Cindy's Creative Imagination

INTRODUCTION

Cindy 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 not 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 Jim play with her bottom and even spank her occasionally. Cindy had shoulder length brown hair and matching brown eyes. She stood at 5'5" tall and weighed a very fit 115 pounds.

Cindy was a very creative lover and Jim enjoyed having sex with her. She loved to get dressed up in different outfits and act as if she was being seduced for the very first time. She loved to role play and she would keep her outfits at Jim's condo in the guest bedroom closet. Every once in a while she would buy a new outfit and surprise Jim.

Jim Carson at 24 years old 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 college and his body was chiseled. Jim was experienced with girls as he had had sex with a number 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.

Jim worked for a virtual office consulting firm which meant that he worked from home when he wasn't at a client site. Jim met Cindy when he purchased the condo as she was the on-site manager for the condo community. Jim and Cindy were very discreet about their relationship which was easy to do since Jim worked out of his home.

HOW IT GOT STARTED

Cindy was taken with the handsome young single man as she had not expected someone so attractive to purchase a three bedroom condo. Jim had never even thought about sex with an older woman and it wasn't on his mind when he met Cindy either. One day Cindy came to Jim's condo to change the flood lights in the vaulted ceiling. She was dressed in a summer smock that came down below her knees. It was not a flattering dress and it did not reveal Cindy's charms that were under it.

Cindy was standing on the ladder when she asked Jim to hand her the flood lights one at a time. Jim handed her a bulb and then stood by the ladder. As Cindy stretched to replace the light her smock rode up on her legs baring her shapely calf. Jim 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.

Cindy turned to him and asked for another flood light as she handed him the old one. Jim had to move carefully as his cock was hard and pressing against the leg of his pants. Cindy didn't notice his hard-on at the time but she was somewhat suspicious that Jim 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 Jim, she asked him to hold the ladder and then she stepped up one more rung. Jim 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 Cindy 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 Cindy pushed it to the next level.

"Oh my I am so sorry! Look what I have done to you," Cindy said as she made her descent down the ladder.

Jim 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," Cindy went on.

Jim thought that this was really weird behavior. 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," Cindy whimpered and then said, "You're not going to spank me, are you?"

Jim 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 then curled up on Jim's sofa and acted as if she was afraid to be punished.

"Please don't, don't put me over your lap and spank me," she begged mockingly.

Jim caught on that she was really giving him instructions rather than protesting. He moved over to the sofa and sat in the middle as Cindy cowered in the corner of the sofa. Jim was starting to like this game and he reached for Cindy. He pulled her over his lap and her body pressed against his erection.

"Pleased don't flip my dress up and spank me," Cindy faked again but Jim did just that.

He flipped her dress up baring her legs and her panty covered ass. Jim stared at her beautiful shapely legs and curvy butt. He then realized just how pretty and shapely Cindy 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 Jim 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. Jim began to spank Cindy's bare ass lightly and he liked watching her buttocks jiggle each time he slapped them. Cindy made believe that she was in agony and she began to beg Jim 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," Cindy pleaded.

Jim was in disbelief when he heard her. She wanted his cock in her mouth. She was going to blow him. Jim couldn't move fast enough. He lifted Cindy 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. Cindy smiled when she saw the impressive cock and she knelt in front of him. Jim grabbed her head and pulled it toward his cock. Cindy willingly took the cock into her mouth and within seconds she was deep throating him. No girl Jim had ever been with ever took his entire length into her mouth but Cindy was handling his cock with ease.

Cindy was an accomplished cock sucker and Jim 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 Jim 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. Jim fired a barrage of cum into Cindy'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 Cindy 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 Jim couldn't stand the sensation any longer. He was still hard however and Cindy 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," Cindy acted out her shame.

But Jim knew that they weren't done and he pushed Cindy 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 Cindy's cunt was sopping wet. Cindy gasped as his cock hit home and she wrapped her legs around Jim's torso. Jim pounded her pussy with his rock hard cock and Cindy grunted and groaned every time his cock went all the way into her womb.

"Oh my, this is going to be a quick one!" Cindy gasped.

Her body lifted off the floor with the intensity of her first orgasm. She held Jim tight as her body shook violently and he felt her juices cover his cock. Jim's pecker was swimming in Cindy's pussy but he continued to pound at her in search of his second ejaculation. Cindy was extremely turned on and she felt another orgasm building in her body as Jim raced toward his. She felt his body tense up and then with one more thrust deep into her, Jim shot streams of cum into her hot cunt. Cindy felt the ejaculation and it sent her over the edge again. She dug her heels into Jim'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. Jim thought about his situation as they both remained coupled together still partially clothed. Cindy had not removed her dress only her panties and Jim still had on his pants and underwear between his knees and ankles. Jim eased his cock out of Cindy'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," Cindy said and then picked up her panties and ran to the bathroom.

Jim 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. Cindy eventually came out of the bathroom and left the condo without saying a word. Jim thought about what happened and he was really turned on by Cindy's behavior as it had gotten him very excited.

Cindy returned to her office and called maintenance to pick up the ladder at Jim's condo. She was a little concerned that she may have pushed her little game too far. She hoped that she hadn't scared him away. Jim 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 come on so strong. That was the problem Cindy had with men; they thought that she was too kinky and she scared them away.

