Jimmy's Plan

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Unlucky guy gets lucky with woman & her sister.
4k words
4.33
181.4k
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Part 1 of the 9 part series

Updated 10/25/2022
Created 03/11/2002
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Canoe
Canoe
35 Followers

Jimmy was 20 years old and had been back in the US for two months. Having spent 3 years away, in the Army, it was difficult making the adjustment of once again living at home. Things had changed considerably since he left. One of his younger brothers, 18 at the time, had a live in girl friend at his parent's house. His parents seemed to seemed to accept it, thinking the girl always slept in a bed in the basement. Jimmy often wondered how they could be so naive.

The house was a pretty standard rambler with 3 bedrooms, a medium sized kitchen and a living room. Jimmy was a happy go lucky sort that drank heavily and was involved with several women. He stayed out late during the week and came home early in the morning on weekends. He was always horny and got a hard-on if women just touched him. He thought about sex so much that when you fucked a girl he usually came within a minute of entry. It was an embarrassment for him but fortunately youth saved him and usually within a few minutes he was hard again and was able to satisfy his partner.

His father was working as a laborer (best job he ever had) and had him away from the house doing odd jobs here and there. His mother was a 5"8" Plump women who, when she was home, dressed in those thin housedress's, popular for her time. She wasn't an attractive women but she wasn't "butt ugly" either. It was from her that Jimmy got his happy go lucky manner and devil may care attitude. She was also a horny gal and once while Jimmy was in the service she had had an affair with a guy she worked with. It got to be messy but eventually his parents stayed together.

One Saturday morning life in their household was about to change.

Friday night Jimmy had gone to one of the clubs in town. He met an older gal, about 35. They talked, danced and drank and Jimmy, after they had had several drinks decided to use a line he had used many times in Europe which worked very well for him.

He looked her directly in the eye, with no smile and an unwavering stare and said "I want to take you home and rape you!!" She responded with a throaty "you do?" Again with no change in expression, Jimmy said, "you need a big cock!!" She was his and he knew it from the look in her eyes. Once again it worked.

He never understood why it worked…it just did!! Was it the directness of the question? The excitement of a friendly rape? Jimmy didn't know and quite frankly he didn't care…it worked and that's all that counted.

He had noticed that this same type of directness worked equally well when he wanted other things from women. He felt that maybe, just maybe the directness put them off balance and they didn't know what else to do except …agree!!

Music came to an end and Jimmy and his new friend "Sarah" made their way to Jimmy's car. He told her they would have to go to her house as his was too far away. When they entered the door of her apartment they were greeted by the baby sitter, she had two small kids, 6 and 10. Both rushed and hugged their Mommy.

The baby sitter (an attractive girl, maybe 30.) turned out to be her sister who lived just upstairs. Both Sarah and her sister were blond, with long hair and long legs!!

Sarah grabbed the two kids and took them off to their bedroom to put them to bed. This left Jimmy with the sister.

The Sister looked and Jimmy and said, what the hell are you doing here…you're kind of young for my sister aren't you?? Jimmy had drank enough so this sudden attack didn't phase him, instead he grabbed her by the shoulders and said, after I'm through with Sarah I'll come upstairs and give you a little taste of what I'm going to give your sister.

Taken back, the sister flushed and Jimmy released one hand and placed it on her left breast squeezing the nipple through the fabric of her blouse. The sister's eyes closed and Jimmy knew immediately, no matter what she said from this point on…she also was his!!

He then released her and said go upstairs, I'll leave the door unlocked, give us 20 minutes and sneak back down and you can watch. The sister was shocked at the invitation and protested saying I've never done that and I would do that…. Jimmy just said, shut up and do it…you know deep down you want to and…you will!!

The sister was weak at this point and Jimmy knew he could have his way with her there and then but he wanted the time to be right. He didn't want to spoil his plan for the evening!!

Sarah finished putting the kids to bed and returned to the living room. Her sister said, Sarah, I'm going up now…see you tomorrow. Jimmy escorted her to the door saying just loudly enough for Sarah to hear…it was a pleasure meeting you and I hope we will meet again.

The sister flushed again and left!!

Sarah said, Jimmy that was awfully nice of you but I hope she's okay she seemed a little nervous!!

Jimmy hugged Sarah and gave her a deep kiss. His tongue melted any supposed resistance Sarah had felt she needed to convey. She wanted sex with this young stud and that was the only thought she had in her mind. Little did she know what the evening would bring, Jimmy had his plan!!

