Kelli and Bill (Part 2)

Kelli and Bill
(A “Cum Diaries” Story)

The "Cum Diaries" are occasional fictionalized accounts of stories told to me by my readers, in this case of my short story “Best Ever”. That began an ongoing conversation with KT in North Carolina about her experiences.

Part 2

Spring turned to summer and school ended for the year. Bill planned on leaving for college in late summer, with his father taking some vacation time to drive him across country.

They lived near a state park with a popular beach and, since they had the entire weekdays to themselves, Kelli and Bill would often spend warm afternoons there. Kelli had outgrown the one piece swimsuit she had the previous year. After considerable badgering, she finally convinced her mother to get her a cute two piece that was not exactly a bikini but did tend to emphasize her round firm butt. While the beach at the lake was often crowded, only a very few braved the cold water, especially early in the season.

It took a dare, but after barely standing in the edge of the water, they took each others hands and ran in until they were completely submerged, yelling and screaming their protest as the frigid water engulfed them. While the water only came up to about Bill's belly button, it covered Kelli's little tits, making them stiffen even more.

I'm freezing, let's get out now,” she complained as Bill wrapped his arm around her waist and pulled him close.

Not yet,” he laughed, thumbing her erect nipples just below the water level, “I want to try something first.”

What's that?”

Her step brother reached in front of her and slipped his hand inside the waistband of her bottom, sliding his finger down until he split the taut fold of her pussy lips.

Stop that!” Kelli cried out, “What if someone sees?”

No one can see,” he murmured into her ear, flicking his tongue across the lobe quickly, “no one is nearby and we are under the water.”

Kelli moaned lowly as his finger circled her developing clit, a familiar tingle and warmth growing between her legs. As she pressed her cunt back against his finger, Bill slipped his other hand down her back and under the swimsuit to swirl a finger tip around her tight asshole.

Still cold?” Bill cooed into her ear as she pressed her body back against him, rotating her hips to maximize the touch of his finger on her clit and anus.

Not...not so,” she gasped, throwing her head back against his chest.

Bill took his hands out of her swim suit bottom and pushed his own suit down enough that the waistband hooked under his balls. Then he took Kelli's hand in his and placed it on his shriveled up dick before putting his fingers back on her clit and asshole.

What're so soft...and small?” she asked when she took his dick into her small hand.

It's the cold water, does that to a guy, just like it makes your nipples stiff,” he explained and started rubbing her clit a little faster. “I'll tell you what, we'll get out of the water after one of us makes the other one cum.”

I'll win that one today,” she grinned back at him, her entire body trembling when she clamped her legs around his hand and climaxed on his fingers.

Over the course of the summer, they went to the lake almost every day, always separating themselves from the other swimmers so they could play with each other until one or both of them would cum. As the water warmed, Bill would shoot his jism through her fingers into the water more often than Kelli but he would always make up for it when they got home, with his tongue and lips on her clit and a finger, and eventually more, in her ass.


One day towards the end of the summer, they were walking home from the beach in silence. Neither of them wanted to think about the fact Bill would soon be leaving for college on the other side of the country. Finally, as Bill fumbled with the lock on the door, Kelli asked a question that had been bothering her for a while.,

When are you going to fuck me...for real...not just with your fingers?” she exclaimed, looking at him defiantly with her arms crossed under her tits.

Bill turned and looked down at her, a bemused expression on his face.

You think that's something we should be talking about out here on the porch, for the neighbors to listen in...maybe you want to ask Mrs. Watson next door her opinion too?” he smirked and walked into the house.

Kelli blushed and hurriedly looked around before following him into the house. He dumped the bag with their wet towels in the laundry and got himself something to drink.

Well...when?” Kelli insisted, positioning herself directly in front of him as he sat on a stool at the kitchen counter, his dick stiffening as he considered his pouting step sister and her explicit request.

I told you a long time ago, I won't fuck you in your pussy. You need to save your cherry for your true love. Besides, I prefer ass play in any case.”

But...but...I love you,” Kelli whimpered, looking up at him with tears brimming in her eyes.

