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TABOO SEX STORIES

Aaron And Grans First Anal Adventure

Aaron And Grans First Anal Adventure

by strangedarstar
19 min read
4.55 (15900 views)
adultfiction
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This is the third installment in a collection of stories featuring the erotic adventures of Lenore and Aaron, a grandmother and her teenage grandson involved in a taboo relationship with one another. Each story is complete in itself and no overarching plot binds the stories together so it's not necessary to read them in any particular sequence. These pieces have minimal back story and character development. The focus is on the lewd and lurid details of the characters' sexual encounters, which are graphically described in explicit (and sometimes campy) language.

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Aaron & Gran's First Anal Adventure

For the better part of half an hour, Aaron heroically staved off orgasm as his grandmother mounted an attack centering on his massive body cannon with her lips, tongue, hands and enormous breasts. The eighteen-year-old's stoic resistance to her aggressive offensive frustrated Lenore but she had not yet used all the weapons in her erotic arsenal. Bringing her hand to her mouth, she lubricated her index finger with saliva and stealthfully pressed its tip into her grandson's vulnerable butt port. When her finger had invaded his orifice up to the second knuckle, she twisted and wiggled it in his tight tush trench while with her other hand, she furiously pumped his precum-oiled love-missile, aiming it towards her open mouth.

Aaron continued to struggle valiantly against her relentless onslaught but Lenore's determination and lubricious tactics finally overcame his defenses and forced him to the brink of defeat. His taut tailpipe clenched around Lenore's finger as the first blast of warm semen spurted from his cock. However, the conquest was not to be an easy one for the old woman. Lenore's primary objective had been to trigger the boy's climax, commandeer his salty load and consume it in its entirety. But, overwhelmed by the sheer volume and force of Aaron's jizz explosion, she found it necessary to lift her mouth off of his spasming flesh rocket and allow his seed to shoot randomly onto her face, neck and breasts as she held his gushing appendage between her sticky fingers. When the deluge dwindled, she hungrily returned his tool to her mouth and suckled it. Only after she was sure her grandson had surrendered every last drop of his thick man cream to her did the sixty-two-year-old debauchee feel she had grounds to claim victory and rest on her laurels.

"Well done, darling!" Lenore enthused after letting his drained cock drop from her semen-glazed lips. "You really demonstrated wonderful restraint and self-control there. I thought you'd never come!"

"Thanks, Gran," the pleased boy said. "I tried to hold out longer but, like, when you started fingering my butt hole, there was no way!"

"Yes, well, that's my secret weapon, don't you know?" Lenore said playfully. She raised her hand to her mouth, planted a theatrical kiss on the intrusive finger and winked at him. "Okay, dear, I do love the feel of your fresh cum on my skin but, to be frank, it becomes less lovely when it starts drying and getting all crusty so I'm going to go to the bathroom and clean myself up. I'll bring back a wet towel for you when I'm done."

"Alright, Gran, cool," the boy replied as his grandmother rose from the mattress and left the room. Grinning, he shook his long blonde hair from his face, lay back in the rumpled bed and relaxed, enjoying the warm post-orgasm afterglow and sense of contentment that suffused his slender but muscular, six-foot-two-inch frame.

A little more than two weeks earlier, Aaron and Lenore had shared their first taboo experience, a spontaneous and unexpected encounter that had surprised and delighted both of them. Since then, the pair had ravished each other's bodies on four separate occasions, each one more wanton and lascivious than the last. Lenore's sexual energy, total lack of inhibition and broad repertoire of erotic skills astonished Aaron as did the mad lust that her aging body stirred up in him.

Before Aaron entered into an intimate relationship with his grandmother, his male and female lovers had all been close to his own age and possessed youthful bodies that sharply contrasted his grandmother's form, which was undeniably a decade or two past its prime. She was a corpulent woman, seven inches shorter than Aaron but only fifteen pounds lighter. Her mammoth breasts drooped down to the two spare tires of fat encircling her belly and her big, pillowy buttocks had long ago lost their battle with gravity and cellulite. Lenore's short, thinning gray hair topped a round, slightly jowly face, and there were deep-set wrinkles at the corners of her brown eyes and full-lipped mouth.

But despite these obvious signs of aging and physical decline, Lenore's body ignited Aaron's teenage libido in ways that the taut, toned physiques of his young partners did not. Why her pudgy frame aroused him so intensely was a mystery to the teen, but he he had no wish to explore the enigma. He simply gave himself over to his passion for Lenore without question and intended to keep doing so as long as his grandmother lusted after him as much he lusted after her.

