“What time do I have to be there tomorrow,” Jake Taylor asked his mother as he spoke to her on the phone.
“Well everybody is going to be arriving at about 4, but Jane needs some help setting up so I told her you would be over today to help her,” his mother responded.
Jake’s cock instantly became hard at the thought of Jane Stevens, an old friend of the family and his former babysitter. She was his first crush and object of desire, as he lay awake at night during those awkward preteen and early teenage years, when the body begins to change and masturbation becomes more of a pursuit. Jane was Jake’s sisters best friend, and may a night he would fantasize about her naked body wrapped around him, as she rode him until he exploded. Then there were those times when Jane and his sister Mary would go swimming in the backyard, and Jake would steal away to the bungalow house and watch them as they swam.
He thought she was a strikingly beautiful woman as he saw her in her bikini soaking up the sun on the deck. She stood about 5’5 and weighed about 130 pounds with curves in all the right places. She had nice 34’b breasts that perfectly accentuated her small frame, a nice flat tummy with a little tattoo of a bee that was placed just above her bikini bottom, and long toned legs with nice wide hips, and simply a “to die for” ass. Her face was framed with short cut brown hair, and accentuated with full lips and beautiful green eyes, he thought she looked much like a young Julie Andrews, with a better body. And as she offered her 18 year old body up to the sun gods, Jake would ravage her body from a far and pound his cock for all he was worth.
This situation continued until Jane left for college and Jake became old enough to watch himself, but in the 9 years that passed since she was his babysitter the image of her body never left his head, and the passion in his heart continued to grow. And so it caused him great pain when his mother called a few months back and told him that Jane was getting married, and the wedding would be held at the Taylor’s lake house the following spring. Jake was simply in torment as he thought about losing Jane, and even though she had not shown him the least bit of interest, he knew she was made for him. Through the agonizing months of desperation a plan began to form in Jakes mind, a plan that if successful would lead her into his arms, and if it failed would drive her out of his life forever.
“Sure mom that’s no problem. I’ll see you tomorrow, I can’t believe the wedding is in a 2 days either,” he said as he hung up the phone.
Like all weddings, the last few weeks leading up to it seem to be the most hectic time of all, and the most trying for all involved. Nerves were frayed and everybody was just getting a little sick of everybody else, but it was also much easier for Jake to prepare for Jane. During the last couple of weeks, while the rest of the family was busy helping Jane prepare for the wedding, Jake was quietly stockpiling bottles of vodka, and boxes of chocolates in a little hidden corner of the basement. He had known her for all of his life and knew that she had a very low tolerance, almost an allergy, to alcohol; and a very high affinity for chocolate. His plan was simple enough, inject the alcohol into the candy, get her drunk, and see what would happen next. He spent hours practicing on the boxes of chocolates until he knew exactly how much to put in each individual candy, and for it to look like the candy had not been tampered with. Finally he had perfected his craft to a science, and as he hopped into the shower to get washed he slowly began to pump his cock at the illicit thought of finally being able to get into Jane’s panties.
He finished his shower and got dressed, and while grabbing a box of his “special” chocolates, he slid on a pair of jeans that were two sizes to tight, over his naked body. As he drove up to the lake his cock was rock hard in his jeans as he thought how wrong he was being, but at the same time realizing that sometimes it feels so good to be so bad.
He drove up to the house, and while removing the chocolates from the car, adjusted his huge straining member in his jeans, and then calmly walked up to the door and rang the bell. The door opened and there before him stood the most beautiful woman in the world, in his opinion. At 27 years old Jane Stevens was more than any man could ever ask for. She was dressed in a tight black turtle neck, which showed that her fantastic 34’b breasts had not changed in the nine years since he saw her in a bikini, and clung tightly to her flat belly. Her tight blue jeans gave no doubt that her wide hips and magnificent behind were still “to die for”, and her short brown hair and beautiful face were just as he remembered..
“Jake what are you doing here,” she asked as she warmly embraced him.
“Hi Janey, mom told me you needed some help and you were up here by yourself, so when she asked me to help I said sure,” he replied as he returned her embrace and began to feel his cock grow.
“Oh your mom is such a saint. I really must thank her,” she said as she broke the embrace.
