The re-return first anal with [m]y ex g[f]

As a background to this, my GF and I had split up, it wasn’t pretty, we’d been living together for a year & change and issues had built and built and boiled over big time.

We’d had a pretty ntense relationship, she’d struggled with some mental health issues and I had not necessarily been the most understanding, and while the fights were heated and firery, the sex was great. Learned early on that she was happiest in her mind when she was being regularly railed. And fortunately, whilst our social coexistence wasn’t the best, our sex life was def on point.
I’ve always been pretty dominant in bed, taking charge and largely (I hope) knowing what I’m doing, I’m good with my hands and while my cock isn’t massive (a healthy 6+”) it’s very, very thick, and I guess this has always given me quite a lot of confidence in bed.
Anyways, I digress
Sex between us had always been good, she loved being taken, and hard, I’m 6’4 and her little Asian body was fun to grab, pin down, toss around as my whim took me.
So whilst we had parted not on good terms (read, almost downright loathing), it actually wasn’t the biggest surprise getting a msg from her one night a few months or so after splitting saying she wanted to be fucked.
She’d moved back in with her parents and I’d stayed on in the condo we’d previously shared.
I’d thought it a bad idea given how things had finished and largely ignored it.
Her msgs moved to a more pleading and intriguing tone, asking ‘sir’ to please use her pussy and mouth.
Yeah I cracked..sue me
Coming home one night after a few drinks I admit I was thinking with my dick. Sure enough as timing would have it, she msg’d, saying she was drunk, had just fucked a guy and was disappointed. He’d lasted 5 pumps of small-dicked overeagerness and she missed being properly ploughed.

Now is also probabaly a good time to mention that for all the free license I had in taking her, anal was never on the cards, she’d had a bad experience before of a guy just jamming it in and hurt like hell, so she’d sworn off it for life, she liked her hole licked or rubbed around the outside, but nothing was ever to go in haha.
My tipsy dirty mind in play I told her outright, I loved using her willing pussy but the price of her getting the fucking she wants, is her ass.
The texts continued on that night, very sexual and now anal in nature, she’s, to my mind, just playing along for the sexting vibe while we both remotely take care of ourselves.
We complete our mutual sexting business of the night and fall asleep.
Next morning, I kinda think it was a bad idea to have engaged again, but don’t overly dwell on it.
Late that morning I’m at work amd receive a msg, it’s a pic of her, legs spread, two fingers in her pussy and a small plug in her ass
Caption just reads ‘practicing’…

Fuck that’s hot..damn you lack of will power..
I’m still a little hesitant about the whole thing, I don’t want to get back together, that is very clear, so I don’t want this to fall into some regular reconciliation.
I back off for a while, but you guessed it, drunk horn dog that I am, those msgs would get revisited.
She, explicitly stated this is only about sex, this isn’t a date, just a dirty mutual transaction.

Dammit dick, you win, we’re doing this.

It’s prob about 4-5 months or so after we finished now, and I’d gone back into being a full dom, bag of toys, tools and all.
It was easier for me to deal with her with my dom hat on rather than as the partner i’d been for a few years, and whilst I’d taken charge whilst in bed with her, we’d never had a full dom/sub existence.
So I set out some new rules;
– I was always to be ‘sir’
– she’d always spat my cum in the sink previously, now if I treated her to me cumming in her mouth she was to let it run out down her chin and over her body, so she was suitably decorated as my cum toy
– she was to travel to mine on public transport (worth noting, we live in a very safe place), she was to wear a thin summer dress and nothing underneath. While her tits weren’t huge, they were an OK size and decent shape and she had quite big puffy nipples that are very visible when bra-less. I wanted her to be in the mindset of a slut when she arrived, everyone can see her there and know she’s just travelling to get fucked.
– every night for the week before we were to meet she was to send me a quick video of her masturbating, but fingering her ass as she did so, with the instruction to get into the mindset of craving a cock in her ass.
– when she arrived she wasn’t to greet me or say anything, she was to walk straight into the living room, get down on her knees, open her mouth and wait for my cock.

Sure enough, the time came around, she followed the video instructions, I received increasingly pleading requests to have her ass used and pounded.

She msg’d to say she was on her way, that the people on the train were looking at her, could see the clear outline of her tits, she felt slutty and wet, felt they could almost smell the sex on her given she said, she was practically dripping down her thigh.

She arrived and good girl that she is, waltzed straight past me, head bowed, and took up her place kneeling on the rug in the middle of the living room floor.
Enjoying the scene I poured myself a glass of wine a sat back on the sofa, she moved to come over and kneel in front of me but I sent her back.
I unbuttoned and started stroking myself while keeping eye contact, I could see she was struggling keeping her mouth open the whole time, little gasps as she swallowed the saliva build up, but she never broke eye contact and never closed her mouth, I could see her hand keep drifting to go between her legs, desperate to rub her clit and get off after this denial build up, but unsure if I’d allow it.
I told her she could touch herself when I put my cock in her mouth. She sighed somewhat frustrated, but kept her hand still.

