Gloria's Billionaire

I spoke to Tony when I got back to the office. I know he wanted to save me. I know now how rich he is, and I know he could make my problems go away. But I need a man who can tame me. Who can handle me. Who I really respect above all men. I feel like Tony is trying to buy me. I am not sure how long I can pretend he has a chance. He gives me these meaningful looks, and talks about my "prospects" but the truth is I don't feel him that way. I don't. When Manuel holds me, or Roger, or Mickey, or Debbie (oooh Debbie) or the strange young man at Debbie's gangbang, I feel a charge. Tony can fuck. He's huge, he's strong, but to me he feels mechanical. Somehow I don't feel that passion for him. It was weird, but we got to work after the fact. He sent me to the North side. Apparently he's got some annoying client. Rupert Price. Young billionaire, really arrogant, defaulting on a long lease when he was supposed to be buying the place. Inherited some money and made more in the stock market. From Texas. Tony was really angry about this one, and insisted I "be careful" with him. Manuel wasn't able to come with me, but I was confident at this point. I could get it done.

I asked for Mr. Price downstairs, and the receptionist looked at me funny. I was used to that. Then he asked if I had met Mr. Price before. I said no. He looked at me even funnier. Then he sent me up with a security badge. I got to Mr. Price's suite, and had a similar experience with his reception person upstairs. I didn't understand. I read a magazine until I was called in. I went into his office, and if I wasn't already amped, I would have collapse. Sitting behind the massive walnut desk, in a tailored suit and handmade Italian loafers, was my mystery friend from the gangbang! A billionaire who could haunt my dreams...

"Mr. Price"

"Call me Rupert. You are sister..."

"Call me Gloria. This is just a uniform"

We both laughed. I don't think he recognized me. Funny how you could fuck someone almost senseless, and not even recognized them with their clothes on.

He was loud, and cocky, but he seemed real somehow. Like he could tell the truth and be done with someone, or be a real good friend.

"I'm here about Tony's .."

"Fuck Tony." He cut me off. I inhaled sharply, surprised he could be that rude. At the same time I was a little turned on. These were balls. Given I had seen his, I knew his bark matched his bite.

"This is the problem with this nigga. We do a deal. It goes south. He offers me a break on rent so I can get something out of it. Then he decides he wants to change things, and instead of coming himself, or calling me, he sends a chick in nun clothes, WHO ISN'T EVEN A NUN! The man. I mean is he serious? What did he tell you?"

I was curious now. Curious and turned on. As we discussed it was more confusing. Tony lost Rupert a lot of money. Owed him big. And had no cash to give. So his offer was to get him free rent in one of his buildings. Apparently after the second year, Tony "forgot" and started sending bills for rent. And there the fun started.

Rupert sat up.

"It's valentines tonight. Do nuns celebrate valentines?"

"I'm not a nun."

"Yeah nun's don't squirt milk, do they..."

I almost fainted. He had a smirk on his face after that comment. He had been toying with me all along. He knew! He remembered me!

"Well they don't usually."

"I may do gangbangs, but I don't forget where I put my dick. Ever. I really wanted to take you aside and pay you some attention, but you left."

"I tried to get your number, but only Mickey had it, and it was hard for me to ask him for it."

"Well, Mickey... sleeps on more pussy than anyone. He just wants to be loved hahaha!"

Rupert was a dick.

"Well you're not going back to Tony tonight, and you're not going anywhere. We're going to get dinner aren't we?"

As I tried to speak he raised his hand.

"Don't do that. You know you want me to fuck you again. Let's get some romance in in the spirit of valentine's day."

He was such a brute. "We aren't fucking, and I will go back to work, but I could do dinner."

He didn't miss a beat. He stood up and motioned me to the door. As we went down in his elevator, I wondered how my life had turned like this. I had two billionaires trying to possess me, and I still wasn't sure where my next meal would come from. I still didn't want to be an object.

We ended up in Rupert's Ferrari, which he tore up Lakeshore drive in. It was specially made to accommodate his six-five frame, and as we drove he told me about his upbringing. Rupert hustled, lied and scraped to get what he had. He was not going to let Tony roll him. He drove to a private airstrip on the Northside. We ended up on a night flight, and had dinner on his private jet as he circled Chicago.

"Rupert, why are you single?"

"I'm not"

"Why aren't you at dinner with your girl?"

"Who said I only have one girl?"

"I mean I know you like orgies but.."

"Who said I like orgies? I like the experience. I like feeling. I like fucking. I like nutrient dense life, without the extras and the fluff. Most people, you go out, have a bunch of dinners, then at some point you start kissing and discover she can't fuck, her jaw is weak, or you don't like her attitude. All that wasted time. I do it the other way around. We're eating dinner because I know you have superior fucking skills and a smashing pussy. I just want to know if you think. How you think. Do you think?"

"Men don't actually want to know if a woman thinks."

"Not true. We just don't do great with bullshit. Especially after we've been fucking for a while. The bullshit is hard to bear. Just give it to me straight."

"I think you're arrogant. I think you're rude. I think you're ripping Tony off. I think you have a fantastic cock, and I think we are both talking too much."

He smiled. A big wide smile.

He reached down and pulled his belt buckle to the side.

"I thought you'd never ask."

As his cock sprang free I was shaken by how odd this was. I just met him, but the act of getting on my knees and wrapping that hammer with my thick lips was natural. It seemed the only thing to do. He was hard and cut, and covered in veins, his thick black cock a force of nature. I sucked hard, and he groaned as my tongue wrapped around his head. I remembered looking at the thickness of its head and wondering what it would feel like inside. The thrill of doing it on a plane turned me on even more, and I was wet and dripping. Knowing that the pilot could look back and see us fucking was even more of a turn on. Rupert pulled off my scarf and my sweater, ripped open my blouse and removed my bra. I shrugged my skirt off. I wore no panties. He pulled out of my mouth and pushed me to the ground. As I lay on my back he entered me, raising my legs around his shoulders. His first stroke split me to the bone, and I gasped. He was so hard and so strong, I felt like this was what sex was supposed to be like.

I understood what I had missed everywhere else. Every inch of my pussy was full, and every stretch and stroke spoke to me. He was fucking my soul, It felt like, possessing me. Taking me. He had a hard rhythm, fast and hard, and it didn't take much for me to come, clenching my pussy and grunting. He kept fucking me, and I came two more times before he turned me on to my knees and entered me doggy style. It felt even harder, and he slapped my ass as I tried to fuck him back. His power overwhelmed me, and I felt my head expand as the rush of blood and hormones overpowered me. This was what fucking was like. I felt him hold my waist and brace me as he sped up his pace. His strokes were urgent and violent now, and my whole body shook in rhythm, as he grabbed my breasts, twisted my nipples and fucked me. I felt the first blast of sperm and came again. He came loudly, and I could only imagine what the cabin crew thought. At the same time this probably wasn't the first time he had done this. He filled me with sperm, and then tapped my ass with his cock as he came out. "We need to do this again, Gloria. We need to do this again."

I was speechless. All the way back to Chicago we talked about this and that, but the real discussion never happened. He took me to his house. By the time we got there, there were clothes in my size, of all sorts. You would think the man ran a store. Apparently he didn't like the nun gear, and had some other ideas. I looked at him sadly. If I wanted someone to dress me up, I would have asked for that. It was annoying that he thought he had to tell me what to wear. Some of those clothes were fly though...

As it turned out I couldn't do it. I left. He had my number, but I didn't expect to call him again. I'm not a doll or a toy. Having said all that, I would miss his dick. Badly.