Jessie Just Wants to Have Fun

Story Info
A very adult trip to the playground.
5.1k words
4.25
39.6k
12
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Jessie had been moping around the big lonely house all afternoon. There were two hours of beautiful light left on this early July evening. Looking outside just made her feel more trapped and more lonely. Living in Mom's house was a bitch and getting bitchier. She could still hear her mom's angry tones from last week. "Again you have disrespected me and devalued my attempts to help you. You came in at three a.m., woke me and the neighbors, messed up the kitchen and left a nude boy asleep with his dick dripping on my white couch." To keep her free ride, Jessie had to agree not to have her friends visit her and to stay home for two weeks and help around the house. She felt like a little kid being punished. She was twenty-six now and grounded. Life shouldn't be like this.

Two months ago Jessie had to return home to live with mom again. This was the fourth time. First she flunked out of college for not studying; twice she ran out of money; now her sugar daddy had sent her packing. She still did understand why "Daddy" had been so mad. What was the problem, just because she was making it with a guy her own age when he came home? After all she took care of him. And sure he was good to her, made her cum several times each night and paid the bills. But she wanted to party, to experience it all. She was spoiled, demanding and drop-dead gorgeous. If only she could find someone fun who would pay the tab and not be so possessive.

Jessie was deep into feeling sorry for her self when she heard and ignored the doorbell. A very young familiar voice was talking to her mom, "Mrs. Wilson, can Jessie go to the playground and play." It was eight-year-old Tommy Busby from three doors down. Jessie had baby sat for him two years ago when she was destitute, living at home the last time.

Her mom was patiently explaining to Jessie's little admirer, "She is a little old for the playground now Tommy. I don't think she would want to go."

"Oh, please. Please, Mrs. Wilson ask her. She liked going with me before when she used to baby sit for me when I was little."

Her mom was surprised when Jessie agreed to take Tommy to the playground. As she watched the two walk away, she realized Jessie would do anything to get out of the house for a few hours, even if she had to sit and watch an eight-year old boy play on all the playground toys.

Tommy took Jessie's hand like he had a crush on her and led her to the near deserted, heavily treed playground two blocks away. When they got within a hundred yards of the teeter-totters, Tommy pulled away and began running toward a tall figure sitting in the middle of the first one. She kept walking. This was her turf. She grew up here. She was safe. Her beauty had intimidated all the local boys. She probably dated less than the average looking girls during her eleventh and twelfth grades.

The tall figure handed Tommy something and Tommy ran on through the playground and disappeared out the other side away from Jessie. As she approached she recognized her well-endowed, satisfying date with the dripping cock from a few nights ago.

"What was that all about, Brian? Where did Tommy go?"

"He's my kid brother. I paid him to go get you out of jail and then get lost." He reached down into a cooler and handed her a bottle of her favorite wine cooler. "You were lots of fun the other night. Did you mean all that you said about partying or was it all talk."

"Oh, I meant every word. But were could anyone find that kind of action in this one horse town. There are no parties here. There are no fun loving twenties except you and me. They all had the sense to split and stay split."

"You are wrong. There are lots of us here."

"Bullshit. Prove it. I bet you don't know two more guys our age in this town."

"What do you bet?"

"You call it."

"The other night, before we had sex, you said you were so horny that you could take on a baseball team. That's nine guys. Did you ever do anything like that?"

"Not nine. But I did three. I would like to take on nine. Nine might be enough to satisfy me."

"You saying, I didn't?"

"You were good but I could have handled more."

"All right here is the deal. I got you out of the house for a while. Tonight I challenge you to prove what you say. There are nine pieces of equipment on this playground. I'll get a different twenty to thirty year old guy to have sex with you on each piece before ten tonight. You have to satisfy them all, even if some come back for a second piece of you. You will definitely get satisfied. I'll be the hero of all time in this town for getting someone as beautiful as you to fuck my friends silly."

"If I remotely thought you could pull this off, I might consider it."

Brian raised his left hand over his head. Jessie saw a young man clad only in a white t-shirt and jeans walk out from behind a tree and sit down in a swing. Another big muscular man in only sweat shorts walked out and did two chin-ups on the horizontal bar. Two more, one to the spring rocky horse, the other to the monkey bars.

