Ever since she was little, Heidi loved playing in the leaves. Shortly after her mom moved into the first floor apartment in the brownstone I owned down the street, the girl was out in the yard while I was raking, jumping in the big pile of leaves and squealing with delight while she scattered them all about.
"Heidi!" her mom shouted. "Get back over here! You're interfering with John's raking!"
I chuckled. "Oh, it's OK," I said, leaning on my rake. "Just look at how much fun she's having!"
Heidi's mom was a fine-looking woman, trim and athletic and pleasantly womanly in the right places. From the first moment I'd met her I'd been interested in more than just a landlord-tenant relationship and she was not entirely averse to the idea herself. But the few dates we'd gone on over the years had been unproductive, at least in the sense of a long-term sexual relationship. But, a friendship of a sort had blossomed and this allowed me to be quite close with her daughter as well.
After the first time Heidi trashed my leaf pile I went to the hardware store and got her a little kid's rake of her own and she loved working in the yard with me.
As the years went by, Heidi never stopped loving to play in the leaves. By the time she was nine, she'd grown into quite an adorable young lady. Her finest feature was her smile, which lit up her soft face so sweetly. She always seemed to have a big smile whenever she saw me, her dark eyes twinkling with merriment. She was not a particularly tall girl, and she still retained a bit of her "baby fat," but she carried it well--particularly on her backside. The girl had a wonderfully full bottom that stood out provocatively above her sturdy legs and I could swear she loved to show it off to me, wearing tight little shorts that revealed an unladylike amount of skin, or sometimes, if I was really lucky, she'd wear her favorite miniskirt, tiny and pink and held aloft by her girlish ass, providing the occasional little peek at her panties underneath. That sweet little ass was the subject of many late-night fantasies of mine.
It was a fine autumn day, warm and sunny, when I suggested to her mother that we should have a picnic at a little park I knew out in the country. I'd just been there to do a bit of carpentry, and I'd noticed that the whole place was covered in fallen leaves. "You know how much the girl loves to play in leaves," I said to her mom.
"Oh," her mom said, "I have to work. It's too bad, Heidi would love it!"
"Well, I'd be happy to take her there myself, if it's OK with you."
"Of course, John! She'll be so happy!"
Heidi and I packed our lunch and saw her mom off to work, and then Heidi ran upstairs to change. I was quite pleased to see that she put on her sweet little pink miniskirt. I'd have plenty of opportunity to look at her little panty-clad bottom while we were playing in the leaves!
The park was deserted when we got there. I had the impression that very few people ever went to this little place. She and I lugged our picnic gear and a couple of rakes to a spot as far away from the parking lot as possible, off through the woods and into a nice little clearing that was completely covered in leaves. Heidi wasn't interested in lunch at all, she just wanted to start playing in the leaves, so we raked a bunch up into a big huge pile and she started jumping into it, and then I joined in the fun.
Like I said, it was a warm and sunny day and pretty soon I was getting sweaty and feeling quite hot, and I pulled my shirt off.
"No fair!" Heidi said.
"Huh?"
"No fair! You get to have your shirt off but I don't!"
"Hey, I don't care if you want to take yours off. Nobody else is going to be coming around here, if that's what worries you."
She gave a big smile, then pulled her shirt off, too.
I hadn't seen little Heidi topless since she was five years old, and the sight of her adorable nine year old nipples caused a stirring in my loins. She was still flat and undeveloped, but I could tell that her nipples were standing up a bit from her chest, the light-pink flesh puffing out and a tiny, pale button of a stiff little nub in the center of each.
She saw me staring and giggled, then dove into the pile of leaves.
We frolicked together for quite a while, throwing leaves in the air, burying each other, and wrestling in the pile. I got plenty of wonderful looks at her little white cotton panties as her miniskirt lifted above her ass and I had a raging hard-on pretty much the whole time. And she knew it; she was obviously making a point of brushing up against my cock whenever she had a chance.
At one point she wrestled me over onto my back and climbed on top of me, her miniskirt pulled up, and she sat back, pressing her pussy through her panties hard against my cock. She gave me a little smile and then slid up, dragging her sex up my cock until she reached my head. I got the impression that the girl really didn't know or realize what she was doing. It was just a bit of unintentional sexual play, and she slid back down again.
She had a big smile on her face as she slid up and down again, and again. Then she slid up until my head was pushing against her sex, and she lay down on me, resting the side of her face on my chest, and she ground her little pussy into my head.
I reached down and put my hands on her bottom, guiding her movements a bit, and then I slipped my fingers under the elastic of her panties and onto the bare flesh of her ass.
As she continued gently rubbing her pussy against my cockhead, I moved my fingers down, one hand holding her open, the other hand finding her anus, my fingers passing softly over it. She made a sweet little moaning sound as my fingers gently caressed her little hole.
Still holding her open with one hand, I started circling my index finger over her anus, gradually pressing against it. As I massaged her, she increased the intensity of her motions, rubbing her pussy faster and harder over my head. I could feel her breath getting short.
