Cindy's Creative Imagination Ch. 02

INTRODUCTION

In chapter one you met Jim and Cindy and learned about Cindy's games and role playing. She always acted innocent and behaved as if she was the one being seduced. The first costume that Cindy wore was a private school girl uniform. Cindy acted as the innocent school girl and Jim was incredibly turned on by her looks and behavior. In this chapter Cindy will return with more surprises for Jim.

SUNDAY'S SURPRISE

Cindy had left the school girl uniform in Jim's guest room closet and Jim fully expected her to wear it again. Jim was surprised when Cindy arrived with her overnight bag with a different outfit in it. Cindy changed clothes in the guest bedroom and emerged dressed in a cheerleader outfit. Jim studied her wearing the cotton sweater and the short pleated skirt. The uniform looked very much like the USC outfit. Cindy went through the motions of a few cheers and as she swirled her skirt rose and showed off her fine ass clad in red panties. Jim felt his cock surge as he watched Cindy and thought of filling her ass with his cock.

"I shouldn't have come home with you. They will be looking for me at the dorm. I should be going now," Cindy said beginning the games.

"Nonsense, I'll take you home as soon as we are done," Jim replied in a strained voice.

"Done, what do you mean by that? What do you plan to do to me? Why are you staring at my legs?" Cindy said.

"Because you have beautiful legs and I am very interested in what is at the end of those legs," Jim responded getting in to it.

"Oh no, the other girls told me about boys like you. That you want to take off our panties and play with our pussies," Cindy added acting concerned.

"Well the other girls are right, so what do you say that we get started," Jim said anxious to get at her ass.

"I don't think so. I'm leaving," Cindy countered and then faked her departure.

Cindy turned away from Jim and then pretended to stumble and fall. The short skirt flipped up momentarily and Jim took in her curvy ass. Then Jim was on the floor behind her and he flipped the skirt up over her back. He pressed his hand on the small of her back holding her in place. Then with the other hand he pulled her panties down to her knees baring her fabulous ass. He caressed her beautiful buttocks and teased her nether hole with one finger. Jim was anxious to get in her ass but he was careful to lube it first.

"I don't think that you should be doing that. You shouldn't be sticking anything in my pooper. What is that greasy stuff on your finger?" Cindy said acting out the part.

Jim pushed his shorts and briefs down to his knees and freed his raging erection. He was hot and he was ready to take her ass again. "The greasy stuff makes it easy for me to put my thing in your pooper," Jim replied in a raspy voice.

"Oh no, you shouldn't do that. Nothing should go in my pooper," Cindy squealed.

Jim was not to be denied and he couldn't wait any longer. He pushed his cock into her well lubed ass and as usual it slid in easy. Jim was incredibly excited and he knew at that moment that he was going to cum quickly. He also knew however that he would be able to stay hard and fuck her ass a second time without pulling out. Jim caressed her lovely cheeks as he plowed her ass and took in her beauty. Cindy had her head on the floor turned to the side and she had a look of lust in her eyes. Jim then felt his ejaculation rush through his shaft and into her rectum. Cindy squealed when she felt the massive load fill her poop chute.

Jim never stopped moving as he continued to fuck her ass. Cindy could feel the semen being pushed around by his shaft and it turned her on. Jim reached under Cindy and slipped his hands under her sweater to find her braless tits. He fondled her breasts and tweaked her nipples with one hand and then he diddled her clit with the other. Cindy's cunt was dripping wet and Jim inserted three fingers in her. He located her g-spot and worked Cindy through multiple orgasms as he continued to ream her ass. They both were still clothed with their pants and panties around their knees and it was an erotic sight. At that moment Jim thought that sex just didn't get any better than that.

Jim and Cindy then got in bed naked and Jim began eating her pussy. He ate Cindy to one orgasm and then eased his cock in her pussy and fucked her through multiple orgasms until he came again flooding her womb with his seed. Jim loved the games they played and he enjoyed Cindy's creativity. Cindy and Jim showered together and then they got dressed. Cindy left the cheerleader outfit in Jim's guest bedroom closet and then she left the condo.

CINDY'S CREATIVITY

Over the next few months the dress up games continued with Cindy. She was always coming up with a new outfit and a new role to play. Jim loved the role playing as it made the sex very erotic and exciting. Each time Cindy would think of a new role she would wear a new outfit and the outfit would end up in Jim's guest bedroom closet. Some days Cindy would come over and select one of the outfits she had worn in the past and change in the bedroom. Jim never knew which outfit she would select to wear. Jim thought that if ever had a guest stay overnight he would have to hide all the outfits that Cindy had left there.