Lenore returned to the bedroom semen-free and holding a warm, damp towel in her hand. Kneeling beside Aaron on the bed, she tenderly washed his now soft cock and mopped up stray, tacky beads of sperm from his stomach, thighs and groin.

"That was totally amazing, Gran!" Aaron said as his grandmother tended to him. "I came so hard! Like, I really think that was the best blow job I've ever had! Seriously!"

"Really, dear?" Lenore said proudly. "Even better than blow jobs from your male lovers? If so, that's certainly a ringing endorsement! I've always understood that gay and bi men are much more skilled at fellatio than women."

"Yeah, that's what everyone says, I guess, and it makes sense, right?" Aaron replied. "I mean, guys know what other guys like and all that, and, yeah, I've had tons of excellent blow jobs from dudes. But, honestly, Gran, I really think the one you gave me just now was the most awesome ever!"

The boy's words brought a pleased smile to Lenore's face for reasons beyond simple flattery. She and her grandson had always enjoyed a close relationship. In fact, Aaron had been comfortable enough to reveal his bisexual proclivities to her before telling anyone else in his family. Still, the boy had never shared any of the intimate details of his sex life with her until this moment and although Lenore was curious, a sense of discretion and respect for his privacy kept her from raising the subject with him. Mentioning the blow jobs he had received from other males was Aaron's first specific reference to his sexual activities with men and Lenore felt emboldened to probe into this part of his life for the first time.

"Aaron," she said tentatively, "do you mind if I ask you something very personal? If you're not comfortable answering, that's fine. I don't want to pry."

"You can ask me anything, Gran," he replied earnestly. "I don't mind."

Lenore looked thoughtful for a moment as she considered the best way to frame her question.

"Well, dear," she said, "I'm just curious about what else you like to do with your boyfriends besides oral. Are there other things you enjoy doing with your lovers on a regular basis? Sexual activities, I mean."

"Definitely anal," the teen answered without hesitation. "Not always but usually, like, if there's time and we're in the right place for it and all that."

"I see," his grandmother said. "And, if I may ask, are you a top or bottom when you have anal sex? I can imagine you in either role. You love to fuck and you're marvelous at it but you also enjoy having your anus played with, so...well, I'm just wondering which role you most like to play with your boyfriends."

"I'm a switch so I like both," the boy responded. "Sometimes I'll be a top and sometimes a bottom. Sometimes if a dude is into it, I'll fuck him for awhile and then he'll fuck me and then maybe we'll even switch off again. We don't really plan it. It just kind of happens."

"That's fascinating, darling," Lenore said and went silent for a moment before continuing. "Let me ask you another question, if you don't mind. Do you enjoy anal sex with girls as much as you do with boys?"

Aaron shrugged. "I don't know, Gran. I've never done anal with a girl. They just aren't into it, at least none of the girls I've met."

"Really?" said Lenore, more than a little surprised. "You've never buggered a girl?"

"Uh, what's 'buggered', Gran?"

"Anal intercourse."

Aaron shook his head. "Nope, never. I've asked a few girls but they're like 'ewwww! Anal! No way!'"

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"What a shame! The poor things have no idea what they're missing. Anal sex can be so lovely."

Aaron gave his grandmother a puzzled look. "So...uh, does that mean that

you

like it, Gran?"

"Oh yes, I most certainly do, dear," Lenore replied. "Does that surprise you?"

"Ummm, well, I don't know. I just never thought...."

"You never thought your boring, old granny would enjoy anything as kinky as anal sex?" Lenore asked teasingly.

"No, no...uh...," Aaron stammered. "Well... actually, if I'm honest, yeah, sort of, I guess. I just didn't think old people were into kinky stuff like that."

Lenore laughed and gave her grandson a playful shove. "Oh you scamp! What a thing to say! Especially after what we did not ten minutes ago. You don't think getting a blow job from your grandmother qualifies as kinky?" She laughed again as she tousled the blushing boy's hair, and then continued in a more serious tone. "The fact is that I love being buggered, at least when it's done right."

"'Done right?'" the boy echoed. "I didn't know there was a right way or wrong way to do it. I just thought, you know, a dude lubes up his dick, puts it in the other person's butt and goes for it."

"Well, what I mean is the right way for

me

," she explained. "It's not necessarily the right way for everyone but it's the way I like to have it done to me."