And then I pushed my finger into her anus, just a little, not even up to the first knuckle. It was warm inside her, and her muscle was clamping tight around my finger.
She lifted her head and put her chin on my sternum, looking up at me. "You put your finger in my bottom," she said.
"Yeah," I said, "just a little. Is it OK?"
She nodded, still rubbing hard against my cockhead.
"Good," I said. I started moving the finger in a little circle, trying to loosen and stretch the tight muscle. She put the side of her face on my chest again and let out a little moan.
After stretching her for a little while, I whispered, "I'm going to try to put another finger in, OK?"
"OK," she said softly.
Her body stiffened and she took a sharp breath as I pushed my middle finger in.
"Does it hurt?" I asked her gently.
"A little," she answered.
"Just let yourself loosen." I could feel the muscle let up a little bit. "Yeah, like that," I said. And then I started moving my fingers up and down, just a little, very gently fucking her anus with my fingers. She moaned softly.
"Does it feel good?" I asked her as I continued gently finger-fucking her bottom.
"A little," she answered.
I let go of her cheek with my other hand and slipped it down, delicately petting her soft, smooth pussy lips. She let out the most adorable sound, louder now, a sweet, high-pitched moan.
"Heidi," I whispered to her, "I'd like to put something even bigger in your bottom now."
She lifted her face, her chin on my sternum again. "OK," she said. "What?"
"I want to put my penis in your bottom now."
She looked at me with her mouth open, a look of surprise, but with a little hint of a smile as well. "You want to put your penis in my bottom?"
"Yeah, would that be OK?"
"OK," she said, very quietly, but with that beautiful little smile on her beautiful little face.
I lifted my head and gave her a little peck on the lips, then climbed out from underneath her. She seemed to know that she should just stay on her hands and knees, right in the pile of leaves, and I took my position behind her. I lifted the little pink miniskirt over her ass and pulled her white cotton panties down. I could see her chubby little pussy lips, the cleft between them leading upward toward her little pink anus.
I lifted my fingers to my mouth and spit on them, then rubbed them over my cockhead, lifted them and spit on them again and rubbed them on her little hole. And then, using one hand to hold her cheeks open, I directed my cock down with the other. I rubbed it over her anus a couple of times, then gripped it tight and pushed it in.
She made a painful grunt and buried her face in the leaves, and I pushed in even further. I could tell that the little trooper was trying to keep her asshole as loose as she could and I was able to push my entire head into her.
It was wonderfully warm inside her, and l could feel her tighten her sphincter, clamping down hard on my solid erection. I pulled back, easing my head out of her anus, then pushed in again. She grunted as I pushed in, but I could feel her trying to loosen as the crown of my head stretched her little anus open.
I grabbed the little girl's beautiful ass, one cheek in each hand, and then just let her tight, wonderful anus give me head, slowly at first, just pulling and pushing my head in and out of her. The first few times, she continued grunting painfully when I pushed in, but after a while she loosened somewhat and her grunts turned into adorable little moans and I could tell, for the first time, that the little girl was beginning to enjoy having a cock in her ass.
As I fucked her anus, I reached a hand down between her legs and found her little clitoris and started flicking it between my fingers. Her little moans grew breathy, and I started fucking her harder, my cockhead now burrowing deeper into her hot rectum, her asshole clamping half-way down my shaft.
I lifted my other hand above her cheek. "You're such a naughty girl, Heidi," I said, and I slapped her bottom. "You're such a naughty little girl!" And I slapped her bottom again, nice and hard. "Tell me, Heidi, tell me what you are!"
"I'm a naughty little girl!" she shouted in her sweet little high-pitched voice.
And I slapped her bottom again, driving my cock hard into her, even deeper, my head forcing his way inside her, her tight hole three-quarters of the way down my cock.
"Oh, fuck, Heidi, I'm gonna come!" I shouted, and then I pulled out of her entirely and, as I felt my orgasm boiling inside me, I pressed my cock against the little slit between her beautiful pale pussy lips and my come fired out of me, defiling the little girl's virgin cunt with my sperm.
The next afternoon I heard my doorbell ring. I opened the door and saw beautiful little Heidi.
"Wanna play in the leaves again?" she asked.
For more about Heidi, see the poem Pink Skirt Up, White Panties Down and the story Heidi Gets a Spanking.