Jessie was breathing hard. Brian pushed his right hand up her skirt, slipped beside her panty's leg and pushed his index finger into her now slightly wet pussy. He finger fucked her slowly. The panties rolled around her nether lips and were uncomfortable. She recoiled.

"Including me, that is five. You backing out?"

Half in fear, half in lust she heard herself answer in a strange husky voice, "I'm not backing out. Where are the other four?"

"Take your panties off and I'll show you." Brian pulled his hand away. She could smell her need as she watched him take his finger to his nose and lips and lick away her juices. When her panties were free from her feet, lying on the ground, Brian reached forward and pushed two fingers into her this time. He found her g-spot, pressed firmly and began to rub her slippery clit with his thumb. His other arm had been raised all this time. Now he lowered it.

Two lean identical men with swimmers' bodies walked together and leaned against the slide at the children's play village. This is what she always fantasized about. She was breathing hard, pushing her cunt into his hand, grabbing for his fingers to make them go faster. His hand was wet. Another swimmer. This one at least 6'6" and black came from the bushes. He walked behind her, reached around and put a big hand on each of her breasts and thrust his hips forward. She felt and obvious joke press along the crease of her ass. It felt good. It delayed her climax. She reached her hand behind and slipped it between them. The first doubts ran through her. It felt like two beer cans stacked end to end. Warm, throbbing but not hard yet. She could feel his strength and his need. He was big and strong enough to take anything he wanted. What she felt was no joke.

Lastly a short, thin young man came out of the trees and sat on the uneven stools. They looked like tree stumps. She recognized him. He was the football team's equipment manager. Even his head was shaved. He looked too clean and too manicured. He sat with folded arms and looked straight into her eyes. She looked back, unimpressed. His tongue slowly slipped from between his lips until it lay on the bridge of his nose. She came in Brian's fingers.

Her knees almost buckled but she heard him say, "You start with the little rocking horses on springs." The black man pulled her sundress over her head. She was nude. The wetness between her legs was suddenly cold in the twilight air.

The little equipment manager came to her, pulled her down to his face and kissed her. She felt his tongue slip between her lips and lick the back of her throat. He pulled away and whispered, "First time through we will all wear condoms if we fuck you. That way we won't have to taste each other's cum when we eat you. Second time through you will be dripping from every hole and your body will be covered with our cum." Almost in a trance she let him guide her to the nude man slowly rocking on the horse.

"Step across cowgirl and sit on my saddle horn. Lean back onto the horse's neck and let's enjoy a slow ride." He didn't help. The little horse creaked as she lowered her pussy and felt his dick open her and slip easily in. Her wedge shaped seat forced his pubic bone tightly into her clit. His cock was average in every way but perfect for this ride. Its slight upward curve caused the head to rake across her spot on both the forward and back rock of the horse. The horse's spring complained in steady slow rhythm. Her eyes were closing on their own and rolling back when she felt an uncircumcised long cock being pressed into each of her hands. The twins were truly identical. Even their movements, caressing her breasts and thrusting into her fists were alike. Their cocks hardened, stood and throbbed alike. They bent down in unison and whispered in to her ears like one, "Later, Jerry will fuck you deep and push at your cervix while Terry will slide all the way up your ass. You will feel our cocks rubbing together inside you while you cum and cum trying to decide which of us is which."

Jessie could feel her cowboy jerk and respond to the twins' words. He was cuming. She came with him, not wanting the pressure on her special spot to ever end. He did not want anyone else to know so he kept rocking hoping to empty his balls into her again. She wanted to keep riding too but her body had told the others. They were pulling her off. Her pussy tried to hold on to her prize but it slipped from her pulling the condom almost off. It lay flopped over like a joker's hat and bobbed around on the still wanting cock.

