Summer of '59
INTRODUCTION
Cliff Jennings graduated from high school in June 1959 and he had just celebrated his 18th birthday on June 25th. Cliff would be attending the local community college in the fall and he planned to work during the summer so that he had money for college. Most of Cliff's friends, boys and girls, were going away to college. In fact some of the girls looked down their nose at anyone who was not going to one of the bigger universities or private colleges. Cliff didn't let that bother him as he was self assured and confident that he would be successful.
Cliff was a good looking young man. He stood at 6'2" and weighed a muscular 185. His hair was light brown and he had steel blue eyes. He had played varsity sports in high school and his body was chiseled. Cliff was experienced with girls as he had had sex with a couple of them although he found most of them to be teases and a pain in the ass. The girls he did fuck liked his 7+ inch cock. It wasn't huge by any means but clearly above average and it turned some of the girls on.
He had applied for a summer job with a company that installed and maintained swimming pools. However as he was waiting to hear back from them he decided to take on small jobs and projects. He would cut lawns, paint or any type of project where someone needed help. He ran one ad in the local paper and he immediately landed some odd jobs. One of those jobs was working for a woman on Saturdays.
Peggy Marshall was a divorcee of six years now. At the age of 36 years she was still an attractive woman with a nice figure. Her breasts were never large but she was proud of her firm 34B bust. She had a narrow waist of 23 inches and hips of 36 inches. She had a really nice ass that was very sensitive and she loved to have men play with her bottom and even spank her occasionally. Peggy had shoulder length brown hair and matching brown eyes. She stood at 5'5" tall and weighed a very fit 115 pounds.
Peggy had dated the past five years since her divorce. She never had trouble attracting men but she had trouble keeping them. Her somewhat kinky behavior always chased them away after several dates. She didn't get discouraged though and she kept dating and trying to find the right man for her. She had seen the ad in the paper that Cliff had submitted and she called him to see if he would be willing to help her with odd jobs around the house. Cliff immediately accepted and he was starting the next Saturday.
CLIFF'S FIRST ODD JOB
Cliff arrived at the small but quaint home of Peggy Marshall and after the introductions she showed him around the house and what she had in mind. Peggy was taken with the handsome young man as she had not expected someone so attractive. Cliff had never even thought about sex with an older woman and it wasn't on his mind when he met Peggy either. That day she was dressed in a summer smock that came down below her knees almost to her ankles. It was not a flattering dress and it did not reveal Peggy's charms that were under it.
Peggy insisted that Cliff call her by her first name as Mrs. Marshall sounded old. She showed Cliff the attic where they would start their projects. Peggy wanted to clean out the attic and assess her belongings. Some things would be salvaged, some donated and others just tossed in the garbage. Cliff would haul the stuff down out of the attic into the garage where Peggy would sort it out into the three categories. They worked all morning and then Peggy offered to make some lunch.
She and Cliff sat on the patio and had a sandwich and a glass of lemonade. They chatted a little but it was mostly Peggy asking Cliff about his future plans. She told him that she was pleased that he was going to college locally and that if she needed his help in the future he would be around town. They finished lunch and then went back to work. Cliff brought a few more things down from the attic and Peggy put them on shelves in the garage.
Peggy was standing on a six foot ladder when she asked Cliff to hand her some of the smaller items so she could put them on the top shelf. Cliff handed her an item and then stood by the ladder. As Peggy stretched to place the item on the shelf her smock rode up on her legs baring her shapely calf. Cliff looked at her bare skin and suddenly felt a surge in his loins. He stepped in a little closer and peeked under her skirt. He saw more leg this time up to her thighs and he felt an erection form in his pants. Then he acted as if he were holding the ladder and leaned in even more. This time as he looked up her dress he could see all the way to her panties.
Peggy turned to him and asked for another item and Cliff had to move carefully as his cock was hard and pressing against the leg of his pants. Peggy didn't notice his hard-on at the time but she was somewhat suspicious that Cliff had been looking up her dress. She was a little turned on that a young man would be interested in looking up her dress. This time when she took the item from Cliff, she asked him to hold the ladder and then she stepped up one more rung. Cliff leaned in and peeked up her dress and he easily saw her legs and panties. He noticed her nice round ass encased by the panties and his cock throbbed in his pants. This time when Peggy turned back to him she saw the outline of the erection in his pants. She smiled to herself as she was pleased that she could cause this young man to get an erection. This game continued for quite some time before Peggy pushed it to the next level.
"Oh my I am so sorry! Look what I have done to you," Peggy said as she made her descent down the ladder.
Cliff looked confused but then he realized she was talking about his erection which was clearly visible in his pants.
"I am so naughty letting you look up my dress. Only bad girls do that and they get punished when they do such things. I made your thing hard because I was so naughty," Peggy went on.
Cliff thought that this was really weird behavior especially for an older woman to be talking like that. He wondered, "What did she mean when she said she should be punished for her behavior."
"If my daddy was here he would spank my bottom for being so naughty," Peggy whimpered and then said, "You're not going to spank me, are you?"
Cliff realized that this was a game she played and he decided to go along and see how far it would go. He was getting really excited now and his cock was throbbing in his pants. He replied, "You have been a bad girl and I think that you do need a spanking."
"Oh no, please don't," she whimpered again and than ran into the house like a little girl running away from her punishment.
Cliff followed her into the house and found her in the living room. She was curled up on the sofa and acting as if she was afraid to be punished.
"Please don't, don't put me over your lap and spank me," she begged mockingly.
Cliff caught on that she was really giving him instructions rather than protesting. He moved over to the sofa and sat in the middle as Peggy cowered in the corner of the sofa. Cliff was starting to like this game and he reached for Peggy. He pulled her over his lap and her body pressed against his erection.
"Pleased don't flip my dress up and spank me," Peggy faked again but Cliff did just that.
He flipped her dress up baring her legs and her panty covered ass. Cliff stared at her beautiful shapely legs and curvy butt. He then realized just how pretty and shapely Peggy Marshall was. He ran his hands over her legs and panty covered ass and then he spanked her lightly on her bottom.
