Grandmother's Remorse

In the sleepy little village of Newport, New York, there was one resident who was still awake as the sun rose on Sunday morning. Eleanor Bartlett had dropped off a couple of times during the night, but only for a few minutes of what could best be termed fitful sleep.

At 63, Eleanor didn't usually sleep that well anyway, witch is why she had begun taking sleep medication. She had meant to take a half of an Ambien last night, but hadn't because things had gotten a little crazy.

A little crazy. Eleanor smiled to herself when that thought crossed her mind, because what had happened wasn't just a little crazy.

The fact that she body ached from head to toe didn't help her sleep any either, Eleanor noted, as it seemed like every joint and muscle was on fire, especially areas that hadn't bothered her in years.

Eleanor knew she had to get up and go to the bathroom, something that she had put off for about as long as she could because the thought of taking that short stroll down the hall make her ache all the more. A woman who outdid her peers at the senior center's treadmills and stationary bikes could only imagine how she would feel if she wasn't in decent shape before last night.

Last night. Eleanor's eyes left the ceiling where they had been fixed and over to her side, where the person responsible for everything she was feeling was sleeping quite soundly, the boy apparently not burdened with the guilt and aches like she was.

That wasn't quite right, Eleanor thought as she looked at the naked lad with his arms and legs akimbo, almost fully exposed because the sheet that had covered them both was down to their knees. The boy wasn't responsible, or at least wasn't the main culprit, because as an adult Eleanor could have stopped it at any time, but hadn't.

An 19 year old boy - or man as she kept telling her - couldn't be expected to harness his raging sexual desires, and had just done what comes naturally. What was her excuse, Eleanor mused? Insanity? Senility? The need to be with a man again? The idea that a 19 year old boy could find her attractive and want to make love to her?

Probably all of the above, Eleanor concluded as she raised herself up on her elbow and prepared to get up, but that didn't make it right. She imagined telling the other old biddies about it at Bingo. Most wouldn't believe it, of course, but the ones that did would be envious as all get out because they were either alone or with husbands who were useless between the sheets.

So Eleanor knew that she would never be able to tell anybody about what had happened last night, not even her priest. Not in this little town, Eleanor concluded. It seemed everybody knew everyone's business around here, and the thought of having the world knowing what had taken place in this bedroom would make her a pariah around here.

Not the part about an old widowed lady having sex, because while what she had done wasn't moral, times had changed, and the fact that a woman was over three times the lover's age wouldn't subject Eleanor to scorn, because the boy was of legal age.

It was the other part. THAT was the sticking point, because even in the 21st century when morals had gone to hell in a hand-basket, society still frowned on the idea of a grandmother having sex with her grandson.

***

Timmy was a beautiful boy though, Eleanor thought as she looked over at her grandson, the picture of innocence as he snored ever-so-lightly. He didn't look all that different now that he had while growing up, and would probably be one of those fellows that always has boyish look about him even when he got older, like Dick Clark had for so long.

Timmy's fine blond hair was a mess as it stood out against the pink pillowcase his head rested on. Little fella probably didn't even shave yet, Eleanor noted as she looked at his rosy cheeks before her eyes went lower.

Lovely white skin, with only the faint memory of the tan he had last summer, and flawless too, except for the bruise Timmy had on his collarbone. I did that, Eleanor recalled, grimacing as she recalled how she had bit into her grandson while in the midst of a bone-rattling orgasm.

A little spray of golden hairs that were nestled in the hollow of his armpit was the only hint above Timmy's waist that the man was no longer a boy, as his chest was smooth. He could stand to gain a little weight, Eleanor thought, although the whole family had always seemed to be slightly built.

The boyishness ended abruptly the further down Eleanor's eyes went, and even now at rest the sight of Timmy's manhood was startling to her. Not as shocking as it had been last night when he was engorged and angry looking, Eleanor remembered, but still an amazing sight and certainly not what she had been expecting.