Putting down my wine I stood up and went to stand in front of her, still stroking my cock over her face, laying my shaft on her cheek as she looked up at me. I reached down into her dress, cupping, teasing then pinching her nipple hard, pulling slightly as i withdrew my hand, her moan was more gabbled and gasp as she maintained keeping her mouth open.
Seeing how well behaved she was being, it was only fair to reward her. Sliding the head of my cock into her mouth she instantly wrapped her lips around it, her eyes closed, she moans deeply as I see her hand shoot under the skirt of her dress to immediately begin playing with her pussy, rubbing her clit in time with her head sliding back and forth along my cock.
I wrapped my hand into her hair, taking a firm grip so I had control of her, I withdrew my cock from her mouth and redirected her to lick and suck on my balls, her eyes closed as she excitedly tongued and sucked on first one then the other, her moans getting more frequent and shallower as I could tell she was building up, her hand furiously rubbing her clit below.
“Can I cum?”
She’d withdrawn and was looking up at me, some desperation in her tone
“No”
I said and slid my cock back deep into her mouth, my hand firmly in her hair held her in place as my cock pushed through to the back of her mouth.
Her eyes clenched tightly shut, concentration I could tell, from holding off from cumming, her hand while still rubbing her clit, was starting to take intermittent pauses I could see as she was clearly fighting off crossing the line.
I pushed deep into her throat, held her in place and told her to look at me.
Her eyes watering and kinda panda-ish from smudged mascara, she met my eyes.
I asked if she wanted to cum, she tried to nod as best she could, my cock still rooted firmly deep in her mouth.
I said she now could.
I eased back out to let her catch her breath, before starting to trust into her, fucking her willing mouth, her eyes clenched shut again and it was only a minute or so before she began to let out her tell tale whimpers, body almost seizing with slight trembles as she began to cum.
I eased my grip and let her enjoy her well earned moment, she pretty much collapsed against my leg, her arm gripped around my thigh, her face buried in the v where my hip meets my stomach, a large gasp leaves her as her orgasm rolls through her and she pants against me.
I leave her kneeling there as she catches her breathe, I bring her over a glass of wine, which she proceeds to finish quickly in a few gulps.
I stand her up and bend her over the arm rest of the sofa.
Her high heels barely keeping her feet on the ground as I push her shoulders and face down flat into the cushion.
I pull up her dress, and with my foot nudge her feet further apart so she is more fully spread and exposed
I couldn’t resist that willing sight and drove my cock fully inside her, her moans muffled by a mouth full of cushion as I slam into her.
I reach forward and grab each of her arms just above the elbow and lift her, her body suspended helpless in my firm grip as I drive hard inside her from behind.
After a fast, rough pounding I lower her back down, she slumps fully face first into the cushion, tired and used.
I tell her to stay there as I walk into my room.
Coming back, she’s still bent over the sofa, I move to stand back beside her, my hands briefly enjoying her body, I drip some lube onto her asshole and feel her gasp and tense a little.
With one hand play with her clit, my other hand teasing and rubbing circles around her tight hole with the lube.

My playing with her clit has its effect and soon her hips are rocking back into my hand, her rhythm pushing back against me as I rub, at the same time the tip of my other thumb starts to tease open her ass, I feel her muscle relaxing and almost welcoming in my thumb as I play with her.
I reach beside me and grab the lube and beads I’d brought out, I apply a healthy amount back over her asshole and pussy (not that her pussy needed it, she was soaked haha), then gave a generous coating to the beads.
The beads ranged in size, smallest to largest, I pressed the first one against her hole as I resumed teasing her clit, with no effort it slipped straight in, same for the next two, both welcomed straight in to her willing ass. The fourth one was a little wider and needed teasing and twisting a little as I coaxed it in, but happily in it went with a satisfied moan from her.
The last one I could see was going to stretch her a bit more, again I teased and twisted, to my very pleasant surprised she pressed her ass back firmly against my hand, and i have to tell you it is a really fucking hot sight to watch a tight, barely used hole stretch out and around the toy, gripping it, almost willing it inside.

A much louder groan this time that I could tell was firmly on the confusing border of pleasure and pain as she was stretched out.
She was taking quick sharp breathes, clearly steeling herself against what she’d just done, but in no time at all and with strongly renewed fervor she was grinding back against my hand playing with her pussy.
You’ll forgive me, as much as I’d like to describe how i spent some time playing with her there and savouring that moment where she just switched in her mind to realising she’s getting off on her ass being penetrated, I didn’t, I came straight behind her and started fucking her again.
Enjoying the feeling of the ridges of the beads in her ass against my cock as I pushed inside her pussy.
I didn’t hold back, my hips were driving hard against her as I slammed my cock repeatedly deep inside her.
Both her hands clenched tight on the sides of the cushion, her face buried into it muffling her moans and unintelligible enthusiasm, loving the feeling of being double penetrated for the first time.