"Oh you mustn't take my panties down and spank me on my bare bottom," she said.
Again Cliff did just that. He pulled her panties down to her knees and then he admired her beautiful ass. He ran his hands over her smooth buns and squeezed them gently. His cock was ready to explode and he was fearful that he would cum in his pants if this went on much longer. Cliff began to spank Peggy's bare ass lightly and he liked watching her buttocks jiggle each time he slapped them. Peggy made believe that she was in agony and she began to beg Cliff to stop. Although he had not slapped her ass hard enough to hurt her it was all part of her game.
"Oh please stop your hurting me. Please don't hit me anymore I will do what you want. I will let you put your thing in my mouth," Peggy pleaded.
Cliff was in disbelief when he heard her. She wanted his cock in her mouth. She was going to blow him. Cliff couldn't move fast enough. He lifted Peggy off his lap and reached for his belt and zipper. He pulled his pants down to his knees and his rock hard 7+ inches bobbed in front of him. Peggy smiled when she saw the impressive cock and she knelt in front of him. Cliff grabbed her head and pulled it toward his cock. Peggy willingly took the cock into her mouth and within seconds she was deep throating him. No girl Cliff had ever been with ever took his entire length into her mouth but Peggy was handling his cock with ease.
Peggy was an accomplished cock sucker and Cliff knew that he would not last long at all. She bobbed her head up and down on his cock and ran her tongue around the shaft. She reached down and handled his balls and tickled his perineum. She had Cliff on the verge of one of his biggest ejaculations ever. He could feel the pressure in his scrotum and then it released through his cock. Cliff fired a barrage of cum into Peggy's mouth and he marveled at her as she stayed with it and swallowed every drop. He knew it was one of his biggest discharges ever but Peggy seemed undaunted by it as she sucked and milked his cock dry. She nibbled on his cock head and let it pop out of her mouth with a loud sound. She continued this until Cliff couldn't stand the sensation any longer. He was still hard however and Peggy wanted that youthful cock in her pussy.
"Oh look what you've done. You shot your stuff in my mouth. Now behave yourself and go away. Don't even think of putting your thing in my little cunny," Peggy acted out her shame.
But Cliff knew that they weren't done and he pushed Peggy back on the floor and crawled between her legs. He was surprised to see her pussy so well trimmed as he always thought that older women had hairy pussies. He eased his cock into her and it slipped in easily as Peggy's cunt was sopping wet. Peggy gasped as his cock hit home and she wrapped her legs around Cliff's torso. Cliff pounded her pussy with his rock hard cock and Peggy grunted and groaned every time his cock went all the way into her womb.
"Oh my, this is going to be a quick one!" Peggy gasped.
Her body lifted off the floor with the intensity of her first orgasm. She held Cliff tight as her body shook violently and he felt her juices cover his cock. Cliff's pecker was swimming in Peggy's pussy but he continued to pound at her in search of his second ejaculation. Peggy was extremely turned on and she felt another orgasm building in her body as Cliff raced toward his. She felt his body tense up and then with one more thrust deep into her, Cliff shot streams of cum into her hot cunt. Peggy felt the ejaculation and it sent her over the edge again. She dug her heels into Cliff's back and held him tightly in her arms as she climaxed again. Her body shook and she screamed out in ecstasy as she had one of her most intense orgasms ever.
The two of them held to each other and remained motionless on the floor for several minutes. Cliff thought about his situation as they both remained coupled together still partially clothed. Peggy had not removed her dress only her panties and Cliff still had his pants and underwear between his knees and ankles. Cliff eased his cock out of Peggy's cunt and he looked down at the pretty woman. She smiled at him briefly and then went back to playing her games.
"Oh what have we done? I am so ashamed," Peggy said and then picked up her panties and ran to her bathroom.
Cliff was unsure of what to do so he pulled up his underwear and pants. He straightened himself up the best he could although he could still feel the moisture from their lovemaking on his cock. It didn't appear that Peggy was coming out of the bathroom anytime soon so Cliff decided to leave. As he drove home that afternoon he thought about what happened. He was really turned on by Peggy's behavior and it had gotten him very excited.
Peggy came out of the bathroom after Cliff left and she was mad at herself for pushing the game too far. She had hoped he would still be there as she wanted to have more sex with him. She hoped that she hadn't scared him away. He had such a nice cock and she knew that he probably could have cum at least two more times that day. The next time she would have to be careful not to chase him away too soon. That was the problem Peggy had with men. They thought that she was too kinky and she scared them away.
That night Cliff lay in his bed and thought of Peggy. He hoped that she would hire him again so that he could see her again. He thought of her oral skills and the way they fucked. Cliff got an erection reflecting on the afternoon sex and he jerked off thinking of Peggy. He wished he had stayed and fucked her some more but now it was just a memory. Cliff jerked his cock faster as he approached his release and then cum shot out of his cock and landed on his chest, abs and pubes. He later fell asleep letting cum dry on his body.
PEGGY CALLS AGAIN
The next day the phone rang and Cliff's mother answered it. She handed him the phone and it was Peggy on the line. She asked if he could come over that day and help her finish up the project they started yesterday. Cliff had a quick breakfast and he was on his way to Peggy's house. When he arrived she was dressed the same was as the previous day. They worked on the attic some more and then moved back into the garage. The same pattern developed with Cliff handing items to Peggy to place on the shelf as she stood on the ladder. Cliff used every opportunity to look up her skirt and this time she was not wearing panties. Peggy then began her game again.
"Are you looking up my skirt again? I shouldn't let you look up my skirt. My daddy says not to let boys look up my skirt because they will want to put their mouth on my cunny," Peggy play acted.
"You're not wearing any panties Peggy," Cliff said going along with her.
"All my panties are soiled and I didn't have a clean pair to put on. But you shouldn't be looking up my skirt either. You wouldn't know that I didn't have panties on if you didn't look up my skirt," Peggy said acting shyly.