“Oh here I almost forgot, these are for you,” he said as he handed her the chocolates.
“Why thank you Jake. You are such a life saver…wow these are sweet,” she said as she popped one into her mouth.
“Here you can help me move more chairs in from outside,” she said while eating another one.
“Sounds good,” he replied as he followed her outside, and adjusted his cock at the sight of her beautiful posterior.
As they continued to work through the day, Jane continued to eat the chocolates and the effect on her was becomi8ng more obvious to Jake. He began to notice that she seemed much more playful then usual, and started to call him jakester, which was the name she called him when she babysat for him. The constant attention he got from her, combined with the little pats she gave him on his behind, served to swell his cock to gargantuan proportions, and combined with his pants being two sizes two small, his bulge looked absolutely massive in his pants. The effect was exactly what Jake had in mind when he wore the tight jeans, he wanted to draw Jane’s attention to his cock and he was having success doing it. He began to notice Jane stealing glances at his pants when she thought he wasn’t looking, and when he excused himself to go to the bathroom, he left the door slightly ajar and could here footsteps in the outside hallway.
Jane tried to be quiet as she snuck down the hallway to spy on him. She had a million thoughts running through her mind, not the least of which was that this boy was like her little brother and she was getting married to a wonderful man in a few short days, but the size of the bulge in his pants had stirred some natural feminine curiosity in her and her curiosity temporarily overcame her better judgment. She quietly made it to the bathroom, and looked very carefully through the slightly ajar door.
“Oh my God,” she exclaimed silently as she saw the sheer size of his member. It looked to be a good 9 inches long and as thick as her wrist. She had never seen a cock that big before in her life, and as she continued to gaze at it her juices began to flow between her legs, and she began to rub her pussy through her jeans. Her fiancée’ Jim’s cock did not seem to be half the size of Jake’s, and as she continued to watch him her mind came back to Jim and she quickly began to feel the wrongness of the situation, so she quietly crept back down the hall and went back to the family room to wait for Jake.
Jake new she was there, and as he zipped up he smiled with a deep satisfaction at knowing she was now within his reach. He checked himself in the mirror, and the thought of finally being able to fuck the woman of his dreams tonight swelled his cock to mammoth proportions once again. He gazed at himself once again, and satisfied he would have her attention again, calmly walked back to the family room. He found her on the sofa and smiled inwardly as he saw her stare openly at his bulge for a good 3 seconds before meeting his gaze.
“Are you all set,” she asked.
“Ready when you are,” he responded. “We still have a few more things to do, so let’s get to it,” she said as she headed for the outside and he followed.
The rest of the work went rather quickly and Jake noticed that ever chance she got, Jane was openly gawking at the bulge in his pants. She began to flirt more heavily with him, and as she finished up the last of the chocolates, she came over and gave him a kiss on the cheek for helping her out.
“Thanks Jake you have been a great help today” she said as she kissed him.
“No problem Janey. Why don’t we catch up on old times,” he asked her.
“Sure have a seat,” she said as they sat on the sofa, and Jake went to get some sodas that he had spiked with vodka.
They talked for a hours and caught up on all the old times. How she used to tuck him in at night, tell him stories, check his closet for monsters, all the things a babysitter does.
“Do you remember when I got hurt or cut, you used to kiss it to make it better,” he asked.
“Oh yes. You were always the tough little boy and would always hate it when I kissed you,” she laughed as she sipped her soda and lightly patted his thigh.
“Oh yeah that’s me the Hulk,” he said laughing. She laughed very heartily at his joke and threw up her hands, but as she brought them down he had moved suddenly and instead of slapping his knee, her hand slapped his bulge very hard.
“Ah….shit,” he yelled as the pain began to seep through his groin. He bent down and took a couple of deep breaths until the pain subsided, and then leaned back on the sofa.
“Oh God Jake. I am so sorry I didn’t mean it. Are you ok,” Jane said as she stroked his hair the way she did when he was younger. He leaned his head over, and when he saw the concerned look on her face, knew this was the chance he had waited his whole adult life for. He decided this was the point of no return and put his plan into action.
“I don’t know Janey. It really hurts. God it’s never hurt this bad,” he lied as he pretended to be in agony.
