Jimmy's Well-Paying Summer Job

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

"Jimmy."

"Yes?"

"Take off your underwear."

Jimmy looked at her, slid his fingers into the waistband and slid his underwear down, kicking them off of his feet after they dropped down all the way.

Looking back at Diana, she was staring at Jimmy's rock hard cock, standing proudly and finally free for her to view without the embarrassment he feared so much in the yard that morning.

Jimmy had a nice dick. About 7 inches and somewhat girthy, but not overly large. It stuck straight out from his body with a very slightly upturned bend at the end. The head was proportional to the shaft with a large vein running down the left side on the top.

Diana looked back at him and pointed at the shower to her left. "Get in." She said.

"In the shower?"

"Yes."

Jimmy got in and Diana stepped in behind him, still wearing her bikini bottoms. She turned on the water and it got hot almost immediately.

The shower was adorned in grey marble tile with a built-in bench on the side opposite the entrance. It was big enough that it didn't even have a door, it was a deep walk-in with a waterfall faucet on the ceiling.

Diana and Jimmy stood beneath the water and she reached for a bottle of body wash. She poured some into her hands and began lathering Jimmy's body. She worked her way down from his neck, to his chest, and continued on.

As she moved lower, she took Jimmy's throbbing cock into her hand and began washing it with long slow strokes. She looked into his eyes, not saying a word as she proceeded. Jimmy stared back silently for as long as he could until he tipped his head back and let out a long shallow groan of pleasure.

Diana continued, rolling his balls in her hands, still silently washing his private parts. She finished and let the water rinse off for a moment before grabbing body wash again.

"Give me your hand." She said, squirting a similar amount into his hands. She put the body wash back on the bench, then reached for her bikini bottoms and slid them down.

Jimmy looked down to see her very fit body exposed fully to him for the first time. He inhaled deeply. Her now removed bottoms revealed a tightly groomed triangle of shortly trimmed hair just above her slit. He looked back up at her face where she was looking at him again. She moved her hands behind her head to lift her hair from her shoulders then looked at him expectantly.

Jimmy took the cue and began washing her body the same way she had washed his. From the neck, to the shoulders, her upper chest, and then slowly, very slowly, to her large, soft breasts where he lingered much longer than necessary. Lathering and softly squeezing as he went, he had a quick moment of confidence in which he gently pinched both of her nipples.

Her eyes, watching his hands at work the whole time, shot up to meet his, where he was smiling at her slyly. They laughed, and he continued to wash her.

He now moved down over her flat stomach, eagerly pushing lower to reach between her legs. As his hands moved lower, she closed her eyes. Jimmy noticed this and also took note of her heavier breathing. He moved his hands about between her legs, but she reached down and took his hands in hers. Not saying a word, she simply guided his hands. He followed her lead.

She lifted his hands back to her breasts then looked up at him.

"Jimmy." She said.

"Yes?" Jimmy replied with smile, realizing that he liked this way of addressing him and giving orders.

"Kiss me." She said.

He wasted no time. He had been waiting for this throughout this entire interaction. He kissed her hard and deep, moving his lips against hers. He took her plump lower lip into his mouth gently licking and sucking on it before very softly biting it. Her eyes shot open immediately, staring into his.

"Where did a 19 year old boy learn to do that?" She asked with a smile.

Just as Jimmy was about to reply, Diana put both of her hands on his chest and slowly pushed him back towards the bench.

"Sit." She said.

He sat down as she reached up and slightly adjusted the faucet so that the warm water would pour over both of them at the back of the shower. Jimmy sat straight back against the wall as Diana pushed his legs apart and slowly knelt down between them. She grabbed the back of his knees and pulled him out slightly from the wall, lowering him into a slouching position where she would have a better angle.

Diana looked him in the eyes, her green emeralds glistening under the hot water pouring from above. She crouched down lower and moved away from his body and began gently kissing his left thigh, moving closer and closer to his throbbing penis with each kiss. She stared into his eyes the whole way. As she got closer to his hard cock, she moved to the right leg, gently brushing her lips against his balls, touching her forehead to the underside of his dick she moved across.

"So this is what its like on the other end of this..." Jimmy thought as he noted how her actions eerily mimicked his with Kayla.