"But Peggy you let me look up your skirt and now you should be punished," Cliff replied.
"Oh please don't spank me again and don't even think that you can put your mouth on my cunny," Peggy whimpered.
Cliff realized that she wanted him to eat her pussy first that day. He had eaten pussy before but only twice. Cliff ran his hands up Peggy's legs and cupped her buttocks pulling her down to his head level. He pushed up her skirt and began eating her pussy while she stood on the ladder. Peggy grabbed his head and held it tightly to her quim as Cliff dipped his tongue into her and sought out her clit. Peggy was overwhelmed with desire and she came quickly dousing Cliff's face with her female nectar. Cliff kept eating her until she couldn't stand it any longer and collapsed in his arms. He carried her into the house and into the bedroom.
Cliff placed her on the bed and then lowered his pants and underwear to his knees. He crawled on the bed, pushed her skirt up and moved between her legs. Cliff eased his cock into her sopping wet cunt again and Peggy gasped as she had the first time. They fucked like animals as they both raced toward their orgasms. Cliff was quick to fire and he let loose a barrage of cum into her pussy. Peggy came again as soon as she felt cum bounce of the walls of her vagina. They held each other tight as they rode out their intense orgasms.
Cliff then pulled out of her and placed Peggy over his lap. His pants and underwear were down around his ankles and he was still wearing his shirt. Peggy was still in her summer dress and Cliff pulled it up exposing her ass.
"You have been naughty again so I am going to give you a good spanking," Cliff teased as he ran his hands over her shapely ass.
Cliff spanked her again as he had done the previous day. He hit her lightly not to hurt her but hard enough to make her buttocks jiggle. He would pause every once in a while to run his hands over her shapely ass and then he would spank her again. Cliff felt his cock harden under Peggy's lap and she felt it too.
Peggy faked that she was crying and that her buns were stinging. "Daddy always put lotion on my bottom after he spanked me to soothe the pain."
Cliff looked around and spotted the lotion on her nightstand. He leaned over to retrieve it holding Peggy on his lap as he did. Cliff got the lotion and squirted it all over Peggy's ass. Cliff then massaged the lotion into Peggy's buttocks. He took his time as he loved handling her beautiful ass. Cliff's cock was erect under Peggy and she could feel it poking into her pubes.
"That feels so good on my sore bottom," cooed Peggy and then warned, "But you mustn't stick your finger in my pooper. That would be so nasty."
Cliff realized that she wanted him to finger her asshole. He had never done that before but the thought of it excited him. He squirted the lotion in the crack of her ass and then pushed his index finger into her asshole. Peggy wiggled her ass in reply and faked her response.
"Oh that is so nasty. You shouldn't do that. You shouldn't move your finger in and out of my pooper."
Cliff did just that as he finger fucked Peggy's asshole. Then he switched fingers from his index finger to his middle finger and pushed it in as far as it would go. Peggy wiggled her ass again and Cliff was getting hotter by the second. He decided that he wanted Peggy on all fours while he played with her ass and finger fucked her. He pushed Peggy off his lap and told her to get on all fours on the bed. Peggy did as she was told and she placed her head on the bed turned to one side as she raised her shapely ass in the air.
Cliff knelt behind her and pushed his middle finger back into her ass and resumed finger fucking her bung hole. He then switched back to his index finger but at the same time he slipped his middle finger and ring finger into her pussy. Now he sawed three fingers in and out of her as he fingered fucked her asshole and pussy at the same time. Peggy loved the feeling of the three fingers in her and she was pleased that Cliff had thought to do it but she wanted more.
"Your fingers feel wonderfully nasty in my cunny and pooper but you can't put your thing in my pooper. That would be dirty and wicked," Peggy said sounding childish.
Cliff thought about her statement, "Gees, she asking me to fuck her in the ass."
Cliff had never fucked anyone in the ass before. He had heard in school that some of his friends had butt-fucked their girlfriends but he had never done that. Still the thought of the taboo act thrilled him and his cock was aching it was so hard. He took more lotion and put it on his cock and then added saliva to it making it nice and slick for Peggy's asshole. Cliff had used lotion and saliva at times when he masturbated so he knew how to make his cock slick. He them removed his fingers from her pussy and asshole and lined up his cock with her anus.
Cliff pushed his cock into her asshole and when the head cleared her sphincter Peggy let out an audible gasp. The feeling was incredible for Cliff as his rock hard cock nestled into Peggy's snug warm sheath. He pushed his cock in all the way and then pulled back so just the head remained in her ass. Cliff fucked her slowly as he wanted it to last forever. Peggy had her head turned to the side on the bed and she had a dreamy expression of her face. She was obviously enjoying the anal sex.
Cliff moved steadily and slowly in and out of Peggy's ass until he felt his release building in his balls. Cliff picked up the pace and thrust quicker and harder into Peggy's ass. His body slapped against her buttocks causing them to jiggle as he fucked her and the sight was erotic. He loved watching his cock slide in and out of her shapely buns. Then his body stiffened and he thrust all the way into her ass as his cum traveled from his scrotum through his cock and shot into Peggy's ass. Cliff felt stream after stream of cum shoot through his cock and go deep into Peggy's rectum. Peggy loved the feeling of cum coating her anal channel and filling her rectum. Cliff had shot an enormous amount of cum in her asshole and Peggy couldn't remember the last time she was so full.
Cliff stayed in her ass for minutes as Peggy used her talented anal muscles to milk his cock dry of any cum remaining in his shaft. Cliff's cock began to soften slightly and he let it slip from Peggy's asshole. He looked at her dilated anus and it looked vulnerable as a little bit of cum trickled out of it. Cliff was then shocked when Peggy spun around and took his semi-erect cock in her mouth and sucked it clean. He couldn't believe that she would take a cock right from her ass into her mouth but the act excited him.
"My poor cunny needs attention right now," Peggy pleaded.
