Anything for Lindsay Part 1
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Jason opened the door to Lindsay’s backyard, the large gift tucked neatly under his arm. He scanned the room and quickly recognized a few very familiar faces.
First he saw Katrina, Lindsay’s best friend. She was beautiful, not sexy, but beautiful. Her pale skin and perfect facial features complimented her dark auburn hair nicely. She was skinny, with not many curves, but she had the reputation around school of giving the world’s best blow job. Jason knew at least 10 of his friends who had blown their load in her mouth, one of which was his good friend Tim, who had accompanied him to the party. Tim had told Jason how Katrina would lick his balls, and deepthroat him, but refused to swallow his cum. It was that type of prissiness that really made Jason want to fuck her face.
Next he saw Linday’s dad Jeff and his new wife Cindy. Linday’s mom had moved away when she was young, but soon after, Jeff won the lottery and amazingly enough, right after Jeff won the lottery, he met Cindy. Cindy was gorgeous. She mirrored Denise Richards, but had won best ass on a white girl by penthouse only 2 years before.
His eyes then gazed to Lindsay. Lindsay’s family had been close with his since he was 7. She stood just an inch smaller then him. She had golden blond hair, beautiful deep pink lips, great blue eyes, and the most stunning pair of natural DD tits. Jason would have given anything just to have kissed Lindsay, but she always dated older guys and thought of him as more of a friend.
Lastly, his eyes met the eyes of Lindsay’s boyfriend Brett. Brett was a 6’5, chiseled, black, captain of the lacrosse team. He towered over Jason and his 5’8, 170 pound frame.
“JASON!” Lindsay screamed, running over and giving him a huge hug.
Jason’s penis immediately began to stir as her huge breasts squashed up against his chest and she pecked him on the cheek. She pulled away and started to catch up with him.
Jason dazed off, thinking about how other then Lindsay, and Katie, Jason had never gotten much attention from girls, and definitely zero attention from anyone that looked like Lindsay, and that was only because their families were close. Jason’s only actual sexual experience was with the school slut, Holly, who had blown him a few times and fucked him once. Holly was skinny, with short brown hair, and small but cute b cup breasts.
After the 2 minutes of sex was over, Holly said “with a dick as small as yours, I’d work on my stamina” as she quickly got dressed and left the room. That day confirmed Jason’s reason for lack of confidence. He had a small dick. It stood proud at 4 inches, and would hardly make any girl scream. All of his friends constantly talked about how big their dicks were, making him feel even less confident.
“…and yeah, so I’m going to be home all summer,” Lindsay’s words snapped Jason back into the conversation. It had been 3 years since the two of them lived in the same city.
“Wow, that’s great, we can finally catch up on lost time,” Jason replied.
“Yeah, we could go to the beach so I can work on my tan. Brett says I need to get some color. Oh look, my Aunt just got here, see you later,” Lindsay said, as she began to walk away.
Jason got excited thinking about the prospect of seeing Lindsay in a bathing suit. Every hour with her tits popping out of her famously tight bikini tops, was at least a week of jerk off material, he thought.
The rest of the party was pretty lame, and Jason left early, sick of watching Lindsay and Brett make out. Her tiny body looked so small in his huge arms, Jason was insanely jealous.
“Ring, Ring, Ring,” his phone ringing in his ear.
“He-he-hello,” Jason stammered, answering his cell phone right out of deep sleep. Jason looked over at the clock, 2:15 blared at him in bright red through the darkness.
At first, all he heard was whimpering and crying as he regained his senses.
“Jason, its Lindsay,” she sobbed into the phone.
“I just found out that Brett has been cheating on me all semester, with some slut who lived next door to him,” she explained. “Why does this keep happening to me?” she asked.
“I don’t know, maybe it’s the type of guy you are attracted to, the bad boy type that just cant keep his penis in his pants,” Jason responded
“Yeah, maybe…I just feel so horrible right now, I really don’t want to be alone. You think maybe you could come over with some pot and keep me company?” She asked in an almost irresistible tone.