And I love you, too, but not that way and we can never be together. You know that,” he said kindly as her lips began to tremble.

Bill pulled her close, kissing her cheek and neck as she began to cry. Then he pushed her back enough he could look her in the eye.

I'll tell you what, how about we see if my hard dick can fit into your tight asshole,” he said softly, then scooped her up and carried her upstairs over his shoulder.

Kelli squealed in delight as he threw her down on her bed and unceremoniously ripped off her shorts and panties. As he pulled his own shorts down she took off her shirt and lay back with her legs spread wide. She knew he liked seeing her pussy gape open as much as watching her play with her clit.

Bill's cock was throbbing as he dropped to his knees and pushed her finger away from her taut pink slit with his tongue. Kelli pulled her legs back, giving him an unobstructed view and path to her tight little anus.

He looked up at her and grinned, his finger snaking toward that puckered asshole while he continued to lick her pussy and suck on her clit. Ever so slowly he gently pushed one finger into her. Kelli quickly relaxed, having learned from him before how to enjoy one finger filling her.

You OK?” he asked as the second knuckle penetrate her tight sphincter.

Oh...yes...more,” she hissed.

Ever so slowly, he began rotating his finger inside her asshole while at the same time pushing it in and out. He spit on her anus and with the tip of the first finger just barely inside her, added the second, pressing in deep until both fingers were as deep inside her as he could manage.

How's that?,” he murmured, “tell me if I'm hurting you.”

Oh feels good...don't stop,” Kelli gasped, surprised by the intensity of the pleasure surging through her young body.

Play with your clit,” he instructed her as he pulled his face back from her pussy so he could get a better look at what was happening. Kelli immediately started to rub her throbbing clit, her legs trembling as the first hints of the coming orgasm surged through her body.

Bill added a third finger, stretching her asshole much more than ever before. Kelli cried out as the third finger plunged into her and then started flailing her hips wildly, a massive orgasm engulfing her body. Bill just held his fingers inside her as she thrashed around on them, waiting until the initial wave faded.

More...more...please...more,” she screeched, rubbing her clit even harder as a second orgasm built even before the first completely faded.

He pulled her to the edge of the bed and pulled his fingers out of her ass, rubbing the throbbing tip of his cock up and down in her pussy slit even as she continued fingering her clit. He positioned his hard dick on her anus and pushed, trying to spread her sphincter by pulling her to him by her hips.

Her asshole was just too tight for his thick cock head to penetrate. Besides, he was so very close to cumming himself. Kelli squirmed around and Bill tried as best he could but he just couldn't slide his dick into her anus before he started cumming, rubbing his cock up and down in her slit as he sprayed his jism all over her belly and pussy.

Tomorrow we'll try again,” her muttered into her ear as they lay cuddling together for a few minutes, “I have an idea how to make it work.”

They heard her mother call up from the kitchen and quickly got out of bed. Bill grabbed his clothes and hurried to his room, turning back at the door to see Kelli scooping up his cum from her belly and pussy slit and licking her fingers clean.

The next day was gray and rainy, certainly not a day they could head for the beach, but just perfect for lazing around the house and finish getting Kelli's ass properly fucked for the first time. They both squirmed uncomfortably at the breakfast table, her mother seemingly taking forever to leave for work.

As soon as the door closed, Kelli jumped up and pulled off the panties she was wearing under a long, loose t-shirt. Bill put his hand on her arm and pushed her back into her chair.

Just hold on for a minute, in case she comes back for some reason,” he said with a wicked smile and picked up her panties, holding them to his nose while taking a deep breath.

You didn't wipe yourself very well this morning,” he sighed and took another deep whiff of the crotch of her panties.

I'll pee all over you if you want but first you have to fuck me!” she practically screamed at him, rising again from her chair.

Bill scooped her up and put her over his shoulder again as she squealed and squirmed, Her t-shirt rode up and he gave her a couple of playful slaps on her bare ass as he carried her upstairs, this time to his bedroom.

