Anything For Lindsay Ch 05

"Oh god, oh my....," Jason said, in pure pleasure, trying with every ounce of his body to hold back from cuming.

Lindsay was sitting next to Jason, slowly stroking his penis. Jason was completely naked laying on Lindsay's bed. Lindsay was fully clothed in a tank top and a pair of jeans.

"Its only been 50 seconds Jay, hold on, you still got a little over two minutes," Lindsay encouraged him.

Lindsay continued to stroke Jason's little penis, now picking up the speed and concentrating on full strokes of his penis. Lindsay was an expert at giving hand jobs, she had given her first one at 14 years old.

Jason, meanwhile, was trying as hard as he could to ignore the immense pleasure that was surrounding his dick. He was practicing for the bet that was now only 4 days away. He needed to hold out from cuming for 3 minutes, while Cindy gave him a hand job. He had his eyes closed and was picturing baseball, his grandma, anything he could to take his mind of the gorgeous girl jerking his dick.

"One minute and fifteen seconds, you broke your record sweetie," Lindsay shouted as she now picked up the pace even more, this time concentrating on the head of his penis.

"I can't hold out...nooooo," Jason screamed as his dick exploded. Rope after rope of semen shot onto his stomach. The feeling was soo amazing.

"I cant believe you Jason, you are barely getting any better at this, and this is the third time we've tried today. You really want to see me get fucked by Tom, don't you?" Lindsay asked.

"No, I don't, trust me, that's the last thing I want to see," Jason responded, still getting over the mind blowing orgasm he just had.

"Ok well, get on your knees, we gotta train your mind to think cuming quick is not OK," Lindsay said.

Jason, with his cum still all over his stomach, got onto his knees and got ready to suck Lindsay's strap on for the third time today. Lindsay had offered to help Jason train for the bet. She would give him 3 hand jobs a day, and if at any point he could hold out for 3 minutes before cuming, she would finally allow him to see and play with her amazing tits. If he shot his load before 3 minutes, he had to suck the strap on for 5 minutes

Lindsay dropped her jeans, revealing her perfectly tanned legs, and cute pink underwear. She then slipped the plastic cock on and forced it into Jason's mouth. As usual, she verbally encouraged him as he sucked.

"Good job my little cock sucker, you really are getting so good at this, I may have to let you try a real one some day," Lindsay said to him. Her hands were on the back of his head, just in case he tried to stop.

Jason continued to suck away at it. He was almost starting to enjoy these little sessions. He wasn't sure why, but afterwards he would always have a raging hard on, and no matter how recently he just came, would be extremely horny. Lindsay also took notice at Jason's love of sucking her plastic cock.

After the five minutes was over, Lindsay pulled Jason up, and gave him a small kiss. She then grabbed a towel and through it at him so that he could clean himself off.

"Jay...don't you think it's kind of weird that you get a raging boner every time you suck my dick," Lindsay asked him.

"I...uh...it's just from being around you, you are soo hot," Jason tried to play it off.

"Hmmm...maybe that's it, or maybe you secretly think it would be hot to suck a dick," Lindsay said. "Either way, its pretty cute. See you tomorrow, 9 am for the first practice session," she finished, before heading into the bathroom.

Jason quickly got dressed and headed down stairs. On the way out, he saw Cindy, in her robe, watching TV. Cindy immediately noticed Jason walking down.

"Oh, hey little guy. You ready for our bet?" Cindy asked as she made the jerk off motion with her hand.

"I really don't think the bet is such a good idea Cindy, I mean, what's the point, really?" Jason asked.

"THE POINT, LITTLE DICK is that I would much rather see my gorgeous step daughter with a big sexy man like Tom, then a little dicked nerd like you. I need to prove to her that you can't even last 3 minutes during a hand job, let alone sex. Then I need to prove to her that Tom is 10 times the lover you will ever be. What better way to do that then a threesome with both of you?" Cindy explained.

Jason was shocked to hear this come out of her mouth. Cindy had really been nothing but nice to him. He couldn't believe that she thought like this. The look of sadness on his face must have been apparent to Cindy.