While continuing the kiss, Jimmy walked Sarah backwards toward her bedroom, his hands working the zipper on her dress. As they passed through the door Jimmy made sure he left it slightly ajar so Sarah's sister would have an unobstructed view of what was about to take place. When Sarah was backed up against the bed, Jimmy dropped his mouth to her neck and began to suck on the muscle between her neck and shoulder. Sarah reacted by grabbing him by the back of his head and pulling him to her. He pulled her dress down and let it drop to the floor. As she stepped out of it she also stepped out of her high heals. She had on her sexiest bra, panties and garter belt. (The best Victoria's Secret had to offer) Jimmy undid the snap on the bra and removed it.

Sarah has small perky Tits and her nipples were hard as a rock. Jimmy then moved his hands to her hips, looped each thumb in her parties and started slowly to drop to his knees. As he pushed down his lips came in contact with her beautiful tits and he sucked first on the left and then the right. Rolling the nipple in his mouth, sucking hard and pulling the tit outward. He stopped there for a moment, released her nipple and began to lick the under side of her tit. Sarah was going wild. She had had many men suck her nipples and attempt to stuff her entire tit in their mouth but never had she had a man tenderly lick the under side of her tit. Sarah, even though she was 35 and she was with this KID, a kid that she couldn't understand where he got such expertise, had her first orgasm!! Her knees buckled slightly.

This did not go unnoticed by Jimmy. He began to kiss her on her flat tummy and down to her navel as his knees reached the floor. Her panties were now on the floor and he could smell the warmth of her pussy but even more was the pungent odor of cum. Jimmy almost lost control; pre-cum was oozing from his cock. He looked up at Sarah who truly looked better undressed than dressed. Something you can't say for all women. Jimmy loved skin, many men liked sexy lingerie or dresses, etc., but to Jimmy that was all "fluff" what really counted was SKIN!! It was smooth to the touch, warm and something he could never get enough of!! Through the corner of his eye he could see Sarah's sister standing hidden in the doorway. He smiled to himself; he knew she would be there. He had an instinct about what women liked and didn't like and once again he picked it right. His direct approach won again…

Jimmy spread Sarah's legs slightly and ran his tongue over her shaved pussy. He loved shaved pussy…no hair to get in your mouth! He licked the lips gently, first the right and then the left lip and then ran his tongue down the center of her opening pussy. He drove his tongue in as deep as he could and brought it to her clit. Sarah jerked and moaned as Jimmy sucked on her clit. He rolled it between his upper lip and tongue and then gently nibbled on it with his teeth. Sarah had her second orgasm!! Jimmy glanced at Sarah's sister in the doorway as he rose to his feet. She had her dress up around her waist and her hand planted firmly in her panties. She was finger fucking herself and enjoying every minute of it. He loved being watched and Sarah's loss of control was feeding the fire of voyeurism burning in his brain!!

Sarah was now lost in a world of pleasure, she heard nothing, saw nothing and was only waiting for direction from her young lover. Jimmy grabbed her by the side of her head, turning her back toward the doorway and kissed her deep, thrusting his tongue into her mouth, she had her eyes closed with passion, he was looking directly at the sister who now was working her clit at a furious pace!! Jimmy places his hands on Sarah's shoulders pushing her to her knees. Unconsciously, she reached out, unzipped his pants and pulled his cock out of his boxers. It amazed Sarah, no novice to a hard cock, at just how hard a young mans cock could be!! It was like iron!!

Jimmy had been leaking pre-cum for quite some time and now it was running down his very hard shaft. Sarah, with an expert move, went to the base of Jimmy's cock and captured the cum on the tip of her tongue. She drew back her head and relished the taste…before engulfing the head in her mouth. Messaging his balls with one hand and working the shaft back and forth Sarah sucked all the pre-cum from Jimmy's cock. Jimmy was so excited, from Sarah's experienced touch and her sister watching that he couldn't hold back any longer. The explosion, blasted against the back of Sarah's throat, gagging her. It was more than she could handle. Cum ran out of her mouth and what didn't…she involuntarily swallowed!!

Jimmy pulled Sarah up and threw her on the bed!! He may have just cum, but he was so hot he had to have Sarah's pussy. Positioning himself in a 69 position he went to Sarah's pussy. Putting his hand on her stomach and pushing down and upward he exposed her clit. From this position he was able to encircle her clit with his mouth, suck her clit deep into his throat and stroke the top of her clit with his tongue. Sarah had never experienced anything like this…she immediately exploded with an orgasm. Jimmy had been taught this technique by a hooker in Europe. She called it the Butterfly!! The effect is to draw out the clit, flatten it and stroke it in a manner impossible from any other angle. It had always worked for Jimmy and this was no exception.

