Loosening Up Gina Ch. 01

Before you read: The following story intentionally does not follow the exact rules of physics and anatomy or sometimes psychology. It is based on fantasies and does not try to be 100% realistic, instead trying to exaggerate and emphasize situations. This can be seen in things like sizes for which I usually give a 'slut factor' of 20% or something like that, or even in the inexistence of diseases or pregnancy from intercourse hence the futility of condoms unless they are used for more ludic purposes. So when you see something that 'just can't happen' try to imagine how that situation would feel like instead of imagining how it could be in reality. Categories will spread across the chapters with emphasis on anal but touching themes of non-consent/reluctant, BDSM, Toys and masturbation and it will be (I hope) almost a novella. Enjoy.

CHAPTER 1 - The cute, the loose and the tight

Gina was a cute homeless 18-year-old girl. She had been in and out of foster homes and orphanages her whole life and the system had finally forgotten about her existence. She didn't care for family life and had never wanted to depend on anyone so she was happy enough with her last flight.

However, now she had to face the hard facts of life. She had been on the streets for several months now and begging for quarters just didn't cut it for Gina. Her path had been cut out for her... with the perkiest B cup tits you'll ever see, a long, a bit uncared for, but still beautiful blonde hair, full lips and two big haze eyes, a tight milky white cute ass that just went round and round, there was some pretty easy ways for her to make money.

Two more weeks of empty stomach was all it took for her 5 foot 5 body's talents to be out for the bidding. Although she hadn't had any experience with sex other than masturbation and the occasional 'educational' movie in TV, she was a quick learn as some of the other girls on the street showed her the tricks of the trade. Her first john still got the scare of his life as she didn't know she would bleed in her maiden coitus and didn't warn him.

It was a month now, she was working the streets and she was at her usual place. She was talking to Tammy, one of the working girls that had helped her get on her feet (more accurately, get on her back). Tammy had painted red hair and was half a foot taller than Gina. She had huge breasts she said to Gina were implants she got as she was getting too fat and was starting to loose clients. Gina saw her like the big sister she never had although they had met only two weeks ago.

"How is it going Gina? Are you too sore? Most girls can't walk straight for a week when they start." Tammy asked concerned of her new friend.

"Well, not really. After the first one, that was kind of freaky, I have actually been enjoying myself." Gina replied.

"Are you sure? How many tricks this week, girl?" Tammy inquired.

"I don't know... about thirty I guess." Gina said.

"Damn girl. You sure have a big demand. You are handling four guys a night? Aren't you sore, I mean how many big guys did you got?" Gina's friend asked getting surprised.

"I'm fine, most guys only want to cum in my mouth anyway. Most of them are small, the others were just normal I guess, at least I did two of them last night and only they hurt a bit." Gina reassured her friend.

"Normal you say? What do you mean, show me how big they were?" Tammy was curious.

"About this big!" Gina showed her the size with a finger from each hand.

"Fuck girl! You're kidding me? You sure?" Tammy's eyes were bogging out.

"Why would I kid? What's wrong? Is this that small?" She asked from her young innocence.

"Girl, that is almost ten inches. I've been doing this for 5 years now and when I get one of those I cant do anything for two days. Are you ok girl?" Tammy asked a bit concerned this young girl was not hurting herself from her inexperience.

"Nah, I even came as the last guy started fucking harder from behind me and his balls kept hitting the flesh higher in my pussy." She said smiling.

"Dear god girl!" Tammy was amazed at this girl she thought was still an apprentice in the business." The way you can take men, you should be doing porn, you always have to fuck big ones like that but at least is a bit cleaner and it can pay top dollar if you have the right body and are willing to do some of the sick stuff they do." Tammy added.

"It pays more? Maybe I should try it. How can I do a porn movie?" Now it was Gina's turn to be curious.

"Calm down girl, it's not as easy as it sounds. First you got to have the right stuff, your tits could be bigger but you're a cutie so you might pass, then you have to get into an audition. You will probably have to fuck a few guys to show them you can do it. The casters will probably want to get a sample of you too. In fact, you will probably have to fuck allot of guys for free before you get a chance in a movie. Some girls I know have been fucking the whole crew of a porn house for free for years now in the hope they get a part. At least in a part they could actually allow to do." Tammy explained.

