Loosening Up Gina Ch. 01

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She thought for a while, but in the end she could only think of all that money. "Ok. I will do it." Gina said her answer jumping at the chance she thought lost.

"Good. Please come back tomorrow morning and I will have a deal contract ready for you to sign. You don't need to bring anything because you will be living here from now on." Leibman said.

Gina grabbed her clothes from the floor and dressed them quickly as she left the small warehouse that would soon become her home. She looked back at it and decided she could take the pain that was coming to her ass if it meant all that money.

Leibman was ecstatic. "This will be great, my pet project has finally a star. I got to get things ready."

CHAPTER 2 - First things first

Gina couldn’t almost sleep that night (not that she did most of the time), she thought this was all a bit sudden but if she had the chance to get her hands on a million she wasn't going to waste it for a little pain in the ass.

Next morning she wore the skimpiest outfit she could find, she was not taking any chances of Leibman changing his mind at the last minute. She got a practically see thru top, a micro leather skirt, some high heel pumps and between wearing panties or not she couldn't decide. But in the end she went for an incredibly tiny black thong, she didn't want to be arrested in her way there. That outfit managed to get her even sluttier than her normal working clothes.

Later in the morning she was at the Phallus Entertainment warehouse, she didn't even bring any possession other than her purse because Leibman told her he would provide for her. She took one last breath and pressed the bell button.

Leibman had spend the rest of the last day getting the first props ready, he tried to setup his internet business arrangements for this day but it was impossible in such short notice so it was only good old camera film for now. The morning came and with a bell ring Gina came along too. Today was going to be fun, but things were bound to get better and better. When he opened the door and Gina walked in he saw just how fun they could get, this girl was the slut incarnated.

"Hi. I'm here." Gina said with a million dollar smile.

"Ah, miss Gina, I'm glad you could make it. I have all the arrangements ready, if you would please follow me." Leibman said escorting her towards a desk.

"I've drawn up a contract to seal our arrangement, it's right there on the desk. It discusses all the terms, but as you assess our offer it is only fair that I can assess yours, so if you could please strip naked you can bend over and read the contract as I give you one last inspection before you sign." He said trying to keep a straight face to impress the girl.

"Humm... ok, I guess." Gina agreed thinking it was standard practice. She took off her top and skirt in no time and her panties followed soon.

"Your boots too, if you sign you wont need clothes much more so you can get used to your new uniform. Then go over the contract and bend over to me with your legs spread." Leibman said his final instructions. Gina nodded and untied her boots, reached for the desk and bent over leaving her eyes and hands positioned to look at the written contract and her holes available for Leibman.

She started looking about the first page of the contract, she couldn't read all that well and she noticed it was in complicated lawyer terms, but before she could notice more she felt a sudden push, her pussy filled, and then something between her legs. Leibman had wasted no time and slammed his cock into Gina's generous pussy, he just had to try that marvel. He wanted to sample it dry to make her scream this time but to his surprise it only felt a bit more resistant to penetration than his last attempt. This girl was juicy.

"Yeah! Don't let me stop you from looking at the contract, go right ahead." He said starting to pound her in and out.

It didn't hurt Gina right away but after a few seconds the unexpected intrusion became painful. She didn't want to wimp out now with her opportunity literally in her grasp so she just bit her lip to keep from yelping and tried to relax as she did with her more fiery tricks.

As she tried to read the contract Leibman would slow down and then rammed her two or three times real hard to get her concentration off. He had riddled the contract with all sort of legal loopholes, it was twenty pages long with several different font types and sizes and in the first page a big phrase in bold with an empty line for signature: "Upon fulfillment I will receive in option a million dollars contract as leading actress for a movie."

All was meant to get the fullest legal, and ilegal, control possible over Gina and especially over Gina's body. Every time she changed pages he would pound harder and more randomly, when he saw her look at the signature line he got to the point of gently popping out and rubbing her clit with his cock head. Gina couldn't concentrate, she could only see and think of millions, she tried to read but she didn't want to decide she just wanted to accept. Leibman decided to push her into it.

"I don't have all day, have you decided..." He fucked her gently. "Or not?" One brutal ram.