"But...on the other hand, if you last longer then 3 minutes, you will prove me wrong, and will have the night of your life. I am a sexual goddess Jason. A threesome with Lindsay and I would be a miracle for you. You should thank me actually. I don't think Lindsay will let you near her tits or her pussy for a long long time, unless you win that is," Cindy explained, this time as sweet as ever.

"Well I hope I can prove you wrong," Jason responded with confidence.

Cindy smiled, stood up, and opened her robe, exposing Jason once again to her breathtaking body. Her breasts looked even bigger then the last time and the light showed off the cuts in her stomach perfectly. Before Jason could even get down to her vagina, she closed her robe back up.

"I don't think you stand a chance, mini meat," Cindy said before turning her attention back to the TV.

Jason sighed deeply and walked out the front door. He walked over to his house and into his room. He jerked off, cumming for the fourth time that day, before he went to sleep. His new plan was to wear his dick out so much, it wouldn't be able to shoot off in less then three minutes no matter what was happening to it.

Once again the next morning Jason showed up at 9am, eagerly awaiting his first handjob. He knocked on the door and Cindy opened it and welcomed him inside. As usual, she sported just a small robe.

"Lindsay's asleep. She was up late last night talking to Tom," Cindy said to him.

"What?" Jason replied.

"Yeah, he came over late last night and said he really needed to talk to her. I don't know what time he left," Cindy continued. "On a good note though, I've been thinking about the bet and I've decided to help you out," Cindy finished, quickly changing the subject.

"Oh? How is that?" Jason questioned, fearing it was a trick.

"If you do a favor for Mr. Mac and I, I will agree to change the length of the hand job from 3 minutes, to 40 seconds," Cindy proposed.

Jason immediately got very excited. He held out for 1:15 last night, surely he could last 40 seconds.

"What's the favor?" Jason asked.

"Just come with me for now," Cindy instructed him.

He followed her into the master bedroom where Mr. Mac was laying asleep on the bed. She got up on the other side of the bed and removed her robe, revealing her spectacular body. She quickly grabbed Jason's head and pulled it to her breast. He sucked on it like it was going to save his life.

"Good job sweetie, suck on my big tits," Cindy encouraged him.

Next she pushed him off and started to take off Jason's pants.

"Take them off, I wanna play with it," Cindy said to him, Mr. Mac sleeping in his robe only feet away.

Jason didn't care and wanted Cindy so badly. He took off his pants, and stood proudly, all 5 inches sticking straight up in the air. Cindy rubbed his penis expertly, even leaning down and sucking on the head of his penis for a minute here and there. Jason was on edge, and once again his only concern was getting to cum.

Cindy slowed her stroke to a slower pace as she began to fully explain the deal to him.

"Mr. Mac is awake now, has been the whole time. All you have to do, in order to change the bet to 40 seconds, ensuring a 3 some with Lindsay and myself for a whole night, and receive a mind blowing blowjob from me right now is...suck Mr. Macs dick for 3 minutes," Cindy told him as she opened up his robe, revealing what looked to be a 9 inch penis.

"It's just like with Lindsay and the strap on. I will be right here waiting to suck your cock once the 3 minutes are up," Cindy said as she continued to expertly manipulate Jason's tiny penis.

"Like Lindsay, Cindy didn't wait for an answer and just pushed Jason's mouth to Mr. Mac's large cock. Jason parted his lips and accepted it into his mouth. He really never had a choice, his dick once again controlled his brain.

Jason opened up his lips and took the large mushroom head into his mouth. He just imagined a night with Lindsay and Cindy and bobbed up and down on Mr. Mac's dick.

"Good boy. That is so fucking hot. Keep sucking and you will have the best night ever. Keep going little dick, worship this man meat," Cindy continued encouraging him.

Cindy grabbed Jason's hair and controlled the pace as which he sucked. She was now bobbing his head up and down pretty steadily. Mr. Mac was groaning and began thrusting his hips into Jason's face.

Jason was a little freaked out, and a little turned on at the same time. It was somehow strange and sexual to be sucking the dick of a man who had twice as much of a "package" as he did. It didn't taste that bad, and it kind of was just like with Lindsay and the strap on. Cindy was right here, naked, stroking his dick, how gay could this be. He was starting to get into it, sucking away at the large cock, still he wanted it to be over with.