Cliff realized that they were still dressed. Peggy still had her dress on and he still had on his shirt with his pants and underwear around his ankles. In all the time they had fucked and sucked they had never been completely naked. Cliff now wanted to be naked and he wanted to see the rest of Peggy's body. He still hadn't seen her tits yet.
"Peggy I want to see you naked. Let's take all our clothes off," Cliff ordered rather than requested.
"But what if someone comes in and catches us naked?" she whimpered as if a little girl.
"No one is coming in. Now do as you're told or I am going to spank your bottom and put my thing in your pooper again," Cliff replied playing the game.
Peggy acted shy as she stood up and removed her dress and bra. Cliff watched her as he took off his own clothes. Peggy had a great figure and her tits were perfect, not too big and nice and firm. Peggy lay back on the bed and she opened her legs for Cliff. He knew that she wanted him to eat her pussy again and he was only to glad to comply. He slipped between her legs and she cuddled his head in her hands and stroked his hair and he ate her pussy.
Cliff buried his tongue in Peggy's pussy shoving it in as if he was fucking her. Peggy loved the action as he nibbled on her clit while he fingered her pussy. Cliff was really getting into the action particularly because of the way he had Peggy squirming and tossing on the bed. Peggy moved her legs over Cliff's shoulders and pulled his head closer to her pussy. Cliff held on to Peggy's shapely buttocks and squeezed and fondled her firm ass cheeks as he ate her pussy.
"Oh, oh, yes oh, oh!" Peggy cried out.
Cliff continued to eat her pussy as he held her ass tightly in his hands. He then moved his hands up to her tits and found her hard nipples. Cliff massaged her boobs and twirled her nipples in his fingertips as he continued to munch on her pussy and clit. Peggy was tossing and thrusting her pussy into Cliff's face as she moaned and groaned in ecstasy. Cliff decided to play with her asshole again as he ate her pussy. He snuck one hand behind Peggy's bottom and toyed with her asshole tickling the tight nether hole.
"Oh are you going to put your finger in my pooper again?" Peggy sighed.
Cliff stuck his middle finger in Peggy's pussy and got it good and wet with her juices. He then positioned it at Peggy's asshole and shoved it in. Peggy gasped with the abrupt anal penetration but soon had Cliff's finger buried in her ass. Cliff pumped his finger in and out of Peggy's ass as he continued to maul her pussy with his mouth. Cliff loved the feel of his finger in the warm recess of Peggy's ass and he was sure that he could feel his cum in her hole.
Peggy stiffened and gasped aloud as she came on Cliff's face. Cliff held on to her with his finger still buried in her ass and his mouth glued to her cunt. He felt the waves of orgasm rock Peggy's body and his face was flooded with her cunt juice. Peggy kept humping his face until the last of her orgasms passed and she flopped back on the bed. Cliff slipped his finger from her ass and his hands found her breasts again. He stroked her tits and nipples as he gently licked her pussy dry of all her juices. Cliff finished eating her and then sat up kneeling between Peggy legs. Cliff followed Peggy's eyes to his cock and then he realized that he was hard again.
Peggy smiled at him and said, "Oh look at you. Your thing is big and hard again. Are you going to put your thing in my cunny again?"
Cliff leaned forward and aimed his cock at Peggy's pussy. He slid in easily to the hilt and reveled in the warmth of her cunt. Cliff began to pump his cock in and out of Peggy's pussy as she wrapped her shapely legs around his back. Peggy pulled him in with her legs and positioned herself so that her clit was in constant contact with his cock. Cliff began to pound Peggy's pussy and Peggy humped her hips back at him just as hard. The two of them fucked each other frantically breathing heavy and grunting and moaning. Peggy had another orgasm but continued to fuck Cliff toward his. Peggy lost count of her orgasms before Cliff finally filled her pussy with cum.
Cliff stiffened and then thrust into her each time he felt his cum ejaculate. Peggy rocked with him and she clenched her cunt muscles squeezing every drop of cum from his cock. Cliff collapsed on her body as he felt the last surge of cum leave his cock. Peggy held him tight as he relaxed his body. Cliff had never felt so good in his life. He had fucked other girls his age before but it was never like this. He couldn't believe his good fortune in fucking a woman like Peggy. It would change his opinion of older women forever.
Cliff and Peggy lay still in bed for a long time. Cliff caressed Peggy's cute firm tits and rolled her hard nipples in his fingers. Peggy ran her hand along Cliff's balls and cock and she soon had him hard again. Cliff rolled over on her and they fucked again until Peggy begged him to stop that she couldn't cum anymore.
"Oh please we have to give my poor cunny a rest," she pleaded.
"Okay then I will just have to stick my thing back in your pooper," Cliff replied playing her game.
Peggy rolled over and wiggled her ass for Cliff. He got some more lotion and lubed up his cock and her asshole once again. Then Cliff rolled over on top of Peggy and slid his cock into her ass once again. He fucked her slowly for awhile and then he knelt up pulling Peggy with him so he could watch the anal penetration. Cliff fucked her ass slowly for a long time before he came with his fourth load of the day. Cliff buried his cock in Peggy's ass and held it there as he ejaculated into her rectum. As before she used her anal muscles to milk his cock dry and then Cliff pulled his softening cock from her ass. He flopped down on the bed as he was drained and exhausted.
This time Peggy did not go down on him and take his cock in her mouth. She too lay still face down on the bed. Not another word was spoken as Cliff got up and went into the bathroom to clean up. He then dressed and went over to the side of the bed. He looked down at Peggy and stared at her gorgeous ass. It was hard for him to believe that he had fucked her ass not once but twice that day. He noticed that traces of cum seemed to bubble up and trickle out of her ass as she lay there. Cliff patted her on her shapely buttocks and said good-bye.
"I have some more work for you, are you available next weekend?" Peggy asked almost in a whisper.
"Yes I will keep the weekend open for you," Cliff replied and then he smiled to himself and thought, "This could be quite a summer."
