"You want to know my first REAL monster?"

Christine, the human journalist shifted under the blankets. She was nude, her wide hips snug in the sheets.

It was a good sexual marathon with a human woman Tyler had. She had let loose in the bedroom quite well, her throat, her pussy and ass aching to numbness. Lescatian religious suppression surely made them mad for sex.

"Yes..." She moaned, hugging him, large breasts melting in his hands as he cuddled with her on his lap.

"I'll recount. I was fresh nineteen by then."

She opened her mouth, slowly suckling his balls, legs spread on the bed. Smiling, he slowly thrust his cock inside her throat when he was aroused again.

Human women, when properly roused, were insatiable.

**

You see, I was nineteen, getting to work slowly. First I cleaned the rooms, cooking, and eventually given to my first customer.

She was an Ushi-Oni. Do you know of them? Ahh...take it...you do know how to swallow cock, do yo- OW!

Alright I won't tease! Owie! Owie!

Ahh, thanks...Back to my first work as a boy prostitute for monster girls...

On a warm summer night, boys waited on the courtyard of the establishment. It was custom to wait on a row, enticing monster ladies to come and visit.

Skinny farmer boy with shorts, pale as fuck, hair of gold, I was just the treat of a mature monster lady. Older Dark Elf and Yuki-Onna make it a habit to own several young boy slaves for personal attendance, sex notwithstanding.

I was still young then, waiting with the other boys nervously as monster girls entered the brothel and started drinking.

A row of orc girls, fresh from an honest work at the lumber yard, already started celebrating loudly and pulling boys on their laps. Paying the eager Madame Zsa-Zsa some handfuls of silver they started singing and drinking, kissing the reluctant boys.

One of the orc girls had looked to me then, shrugging.

"Too skinny. You got the hots for youngling humies eh, Zsa-Zsa?"

The Jabberwock, ever dressed like a queen, had laughed sweetly, patting my head. "Nah, outcast from his village. Give the boy some time, will ya?" Both laughed, patting my head and giving me a beer.

The music and laughter was rich in the monster brothel, whom Zsa-Zsa had bought from captivity having at least a decent life even before peace had settled. One of the human maids was on the lap of a muscular Orc girl who paid no heed to the boys and slowly kissed her, squeezing her breasts.

It was the adolescent's wettest dream topped with cherry.

That was when she entered the brothel.

A massive Ushi-Oni. Zsa-Zsa had already giggled loudly, nudging her secretaries when she saw the shy monster girl enter.

The arachnid demon monster girl skittered shyly amongst the boys and girls, passing them and apologizing whenever she bumped someone until she passed me by.

Zsa-Zsa was grinning wider, looking at me.

Oh boy.

Furry, fluffy spider legs thick as my waist carried a massive, cute monster girl with big, furry cow ears perked up. Her face was shy, youthful, one eye covered by a Sacred Sutra. Her body was grey-black, large breasts topped on a furry spider body, her groin covered by a strange vambrace of an Ox's skull.

"H-hi..." She looked down, squirming with all her eight legs.

I was mixed between running and begging for my life: Zsa-Zsa would flog runaways, berating them "How good they had it here and now they would run away? That's not good."

Any other takers? I looked around desperately.

Fuck.

Next to me, a centaur woman who had distinct Eastern features of the Mongols, was sharing a fermented milk drink with a strong human male, enthusiastically talking about archery and combat. Her hands wandered over his muscles, pleased with what she found, a strong package downstairs and a strong body.

"Looks like you have what it takes to ride me, anda..." She had slurred drunkenly, hugging him. "I always wanted a good bahatur to give me good strong foals, you ready *hic* for it?"

"I'm all yours, my khatun." Terry was well mannered and educated. I kinda envied the man, quite attuned to his new existence. "Why don't we stroll over to the stables?"

"Hehehehehe..." She giggled. "Get on me, and I'll show you how my thighs can crush steel..."

