# # #

Oral Olivia and Anal Amanda

3060 words | 2 |4.00
By

A story from a decade ago about two young girls I was simultaneously grooming and got different gifts from

Those familiar with my previous stories know that I’m an old pervert with a taste for younger girls. I’ve successfully manipulated and taken advantage of countless teens, sweet talking them into letting me inside their tight little untouched holes with promises of marriage, true love, whatever bullshit they want to hear to think you want something more out of them than their sweet tight hole to fill up with perverted old nectar.

But sometimes it doesn’t always work, a few of these little bitches have been stubborn as hell and were stern on no “real” sex. In retrospect, they were the smart ones. They got to grow up and live life knowing they hadn’t given their precious virginity to a liar and pedophile who just used them for all they were worth. I’ve had plenty of trophies, might even have some bastard offspring running around out there from a few girls I made into teen moms. This story is about two girls that had been smart enough to say no, but still gave me something, and let me give them something sweet to remember this sneaky stranger by, hopefully forever.

Olivia was a 17 year old who looked average, not ugly by any means, but I definitely had no intention of ever talking to her again once she gave me her pussy. The problem was, she hadn’t done that yet. Usually they’re easy enough to talk into making some bad, life altering choices, but the younger they are the stupider they tend to be, and the quicker they’re wanting to grow up and do adult things. By 17, they’re wiser… Just not wise enough.

I know my details annoy some readers who just want me to get.to the point, so Olivia was a girl I’d been blowjobs from, mostly road head for about three months. I drive a big enough truck that I won’t get any lookyloos to nosy on over and see my old man ass being gone to town on by a girl that could pass as a teenage daughter, and after chatting online for awhile after meeting and agreeing to be picked up before school, it was always nice to start the day off with the tender suckling of a yet legal adult. This girl loved it. She would meet me a block away from her house and get into my truck with giddy anticipation, hungrily to lunging at my dick like it was breakfast. No complaints on that front. Sometimes I hadn’t quite cum before we got close to her school so we would park at the far end of a store and let her finish up her job and get her meal. She loved the taste of my cum and it drove me wild sending this little minor to class with a belly full of me.

But, she didn’t want to have sex yet. Especially since I refuse to wear condoms. I told her time and time again I’m as sterile as can be (I’m a great liar) but this little bitch just said she wasn’t ready yet, gave me every excuse in the book, and would say she enjoyed giving oral to me more than she even liked masturbating. I may technically be a statuary rapist, but I wasn’t going to force the girl and risk her ratting me out to the cops over some pussy when she was my own personal human vacuum. I pressed the topic a few times but then she suddenly stopped needing rides to school every morning, so I backed off. There was another girl I was busting my nut to at the same time anyway.

Going multiple times a day was definitely easier in my you get days. As I got older, just cumming a single load a day was taking a toll on my mechanics and felt as tiring and left me just as sore as if I’d been cumming five times daily. So when Olivia started acting like a little bitch to me, I didn’t mind so much taking a few days off to let my baby maker rest. But then I found myself getting horny and needing that release from naive young teenage girls.

That’s when I met Amanda. Definitely prettier than Olivia, no contest. Younger too, having just turned 16 when we crossed paths. I ran into while she was actually out birthday shopping with her mom and although it was risky to make contact with a parent around, I knew how to be inconspicuous enough while giving this young sandy haired girl just enough attention to make her blush. We ended up getting a chance to meet when her mom went to try some clothes on and I approached her from behind – which still amuses me considering what I ended up getting from her.

She was definitely a little troublemaker, this one. And she was extremely flattered to have an old creep smirking at her. She outright asked me if I was some kind of pedophile who likes little girls or something, and I said I could keep a secret if she could. She instantly smiled and said she was very good at keeping secrets. I didn’t want to take up too much time with that first encounter, so we sneakily exchanged some contact info and I told her to get in touch when she wanted a late birthday gift from an older man. Amanda eagerly nodded and I got a text from her that same night.

I didn’t even waste time with the usual bullshit of trying to lure this one in, she was rather blunt and we both knew what we wanted. She was a spitfire little girl, and definitely got off on a little bit of trouble. We were exchanging nude photos and I was telling her what I wanted to do to her within hours. I thought it was odd how all her pictures were of her bent over, spread and showing both holes instead of just a typical close-up of her pussy though. I pressed that, and she said she would explain when we met up, but definitely assured that there was fun to be had.