Gina was looking down sad like she wouldn't have a chance. Tammy looked at her and decided to help.

"There is one producer I heard of that might get you in faster though. He is a bastard and will most likely want to fuck your brains out for a while before he gets you in, but if you please him the right way you have a good chance. I hear they do a bit rougher stuff but from what you tell me I think you might handle it." Tammy said.

"Great. Can I go speak to him soon?" Gina asked with a bright in her eyes.

"Well, here is a card they distribute by the streets to look for talent, it has their address." Tammy said handing Gina the card.

The next day, Gina went up to the address on the card, she saw a very small nametag next to a bell button. It was written 'Phallus entertainment'. It was a kind of warehouse, which made Gina a bit unease, but she pressed the button.

"Who is it?" A voice came out from an intercom.

"Hi! I'm Gina, I came to get an audition." Gina replied.

"I hope you do know what we do here Miss." The voice inquired.

"Yes. I want to do... well... porn. Can I get in please?" Gina pleaded.

"Ok." The voice said and with a buzz the lock on the door opened.

Gina walked into the building that was indeed a small warehouse. It was filled with props for the movies the company produced. There were costumes, lingerie, dildos and other objects Gina had no idea what they were scattered around the place.

"Ah. Miss Gina please come in, I'm Leibman, lets move to over there so we can speak." The man said.

Leibman was the owner of Phallus entertainment, he used to be a porn actor himself but after a while he decided to start a company of his own so he could have a bit of fun. He had already gotten a bit overweight and with a beard he wore nowadays he looked just like the stereotype of a pervert old man. In fact phallus entertainment specialized in more alternative porn, the films were more towards a kind of soft fetish. Lots of dildos, erotic role-playing costumes and even a bit of bdsm. The actors were mainly female as the scenes required mostly rough lesbian play, anyway actors with big enough cocks were very hard to find so big dildos were the more common working tool. Willing girls like Gina were on the other hand always in high demand as others didn't last long in the hard receiving end of Leibman's scenes and quit from time to time.

Gina had dressed to kill so she could get the audition. She bought a white silky blouse that closed with only a couple of buttons in the front, she thought about wearing a push up bra but she thought her big nipples could impress more when they poked out from under the shirt. She wore a pink mini skirt that hugged her ass tightly and showed off all of her thighs and if she walk the right way even a bit of her tiny white thong panties. Her legs wore her fishnet stockings she usually used on the streets and were shaped up by a pair of pink glossy stilettos.

Her long straight natural blonde hair did the rest. This cutie was nothing to pass up even for Leibman.

"What do I have to do?" Gina asked standing up in a more cleared up part of the warehouse.

Leibman decided not to go easy on this girl even if she looked so innocent. She would have to put up with allot of shit if she wanted to work for him so he didn't even tried to make her comfortable first.

"Ok. Let's see what you got. Take off your shirt!" Leibman demanded.

Gina was half pleased she was getting a chance and half afraid of this sudden order but it was nothing she hadn't get used to in the past month. She sighed and unbuttoned the silky shirt, then when she was squirming to undress it she bended up her chest showing off her tits. They were small although very firm but her nipples were quite a sight. They were as big as fingertips and stood straight out from two medium light pink aureoles. Gina looked great with them, even when she was not the least bit aroused they made her look like she was in heat.

"Hmmm, I see..." Leibman though those B cup tits would never make it but he was not letting this perky little tease go before he had his fun.

"Now the rest, lets see what you got under there." He pointed at her skirt.

Gina pulled her skirt down slowly as the elastic fabric hugged her legs tight and pulled on her stockings pulling them down. When she was off her tiny skirt, she was starting to peal out the stockings too but Leibman stopped her.

"No. Leave those on, just get your panties out of the way. Oh, and bend over to me and stay like that when they are off." Leibman commanded.

Gina did as she was told, after she propped her stockings back up straight she turned her back to Leibman, grabbed the sides of her thong and bend over as she uncovered her sex. Her pussy came into view, and Liebman saw she was cute everywhere, she was a true blonde but there was little proof, her pussy was almost bare and a small patch on top and a few furs along her pussy lips were all there was, but they were so light and thin they didn't even curl. Her ass was on full moon, she had great curves and a nice round ass that made her waist look tiny. It was so tight Leibman couldn't even see her asshole with her bent over, but that had to change.