Sarah's sister must have gone to the kitchen because she was now in the doorway with a cucumber fucking herself!! Jimmy's plan was in full swing Sarah, curled into a ball, back to the doorway, closed her eyes and either passed out or went to sleep Jimmy couldn't tell which, either way she was truly OUT!! The booze and orgasm had taken its toll. Her sister was, at this point was preoccupied with her "veggie" and totally oblivious to the world around her. Jimmy jumped off the bed and walked toward her without being noticed. Once in front of her he put his hand on the cucumber and pulled it out. With a single motion he tossed it on the bed leaving the sister humping the air, she just couldn't stop the motion. Jimmy stuck his finger in her cunt, hooked her pubic bone and began to pull her toward the bed. (She wrenched with pain!) It was a site to see, the sister continued fucking his finger as he directed her across the room to the bed.

Jimmy's plan was to make her beg before he fucked the bitch. Her pussy was soaking wet and Jimmy knew she had had at least one orgasm but he also knew she wasn't ready to stop!! His cock was still wet with his cum and Sarah's saliva so he sat her on the bed and forced his cock into her mouth. She eagerly accepted it and began to lick and suck the cum/saliva mixture clean. Jimmy was truly enjoying this but he had other plans. He pulled his cock out to a loud suction sound!! The sister was bewildered; Jimmy nearly tore her dress off. He sensed this sister loved being rough and he knew that was how he would get her to beg!! He made her get on her hands and knees on the bed, close to her Sarah. Sitting on the corner of the bed next to her with his left hand he reached under and grabbed her left tit and began to twist the nipple. Her breath sucked in as she felt the pain. Tears of joy formed in her eyes.

With his right hand he started to finger fuck her wet pussy, shoving his middle finger deep into her receptive cunt. He pushed down with his hand so as he was stroking in and out he was also rubbing her clit. Between the pain of her nipple and the shear pleasure of her pussy all she could do was cry with joy. Jimmy then switched nipples and began to twist the right one even harder, small sounds of pain began to escape the sister's mouth. Knowing she was on the brink of Cumming, he removed his now soaking hand from her pussy. She began to beg, NO, PLEASE DON'T STOP!! Jimmy wasn't ready yet to bring this to an end…he had a plan!! He placed his middle finger at the tight entrance to her beautiful asshole.

Feeling Jimmy's finger she tried to move away saying…No please don't…I've never…ehhhh!! Jimmy shoved his middle finger down to the knuckle in her "virgin" ass. He could feel the muscles tighten on his finger…it felt fantastic and he began to wonder what it would feel like to have his cock in those tight quarters!! Jimmy was now leaking cum and tried hard not to cum!! He started moving his finger in and out slowly; the sister's cries became moans of pleasure. He removed his left hand from her tit and used it to enter her pussy. He could actually feel his fingers inside her touch each other through the membrane. Juice was now nearly running from her pussy and he used the lubrication to message her clit.

The sister was out of it, she didn't know if it was day or night and she didn't know for the moment where she was or with whom!! She was lost and Jimmy knew it!! Now for the next step in Jimmy's plan. He removed his hand from her cunt and with his left hand began to spank her!! It was a spank and rub motion!! The first swat wasn't too hard but the next one brought her back to reality!! She moaned with pain, then the third, fourth, fifth and sixth. Her bottom was cherry red.

She was confused and wanted to climax but now the spanking was increasing her excitement, all she wanted to do was be fucked and fucked hard!! Now Jimmy knew the time was right and he began talk to her…what do you want bitch…eh?? You like this don't you??? She moaned YESSSSSSS!! You want me to fuck you??? YESSSSSSS!! Then let me hear you say it bitch…tell me what you want!! Jimmy's plan was in full swing now, knowing she would now do anything he wanted!! She begged PLEASE FUCK ME!! PLEASE!! PUT YOUR COCK IN MY WET PUSSY AND FUCK ME!! PLEASE…PLEASE!! That's what Jimmy wanted to hear. He pulled his finger from her ass, lined up from behind and slammed his now iron hard cock into her pussy!! She screamed with joy dropped her head looking down…it was then she noticed Sarah was staring at her with a weird smile on her face…she cam immediately!!

Jimmy had no idea what was going on.. his eyes were closed and he was trying to enjoy this fuck. He was aware of the fact that her pussy was so wet and receptive and his cock so hard that he wasn't getting much feeling from her pussy. He was slapping around in side her gapping hole. He wanted something tighter!! He opened his eyes and looked down at the beautiful tightness of her asshole. It was what he saw then that almost make him forget what he was doing.