"Yes." Gina gasped.

"Well, yes you decided or yes you agreed to the terms." Leibman asked with an authoritarian voice.

"I agree." She replied out of breath.

"Good." Leibman said going to the table and fetching a pen and something she couldn't make out.

"Here, a pen. Sign there on the dotted line." Leibman pointed as he moved back behind her again. Gina took the pen and started writing her name. She felt something cold, it seemed metallic twisting around in her now burning pussy, which was only now starting to get a bit more wet.

"Have you signed?" Leibman asked getting ready behind her.

"Yes. It's don..." Gina was answering when: "Aaaaaaaaaaaaahhhhhhhhhhh!" A sudden sharp pain came from her ass.

Leibman wanted a start in style. In fact, this very first meeting was being taped with a few cameras built in the walls. He wanted to start breaking her in right away so he got a small metallic tube, no thicker than a finger and also about the same length, with two bearings in each end a bit larger and a small hole from top to bottom. He was wetting it with her cunt juices and got ready for Gina to say yes aiming the thing right at her ass hole. Then, knowing how tight her ass was he pushed it with all his strength into her backdoor jamming it in half way. Gina was in panic trying to reach back and remove whatever was on her ass but Leibman held her tight and secured her hands away from her behind.

"I though we should start your training right now. You clearly need long and deep progress if you want to fulfill what you have just signed. Now settle down and don't remove that thing from your ass or I will get a bigger one to start you with. The pain should go away in a while if you relax." Leibman said to her trying to contain his laugh.

"Au! It hurts. I can feel a huge ball inside me, take it out." Gina pleaded.

"Now, now, it's just a tiny little sphere so your tight behind doesn't spit the tube out when you clench. I will remove it in a while but now I need it to put some lubrificant inside your asshole so that your training tools don't cause you so much pain. You want the pain to stop don't you?" Leibman said trying to convince Gina.

"Yes." She said reluctantly.

"Good girl. But first lets move to a better place, I want to show you your accommodations where you will spend most of the time while we work on your ass. Now, I'm going to let go of the tube but I want you to hold it in with your hand. Don't let it fall off or even slip out any more so push hard. If you let it go I will have to prep you up again and I will use this one instead." Leibman said holding out a greatly larger version of the plug in her ass. It was three times the length and the two bearings were larger than a golf ball. Gina gulped at the sight of the thing and quickly reached back to her back hole and grabbed hold of the tube.

"Follow me." Leibman said harshly while he dropped the menacing object to the ground with a loud thud.

He took her to a kind of a shed inside the warehouse. It was just four wooden walls that enclosed a room space about 20 by 20 feet. It had no ceiling, just a microphone hanging from a type of crane, the door was an open entrance and cameras pointing straight at a rectangular bed occupied all the four windows, one in each wall. It was a normal bed with four bedposts at each corner and a mattress covered by a single white satin bed sheet.

All around the room were several cabinets and on them all sort of toys of all sizes, shapes, colors and with objectives that Gina didn't even knew about. The weirdest for her were several things on the walls that looked like coat hangers.

"This will be your room. You will spend here most of the time until you fulfill the arrangement you have just agreed. But, first take a seat over there in your new bed so I explain your basic rules. Don't forget to keep this inside you." Leibman said to Gina giving her a little tap in the hand she had holding the small metallic object in her bottom.

Gina walked to the bed a little dazed and took a sit on the edge of the bed facing Leibman, she let go of the object and replace her hold with the bed and started to put her weight into it. The spring mattress gave in a bit but her body pressing down on it applied allot more pressure on the plug than her grasp did. She shrieked and gasped for air as the object penetrated further up her anus. Leibman smiled.

"Now listen carefully. This is were most of your exercises will take place, you are to stay here unless ordered otherwise and if commanded remain on the bed in whatever position is asked of you. This arrangment has of course costs as you can be obviously aware of since all your expenses will be paid by Phallus Entertainment, so to ease it we will film all of your activities without exception during your stay with us. Maybe the sale of such footage can give back some revenue." Leibman said.

"Is this the film you promised?" Gina asked managing to smile despite her uncomfortable state.