"Ah, okay. I get you. So, uh, what

is

the right way for you, Gran?"

Lenore leered at her grandson and moved her rotund body closer to his.

"Well, it would be easier and more fun to show you rather than tell you, that is, if you're interested in sodomizing your wicked old grandma."

"Uh, sodom--what?" Aaron asked.

"

Sodomizing

me, darling. Screwing me in my bottom."

"Oh, right. Well, yeah, for sure I'd be into it. Totally! Like, do you mean right now?"

Lenore nodded. "I don't see why not, darling. We have time and your cock is getting hard again already." As they had talked, Lenore ran her fingers down over her grandson's flat belly to toy idly with his coiled member and loose ball sack. Although less than ten minutes had passed since the boy had filled his grandmother's mouth with a copious amount of semen, his teenage tool was well on its way to blooming to its full eight-and-a-half inch length under her touch.

"Definitely!" Aaron responded exuberantly. "Just tell me what to do, Gran. Usually I do it doggy style but is there another way you like more?"

"Doggy style, as you call it, is a wonderful way to start," Lenore said. "We can change positions as the spirit moves us. So dear, shall we get started?"

Aaron smiled and nodded his head. Lenore got on her knees and lay the side of her face against the sheet. Reaching back, she cupped and spread her hefty ass cheeks with short, stubby fingers tipped with ruby red fingernails. Aaron knelt behind her and looked down at the lewd display below him.

Lenore's stance gave Aaron a full view of the alluring topography of her crotch from her jutting pubic mound to the top of the crease dividing her butt cheeks. While the boy had seen his grandmother's furry, thick-lipped pussy close-up several times while pleasuring Lenore with his mouth, this perspective was new to him and it somehow made her vaginal bun seem even bigger and bulkier then usual. But it was the unimpeded sight of Lenore's anal knot that really grabbed the boy's attention. Until this moment, he had only caught brief glimpses of it, hidden as it usually was between her buttocks. Now with her cheeks spread, the old woman's anus was visible in all its unobscured glory and it fascinated the teenager.

Deeply etched striations radiated outwards from the center of her brown pucker like rays emanating from a sepia-toned star. A broad penumbra of mocha-hued skin surrounded the dark wrinkled disc, contrasting the chalky whiteness of her chunky, dimpled butt cheeks as did a small chocolate-coloured mole situated near the top of her ass crack. Sprigs of the gray pubic hair that carpeted her meaty pussy lips spread up across her taint and encircled the ridged ring of her tan booty hole.

The murky crease between his grandmother's buttocks and the wrinkled brown spot at its center sharply contrasted the smooth pink rosebuds and lily-white ass cracks of his male lovers. But the less-than-pristine state of his grandmother's butt cleavage did not repel the teenager. On the contrary, there was something about its sullied condition that made Aaron light-headed with lust, exciting him in the same way that the sight of Lenore's grizzled cunt and saggy, out-size breasts did: a debauched visceral response that made his cock throb and his brain teem with dark, primal urges.

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"Are you alright, sweetheart?" his grandmother asked, puzzled by the boy's silence. "Everything okay back there?"

"Uh, yeah, Gran," the boy answered, snapping out of his trance. "It's just, wow, your butt is so hot looking!"

"Ohhhh, thank you, darling!" the woman cooed. "What a sweet thing to say to your old grandmother."

"No, seriously, Gran. It totally slaps! So, uh, what should I do first?"

"Well, a little preliminary rimming for starters would be delightful," Lenore said. "But only if you're comfortable with that."

"Oh, for sure, Gran," Aaron replied eagerly. "I love to rim!"

The boy bent forward and lowered his head until his face was between her doughy ass cheeks. He wet his lips, planted a soggy kiss on his grandmother's pucker and then daubed at its surface with his flattened tongue. Her asshole had a slightly bitter but not unpleasant taste reminiscent of unsweetened chocolate. His adolescent male lovers were typically lax about their personal hygiene and their assholes and butt cracks often had a slightly feculent odor. But the only smell Aaron detected between Lenore's ass cheeks was the familiar, pungent scent wafting up from her aroused cunt. The boy had come to love this intoxicating fragrance, which always reminded him of raw, fresh seafood, and it acted on his senses like a potent aphrodisiac.

Aaron lapped away happily at his grandmother's dark knot, occasionally jabbing at it with his tongue. Soon her tight ring relaxed to the point that he was able to get the tip of his tongue into its center, a sign to both of them that her hole was ready for something larger.