He slung a leg over her equine body, making her giggle as she trotted to some of the secluded parts of the establishment: centaurs liked having sex in an environment that looked like the stables.

Not my issue. They like what they like eh?

Back to good old young me. Gods, it was three score years ago and I remember it like yesterday...

Why did I have to be matched with a monstrous...monster...lady for my first time? She looked at me hungrily, eyes darting under the Sutra between Zsa-Zsa and me , young human with the big dick, the poor boy prostitute.

"Welcome miss..." Lady Zsa-Zsa curtsied, her tentacled wings grinning by themselves. "Found someone to your liking?" She was politeness incarnate even when the poor big girl nearly tipped over a punch bowl.

"S-SORRY!" The Ushi-Oni squealed, recollecting herself.

"It's alright. You came for a boy?"

"Yes, yes!" The Ushi Oni squeaked, nodding eagerly, her cute ears flicking.

The Jabberwock madame was a master of her work, signaling the maids to bring some refreshments to oil up the trade. What would we do without her skills to blend friendliness with profit and hospitality?

Of course her Red Oni bodyguard was waiting with a friendly smile...and a THREE METER IRON ROD in case anyone tried anything.

"HELLO!" The Ushi Oni shook Zsa-Zsa's hand with a cute clawed hand, making her giggle. "I came...for you know..." She squirmed.

Zsa-Zsa politely calmed her down and handed her a relaxing punch drink. "Please. We cater to many fetishes and sexual preferences, relax and tell me whom you would like to take to bed."

That helped the huge Ushi Oni, who laid a shaking hand to my shoulder.

"He OK?"

Zsa-Zsa laughed sweetly, and told her:

"This is my newest boy, Benny who is a first timer. We got him away from angry farmers about to lynch him when he laid with their daughters." That made the Ushi-Oni squeak.

"Horrible! Why? Humans should make more humans!"

"Yes, now I fed him, groomed him and he is my property to make poor little monster girls like you happy." Seeing the Ushi-Oni smile brightly, she went on. "What's your name?"

"Hoshi." The massive arachnid girl bowed.

"Well Hoshi, how about you pay me sixty silver pieces and he is yours for the night?"

I gulped hard. I was being pimped to a monster! She pushed me to the Ushi-Oni's arms, and I yelped a bit, making Zsa-Zsa giggle.

"Both first timers? You both get some drinks and enjoy each other. Punch is on the house, other beverages extra."

"Okie!" The Ushi-Oni took out a purse from her belt and poured the silver, money for my virginity.

"Be kind to him, alright?"

"YES, YES!" her voice was shrill but cute.

But she was so gentle, I have to admit. Her claws were soft, careful not to hurt me as she held my arm cutely. She leaned on me a little, hugging me as if she'd lose me in the crowd. Zsa-Zsa left our presence, eager to pimp out boys to the monster girls who needed a bit of guidance.

"Hey..." She turned her head to face me. "What's your name?"

"Tyler, miss Hoshi." I smiled, finally gaining a bit of courage and held her arms.

Why not?

She was gentle, not like the cruel looking Dark Elves who loved to spank and flog girls and boys: not that they minded, most even liked it. Just not me. One of the dark elves loved to use boys like a man, penetrating them with a strapped on dildo that looked like a male member.

Just not me neither!! I begged Zsa-Zsa not to employ me like that, and she respected it ever since.

But this one was...soft. She was gentle, kind and shared her drink with me.

"Hey hey, uh..." She stammered over her punch, confused. You see, Ushi-Oni aren't too smart. But they are different, kind, and passionate once the Sutra came off. She pursed her lips, about to press on mine.

"Kissy kissy?"

Oh god.

I aughed. Sorry, but it was too much for me. At least she wasn't angry, but looked hurt when I laughed. I felt like an ass right there and then.

"Sorry." I held her hands. She looked up, eyes twinkling under her sad mien. "So sorry. Didn't know...You are just..."