Sarah was awake!! Laying on her back with knees drawn up she had slid her head under her sisters tits and was now sucking hard on her sisters right tit!! With her left hand she was frantically rubbing her clit!! It was such an erotic sight that it made Jimmy crazy with lust!! Jimmy at this point LOST IT; he was now a guttural animal that wanted to FUCK and FUCK and FUCK and the more obscene, the more dirty …the better!! Sarah removed her mouth from her sister's tit and said "Fuck him back Ellen, slam your ass against his hard cock and swinging balls" Hmmmm, her name was Ellen, thought Jimmy, it hadn't occurred to him until this moment that he didn't know her name!! Is this crazy or what!!???? Thought Jimmy.

There was no controlling Jimmy now or holding him back, the animal in him had taken over. He pulled his cock out, stuck 3 fingers into Ellen's pussy and smeared cum and pre-cum over the tight entrance to her ass. He then pressed his rock hard cock against her tight little asshole. The sphincter tightened as Ellen began to realize what was happening. Jimmy wasn't about to let that stop him, he pushed hard shoving half of his cock into her!! God it was tight, he thought and felt soooooooo goooooood!! Ellen screamed and too Jimmy's surprise Sarah grabbed her around the head and kissed her muffling the scream!!

Another push and Jimmy was in up to his balls!! He rested there not wanting to cum yet, Ellen stopped screaming, Sarah was now moving into a 69 position with Ellen and began to suck on her cunt enjoying the mixture of Jimmy's pre-cum and Ellen's cum!! She just couldn't get enough…the doors of eroticism had been opened by this young fucking stud and she was couldn't stop the carnal pleasure. Ellen, was sooooo confused, her asshole was on fire, her pussy was so sensitive that she was, it seemed, having one HUGE CONTINUOUS orgasm. Her nipples were hard and now Jimmy was beginning to move in and out of her ass in a very slow manner. Time had stopped for her and she couldn't think clearly…only act!!

Dropping her head she saw Sarah's wet pussy below and without thinking she dropped her head down and began to suck on her clit. Sarah's pussy was warm, quite moist (tasted of cum) and smelled of sex!! There's a certain smell to good sex. A smell that once you've experienced it… you'll never forget!! Yes there's a taste to it as well, but the smell sticks with you. If you ever walked into a room where sex has recently taken place…you know what I mean. If you've ever been close to a woman or man who, for the lack of a better saying "is in a sexual mode" where they give off a sexual air, then you know what I mean. It was then that Ellen had the most fantastic orgasm of her life. How could this young insolent bastard give her the orgasm of her life…it was a mixture of pleasure and frustration rolled into one.

Sarah looked up and saw Jimmy's nuts hanging, moving back and forth with his stride, slapping against Ellen's cheeks as Ellen's cum was dripping into Sarah's face. She had remembered seeing her father's nuts once when she was a little girl. She, quite innocently walked into her parents bedroom and her father was asleep with the covers pushed to the side. She remembered being fascinated by the size of her father's "member" as she use to call it and how intrigued she was by the two large eggs that his member rested on. She wanted to go closer and touch it, but didn't dare. There wasn't anything sexual about the viewing…just curiosity!!

As she walked closer, on tip toes to make sure he didn't wake him she noticed his member was large with a slightly purple knob and the knob had a tiny hole in it. Strange… she thought at the time, she had heard, little girls talk, about a man's member seemed a beautiful thing. So filled with a desire to touch it she finally reached out and softly place her hand on it. Running her fingers down the length to the knob. It was soft but firm and smooth….she heard her father make a noise…almost a moan and she quickly ran from the room afraid she had awakened him!! She reached up and cupped Jimmy's nuts in her left hand. Sarah, was close to climax.

She briefly messaged them, then removed her mouth from Ellen's cum soaked cunt and took Jimmy's balls into her mouth. It wasn't easy, his movement was getting faster and faster but as soon as Jimmy felt her mouth on his nuts he slowed down. She sucked first one then the other, Jimmy could hold on no longer…he cam with such a force that it filled Ellen's virgin ass with warm semi white liquid!! Spurt after spurt gushed into her and Jimmy was so overcome he started slapping Ellen on the ass and crying out….HOW WAS THAT BITCH???? WAS MY COCK BIG ENOUGH FOR YOU?? His cock popped out of Ellen's ass followed by gobs of cum which slid down Jimmy's shrinking cock and onto Sarah's face…Sarah cam at that moment!!

Canoe
Canoe
35 Followers
12