"No. You will get nothing for the profits of these images, just your lessons. The film contract will only be offered after you meet the objectives your surely read in the contract you signed." Leibman said, and before she could ask any more he continued.


"You are not permitted to contact anyone during your stay here except those presented to you. A strict daily routine will be given for you to follow. Its contents will be explained during the next days so you can best absorve all the details. Hygiene and food are as promised ensured by us although they too must be fully specified also by us. Now! Shall us start shall we? I have prepared a long day for you filled with lots of new and exciting things." Leibman said.

"Now, first things first. As your little asshole is so tight I'm sure it needs lots of help to be ready for any action performed on a porn movie. So, you should get accointed with the routine of lubricating you behind. This will remove the pain from anal penetration or at least most of it. This is what we will use." Leibman produced a large tube of lubricant from a drawer and a long thin wand.

Gina was confused by the objects but was not able to make her questions.

"Get on you arms and legs on top of the bed! Now!" Leibman shouted angrily. Gina startled a bit before starting to climb slowly onto the bed. Leibman was getting impatient with her resolve so he reached for Gina's lovely round ass and cupped her penetrated back hole with his palm.

"On all fours I said! Hurry! You still have lots of thing to do." Leibman shouted pressuring her while he pushed hard against the object stuck in her hole. When she finally got into position Leibman grabbed the metallic plug with to fingers and gave it a few tugs.

"It should be secure by now. Gina, you can relax a bit now but don't push it out, I'm going to let go of it and I want you to put hands below your face and rest it on them." Leibman said. Gina did as she was told. She felt what he was talking about, when he let go the sphere inside her rectum was stuck, her anus was gripping so tightly against the metallic shaft that it held the object without external force. That sphere was digging into her anal walls that were now throbbing around it and it was starting to hurt her. She relaxed a bit trying not to push out but not clenching either and it helped a bit. She was determined to endure this.

Leibman screwed the tip of the tube of lubricant into the orifice located in the outer bearing of Gina's intruding object. It was the hardest part of the object Leibman had to have manufactured. He had to pay big bucks to convince the sex toy designer to make it ready in only a day, and even then he only did it because Leibman was his top client. But he did a great job and the tube screwed in perfectly, almost airtight. Leibman started to squeeze and lubricant oil rushed into Gina's rectum. She gasped.

"What... what is that?" She asked surprised.

"Its just lube, like I already told you. It is a bit more liquid that most but I want it to go a little deeper." Leibman said but I sure didn't calm her down.

"Deeper, what the hell..." Gina was starting to think this was way too many new things for her.

Leibman just kept squeezing and squeezing until it looked that her rectum should be filled with the slippery fluid. Gina was feeling more full and really weird as some of the liquid tricked down on gravity deeper into her bowels.

Leibman felt satisfied it should be enough so he unscrewed the tube laying it down on the bed beside her. She was so tight that, although her ass was sticking out almost straight up, some of the lube gushed out. But before more could do the same, he then took the wand and inserted it trough the hole in the plug into her anal cavity. The wand was very thin, thinner than a normal pencil so as to get in the small orifice but it was quite long, almost 15 inches and not all that flexible as it was made of metal also.

On his first thrust Leibman buried almost 8 inches into Gina. Then was when the moaning really started going. Gina felt a sudden solid penetration replace the fluid inside her, not only that but it was way deep inside her. Although it didn't hurt it tickled her bowels and she couldn't help moaning at the weird feeling.

"What... what... what...?" Gina kept gasping after the first word.

"This? Oh, I'm just spreading the lubricant a little better inside you. Anyway if you are to do any decent anal performances your ass should go deep as well as wide." And with that he started to slowly push the want in and out.

At first he would just move out an inch or two, but he started to stroke wider and wider to the point of leaving just the tip inside the plug before plunging back in. Then he speeded up the pace. The lube inside her kept going deeper inside her and her she could feel it as it ran along her anal walls. He kept it for a few minutes before he started to tire his arm so he started to plunge deeper moving in a few more inches. That got Gina's attention all right.

"Ahhh. That's... deep... toooooo... deep... deep!" She tried to state her discomfort through her moans.