Her cunt was taking over her mind now, screaming for more. More cock and now. It contracted and would not stop its demands. Her memory was confused. Her face was pushed up the slide and a cock slipped into her mouth. Her breast stopped against the cold polished steel on the edge of the slide. She prided herself in being able to deep throat a cock and let this one bury itself to its base. Before she could pull out for air. Another interested cock head explored her pussy's slit and found its way inside. The shaft was bigger than her cowboy's but it had no trouble stretching her and lodging deep. Instinctively, she reached between her legs to massage the loose swinging balls and rub her own clit.

Her blowjob skills were good. She finished one dick and another took its place. That one was anxious and blew its rubber-covered treasure quickly. She felt the sack tighten in hand. She thought, "Oh, not yet, I'm not ready" but it finished anyway.

She heard the higher voice of the manager say, "Stretch her out for me." She was picked up and laid face up on the cold slide with her legs held apart off the ground. His players could serve too. His lips closed on her clit, sucked and let go. He slipped lower, licked at her asshole, trailed upward and slipped his tongue as deep into her as some cocks she had known. It was like a snake inside licking every inch as his thumb rubbed gentle circles on her slippery pearl. She started to cum almost immediately. "Hold her arms out too, don't let her push me away."

She rode to the top of her orgasm and started to cum down. A finger slipped up her ass and pushed her high again. He was sucking her harder now. She felt his small hand slip three then four fingers into her and curl on her inside wall toward her clit. Jessie felt full and thought she wanted to pee; she struggled and rode the new strange feelings. This wasn't her clit wanting to cum. This wasn't her cuming on a cock. Her entire body was going to cum. It had never done that.

She could not complain or fight. Eight big strong arms held her spread to be assaulted by this wiggling serpent. Her belly tightened and tried to push her womb out so more of it could be licked and kissed. The serpent pushed at the dimple in her cervix. It felt good and was uncomfortable, so her insides retreated. Again the spasm came, again her insides pushed, again her dimple was tickled and again everything retreated. The pressure from his fingers was relentless and so very good. She really had to pee now. But a different pee.

When the contraction in her belly came again it came in ripples. Her legs trembled and her cunt contracted pushing an ounce of fluid out to distract the serpent. The licking did not stop and neither did her orgasm or her need to pee. Her stomach muscles cramped this time and she spurted like a hose. She could hear cheering but that did not matter. Staying on top of this wave forever was all she wanted.

She rode as long as her body would take it. Jessie almost screamed "NO, Don't stop" to her body when she went limp all over. She had almost passed out from lack of oxygen. Her cunt was in full spasm. She could feel it pulsing all on it own.

The tall black man said, "Bring her to me now."

She barely could understand what was happening as she was carried in the sitting position to the tree stumps where the very tall man sat leaning back on his hands. One of the other men must have taken hold of the black cock and lined it up in her slit. She was lowered down. Her thought was, "This is no big deal" as the ten-inch tool slipped in about four inches. She was soaking wet, slippery and well fucked. Still it lodged. She had to stretch wider. Her cunt was still in spasm and wanted to be filled. It chewed the black shaft, urging the man to fuck upward into her.

Her carriers lowered her instead. It hurt but she wanted more. It was her voice she heard giving orders, "Yes, do it. Work that cock into me. Stretch me. Make me take it all. Lower me. I want it in me. Do it." She did not get her wish. They knew five more driving inches in at once could damage her. Her body was worked back and forth and in circles. The only place their bodies touched was where the mighty dick reached into her. Three more inches went in. She was begging to cum again. She had lost count of her climaxes. Maybe it was just one continuous one now. Her body groaned in appreciation when the strong hands dropped her, impaling her with the last two inches. She had all ten inches twitching inside her. She looked down and could see the cock's head pressing out above her belly button.

Without any effort the big man wrapped his arms around her, lifted her, turned, knelt and laid her down on the rubber bark chips. His thrusts were hurtful and delightful. Jessie's body was cycling from wave to wave of pleasure. Any way she moved there was a man and she could touch cock. She was filled like never before. The air was filled with the wonderful smell of lusty men.

She had defeated her giant; his face contorted and he was emptying his balls. The twins moved to her to make their promise good. As Jessie felt the mighty black cock soften, she felt a long cock begin to work into her asshole. Only fingers had been there before but objection was out of the question. She was pulled back so all her weight reclined and settled on the new dick. There was no pain, just intense fullness as she was deeply skewered by the thin shaft. The other twin moved between their legs, knelt and pushed his cock into her stretched, well-fucked cunt.

