Chapter 2 – Chapter 2

He straddled my legs, kneading my buns. I could feel his cock flopping around on my thighs. Greco exhaled audibly, "Wow you really do look like Gemma. I don't know if that makes me want your ass more or less."

My brain jumped into overdrive, "Shit! Greco was Gemma's father. Or was he? Gemma wasn't an unpopular name. It could be another Gemma. And I didn't know his last name. There was no proof.

And if the big-wig movie mogul was the same rich semi-celebrity, why should I care?

He continued his monologue, "Well, it doesn't matter, it's really very sexy in its own right." He tugged harder, yanking my shorts off despite never having unbuttoned them.

Without the jeans my thong was on full display. My lover snapped the fabric before tearing them off me, mumbling, "I'm gonna fucking remember breaking in a virgin for a long time. I'll remember your sexy eyes too."

Spreading my buns the big-wig whistled, "That's a gorgeous virgin bung.

Where on Earth did Paulee find you?"

I answered, "It was my first day at the agency and his was my first job."

"Robbi! That was a rhetorical question. You're not supposed to answer – it spoils the illusion."

There was a tray by the bed containing an assortment of gifts from Paulee: lube, condoms, chocolate, weed, and coke."

He smeared about a gallon of lube on my whole butt. Then flopped down on me, wiggling his cock between my hugging buns.

Leaning his flabby naked body over mine, kissing me all over, groaning with immoral hunger: he made me feel more wanted than any girlfriend ever had.

When he bit my shoulder I could feel his now stiff cock knocking at my back door.

He poked awkwardly, not bothering to use his hand to guide it into me. When his head finally found a place to catch he pressed harder.

The stretching was much greater than it had been with Paulee but it was a good stretch.

He asked, "How's your virgin asshole doing?" I kept quiet. "Just answer softly in a girl's voice."

I was only a virgin yesterday and his was clearly thicker. I pretended to strain as I whispered in a falsetto voice, "It hurts." It didn't. "And it's stretching me more than I can bear." I could bear it. "You must have a monster cock." Well, maybe it was a bit thicker.

He jammed into me hard, balls deep in one stroke. He pistoned with no mercy. Was he wanting to hurt me?

His thrusting was frenetic and non-stop. This was a true fuck in every sense of the word.

Greco reached around me grabbing the head of my cock with a few slippery fingers. There was barely room between my stomach and the mattress but he managed.

The rubbing friction felt amazing and after being stimulated for the whole night his touch heightened my need.

His voice was ragged and hoarse, "Take it you spoiled brat."

His thick short cock was gliding against something in my hole that shot ecstatic feelings coursing through me.

Twenty to thirty thrusts later he yelled out with his orgasm. "You are a hot and sexy virgin. I want my big cock to drive you over the edge."

He stopped moving, fully inserted in my ass. His pulsing cock, the rubbing inside my asshole, and the tight grip of his fingers on my cockhead brought me off.

My cum streamed out, coating his fingers, staining the sheets, and causing my ass to milk a final few drops of cream from his cock.

Lying prone on top of me with his full weight, Greco was huffing and panting, and while I'm not sure, Between gasps I think I might've heard him say 'Gemma' or maybe it was something else.

Minutes later when he was getting dressed, I asked him, "There's fifty girls at the agency and only one of me. Why did Paulee get me for you?"

He answered, "Finding a virgin girl is like finding a four leaf clover. Finding a virgin girl who will give it up, is ten times harder. Also, girls fake their orgasms. But a boy with a virgin pussy is not so hard to find. Also, you can't fake yours."

The next day in school I saw Gemma in the Union. She's got her fathers nose.

We were half way through lunch when, smiling smugly, as I claimed my prize, "I got the job and I lasted a week. They never treated me any different than any other worker. I win,…Kitten."

She argued that the business I worked for was sexist precisely because they treated me exactly like any other employee. "They make the girls work topless. That's fundamentally a different experience for a man than for a woman. So it doesn't matter. They're still sexist."

I knew she would try to worm her way out of it, so after some haggling we decided to get our friend Carolyn to look at the ad and arbitrate.

I waved the ad in the air and slapped it down on the table. Together, Gemma and I slid the paper over in front of her to judge.

She read it for a couple minutes then definitively said "It's a sexist contract because Gemma was going to be a kitten – a traditional female role, while you were going to be a butler – a traditional male role."

I protested, "Wait! We're talking about the ad, not the contract."

But Carolyn confounded me, countering, "The contract says 'the offer on this paper' and since the contract is on the paper it counts."

I felt lost, grasping for a way to prove I was right, I objected, "But Gemma came up with those terms, that only proves that Gemma is sexist."

Carolyn didn't care and Gemma was determined to claim her prize.

It was two against one and I had agreed to let Carolyn decide.

On Monday I arrived at Gemma's house dressed in the butler's uniform she provided. The place was massive. The stonework alone must've cost millions just for the raw materials.

Unfortunately, I was going to lose a week's worth of time that I could've spent working for the agency.

"Well," I rationalized, "maybe she'll make me have sex with her."

The door opened: "Hi Mr Gianopolos. Nice to meet you." I wondered if he would recognize me, or might later, as I was going to be there for a week.

He didn't, "I hear you lost a bet. Say, have we met? Are you related to Alexandra Daddario? You've got her eyes."

I still feared the possibility of recognition but so far so good. I'd passed the first hurdle.

Now I just needed to last a week.

Author's note:

If you liked my story please give it a good rating. Add it to your favorites to read later if you want. Follow me and you'll see all my stuff.

I try but don't always succeed in creating a good story. Please add comments so I know what I'm doing well and what to improve on. If you want to talk I'll answer your friendly comments.

I often attempt to create tension in the main character's motives. In turn, this often means that characters in the story have flaws and might not even be nice to each other all the time.

I really appreciate polite comments!