Jimmy's Plan Ch. 8

Mary, Jimmy's bother's girlfriend caught Jimmy and his Mother Sylvia having sex. She demanded that Sylvia have sex with her brother in turn for Mary's silence. Mary arranged for a Motel and it is here that the story picks up...

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Terry looked at his sister Mary as they drove to the Twilight Motel. He couldn't believe what was going on. His sister had somehow persuaded an older woman, Mary didn't say how old, to have sex with him as his belated birthday present!!! Was life great or what! Terry was very fond of Mary. She always had time for him, talked to him more as an equal even though she was his stepsister. She was a little shorter; he was 5' 4", rather short for his age. He had the physique of a non-athlete, a little on the chunky side but not really fat. He came in at about 165 pounds. He looked a little like his stepsister from an appearance standpoint.

If you didn't know, you would have thought them to be blood relatives. Both had dark hair, same eyes, were close to the same height and for a boy, well lets just say he was almost cute!! Terry however was a little slow and had held back a grade on two occasions in High School. As a result he was still a Junior with two years to go to graduation. Terry never really noticed the difference between himself and his classmates but they did tease him a bit. Some of the girls felt sorry for him and through that sympathy is how he gained the little experience he had had. It was because of this that Mary had decided on the birthday gift she did for him. What turned out to be uncanny luck was her catching Jimmy and his mother Sylvia in the act!! She couldn't have planned this better…even if she had planned it!!!

He couldn't help but check out her body as they drove. She Mary could feel his eyes on her and looked over catching him staring at her legs. She had on a little mini-skirt that with the driving had ridden up to the point where he could almost see her panties. "Settle down Tiger!" Mary said "You'll get yours soon!" and laughed out loud!! Terry was a little embarrassed, he had never been with a woman and he had never really thought of his sister sexually until that very minute. It must have been prompted by what he knew was going to happen!! He just moved his eyes front and smiled!

Pulling up to the Motel Mary swung the car around to the stairway leading to room 207. Turning to her brother she said, "Remember, no names, she is to stay with you until midnight! I will come back around 1:00AM to pick you up. Any questions?" Terry shook his head, no and placed a nervous hand on the car door, opened it and stepped into the parking lot. He bent over and looked back into the car and said "than you" to his sister and used the opportunity to take another look at her legs. From this vantage point he could see her panties. Looking up from her panty covered pussy he looked at Mary, gave a quiet wolf whistle and said "Red eh??" Mary laughed and said "Get the hell out of here!! What kind of a little pervert have I created?" Shutting the car door Terry climbed the steps to room 207. Mary on the other hand, as she drove off, was left with the knowledge that having her brother stare at her turned her on!!!

Once at the door Terry knocked lightly. There was no response, no noise from inside. Did he have the right room?? Like any nervous kid about to do something clandestine, fear started to surround him. He knocked again, this time a little louder. This time he heard shuffling inside the room, the doorknob turned, the door opened and there stood Sylvia. "Come in…Terry? Is that right?" she said. Terry was a little disappointed, this woman was a lot older than he had expected and quite frankly a lot heaver than he had imagined!! Terry nodded and said "Yes Ma'am!" He stepped inside and closed the door behind him. Sylvia stepped by him and locked the door. "My Sister said you were going to teach me about sex!!" is all that Terry could blurt out!! Sylvia was a little taken back by the directness of such a youngster but recovered and said, "That's why we are here." Mary kept thinking to herself, "Where do I start??"

Thinking she would try and break the ice a little she walked over to the bed and laid down propping her back against the headboard. With her foot she motioned for Terry to take a seat at the foot of the bed. From this position Terry could see about midway up her thigh and his early disappointment was now turning to lust!! Lust that only a virgin can feel!

Mary began a series of questions she thought would help her determine what he knew already.

"Have you ever had sex before?"

"No Ma'am" Terry was embarrassed with his lack of experience.

"What have you done?" "I have played with some girls tits!" he said proudly. "But I haven't had many dates," Terry sheepishly proclaimed.

Sylvia was gaining confidence. She could see why he did get many dates, short, over weight and not particularly social; yet she thought he was kind of cute. Not a bad kid…but still a kid!! She had to get by this. If she didn't do what she was told she knew that Mary would spread her terrible secret and her life would be ruined. Might as well get on with it. Try and relax she told herself, just try and relax!!