It was a stormy Saturday morning when Amanda and I planned to get together, I’d told her I was just visiting town and staying at a local motel 6 which I’d rented so this way we would have a place to go and she wouldn’t assume I was local. She already had been meeting up with guys and having friends cover for her so sneaking away was easy for her, this girl was such trouble. She told me she was a virgin still, and when I picked the little girl up and took her back to the motel room she explained why.

It turned out Amanda was actually quite the little highschool slut, she’d been messing around with guys for two years but hadn’t actually had sex yet, though not from lack of trying. Apparently she has something called vaginismus, which just like everyone else who had never heard that term I was like what the hell is that? It was some kind of fucked up medical condition that made her muscles in the vagina really fucking tight, and she said she couldn’t have sex, even had trouble working on tiny tampons. Of course I was like, oh great… There went my chance of deflowering another victim.

I figured it would just be more oral fun, which since it’d been a week since I got a lick from what’s-her-face, I could deal with some suckage. But that’s when she dropped the bombshell on me and I put two and two together about why she’d been sending me her asshole with her pussy pics. This girl was into anal. Paint me intrigued.

I’ve fucked quite a few girls up the ass, but to be honest it’s not my preference. It’s nice but feels so tight and slick compared to the ridges of a pussy or even the flicking and sucking of a tongue and mouth. Doesn’t mean I’m against it though, and especially not when a fine little girl is telling me how she’s learned to love it and how she always had the fantasy of a hot older man fucking her better than the boys at school. I was happy to oblige.

We got back to the motel room and I instantly had her against the wall shoving my tongue into her mouth and feeling up her small but nice titties. She looked a little shocked but I told her I’m not like those boys at her school, I was going to show her what fucking a real man was like. She nodded quickly and said yes daddy.

I stripped my clothes off and she pet my hairy, muscular if not a little flabby older man body, I could feel her shaking at her finger tips as she looked down at my growing member with bulging eyes. Biggest cock she’d seen in real life, I’m guessing. This girl was going to know she’d had a real man stretch her ass out. She’d be walking funny by time I was done with the little bitch.

I told her, now you, and she nodded and began taking her clothes off as I laid on the bed jerking off and watching her strip. She had a tight little body for sure, she asked me if I liked it and I gave a creepy, perverted “mmmmhmm” before telling her to turn and bend over so I could see those holes up close. She obeyed like a good girl. I couldn’t resist, normally I only eat pussy, but knowing I was gonna be balls deep in this girls asshole soon enough I couldn’t help but to spread her ass apart and lick furiously. She gasped and shook before moaning. I also did this because I realized we didn’t have lube and going in dry would be painful for both of us. She did didn’t mind one bit.

After a few minutes she suddenly began screaming “I want it! Take me! Use me!” And I didn’t need to be asked twice. I arranged some pillows so that she could lay on her back with her ass up and although I’d gotten enough head lately, I still had to remind this bitch who her daddy was and kneeled another, tell other to suck my cock and get it nice and wet. The poor girl acted like it wasn’t even going to fit in her mouth, and she kept rubbing it all over her little cheeks. I told her again she was a good girl. I didn’t want much head though, so after I felt she had drooled enough on the daddy dick she said she loved already, I slipped down and got her legs up on my shoulders.

I teased her little pussy a little and she hissed, but shushed her and said not to worry, as I aimed my rock hard older cock at her ass and had her reach down to spread herself apart even more. I was actually surprised at how easily my cock found itself slipping into her teenage anus. Don’t get me wrong there was still quite a bit of resistance, not even as tight as a virgin pussy, but still enough where I felt like I had to pop the head of my cock in. This girl wasn’t kidding about loving anal though, mine might have been the biggest she had in there but definitely not the first. Her little eyes fluttered shut and she made a sour, scrounged up face somewhere between pleasure and pain. Probably not much different than how she would look taking a huge shit. There was a quick gasp followed by a deep moan, and her pussy started leaking all over me.

“You love this don’t you little girl,” I said as I continued working my cock deeper into her ass.
“Yyyyesssaaa… Fuck! Daddy!”
“That’s right”

She knew her place. She let go of her ass and grapes onto my big arms, and kept telling me how big I was and felt inside her. I’d forgotten how much I enjoyed the feel of a good tight asshole, and I showed that little girl no mercy as my 40 year old cock plunged balls deep into her tight hole, giving her a thorough cavity search. The little bitch really has found a way to get off with anal, I’d never seen a girl cum from me massaging her ass with my cock before. I don’t know if it was just the excitement of being with an older stranger she knew for less than a week, an older guy in general, having risky sex at a cheap motel, being fucked harder and deeper and more fully than boys did at her school, maybe a combination of everything. But goddamn this bitch was screaming when she came. I loved it. It may not have been the virginity I wanted or corrupting another impressionable young teen, but it was better than blowjobs.

