Heather… Anal training the ex. [MF]

She’d broken up with me about a year ago. It fucking killed me, but we’d stayed friends, which was difficult because seeing her with other guys make me fucking nauseous. And she was always with another guy.

It was late afternoon when my doorbell rang. I was confused, to say the least. I asked if everything was okay and she nodded. I invited her in, offered her a cup of tea and she asked for a gin and tonic. She rarely drank in the afternoon, so something was up.

I sat down with a gin and tonic of my very own and proceeded to roll a joint as I looked her over and tried not to think about the fact that she was no longer mine. I’m pretty sure I was in love with her.

“To what do I owe this pleasure?” I asked

“It’s a bit awkward…” she replied.

A long pause. I waited and wondered and truly believed she was about to tell me I needed to get myself tested, the curse of a desperately curious mind. Fuck.

“You know I’m with Derek, right?”
I nodded. Fuck Derek. We were never friends, but I knew him. Fuck Derek. Where the fuck was this going?

“Its his birthday next week”

I shrugged. Who cares? Fuck Derek. Where the fuck was this going? I lit up the joint and took a deep drag and resisted the urge to yell “WHERE THE FUCK IS THIS GOING?”

“Okay… I can’t believe I’m telling you this… fuck it… he wants… I think he’s obsessed…”

She trailed off. The most pregnant of pauses. I handed her the joint and tried to act like I wasn’t getting impatient.

“Why are guys obsessed with anal sex?”

What. The. Fuck. How was I supposed to respond? I just did a half shrug and downed the rest of my drink. She droned on, stuff about me and those wayward prods back when we were together, about the finger I sometimes was allowed to wriggle about, about the porn she’d found me watching. I felt like I was being blamed for all men.

“Where the fuck is this going?” I finally asked.

Enough. If she came over to tell me off for being human then fuck her and fuck Derek.
“Derek wants to do it. “

“No shit. So you’re here for advice?”

“No. Dana gave me all the advice I need. How do I say this.. Derek is… endowed.”

“So you’re here to brag? I’m so happy for you and your boyfriend and his big cock. Congratulations.”

“No. No. I’m not here to brag.”

“Then please, for my sanity’s sake, tell me why you’re here.”

Another pause. I was pissed, thinking about her getting sodomised by Derek’s huge cock, half hard and thoroughly depressed at the prospect of jerking off to the image as soon as she left. I poured myself another drink and took a big drag.

“I’m here because I need practice with something… smaller…”

I almost fucking choked. I literally coughed. I tried not to grin the sleaziest grin and clearly failed, because she laughed. Hooray for me and my average cock.

“I figured you’d be up for it” She said, a reference to my obvious bulge.

She swore me to secrecy. Then she relayed Dana’s advice- booze, weed, lube and a fast. She said it was okay for us to have fun, but that it was “educational”. I just nodded and smiled.

“Let’s get this over with… take your clothes off… I’m fucking starving…” Sexy.

She rummaged around her bag and retrieved a bottle of lube and a box of condoms. And then she stood up and disappeared into the bathroom. I was excited and confused and angry, staring at the bottle of lube as I stripped down to my boxers, my last remaining scrap of dignity.

When she emerged she was naked. Completely naked. I stared at that body that I’d seen naked countless times and realised how much I missed it, her little perky boobs and her perfect nipples, that little birthmark on her hip, her milky thighs. Her Bush was different, a strip instead of a patch. Between her legs her lips seemed to dangle a bit more than they did in my memory.

I was agonizingly, longingly hard, a patch of precum spreading across my tented boxers. I looked at her, then the lube, then my tent. I had to idea where or how to begin. I walked towards her and she nervously backed away, until she was against the wall.

I tried to kiss her and she turned her head so I sucked her ear and resisted the urge to tell her I missed her. I nibbled on her neck and moved down to her chest, sucking on her nipples, one at a time, greeting them like long lost friends, listening to her whimper. I fell to my knees and before she knew what was what I had my mouth on her clit, tasting that familiar taste, studying the smell of her new, musky body wash.

“No…”

I ignored her because it wasn’t a real no, it was a guilty no. Her body betrayed her objection. Her leg hooked over my shoulder and she groaned as I lapped away and invited my fingers to explore her. Two, then three, and then four. Four. She’d never taken four so easily. I tried not to think about why. Fucking Derek and his big cock, stretching her, changing her.

“Oh fuck… baby…. “

She’d never said ‘baby’ before. She was louder now, different. Grinding against my knuckles as I diligently licked her clit, tugging at my hair as she got closer, dripping down my wrist. Getting creamy, which I knew from experience meant she was on the brink. Her foot was on my shoulder, trying to push me away. Typical Heather, terrified of gushing, or as she called it, peeing on me. I held firm, fingers twisting, tongue flicking, lips sucking.

