Enter by the Exit – Episode 4 [Anal] [Analingus] [Anal Fingering] [Handjob] [Masturbation]

After [Episode 3](https://www.reddit.com/r/eroticliterature/comments/iq2n0j/enter_by_the_exit_episode_3_anal_first_timer_anal/), we spent the rest of the evening relaxing. A couple of drinks before dinner, watched a few episodes of whatever her Netflix recommended, cleared up and then headed to the bedroom again. I could see she was getting ready for bed, and not in the sexual sense. She stripped naked, stepped into the bathroom and I could hear the sounds of teeth being vigorously brushed. A mundane moment, but I was glad to be left alone with my thoughts for a bit.

I changed into the cotton shorts I kept at hers for sleeping in, and decided to straighten out the rumpled bedclothes. When I lifted up her duvet to fold it, I caught sight of what it had been hiding. My own semen, cum that had spent a few brief moments in her unexplored rectum before gushing back out. In the journey we had just started together, that stain was like our first footprints. I couldn’t help touching it. Of course it was no longer thick and creamy, but had thinned out and soaked into the sheet and mattress below, and I found that cool, damp patch strangely arousing. But I knew how tired she was, and figured that I’d just jerk off in the living room after she had fallen asleep. I settled down on the bed,

Enter by the Exit – Episode 3 [Anal First Timer] [Anal Creampie] [Masturbation] [MILF]

After the events of [Episode 2](https://www.reddit.com/r/eroticliterature/comments/ipmf3h/enter_by_the_exit_episode_2_anal_fingering/), which happened on a Sunday afternoon and evening, we went through what had become our usual Sunday evening routine. Shower separately, get dressed, order food, eat and then I leave once the evening rush of people out for their runs, walking their dogs and shopping had died down a bit. By this time we were not maintaining strict and sitcom-like secrecy, but neither of us saw any reason to give people cause to gossip more than was unavoidable.

The only difference this time is that through dinner, every now and then we’d grin at each other like a couple of schoolkids who’d just secretly made out for the first time on a field trip. As I hugged her goodbye, I said “There’s a lot more where that came from”

“There had better be!” was the gleeful response.

The next day I got a text from her while we were both at work. It was the usual text one of us would send the other on a Monday or Tuesday: “This weekend (wink emoji)?”

“For sure” I replied.

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?*

Enter by the Exit – Episode 1 [Anal Play] [Anal Initiation] [Cunnilingus] [MILF]

***[Anal Play] [Cunnilingus] [MILF]***

We’d been having sex a few times a month for nearly a year. We had done a couple of clandestine weekends away together as well.

She’s a 50 something widowed mother of 2, still in pretty good shape, but something of a recluse. I’m just the 36 year old friend of a friend of the older brother of a friend of her son or something, who ended up at her house at one of those 2 am on Saturday morning, “everyone come over to mine, my mum’s there but she’s cool” plans. His mum was there, and she was okay with us being there, but not particularly ‘cool’. Smiled and nodded, looked like she’d rather be sleeping.