Lindsay Lohan Ch. 03

Dina Lohan, the 50-year-old mother of four, stood holding her skirt up and felt like a teenager showing her panties to boy. It was humiliating but oddly erotic. As she watched Toby pump his cock Dina couldn't help but feel her pussy moisten. She noticed that Toby's cock had stiffen slightly and she couldn't take her eyes off that beautiful fat penis with its big purple head.

"Take your panties off." Ordered Toby.

Dina refused to acknowledge the request and continued to stand with her skirt held aloft.

"Take your panties off." Repeated Toby.

"I can't do that honey." Said Dina "It's not right, I'm old enough to be your mother."

"I think I hear Lindsay in the bathroom." Said Toby "She'll be out here any minute. If you want me hard you better take your panties off right fucking now."

Dina knew it was wrong but she had no choice. She dropped her skirt and then reached her hands up under it. She grasped the waistband of her panties and pulled them down past her thighs, past her knees and down to her ankles. She stood there in front of Toby with her panties around her ankles.

"Let me smell them." Said Toby now enjoying the power he had over Dina.

Dina pulled her feet from the panties and bent down to pick them up. She then threw them across the room so that they landed on top of the masturbating Toby. He immediately picked them up, moved them to his mouth and nose and breathed deep. Toby felt himself stiffen significantly as he breathed in the smell of Dina Lohan's pussy.

"Lift your skirt up again." Said Toby now using Dina's panties to masturbate with.

Dina complied with this request without objection. She reached down and once again pulled up her skirt this time revealing her pussy. Toby found himself staring at Dina while masturbating with her panties and his cock grew harder in his hand.

Dina watched as Toby grew hard and continued his relentless rubbing. His cock now looked near full size and Dina felt her pussy beginning to grow wet. Despite the humiliating position she was in Dina found watching Toby's lewd performance very erotic.

Lindsay meanwhile was in the bathroom about ready to go back out. She had decided to call time on this whole ridiculous situation. If her mother wanted a sex tape so bad then the 5 minutes of blow job footage would have to do. Lindsay was not prepared to do anything more and now fully planned to leave the bathroom and give a full blown rant to both her mother and Toby. Then she would kick them both out and call Sadie to come spend the night with her. "Fuck this shit." Lindsay said right before opening the bathroom door.

She walked into the living room and was shocked to a standstill when her eyes fell upon her mother and Toby. Her mother stood in the middle of the room with her skirt lifted and pussy on display while Toby enthusiastically masturbating with what looked like her mother's underwear.

"Holy fuck." Declared Lindsay shocking both Dina and Toby.

"Lindsay." Said Dina dropping her skirt "I...I...I."

"What the fuck are you doing?" asked Lindsay.

"We are....I mean.....getting him hard." Was all Dina could offer as explanation.

Toby just sat there with a smug grin on his face. He removed the panties from his cock and proudly showed off his now rock hard boner. "And it worked too." He said showing the girls.

"Ok." Said Dina snapping back into director mode. "I'll just adjust the camera quickly and Lindsay you can hop on. 10 minutes and this will all be over."

"I can just hop on?" asked Lindsay sarcastically "Hop on??? Have you seen the fucking size of his cock. I can't fit that into me. Not without hurting myself internally at least."

"Of course you can." Said Dina "Don't worry honey. Your biologically designed to be able to handle it."

"I'll tell you what Dina," argued Lindsay "Why don't you hop on? Why don't you prove this biological design theory by fucking him first. You do it and then I'll do it."

"Honey I can't have sex with Toby." Said Dina "I am old enough to be his mother. I have 4 kids including you. It wouldn't be right."

"It's not real sex though is it Dina?" said Lindsay still using a sarcastic tone "It's just acting. Go on Dina you prove to me that its possible and then I'll do 10 minutes with the camera rolling."

"I don't like you calling me Dina young lady." scolded her mother.

"I don't care either way." Butted in Toby "But somebody better start riding me because this boner is starting to hurt."

Dina looked across at her daughter but found only a defiant look on her face. Dina had seen this look many times and knew Lindsay would dig her feet in until she got her way. She sighed a deep sigh and accepted that she was going to have to fuck Toby at least a little bit to get this video back on tract.

"Fine." Said Dina walking over toward Toby "If that's what it takes."

