“The Cucumber Challenge”
“This morning I went to the local Walmart. I had to pick up some groceries for my Mom, and a few other things. As I was walking thru the produce I got a little tingle in my ass from looking at the cucumbers. You see, anytime I see something shaped like that, I always get that tingle. I have always been an “ass” girl. I lost my anal virginity before I lost my actual virginity. I’ve always had a fear of getting pregnant, so, I chose to get my ass fucked. I never looked at it as “gross”. I thought of it as a good way to show I care for someone. That’s all. I’m not a slut. I’ve only been with three guys, and I’m 18. Still in school, but, 18. They ALL had the pleasure of fucking my ass. After I tried it for the first time, there was NO going back. It was orgasmic. Something completely new to me at the time.
Now, I know just what to do, to bring myself to climax. Nobody knows you, better than you, know yourself, right? Hehe. My boyfriend, Cory, seems to get what turns me on, although he always surprises me with something, just to see how I will react. We like to role play, but I was thinking of pleasuring myself before I was going to see him later. I must of been horny when I spotted those cucumbers, because the first thing I thought of was “oh, those are pretty wide, I’m going to buy them”. I went and bought some k-y jelly, and the woman at the register just looked at me and smiled when she saw a couple groceries, makeup, ky jelly and a huge cucumber. I rushed home.
My parents weren’t home, and with no siblings, I had the whole house to myself. I was home alone. I rushed upstairs, and locked my door. It’s weird. I was getting all excited on the way home, I could feel myself getting wet thru my stretch pants, and I could feel my bumhole opening up, excited just as me, for what it was about to receive.
I love to lay on my bed and play with my ass, as if someone else was doing it, with my stretch pants still on. I don’t wear panties when I wear them because I don’t like having a panty line. As I was feeling and squeezing my asscheeks, and running my fingers up the crack of my ass, I could feel the bumps of my anus stuck to the inner side of my stretchies. I felt a small tear, just below my asshole. Dang, I just bought these, no wonder I felt a little draft up my ass. I was on my stomach with my legs spread. I know doing this was just opening up my ass. The hole was small enough that I wedged my finger into the hole and began to “dab” the inside of my hole with my finger tip. Dabbing the center of your asshole before you have any lube has a stickiness to it I was so turned on! I said hell with it, I wanted to be a little dirty, like I was getting manhandled, and I ripped my stretchies, right at my crack! Game was on.
I popped that cap off the ky warming gel, and stuck the tube in my ass, and squirted away. Uuhhll, I love that feeling of anything slippery in my ass. The more lubed, the better! I began to masterbate my ass. That’s a process of sliding my fingers in and out and doing motions, pressed circular motions giving ALL of my attention to my horny hole. It’s almost a mindset, closes then opens, closes and opens. Until you talk your ass into relaxing, and I swear you could probably fit anything you want up there.
I continued to smear my fingertips all around that region. Starting at the bottom of my pussy and moving my four fingers up the crack of my ass, spreading my cheeks with my pointer and ring fingers, while leaving my middle finger to smear my ass with, pushing all that love gel into my bum. At this point, I am hot. It’s take no prisoners! I grabbed my cucumber, and dripped a little bit when I noticed the size.
I couldn’t fit my hand around it. How was this thing going to fit up my ass! I took my hand with the gel on it and began to jackoff this 15” monster. I grabbed one of my shoes, put the cucumber in the sole, pointed straight upward. I had to put some blankets and pillows around it to balance. I looked at my ass one last time in the mirror behind me on my closet door. My ass is sooo tiny. I mean, a normal guy can just about cover my whole ass with his hand. My thighs are muscular, but not too much. I got up over top my friend, and eased it into my ass.
The first couple minutes I just did a series of small up and down motions, slowly spreading my sphincter with each little push. Finally, Oh my fucking God! It was in me. I could feel my anal muscles letting this thing in me. I kept sitting down, lower, and lower. I was about to cum just from entry! I slowly lowered my ass onto this beast as I could feel every little bump on the Cucumber. Once I thought I was down far enough, I eased back up, gritting my teeth with pain pleasure. Then back down.
I was just getting my ass used to the pattern of how I planned to destroy it. I started going up and down, still holding on to my friend. Up and down, oh the pleasure. I could feel it going past my belly button. Literally! I could see my stomach moving around in there. Making room for this monster. At this point I could feel that I no longer needed to hold on to it. It wasn’t going to come out of my shoe every time I went up any more. I let go.I was loose enough.
This is when the fun REALLY begins! Now, I could basically pound the shit out of my ass and that thing was going to remain right there, it’s own weight holding it down.
I wanted to feel it sliding in and out of the sides of my inner ass. Slam. Slam. Shit! Shit! It felt so fucking insanely good. Up, down, up, down! I was riding this thing with no abandon. I spread the sides of my tiny ass as I plunged down deeper going at an erratic speed. I could feel it! I could feel it! So fucking good! I could feel the sides of my shoe as I slammed down on this python. The sides of my shoe! I was that deep! That was now my bumper. My shoe.