They both quickly stripped and Bill rummaged around in the nightstand drawer while Kelli lay on his bed fingering her clit. He pulled out a small jar and turned to Kelli.

What's that?” she asked as he unscrewed the lid and dipped a couple of fingers inside.

Vaseline,” he answered, “I use it to jerk off sometimes, makes my dick slipperier. Now get on your hands and knees with your ass in the air.”

Kelli did as she was told, lowering her head so her ass was raised facing him. She felt his fingers rubbing across her asshole, sliding easily into her with the gooey material covering them. He gently pushed one finger into her ass and she grunted slightly. The second and even the third went in easier and deeper than the day before.

Hmm, that feels good,” she cooed, pressing her hips back against his hand.

Bill spread the Vaseline all around her puckered ass hole and as far inside her as he could manage. She looked back when he pulled his fingers out of her and watched as he lathered up his rigid dick.

Ready?” he asked, as he dragged the head of his cock up and down in her pussy slit.

Oh it...please...fuck me,” she groaned and reached down to rub her clit, feeling his cock brush over her knuckles.

First he spread her ass cheeks with his hands, causing her tight puckered asshole to stand out, Then ever so gently he pressed the rigid head of his cock onto her anus. She gasped when just the tip penetrated the sphincter and he stopped for a moment.

Suddenly, he slipped deep into her bowels, filling her in a way she had never felt before. Her back arched and she cried out as he just held himself buried inside her.

Oh god...oh...oh god...that,” she shrieked and firmly pressed her ass back against his cock, “more...god more...harder...more!”

Ever so slowly, Bill began pumping his dick in and out of her asshole. Kelli shrieked and fingered herself to one orgasm after another, each time clamping her ass around his cock. Finally, he could hold back no longer. With one final deep thrust, he grunted his cum into her bowels then rammed his cock in and out of her as hard as he could until he final softened and slipped out of her.

Kelli knelt breathing heavily, a rivulet of his cum oozing from her asshole and down her thighs.

Are you OK?” Bill finally managed to ask when he again caught his breath.

His step sister pushed herself up on her elbows and grinned over at him before crawling up on his chest and ramming her tongue into his mouth. Bill could feel his cock stiffening as the kiss continued.

That was...amazing,” she cooed and kissed him again deeply. “I have never cum that good...on my fingers,,,or yours...or even your mouth.”

With that she reached down and fondled his cock, sliding down to lick his balls and slide a finger of her own into his ass. Bill's dick stiffened again and Kelli looked up at him with an impish grin.

Are you ready to fuck me in the ass again?” she moaned and rolled back on her hands and knees next to him.

The next time, her asshole was already stretched and her bowels coated with the Vaseline and his cum. Bill took his time, bringing her to at least two body spanning climaxes before once again filling her with his pasty jism. Afterward they lay cuddled together in the afterglow of their orgasms.

That felt so, so good,” she whispered into his ear, “if you promise to keep doing that to me, I'll do anything you want, anything at all.”

Bill grinned back at her, gave her another kiss and got off the bed. He reached down and took her hand then led her down the hall to the bathroom.

Now about that peeing all over me you mentioned....”


As the summer days drew to a close, neither one of them wanted to face or talk about the fact he was soon leaving for school. Their sex play became more manic, trying to get as much of each other as they could in the little time remaining.

Kelli insisted on getting ass fucked as often as he could manage. After a little experimentation, they settled on a favorite position where she would straddle his hips and lower herself down until his cock was buried as deep as possible in her ass. That way, he could twist and twirl her growing nipples while she could rub her own clit until she couldn't cum any longer.

The last day they were home alone, she cried even as he fucked her ass and she sucked his dick hard again. One last time, she begged him to fuck her in her pussy but once again, he refused.

That evening, Bill and his father loaded up all of his stuff in a small rental truck they would drive across country. After he was settled, his father would fly back home. That night, Kelli could hear her mother and step father's headboard softly banging against the wall in the bedroom down the hall. She just knew Bill was jerking off across the hall and so wanted to spend his last night in his bed, with his dick in her hand or ass. She fingered herself to an unsatisfying orgasm before falling asleep.