That night Jim lay in his bed and thought of Cindy. He hoped that she would visit him again so that he could see her again. He thought of her oral skills and the way they fucked. Jim got an erection reflecting on the afternoon sex and he jerked off thinking of Cindy. He wished he had fucked her some more but now it was just a memory. Jim 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.

CINDY CALLS AGAIN

The next day the phone rang and it was Cindy on the line. She asked if she could come over that day and speak with him. Jim told her to come over and then he had a quick breakfast. When she arrived she was wearing a much shorter skirt than she had the previous day. Jim used every opportunity to look up her skirt and this time she was not wearing panties. Cindy 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," Cindy play acted.

"You're not wearing any panties Cindy," Jim 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," Cindy said acting shyly.

"But Cindy you let me look up your skirt and now you should be punished," Jim replied.

"Oh please don't spank me again and don't even think that you can put your mouth on my cunny," Cindy whimpered.

Jim realized that she wanted him to eat her pussy first that day. He had eaten pussy before and he liked doing it. Jim had Cindy stand up in front of him and then he ran his hands up Cindy's legs and cupped her buttocks pulling her toward his head. He pushed up her skirt and began eating her pussy. Cindy grabbed his head and held it tightly to her quim as Jim dipped his tongue into her and sought out her clit. Cindy was overwhelmed with desire and she came quickly dousing Jim's face with her female nectar. Jim kept eating her until she couldn't stand it any longer and collapsed in his arms. He carried her into the bedroom.

Jim 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. Jim eased his cock into her sopping wet cunt again and Cindy gasped as she had the first time. They fucked like animals as they both raced toward their orgasms. Jim was quick to fire and he let loose a barrage of cum into her pussy. Cindy 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.

Jim then pulled out of her and placed Cindy over his lap. His pants and underwear were down around his ankles and he was still wearing his shirt. Cindy was still in her summer dress and Jim pulled it up exposing her ass.

"You have been naughty again so I am going to give you a good spanking," Jim teased as he ran his hands over her shapely ass.

Jim 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. Jim felt his cock harden under Cindy's lap and she felt it too.

Cindy 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."

Jim looked around and spotted the lotion on his nightstand. He leaned over to retrieve it holding Cindy on his lap as he did. Jim got the lotion and squirted it all over Cindy's ass. Jim then massaged the lotion into Cindy's buttocks. He took his time as he loved handling her beautiful ass. Jim's cock was erect under Cindy and she could feel it poking into her pubes.

"That feels so good on my sore bottom," cooed Cindy and then warned, "But you mustn't stick your finger in my pooper. That would be so nasty."

Jim 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. Cindy 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."

Jim did just that as he finger fucked Cindy's asshole. Then he switched fingers from his index finger to his middle finger and pushed it in as far as it would go. Cindy wiggled her ass again and Jim was getting hotter by the second. He decided that he wanted Cindy on all fours while he played with her ass and finger fucked her. He pushed Cindy off his lap and told her to get on all fours on the bed. Cindy 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.

Jim 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. Cindy loved the feeling of the three fingers in her and she was pleased that Jim 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," Cindy said sounding childish.

Jim thought about her statement, "Gees, she asking me to fuck her in the ass."

Jim had never fucked anyone in the ass before. He had heard in college 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 Cindy's asshole. Jim had used lotion and saliva 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.

Jim pushed his cock into her asshole and when the head cleared her sphincter Cindy let out an audible gasp. The feeling was incredible for Jim as his rock hard cock nestled into Cindy's snug warm sheath. He pushed his cock in all the way and then pulled back so just the head remained in her ass. Jim fucked her slowly as he wanted it to last forever. Cindy 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.

Jim moved steadily and slowly in and out of Cindy's ass until he felt his release building in his balls. Jim picked up the pace and thrust quicker and harder into Cindy'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 Cindy's ass. Jim felt stream after stream of cum shoot through his cock and go deep into Cindy's rectum. Cindy loved the feeling of cum coating her anal channel and filling her rectum. Jim had shot an enormous amount of cum in her asshole and Cindy couldn't remember the last time she was so full.

Jim stayed in her ass for minutes as Cindy used her talented anal muscles to milk his cock dry of any cum remaining in his shaft. Jim's cock began to soften slightly and he let it slip from Cindy's asshole. He looked at her dilated anus and it looked vulnerable as a little bit of cum trickled out of it. Jim was then shocked when Cindy 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. Of course Jim had no idea that Cindy douched her ass and pussy thoroughly before she visited him.

"My poor cunny needs attention right now," Cindy pleaded.

Jim realized that they were still dressed. Cindy 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. Jim now wanted to be naked and he wanted to see the rest of Cindy's body. He still hadn't seen her tits yet.

"Cindy I want to see you naked. Let's take all our clothes off," Jim 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," Jim replied playing the game.

Cindy acted shy as she stood up and removed her dress and bra. Jim watched her as he took off his own clothes. Cindy had a great figure and her tits were perfect, not too big and nice and firm. Cindy lay back on the bed and she opened her legs for Jim. 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.