She takes me all the way...
My amazingly hot Filipina girlfriend had taken complete control of me. I was bound to the coffee table, naked, nipples clamped, her wet panties over my face. And now she was going to take it even further.
She stepped towards me, with that huge black dildo buckled into some kind of leather harness, wrapped around her slim hips.
"Better open that mouth and make this wet, bitch boy, because you are losing your cherry tonight!"
I opened my mouth as wide as I could, but she forced it deep, causing me to choke. She just smiled. Then there was a flash and I could see she had taken a photo.
"You look great with cock in your mouth, my pet. I might like to see you take the real thing, what do you think?
I shook my head as much as I could with that huge dildo pinning my head down through my throat. She clearly enjoyed the panic in my eyes. "Yeah. We'll definitely do that. I'll have to think about who is the perfect guy for you. Hmmm, there are so many young guys at your firm....I'll bet we won't have trouble finding one."
She pulled out of my mouth, and held up the black cock, now shiny with saliva and juice from my throat.
"But if they like your mouth, they will probably like your ass too, so I guess it's time to turn you into an anal slut!"
She leaned down towards my ear again, and whispered. "You may not like it at first, but you will come to need it, my pet. Because it is my wish, and you are so desperate to please me so I don't drop you and find a guy who can satisfy me the traditional way..."
Humming to herself, she walked around the table. She grabbed a pillow, and put it on the floor between my spread legs.
Her dildo looked enormous. "Scared, pet?"
I nodded. "You may speak."
"Yes Mistress. I have never been penetrated before."
"So, would you like some preparation before I take your anal virginity?"
"Yes please, Mistress. If you would ..."
She put two fingers into my mouth. "Make them wet then."
I sucked and licked for all I was worth. She pulled them out of my mouth and in the same motion jammed them deep into my asshole. I couldn't help make a sound at the violation.
She frowned. "I'm helping you out here, and you are complaining? I could go straight to the main event if you prefer..."
"No Mistress...I'm sorry. Please continue."
She pulled her fingers out and brought three to my mouth. "Better keep going then."
I could smell ass on the fingers, but I opened my mouth, and licked them again.
She smiled. "Now you are starting to get it."
She pulled the three out and, again, jammed them ruthlessly deep into my already sore asshole. This time I managed to avoid any sound.
"Very good, my pet. And look, your little dicklet is getting hard . See, you might have what it takes to be a great anal slut slave for your hot Asian mistress."
She was right, my cock was suddenly standing straight up again, throbbing. I didn't understand why, I was not ever remotely interested in being penetrated...but she was pushing buttons I guess I didn't know I had.
"Ok, enough. Time to turn you out for real. And, if you are good, I might give you the reward your little cocklet clearly desires."
She put the three fingers back into my mouth. "Clean them."
I did. Once she was satisfied they were clean she put the dildo back in my mouth. "It looks dry, so you had better work on it again."
I had used up so much saliva that I was not able to make it as wet as before. "Oh, is pet a bit dry mouthed? Here, let me help you. Open up..."
She leaned over, licked her lips, with an evil glint in her eye, and then opened her mouth and spit a huge pool of saliva into my mouth, and then jammed the phallus back in.
When she pulled it back out it was shiny again. "Much better. Otherwise you were going to be in trouble."
She wandered back to the other end of the table, and knelt between my spread legs.
She smiled that wicked, partly playful, partly evil smile again. "I LOOOVE virgin ass!"
She scooted forward and put the head of the dildo against my slightly stretched opening.
"Look in my eyes, and no sound!"
She pushed. It hurt like crazy, but she was relentless, leaning in, pushing, until the head popped through the anal ring. "See pet, your ass is open for business now!"
She pushed deeper, and while it still hurt, I could feel my cock rising again. It was crazy, but I was turned on by my mistress' cock in my virgin ass.