Jason had to be up the next day at 8:00 for his fist day at his new internship, but still could not resist Lindsay. “Sure, ill be over soon,” he blurted out, almost too excited for the situation.
Thirty minutes and 25 dollars later Jason was at Lindsay’s front door waiting for her to come down and let him in.
She opened the door and Jason’s eyes almost fell out of his head. Their stood the sexiest girl Jason had ever seen in real life. Her makeup was running from the thousands of tears that had ran their way down her cheeks, but her body was incredible.
She wore the tightest white tank top he had ever seen. Her enormous breasts pushed against the thin material, almost exploding out. He could perfectly see the indentation of her nipples through the shirt. To complement the top, she was wearing tiny little shorts that barely concealed anything at all.
As if it were no more then a planned tease, she through on a jacket and some sweat pants as she walked to her room with him.
They smoked a joint and discussed her dating history. All the boys whom had screwed her over through the years.
“You know, maybe I need to date a nice guy…more like you,” she said, the words sounding like music to his ears. As quickly as she brought it up, she dropped it, and took another hit.
As the night wore on, Lindsay cuddled up next to him and fell asleep with her ass right against his crotch. It took every single ounce of self control he had not to just start humping her clothed rear right then and there. She had to feel his small hardness up against her. He debated making a move on her before eventually falling asleep himself.
At 8am he woke up and dragged himself out of her house, before heading to his first day of work. That night he was supposed to have dinner with Lindsay.
Her showed up at her door around 8 and made small talk with Cindy while Lindsay finished getting ready. Finally, 40 minutes later, she came down, dressed to kill. She wore a tight, short dress, that amplified her amazing chest even more, while drawing lots of attention to her beautifully shaped legs.
As they walked to the car, Jason couldn’t help but feel like a little boy next to this woman, who with her heels, now stood a full inch over him.
They arrived at the expensive restaurant she had picked out, and sat at a tiny table in the corner. As they ate, he could not take his eyes off her breasts. It was almost like she was begging him to stare at them.
“Can’t keep your eyes on my face, can you Jason?” She giggled.
” I uh, I’m really sorry, I uh—,” Jason stammered.
“Its OK, I’m used to it, trust me,” she interrupted him. “You know, maybe we should consider this our first date. I am having fun with you, and its clear your enjoying my company. Is that OK with you? The possibility of us being more then friends?”
“Well, um, you know, well, yeah I think so, I…I…,” Jason was at a loss for words.
“Haha, wow, didn’t realize how nervous I made you. Its OK. Its weird for me too. Of coarse If we were to make this happen, you would have to agree to a few things first,” She said as a huge smile spread across her face.
“Like what?” Jason asked.
“Well, all of my other relationships have been all about the sex, and my tits, and blow jobs, but I want this one to be different. I want it to move slowly. Also, my last boyfriends were so flirty with every girl they saw. I want you to be all mine…if that’s OK?” Lindsay asked, her gerogeous smile letting him know she already knew the anwser.
“Yeah, I’ll do whatever it takes to make you happy,” Jason said as the smile on Lindsay’s mouth grew.
“If this relationship is going to work, you are going to have to have that attitude. I am not going to be easy and I believe it is a privilege to have me on your arm and have access to my body, one that should be earned. In this past, I have let my boyfriends have too much control and fun and have always gotten hurt. This time I want it to be about me being in control.” Lindsay said.
“Do you think you could handle that?” she asked.
“Yes,” replied Jason.
“Good, now pay the check and lets go, the Hills start in 15 minutes and we need to be home to watch it,” ordered Lindsay.
They got back to her house and sat on her bed, beginning to watch the show. Every time she leaned into him, she found some way to rub he breasts against his arm, or give him a great view down her dress. His small erection was becoming quite obvious.
“Aww Jay. Are you getting a stiffy?” Lindsay giggled, pointing to the tent in his pants.
Jason’s face turned red and he tried to get some sort of slick line out, but she interrupted him again.
“It’s OK, its getting late, you can go home and jerk off…just make sure you think about me while you do it,” Lindsay said as she started to get off the bed.
They walked out the front door and Jason moved into to give her a kiss on the lips, but just as their lips were about to meet, Lindsay turned her head so it was nothing more then a peck on the cheek.
