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"I'd Love to Fuck Your Brother."
I swear she said that just to fuck with me. It is November, and it is already ass-butt cold outside. The trees are bare, and their branches creak and groan like the groping grasping hands of a blind old beggar lady. We are playing pool in the upstairs room of The Brewery. All I have to do is sink the eight-ball to win. I scratch.
Later, under a million cold hard stars, grasping the steering wheel with gloved hands and wishing that the heater would come on, her words came back to me. I'd heard the same thing, mostly not quite so bluntly from a lot of my girl friends and a few of my guy friends. But The Toad?
Okay, that is a terrible thing to call her, and even thinking it makes me a terrible person. I'd never ever say it aloud, but Jen, who's been my friend since the deep dark pit of despair that was junior high school looks like a toad: short, squat, with oversized lips and slightly bulgy eyes. Her hair is shoulder length, dishwater brown and limp; her bust is enormous and usually contained under something that looks a little like a gunny sack; and she looks out at the world through a pair of half inch thick horn rimmed glasses. Even though we had been friends forever, I had never heard Jen talk about guys or sex or crushes or dating or anything. I had assumed that she just wasn't interested.
"I'd jump Kaleb if I ever had the chance," she had said, finishing her beer. I bent over and pulled the back the cue, trying to concentrate on the shot "I'll bet he's got a pretty big dick."
I blew the shot. It was Jen's game. The bitch. "I've seen it," I said with an evil little smile, draining my own beer. "You're right, it's pretty big."
It takes a couple miles before the heater starts to kick in. I'm just glad the stupid car started in the first place. I've scraped a patch of frost off the inside of the windshield so that I can see to drive. Say what you like about Ohio, the winters are cold. No fooling.
I think about Kaleb, and try to picture him fucking The Toad. It makes me smile because I just can't see it. He is slender and good looking, with olive skin and far away eyes and the build of a long distance runner. He doesn't need this right now anyway; he's got problems of his own. He's moved back in to Mom's house at the ripe old age of twenty-eight, and is in the middle of getting a divorce. He got layed off from his corporate gig in Boston, and has been working swing shifts at a CD factory.
On second thought, maybe a good fuck is exactly what he does need.
The Toad and I are sitting on my old bed in my old bedroom, looking through our old high school yearbook. It has only been three years, but already the people in the pictures look strange, foreign, as if they came from another time, another place; the land of Disco in the realm of the Heartland. We are both amazed; there is no one there that we feel a thread of connection to anymore.
"So have you really?" we have been smoking a little pot, which makes free association seem natural, and everything a little more surreal.
"Really what?"
"You know—seen his dick?"
I have, in point of fact, seen Kaleb's dick twice. Once when I walked into the bathroom when he had just stepped out of the shower; and a second time when I had spied on him while he jerked off to a porno magazine.
"Well, does it make a difference?" Jen asked "If it's a big one or not?"
"Of course it makes a difference." I told her "But it doesn't necessarily make it any better."
I was about ninety percent sure that Jen was a virgin. Me, I had gotten rid of my virginity at the earliest possible opportunity. I had discovered that sex could be in turns awkward, embarrassing, uncomfortable or even painful; and then pleasurable, addictive, explosively orgasmic; and finally: a lot more fun with girls. It wasn't that I was a lesbian exactly; it was more like I was a vegetarian who occasionally indulged in a big juicy cheeseburger. Or something like that.
"So how would he do it to you?" I asked. .
"Oh I don't know..." she said "He'd take me out someplace nice for dinner... it would be romantic but not too fancy, and we'd have great conversation and drink some wine..."
The Toad had obviously thought this through.
"And then what would happen?"
"Oh you know" she blushed "He'd take me home and we'd... do it."
"Details girl! I want details!"
Jen was bright red. She hit me over the head with a pillow.
"Come on girl, spill it! I'd tell you." It was true. When I was first discovering my interest in girls, it was The Toad who got to hear all about my crushes, all my lusts, all in gory detail. I don't know what she'd made of my lesbian fantasies. 'Interesting idea' was all she would ever say.
"Well, the thing is I'm not very experienced." she said "So I don't know how it's really supposed to work. I mean, aside from the obvious."
Jen and I must make an odd pair, I thought. If I'm going to call her The Toad, I should really call myself The Stork. Where Jen was short and stocky, I was tall and gangly. And flat as a rail. With our glasses and our predilection for comfortable oversized sweaters and baggy pants, we must look like refugees from Geek Central. It didn't help that we were both heavily into scifi/fantasy; and computers. In high school, we had both been total outcasts. Fortunately, there is more to life than high school.
