asshole even though there's literally nothing I could do to stop him if he tried.

He just spanks me. I get hard and leak, but eventually I get soft again. I don't cum.

"You've cum with a big, black dick inside a you. Don't ever forget that, cuck."

I go over, and he fucks me. He fucks me up my asshole and spreads it out, feeling like the most pleasurable sensation, everything being taken over and let go. I let go completely and let my bully fuck my asshole slowly and intimately, shoving his bigger black cock up my tight hole getting stretched around it and made to take every little ridge of vein and hard muscle of cock up inside my tight asshole.

And then he cock-kisses my prostate. His cock head pushes and smooches it, massaging up my prostate and slowly, teasingly massaging it. That's all I can say. It's a massage, a prostate massage with a big black cock. I'm literally getting milked from the inside with no hands.

He makes me plant them on the table where my girlfriend always does in the videos. And then he fucks me, making me so so hard and leaking and watch as my cum leaks slowly drooling onto the table, until a small pool of whiteboi jizz has been drizzled out into a puddle underneath me.

He fucks me prone and puts the vibrating pussy up, stroking it down around my cock. It feels fantastic, my asshole and cock massaged at the same time, I cum instantly doing that and feel sensitive and sore quickly, he stops until I get hard again, able to take it without cringing, and then keeps going until I spurt again.

He's milking me.

He pins my arms to my back and shoves his cock up my asshole again, fucking and pulverising my bussy until he let's go and spurts in the hole.

"The only way to submit to me is to cum. I want you to cum whiteboy. I want you to cum until you give up that girl to me."

"I want you to cum away any thoughts of marrying that girl, and let her go, and let her take Daddy's cock until you submit to me and become my tight little hole whore to fill up and cum into, when and wherever the fuck I want."

He spanks me while he pounds me, working my hole up and down and up and down until I'm sweating and panting and leaking, and then he makes me work my hips up and down into him until I leak as much as I can, and then stopping and spanking me home for the next time.

He even ordered me not to cum until the next meeting, making me hard as a fucking rock for an entire week twitching thinking about him.

He was training me.

And then, one day. It happened. I finally rubbed up against and the pounding of my prostate got to be so much that I-

ACCIDENTALLY

Came. I accidentally felt so submissive that I came. I let go. I let go of my relationship, love, any thoughts of a man being with a woman. And I just let go and fell, and let his cock pound me, and finally, finally my anal pounding and prostate massaging got to be too much, and it fucked m prostate so good and made it pounded over and over, that I just worked it trying to get the pleasure from my prostate being massaged to be the only thing to make me cum right from my asshole.

I wanted to cum so so badly and burst and blow my load and fill up any cup he put underneath me, and just fill and fill until there was nothing left but cum and his cock pounding my deeply hidden secret little bussy button over and over and over.

It felt better than fucking a pussy. It felt like getting fucked in the asshole by your worst enemy who's fucking your girlfriend while you earn him money.

It felt incredible.

And I came. I came out a big, hot sticky gooey, pleasure-filled load of juicy, dangling, pathetic white male cum all over, spurting like unsure coughs of an exam taker who'd been tightened up for so so long, and I came out any straight masculinity I had left, and suddenly had an urge to take his cock a lot lot more to get that feeling over and over and over.

"Th- thank you for inviting me over s- sir!" I blurted out.

SPANK

"Good girl."

I moaned, the cum still spurting as I leaked and drained my cock and balls and prostate of anything they had been storing up.

"Ohhhhhhh fuuuuuuuuuck..." I moaned, cumming and feeling waves of pleasure in my cock, my balls, my prostate deep in my asshole, my eyes, my brain. I came and spurted my entire load of white jizz to splatter filthily all over his nice, clean coffee table where he'd fucked my girl, and made her cum from fucking her hole too.

And I finally shivered good shivers.

"M- Mr Johnson s- sir..."

"That felt- oh fuck- oh NO that felt good!"

SPANK

"I know it did cuck. You're moaning like a girl."

I didn't realise until he pointed it out but he was right. I heard them, little moans. My moans.

"Come back and be a girl for me every time you get horny now. Not even horny for prostate fucking. Come back and take my cock, cuck. Come back and take it slapping you."

And I did.

I don't know when I came more from getting my hole fucked than from fucking someone else's, but it happened. The amount of pain from trying with girls and failing. Getting rejected and rebuffed and made to feel horrible, until this? There was no question. No contest. I preferred the straightest cock to the complexity of pussy. Just pounding and pounding and pounding me away. He was a man. I was an asshole and bullied prostate. That's all there was to it.