Two days after Bill and his father left, her mother took her out for a nice dinner at a good local restaurant. She tried to keep up a good front but Kelli really didn't feel much like celebrating her twelfth birthday.


Kelli stepped out of the Lyft car and took her bag from the driver. As he drove away, she looked around, the house and the entire neighborhood a bit more shabby than her last visit about two years before.

She climbed the steps and rang the bell, waiting patiently for a few moments until the door opened wide. Bill grinned down at her, a little thicker and a lot grayer than the last time she saw him. Then again, so was she.

Hi sis,” he grinned and threw his arms open wide, “it's been way too long.”

She melted into his arms, pulling him close, inhaling his musky scent as he snuggled against her neck. After a moment, he broke off the embrace and stepped aside so she could enter the house. Not much had changed inside either, just looking a bit more worn.

As Bill picked up her bag, another man walked in from the kitchen. He was short and slight and looked to be in his mid to late thirties.

Kelli, meet my husband, Chad,” Bill said putting his arm around the guy's shoulder, “and Chad, my step sister Kelli.”

They shook hands and exchanged pleasantries before moving into the kitchen. Bill dug some cold beers from the refrigerator after Kelli told them she didn't need anything to eat.

So what happened exactly, your message was a bit unclear,” she said to her step brother after taking a deep drink.

Apparently Dad had a massive heart attack at the grocery store. They kept him on life support until I could get here, but there was no hope of recovery. I am glad you could come, I still regret not being here for you when your mother passed two years ago.”

I understand,” Kelli said softly, “Dad told me you were out of the country.”

They talked for a few more minutes before she retired to her old bedroom and fell asleep quickly after a long day.

The next day was an wearying blur. The funeral service at her step father's church, followed by the procession to the cemetery and burial and then by an exhausting parade of nearly forgotten or completely unknown family friends and relatives she had no doubt she would never again see.

She flopped down on the couch with a beer as soon as the last visitor was gone. Bill came in and sat down next to her with a beer of his own.

Thanks again for coming and helping me get through all that,” he said, absentmindedly patting her thigh. “How long can you stay?”

A few days if you need me, I don't have anything pressing going on until the middle of next week.”

I do appreciate it,” Bill said tiredly, “Chad has to leave in the morning. I have an appointment with an attorney the day after tomorrow and I want to get this place cleaned out so I can sell it.”

OK, I'm at your service,” she said softly, kissed him on the cheek and headed to take a shower and then sleep.

She was drifting off to sleep when she heard a low thumping. It took her a second to recognize the headboard hitting the wall across the hall. Her brother and his husband were having sex and that thought brought back the memories of those times he fucked her in the ass and licked her pussy until she climaxed in that very same bed. Kelli's pussy twitched and she buried her face in a pillow when she began to cum almost as soon as she started rubbing her throbbing clit.

Over the next few days, they went through every drawer and closet in the house, separating all the stuff into that they would just throw away, give away or leave for the estate sale. Kelli was scheduled to leave at mid afternoon the next day as they sat among the boxes in the kitchen, drinking more beer.

I don't know how to thank you enough for all your help,” Bill said quietly, “I don't think I could have done all this alone.”

Kelli smiled and leaned back against the counter top drinking her beer. A devilish smile grew on her face before she turned to face her step brother.

There is something I would love you to do for me,” she murmured slyly, her bra less nipples stiffening beneath her t-shirt.

Sure, sis, anything you want,” he responded without looking up or noticing.

My legs are killing me. I want you to give me one of your world famous massages,” she murmured and put her hand on his thigh, “just like you used to do.”

Bill turned toward her with a surprised look on his face. Then he broke into a broad grin.

Sure, why not?” he said, “go get ready and I'll be there in a minute.”

Kelli smiled back at him and practically ran up the stairs. By the time he walked into her room with a bottle of lotion in his hand, she was laying on her stomach wearing just some filmy panties and a lacy bra. She shivered when he ran a fingertip up the bottom of one foot.