“What can I do? Do you want some ice? I should go call your mother,” Jane said as she began to leave, but Jake grabbed her by the arm and pulled her back to him.
“You can’t call my mother Janey. I’ll be so embarrassed, please don’t Janey,” he pleaded with her.
“Ok fine, but we have to do something. Maybe I should call the doctor,” she offered.
“No way! That would be horrible, I would be known as the dips hit with the broken penis,” he said.
“Ok fine, but what do you want to do it looks like it‘s swelling,” she yelled.
“Your right. God I hope that’s normal. Well maybe if I just let the air get to it it would be ok, maybe if I just let it out for a while it will go back to normal. Can you help me to the bathroom please,” he whimpered doing his best to seem incapacitated.
“No let’s do it here. I think we should get it out as soon as possible. Here I will help you,” she said, but he stopped her before she could do anything.
“Janey, look it’s kind of embarrassing. I mean I’m a little shy and I’m not wearing any underwear,” he said.
“Well look I have seen you naked before, and I have seen other naked men before. It is nothing to be embarrassed about and I can see your in great pain, so let’s just cut all the bullshit here and do it,” she lectured him.
“Ok,” he said, but when he tried to reach his fly with his hands he winced in pain and pretended that he could not do it himself.
“would you mind Janey,” he asked as he looked at her pleadingly.
“Not at all, just lay back and relax,” she said as she reached for his fly.
A wave of excitement spread through him as he felt her fingertips on his cock, through his tight jeans and he moaned with pleasure as he felt her fumble with the zipper to open it.
“Ok I’m almost there,” she said as she pulled down his fly.
“Oh God,” she exclaimed as the largest cock she had ever seen sprung into her view for the second time today.
“There is that better sweetheart,” she said as she tasseled his hair.
“Much better. Thank you Janey,” he said as he looked at her and smiled with delight at noticing that her eyes had never left his cock.
“Oh no I still have a problem here,” he said, trying his best to sound sincere.
“What’s the matter baby,” Jane said as she looked into his eyes with a concerned expression.
“Well it still hurts really bad, and I think it’s still swelling because it feels awfully hot,” he said as he griped his shaft.
He knew that if he could get her to touch him that it was all over and she would be his, so he chose his words carefully and tried his best to sound concerned.
“What do you think? Does it still feel warm,” he asked her.
Without thinking Jane immediately grabbed his shaft to see if it felt hot.
“Ouch…That hurts Janey,” Jake said as she grabbed him.
“Oh I’m sorry baby…how does this feel,” she said as she slowly began to stroke his shaft.
“Oh that feels wonderful Janey.”
A fire was now raging between Jane’s legs and even though she felt that it was wrong, somehow she rationalized her actions as helping a friend in pain. She had known this boy for the majority of his life and loved him like a little brother, so when he was in need of help she wanted to help him and when he was in pain she wanted to ease it. A soft moan escaped his lips as she continued to gently stroke his shaft, and served to encourage and validate her actions to herself.
“Does that feel better baby,” she cooed as she continued to pump him. He simply moaned his response and desired to push her to the next step. “Yes that feels so good Janey. It is helping so much. You have always helped me so much,” he moaned as she continued to pound his cock.
“I will always help my baby. You are my baby, so of course I will always help you,” she replied.
“Does it still hurt Jake,” she asked.
“Not as much as before, but still a little bit,” he said while trying to suppress a smile.
“What else can I do for you sweetheart,” she asked.
This was the most important moment of Jake’s life up to this point, and her response to his suggestion would either make or break his dream.
“Can you kiss it and make it feel better,” he asked.
Jane thought about his suggestion, but continued to slowly stroke his cock as she did. Unknown to her was the effect the alcohol was having on her system. In the back of her mind she thought this was wrong, that this whole situation was bad and she should not be a part of it, but for some strange reason she didn’t seem to think of it that way. She still had some rational thought and she thought to herself here I am about to get married and I am going to give a blowjob to the kid I used to baby-sit. Somehow it all didn’t seem real, it seemed like she was in a dream and had no control over her actions. The things that seemed so important to her before like fidelity, honesty, and integrity, all seemed to take a backseat to Jake’s cock. Her desire for it continued to grow, a and as is usually the case, rational thought lost out to desire. Her pussy was on fire as she began to pump him even harder, and as he moaned deeply with pleasure, his heart began to beat a mile a minute, when she pushed his thighs apart and knelt between them.