"Lack confidence? Others say.."

Her cow ears drooped. Aww...

At least that was defused fast. Her joy returned in a flash, a happy smile.

"Okie. Kiss now?"

"Sure, Hoshi."

I nodded, pursing my lips and waiting for hers. That's when I got my first kiss on my job, and a soft pair of lips masticating mine. She was so cute, eyes closed, so I closed mine too.

We hugged to the music, kissing like a young date couple who didn't know shit.

Around us, some monster girls laughed and cooed at the newbie couple making out, us kissing like kids fresh from school. Hoshi held me in her arms, gently squeezing me and setting me on her lap.

"Awww..." An orc girl giggled. "Look at them!"

A dark elf smiled, sipping wine. "SO CUTE!" Some of the Lamia and Harpies clustered, watching us kiss.

"Aww they look like both first timers! So cute!"

Hoshi didn't stop kissing, hugging me until I felt her muscles pressure my spine.

"Kissing is so good!" She squeaked cutely, looking at me with a loving eye that glowed with pink demon love, hearts in her pupils. "Kiss more! Now!"

I chuckled, caressing her ears and pinching them between my fingers.

"Kuu..." She squirmed when I caressed her flicking ears. "Meanie...don't do that..."

"But I love it..." I smiled, kissing her again. "Mmm..."

"Y-you like my ears? A human knight called me an ugly cow...and called my ears dirty cow flops..." She sniffled, eyes teary.

My heart melted. How can I mistreat a demon girl when I was myself beaten to death by farmers? I hugged her deeply, kissing her nose and cheeks until she giggled.

"You are very beautiful, don't let anyone tell you otherwise..." I embraced her with my heart beating fast. She could kill me with those claws, demonic arms and legs.

But it was worth it. It was worth giving happiness to a young girl who wanted a bit of love. I snuggled close to her, hugging her giant arms.

"I wuv you..." The Ushi-Oni cooed kissing me. "Can I take you? Like...now?" She was making puppy eyes, which I could not resist.

Heart beating fast, I took her hand and led her to the building, where already, 24/7 moans and bed creaks sounded. Entering through the door (Which she nearly broke), we ran and skittered laughing like giddy lovers.

The dungeons were out of the question, if not for space, then the sight of a dark elf plump butt sitting on the boys' face would turn me off.

Dark elves LOVED facesitting. Unbuckling their belts and skirts, they would plop down on a human boy or girl, eager mouths suffocated under a mound of plump dark butt. They loved control and domination, and under a Dark Elf, a human was putty, to be used, moulded and enjoyed. No wonder Dark Elves supplied the slave trade until it died down, and even then, maintained informal, consensual slave trading and domineering jobs.

In a world full of sex and war, steel and leather, Dark Elves became the bon vivant mistresses in fur, replenishing their losses during the Fourth Crusade.

And that meant "worship the plump dark elf chocolate butt" for those that submitted. Every visiting dark elf woulda make every human worship their asses and suffocate them until they'd break, give in, and inserted their tongues within. Ever clean and ever groomed, they bit their lips and moaned as mouths worked to worship their asses.

Well, c'est la vie.

We kept running until we found a room, passing harpies fucking in Aviary room, perched on branches as they kept their humans clinging to their wings.

Crazy, but it works.

Finally we found a bedroom and locked the door, the Ushi-Oni giggling all the way. She finally took off her steel bra, and slowly, her ox-skull vambrace, her feral nudity apparent , claws embracing me and slowly stripping my shorts, to discover the large member underneath, which seemed quite happy to see her.

Couldn't help. Her smell was feral, spicy and rank, sweaty from work and running. Her face was cute, happy when we kissed again, she pushing me on the bed with a giggle afterwards.

Pomf.

The bed was soft, and the sudden bulk on me, eight legs hugging my waist, with the musky depths between them loomed on me. Leaning on me, she pushed on me with a savage kiss, slowly humping my painful erection.