I see your ass has gotten a lot bigger since I last saw you like this,” he laughed and squirted some lotion on her leg.

Well I guess most of me has, as well as that belly of yours,” she retorted before letting out a soft moan when he squeezed one of her calves.

Touche,” he laughed, “so tell me, what have you been doing with yourself all these years.”

He worked his way very slowly up her right leg as she told him a very abbreviated version of her marriage and divorce and a bit about her current job. She moaned lowly when his hands almost reached the silky fabric of her panties, deeply massaging her upper thigh before returning to her other leg and repeating his movements.

Kelli felt her pussy clench as Bill worked his hands up her leg. When he stopped just short of her panties on her right leg, she ground her pussy into the sheet. By the time his hands reached the same spot on her left leg, she could feel some of her pussy juices drooling into the gusset of her panties.

Mmm, you are still really good at this,” she gasped and bit her lip, practically ready to cum if he touched her pussy lips. “Don't”

His hands moved up both sides of her hips, his fingers catching in the bottom edges of her panties and pulling them tightly into her ass crack and folds of her now very damp pussy. She squirmed a little, feeling the moist fabric pulling against her throbbing clit. He leaned forward to whisper in her ear, the hard outline of his dick pressing against her thigh.

Should I get these out of the way?” he murmured into her ear and gently snapped the elastic leg band of the panties.

Yes...oh god...yes,” she gasped, raising her hips for him to pull off her panties while pressing her thigh even harder against his rigid cock.

He slowly pulled them down, pausing momentarily when the fabric caught in the wet folds of her pussy lips. She heard him take a sharp intake of breath, spread her thighs even wider and looked back to see him holding her panties to his face, inhaling the scent of her sex with a slight hint of her piss.

Her step brother kept her panties over his nose and grinned down at her. That's when she saw how far out his rigid dick tented his briefs, the only thing he was wearing. He tossed the panties aside and reached down to undo the clasp of her bra. Kelli shrugged out of it as she rolled on her back with her legs spread wide on either side of her step brother.

Fair's fair,” she cooed, pinching here erect nipples as he looked down at her, the pink inner flesh of her pussy peeking out through her thin honey brown cunt hair.

He smiled back at her and without a word, slipped his briefs off, his thick dick popping straight out at her. He crept forward a little until her inner thighs pressed firmly against the outer skin of his, his purplish cock head mere inches from her throbbing pussy.

You know, you were the first, and actually the only, woman with whom I ever had a relationship.” he said softly, starting to stroke his hard dick.

I was a little girl then,” she responded and spread her pussy lips with her fingers until the hard nub of her clit popped out, “but now I'm all grown up.”

Kelli could see the conflict of lust and confusion play across his face, as well as the droplet of precum dribbling toward her hairy cunt. She reached up and cupped his balls, drawing the tip of his dick right up to the dripping edges of her pussy. She brushed the head between those lips a couple of times before looking up at him again.

You know, there's something I wanted you to do thirty odd years ago and I'm asking...hell I'm fucking again to do it right now!”

He looked down at her quizzically as his entire body quivered with her touch.

You can fuck me in the ass and we have until tomorrow afternoon to compare my asshole and blow job techniques to your husband's...but...right now...there's only one thing I want you to do...I've wanted you to do since I was eleven years old...cum inside my pussy!”

Kelli's first orgasm wracked her body even before his cock was buried all the way inside her cunt.



Kelli took the Fed Ex package from the delivery guy and sat at her kitchen table to open it. There was a copy of a letter from her step father's attorney to her step brother with a cashier's check clipped to it. Apparently this was the final settlement on the estate and, although she didn't much care, she was pleasantly surprised by the amount.

At the bottom of the letter, there was a hand scrawled note...”Open the envelope last.”

She turned the packaging over and dumped out a plain white business envelope. She looked at it for a second before tearing it open. It contained an airline ticket with another note in her step brother's handwriting pasted on the outside of the jacket. Her pussy clenched as she read the fateful five words.

Chad wants to watch too!”


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