When she reached Toby she instructed him to sit back down in the chair then she reached over and quickly undid the laces on both of his shoes. She removed the shoes and socks and then pulled his pants and underwear off from his legs. Next Dina reached up and grasped hold of the bottom of his T-Shirt and pulled it off over his head.

Dina looked down at the now naked 19-year-old. She noted that his entire body was toned and almost perfect. He even had the beginnings of a six-pack on his flat stomach. Dina had known Toby since he was just a kid but she had no idea he grown into such a hottie. No wonder her daughter Ali was so fond of him.

Lindsay could not believe her eyes as she watched her mother undressing Toby. Lindsay actually felt a state of shock as she watched her mother bend down to undo the straps on her shoes and remove them. Then barefooted she watched her mother put one leg either side of Toby and straddle him.

Dina's breath became more rushed once she was seated on top of Toby. In truth it had been several year's since Dina had had any kind of sex. And Dina didn't think she had ever experienced a penis this side. Certainly Toby was about to be the youngest lover she had ever had.

Dina reached behind herself and for the first time took a hold of Toby's enlarged penis. It felt stiff as steel and was very warm from all the friction of the masturbation. She lifted her hips and raised her pussy high above the penis.

Using her hand she guided Toby's penis to the opening of her vagina. Then she lowered herself just enough so that the purple head slipped inside of her. She stayed like that for a few precious moments then dropped down so that her vagina completely engulfed Toby's penis.

Lindsay watched as her mother took all of Toby inside her. When she heard Dina release a cry of both pain and stimulation Lindsay thought she might pass out. For a moment both her mother and Toby just sat still not moving then Dina slowly began to rise on the cock and then slowly drop down again. Slowly but surely her mother was riding that monster cock.

Dina gasped as she felt the penis sliding in and out of her. It was so large that Dina felt a mixture of both pain and bliss. The penis seemed to fill every part of her vagina. And even though Dina had given birth to four kids she felt her vagina stretched almost to breaking point.

Toby knew not to try thrusting into Dina. He knew that it was best just to allow the older woman to get use to the size of him. He watched intently as the 50-year-old mother of his friend slowly began to get a grip and started moving a little faster.

Lindsay was truly dumbstruck watching her mother now fucking Toby. She had gotten past the uncomfortable stage and looked like she was enjoying it. Lindsay watched in amazement as her mother fucked her hips harder and faster onto Toby's giant cock.

Dina could now feel her vagina getting really wet and the penis inside it felt better with each thrust she made. She had started this to prove to Lindsay that it could be done but now she continued because it felt so good. Dina began to moan with the sensation of it and completely forgot that her daughter was even watching this.

"Fuck you feel amazing." Gasped Toby as Dina continued to fuck him. This was fantastic and Toby knew it was more than he could possibly have wished for. So far he had been content to just sit there and allow Dina to fuck him but now he decided he wanted to fuck her.

He grasped hold of Dina around the waist and put his feet on the floor. He stood up lifting Dina into the air and for a few seconds they fucked standing. Dina with her legs and arms wrapped around him. For the first time Toby began to use his hips to fuck into Dina. He smiled as he heard her begin to moan.

Toby though could not keep fucking while standing up and dropped to his knees. He gently laid Dina down on her back and found himself now on top of her missionary position. He looked into Dina's eyes and found only desire there. He felt Dina spread her legs wide and knew it was time to fuck her as hard as he could.

Lindsay's legs felt like jelly as she watched Toby and her mother fuck on the floor. When she had dared her mother into it she never expected it to lead to this. They were really fucking right in front of her. Lindsay felt guilty about watching and knew it was wrong but she also knew that deep inside her own legs her pussy had grown wet watching this lewd display.

Dina lay on the floor with her legs spread watching up at the young naked man now fucking her senseless. Toby was fucking her deep and hard sending wave upon wave of pleasure through her body. She through her head back and her moans increased with each thrust Toby made.

"Fuck me harder." Begged Dina as she felt Toby's cock slamming into her and his balls slapping her ass. "Fuck me as hard as you."

Lindsay had never watched anyone have real sex much less her own mother. It was like watching a car crash she just couldn't take her eyes off of it. Inside her bathing suit her pussy was wet and craved attention. For a moment Lindsay considered pleasuring herself while watching but she knew that would be so wrong. But her pussy demanded attention and there was only one thing Lindsay could do.