“Goodnight Jason. Happy jerking!” she said as she closed the door.
The next night began the same way as the first with Jason picking up Lindsay, taking her to an expensive dinner, and ending with them on her bed watching a chick show. This time Jason leaned in for a kiss and to his surprise she kissed him back. He was actually kissing Lindsay Mac, the girl of his dreams.
As they made out Jason rubbed his hands down her back and began to reach around for her gorgeous breasts, the breasts he had jerked off too since he could remember jerking off. Just as he began to touch them, she slapped his hands away and stopped kissing him.
“No, bad boy,” she said to him, much they way a master would yell at a dog.
“I thought you agreed to move slow? I will tell you when you can touch my breasts. You haven’t earned that yet,” She said to him, this time in a more playful tone. Jason was heartbroken. He wanted so badly to see and feel her marvelous tits, only to be denied when so close.
She got up and started walking to the door.
“Next time, behave, and maybe you’ll get to cum in my room instead of jerking off in yours,” Lindsay said as she closed the door. Again Jason was left to frivolously jerk off while looking at school pictures of Lindsay.
The next couple days Jason worked late, and they missed each other. During those two days, Jason must have jerked off at least 6 times, all while thinking about his 30 seconds of kissing Lindsay.
Friday night came and as usual they ended up back on Lindsay’s bed. This time it was following another expensive dinner and a three hour ballet. Jason was rewarded for his patience at the ballet, as he was now in the midst of a 5 minute make out session with Lindsay. This time he remembered to keep his hands to himself. She stopped kissing him, gave him the an almost evil smile, and started to take off his shirt.
“Get naked,” she said to him in a very demanding, yet sexy tone
“What?” Jordan looked back at her in surprise, as she was fully clothed.
“Get naked. I want to see if your dick is really a small as Holly Ramirez said it was,” she said with an enormous smile. “Don’t make me ask you again,” She continued.
Jason’s face turned as red as Lindsay’s dress. His whole body trembled as his hands reached for his belt to drop his pants, and finally his boxers. He now stood completely naked, sporting a raging hard on, in front of his dream girl who was completely clothed.
“Awww!” Lindsay said as she now was smiling so much she could barely contain herself. “Come lay down, I need to measure your cute little dick.”
The words pained him as she mocked his smallness, yet he was still so turned on. He laid on his back as she sat besides him, right next to his torso. She pulled out a ruler, and held it next to his dick.
“Oh my god, you’re barely even 4 inches!” she screeched.
She then pulled out a toilet paper roll and slid it over his erection. It easily fit, barely even touching the sides.
“Its official, this is the smallest dick I’ve ever seen,” she said. “Most of my other boyfriends had 7 to 8 inch cocks and used them all the time to make me cum. I hope you can use your mouth to make me cum,” she said in such a straight forward and seductive manor.
She slid her panties off, while keeping her dress on. She slid down over Jason’s body, pinning his dick down against his stomach. She slid up and down his dick once before sliding up to straddle his face. Jason opened his mouth and sucked and licked at her clit like his life depended on it. She rocked back and forth on his face, putting all her weight on him, like it was a dick she was fucking. She slid her dress down over his head so all he could see was darkness. Her moans were enough to keep Jason hard.
“Oh god, eat my pussy, peewee, make me cum all over your face, show me I can live with your tiny cock.” she shouted.
Jason thought it was strange that his erection grew stronger at her words. He continued to pleasure her, determined to show her that he could make her happy.
“Fuck my pussy with your tongue” she groaned. Jason darted his tongue deep inside her, tasting as far up as he could. He went back to her clit, sucking it into his mouth and vibrating on the sweet spot with his tongue. “Oh….my…I’m cumming!!!!” she shouted as a flood gate of juices erupted onto Jason’s face. After she was done, she dismounted his face and rolled her dress back down.
“I may be able to keep you and your 4 inch dick around, sweetie, isn’t that such good news?” she asked.