"Do you like playing with tits, Terry?"

"Yes, very much!!"

"Would you like to play with my tits?" Sylvia surprised herself with the directness of her own question.

Terry smiled and nodded his head enthusiastically!! "Yes!!" he said trying to contain his excitement!

Patting the bed next to her she motioned for him to move up, which he eagerly did! She whispered to Terry, "Unbutton the front of my dress." With nervous hands Terry immediately reached for the buttons on the front of Sylvia's dress. As calmly as he could he began to unbutton the front. First, one button, then another, until he had unbuttoned her dress to the waist. With shaking hands he pushed the dress off her shoulders and down her arms. Terry couldn't believe the size of her tits!! He had played with the tits of girls his own age but they were nothing like this. Her tits were struggling against her bra desperately trying to be release. Terry seems transfixed, not moving so Sylvia told him, "Now push the straps down." Immediately, being given permission, Terry reached up and pushed the straps down over her shoulders and pulled the cups of her bra down. Her tits gave way with a burst, almost saying thank you!!! Again Terry sat motionless.

Sylvia took his left hand and placed it on her right boob and encouraged a squeezing motion. Terry could feel his cock fully erect by this time pushing hard against his jeans!! This did not go unnoticed to Sylvia; she could see the bulge and knew he wanted the tightness to go away. Closing her eyes Sylvia, against her own better judgment, began to enjoy the gentle movement. He moved his hand to her nipple and gently squeezed that as well. This sent a flash of pleasure to Sylvia's loins!! "Now with your other hand." She didn't need to finish the sentence; Terry placed his right hand on her left tit. Terry was a quick study, it didn't take long and he was into the action. Smoothing, stroking, squeezing and pinching Sylvia's tits and nipples. Sylvia, with eyes still closed, opened her mouth slightly and a low moan escaped!! Terry thought, "Can I really be pleasing this older woman??"

After about 15 minutes of letting Terry crudely message her, Sylvia opened her eyes and said, "Have you ever touched a woman's vagina?" Terry shook his head no and cast his eyes down. Sylvia removed his right hand from her left tit and moved it to her dress covered pussy. Terry, not sure what to do began to message through the cloth. Sylvia thought, "For Christ's sake what do I have to do?? Lead him to every move??"

It was then that Terry began to gain some courage. He moved his right hand to Sylvia's knee and slid it under her dress; slowly moving it passed the tops of her nylons, to that super sensitive stretch of skin between the tops of her nylons and her panties. Sylvia's breath began to quicken and she found herself trying to move her hips toward his hand as moved upward!! Terry touched her panty covered pussy. It was like a jolt of electricity for both Terry and Sylvia. Forcing his fingers up the inside of her thigh he found the elastic edge of her panties and pushed the fabric aside as his fingers found her now wet pussy. Sylvia sucked in her breath, moving her hips to meet the thrust of his fingers, which were not rubbing the lips of her pussy and slowly forcing their way inside her warm, wet and willing cunt!

Sylvia could no longer contain herself. She reached out and placed her hand on Terry's swollen crotch!! Terry almost came with the touch, even though it was on his jeans. Sylvia searched with her hand and found the button to his jeans; UN did it and pulled his zipper down. Sticking her hand inside his boxer shorts she had to contain her surprise!! Terry wasn't big, as a matter of fact he was rather short, 4" would be Sylvia's guess…but his circumference was huge!! He was at least 3" in diameter. His cock damn near fit into her small hand but she could only get her fingers half way around it. She noticed she covered part of his pee-hole as she held him.!! "This is really odd!" she thought.

Terry was in an extremely joyful state. He had played with girls his own age but none of them had actually touched his cock!!! He couldn't believe how good her hand felt!! Sylvia stroked his short and swollen member up and down about 3 times when it happened. Being with an older woman, in a hotel room, playing with her tits and having his fingers in her wet pussy was more than he could take. Much to his embarrassment he shot his load straight into the air or at least sort of straight in the air. You see, his first shot came on the upstroke and Sylvia hand was partially covering his cum exit!! The result was almost comical; semen went in all directions, splattering both Terry and Sylvia. Subsequent shots went off in the same generally erratic direction. Sylvia continued to work her hand up and down milking his tree truck until it was dry!!

