“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.