"Time," Cindy shouted out.

Jason was ecstatic. He rolled over and watched as Cindy began to suck his cock. She used her mouth and breasts to tease Jason for 15 minutes before she looked up at him and said, "Get ready to black out from pleasure."

Cindy's mouth flew up and down Jason's cock. He was 2 seconds away from release when Lindsay busted opened the door and Cindy quickly shot up.

"What is going on in here?!?!" Lindsay asked.

Jason's heart dropped as he realized that not only was he not going to cum, but his girlfriend just walked in on him getting a blow job from her stepmom.

"I, uh...we...," Jason stumbled, quickly putting his clothes back on and running after her as she stormed out the door.

Jason walked into lindsay's room and tired his best to explain.

"Sweetie, I just went in there because she said she would shorten the bet if I did something and..." Jason stopped as Lindsay cut him off.

"I don't care Jason, I really don't. You are just like every other guy I've ever dated. You can't keep your dick in your pants," shouted Lindsay.

"NO, I CAN!" Shouted Jason. "I promise, I will never do anything like that ever again without you allowing it," Jason continued.

"You have made a promise like that before. How do I know I can trust you?" Lindsay asked.

Jason just stared as the girl of his dreams and realized that he may lost her forever.

"PLEASE!" Jason begged.

"Well...I guess there is one way," Lindsay said as she reached into her drawer to pull out the penis cage. "You have to wear this whenever your not with me," Lindsay added.

Jason was so under her spell, he didn't even need to think before agreeing.

Lindsay walked over to Jason, dropped his pants, revealing his little dick. She clicked the cage on tightly before he even had a chance to get hard again.

"I'm still so upset with you Jason. I really think you should go home," Lindsay said.

Jason stared at her in shock. He had just put the cage on? Didn't this get him back to even, at least so he could stay.

"When will I see you again?" Jason asked.

"I don't know. I may need a few days to get over this Jason. I just caught you getting a blow job from my stepmom!" She screamed at him before locking herself in her bathroom.

Jason walked out of the house and back to his. He felt as if he could cry at any moment. The bet was a little over 48 hours away and he was now horny as ever and locked in a cage. Not only that, but he had just sucked a huge penis in order to get the bet shortened, which at this point didn't matter because Jason would never last even 15 seconds after 2 days of being locked up in this cage.

Thursday, Jason tried to get Lindsay to see him, but no one would even let him in the house.

Friday rolled around and Jason was ready to break the cage with a screwdriver. Luckily for him, Lindsay sent him a text telling him to come over.

Jason jumped out of bed and ran to her house as quickly as possible.

She was in a tiny silk robe and from what Jason could tell, she was completely naked underneath it. She then proceeded to undress Jason, take off him cage, and lastly slip a blindfold over his eyes.

Jason was now laying on the bed, naked, with a raging hard on, not able to see a thing.

Suddenly Jason felt a thin piece of silk material fall onto his penis, sending chills down his body. He then felt his hands being cuffed to the bed posts. Finally he felt the weight of her tiny body and huge breasts being pressed against his chest.

She slid her body up and down his, driving his penis insane with pleasure, but not quite enough to achieve release. Lindsay did this for at least 40 minutes, Keeping him on edge the whole time.

Lindsay slid down and wrapped her breasts around Jason's dick, the pleasure was so great. Jason would do anything to get this blindfold off and see what she was doing to his penis. Finally, she took his dick into her mouth and slowly sucked. Jason was almost weeping at this point, begging Lindsay to let him cum.

"Pleasseeee Lindsay, please, I need..." Jason started.

"I don't really care what you need," Lindsay interrupted him. I have decided what I need from you in order for us to stay together," she began.

Lindsay slid up so that her mouth was right next to his ear. Her huge breasts were squashed against his chest and the head of his penis was pressing, just slightly, into her vagina. He could barely breathe.

"If you want to stay with me, you are going to have to do whatever I say for the next week. No matter what is it," Lindsay whispered into his ear. "If you so much as question one demand, it's over. I will never speak to you again," she continued.