There was the time that Cindy changed into a workout outfit. She wore a sport halter top that showed off her firm abs with a spandex bottom that hugged her curves. Her ass looked great in the spandex. Cindy faked going through some exercise routines including leg kicks while she was on all fours. That did it for Jim and he got on the floor with her and pulled her spandex down to just below her buttocks. Jim then lubed Cindy's fine ass as she faked her protest. Jim then slipped his cock into her ass and fucked her until he shot his load deep into her rectum.

One day Cindy came out of the bedroom wearing only a string bikini. She play acted as if her good friend Jim put sunscreen on her by the pool. Cindy spread out a blanket on the floor and lay face down on it. Jim stripped down to his boxers and acted as if he was wearing swim trunks. Jim took the lotion and applied it to Cindy's body. He began with her shoulders and her back. Cindy untied the bikini top but she lay face down to conceal her breasts. Jim then put lotion on her legs amidst her weak protest that she could do that. Jim then moved his hands up to her ass and let his hands slip under the bikini bottoms. Cindy acted as she was offended by his advances but it wasn't long before Jin was sawing his finger in and out of Cindy's asshole. Satisfied that she was well lubed, Jim pulled off her bikini bottoms and lifted Cindy to her knees. Then he eased his cock into her anus and fucked her slowly until he ejaculated in her bottom. As always they finished up in Jim's bed with Jim making sure that Cindy had multiple orgasms.

They also had sex in Jim's car parked in his garage with the door closed. Cindy wore a poodle skirt with bobby sox and saddle shoes. It was a throw back to her high school days. They were in the back seat with Cindy's face buried in the seat and her ass stuck up in the air. Her poodle skirt was thrown over her body covering everything but her face. Her panties were down to her knees and Jim's pants and underwear were down to his knees. Jim fucked her ass in the back seat of his car and it was a wild turn-on. Another time Cindy showed up dressed like a guy. That time Jim pulled down her slacks and panties to her knees despite Cindy's mock protests. Jim announced that girls who dressed up like guys get fucked in the ass. So he fucked Cindy while she was fully clothed with her slacks and panties around her knees.

Then there was the time she dressed up like a girl scout selling cookies. That was one of Jim's favorite episodes. Cindy ended up on the floor with her short skirt thrown up over her back. Her panties were pulled down to her knees just above the tan knee high socks. Jim fucked her ass royally that day staying in Cindy's ass until he had ejaculated twice. As was the case with every visit, Jim always took good care of Cindy's pussy after the anal sex. The Girl Scout outfit was Jim's favorite and he had Cindy wear that one the most. His second favorite was the school girl uniform as both these outfits fulfilled Jim's fantasies.

THE MASSAGE

One Saturday Cindy played the role as an unsuspecting woman getting her very first massage. Cindy brought a special sheet with her to place on the bed along with a variety of massage oils to set the stage. Cindy played the shy role and covered her body with a large towel and keeping her panties on. Then she called to Jim and told him that she was ready.

"Good morning Cindy, my name is Jim and I will be your masseuse today," Jim said as if introducing himself for the first time.

"Hello, this is new for me. It is my very first massage. My girlfriend told me that I would feel good after having a massage," Cindy replied shyly.

"I will do my best to make you feel good. Just relax now," Jim assured her as he covered his hands with body oil.

Then Cindy felt his strong hands on her shoulders and back as he went deep into her body. Cindy just cooed as Jim rubbed her body all over from her head to her ankles. Then he had Cindy turn over and she held the towel tightly to her breasts as she did. She lay on her back with the large towel covering her breasts and her panties as Jim worked on the front of her body. Cindy was getting hotter and hotter as Jim's hand moved all over her and she felt her loins stir and her pussy throb. He had led her up to that state by teasing her many times as he massaged her inner thighs and allowing his hands to bush her panty covered pussy.

"Oh be careful my husband said not to let you too close to my privates," Cindy cautioned.

Jim laughed to himself when he realized that Cindy was going to play the role of a married woman. Jim continued to massage her and let his hand brush against her panty covered pussy several times. Jim could feel the dampness in her panties and the heat from her pussy.

