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.