"Hmmm... Spread your legs as far as you can and grab your ankles so I can have a closer look." Leibman said approaching Gina.

She followed Leibman's commands again and was grabbing her ankles as she felt a hand. Leibman came up behind her and cupped her pussy with his whole hand and started rubbing it back and forth feeling around.

"Do you shave?" Leibman asked.

"Shave? I don't have a beard." Gina was confused.

Leibman laughed, he couldn't believe the feel of this lovely bush, he was looking for hair bumps but could only feel Gina's milky skin and her pussy getting a little wet. This girl was just as naive as she looked.

"Ok. Lets see how you handle action. You did have sex recently?" Leibman asked.

"Yes... I'm a prostitute... I have sex every day so I can make money." Gina replied a bit startled by this prodding hand.

"A hooker... well then lets see if you know your job." Leibman reached in his pants and took out his now fully erect 9 inch cock. "Suck my cock," he ordered making her spin around to face him.

Gina was used to this, johns really liked for her to suck on their dicks, they kept telling her she had a great face for fucking. In fact her cutest blonde face with full fleshy lips were just made for a great suction. Her quick learning tongue did the rest. Most of them came in her mouth and made her swallow although she didn't like it she thought it was normal and so did it without much fuss. Leibman was getting blown for only a minute and he had to make her stop a bit or he would come right then and there. This girl knew the job all right.

"Does your throat work too?" Leibman asked after a few breaths.

"Oh no, I can't do that. Sometimes guys try and I choke so much I've got to stop." Gina replied.

Leibman was disappointed he would not get deeper into her lovely face but she was not going to make it anyway so he just moved on to get the rest.

"Hmmm... no deepthroating ... I see. Now for your pussy, you can handle my cock?" Leibman asked.

"Yeah, sure it looks normal." Gina replied. Leibman was a bit intrigued by this 'normal' but hell it was time for a nice hard fucking.

"Get on your hand and feet and get that face down and your ass up!" He shouted a bit harshly. Gina was sensing she would not get into porn and make all that money so she didn't even flinched and put out exactly like Leibman asked.

He put is huge cock right up to her pussy. He usually rammed all the audition girls in one go, no lube and if their pussys weren't wet too bad for them, he wanted to make them scream out so if they ran off he always knew they would not have what it took for the rough scenes. The ones who stayed had always lasted for a longer time. But this girl would not stay anyway so when he got his aim just right he lunged forward as hard as he could. Lucky for him her pussy was all wet or he would have skinned his dick off. He slammed loudly into her back and was expecting to hit bottom hard but instead he just felt her pussy grabbing around his cock.

Gina felt the familiar touch of a penis at her pussy and was waiting for its entry when she felt full all of the sudden and then a large body slapping against her back. She let out a loud moan and then felt her pussy clench shut around the cock inside her.

Leibman couldn't believe this cunt, not only did he not feel the resistance of her cervix being pushed up along the way but this girl didn't even scream, well, not loudly at least. In fact her pussy felt like it had a mini orgasm. He never met a young girl that could handle his full length this fast. Not that he was that thin either, his cock was more than five inches around. This was nothing to waste so he started ramming her as hard as he could.

He went to the point where he would pull out completely and practically jump into her welcoming pussy. They were both panting hard and he was ready to come and just couldn't hold it anymore so in a last effort he pulled out and unloaded all over her back, then as soon as he could he went up to her face and shoved his cock into her mouth where Gina sucked his cock clean and her expert tongue got him hard again.

Gina was moaning the whole time. She would feel full and empty again and again and after a while she started getting hotter and came a few times. She was getting into it when she felt something splash on her back and then a smelly cock trying to get into her mouth. She knew she had to please him so she sucked on it trying to forget the taste of her pussy and of the cum that was still coming out of this cock into her mouth. Then, making a face, she swallowed and looked up to Leibman for approval.