Timmy's penis was a stark contrast to the rest of him, and even now as the flaccid organ rested over to his hip just below the little nest of hair, Eleanor couldn't get over the size of it. Below that, Timmy's wrinkled scrotum with the egg-sized testicles hung down to the bedding, an equally impressive set.

Eleanor hadn't been with all that many men, she mused as she kept staring at her grandson's private parts. Only a couple before she met the love of his life, rest his soul, and only one regrettable man after her beloved husband passed seven years ago.

None of them, even her late husband who had been pretty well endowed himself, were built anything like Timmy was. Eleanor sighed as she looked at the pink bulbous head of his manhood, remembering last night how crimson and angry it had looked when he was bringing it down between her legs that first time.

And it was like the first time, Eleanor recalled as her insides reminded her of what Timmy had felt like when he first tried to put that massive organ inside of her. It was exactly like what it had felt like in that barn with Wally Monroe over 45 years ago.

It was probably a combination of things, not the least of which was her nervousness, even though she not only did not resist her grandson when he came on to her but had encouraged it in the time leading up to it.

Timmy could have been a little more patient at first, and gotten her ready for what was going to happen, but that was the part that excited Eleanor the most. The wild look in her grandson's eyes, the lust and the desire that had the air around them crackling with excitement, was part of what had made it so good.

***

Eleanor finally forced herself to get off of the bed, and with as much discomfort as she had suspected she would feel, managed to waddle into the bathroom to sit down and relieve herself.

Letting the torrent of pee, along with what had to be a copious amount of Timmy's semen, blast into the bowl, Eleanor tried to remember how many times they had made love last night.

She remembered at least three times enjoying the sensation of feeling Timmy's huge penis spurting her seed deep inside her, but it might have even been four. It seemed that once he started, Timmy was always hard, or on the way to being erect. Such a virile young man, Eleanor sighed as she gingerly wiped her sensitive area before flushing and washing her hands.

In front of her, Eleanor looked at the image in the mirror and had to laugh. How a young man could find her attractive was beyond her comprehension. Her short silver hair was a mess, and Eleanor grabbed a brush to try to get it into some kind of order in case Timmy was awake when she got back to bed.

Her eyes were red and she looked like she hadn't slept a wink, which was pretty close to the truth. Eleanor crinkled her nose at the sight as she fought her unruly hair with the brush, and just then she glanced down at her upraised arm and made a face before setting down the brush and grabbing a razor out of the medicine cabinet.

Eleanor made quick work of the little wisps of light brown hairs nestled in the deep hollows of her armpits, recalling how embarrassed she had been when in the midst of one of the lovemaking sessions Timmy had pinned down her wrists and kissed his way up the insides of her arms and right into her underarms, which she had never bothered grooming in recent times. Timmy hadn't seemed to mind though.

Who would have thought, Eleanor mused as she shook her head and grinned. Her hands came up and cupped her breasts, squeezing the little orbs which had gone from being perky to sagging with the passage of time, and as she gently kneaded them she remembered Timmy's maniacal eyes while he had mauled them like an animal.

You should have seen them back in the day, Eleanor thought as she looked at what she had done to her nipples by playing with herself, the dusty rose pegs sticking way out and throbbing again at the thought of the boy's hands on them.

Her hand went down to the triangle of pubic hair between her legs, and when she felt the stiff hairs that had been saturated with Timmy's semen she wanted to get into the shower and get clean, but didn't want to wake up the boy so instead just went back to bed.

***

Eleanor tiptoed over to the window to close the curtains as the sun started rising in earnest, and although that darkened the room quite a bit, she could still see clearly when she eased down next to her grandson who was still sound asleep.

When Eleanor got into the bed, she didn't go back up where she had been up next to Timmy, but instead curled up by his hip, her face just a few inches from Timmy's private parts as she stared at his treasures hanging in that wrinkled pouch.

Timmy's testicles were like eggs, with once being a small and the other one a medium, or maybe even a large. Too big to suck on very well, Eleanor recalled, especially the left one, and they were heavy too when they had started bouncing against her chin and throat during that time when she had gotten a little crazy.