"Cindy my dear it seems that your pussy is very wet. Would you like me to take care of it for you?" Jim asked in a sexy voice.

"I don't know. It's not right. I don't think that you should touch me there," Cindy gasped.

Cindy was so aroused by then that she just closed her eyes. Jim pulled the panties to one side of her vulva and stroked her outer lips. Cindy could feel her juices flowing and she bolted when he touched her hooded clit. He stuck one thick finger into her twat and with his other hand he tweaked her erect clit under the towel. Cindy went bonkers and came immediately but Jim did not stop and he brought her to multiple orgasms with his fingers.

"Oh you made me cum. You shouldn't make me cum. What would my husband say if he found out that you made me cum?" Cindy continued the game.

"Well your husband isn't here and he doesn't have to know," Jim replied now anxious to fuck her.

Jim removed the towel from Cindy's body and without asking permission he pulled her panties down and off of her legs. Cindy instinctively allowed her thighs to part and exposed her dripping wet pussy. Jim smiled, leaned over and ran his tongue up the length of her cunt. Cindy's body tingled and she shivered with desire. Jim licked her a few more times and he had her close to another orgasm when he stopped. Cindy reached for his head but he was out of range and she was confused by his actions but she went along with him.

Jim removed his tee shirt and shorts as he said to her, "Cindy it is time for you to reciprocate as well."

"But I don't do that, not even with my husband," Cindy protested mildly.

"Well today you will do it that is if you want me to take care of your pussy," Jim told her.

Jim moved back toward her and she spotted his erect cock. Jim lay on the bed with her so that his cock was beside her face and his face was aligned with her pussy. Cindy knew she was expected to take his cock in her mouth but she faked her reluctance and restated that she had never done that before. Jim guided his cock to her mouth and then he resumed eating her pussy. Cindy adjusted to the thick cock in her mouth as she enjoyed Jim's skilled cunt licking.

At this point Jim was very sexually charged and he knew that he would cum quickly. He did not warn Cindy that he was going to cum but just as she was humping her hips into his face with her own orgasm, Jim ejaculated into her mouth. Cindy was caught off guard with the first jolt of cum as it hit the back of her throat. She no sooner swallowed the first load then another load filled her mouth. This time Cindy swallowed but pulled her mouth off Jim's cock. She stroked it and aimed it at her face. The third volley hit her in the face and the fourth hit her neck and chest. Jim moved her head back to his cock in a sign that he expected her to suck him dry. Cindy willingly opened her mouth again and sucked on his cock until it softened in her mouth. Jim had returned to eating her pussy and he brought her to another orgasm.

Cindy faked her humiliation and anger at Jim for cumming in her mouth. "Oh what have you done? You came in my mouth and all over my face. That was so naughty."

Jim moved around the bed and lifted her legs up to where her knees touched her chest exposing her pussy and asshole. Jim began to lick her pussy once more and Cindy offered another mock protest. He kept eating her toward another orgasm and then he surprised her by running his tongue across her asshole. He licked her from her asshole up over her pussy and then back again. Cindy acted mortified but she was excited by having her ass licked. Jim would dip his tongue into her pussy and into her asshole.

"Oh you are so nasty. You are not to put your tongue in my pooper," Cindy gasped.

Jim then fastened his mouth on Cindy's twat as he slid a very oily finger into her asshole. Cindy flinched with the intrusion of her ass. She told Jim that she had never had anything in her ass and acted as if it were taboo. Jim worked her pussy with his mouth and her asshole with his finger as Cindy relished the anal invasion. Jim then pushed the thumb from the same hand fingering her ass into her pussy and held her in a bowling like grip. He continued to suck on her clit as he finger fucked her pussy and ass. Cindy was going crazy and her head was rolling from side to side in ecstasy. Just before Cindy came again Jim removed his finger, thumb and mouth. Cindy frantically tried to get his mouth back to her pussy but Jim climbed back on the bed and Cindy noticed that he was fully erect again. Jim knelt between her raised legs and eased his thick cock into Cindy's pussy.

Cindy squealed, "Oh no, you can't fuck me. I can't let you fuck me! Only my husband has ever fucked me."

"Let's see how this cock feels compared to your husband's," Jim said continuing the game.