| Nickname | Date | Feedback |
|---|---|---|
| Bob | Do you have someone proof your stuff. You first paragraph repeated some lines three times.. | |
| Anonymous | That was a fun little story, slightly marred by pasting errors in the 1st, 2nd, and last paragraphs. | |
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Sorry, Bob and Anon (and other readers when I first posted it); I was posting it late at night from my iPhone, and iPhones have the most annoying habit of accidentally copy and pasting without the user even realizing it. And, once I posted, I fell immediately asleep so didn't have a chance to look it over until morning. Anyway, all is fixed now. --Chris |
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| Roleplayer | Would luv to read about Heidi learning to achieve intense multiple orgasms while being double penetrated by 2 fat cocks | |
| KLT | Great story, but much too short. At 9 years old there's plenty of time to teach her how her anal pleasure can be enhanced through use of her other holes, and to tell us about the journey. | |
| Lunalupo | am not a pedo but I like to read sexcapades with little ones where they are not hurt. I especially like little boys getting sucked off by women and girls. Thanks for sharing Heidi with us. | |
| john | very enjoyable story , I will have something to think about when I rake my leaves. | |
| mikeydee | great story. What a dirty little girl. I think I would have cum as soon as my head slipped into her little tight bottom. that's what happens any time my wife lets me do that. | |
| writerz01 | Lovely tale. Learning to love anal so young. Thanks for sharing. | |
| Edd | Not only did she like anal she liked being spanked. You should do a part two. do her in the bed at home but before she gets it anal she should be paddled first to get her horny. put a pillow under her belly on the bed and paddle that bottom pink. She may cry a little but it will get her going. | |
| Rik | I really like your stories. The Heidi anal story was great. The only bad thing I can say about your stories is to make them longer and lead up to the actual sex act with sexy playing and flirting beforehand. | |
| cellia | Enjoyable, erotic, and just enough to make me cum | |
| funforhere | Another well written, well structured and imaginative story. Playing in leaves - how many would have thought of something like that as seduction technique? Personally, if it had been me, I would have written that John discharged his seed into Heidi's bowels, but whatever floats your boat... | |
| Anonymous | loved it | |
| Uncaba | Well...geee... it's a great setup. I think I would have enjoyed a little more detail especially toward the ending climax. A good stroke story. | |
| Andy | Nice. Works for me!! Para 4. Maybe you mean "averse"? - "not entirely averse" |
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Thanks for the edit, Andy, I've fixed it.
--Chris |
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| quasimodo | love this story but can not for the life of me understand folks preoccupation with anal sex.....why use the tradesmen s entrance when you have a beautiful front door......look forward to a sequel !! | |
| mikeydee | I would love to give you some story ideas... | |
| Definitely interested mikey. Can't promise anything, but interested. I will send you an email, but just in case it winds up in your junk mail I figured I'd mention it here, too. Feel free to just use the comments form below to follow up if you'd like. --Chris |
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| Ladybug | And I just finished raking my leaves, and my grand daughter was so
willing to help. She's just at that inquisitive age, and would have been
a great ASS-ett. Ladybug |
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| Nina | Mine was with a 14 year old girl. I was 11 years old. She was cubby like I was. She took me places I never knew existed. The first time she put her fingers inside my panties was like nothing I had ever felt before. I miss those days with her. | |
| Thanks for the extremely erotic memory, Nina! --Chris |
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| dave | great story.... luvved every minute of it,,,,, | |
| Joe | Excellent story, loved every line of it. Would love to see more anal stories, perhaps teen lovers experimenting to avoid pregnancy or to gain access to a "club" or group. another favorite fantasy is an innocent young lady going for her first gynecological exam. Stern doctor (had a tough previous patient), a little humiliating for the girl. Keep it up Chris so I can keep it up! | |
| Little Jimmy | When I was around four or five there was a little gal around eight that had me hanging from a closet rod in her parents garage she use to play in and that was my introduction to oral sex. I think it was never used other than her playhouse. She didn't let down until my little body was shaking from what I learned later must have been an orgasm. Man did that little gal know her business. | |
| There's a story that needs to be written, Little Jimmy! Maybe I'll take a stab at it but let us know if you write it down first. And Happy Thanksgiving to everyone in the States! --Chris |
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| Heisenberg | I personally loved the story and wished it was longer :) idc about
typos. I am just here for the stories ^^ So tyvm for great stories and please write more :) |
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| Cats | She's a good girl giving up her bottom for her grown up man. There is nothing hotter than micro girl nipples on a perfectly flat chest. I wish you would have paid more attention to them as well. We all know girls lose all sex appeal once they grow ugly tits and hips. | |
| Thanks for the comment, Cats! And to each their own, I always say, but I must confess that while I find little undeveloped nipples quite enjoyable, I personally believe there is nothing so fine as a nice set of warm chubby boobies in your face. --Chris |
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| Anonymous | Very sexy story can't wait to read more about her | |
| iluvgirlsfeet | Loved it! Was rock hard the entire time. My favorite part is when she is laying on your chest, rubbing against your cock while you held her Small buttocks. Loved the thought of that, truly made my penis throb. I imagined her face rosy red, her child bottom in your hands. Your cock throbbing, dripping even, while her cute little legs and feet to your side straddling you. I could spend hours like that. Thanks!! | |
| ozdogfox | lovely anal tale, there are so many little girls I would love to seduce in this fashion. | |
| Anonymous | Just found your page and I really enjoyed Heidi Loves to Play in Leaves. I'll be reading more of your work for sure, starting with the next Heidi story right now! | |
| kevin | 12/28/2015 | Beautifully described. I could feel Heidi's tightness wrapped around your hardness. thank you |
| Anonymous | 1/4/2015 | Holy moley that was fantastic i came so hard to those beautiful images like man what a beautiful short story so loving and free |
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