"Ok." Shouted Lindsay above the groans and cries of her mother "That's enough now. You have proved your point."

Both Dina and Toby ignored Lindsay and continued fucking on the floor. Dina had now closed her eyes and could an orgasm building up and searching for release.

"Stop now." Shouted Lindsay in her most sulky voice. "If you make him cum Dina we'll never get this video made."

The threat of not making the video seemed to work as Dina suddenly began to plead for Toby to stop. She used her arms to push him up off of her and used her legs to push herself away across the floor.

"Fuck." Shouted Toby as he sat on the floor with his wet prick twitching and bobbing in the air. "You can't fucking stop a guy like that."

Dina now sat on the floor her legs sprawled out in front of her with her skirt pulled up high enough to reveal her soaking wet pussy which was red and aching for the cock it had had inside it only a few moments ago.

Lindsay looked over at her mother and felt a little shame mixed with a sexual longing. She wanted what her mother was getting and she wanted it now. "Are you ready with the camera?" Lindsay asked.

Dina managed to stand up and pulled down her skirt to cover her modesty. She walked across the room and got behind the video camera. She adjusted the view so that she had a decent focus on Toby.

"Ok." Said Dina trying her best to be the responsible director again and ignoring the ache in her pussy which craved more cock. "Lindsay honey why don't you take off your bathing suit." Suggested Dina.

Lindsay felt a little odd at the notion of getting naked with her mother in the room but then it had been an odd time all around. Lindsay reached up and pulled the bathing suit from her shoulders down to her waist. She noticed that Toby was watching and almost leering at her with sexual intent. His raging hard boner stood out in front of him and shamelessly he had started to masturbate.

Lindsay pulled the bathing suit down past her hips and let it fall to the floor. She stepped out of it and stood naked as the day she was born in front of Toby and her mother. Dina tried not to look but couldn't help and felt guilty when she saw Lindsay's newly shaven bald pussy.

"How do you want to do this?" asked Dina from behind the camera.

"Can we just stop talking and start fucking?" said Toby in a loud voice. "How hard can it be? She'll spread her legs and I'll fuck the shit out of her."

"Watch yourself young man." Snapped Dina "That's my daughter you're talking about and you will show some respect or this will be over and you will get nothing."

Toby seemed visibly surprised to be scolded by Dina and stopped his masturbating. He knew he was on the cusp of fucking Lindsay Lohan and he didn't want to spoil it now.

"I want to be on top." Said Lindsay "He's so fucking big I want to be able to have some control."

Smiling happily again Toby immediately laid flat on the floor with his prick jutting up above him. He stayed there waiting for Lindsay to make the next move.

Lindsay looked over at the size of his cock and again had doubts as to whether she would be able to handle such a monster. She knew that she was already wet and sexually aroused from watching her mother fuck Toby. She reached a hand in-between her legs and was pleased by the wetness she found.

Barefooted Lindsay took a few steps towards Toby and then stood over him. She dropped down to sit on his legs one of her own legs either side of him. She decided the best way to handle this was to lubricate his cock up a little with some spit.

Lindsay bent down and took Toby's cock in her mouth. She had intended to give him a quick wet blow job using as much salvia as she could muster but as she took the cock deep into her mouth she was suddenly stopped by the strange taste.

It took only a few seconds for Lindsay to realise that what she was now tasting was her mother's pussy juice. Lindsay immediately pulled her head up and let Toby's cock fall from her mouth. She looked up at Toby and he had a huge smug grin on his face.

"How does she taste?" he asked.

"You're a pig." Stated Lindsay unable to turn and look at her mother.

"Maybe." Said Toby "But your about to fuck this pig."

Lindsay pretended as if she didn't hear Toby's taunt. Instead she simply raised herself up high above his cock and positioned her pussy just above its head. Just as her mother had done a few minutes earlier Lindsay slowly began to ease herself down.

She first felt the head of his cock stretch out her pussy. There was a moment when Lindsay considered stopping but with a deep breath she composed herself and inched the cock deeper into her pussy.