She moaned as he filled her cunt. Jim rocked his body into her and kept his cock in constant contact with her clit. Cindy was crazy with desire and she was approaching a mind blowing orgasm. Cindy's body went rigid and then she exploded as she was overcome with the intensity of her climax. Her body seemed to go into convulsions and then slowed down until she finally collapsed.

Jim pulled out of her and then rolled her over onto her stomach. He lifted her by the hips until her ass was level with his cock. Jim slid his cock back into her pussy and slowly fucked her doggy style. Cindy turned her head to one side on the bed and stared into space as if she were in a trance. Out of the corner of her eye she watched as his big cock sawed in and out of her. Jim raced toward his orgasm and filled Cindy's pussy with cum. It was the first time in awhile that he had cum twice before he fucked her ass.

Jim pulled out of her pussy and got off the bed and Cindy flopped down on her stomach. Jim smiled as she got on her stomach and then he looked at her beautiful ass. He felt his cock stir as he thought about sliding his big cock into her curvy ass again. Then Jim put an ample amount of oil on his hands and began to massage Cindy's buttocks. Cindy relaxed as Jim massaged her ass. Cindy was in a dreamy state when she felt Jim's hand slid into the crack of her ass and a tingle ran through her body. Recognizing her pleasure, Jim allowed his fingertip to brush her nether hole. Cindy's body twitched but not in alarm but in excitement.

Then she felt Jim's finger probe her anus once again and she remained still and quiet as he had his way with her nether hole. Jim sensed her submissive state and took it to the next step. He eased his finger into Cindy's ass little by little until his finger was buried in her rectum. Cindy remained still and allowed Jim to finger her asshole and she felt tingles run through her body. Jim wormed his finger around in her ass and then he slowly removed it. Jim still needed more time to recover form his two ejaculations.

Cindy was in state of desire and ready to have her ass fucked when Jim rolled her over on her back as he spoke, "Time to do the front now."

Cindy had expected him to fuck her ass but she allowed herself to be turned over and she closed her eyes as Jim's hands rubbed oil all over the front of her body. He began with her shoulders and neck and then descended to her breasts. Cindy's nipples were hard as rocks when Jim massaged her breasts and rolled the extended nubs in his fingers. Then his hands moved lower to Cindy's thighs skipping her hips and pubes. He massaged each leg separately lifting it to his shoulder and rubbing it all the way to her pussy. His hands would occasionally graze her cunt and Cindy would flinch in response. Once again she was in a state of desire and she felt the need to orgasm.

"Do you need to cum again Cindy?" Jim whispered to her.

Cindy just closed her eyes and nodded yes. There were no mock protests this time. He gently rubbed Cindy's pussy with the massage oil and sought out her erect clit. Jim pushed two fingers into her pussy, rubbed her clit with his thumb and located her G-spot with two fingers. Cindy covered her mouth with her arm as an orgasm rocked her pretty body. She kept her eyes shut as her body jerked and spasmed on Jim's fingers. Jim removed his fingers from Cindy's pussy and brought them to his nose. He was pleased with her aroma. Jim's cock was throbbing by then and now he was anxious to cum again but he wanted Cindy's ass this time.

Jim rolled her over so that she was face down on the bed again and then he returned his attention to her ass. He kneaded her gorgeous ass cheeks and as he massaged her ass he put an ample amount of oil on her asshole. Then Jim began to probe her asshole first with one and then two fingers. Before long his fingers were moving easily in and out of Cindy's thoroughly lubed asshole. He lifted Cindy up by her hips until her ass was in the air as she rested her head on the massage table. He removed his fingers and climbed up on the bed with Cindy. He positioned the head of his cock at the entrance to her ass. As he eased his cock into her bunghole he heard Cindy gasp and hold her breath.

"Oh my, you are in my ass. I have never done this before. Please don't fuck me there. Please not in my ass," Cindy acted.

Jim was so hot that he shot his load sooner than expected when his cock was fully embedded in Cindy's ass. Jim stayed hard however as he always did as he knew that he could cum two, three and even four times without removing his cock from a woman's asshole. He had cum three times already but he was determined to cum a fourth time. Cindy felt the warm cum shoot into her rectum and she loved how it felt strangely good. She liked the soothing feel it gave her ravaged asshole and how she felt unbelievably full. Jim started to fuck her with long deliberate strokes as he admired her beautiful ass accepting his huge cock once again. Jim stroked her marvelous ass cheeks and told her how good she looked in this position with his dick skewering her luscious ass.