Cliff left the house and then he drove back to his own home. He made himself something to eat and as his parents watched TV. Then he told them he was going up to his room as he was exhausted. They said goodnight and he went up to bed. He thought about Peggy and what next weekend would bring. Was it possible that they could do anything that they hadn't already done?
CLIFF LOOKS AT OLDER WOMEN IN A NEW WAY
Monday morning Cliff woke up and went downstairs to have breakfast. His parents had already left for work so he got a glass of juice and a bowl of cereal. After breakfast Cliff went outside to play basketball in the driveway. As he shot hoops in his driveway he spotted his neighbor and former classmate Steven Faulkner.
"Hey Steve, want to join me shooting hoops," Cliff called.
"No thanks, I'm going to clean the pool. Why don't you come over later for a swim," Steven offered.
"Sounds great, I'll be over later," Cliff accepted.
Cliff knew that Steven was a homosexual but he still liked him. Steven had never made a pass at Cliff and they got along fine as neighbors. Steven's parents were divorced and he lived with his mother in the house. Steven handled most of the chores and at times Cliff helped them out. Cliff had never paid much attention to Steven's mom, Clara Faulkner. But all of a sudden he thought back to how she looked in a bathing suit. She always wore a very conservative one piece back bathing suit that had a little skirt on it. It seemed as if she were trying to conceal her curves. But Cliff remembered her great legs, her narrow waist and smallish bust when he saw her at the pool.
Probably because of his recent encounter with Peggy he wondered if Mrs. Faulkner was a good fuck or if she even got laid anymore. Cliff had never known her to date another man. Cliff decided to check with Steven later when they were at the pool together and find out if his mother was seeing anyone. Cliff realized that he was getting a hard on thinking about Mrs. Faulkner. Just then the phone rang and Cliff dashed inside to answer it.
The pool company was on the line and he had been selected for a summer job. He would not be put on the payroll but he would be paid by the job. It was explained that he knew anyone with swimming pools and he got a maintenance contract from them that he would receive a commission in addition to his hourly wage. Cliff was thrilled and his first job would be a week from Monday. Cliff hung up the phone and then he wrote down everyone he knew that had a swimming pool. He would contact them and see if they would be interested in a maintenance contract. He would start with the neighbors that afternoon when he spoke with Steven.
Later that day after lunch Cliff headed over to the Faulkner's back yard and entered the swimming pool area. They really had a nice setup. The pool wasn't huge but you could comfortably swim laps in it. There was a Jacuzzi at the far end that easily accommodated six people and the best thing was that the yard was totally secluded and private. Cliff spotted Steven in one of the lounges and called out to him.
"Hey Steven," Cliff yelled.
"Hi Cliff come on in. I just finished cleaning the pool and sat down to have a beer. Want one?" Steven offered.
"Sure a beer sounds good," Cliff accepted and sat in the lounge next to Steven.
Cliff told Steven about his new summer job with the pool company and that he started next Monday. Cliff also mentioned the opportunity to earn commissions on new business.
"Really that's cool," said Steven and then added, "We should look into having you do our maintenance."
"That would be great if you would check with your mom," Cliff replied.
"I think she might go for it. I'm leaving in two weeks for a skating camp and I will be gone for a little more than two weeks. My mom hates to clean the pool so it would be perfect if she hired you," Steven stated.
"Wow that would be great. As soon as I know how much it costs. I'll get the information to you," Cliff said excitedly.
"Hey let's go for a swim," Steven suggested.
Steven jumped in the water while Cliff was taking off his shorts. Cliff always wore shorts over his tight bikini Speedo. Steven also wore the same type of suit and they both displayed their manly packages. Steven watched as Cliff moved toward the pool and then dove in cutting the water like a knife. Steven felt his loins stir when he caught a glimpse of Cliff's cock outlined in the Speedo. Steven had never come on to Cliff but he secretly fantasized about sucking Cliff's cock and Cliff fucking him in the ass. Steven felt his own cock harden just at the thought of making it with Cliff. Steven snapped out of his day dream when Cliff surfaced and splashed water at Steven.
The two of them then swam around the pool for almost 30 minutes. Steven suggested the Jacuzzi, so they grabbed a couple of more beers and sat in the Jacuzzi. They stayed in the Jacuzzi until they finished their beers and then they jumped back in the pool to cool off for a few minutes. Steven and Cliff then got out and took their seats in the lounge chairs. They rested and chatted for several minutes when they were interrupted by Mrs. Faulkner who had just arrived home from work.
"Steven, I'm home," she called and then she spotted Cliff, "Oh hello Cliff how are you?"
"Just fine Mrs. Faulkner. How are you doing?" Cliff replied politely.
"I'm well thank you!" she answered blushing slightly because she caught herself looking at Cliff's crotch.
"Are you going to join us for a swim Mom?" Steven asked.
"Oh I don't think so. I was going to start dinner," she answered.
"Come on Mom, just for a little while. I'm not really that hungry yet," Steven urged.
"Yeah, come on Mrs. Faulkner please join us," Cliff asked chiming in as he wanted to see her in her bathing suit.
"Oh all right but just for a short while," she accepted.
"Hey Mom bring out some more beers when you come back," Steven called to her.
Several minutes later Clara Faulkner walked back into the pool area carrying a six pack of beer. Cliff studied her like he never had before and he decided that she was indeed a good looking woman. Cliff felt that familiar tingling in his loins and realized that he was getting an erection. Normally he would have been embarrassed and tried to hide it but today he was comfortable with the outline of his erect cock showing through his tight Speedo swimsuit.
Clara spotted Cliff's erection poking through his bathing suit and she felt a chill run through her body. Steven also noticed Cliff's boner and then he felt his own cock stiffen in his swimsuit. Cliff stared at Clara's shapely legs but he could only imagine what was underneath her bathing suit. The bathing suit was so conservative it was unflattering to her figure.