"That's wonderful, dear," Lenore said to the boy. "Now, open the drawer of my bedside table. You'll see a jar of coconut oil that I use as anal lube. Take it out and get your fingers all nice and slippery with it."

"Sure, Gran," Aaron said as he lifted his mouth away from her dark star, now glistening with his saliva. He removed the jar from the drawer, unscrewed the lid and dipped his index finger into the white, gelatinous substance. When it was thoroughly coated with lube, he placed it against her still relaxed pucker and with one gentle but firm nudge, sank his finger into her up to the first knuckle.

"Oh my,

yesss,

darling," the old woman purred as his finger stimulated the nerve endings in her sphincter. "That's perfect. Now finger fuck my bottom and if you could put your penis into my pussy while you're doing it, that would be lovely."

The teen was only to happy to follow his grandmother's instructions. Gripping his shaft at its base, he guided his cockhead between her now very moist pussy lips as he slid his finger in and out of her ass. When he located her vaginal opening, he slowly pushed his cock into her. The sexagenarian's cunt sleeve had lost much of its tensile elasticity and was not as tight as it had been was but the immense bulk of Aaron's cock made for a snug fit and Lenore moaned as his man meat filled her.

"Feels soooo good, darling," Lenore said. "Now see if you can get two fingers up my bottom but be gentle."

Aaron pulled his digit from her hole and brought his index and middle fingers together as though mimicking a hand gun. He dipped them into the jar of lube, placed both fingertips against her sphincter and pushed them slowly into her anal entrance. Lenore sucked in a deep breath between gritted teeth and her entire body tensed as his fingers sunk into her.

"Oh yessss, darling, that's it," Lenore said. "Keep it nice and slow."

The teenager obeyed, gawking down at her butt crack as he slid his fingers in and out of her greased hole while simultaneously fucking her pussy. Soon, her sphincter had loosened its clutch on his fingers and was beginning to gape open.

"Okay, love," Lenore said, "I think my keester is ready for your cock. But remember, you're a big boy with a big penis and I haven't been corn-holed in a good, long while. Please be mindful of that and go slow."

The meaning of the words "corn-holed" and "keester" were unknown to the Gen Z teen but he intuitively understood his grandmother's request.

When he withdrew his tool from Lenore's pussy, it was well-wetted with her cunt brine. But to guarantee his grandmother's comfort, Aaron lubed his cock further with more coconut oil. After he had pulled his fingers out of her asshole, it contracted slightly but a small gap the size of a marble remained at its center. The boy placed the tip of his cock against this opening and paused.

"So, Gran," he asked, "should I, uh, just, like, push my dick into your butthole now or...?"

"No, no, dear," she said. "Hold it against my anus like that and I'll push back against you."

"Okay, Gran," Aaron said, gripping his cock in preparation.

Lenore took a deep breath, pulled her ass cheeks wider apart and eased her butt back against his cock. As the boy watched, the tiny gap at the center of her creamed asshole expanded under pressure and slid over his cockhead until the sinewy ring of her sphincter gripped the groove dividing his shaft from his cock's spongy helmet. When his entire knob was firmly lodged inside her, she paused and took a deep breath.

"Oh, sweetheart...that feels...

marvelous

," she said in a low voice. "Don't move. Just leave it like that and let me savour it."

The sight and sensation of his cockhead lodged in the pliant entrance to his grandmother's butt tunnel ramped up Aaron's libido to the point where he could barely keep himself from shoving his iron-hard member deep into Lenore's rear channel with one powerful thrust as he typically did with his male lovers. But he heeded his grandmother's words and resisted his wild urge. As always, he wanted to please Lenore and so controlled himself, remaining still and awaiting his grandmother's next instruction.

A moment passed before Lenore spoke again. "Okay, sweetheart," she said, "stay just like that so I can push back against you and take it up my bum at my own pace."

Bracing himself as Lenore pressed her ass against him, he watched the shaft of his engorged tool disappear into her hole. Soon the entire length of his rod was ensconced in his grandmother's gut corridor and his heavy ball sack bumped lightly against her paunchy pussy. Again the old woman paused and took a few deep breathes before reversing her motion, drawing away from Aaron's pelvis and exposing the slippery surface of his veiny tool as she did. When only Aaron's cock head remained in her ass, she stopped, exhaled and pushed back against him once again.

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