***[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.
I’m something of a wallflower myself, and not much of a drinker. We ended up making small talk, in the course of which she found out that I’m pretty handy around the house. She mentioned a cistern that was constantly overflowing in one of the bathrooms, and I, being a slightly drunk man in the presence of a woman with slightly saggy but still large and attractive breasts, insisted on taking a look at it. It turned out to be an easy fix, just the ball cock needed a bit of a bend put in it. I told her, and the term ‘ball-cock’ made her giggle, and then she looked at me in a certain way, in complete silence. I’m no player, so I sustained eye-contact for just long enough for both of us to realise that we were both thinking the same thing, then dropped my gaze to her cleavage like a horny teenager.
Much later she told me that at that instant something took hold of her and told her that this was a make-or-break moment, and she put her hands on the neck of her blouse and pulled it down. That leap into the unknown on her part gave me the impetus I needed, and I grabbed her by her ample ass and kissed her. I was quivering erect in seconds, like a 16 year old. She kissed me back, with a fair bit of chest heaving. She then tried to pull away, and finally pushed me off, gesturing to the bathroom door which was wide open. Luckily noone was around. With a bravado stemming from alcohol and horniness, I asked her for her phone, put my number in it, and told her to call me when her son had gone back to college.
The next morning I woke up at home with only a mild hangover. I had the memory of the tops of her big soft tits, the feel of her big soft ass and the taste of her mouth and tongue firmly imprinted in my brain, and I knocked one out immediately. Lying there, with cum on my belly, again like a teenager, I thought it was just a one-off encounter that could have ended in a decent fuck in other circumstances. Sighing, I groped about the covers, looking for my phone. 1 Whatsapp message from an unknown contact: “You can take an undisturbed look at the ball cock in about ten days, if you like. LMK.”
And that’s how we started banging. Lots of awkward hurried vanilla sex on most weekends, getting to know each others bodies. Confessing to each other that we both hated condoms, and realising that neither of us was fucking anyone else, so just barebacking from then on. But somehow it reached a point where it didn’t really get any sexier. Comfortable as I had become with her, I couldn’t tell her that I’ve had an anal fixation ever since I learned what sex was. I’d had one girlfriend who was into having her ass eaten and fingered and liked having my cock halfway up her ass while she masturbated, but every other girl I’d been with was adamantly against even trying. Since my new MIAF (Mom I’m Actually Fucking) was a good 16 years older than me, it never occurred to me to even suggest or try anything in the backdoor region. After a few months with her I only wanted to do it doggy-style, so I could see her big jiggly buns bounce, and look at her lovely, still tight and presumably virgin asshole. Pretending in my head that I was in her ass instead of her pussy, just so I could nut. Thus repeating the pattern with every girl I’d been with who wouldn’t let me in the exit.
And then one day she was blowing me while I fondled her ass, and I decided to throw caution to the winds for the first time in my sexual life. I slid a finger between her labia and got it slick with her grool, and then ran the finger up and down her crack, barely pausing at her tight brown anus. She continued blowing me with the usual sounds of both effort and pleasure, so I pulled on her thighs to indicate to her that I wanted to do a woman-on-top 69. She immediately straddled my face, and kept at what she was doing. I tongued her clit the way I had learned to over the last few months, getting an immediate increase in wetness out of her. I tilted my head aside to finger bang her a little, but that was just to get my middle finger completely covered in her natural lube. I went back to running the finger up and down her crack a few times, and then paused at her asshole, gently pressing on it with my wet, slippery finger tip. She immediately sat up, looked back at me, and I could see that she was surprised but not shocked or angry.
“That’s new”, she said, slightly breathless and sweaty from her exertions. I kept my finger tip on her asshole and asked her, with the lower half of my face slick from her pussy, “Do you like it?”.
“It’s different… it does feel kind of nice, though”
“Well you tell me anytime you want me to stop, okay?”
And I went back to tonguing her pussy, middle finger still on her butthole, now pressing a little harder. She arched her back, clenched her buttocks on my finger a few times, perhaps involuntarily and then went back to blowing me. Just the act of touching her asshole, her taboo-hole, her pucker, had me so hard and horny that I had to do some deep breathing to stop myself from unloading in her mouth immediately. I knew I had to make this count, show her I wanted to push her boundaries but would still respect her hard-stops. But I could also tell her asshole was different from the ass of my one down-to-anal-fuck girlfriend. It wasn’t loose, but I could feel it yielding to my gentle pressure. I pressed a little harder, and suddenly the first joint of my middle finger was in! She tensed up, her anal sphincter clenching down on my finger, and she stopped blowing me. She laid her head down on my right thigh, gently wanking me with one hand and licking the base of my cock. She was panting a little but she didn’t say a word. I kept my finger where it was, and went back to tonguing her clit, gently at first. This was familiar territory. Soon I could tell she was on the way to an orgasm, but still some distance off. She periodically tensed her pelvic muscles and her asshole clenched as well, and she was moaning a little – she seemed to be really enjoying it. I pushed a little harder, and two joints of my middle finger were up her butt. This time there was a clear positive reaction, she moaned louder, and wanked me a little faster. I pushed my finger all the way in, maybe a little too fast, because she clenched her asshole tight again and gasped a little, but soon relaxed and continued moaning. She was now rocking her hips on my face so I knew she was getting closer. I thought I might try slowly finger banging her asshole, so started to pull it out a little, but she immediately reached around, put her hand on mine and pushed it firmly back up her ass.
“Don’t stop. Don’t go faster. Keep doing that.”, she managed to bark at me before burying her face in my thigh and biting down on it a little.
She was barely wanking me at all now, but I was almost ready to unload just from excitement. At this point, thanks to my one DTAF girlfriend, I knew what was likely to be a good move. She suddenly went tense and still, she stopped wanking me completely, and squeezed hard on my cock. I kept at her clit at the pace she liked, and then she began to shudder, with rapidly increasing intensity. Her asscheeks were clenched rock hard, and her asshole was gripping my finger like a vice. Her juices were dripping down my cheeks and going up my nose, and at this point, despite her free hand still being on mine, I slowly but firmly pulled the finger out of her ass as she reached the peak of her climax. Her anal muscles which had been gripping my finger so hard, were finally able to fully contract together with her vaginal muscles. She screamed, there’s no other word for it, and pushed down so hard on my face with her crotch that I couldn’t breathe. But I could see the glistening finger sliding out of her beautiful, perfect anus, and that sight, coupled with her gripping my cock like a joystick, made me blow my load too. Most of it must have landed on her back, some of it must have been in her hair as well. I could feel the final rope of cum stretching from the head of my cock to my crotch. She finally relaxed, and a small flood of thin liquid welled out of her pussy and ran over my face, making a wet patch on the sheet on either side of my head. This was new to me. I wasn’t quite sure what it was, but it smelled and tasted of her, of sex with her, of her womanhood, and I was happy.
We lay there like that, slick from each others bodies.
After a while, I don’t know how long, she raised her head and said “That was SO good and felt SO dirty!”
I smiled to myself, and in response, now fully confident in how I was pleasing my woman, I raised my own head and put my tongue right on her asshole. She giggled and moaned, and fondled my head. I french kissed that beautiful pucker for what seemed like an eternity, and then threw my head back, knowing that our sex life was just taking a new, dirty, taboo and interesting turn for the better.
Source: reddit.com/r/eroticliterature/comments/ipkfrk/enter_by_the_exit_episode_1_anal_play_anal