As her lips moved closer, Jimmy's heart was racing. He knew what was coming and he could hardly take the anticipation. Jimmy's dick had been in a few girl's mouths by now, and Kayla's was his favorite, but as he sat back and ran through the morning he was having today, he knew something mind-blowing was happening.

Diana lifted her head just above his dick, staring up at him until he locked eyes with her again. She brought her hands up both thighs from the knees until they reach either side of it. She opened her mouth slowly and with her hands gently guided his cock downward onto, then in between, her waiting lips. She pressed her face forward at a snail's pace taking in the first couple of inches.

"Oh, fuck me..." Jimmy moaned.

"Not just yet." Diana replied softly.

Hearing this, Jimmy momentarily broke from his pleasured stupor. "Not yet? Did she just say 'not yet?'" Jimmy thought. "Does this woman want to fuck me?"

Meanwhile Diana had gradually quickened her pace. Still moving somewhat slowly, she was taking 5 or 6 inches of Jimmy into her mouth with each plunge or her head toward his body. Slowly and gently working her tongue along the underside of his shaft, varying the pressure each time, she found the sensitive area just below the head and pressed against it with her tongue.

Jimmy was in a state of bliss. He couldn't believe how good this felt. The look he saw in her eyes downstairs in the kitchen was truly the look of a woman with experience he couldn't have imagined at that age.

As he was taking in the sensations for a few minutes longer, eyes closed, and head under the pouring water, Diana said, "Jimmy. There's a bottle of lotion there next to you, give it to me."

Jimmy opened his eyes and found the bottle. She stood up and adjusted the faucet so the water now fell behind her and on her back, no longer upon him.

Getting back on her knees, she moved closer to Jimmy and stood up straight. She opened the bottle and squirted a small amount of the sweet smelling lotion on to the head of Jimmy's cock, then slowly stroked it up and down to lubricate it. Then Jimmy's eyes widened as she squirted a large amount of lotion into her cleavage and gently rubbed her tits together to spread it around a bit.

Jimmy knew what was coming and he had only ever seen it in the porn he liked to watch online. Kayla's and his previous girlfriend's tits weren't big enough for this, but it was always a fantasy at the top of his list.

Jimmy was going to fuck Diana's amazing tits.

She grabbed his dick and pulled it slightly toward her, standing it up straight rather than pointing back at him as it naturally did. With her free hand she pushed her left breast against the right and enveloped Jimmy's big hard dick with both of them. Jimmy threw his head back and she began working his cock up and down between her big tits.

Pushed together, her large nipples looked back at Jimmy like wide staring eyes. He stared right back wondering if these eyes were maybe as beautiful as the green ones on her face. As she moved her tits against his cock, Jimmy began to leak precum.

"Oooh, mmm." Diana said as she looked down and saw it. "I absolutely love precum..." She said as she pulled in her chin to give her tongue access to the tip of Jimmy's leaking cock where she lapped up his natural lube with a few slow flicks of the tongue.

"Delicious!" She said as she spread the last of it over her lips with her tongue.

Diana worked Jimmy's dick for a while until it was purple. She was surprised that he was able to hold back his cum for so long, given his age and the utter surprise of this entire situation. She had feared earlier in the day that if she took it this far, he'd blow as soon as she touched him.

She stood up and said, "Jimmy, come here in front of me and get on your knees."

Jimmy smiled and did as he was told. He needed no further instruction, this was his specialty.

Diana looked down at him and put her left leg past his head with her foot on the bench behind Jimmy where he was just sitting when she sensuously fucked his hard cock with her big soft tits.

Jimmy began working up her thigh with soft kisses, just as she had done to him, just as he would kiss Kayla's leg.

He moved more quickly than usual, seeing Diana's fully engorged lips in front of him, he knew that she was ready for his tongue. He took his time in taking in the view of her drenched pussy in front of his face. He had only been this close to a few at this point in his life and he was always curious about them.

Diana's soft triangle of pubic hair added a never before seen accent for him, and her somewhat large lips hung a bit, contrasting largely with Kayla's very tight, small lips. He loved it. He loved them both and took them for what they were, the amazing structures of the female body. No two were ever the same.