I looked between my legs in disbelief. But, sure as shit, there was a k-y ring right at the level of my shoe. I was slamming my ass a good 12” into my ass! Incredible! I took it all in! Just by noticing this I couldn’t hold it anymore! I was a moaning mess, it felt so incredible. I gushed and squirted all over my bed while screaming, FUCK, MY FUCKING ASS! Up and down, slowing down, slipping myself off of my lover and collapsed on the bed. I put my hand in my ass and stirred it around. It was like satin. Beautiful. Soft. Warm. I wanted to stick my tongue in there. I wanted a cock in there. I sucked on my fingers as I lied there catching my breath.. whew. I couldn’t believe I handled that thing. I picked it up and was sucking on the warm end….and that’s when he came in holding his phone, obviously recording what I just did..My “brother” was obviously doing it from the door that was slightly opened. My heart rate started pounding in my head. “Oh shit! How did, ummm, “David” get there!? He wasn’t suppose to be home?!.”, I asked myself, I was so confused. I really lost track of time for him to be here already.
“Okay, Danielle, I got all the evidence I want. Now, I’m either going to post this video, or I’m going to fuck you.” David said. Here I was, just a girl masturbating, not hurting anyone, and my brother wants to have incest with me. I really had to weigh my options.
My “brother” was four years older than me. He should of moved out by now. He’s just lazy. Living off of Mom and Dad. We fought all the time. He’s just an immature loser, in my opinion.
“Well, I really don’t give a shit about what you choose. I’m sticking my dick in that ass” David said. I didn’t know what to do. I was naked. He pushed me down on the bed. He fumbled undoing his belt, and pulling down his pants to his thighs. “You’re such a dirty whore. Mom spoiled you, and raised a little slut, just like her.” David said kneeling down behind me taking out his hard cock.
Before I could say anything, he slid his cock into my ass. I gasped. Luckily I was already loose back there, or else it would of hurt like hell….. Just like many times before. David has been fucking me in my ass for years now. He liked to be as forceful as he could. He tried to scare me. Even though I secretly loved it. Sometimes he’d get out of hand and excited and stick his cock in my ass too fast, and it would really hurt.
David didn’t waste any time picking up speed and fucking the shit out of my back door. He had his weight on me, and I couldn’t move as he pumped deep and fast in my asshole. He had a pretty good size cock, and it felt so good against the walls of my colon.
My asshole was already a sloppy mess. Now, that’s all it sounded like while he thrusted deep and hard, slapping his full testicles off the bottom of my ass. I was getting hot, I wanted to play along in my own way, it felt so good.
“Fuck my ass! Fuck it! Fuck your little sister’s ass! Harder! I’m such a slut, I deserve to get fucked hard! Mmmm. How does the inside of my colon feel?! Your sister fucking loves your huge cock fucking the shit out of her ass!” I said as he really got turned on and picked up speed. His cock felt so good going in and out of my gaping backdoor. “I was thinking about this all day! My brother, fucking me. Shit!” I let out. It was such a naughty turn on. So taboo.
I was really enjoying this all too much, and I couldn’t help but break character. “Pound my slutty ass,…Cole..Fuck it! I love you baby! So much! You always know how to turn me on Cole baby..” Yes, it was “Cole”, my boyfriend. He came in my room role playing that he was my imaginary brother, “David”. It was a character we both liked a lot due to the complete dirtiness of brother and sister, fucking.
“Oh, baby, I’m going to cum! Where do you want it, Dani! Quick!” Cole said while he was sweating, and breathing heavy, pumping in and out of my gaping hole at lightning speed. “Anywhere, Baby!” I screamed out, just as Cole pulled his long cock out of my ass, and blow his initial load in my crack, just as I spread my cake. The hot semen felt so good on me. He shot the second, third, fourth, and others right into my bored out tunnel. I could feel it hit my inside walls. My asshole just swallowed his cum as it pulsated trying to close and open at the same time.
Oh, I loved it. Absolutely loved it. I stuck three fingers easily in there just to feel how open I was. So damn slutty. I love it. All of it… “
I hope you all liked this story. Of course it was a work of fiction. I feel I have to say that because I’m getting hit on by dudes, that don’t seem to read the whole thing. Anywho, if this story turned you on, I’d love to hear from you! I’ve only had two whole people comment, or send me a dm from the last story. I’d hate to think the novelty wore off. So, please, you give me the motivation to continue. And girls, you’re always welcome to send me an email! Thanks guys! I’ll have to see how this story is received, to see when I should post again. Love you all!
Source: reddit.com/r/eroticliterature/comments/d8w4zh/the_cucumber_challenge_mf_anal_implied_incest_long
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