"I was thinking" Jen went on "Maybe you could help me practice."
Okay, now I was interested. I had never ever had a sexual feeling for The Toad. Hadn't even crossed my mind on hot summer nights as I lay sweating on top of the sheets, strumming my clit and picturing all the girls I knew or had ever seen, and what they would look like naked and between my legs, licking my drenched and sticky sex until I finally exploded and was able to drift off to sleep at long long last.
You know, Jen might not technically be very attractive, but she is a pretty fucking awesome human being.
"What exactly did you have in mind?" I asked
"I thought maybe" she was blushing again. It was pretty cute "You could teach me how to kiss... and stuff."
She's twenty one, and doesn't even know how to kiss. My heart melted for her.
"I could take Kaleb's part and we could go through the motions. Just for practice of course."
"Ok" she giggled. "Just for practice."
I leaned over and kissed her on the lips. It felt nice. Strange but nice. She pressed back against me, and I slipped my tongue into her mouth. Her tongue tentatively met mine. We kissed like that for a long time. She was a little hesitant and unsure, but enthusiastic and eager to learn.
"Oh Andrea"
"Call me Kaleb."
"Kaleb, I've never been kissed before. Not really. Not like that."
We kissed again, and my hand found her breast. It was warm and soft and huge. I found myself tugging up her sweater.
I struggled with the clasp of her bra. Damn those things! I finally got it loose, and her tits spilled forth into the bedroom. They didn't look like anything you'd see in a magazine or a video; and I wouldn't want to have to carry them around all day; but I loved losing myself in her soft pliable, asymmetric breasts, kissing and licking and nibbling all over what seemed like acres of brilliant white flesh. Her nipples were huge, in the middle of dark brown aureole, and rabidly erect. They just begged to be sucked on, and suck I did.
We struggled and tugged and got her skirt down around her ankles. I was still fully dressed, and horny as all fuck. My pussy was drooling into my panties, and just the pressure of her naked leg against my jeans-clad thigh was driving me insane.
She kicked her legs and suddenly she was lying on her back in front of me wearing nothing but her underwear. Garfield panties? I didn't know they even made those in adult sizes! I could see the swell of her sex, the suggestion of lips through the thin material. Garfield smirked at me from a yellow cotton background. The Toad arched her back, lifting her ass off the bed, and I pulled them straight off. Then I gasped out loud.
Her pussy was swollen and purple, crowned with a healthy triangle of brown hair, and her clit was peeking out like tiny little red penis straining to get out from under its little hood and up at my hungry tongue. I could already see her wetness, making a moist trail down the crack of her ass.
Her labia were pierced with half a dozen stainless steel barbells, sewing her pussy up tight as the bars of a high security jail cell.
"Oh my god Jen, who did this to you?"
"Mr. Silverman, our math teacher." she giggled self consciously "It was his graduation present for me. We were together our whole senor year. I wanted to tell you, but I was afraid of getting him fired."
"I thought you were a virgin! It sounds like you've got some experience under your belt."
"Well we didn't do anything technically sexual together."
"Do tell."
"He used to put clothespins on my nipples and spank me with a ruler and make me masturbate in front of him. Sometimes he would have me put a vibrator up my butt. Then he would, you know, jerk off onto me."
"Jen, why?"
"Well 'cause I asked him to, silly!"
"But your pussy!"
She smiled "Oh I can take those out any time I want to, for the right guy. I just haven't yet. And I still have full access to my clit."
Wow. The universe had just shifted on its axis.
"Kaleb" she said with a shy smile "I think I'd like to see you naked now."
I took off my clothes as if in a trance. I could physically feel her eyes roving over my body, exploring me hungrily as I peeled off shirt and bra, stepped out of my jeans. I felt myself blush. I felt vulnerable and exposed standing naked in front of her as she looked me up and down.
We kissed again. Her skin felt awesome pressed against mine. Irresistibly, I slid down her body, pausing briefly to visit her huge tits, exploring the tender bulge of her tummy, her deep set navel, finally reaching my goal, the damp flame of her cunt.
I could feel the heat radiating off of her. If her clit got any more swollen, it might pop. I closed my eyes and stuck out my tongue, and traced the steel-laced length of her labia. She was hot and wet and salty. I could feel each one of the barbells underneath my tongue.