The talked for awhile as they sipped beers and Cliff brought up the pool maintenance issue with Clara. Steven though it was a great idea but Clara was cautious about it and said she wanted to hear how much it cost before she made any decisions. Cliff promised that he would get the information to her next week. Steven and Cliff finished the six pack of beer and then Clara decided it was time to make dinner. She said goodbye to Cliff and headed in the house. Cliff told Steven that he would see him tomorrow and then he went back to his home.
That night after dinner and leisure time, Steven, Clara and Cliff were in bed thinking about each other. Clara was thinking about Cliff, Cliff was thinking about Clara and Steven was thinking about Cliff. Cliff wished that Clara would wear a different bathing suit. A bikini would be ideal but even a two piece would be sufficient to show off her body. Cliff tried to picture her in a two piece bathing suit that showed off her shapely legs, her flat tummy and her curvy ass. He envisioned himself alone at the pool with Steven's mother rubbing suntan lotion on her back and shoulders as she lay face down.
Then Cliff imagined himself getting bolder and putting on her legs despite her mild protest. He let his hands slide inside her legs and Mrs. Faulkner opened them slightly. He then ran his hands over her shapely ass and tugged her bathing suit bottom down just below the cheeks of her ass. He then imagined that he massaged her curvy ass cheeks with his lotion slick hands. He would slip his fingers into the crack in her ass and between her legs locating her pussy. He imagined lifting Mrs. Faulkner up by her hips so that her ass was in the air and then he fingered her pussy and asshole at the same time just as he had done with Peggy.
By this time Cliff had a raging hard-on and he grabbed a hold of it. As he dreamed of the things that he would do with Mrs. Faulkner he jerked hard on his cock. His hand flew over his rod as he imagined fucking her in her pussy and in her ass. Cliff felt pressure in his balls and he knew he was seconds away from a massive ejaculation. He jerked faster and held his cock tighter until he felt the surge in his loins. Cum shot out of the end of his dick and hit the headboard and pillow. The second, third and forth jets landed on his chest as the fifth stream landed on his abs. His cock continued to spurt and cum puddled on his pubes. He released his cock and let it flop on his cum soaked pubes and he took a deep breath. Cliff lie still after his intense ejaculation and let his seed dry on his body. He hoped someday that Mrs. Faulkner would experience the intensity of his ejaculation.
In another bed Clara Faulkner was thinking of just that same thing. She often thought of Cliff and she always got excited when she saw the outline of his cock in his Speedo bathing suit. She knew it would never happen but she enjoyed fantasizing about Cliff making love to her. Clara had not had sex with a man since her husband passed away five years ago. At 42 years old she was still an attractive and fit woman but she purposely dressed conservatively so as not to draw attention to herself. She had dated a couple of times but they were all disasters since the guys wanted to fuck her on the first date. There were a couple of guys at the office who came on to her but they had reputations of bedding other girls in the office and they bragged about it. She had no interest in becoming another topic of conversation.
At 42 years of age Clara looked good. She was 5'5" tall, weighed 120 pounds and had a 33-24-34 figure. She kept herself well groomed and she liked keeping her pubic hair trimmed. Her legs looked good as did her breasts and her bottom. At that moment she laid in bed imagining that Cliff was in bed with her. He was naked next to her and he had pushed up her nightgown over her firm tits. Clara ran her hands over her breasts and tweaked her nipples imagining that it was Cliff doing it. Then she moved her hand down her body making believe that it was Cliff's. She tickled her vulva and then slipped a finger in her pussy. She sought out her clit and then pushed two more fingers into her pussy. Clara imagined Cliff rolling over on top of her and slipping his big cock into her. Her fingers worked her pussy frantically as she rushed toward her orgasm. Clara's body lifted off the bed and her hips gyrated as her fingers dug into her pussy. She had to muffle her scream with her free hand as her intense climax rocked her body. She humped her hand for several minutes and then flopped on the bed, her fingers drenched with her own love juices. Clara lay still as she recovered from of her most intense masturbation sessions ever. She removed her fingers and brought them to her nose. She was pleased with the way she smelt and she found herself wondering if Cliff ate pussy. Then she put the thought out of her mind as she knew she would never be in bed with her neighbor Cliff.
Down the hall a similar scene was played out as Steven fantasized about sucking Cliff's cock. He imagined Cliff big cock spurting in his mouth as he jerked on his own cock. Then Steven shoved a finger in his anus and tried to imagine Cliff fucking him in the ass. Steven jerked his cock rapidly as he fingered his ass and he was soon spurting cum all over his body. Steven then clamed after his ejaculation and lay still, his body cum covered. As his seed dried on is body, he thought about how he might be able to seduce Cliff. As thoughts raced through his mind he started to doze and then fell into a deep sleep. In the other rooms and beds Clara and Cliff also slept soundly.
PEGGY'S SURPRISE FOR CLIFF
The following Saturday Cliff arrived at Peggy's house to do some odd jobs and have some more sex with the kinky lady. He had been thinking about how to get Mrs. Faulkner in bed and as a result he was as horny as ever. Cliff rang the doorbell and waited for Peggy to answer the door. When the door opened Cliff was momentarily stunned as a girl with pig tails in a school uniform greeted him.
"Yes can I help you?" the girl asked.
Cliff then realized it was Peggy dressed in the school uniform. "Yes I'm here to help Mrs. Marshall with some chores." Cliff answered playing along.
"Oh you must be Cliff. My mother told me that you would be coming by today. She had to go out for awhile but she said that I should show you what to do. Please come in," Peggy play acted.
Cliff stepped in the house and he took a close look at Peggy. She really looked hot in the uniform. She had on saddle shoes with knee high white socks. The skirt was blue plaid that was so short that it barely covered her ass and panties. She also wore a white blouse with a blue string tie and a blue blazer. Cliff felt his loins surge again as he looked at the delectable Peggy.
"Come with me and I'll show you what has to be done in the basement," Peggy said and then led the way down to the basement.
Cliff watched her descend the stairs and he couldn't believe how much younger she looked dressed like this. He thought to himself this is one kinky lady. Peggy went about her play acting showing Cliff the boxes that had to be moved and as she bent over her short skirt rode up and provided a glimpse of her white cotton panties. Cliff felt his cock harden in his pants.