Gina was a natural. Maybe there was hope for this girl, but now Leibman couldn't wait to get a piece of her ass so he went round to Gina's back. She thought he was going to fuck her again so she lowered her face again and sticked out her ass waiting for the next penetration. But then she felt the pressure at the wrong place. Leibman was pressing his cock against her ass. Gina jumped up suddenly.

"Please don't... not there. I can't do it. Its too small and it hurts too much. A few guys have tried and they couldn't even get in." Gina pleaded.

"What! You can't do anal sex. That cannot be. How do you want to be a porn actress and not do anal? There isn't a single scene these days that doesn't have at least a bit of anal sex. Crouch back down and I'll show you." Leibman was angry and couldn't believe that such a loose cunt could not even get a little bit of cock in her ass. Gina was seeing her chance fade away so she got back down again and tried to bear it. Leibman put his cock against her ass again and started pushing in real hard, but she was right, her asshole was damn tight and he couldn't get it in.

"Please. It even hurts when I got to go to the bathroom. Please." Gina was starting to cry.

"Nonsense." Leibman critiqued.

He scooped a gob of cum that was still clinging to her back and smeared it on her ass and started to push again. He even slapped her ass cheeks hard to get her loosened up. In one last attempt he lunged forward real hard but his cock bent painfully with its head right against her sphincter. He only got a pain in his dick and a scream out of Gina's mouth that jumped up again after his last plunge.

"I'm too tight in there. I can't... I can't do it." Gina was crying. Leibman couldn't believe it, this girls ass was like a brick wall. She was so cute and her pussy was so damn hot that it was a shame her ass couldn't cut it. But, maybe if... Leibman got an idea. Yes she would be just perfect for this. He had a little pet project on the works for a time now and was looking for someone willing to do it but it was too much for most girls. But this one, she was alone, she was cute, she was naive enough and her tight ass would be a great twist to it.

"That's it! Of course." Leibman thought. She will do nicely, but she has to do at least something... a start.

"I'm afraid, miss Gina, that you cannot get into this business with that blocked asshole." Leibman said now with his objective clear in his mind.

"But I'm going to give you a chance to get in. But you must be able to do at least one thing." He added.

"What do I have to do?" She asked still sobbing.

"You must take at least one finger." Leibman said.

"In my ass? But it hurts so much." Gina pleaded.

"Just one finger, and I will go easy. If you relax it will go in, you'll see." He replied.

"Ok." Gina assented with great unease after a long silent pause. She bent over again, crouching on the floor. Leibman stuffed his index finger in her pussy to get it wet and then started pushing into her asshole.

"Now. Push on your ass like when you take a dump. You got to relax your ass." Leibman commanded. Gina did it and felt her ass heave a bit. Leibman felt her ass loosen slightly and pushed harder but his finger still wasn't getting in. This girl wasn't kidding, she was tight as hell.

"More. Push harder." He shouted slapping her ass loudly. She pushed her bowels hard. She closed her eyes and forced her ass open as hard as she could and when she felt something move she thought a fart had escaped and clenched again. But now she felt a huge thing stuck in her ass and it hurt her.

"You said you would put only your finger, your dick hurts." Gina pleaded in pain.

"It is. Only my fingertip." Leibman said amazed. When she gave her second push his finger went a bit in, only to his second knuckle when she clenched again. Then he felt what she was talking about. The force on his finger was tremendous. Leibman was starting to feel his finger a bit mashed up in this anal vice. "And this girl thought I had my nine inch cock in there? Damn, I got to get this one." He thought, making his resolve final. The pressure was so great that his finger jetted out when he stopped pushing in. Gina got up again and reaching back started rubbing her poor ass.

"Well. You can at least do one finger. But that just isn't enough..." Leibman was saying.

"Please. I really want to. I need the money." Gina was sobbing from the itch in her ass and her disappointment.

"You didn't let me finish. However, since you have other good attributes I am willing to give you a chance if you are willing. The deal is that you will work for free for as long as it takes, and in return I will help you get your asshole ready for use in porn films. I will also pay for food, bed and whatever you need, however you must live here at all times and be willing to do what phallic entertainment asks of you. When you finish you can get a million dollar contract if you agree to make a porn movie or just leave if you're not interested earning of course nothing. That is the deal I can offer you." Leibman made his move, now it was Gina's turn.