Jessie could feel the two cocks rubbing their heads together inside her. They were only separated by a thin membrane. The dicks explored deeply every tiny spot inside her and then returned to rub together and tell what they had found. Some how the twins sat up and she slid down. She felt suspended by the two cocks. The pressure pushing into her clit and stretching up on her ass and pussy was intense. They worked in unison as they thrust into her. If she pulled away from one, to ease the stretching, she was stretched even more by the other shaft. The slight pains were driving her crazy. She wanted them to rip into her and take her to new heights, but all she got was the maddening slow thrusts and stretching.

She was getting loud now, demanding to cum harder. She felt two men kneel and begin to rub their cocks on her feet. She felt two more dicks slip themselves into her hands. She opened her mouth to scream in pleasure but a new short thick cock filled her mouth. It was wet and covered with pre-cum. There was no condom.

Her body was screaming now. Cuming and wanting to stop and not to stop. Her womb was squirting again. She could feel heat all around her and pre-cum coating her hands, feet and tongue. The cock in her mouth was growing and arching into her. She needed more sensation. Some angel knew. Her hair was pulled, both her nipples were twisted cruelly and cum flowed over her taste buds. Her body found its long sought, flowing release. Jessie's body was soaring in pure pleasure.

She knew she was about to loose consciousness and struggled to hang on. Her mind pushed out a single stream of thought before she fainted. "Jessie, you have survived round one. The merry-go-round, the parallel bars, the swings, the sand box, the benches haven't been used yet. Our cocks will be more difficult to satisfy in round two."

Jessie was resisting waking up. She knew she was being moved but did not care. The cold steal bars were a shock to her senses. She was six feet off the ground looking down from the monkey bars and could feel the weight of her breast dangling through the slats. The big horizontal bars ran down each side of her body and across her widely spread thighs. The muscular man was climbing up the ladder's rungs, getting high enough so he could fuck her. Below her she could see her following choosing what they wanted to do. Two reached for breasts, one pulled at the lips of her pussy, one rubbed and kissed a dangling foot. The others watched between her legs as she opened to receive a cock into her body once again. Round two had started.

The bars were uncomfortable at first but the appreciative hands and pumping cock were making her forget that. Her pussy lips were being pulled and wrapped around the thrusting penis. The experiment must have shown promise. The hands moved from her lips, wrapped around her entire vulva and tightened enough to give more friction to the shaft inside her and force it to drag along her clit with every movement. Jessie's nipples were long and stiff. They were being pulled and squeezed like a cow's teats would be milked. She was totally venerable to what ever the hands, cocks and eyes wanted. She was almost there when she felt cum spewing into her and reducing the friction of the thrusts. The cock pulled out of her, leaving her open and cold. The hands holding her pussy tight let go and those two suitors changed places. The new hands choked her tight and the new cock pushed hard sliding over her clit, opening her and then pumping another load of cum into her. This time the friction was too much. The slap to her ass stung just as she started to cum. She wanted more, "Yes, spank my ass and fuck me."

She wanted this game to continue but her men had other equipment to try. She was carried to the swings. Two were twisted half around and a wide board was placed between the seats. She was laid on her back and there was a ring of hard cocks all around. One man took her ankles in his hands spread her wide and slipped into her. His thrusts pushed the swing away slightly and he pulled her back. When her thrust too hard and slipped out, teamwork was required. A second man moved to her head and pushed his cock into her mouth offering himself as resistance to his thrusting buddy. Jessie was rocked back and forth between two hard cocks. Before they came the circle rotated and two other cocks entered her. This time she saw her self as an animal roasting over a fire, a spit run through her body holding her in place.

The circle continued to rotate. Some of the men came. Her pussy held what it could and her throat swallowed what it could. Her pussy was in heaven. Her mouth was a little sore. At least four times around the circle rotated. Thirty-six cocks of all sizes went into her cunt and mouth. She had cum many times but was in frenzy now she wanted what all women want, "More."

12