Terry was beet red and Sylvia thought he looked so cute she couldn't help but kiss him first on the forehead, then his nose and then what she thought would be a light peck on his lips. His lips were so soft and tentative Sylvia was forced to linger for a moment. That moment was long enough for Terry to return the kiss. He did it more out of a need for reassurance than passion. He wanted to be reassured that everything was okay. Sylvia opened her mouth slightly and allowed her tongue to apply a slight pressure to his lips. Terry was no novice to kissing. He had French kissed several of the "prick teasing" girls in his High School. To Sylvia's surprise before she could react Jimmy had opened his mouth and was sucking on her tongue. "God this feels good," thought Sylvia and she gave out a slight whimper. Hearing this, Terry moved his hand to her breast and began to squeeze and pinch it causing Sylvia, who was still hot, to groan louder!! To her total surprise she was actually enjoying herself!!

Terry once again placed his other hand on Sylvia's thigh and moved it up until he touched her now soaking wet pussy. Again he pushed aside the fabric of her panties and pushed two fingers into her warm receptive love canal. Sylvia was in a continuous moan mode now, " aaaaaahhhh, oooohhhhh, yes there, no a little left, not so hard there, no harder there, yessss, yesss, that's right, oooohhhh!!!" Terry was proud of himself; he had this older woman moaning with pleasure!! His cock, though never having gone completely soft was now hard as a rock!!! Sylvia grabbed Terry by the back of his neck and drew his head to her breast smashing Terry's mouth against her erect nipple. Terry opened his mouth and began to suck!! "Not too hard, there, good, now bite lightly!!" directed Sylvia. The moaning continued! Working his hand in her pussy Sylvia took hold of Terry's wrist and guided his hand in and out then she pulled his hand nearly out and pushed it up and against her clit. When the back of his middle finger touched her clit Sylvia jerked like she had been hit with an electric shock!! She squeezed her thighs around his hand hoping he would never stop!! Terry had his left hand on Sylvia's back; moving his head to her left breast first he licked then began sucking her left nipple. With his left hand he messaged her right nipple. With both tits being manipulated, much to her pleasure and Terry's other hand messaging her clit…. Mary had her first orgasm of the evening!! It shook her deep down and she clamped down hard on Terry's hand with her thighs while simultaneously crushing his head against her breast!! The reality of what had happened hit her, she couldn't deny it, and it was a great orgasm!! How could this happen with this little guy!

Terry, for the first time in his life felt a woman's orgasm. He felt her vaginal walls pulsate and her cum moisten his fingers. His cock was harder than it had ever been before!! He was at that point of confusion that only sexual frustration can put you in. He knew he wanted, no must do something but his lack of experience confused him and left him nervous and fidgety!!

Sylvia slowly came back to reality and could feel Terry's frustration!! She immediately stood, raised her dress and removed her panties. Holding the dress around her waist she laid down on the bed. What a picture she made, the top of her dress was down around her waist leaving her well endowed tits exposed and the bottom of her dress was up around her waist leaving her ample ass and gapping pussy open to view. Believe me, Terry didn't miss a thing!! Sylvia instructed him to remove his pants and shorts, which he did and told him to move onto the bed, kneeling between her how spread legs. Terry may have been inexperienced but he knew what to do now!! He lowered himself down against Sylvia and tried unsuccessfully to place his cock in her pussy!! After a couple of tries, Sylvia reached down and guided his short fat member into her awaiting moist canal. Terry was more excited than ever; he felt first the head and then the entire length, force it way into her. He may have been short but girth made up for it. Even though Sylvia was wet, it took her a moment to adjust to his circumference. Terry, ever the eager one immediately began to fuck Sylvia as fast as he could. Realizing that he would last long like this Sylvia reached out and grabbed him by the cheeks of his ass and stopped his motion!! Forcing her legs together she was able to hold him still. "Slow down" she whispered we have plenty of time. "Just take it easy!!" "That was all well and good for Sylvia to say," thought Terry "but this was his first piece of ass, the first time he had ever had his cock in a pussy, it was the first time and it was this older woman who was being so kind, so pleasing…." He couldn't hold back any longer, he shot his sperm into Sylvia. Sylvia could feel his hips jerk and could feel his member expand and contract with each spurt of cum he deposited inside her!! Needless to say she was disappointed it ended so soon!!