“I’m coming…. Baby, I’m coming…”

The words were all new. Normally she’d whimper my name, at best. She’d changed. Even her orgasm was different. Louder, more dramatic, a bit theatrical. But I felt it. It was real. My hand was drenched. She was trembling. I pulled my creamy, soaking fingers out and grinned a wet, proud grin as I watched her stumble to the kitchen to pour herself a drink. Just gin, no tonic. She downed it in one.

“Stop distracting me… “

I moved to the couch and she walked over to the table, tossed me the condoms, picked up the lube and carefully read the label, like it was a prescription painkiller. I watched her unwrap the plastic and open the bottle, carefully squeezing a bit out into her finger, testing it, smelling it, braving a lick. I laughed as she cringed and wrapped up before she changed her mind.

Attempt 1

She sat next to me, squeezed some lube on my sheathed erection and straddled me. I sucked her tits and looked up at her face, holding her cheeks apart as she slid my tip up and down her crack.

“Don’t move… let me do it..”

I sat there as she attempted to coax it in, squeezing me with her fingers, prodding, testing, stopping as soon as there was any give. It was half-hearted at best, hopeful but futile.

Attempt 2

She was on her knees, on the couch, still clinging to my cock, still in charge. More lube. I held her cheeks apart and watched as she pressed back, testing, the tip of my tip stretching her a little, teasing me.

“Almost” I lied, trying to encourage her, to make her believe, to make her keep trying. The view was mesmerizing. The urge to thrust was overwhelming. After a few more false starts and a somewhat promising poke she gave up.

“It’s not working…” she said, letting go.

I didn’t think. I just shoved it into her vagina. A place I was once familiar with. I thought I knew my way around but I felt like a stranger wandering about in a strange land. Vagina: New Vegas. The same gameplay, but unfamiliar terrain. A bigger map.

“No.. we shouldn’t…”

I wanted to explore, to travel about the strange, cavernous world. It was so different it felt like an entirely new franchise. Her lips used to cling. I remembered layers, folds, a grip. No more
.
“Stop distracting me” she said, pulling away, evicting me.

Attempt 3

She was lying flat on the couch, on her stomach, prone. I sat on her thighs and played with her cheeks, spreading them, massaging them. More lube. I rubbed her ring and felt it pucker up and grunted something helpful like “relax” before unceremoniously poking my thumb in. She squealed and her sphincter tightened but I held firm. “Breathe” I muttered, like I knew what I was doing.

It fucking worked. Her hole stopped fighting me. I wriggled it about a bit, venturing a bit deeper. She pushed back and my thumb disappeared and I swear I almost came out of sheer excitement. It was at that precise moment I realised it might actually happen.

God was it fun. I took my time because I could, diligently studying her asshole, fucking it with my thumb as she fucked it back. Slipping it out and then back in again. Going through a ridiculous amount of slimy lube. My other hand was between her thighs, rubbing, fingers slipping in and out of her cavernous, creamy vagina. She started whimpering. She started writhing. I felt her fingertips, strumming her clit as I fingerfucked both her holes.

“Do it”

“You’ll have to be more specific Heather…”

“Put it in my ass…”

“Put what in your ass Heather”

“Your fucking cock…. Just do it…”

Just do it. My fingers retreated. I squeezed out a river of lube along her crack and a bucketload more on my obscenely hard erection, carefully coating every bit of the sheath without accidentally finishing myself off.

I was so excited it was frightening. She was still strumming, gently writhing, moaning a soft moan. I slid my tip along her crack, and she didn’t grab it. I was in control. I rested it on her puckered ring and gently pushed the tip down with my fingers.

“Breathe” this time I was talking to myself.

“Oh fuck oh fuck oh fuck”

I watched my cock pry her open, slowly creeping in. I burned the sight into my memory, her ring squeezing my tip, deforming it, reluctantly stretching. She pressed back. Teamwork.

“Owwwww fuck don’t stop just fucking do it….”

With a bit of a thrust my tip plunged in.

“It’s in!”

“OWW FUCK NO SHIT DON’T MOVE”

“tighhhhtt”

“OHHWWW FUCK I’M COMING”

I didn’t expect it, a self induced orgasm, her sphincter crushing me, making me whimper, pulling me in, making her yowl like a wounded animal, making me cum. Years of anticipation. Ten seconds of painful pleasure.

I watched my shaft pulse as she shuddered and trembled, whimpering as I deflated, defeated, undone. My limp cock slipped out of the sheath which stayed inside her.

“Owww” she whined, crawling off the couch, stumbling to the kitchen, opening the fridge.

“I’m so fucking hungry”

I watched her rummage around the fridge, bent over, a used condom dangling out of her ass, cum oozing down her inner thigh. I watched her eat pickles, naked, unashamedly stroking my limp cock as I did so.

“Stop that. It’s not happening. There’s no fucking way. He’s too big…”

“We can try again”

“Nope. He can have a threesome instead. I’m sure Dana would be up for it…”

Motherfucker.

I got a consolation handjob in the shower and a sloppy kiss goodbye.

Source: reddit.com/r/gonewildstories/comments/bx8vuv/heather_anal_training_the_ex_mf