One hand gripping her waist for leverage. I continued fucking her hard, my other hand I hooked a finger into the ring hanging from the beads and began to gently pull, the girth of the large bead teasing open her hole again, her moans became groans and it wasn’t long before she was lost again into a quivering, orgasm space out, as I continued to fuck her.
I withdrew after a few final hard slams and stood back, enjoy the sight of her bent over, still shaking and making little squeeks of happiness into the cushion, the end string of the beads hanging out of her ass and her pussy, soaking wet and freshly used.
I took her hand and lead her back to kneel on the rug in the living room, pushed her down to all fours and knelt behind her.
I told her to rub her pussy and she obediently began, her fingers furiously rubbing her clit as I began teasing the beads back out of her ass, the first couple with a little resistance, I kept each one, held briefly in place half way out, stretching her, each was met with an involuntary squirm as her ass stretched, but her continued moans and rhythmic rocking as she played with her clit painted a clear picture of how much she was enjoying this.
The last few smaller beads slipped out easily and I took the opportunity of her hole still bring slightly spread to drip some more lube in, I coated my shaft and tip also as I stroked myself
I knelt up behind her and pressed the tip of my cock against her hole, it parted easily and I happily watched the tip of my cock slide gently inside her.
My shaft gets thick quickly after the head and as such only moved slowly. Pausing as I felt her body tense. She wasn’t making any noise and could tell she was holding her breathe. I stayed there with just the tip inside, her tight hole just spread around start of my shaft.
Then she started pressing back against me, I remained stationary, letting her control the entry, I dripped some extra lube on as she took hesitant little jerks back into me.
Then with a very load groan, she pressed entirely back against me, my cock fully buried inside her ass.
She reached back desperately, grabbing my leg to pin me in there and stopping me withdrawing, her gasps and little squeeks were almost panicked and frantic as she both fought to catch her breath and moan as she furiously rubbed her clit.
A curious smirk on my face I enjoyed watching her have the most confused orgasm of her life to date I’m sure, cumming in less than a minute of having a cock in her ass
Once the shudders of her unexpected orgasm passed she let go of my leg and slumped forward, shoulders and face buried in the rug.
I began to slowly move my hips, slow deliberate thrusts back and forth, her vice like grip on my cock feeling amazing, her body soon began responding, coming out of its post-cum stupor, giving again those same, almost paniced gasps as I begin to properly fuck her ass.
It wasn’t long before she was taking me easily, my full length burying balls deep into her.
I withdrew and flipped her over, kneeling I brought her head up and she eagerly sucked on me, cleaning and devouring the cock that was only seconds ago buried fully in her ass.
I pushed her back to lay flat, had her grab each of her legs behind the knee and spread for me.
She was always enjoyably flexible, and I’m not going to lie, I do still have happy thoughts today of that image of her, pulling her legs back to spread wide for me, complete control given over to me to fuck her in whichever hole or however I wanted.. and I did..indeed I did… I pounded her hard..
Eventually even the strongest will breaks and I could feel myself building up.
Wild horses couldn’t have dragged my hips backwards as I drove that final thrust deep into her ass, spurt after spurt unloading inside her.
Pulling out, her hole stretched and used, I see my cum beginning to leak out of her, she remains in position, legs spread for me to view her there thoroughly used and exhausted. Her dress a good bit more dishevelled than when she’d arrived, and maybe with a few extra stains..
I came up to kneel by her head and she eagerly cleaned off my cock in her mouth.

Finished, I poured myself another wine and went back to sit on the sofa.
She lay there spread for another 5mins or so on the ground, in a happy used stupor, before rolling gingerly over, standing up very shakily, her legs clearly wobbly.
She pulled down her dress to cover her soaked hips and thighs, gave me a very overwhelmed but joyous smile and without another word walked out.
Many msgs went back and forth over the next couple of months, her asking for a rematch or me enjoying a drunk horny relapse, but it was prob about a year or so later before we next actually saw each other.
It was late in a bar, we were both out withour different friends, saw each other and exchanged pleasantries and went about our eve, didn’t think anything else of it until in the early hours when rolling out to get a taxi back, sure enough it was the two of us at the taxi stand.
She asked if she could come back, I said last time was great but should just be a one off, yadda yadda… anyway long story short, my horny ass gave in.
And while we didn’t have a similar eve of anal adventures, was very delighted that as she knelt in front of me later that night, draining the last drop of cum from my balls into her mouth, she looked up at me and with a most innocent look, she let all the cum run out of her mouth to drip down her body.. Good girl had still remembered the rules…

Source: reddit.com/r/gonewildstories/comments/vstabp/the_rereturn_first_anal_with_my_ex_gf