Temporarily spent, Terry collapsed on Sylvia. He was sure he was in love with this wonder woman that was teaching him how beautiful life was. He had never before felt as happy and contented as he did at this moment!! Lying there Sylvia began to slowly rub his back with both her hands. His head rested on her shoulder and she rubbed the back of his neck as well. She was surprised by the fact that Terry's cock did not shrink!! It was just as rock hard as when they had started!! Holding him tightly she rolled over so he was now under her. She pushed off the bed and was now sitting on his cock. She began to move her hips ever so slightly in a circular motion. Terry could feel the inside of her pussy messaging him. He started to rise but Sylvia held him down saying "You keep still and let me do the work this time!" "Work" thought Terry "If this is work I never want to stop working!!!" Sylvia continued her slow circular motion and could feel her clit rubbing against his pubic bone!! "Good God" she thought, "This is one of the most enjoyable sexual experiences of her life!!" "How could this be, How can this be??" Sylvia took his through a dozen emotions over the next 20 minutes. She would lean down and drag her large tits across his chest, his face and encourage him to suck on her nipple or kiss the cleavage between her tits. At times she would stop, and give him a long lingering kiss forcing her tongue deep into his mouth. At other times she would bend over and kiss his nipples, message them with her wet tongue and nibble on them with her teeth. The entire time Terry was forced to remain lying down letting Sylvia instruct him in the finer points of love making!!

Sylvia could no longer maintain the slow rhythm, a fire was building in her loins and she needed to satisfy it. She began to rise up and down ever so slightly. With his shortness of length if she went too far he would pop out! She leaned forward pushing her tit into his eagerly receptive mouth and started an up/down grinding motion. This hit her clit with a full stroke on every movement. A now perspiring Sylvia started moaning…"Ooohhh! Aaaahhh! Yessss! Okay that's good, Ohhh so is that, Yes there, OOOOHHHHH!!"

She could no longer control herself. Terry was fighting just to hang on!! He too was about to have another orgasm (as only an 18 year old can) and he raised his hips to meet her grinding motion. Sylvia was screaming now, "OOOHH Fuck, OOOHH FUCK! THERE…THERE… NOWWWW!! YESSSSS, OOOOHHH FUCK, NOW!!!!!!!!!!!!!!!!!" Sylvia had the most satisfying orgasm of her life!! There was something unique about this sexual encounter that turned her on!! Maybe it was being the teacher; maybe it was the idea of such a young man and the feeling that she was actually helping him. She didn't know all she knew was "THIS IS HEAVEN!!!" Terry on the other hand was bewildered. He just had the second orgasm of his life inside a vagina!! He had to hold on for dear life to keep his stout tool engulfed in her raging pussy. He watched an older woman go crazy on top of him, felt her grind into his manhood, seen large tits swing frantically up and down and side to side, experienced pleasure he had never conceived possible and was now struggling to breath because Sylvia had collapsed on top of him covering his face with her left tit!!! He knew he had said it before but "Does life get any better than this????" He thought not!!!!

After what seemed like forever to Terry and was really maybe 5 minutes; Sylvia stirred and lifted herself off his face. He took a deep breath, thankful for the air!! Sylvia looked down at him with a puzzled grin. She didn't understand it, but she knew she enjoyed the pleasure of this!! Man did she enjoy it!! Reaching down she gave him a kiss on the lips and said, "Come on Terry we have to clean up!!" With that she slid off Terry's now deflated member and stood next to the bed allowing her dress to fall covering her swollen lipped love canal.

Sylvia, during the short walk to the bathroom realized that for some strange reason she was a changed woman. She took Terry's hand and led him to the bathroom. Sitting him on the stool she removed his socks and shirt and started the filling the tub with warm water. While the tub filled she step out of the bathroom and removed her dress, hanging it in the closet and returned to the bathroom naked!! This was part of the change that had somehow taken place. When she was with her son, Jimmy, she would not allow him to see her without her clothes on but with Terry she felt totally comfortable!! Who'd-a-thought!! Pulling Terry off the stool she wrapped her arms around him and gave him a big hug!! Their bodies fit well together even though she was about 4" taller. Tummy to tummy, hip to hip they met perfectly. As she held the embrace she could feel Terry's cock begin to move. She playfully leaned back forcing her hips hard against him and smiled saying, "We better get in the tub before the water gets cold." She released him and shut the water off; stepped into the tub and sat down. Reaching out her arms she invited Terry to join her. She didn't have to ask twice.