I wonder if Timmy will remember that, Eleanor thought, and then shook her head and smiled. Not likely you forget your grandmother doing something like that, she concluded, and even now she couldn't believe she had done it. She hadn't thought about it in years, and it was something she used to do for her husband. All of a sudden, her tongue had gone from her grandson's scrotum, along the ridge of skin below, and right up to that tiny puckered hole.

She could tell that Timmy had been shocked, but he sure got hard right away when she licked that little honey pot, Eleanor thought as she fought back a giggle, although in doing that she had put another thought into her grandson's mind. She hated to say no to the lad, but he was so big that she was having trouble taking him in her vagina. The other place? She couldn't.

And there it was. Eleanor's hand reached over and took Timmy's penis in her hand, trying not to wake him. Even flaccid, his manhood was so big that her wrinkled hand only covered half of its length. Aroused like it had been last night, she had been able to wrap both hands around the shaft and still it was all she could do to take the rest of him into her mouth.

Eleanor leaned over and touched the opening of his penis with her tongue, sliding the tip along the pee-hole and down into the cleft at the underside of the glans, which was as fat as a plum. His member twitched in her grasp, and then she was moving her mouth over the bulb.

You're going to wake him up, Eleanor thought as she sucked on the bulbous crown, her tongue swirling around while in her hand she could feel Timmy start to get hard. But that's what you want isn't it?

Eleanor looked up and saw Timmy smiling at her, and as he ran his hand over her shoulder she said, "Thought I was having a dream."

"You are honey," Eleanor sighed after taking her grandson's now fully engorged cock out of her mouth long enough to speak. "Close your eyes."

"No way," Timmy said, and then Eleanor felt her grandson trying to move her over on top of him.

"Honey, I'm all messy," she complained, but by then Timmy had pulled her on top of his face, and after she felt his tongue lapping away as her sore passage she gave in and went back to sucking his penis.

Eleanor's mouth bobbed up and down on the half of his organ that she could swallow, while her hands squeezed his balls and the shaft of his cock. Down below, what Timmy's tongue lacked in experience he more than made up for with enthusiasm, making her tingle with each swipe of his tongue.

Then, before she knew what was happening, Eleanor found herself spinning around and down onto her back, her grandson handling her slender torso like a rag doll, and there he was leering down at her, his weapon in hand.

"Easy honey. Please," Eleanor begged, wanting to say that she was too sore but unable to say no. "I'm sore down there, and you're so big."

"I will be Gram," Timmy said, and to Eleanor's relief he was just that, slowly working his massive manhood into her with slight little movements while holding himself up over him. "You like my big dick?"

"Yes baby."

"Eric's is bigger," Timmy said.

"What?" Eleanor said, wincing as more of her grandson's cock sank into her, but Timmy's mention of his younger brother distracted her from the discomfort.

"Yeah," Timmy said as he watched his grandmother's reaction. "He's got more than 9". His cock is at least an inch longer than mine, maybe more."

"Oh dear," Eleanor sighed as she gripped her grandson's arms, unable to comprehend was she was hearing.

"Yeah, he likes to tease me about it too," Timmy said while undulating his hips. "Mine is way thicker though. We talk about you a lot."

"You do?"

"Yeah," Timmy said with a smile. "One time we were talking about teachers and which ones we wanted to do, and then he asked me what older woman I wanted the most, and I said you. Then he said that he was going to say that too but was embarrassed because he thought I would make fun of him."

"Oh dear," was all Eleanor could say as Timmy kept moving in and out of her.

"This gets you hot, doesn't it Grandma?" Timmy suggested, and even though Eleanor shook her head Timmy continued. "Us thinking all this time about how hot you are? About wanting to have sex with you?"

"No."

"Imagine this Grandma," Timmy said as he began to move his hips a little faster and harder. "I could be on my back, like I was that time last night, and you could be straddling my cock. The way your wild banana boobs hang down when you're like that makes me want to cum just thinking about it."

"Timmy..."

"While you were riding my cock I would be squeezing your tits - hard like you kept telling me you like it - and then Eric would climb behind you."