"Oh Kaleb, Yes! My clit!"
I couldn't stand to torture her any more. I stuck my tongue out and found her red hot button. She went crazy, like an attention starved cat while you are trying to read a book: arching up and rubbing herself on my face, purring and moaning and writhing sexily on the bed. She was wet, and I was covered in her juice. I clasped her buttocks (surprisingly small and firm) in my hands and drew her to me, licking and sucking until my tongue ached and her body shook.
"Oh My God" her slightly bulging eyes were wide open and there was a huge grin on her face. "Kaleb you are incredible! Let me suck your cock!"
I got up and opened my sock drawer and retrieved Pinky, my current favorite. It was large and realistically shaped, bright pink with sparkles.
"No" she said, pointing between my legs at my drooling sex "I want your cock in my mouth."
Well it had never been put to me quite that way before, but I was game to play. I knelt over her face, offering her my freshly trimmed, soaking wet and slippery, desperately horny pussy.
Well, maybe Toad isn't such a bad name for her: she's got a tongue that's about six feet long. For someone who'd never licked pussy before, she wasted no time diving into my cunt. She was slurping up and down my slit, stuffing my hungry pussy full of her thick fingers, tantalizing my clit and teasing the super sensitive skin around my asshole.
"Oh Kaleb" she moaned from between my thighs "Please fuck me now!"
I looked down at her cunt, locked tight with surgical steel.
"In my ass" she said, looking up from below my mons "Please fuck me in the ass."
She didn't have to ask me twice! I lifted up her legs, exposing her cute little ass. Her cheeks parted naturally, showing me her wrinkled brown anus.
I couldn't help myself: I lowered my face to her crack and rimmed her vigorously, probing her asshole with my tongue, delighting in her earthy musk, the tightness of her hole, the raw sexuality of the moment.
She giggled and squirmed and buried her face in my snatch.
"Fuck me now Kaleb, please fuck my ass!" her voice was muffled by my pussy on her mouth.
Her asshole winked hungrily. I wet Pinky with my own juice, reveling in the low level buzz that transmitted all the way to the root of my clit. Then I pressed the head of the vibrator against her little opening.
She opened right up, and the tip of the cock slipped effortlessly in.
"Yes Kaleb Oh Yes! I'm so horny! Shove that cock right up my asshole!"
I started out gently, not wanting to hurt her, but the slower I went, the more she begged. Finally I had all seven inches buried in her tight backside, and she was writhing around, pleading with me to fuck her ass hard.
I slid Pinky in and out, fucking her faster and faster, really getting into it. I loved fucking her ass. I kept bumping her swollen clit with my thumb when I pressed the cock up inside her. Her cunt was soaked. Her barbells were covered in joy juice, and gleamed in the bedroom light. She had fingers up my pussy, fingers up my asshole, fingers on my clit, and she was going to make me fucking come all over her.
"OH YES KALEB!" We didn't have any close neighbors, and Mom worked nights at the hospital. Thank god. "YOUR COCK FEELS SO GOOD UP MY ASS! OH KALEB! FUCK ME! OH YEAH I'M GOING TO COME!"
We somehow managed to orgasm together, writhing and licking and fucking in one slippery, sticky, salty, wet knot. I ground my cunt all over her face, riding waves of pleasure, not really caring if she could breathe or not as I fucked her ass without mercy and flogged her clit with my tongue. I don't know how long it lasted. She kept calling out Kaleb's name. Her body shook, her stomach convulsed again and again. At her peak, she let go with a little stream of pee that caught me right in the face. I drank her eagerly, tasting her salty essence. At long last, we collapsed together onto the bed.
We cuddled together, enjoying being close, kissing and petting softly. When I finally looked up, I was startled to see my brother Kaleb standing in the light of the half open doorway. I sat bolt upright. Jen lay paralyzed where she was.
He cleared his throat. "I thought I heard someone call my name."
We all three laughed until it hurt.
Just a great story idea that is well written. Original idea with real people. Liked the touch with the brother at the end. Could we see a redux from the brother's point of view and a continuation?
You are just plain, flat-out my favorite writer on this site. I'm really glad I discovered your stories. Made for fun reading on a few days away from work for me.
Nice story about characters that aren't the type that dominate this site. I much prefer reading about people that seem real instead of the Lit stereotypes. Well done.
Very sweet, innocent, and erotic, with an opening for the other story. Get back to work, my dear ... you have more work to do, and I just know it will be a great story.