"And what is your name?" he asked almost laughing.
"My name is Peggy too. I am named after my mother," she said in a sultry tone.
"You can get started now and I will go and get us some lemonade," Peggy said.
Cliff watched as she walked back up the stairs and he could see under her skirt. Peggy's cotton covered curvy ass was visible under the skirt. He saw her luscious bare thighs between the white knee high socks and her cotton panties. Cliff waited for her to return with the lemonade and he watched as she descended the stairs.
Peggy blushed and then said, "Cliff I saw you looking under my skirt. That's not a nice thing to do. My mother told me that you might try to look under my skirt. Now please don't do that again and let' get to work."
Cliff just shrugged his shoulders and then they began to move some boxes. Cliff kept checking out Peggy's ass and then he couldn't resist any longer. When she bent over slightly he reached out and grabbed one ass cheek.
"Oh you naughty boy," she squealed.
Then Cliff pinched her bottom again and again until she jumped away from him. "Stop that this instant," Peggy said.
"My mother told me that you might try to put your hand under my skirt."
"Really and what else did she tell you?"
"She said that you might try to take my panties off to."
"And what else did she say?"
"She told me that you might try to put your mouth on my innocent little cunny."
"I see anything else?"
"And that you would try to put your finger in my cunny and in my pooper."
"Is that all?'
"No she said that you would try to put your thing in my mouth and my cunny and my pooper."
"Do you want me to do all those things to you?"
"Oh no I am a good girl. I could never do those things."
Cliff was now tired of playing the game without some action so he moved toward Peggy. She acted as if she tried to getaway but he caught her and forced her to her knees. Cliff pushed her over one of the boxes and then he flipped her skirt up over her back. He rubbed her hot ass through the cotton panties and then he pulled the panties down to her knees. He pushed his hand between her legs and located her sopping wet pussy. Peggy groaned as she felt the desired contact. Cliff fingered her pussy from behind and then he took a moistened finger and teased her anus with it.
"Oh no not in my pooper, I have never had anything in there. Don't hurt me!" Peggy exclaimed.
Cliff moistened his finger some more with her pussy juice and pushed it into her asshole. He continued to moisten his finger with cunt juice and saliva as her finger fucked both her cunt and ass at the same time. Peggy groaned with the double penetration as she loved both holes being filled at the same time. Cliff looked at her with her skirt tossed over her back and he panties down around her knees and he thought how erotic she looked bent over the box while he fingered her.
Cliff then needed to free his cock so he unfastened his pants and shoved them and his underwear down to his knees. Then he moved in behind Peggy and slid his erect cock into her hot pussy. He continued to play with her ass and finger her asshole as he fucked her doggy-style. It didn't take long for Cliff to cum as he was horny when he arrived and the play acting was a real turn on. His body stiffened as he shot a barrage of cum deep into Peggy's womb. Peggy had a mild orgasm just as she felt the semen spray her insides. She loved the way he came there was always so mush of it.
Cliff eventually pulled out of her and looked at her shapely ass and luscious thighs. He rubbed his cock on her ass and trickles of remaining semen coated her curvy bottom. Peggy turned around and she looked at his semi-hard cock. She knew that he would be ready to go again in minutes but she wanted to play act some more.
"Oh what have you done? You put your thing in my cunny and your finger in my pooper. And you shot your stuff into my poor cunny. I am not going to take your thing in my mouth," Peggy said trying to sound upset.
"I think you are going to take my thing in your mouth and clean it off and get me nice and hard again. This time I will put it in your pooper," Cliff said firmly as he reached for Peggy.
He took hold of her pigtails and gently pulled her head toward his cock. Peggy acted as if she was being forced to suck his cock and that she had no choice. Her mouth engulfed his cock and with in seconds Cliff was receiving one of Peggy's signature blow jobs. "God she was good," he thought to himself.
Peggy's head bobbed up and down and her tongue swirled around his cock as he held on to her pigtails. Then he had another idea so he reclined on his back and had Peggy straddle him so they could eat each other. He pulled her panties off her legs so that she sit on his face. Peggy lowered her pussy to Cliff's mouth as she resumed sucking his cock. Cliff stroked her luscious thighs and caressed her curvy ass as he sucked on her clit. Peggy was going wild and she knew that she was close to a massive orgasm.
Peggy began throwing her hips violently as she reached her climax and Cliff held on to her curvy ass as he tried to keep his mouth fastened to her pussy. Her juices gushed into Cliff's mouth as she groaned on his cock. Peggy momentarily stopped sucking Cliff's cock until the intensity of her orgasm had passed. Minutes after her orgasm, she resumed sucking Cliff's cock and she stayed with it until he ejaculated in her mouth. His second load was almost as voluminous as his first and her mouth filled quickly with cum. Peggy swallowed every drop and continued to suck on Cliff's cock even after she had milked his cock dry.
Peggy loved sucking Cliff's cock and she knew that she could keep him hard given his youthful recuperative powers. Cliff lay still and enjoyed the feeling of his cock in her sensuous mouth. Cliff wanted to stay hard so he could take on Peggy's ass next and she was doing a good job on his cock. When Cliff felt he was ready he gently pulled Peggy by her pigtails and she reluctantly removed her mouth from his erect cock. Cliff moved Peggy back over to the boxes and had her lean over one of them as she had when he fucked her before.
Peggy had anticipated being butt fucked again and she had placed lotion in the basement before Cliff arrived that day. She handed it to Cliff as she knew he was going to fuck her in the ass next. Cliff smiled at her as he took the lotion and greased up his cock. Then he went to work on Peggy's ass and she couldn't resist playing the game some more.
"Don't you dare try to put your thing in my pooper? You have already done too many nasty things to me. My mother was right about you," she whimpered.