He sucked one of Diana's large lips into his mouth and gently massaged it with his tongue, then moved to the other to do the same. All the while, he was working his way up to the top where her fully erect clit was waiting for him. As he kissed it and gently touched his tongue to it for the first time, Diana gasped loudly and immediately grabbed the top of his head with her left hand, the right supporting her weight against the shower wall.

Jimmy went in circles, gently increasing and decreasing the pressure as he gradually increased his speed. Diana was even more receptive to his motions than Kayla, and quickly began twitching and gasping for air involuntarily.

She grabbed his hair and pulled gently, losing more and more control of herself as he continued. As Jimmy continued, he felt the warm liquid, not just from the shower head, but from Diana's swollen and leaking vagina, moving down his chin. He smiled as he always did in this position.

He loved making a woman cum.

Jimmy picked up the pace and Diana's body followed suit. She soon began trembling, her left leg against the side of his head shaking uncontrollably. Diana began moaning loudly and vocally imploring him to continue and not slow down. Jimmy reached both hands behind her, grabbed her ass firmly and held her body tightly against his face.

Diana let out a loud yelp and Jimmy smacked her ass with his right hand. He pushed harder with his tongue and moved it rhythmically as fast as he could. Diana grabbed his head and began sucking air in short, stilted gasps until she tensed up and released a loud, "Ooooohhhhh!" as her hips thrusted wildly into his face and she struggled to maintain her balance as she leaned against the shower wall. Jimmy felt her juices washing over his chin, a gush like he had never felt before.

As he slowed down and stopped he held her up with his hands behind her back. He stood up slowly, kissing her stomach, and taking both nipples into his mouth briefly before standing and looking her in the eye.

She repeated the question she had asked earlier, "Where did a 19 year old boy learn to do that?"

Jimmy smiled back at her as they stood under the water for another couple of minutes and rinsed the lubricants, both natural and man-made, from their bodies.

Diana turned off the water. She looked at Jimmy, looked down at his dick, still hard but not quite what it was between her tits, grabbed it and led him out of the shower. She threw him a towel, and almost instinctually knowing what to do, he dried her body before his own, spending just a few extra seconds on her exquisite chest.

When he finished, he saw her standing by the sink looking at him with a sexy smile. He knew they weren't done.

Jimmy took a deep breath. He was excited but he knew that this could big one of the biggest moments of his life so far, and he wasn't sure that she understood the stakes.

Diana beckoned him with a finger, and turned toward the bedroom. Looking at the clock she said, "We've got one hour until my son gets dropped off and not much longer than that for you to finish what you actually came here to do. But first, we have some...finishing...to do here."

She sat down on the bed in front of him and pulled him toward her. At his height, his dick was pointing straight at her face. She pulled him in swiftly by the hips and attacked his dick, quickly hardening to its full size. She bobbed her head on it at a fast pace and Jimmy could barely breathe.

She worked her tongue frantically, but in rhythm, against the underside. Jimmy was breathing heavily now and feeling his balls straining. Diana looked up at him, popped his dick out of her mouth and said, "Now its time for the spider to finish off the fly." With a devilish giggle.

She scooted back on to the bed. Lying on her back, she spread her legs and again beckoned Jimmy towards her. He complied, and was now lying atop her, supported on is elbows, looking her right in the face.

"Jimmy." She said, this time not waiting for his reply, "I want you to fuck me. Fuck me with that big dick like you fucked me with that tongue, and then I want you to put your big load right on my big tits so I can lick it up. I want your cum inside me today."

Jimmy smiled with pleasure, but felt the serious unease of such a moment growing inside him.

She sensed it as she looked into his eyes.

"Oh, Jimmy. You've never done this before, have you?"

"No." He said sheepishly.

"No no, don't be ashamed." She said in a loving tone of voice. "There's nothing to be ashamed of or embarrassed about."

"I'm not embarrassed, I've just really wanted this to happened before now...but it hasn't."

"Your girlfriend isn't ready?" She asked as if she knew the whole story already.

Jimmy looked up into her eyes. "No." She won't even talk to me about it."

"Well, Jimmy," Diana said, "she's sure got you on the right track with everything else. That tongue is dynamite."

"Haha, yeah I think so too." He said.

"Jimmy, I want you, but I'm not forcing this. If you want to fuck me, I'm right here ready for it, and god knows I need it, but I'm not going to make you do it."