She looked back at his dick, precum was sliding down the shaft. She took one finger and spread the precum around the head of Jason’s dick, making him shiver. She then began to slightly stroke him, barely touching it, yet stimulating him enough to drive him crazy. At the moment she knew he was the weakest, she began to interrogate him, as she continued to slowly stroke, keeping him on the edge.
“How often do you masturbate?” Lindsay asked him, staring deep into his eyes.
“At least once a day, sometimes two or three,” Jason responded, her hand on his dick was like truth serum.
“What do you think about while you jerk your little dick?” Lindsay continued the questioning.
“A lot of different things,” Jason moaned, as her stroking quickened.
“Do you think of me?” she giggled.
“Sometimes, more lately,” he anwsered. He was about to cum when she lifted her hand off his dick.
“Awww, do you have to masturbate?” Lindasy asked, as Jason shook, his almost orgasm denied.
“Well I am always horny, so it really helps relieve the pressure,” Jason told her, praying she wound start jerking him again.
“Brett told me that he was jacking off when the girl next door knocked, and if he hadn’t been so horny from masturbating, he probably never would have cheated on me. Jason, I need you to promise me you wont masturbate anymore. I cant have another guy cheat on me,” Lindsay explained.
She put her hand back on his dick, trying her best to keep him on the brink of orgasm.
“I dunno…I uh…I don’t think that’s necessary, I would never cheat on you,” Jason barely got the words out, as he had never needed to cum so bad in his life
“Jason, if you want this relationship to work, if you ever wanna see these tits or feel your tiny little dick in my mouth or vagina, you need to promise me that you wont masturbate anymore,” Lindsay laid the bad news on him. “If you promise, I will reward you with an orgasm.”
“I promise, I wont jerk off…please make me cum Lindsay,” Jason shouted. He would have said anything for some release.
“Great!” Lindsay said, as if she had just won an award.
She immediately let go of his dick and kissed him on the cheek. “Go ahead, finish yourself off,” she said.
Jason was shocked, was she really not going to finish him off, herself?
“Come on, I’m tired, Grab your little dick and beat it,” she ordered.
Jason was horrified. He was already standing naked in front of Lindsay mac, as she was fully clothed. Now she wanted him to jerk off for her? He needed to cum so badly he reaqlly had no choice.
He laid down on her bed, put his hand around his dick and started jerking it. Staring at Lindsay’s tits through her dress, it didn’t take long for the cum to start bubbling in his balls. “Cum for me pewee, squirt that icky white stuff,” she whispered in his ear. He felt his heart stop and his whole body go numb.
“UHHHAHAAAA!” Jason screamed as he erupted all over his stomach and chest. It was the most amazing orgasm of his life. He could hear lindsay laughing in the backround as he shot rope after rope onto himself.
Lindsay threw an old dirty towel at him and walked into her bathroom. Jason cleaned himself up and got dressed.
Lindsay came out and grabbed his hand, leading him to the front door. “I’m so glad you promised not to jerk off anymore. It will be so good for our relationship,” She smiled. “Night,” she said as she pop kissed him on the lips and turned back in.
It hit Jason on his drive home, his favorite activity of all time was now off limits to him. He didn’t even care, he was so happy to be with Lindsay, he would do anything to keep her.
It had been four days since Jason had promised Lindsay he wouldn’t jack off anymore. Four of the most painful days of his life. He had no idea how hard it would be to not have an orgasm. He was on edge at all times, and constantly found himself sporting a raging hard on. Tonight, he thought, it would all pay off. Lindsay had the house to her self for the night, and Jason was coming over for take out and a movie in.
“Hey baby,” Jason said as Lindsay opened the door. His smile was huge as he knew tonight he would finally get to blow his load.
His smile grew even more as he saw she was only wearing a tiny, thigh length, robe. Her breasts were barely contained by the little robe. “I’m going to change and then we can eat,” she said.
Jason followed Lindsay to her room. Right as she got to the doorway, she dropped her robe, exposing her extremely sexy back and her luscious ass in a very small thong. Immediately his penis began to harden in his pants. Please turn around, was all he could think. She turned her head, gave an evil smile, and shut the door in his face. “Don’t be such a pervert,” she said, in a laughing manor. The sides of her breasts were now burned into his mind.