Cliff was getting a little tired of the game but he went along with her as he prepared to fuck her in the ass. He put an ample amount of lotion in her ass and fingered her ass and pussy at the same time which they both loved. Cliff stared at Peggy in this position as she was still dressed except for her panties. She still had on the blue blazer, the white blouse and tie, the white knee high socks and saddle shoes and her skirt was flipped up over her back. Cliff was still dressed as well and his pants and underwear were down around his ankles. Peggy loved playing these games and keeping their clothes on made the games seem realistic in a bizarre way.
Satisfied that she was ready Cliff pushed his cock into her ass. Peggy gasped at the entry as Cliff slid all the way in with one steady push. He began to fuck her ass slowly and steadily as he had on other occasions. He had to admit to himself that it was a turn on fucking her ass while she was dressed like a school girl. He caressed her curvy bottom as he plowed into her ass and she grunted each time he hit home. It took Cliff awhile to cum a third time but he savored every moment of being in her gorgeous ass. Finally he felt he his orgasm approach and he let loose in her rectum and streams of cum filled her bottom. Peggy clenched and unclenched her anal muscles and milked every drop from his cock.
Cliff stayed in her ass for as long as he could and then he watched as his cock softened and slipped from her poop chute. Cum trickled out of her ass and ran down her crack between her thighs. It was an erotic sight to see her dressed like a school girl bent over a box with cum running out of her asshole. Cliff wiped his cock on the cheeks of her ass and Peggy cooed at the act. Cliff then took off his clothes and sat naked on the floor but Peggy remained in her position for several minutes before she moved. She was still fantasizing that she was a school girl in a private school that had just been fucked in the basement.
Cliff then moved over to Peggy as he was determined to see her naked and fuck her once more before he left that day. He had Peggy stand up as he undressed her. He first removed her saddle shoes and then her plaid skirt. He couldn't believe how erotically sexy she looked still wearing the blazer, blouse, tie and knee high socks while she was naked from the top of her sock to the blazer. He felt a surge run through his loins as he looked at her. Then he removed the blazer, tie and blouse. He looked at her again this time clad only in her bra and knee high socks and that did it for him. His cock was erect again. Cliff then took off her bra but left the white knee high socks on her.
This time he wanted to fuck her in bed so he directed her to go to her bedroom. He followed her up the stairs and watched as her fabulous ass moved side to side. They went to her bedroom and Cliff climbed between Peggy's legs and slipped his cock into her pussy. He fucked her long and hard bringing her to multiple orgasms. Peggy was just about to ask him to give her pussy a break when he stiffened and shot his load into her womb. Cliff's body stiffened as he ejaculated and then collapsed on top of Peggy. After several minutes he rolled to the side and lay along side of her. He reached over and playfully pinched her nipples and caressed her tits. They were both done for the day and they both knew it but Cliff was in no hurry to leave. Just then however Peggy played the game again.
"Oh what have you done to me? You did all the things my mother told me you would try to do. You have to leave she will be home at any moment and I have to get cleaned up so she doesn't find me like this," Peggy went on.
She jumped out of bed and ran into the bathroom. Cliff heard the shower running and thought to join her but the bathroom door was locked. He then went back to the basement to retrieve his clothes. Cliff returned to Peggy's bedroom but she was till in the bathroom with the door locked. So Cliff just shrugged his shoulders and left the house. It was all part of Peggy's game but once again he had had incredible sex with an older woman. He left for home knowing that she would be calling him for some more odd jobs.
PEGGY GOES TOO FAR
As he expected Cliff received a call on Sunday to come over and finish the projects from Saturday. Cliff was still amused in a way that he was getting paid a dollar an hour to work for Peggy when he spent most of his time fucking her. After breakfast on Sunday he drove over to her house and he was surprised when they actually worked together for almost five hours. Peggy then served some drinks and told Cliff that she had a special request for him.
Peggy wanted Cliff to put on a costume too this time. She showed him into the guest room where the costume was laid out on the bed. Cliff looked at it and he was flabbergasted. It was a black alb and a white collar. Peggy wanted him to dress like a priest. Cliff just stood in the bedroom in disbelief. He was not religious by any stretch of the imagination but he was not sacrilegious either. There was no way he could put on priest's clothing and then have sex with Peggy.
Peggy wondered what was going on with Cliff and she got a little impatient. Peggy walked into the guest room and she was surprised and disappointed that Cliff had not put on the outfit. Cliff looked at her and saw that she was dressed as a nun. That did it for him. She had gone too far. Cliff stormed out of the guest room and left the house. Peggy called after him and pleaded with him to come back.
"Cliff, I'm sorry. Please come back. Forget the costumes; we'll just have sex together. Please!" she pleaded to no avail.
Cliff walked out of the house and out of Peggy's life. He got in the car and drove away leaving her sobbing in her house. Peggy shut the door and she knew that once again she pushed things too far and had chased a man out of her life. She made herself a strong drink and flopped down in a chair. It took several moments before she regrouped and then she started thinking about how she could get another man into her life. She picked up the newspaper and look at the ads hoping to find another Cliff. Then a smile came over her face and she picked up the phone and dialed a number. Peggy was pleased when she heard a young voice on the other end.
Cliff drove home angry and frustrated. They had such a good thing going why did she have to fuck it up. There was no way he could ever see her again. The mood was broken and he couldn't imagine having sex with her again. Some of the games were okay and even erotic but she had crossed the line this time. She was just too kinky for him to continue the relationship. Cliff pulled into his driveway and got out of the car. It was about three o'clock and Cliff wondered if Steven was out by the pool. He decided to throw on his Speedo and shorts and check it out.
Cliff went over to the Faulkner's and when he entered the pool area he spotted Mrs. Faulkner lying face down on a lounge. He did a double take as he noticed that she was wearing a two piece bathing suit. Not only that but she had untied the top so that she would have any tan lines across her back. Cliff felt his cock stiffen and he thought to himself that maybe the day would be saved. He smiled and entered the pool area and walked toward Clara Faulkner.
NEXT CHAPTER
Cliff gets intimate with the Faulkners.