He looked back at her, ran back all the thoughts of his recent frustrations with Kayla in his head in an instant, and thought about what to do. Deep down he knew, he had known for weeks. He loved Kayla, but she was holding him back. He knew what he wanted and how he wanted to live his life. Maybe it wasn't a picture of purity, but he could reckon with that another day. Right now, he made up his mind. The spider was going to eat her fly. And his cum too.

Jimmy looked into Diana's eyes then suddenly kissed her deep and hard. She groaned with pleasure, "Oohhh Jimmy."

He moved his right down her body, pinching her nipple on the way, eliciting a yelp from her. He grabbed his hard cock and aimed it straight for the lips of her pussy, still swollen from the shower and ready to take him in.

With a slow, but powerful thrust, Jimmy put himself inside Diana and let instinct take over. He propped himself up on his hands and thrust powerfully into her. Her eyes opened wide and she gasped with pleasure. Jimmy quickened the pace then lifted her legs and bent Diana's knees back towards her body to get as deep as he could.

A pained expression of utter pleasure came over her face as he sped up, pounding her drenched pussy with his powerful cock.

After sucking and tit fucking in the shower, Jimmy knew he didn't have long. He thought about the first glimpse at her beautiful eyes at the front door that morning, the view of her ass in the yard, her amazing cleavage, and most of all, how she fucked his leaking cock so well with her incredible tits. All of that, on top of the indescribable warmth and soft tightness gripping his dick as he thrust in and out of her in that moment, was leading him straight the point of no return.

Jimmy began to grunt harder and louder.

"Are you close?" She asked.

"Y-yes!" He said.

Diana pushed him off of her, jumped off the bed down on her knees and pushed her big tits together. Her incredible big areolas staring back at Jimmy again as they did in the shower like a second set of wide open eyes.

"Give me all of your cum!" She exclaimed.

Jimmy stood up in front of her and with just a couple quick strokes, his cum exploded on to Diana's heaving chest. She pushed her tits together as the first spurt of jizz flew towards her and hit her right nipple dead on. Jimmy's second stream of cum shot harder and clipped her chin before dripping down on to her upper chest. He fixed his aim and blew his third, fourth, and fifth streams of cum, on to her upper chest and let it run down towards her nipples. A sixth, a seventh...

"Oh fuck yes!" Diana yelled as she reveled in the pleasure of Jimmy's bursting penis, blowing a truly massive load of cum all over her just as she wanted.

After the eighth shot, Jimmy's dick began to dribble and drip more than shoot. Diana, letting go of her tits, reached for his still throbbing and pulsating penis and spread the oozing remains of his nuts over her lips and cheeks. She was insatiable.

Jimmy leaned back against the bed and watched. He looked down at her huge tits absolutely glazed in his cum then watched as she smeared every last remnant from his dick on to her lips.

She was staring into his eyes now with a smile resembling the one she made when they first met at the front door hours earlier.

She let go of his dick and looked down at her tits. She pushed them together and looked up at him.

"Oh Jimmy. Look at what you've done to my big soft tits. You've covered them in your cum." She was smiling slightly now and putting on a voice to add to the effect.

"Jimmy? Have I ever told you how much I love the taste of cum? Of your cum in particular? That precum between my tits in the shower was such a nice appetizer, but now I have a whole meal here on my tits and I need to finish every last bit. But first, I want something to remember you by. Hand me my phone, its right over there."

Jimmy reached over to the bedside table and grabbed her phone. She took it from him and held it out in front of her, snapping a picture of her cum-drenched chest. She threw the phone back on the bed and smiled at him.

She then stared into his eyes as she took her right breast to her mouth and sucked her nipple into her mouth. She sucked off the first shot of Jimmy's huge load that he had put on it. Then she began licking the rest of her right breast, getting all of the cum her tongue could possibly reach into her mouth. For the globs that couldn't be reached, she used her finger to gather it and spread over her nipple before licking it clean once more. She then repeated the whole show with the left breast, never breaking eye contact for a moment.

When she was done, Jimmy fell back on the bed in a delirious state of ecstasy and exhaustion. Diana sidled up next him and draped her arm over his chest. He could feel her large breasts pressing against his left arm and the left side of his body.