“Will you kiss it and make it better Janey,” Jake moaned as her mouth came inches from his cock.
“This must be our little secret Jake. Like when you were younger ok,” she asked.
“Oh absolutely,” he exclaimed as he felt her hot breath on his cock.
She slowly and softly kissed the head of his cock, and then while looking directly into his eyes, took him into her mouth. He moaned with joy at the feel of her mouth on him and the sensation of his cock going deeper and deeper into her throat.
“Oh God! Oh Janey….oh your so fucking good…oh it feels so fucking good…oh God…oh please,” he cried as she increased her pace and began to pound his full 9 inches deeper into her mouth.
“Does it feel good baby? I know it does…I know I am good at this…I am a great at head,” she said as she popped him back into her mouth and worked him even harder.
He could not hold out much longer, and when she felt him tighten inside her mouth, she began to suck even harder.
“Oh god Janey…oh Janey...oh..arghhhh,” he cried as he shot his seed into her mouth. Jane swallowed everything and continued to milk him until he was bone dry. She then stood up and kissed him on the mouth, his tongue dancing with hers and tasting his seed on her tongue.
“Well I hope you feel better now Sweetheart. I think it’s time you go,” she said, but as she tried to leave his hand grabbed her arm and brought her back to him. “Aren’t you going to let me return the favor,” he asked as he gently ground his naked penis into her jean covered mound.
“No way honey! You were the one that was hurting and I wanted to help you, but now it’s over,” she said as she pushed away from his embrace.
He pushed her down on the sofa, and kneeling between her legs, he could smell her arousal through her jeans.
“What the hell are you doing Jake. Stop it this instant,” she cried as she tried to push him off, but his weight was too much for her, and as she was pushing him, he began to lightly bite her pussy through her jeans.
“Oh stop it Jake…please…no more…it is wrong...so wrong baby,” she cried as his efforts began to pay off for him and her pleasure began to build.
“Please Janey I will be real quick and it will be our little secret, like when I was younger. All I want to do is taste you the way you tasted me, and give you the same pleasure that you gave me,” he said.
“No baby...please this is wrong we must stop…it is so wrong…oh god it feels so good…so wrong…no please,” she cried as he continued his assault.
“I will be fast and nobody will ever know Janey…please let me taste you…oh please Janey,” he cried.
Her defenses were gone and she could no longer resist the mouth between her legs, and could no longer deprive herself of the pleasure she wanted so badly.
“Ok baby.,” she moaned as she arched her back and forced her jean covered mound farther into his mouth.
He pulled off her shoes and then, while kneeling back between her thighs, unbuckled her button fly, and pulled her skin tight jeans completely off. Now all that separated him from his fantasy was a pair of tight blue panties . He leaned down on top of her and placed his nose up against her panty covered mound and inhaled deeply. The scent of arousal was unmistakable as he began to gently lick her though her panties.
“Oh baby…oh yes,” Jane moaned as she felt his tongue through the thin fabric.
He continued his assault until he could take it no more, and quickly using his hands, ripped her panties completely off her. Jane shivered as she felt the cool air on her hot pussy, and she moaned with delight as she felt his tongue make contact with her.
“Oh God Yes,” she cried as he dove face first into her, using his tongue like an examination probe he explored every millimeter of her femininity and savored the taste along the way. He plunged his tongue into her deeper and deeper, leaving no region ignored nor neglected. His tongue teases her labia and massaged her clit, while his finger slid deep up inside of her. Jane’s response was to slip her hands under her turtle neck and massage her nipples through her bra, while grinding her pussy into his face.
“Oh baby…oh your so good…oh god…don’t lose it baby…oh please…Jake…oh please baby,” she cried as she felt the passion begin to build inside of her.
Jake responded by clamping his hands to her ass and feasting on her pussy like a starving man. His tongue went into overdrive, fueled by all the years of desiring his mouth where it was right now, between the legs of his fantasy woman; but this was no fantasy, it was his reality and he was going to eat her until she could stand it no more.