"O...ooo...kkk," Jason barely could speak he was in the most sexually gratifying and frustrating position of his life.

"The first thing you are going to do for me...," Lindsay started to explain her first request. As she did, she pushed down a little on his dick so the head slipped into her soaking wet pussy. "...is lose the bet tomorrow," Lindsay finished.

Jason's mind was blown. He thought more about trying to win this bet then anything else in his entire life and now she told him he had to lose. He wanted to argue, but couldn't risk losing this beautiful girl, whom he was so close to having sex with. He just shook his head in acceptance.

"Good boy, not like you would have a choice anyway, you won't last 15 seconds tomorrow. Especially since I plan on teasing your little penis all night long," Lindsay laughed as her control over Jason finally escalated to it's highest possible point.

Lindsay pulled the head of his dick out of her pussy and got up off him completely. Jason heard some shuffling around a minute later Lindsay was taking his blindfold off. Lindsay was back in her robe, and lubing up her hands. She spend the next couple hours brining Jason as close to orgasm as possible without cuming, and then taking a 10 minute break before doing it again. At one point she spent 40 minutes riding Jason's face. She came four times as he sucked and licked her pussy and ass. Finally, she shoved some panties into his mouth so he couldn't even beg her to let him cum. He was becoming delirious.

Finally Lindsay announced she was stopping, before she put the cage back on. She then turned off the lights, and crawled in bed with Jason. Lindsay fell asleep with in 5 minutes, but Jason was so horny, he didn't sleep a wink all night.

At 10am, her alarm went off. The bet was 30 minutes away. Lindsay took off Jason's cage and teased his dick for 15 minutes, getting it good and ready to shoot off in less then 40 seconds. Jason was as horny, and as depressed as he had ever been in his life.

Finally it was time, Jason walked downstairs in just a robe, awaiting his fate. As he walked down, he saw Cindy and Lindsay's dad sitting on the couch. They were also both dressed in a robe.

The room was all set up, a spot for him to sit, with some towels laid out on the floor where he would soon shoot his load, a stopwatch on the table, some tissues for Cindy's hands. Jason took his spot on the chair and dropped his robe. He was sitting there naked, on display for 3 robed voyeurs. It didn't matter though, because of the situation, Jason's cock was already hard and dripping precum.

The crowd collectively smiled at how small Jason's penis looked paired with the fact that this was actually going to be easier then any of them had imagined. Jason was surprised to see Cindy stand up and take off her robe. Her body was even better then Jason remembered. Perfect large breasts with a sexy cut stomach. Her pussy was shaved completely.

Lindsay grabbed the stopwatch as Cindy squirted some lotion into her hands.

"On your mark, get set, go!" Lindsay announced.

Cindy pushed her perfect breasts into Jason's shoulder as she grabbed his dick and within 3 seconds of her hand touching his penis, Jason came. He screamed out in pleasure as cindy milked his little penis for a sold 30 seconds, emptying out 4 days of frustration.

"Oh my god, that was a fucking joke," Cindy laughed as she wiped off little globs of Jason's cum that had gotten on her hands and arms.

Cindy and Lindsay's dad almost immediately walked up stairs, Cindy still laughing to herself. Lindsay's dad hadn't said a word, but was smiling the entire time.

Lindsay's dad's smile was nothing compared to Lindsay's smile. She was giddy. Jason was so confused as to why she so was so happy.

As if on cue, Lindsay chimed in, "I'm so happy you did what I said Jason, I really didn't want to break up with you, I like you a lot," she said, looking amazing in her little robe.

Jason smiled back at her with a look of acceptance.

"Now let's go upstairs, we need to lock you back up. Then I want you call Tom, tell him that you want him to come over and help you fuck your girlfriend on Saturday. Say it word for word," Lindsay instructed.

"But, that's ridiculous...," Jason began.

"What did I say Jason?" Lindsay swiftly interrupted him. "Just for that Tom will be going first on Saturday. And if you question me again or I find out it wasn't word for word, the threesome will become a twosome, and I will never talk to you again," Lindsay said

Jason simply shook his head. He then walked upstairs to have his penis locked up in a cage, and invite another guy to fuck his girlfriend.