I had it coming, a beautiful, caring, strong monster to sit on top of me.

I kissed her huge legs, which she slowly used to caress my chest and legs, in a strange, arachnid massage of strong chitinous legs. Each leg worked in harmony with the other, slowly massaging my chest. Slowly shifting, she smiled at me, as if waiting for something.

Here comes the moment of truth. I shifted my lips, slowly thrusting. My penis felt the most amazing feeling ever, sliding into a warm, soft and tight passage hot from demon energy. Her eyes fluttered as she let out a moan, humping my crotch so harshly I felt like my bones were about to break.

The pressure creaked the bed when the Ushi-Oni, slowly moaning, kept moving up and down, with an incredible pleasure. Moaning helplessly, all I could was to take it, shuddering with every push and pull, helpless, pinned and being taken savagely by a monster girl.

Under an Ushi-Oni, all you do is moan and shudder as she ravages your pelvis, and mine was the first experience to burn in my mind.

She kept raping me for the lack of a better word. I could only cling to her legs, squeaking, with her increasing her pace.

We kept humping like mad until her breathing became ragged, as did mine, our first orgasm building up with our first time.

She started to growl, hugging me with all her legs and arms, and her hips went wild when my member, lodged inside her demon cunt, twitched.

"Oh! Human! Human! HUMAN!" Was all she could scream when I started to scream like a girl, and shuddered, unloading inside her.

It was insane. Her demon energy almost built up my balls the moment it drained, my ass hurting from the sheer pressure in my prostate, pumping my seed inside her until I felt drained.

For minutes, it was an endless ejaculation, the Ushi-Oni's legs clamped around me, letting out a demonic roar that shook the room.

Zsa-Zsa giggled outside.

"Oh god, I hope he is alive."

**

I screamed in pleasure, shuddering for the last time when Ushi-Oni, Hoshi, snuggled to me.

"Wow..." She gasped, hugging me close in her massive black furred arms.

I felt like sleeping, when she kissed me again. I could not stop getting another erection.

And that's when her Sutra came off.

**

I stared into two orbs of demon power, pupils turned to hearts. She giggled, growling.

"Husban?"

Oh boy. I didn't know what would come aftwards.

"HUSBAN!"

She was stark raving mad, roaring like a beast and jumping on top of me until I felt something go *crack*

She had impaled herself on my aching penis again.

Screaming, I flapped like a fish when she kept rutting, now mad, as the room shook.

It was like fucking a giant steam machine that was gone on overdrive, my penis, and cracked ribs filling me with pain, and ultimately, pleasure. The monster demon spider kept raping me of my essence for straight two hours, until in a haze of ejaculations, I felt faint, but could not pass out.

It was being trapped in a cock milker with muscles and the size of a giant horse, my penis exploding in orgasms I couldn't control.

I'd learn that a crowd had gathered outside to listen to the screams, as she broke the bed, and did not stop, roaring and her mouth closing on me for a kiss...

**

I woke up to the sounds of crying.

Hoshi was there.

I was wrapped in bandages, and she was there, crying her eyes out.

When I woke and stirred, she had hugged me, crying and apologizing. Her eyes were teary, Sutra replaced.

"I'm sowweeeeeehhhhh..." She mewled, hugging me.

"Ow..." I mumbled, Zsa-Zsa smoking a pipe next to us.

"Amazing way to have your first time with a monster, eh? Human sex don't count, monster cherry is something you won't forget."

She patted my head.

"You earned a lot for damages and penalties."

Hoshi looked apologetic, and penniless.

Zsa-Zsa, her clothes whirling around her, turned and left.

"You got a bright future in front of you, boy. Enjoy the rest."

**

So that was my first time, fast, and furious. It was an amazing experience, if you know to enjoy it.

We dated later on when I was in my free time. Hoshi gave birth to three Ushi-Oni pups, each as crazy and mischievous as her mother.

One is a general.

So yes, my dear. That was my first amazing time.