She came out in some conservative PJ’s and they began to eat dinner and make small chat. “So I told Cindy about your problem,” Lindsay said, starting a new topic out of nowhere.
“My problem?” Jason asked.
“You know, about your small dick,” she said, so matter of factly.
Jason froze, not sure if she was kidding or not. Did Lindsay really tell her new step mom about his small penis? How could she do that to him?
Lindsay continued, “She was really helpful. The guy she dated right before my dad, was a real rich guy with a tiny penis, just like you. We talked for hours about positions, coping mechanisms, ways to spice it up.”
Jason was now hard as a rock, knowing that these two gorgeous women had discussed in length, his penis, and how small it was. He also loved to hear that she cared enough to try this hard.
“She even gave me three gifts. She said if we used them correctly, it would completely make up for your lack of size,” Lindsay finished.
“What gifts?” Jason asked, his mind in a whirlwind.
“It’s a surprise silly. You will get one tonight, but the others you must earn,” she giggled.
The rest of dinner Lindsay talked about her life, and a fight she had with Katrina. Jason tried to listen, but all he could think about was what the gifts were.
Lindsay got into her bed as Jason cleaned up. She started the movie before he was done. When he came over to sit, she asked, “Don’t you think the movie would be more fun to watch if you were naked?”
Jason opened his mouth to enquire further, but Lindsay just looked him dead in the eyes, smiled her amazing smile, and nodded her head.
Jason took off his t-shirt, and pants, and finally his boxers. His 4 inch woody stood at full mast. Lindsay’s smile grew.
“Awww, its even cuter then I remember,” Lindsay laughed.
Jason didn’t really know how to sit, what with his erection jutting out in front of him. Lindsay spread her legs and had Jason lie on his back with his head on her chest. This was as close as Jason had gotten to her breasts and he was instantly in heaven.
About 15 minutes into the movie Lindsay began to gently stroke Jason’s cock. She handled it like it was her toy, flicking it back and forth, slowly caressing it, jerking it. After 10 minutes Jason was on the edge, about ready to shoot, when she stopped.
15 minutes later she started to play with his dick again, this time stroking and squeezing it more then the first time. Again, right as he felt his orgasm build, she calmly let got of his penis. It bobbed up and down, as hard as humanly possible. His dick was purple and the precum was now streaming out. It took everything he had not to stroke it himself right then and there.
This starting and stopping went on for the next 45 minutes, until finally the movie ended and Lindsay said, “God am I horny, your mouth ready, baby?”
What?? Jason thought. He was on the edge. He was the one who hadn’t cum in 4 days. He was the one who just had his cock teased for an hour and forty minutes.
Lindsay got up and went to the bathroom. Minutes later she immerged in a long red skirt and a matching red bikini top. Jason’s rock hard cock continued oozing precum as his whole body shook. Her DD breasts looked the best he had ever seen them. He instantly forgot about any anger he had towards her.
She wasted very little time in climbing onto his face. “This time, we are going for two,” Lindsay said to him as she rubbed her clit on his mouth. So once again, Jason was in total darkness, licking and sucking like his life depended on it.
“Oh god, yes, stick your tongue deep in my pussy…suck my clit, harder!” Lindsay shouted directions to him, lost in pleasure. She screamed and her whole body pressed down on Jason’s face as her orgasm ran through her whole body.
“Good job baby, one down, one more to go,” Lindsay complimented him. She was now humping his face with some vigor, grinding her pussy against his mouth.
“Show me size doesn’t matter, work that tongue,” she added.
10 minutes later and Jason’s tongue and mouth were so sore, he could barely keep going. “Don’t give up yet, pewee, I’m almost there,” she shouted. She now took her pleasure into her own hands and grinded her clit on his tongue so hard, she almost suffocated him.
“Fuuuuuuucccccckkkkkkk,” Lindsay screamed as her second orgasm hit her. She got of his face and collapsed on the bed next to him.
“That was amazing Jason, you have earned gift number one!” she screeched.