She noticed with a smirk. "Anal whore. I knew it. I'm going to have so much fun pimping your ass out. But first, I get my fun. We are going balls deep!"
And she grabbed my thighs and rammed herself against me, pushing her dildo all the way in. I couldn't help it, I hissed a long breath.
She frowned, but didn't say anything. Rather, she starting pumping in and out, raping my hole with the full length of her cock. She pulled all the way back until the head was just inside the ring, and then thrust back in...over and over.
She is in great shape, and the picture of her tight, hot body and abs ramming into me, her boobs shaking, nipples fully erect, was, amazingly, totally hot.
And, gradually, the pain in my ass turned to a strange kind of pleasure, and my cock continued to stand, rock hard and throbbing, even though she wasn't touching it.
My Mistress started to flush as her own arousal climbed. She closed her eyes as she approached another orgasm.
"Yes! I love turning men into my anal pets...it makes me so wet. I'm going to cum again....yes, almost there, and NOW!!!!"
I could see her abs ripple with the force of her orgasm. Her cock stayed deep in my ass, pushing the force of her spasms deep inside me.
After about sixty seconds of recovery she opened her eyes. That nasty glint returned.
"Well, you did ok for your first time. Would you like a reward?"
"Please Mistress, let me cum."
"I might let you cum, but it will be under my rules, and you will obey them completely or I will never touch you again. And you will cum with my cock deep in your ass so you learn that is how it should be."
"Yes, Mistress, your rules."
She put her hand on my cock, which was aching for release. She teased it with her nails, raked my balls, and put her longest nail deep into the pee hole.
"Just wait til I penetrate this little hole, my pet. I have a toy that is perfect for that...but I'll defer to another time."
I had no idea what she was talking about, but it was sexy and scary at the same time.
She pulled the panties from my face, and teased the head of my cock with it. "Are you ready?"
I nodded. She put the panty over the head of my cock, and started to jerk me off with the silky fabric. With her other hand she pulled on my aching balls, stretching them down low.
"I'm going to show you that cumming has a price, but since you love me and you want to cum you will take it and ask for even more..."
She jacked me faster and faster, until I was almost there. She stopped, taking her hands away completely. My hips were trying to find any kind of contact, but all that was on my cock was her panty, teasing.
She laughed. "All guys can be controlled through their cocks. It's amazing that more women don't get it."
She put her hands back on me, and started to jack me off again. "Do you know what a ruined orgasm is, my pet?"
Ruined orgasm? That sounded scary for sure. I shook my head.
"Well, you are about to find out..."
She jacked me faster and faster, bringing me to the edge, and then, just as I felt my balls start to shoot, she removed her hands again!
Simultaneously she somehow released the clamps on my nipples and I felt the most pain ever flood my chest! I had tears running down my cheeks once again.
While reeling from the pain in my nipples, my cum ran out in dribs and drabs, filling the gusset of her panty with goo, but I didn't have the pleasure of real orgasm. In fact, my cock stayed hard and my balls still ached!
She put her hands on my cock head and rubbed, which caused even more discomfort...
My cruel mistress watched the expression on my face with delight. "THAT is a ruined orgasm! It's like a milking, where your cum runs out but you stay horny and unfulfilled, and painfully sensitive. Adding to the fun is the incredible shock of the blood returning to your nipples. Wasn't that fun?"
I didn't answer. "Don't make me repeat myself!"
"Thank you mistress, for allowing me to cum."
She took the panty off the head of my cock and jammed it into my mouth. "Now, clean up all your nasty cum. From now on, any time you orgasm you eat it. You need to learn to love the taste...for when I introduce you to real cock!"
I did as she asked, helpless, ashamed, but still so turned on by my amazing, cruel Asian mistress.
"I think you have an office party with significant others invited coming up shortly, don't you?"
I nodded. "Perfect. I'm sure we can find some fun there, don't you think?"
I could only imagine the fun she would have...at my expense. But what could I do. I was addicted to her.