It was a painful process but somehow Lindsay managed to slowly get most of Toby's cock inside of her. She wasn't near the bottom but she had definitely passed half way and that was an achievement in itself. Lindsay sat for a moment unsure how to proceed. All she could feel now was the cock inside her, everything else seemed to fade away.

Toby lay on his back and looked up at the beautiful Hollywood starlet he was now officially fucking. He was inside Lindsay Lohan and she felt so wonderfully tight. He looked over towards the camera and saw Dina Lohan staring at them. He had fucked the mother and now he was fucking the daughter. Toby felt his cock swell even further and from above him Lindsay let out a little whimper.

Without looking at her mother Lindsay said "Turn the camera on now." Dina did as her daughter instructed and turned on the camera. As it began to record Lindsay began to have sex with Toby.

Lindsay put her hands on Toby's chest and slowly raised herself up an inch. Then slowly she eased herself back down. She repeated this process three times before she felt her pussy was wet enough to allow just a little more movement.

Aware that the camera was on her Lindsay tried her best to make it look like she was enjoying the sex with Toby. She began to moan and after a few painful minutes she finally started to actually enjoy the sensation of fucking such a large cock.

Lindsay was now able to move more freely along the shaft of his cock. She used her hips to lift up her pussy until it almost released it completely and then she dropped it back down as deep as she could stand. At first Lindsay's moans had been for the camera but now she could not control them as she felt waves of ecstasy beginning to hit her.

Toby was enjoying the sensation of fucking Lindsay Lohan but he longed for a little bit more. He had been balls deep inside Dina and had fucked her hard until Lindsay had stopped them. It felt incredible as Lindsay slowly eased up and down his cock but she was only getting about half of him inside. Frustration began to form inside Toby.

Lindsay was now panting and moaning quite loudly. The slow steady pace of the sex was working and Lindsay could feel her pussy getting wetter and looser with each and every hip thrust. She reached up a hand and grabbed her own breast. She hard it and then twisted a nipple producing a small cry of pleasure.

Dina watched as Lindsay carefully rode Toby. Dina was unable to remove her eyes from the sight of Toby's giant penis fucking into Lindsay's bald, wet and aroused vagina. Dina felt very guilty but she also felt incredibly turned on. Her own vagina ached to feel Toby inside her again.

Toby decided he had given Lindsay enough time to adapt to his size. He reached up grabbed Lindsay by the waist. He lifted her up off his cock and almost threw her onto the ground beside him. Lindsay landed on the floor and sat there with her legs sprawled out before her and a surprised look on her face. Now that he was gone Lindsay's pussy ached for his return.

"I want to fuck you missionary." Demanded Toby.

"Ok." Said Lindsay beginning to spread her legs and feeling a little submissive.

"But first I want you to suck it a little bit get it nice and wet." Said Toby.

Lindsay got up onto her knees and bent over intended to lower her mouth onto Toby's cock but she was shocked when he stopped her. He pushed Lindsay back down and she hit the floor landing on her bottom.

"Not you." Said Toby "I was talking to your mother."

Dina immediately reached a hand down and turned off the video camera.

"Fuck Toby." She shouted "I warned you that we could never let on that I was in the room while this video was being made."

"You have enough footage for that video." Said Toby

Dina considered it and realised that Toby was probably right. Between the blow job and the sex there was probably 15 minutes of footage that would be usable. She probably would have wanted a little bit more just to be safe but Dina felt she had enough to make the porn company happy.

"Ok I guess we probably do have enough." Said Dina.

"Good." Said Toby "Can we just get down to some serious fucking now?"

Dina's heart jumped at this question. She wanted to feel Toby's cock inside her again more than anything. Dina had pretty much always lived in the shadow of her daughter. Lindsay was a young beautiful world famous star but this teenage boy had stopped fucking her and almost pushed her to the ground. He was asking for Dina and the 50-year-old felt more complimented than she ever had in her life.

"Toby honey if you want me then maybe we could go someplace?" suggested Dina feeling like she was a teenager herself again.

"Oh I definitely want you." Said Toby "I want both of you. I want to fuck you both right here right now."

"Toby, we can't do that." Said Dina "It would be wrong."

"Everything that we have done so far has been wrong." Reasoned Toby "Might as well finished it off with a bang."

Dina sorely wanted to feel Toby inside her again but there were lines that could not be crossed and with a sigh she decided to put an end to this whole episode.