Lindsay went into her closet and pulled out what looked to be a small metal and leather cage. Jason was confused, but could tell Lindsay wasn’t, as the smile on her face could not have been bigger.
“It’s a cock cage! To keep you from cheating on me with another girl, or your hand. Cindy said it will ensure trust and let you know that you belong to me, especially your dick,” Lindsay explained. “For now, I need you to wear this whenever we are not together,” Lindsay said, as Jason began to fully comprehend the situation.
Jason’s faced began to show a look of pure horror. He couldn’t wear that. This had gone to far. Why did he have to wear that? He couldn’t.
Lindsay sensed his fear and walked up next to him, so Jason’s cock was now pressed squarely against her stomach. Her Breasts were squashed up against his chest, and her mouth was inches away from his. She let her hands graze across the entire back of his naked body, sending chills from his spine to his cock.
“Please, for me,” she whispered into his ear as she began to stroke his cock again. Lindsay knew that the combination of 4 days without relief, and her constant teasing, would make him putty in her hands.
“I…I…don’t know Lindsay. I mean, its pretty stupid for me to wear that, you know you can trust me,” Jason tried his best to stand strong, when every fiber in his body screamed, do whatever she wants.
Lindsay frowned, and then began to slide her body down to the ground, stopping when Jason’s penis was aligned with her goddess like breasts. She wrapped the bathing suit clad breasts around his small penis, completely engulfing it.
“Jason, won’t you please wear it. It’s only for a week, and I promise it will be worth it,” Lindsay said.
She was afraid to move her breasts too much around his dick and make him cum already. He had to agree to wear the chastity device first.
“I…um,” Jason could barely get a sentence off, his penis completely controlled his brain at the moment.
Lindsay removed her breasts from his dick as it sprung back into view. It was almost gushing precum. She gently licked down the base of his cock, teasing the head with her lips for a second before stopping.
“Just say yes Jason, and then you can jack off into my mouth, and soon enough I will suck your little dick into the back of my throat,” Lindsay offered.
“Yes…YES!” Jason screamed and immediately grabbed his dick.
“Excellent!,” Lindsay smiled. “Now fill my mouth with your cum.”
It took less then 15 seconds of Jason slamming his little meat. He moaned out in pleasure as he shot the biggest load of his life into her mouth. After finishing, he collapsed onto Lindsay’s bed.
Lindsay got up off her knees and leant in to kiss Jason. Jason, still in a daze from his enormous orgasm, opened his mouth to kiss Lindsay back. Right away he began to notice that she was forcing all of his cum into his mouth. Within seconds he has his whole load sitting in his mouth.
“Swallow it sweetie…If you ever want me to,” Lindsay said.
Jason’s stomach almost turned over at the thought of the idea, but he gulped it down anyway. He closed his eyes, in disgust of what he just did.
He opened them to a “click” sound, and a tight pressure around his dick and balls. Lindsay had just locked his penis into the cock cage she had brought out. She put the key on her necklace and let it dangle in between her breasts.
Jason stared at her massive tits and the key to his dick that now dangled in between them. Now, more then ever, those tits controlled him in every which way. He would do anything to see them, and anything to get this cage off.
“Don’t worry little guy, there’s a pool party on Saturday, I’ll take it off for that,” Lindsay said, acting as if that was doing him a favor.
She went back into the bathroom and yelled, “Just get dressed and let yourself out…I’m gonna take a shower and get some sleep…see you on Saturday.”
Jason got dressed and started walking back to his house. He had been dating his dream girl for almost 2 weeks now and it was nothing like he had thought it would be. He was cumming less then before, and he would of seen this much of her body by going to the beach with her. Now to make matters worse, his dick was in a cage. He realized he was the definition of pussywhipped…and the only pussy he was getting was with his mouth.
He laid down in bed and flipped on the TV. A new Cinnemax soft-core porn was starting. He watched the big breasted actresses make out and his penis grew. Pain suddenly shot through his cock as his hardening penis hit the end of its cage. There was nowhere enough room for his penis to grow.
Jason turned off the TV and tried to think about baseball.
He was in for a very long couple of days.
Part 2 cumming soon…