"Please..."

"He would have had your anus lubed up real good, and he'd have all 9 inches of that skinny snake of his greased up too," Timmy cackled as he thrust harder and faster still. "It would hurt at first when he stuck that pole up in you, and I've heard that guys can feel each other when the DP a woman."

"Omigod!"

"But you would like it, and then you would be begging us to go harder and faster!" Timmy practically screamed as their bodies slapped together loudly. "And then you'd cum - wouldn't you Grandma?"

"YES!!!" Eleanor screamed as her body convulsed, clawing at Timmy's shoulders while her orgasm kept rolling over her.

Timmy watched his grandmother's body continue to jerk around in the bedding as he pulled his cock out of her pussy, and after reaching over to grab his phone from the night table, knee-walked up to Grandma's face and finished himself off by hand.

"Ah!" Timmy groaned as he squeezed his cock with his right hand, positioning the crimson glans inches away from his grandmother's mouth to allow most of the milky white seed to spurt into her mouth while the rest spattered on her cheek.

With her head tilted back and her eyes closed, she missed Timmy taking more photos for his collection, and although she was confused about what was happening, she let her grandson ejaculate into her mouth, savoring the musky nectar as it rolled down her throat.

***

"You were just kidding about Eric, weren't you honey?" Eleanor asked innocently as they lay in bed together afterward.

"About him having a bigger cock than me?" Timmy asked. "No, it's true. He does."

"No, I meant about you boys talking about - you know - with me?"

"No, we talk about it all the time."

"But Eric, he's just a child," Eleanor protested.

"You won't say that when you see his dick," Timmy said with a laugh. "And he isn't a kid. He'll be 18 in a couple of months."

"That's right," Eleanor mumbled to herself, forgetting that the babies whose diapers she had changed were now young men. "But I could never..."

"Eric will shit when he sees these," Timmy said, showing his grandmother his phone.

"What?" Eleanor asked, fumbling to get her glasses, and when she saw the picture of her laying there with Timmy's penis shooting into her mouth her eyes bugged out. "When did you take these?"

"All the time we were doing stuff. It's called multi-tasking," Timmy cackled, letting Grandma see the photos he had taken.

"Oh no!" Eleanor gasped, with each picture seeming to be worse than the one before.

Photos of her giving oral sex to Timmy, of her looking like a lunatic while riding her grandson, and even a close up picture of her with her legs spread, her vagina and anus fully exposed and dripping with Timmy's saliva.

You're not going to show those to people, are you?" Eleanor asked - begged. "Please don't."

"I'm not going to show them to anybody except Eric, Grandma. I swear," Timmy said. "He'll never believe me otherwise."

"But I'm your grandmother," Eleanor said.

"Everybody does it. Hell, we've got a friend that's been doing his Mom for years," Timmy proclaimed. "We don't want to do our Mom though. We want you."

"What have I done?" Eleanor whispered to herself as she thought of anybody seeing her, a 63 year old woman engaged in sex with her grandson.

"On Eric's birthday we're both going to come out here," Timmy said. "What's better is that he's a virgin. He's been saving himself for you. Where are you going, Gram?"

***

Alone in the bathroom, Eleanor Bartlett leaned against the door, her head up against the wood, frozen in the position right where she had been for the last half hour or so.

"What have I gotten myself into," Eleanor said aloud.

Was this blackmail? Extortion? What could these boys want of her, a woman who has so little?

They wanted her, Eleanor thought. For whatever reason they wanted her broken down and aging body. It was sick and disgusting and also made her tingle, because she was just as bad.

The thought of her two grandsons impaling her with their enormous organs had made her orgasm so hard back in the bed that she almost passed out, and as her hand went down between her legs and began toying with her clit, she knew that she would do it when the time came.

On Eric's birthday she would let them have their way with her. They could stick their gigantic cocks into every orifice she had, and she would take it, because she loved her boys and would do anything to make them happy. The fact that having been reacquainted with the joy of sex made her happy as well only added to the thrill.

***

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