"What this? Miss Gina, this is not deep. But if you are so eager to know I'll show you what is deep." And with that Leibman pushed the wand as far as he could before he hit the walls deep in her bowels. He managed to stick the thing so deep that only about 3 inches of it was showing out from the hole in the plug.

"Take it out, take it out!" Gina was in panic, but she felt the solid thing so deep inside her that she was too afraid to move fearing it could injure her. Leibman grabbed her hips firmly just in case but he left the wand buried deep inside her.

"Now that is deep, see. Do you want me to take it out?" Leibman proposed. He went to the drawer to fetch another thing that Gina was too busy trying to avoid pain to notice.

"Yes! Get it out! Get it out!" She said not even thinking twice.

"I see. But to do that you must learn the first thing about anal penetration. Remember, yesterday when I told you to push?" Leibman asked taking his time.

"Take it out! Take it out!" Gina kept saying.

"Now, now don't be hasty." He said actually giving a little tuck to the protruding wand.

"Yes! I remember. Please..." Gina shouted.

"Good. When you push your rectum relaxes allowing for things to pass, as you well know when you go to the bathroom. This however can be used not only to push things out but also to push things in, until a certain point at least." Leibman was taking his sweet time relishing on Gina's discomfort.

"Please..." Gina pleaded.

"The trick in anal sex it that you must keep that pushing until your bowels relax enough to hold it involuntarily which for the untrained actress can be for a long time. So what I want you to do is to push like that and try to hold it for as long as you can." Leibman said, saying each word calmly, tantalizing Gina.

Gina just wanted that thing out so she started pushing. Leibman grabbed the tip of the wand with one hand and the outer bearing on the plug with the other.

"You must push a bit more than that." Leibman coaxed her. He finally saw her ass heave a bit so he pulled the wand out a bit but left half inside her. He started to move it a bit but Gina clenched again. When he felt it he pushed the wand way deep inside her again. Gina screamed.

"Don't do that." Leibman said harshly.

Gina managed to relax again but after a while she could not help it and she clenched again. Each time Leibman would push the wand hard again inside her. One time he pushed just the right way and it went in almost all the way, Gina felt a very sharp pain and pushed hard almost immediately and Leibman quickly pulled it out before he hurt her.

They went on and on until finally Gina could more or less hold it. Leibman pumped the wand in and out effortlessly a few times before he was satisfied, he was trying to make her clench again as he was having a great time watching her squirm.

"See, this is the way. Now! Before I take this out I want you to push really really hard, ok?" Leibman said. Gina just wanted it to stop so she pushed even harder, even as Leibman moved the wand around she kept pushing. Leibman felt her anus really loosen up and then her sphincter heaved enough that if he would let go of the plug it would slip inside her ass.

It was time. He withdrew the wand in a rush, and then the plug just as fast. Gina's ass had a tiny gaping hole and a strategically placed hot light lit up her pink lube glistening insides. Then Leibman reached up for his next surprise and held up a vibrator. It was a small one, a bullet shaped very smooth golden vibrator only about 6 inches long and only a bit under an inch diameter.

Before Gina would stop forcing herself open Leibman unceremoniously slid the vibrator into her gaping bud. Gina felt the intrusion. She felt cheated, she was promised release and now an even bigger torture was banging at her back door. She stopped pushing and even tried to clench as soon as her distended anus could, but it was no use. The lubricant made her efforts ineffective. Leibman just kept pushing even after he felt resistance not resting until only the black plastic bottom of the toy was protruding out.

Gina started crying. "No. You said you would take it out. No more." She said convulsing.

"I said I would take that out." He pointed to the objects he had just removed from her bowels and had thrown to the bed near her face. "I didn't say I would not put anything in. Anyway, that was just preparation, now is when when the first of your lessons will really start."

Gina was half convulsing, half gasping, and half moaning. She didn't know exactly what had been introduced into her nether regions but it sure felt huge. Her well-lubed ass didn't cause much pain now except for the extremely uncomfortable stretching. She didn't know what to do with her ass, clenching would hurt her too much and if she relaxed who knew what that bastard might do next to her.