I pinched her nipples so tight I was sure I’d bruised them, but she didn’t care. This bitch was my slave now, I had given her the pleasure of a man that no boy had yet to achieve. When I told her I was cumming she didn’t even miss a beat and begged me to fill her little ass up, which I did. And that’s when I remembered why I wasn’t overly fond of anal sex. It was always good right up until my orgasm. The anal cavity was so goddamn right I barely felt myself cum. I knew it had happened, she seemed to feel it more than I did, and in fact I heard women feel a guys cum in them more in their ass than they even do their pussy. I was happy she got enjoyment from it, she purred like a little Kitten.

For me it was just okay. I felt more from knowing my older seed was in a girl young enough to be my daughter and that she’d be feeling this fuck for days more than anything else. Of course I pulled out slowly and cleaned her off with some toilet paper, making sure to piss and make sure I was clean as well.

It was when I was in the bathroom that my phone chimed. Guess fucking who. Olivia. She gave me this long winded text about how stupid she had been being (I agree, fucking irritating bitch) and how she missed me, and might be able to sneak away for a few minutes in the next hour. I wanted to tell her off or even ignore her… But I’m a bastard. I told her I could be on her side of town in 25 minutes. She said that would work perfect.

So I came out of the bathroom and found Amanda still wiping herself off, and kissed her cheek and asked how she was. She was shaking and said her ass definitely felt fucked. I laughed and said good, then made up an excuse about how work was texting me and I had to go. But I wasn’t gonna let this one get away, I assured her I’d be in town for another week and we could meet up again if her ass felt like it could handle more. She enthusiastically chimed in YES! and I said good girl, and to rest her ass up for me. We kissed for awhile before getting dressed and she did in fact tense up when she was bending over to pull her pants back on. I hurt this little girl. I took pride in that.

Once I got my little anal Amanda dropped off and promised I’d meet her again, I flew to Olivia’s usual pick-up point and there she was. She got in my truck and it seemed like all she wanted to do was talk. Trying to be mature and shit, the annoying little cunt. She offered me an apology but I told her there was another way she could show me she was sorry. She smirked, and began petting my lap. We both knew what was going to happen.

Just like she had so many times before, Olivia leaned over and took my cock out of my pants, but this time I was still freshly fucked from Amanda’s asshole. Sbe noted it felt warmer, but I told her I’d just had a busy day, and guided her head into my lap. And there she began licking and sucking my cock that had been quickly wiped, but still was barely cleaned from fucking a other teenagers asshole not even 30 minutes ago.

Am I a bad man? Absolutely. Am I an evil man for having to hold back my chuckles when she moaned about how good my cock tasted this time? You fucking know it. I didn’t give a shit, she’d been a little bitch to me for refusing to put out and neglecting to give me head all week. I don’t even care if she got an infection from it or some kind, she had to be taught a lesson and the best lessons and older man can teach a little girl is with our cocks

Olivia sucked my shit dry, with what little cum I had left to give so soon after unloading in an even younger girls asshole. And she guzzled it all down as if she’s been starved. I pet her hair as she sucked up a mixture my cum and her drool off my cock and she sat up smiling. I was too, but for a whole different reason.

I never saw Olivia again after that night, I missed the head but it wasn’t worth sticking around for anymore. I fucked around with Amanda twice more that month and then kept making plans to “come back into town” but never did. They may have been two virginities I couldn’t claim for once, but I definitely got something out of them that made it worth while.

And if you’re wondering why I ditched Olivia after that, it’s because after seeing her smile at me with a very clear poop nugget lodged between her teeth after sucking my dick that last time, I knew just ever be able to look at her again without laughing.

🔞 Candy.AI 🔥 AI Sex Chat - Roleplay, Erotic Stories, Try for Free 🕹️

Please, Rate This Story:
1 Star2 Stars3 Stars4 Stars5 Stars
(average: 4.00 out of 17 votes)

By # # #

2 Comments

  • Reply Kiddyfucker69 ID:1dw6ykckel4i

    I loved your arse fucking story. Thank you…

    • The Groomer ID:pa1zf7w20d

      Little girls make for the best sets of holes!