Enter by the Exit – Episode 2 [Anal Fingering] [Vaginal Sex] [MILF]

If you read my account of the preceding events in [Episode 1](https://www.reddit.com/r/eroticliterature/comments/ipkfrk/enter_by_the_exit_episode_1_anal_play_anal/), then perhaps some of you are expecting, or even hoping that this will be the story of how a straight-laced older lady had one anal experience and immediately turned into a cross between Phoenix Marie, Belladonna and Abella Danger. That after an impossibly brief refractory period, I was hard again, and I just folded her up like a jackknife, with her knees either side of her head while I did the piledriver on her gaping ass. But this isn’t porn, my brothers and sisters. This is real life, with real people. Real life is messy, real people are messy and complicated. Sometimes the mess is literal, sometimes it’s in our heads, but it’s always there.

So without dwelling on the details, she wasn’t used to having anything inserted in the out hole, so she excused herself for a while. As I lay there, still in a post-coital reverie, still (literally) bathed in the scent of what we had just done, doubts began to intrude into my self-satisified, I’m-such-an-alpha bliss.

*What if she decides she didn’t really like it?*

*What if she decides she liked it but didn’t really feel like she had enough warning that I wanted to try it?*

*What if she didn’t like it but now feels pressured to please me and to…*

The bathroom door opened, and she practically bounced back into the room. I asked her, a little tentatively “Everything okay?”

She grinned and shot back “Do you mean me or my ass?”

And the remnants of the wall between us crumbled. You know the wall I’m talking about, brothers and sisters. The wall that prevents you telling the person you’re sleeping with what you’d REALLY like to do in bed. The wall that means that when your partner summons up the courage to tell you what THEY want, you treat them like they’re a pervert, secretly despising yourself because you know you’re acting out because you feel like you’re sexually inadequate in their eyes.

We didn’t have that wall anymore, and in that moment we were liberated in a way I’ve never experienced before or since. We both already knew that our age difference and our divergent lifestyles meant that a ‘relationship’ was out of the question. It seemed like it was going to a year or so of being FWBs having good but monotonous sex. But from that moment on we had a relationship that was one of complete sexual liberation. As you will discover, if you’re kind enough to read on.

I could immediately tell she felt it too, because she got into bed and kissed me like she wanted me to merge with her. We held each other close in silence, kissing now and then. Hours probably passed, because the sun had started to go down when I felt the first stirrings between my legs again.

She felt me start to swell, and reached to down to coax me into full hardness, lips locked against mine and her tongue in MY throat, which was unusual for us. She pulled away, bent over and briefly took me in her mouth, before lying back again with legs just far enough apart. I entered her, and for the first time in months felt waves of pleasure purely from entering her vagina, without the need to fantasise about anal. We had deep missionary sex, the kind you’d never see in porn because nothing would be ‘visible’, but for the last few minutes we rolled over so she was on top. I was getting close to finishing, I gripped her plump buns hard and pulled her towards me. She lifted her head and looked me in the eye and I instinctively knew what she wanted. I brought my right hand up without speaking, she raised her head and opened her mouth to take the middle finger I was extending towards her. She got it completely slick with saliva and I put my hand back down again. She reached back and spread her ass cheeks and I slipped my finger into her asshole, this time all the way to the hilt, without hesitation. I felt the same thrill as the first time I had done it, but this time without uncertainty. This is what we did now. She locked lips with me again, going “Mmmmmmmmm” every few seconds. Our thrusts synchronised; when her hips moved up, mine moved down and vice versa. I slipped out of her once or twice, but we were like old dance partners, she immediately adjusted on the ‘come-down’ and I went right back in. She whispered fiercely in my ear “Don’t try to hold back”, and she began to squeeze. My cock felt her pussy contract and my finger felt her asshole clench and I complied a few seconds later, cumming in her pussy in a way I hadn’t cum in anyone’s pussy in years, feeling jolts of pleasure that were almost painful.

With my middle finger still in her asshole, and my palm on her left buttock, I pulled her harder down on to me, wanting to push my cum as far into her as I could.

In the past, before that day, she would lie back for a few seconds after I had cum inside her, then head to the bathroom to wash her hands, face and pussy. This time she lay on top of me, with her head on the pillow above my shoulder, nibbling my earlobe. I realised I was gently, almost idly, working my finger in and out of her ass, and she was enjoying it.

“You know how you fingered me the first time, this afternoon?” she suddenly asked, a bit of a glint in her eye. I pulled my finger all the way out of her butthole, a tiny bit of uncertainty returning.

“Yeaaaaah….” I replied, trying to sound nonchalant.

“You didn’t wash it between then and me sucking on it just now, did you?”

I immediately froze, wondering if I had fucked up the chance of a lifetime because I had forgotten about basic hygiene.

“Actually no…” I managed to blurt out, fearing the worst.

“Mmmmmmm, you’re just SUCH a DIRTY boy” she said, before put her head back down next to mine and snuggled up to me with closed eyes.

The wall was well and truly demolished, never to be rebuilt.

Source: reddit.com/r/eroticliterature/comments/ipmf3h/enter_by_the_exit_episode_2_anal_fingering

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