First Time Anal

Published January 15, 2018 by Krystal Minx

Mr Minx and I have an AMAZING sex life…way different and WAY BETTER than each of us had with our previous spouses. His ex almost never wanted sex, and mine only took what he wanted, without ever a second thought on including me in the equation. I was, crudely put, his sperm depository whenever he needed his release, and to make matters worse, he was deluded into thinking real life sex was supposed to be just like what was often depicted in porn.

This included a brief attempt at anal, and of course he had to have it just like his porn-stash idols…without prep, without any lube other than a dribble of saliva, and worse of all, without even considering to engage me sexually or otherwise. Naturally, it hurt like hell, and to add insult to injury, he pouted about how much I wasn’t like all those glam porn girls on screen, eagerly taking him all the way in while constantly moaning for more.

Fast forward a decade later, and Mr Minx is lock step the most caring, giving, and considerate partner I could ever dream for. Not only do we enjoy each other in and out of the bedroom, our desires are almost spot-on synchronized. He is a total giver like me, and both of us care more about the other than we do ourselves, which automatically benefits each of us in the most indirect and wonderful way imaginable.

We aren’t overly kinky when it comes to our bedroom play, but definitely dabble here and there when the location and situation presents itself. We love sex in different rooms, places and positions, including outside and even somewhat public venues when the mood strikes. Being bisexual, we also include others when chemistry flows, and were both in a triad with a third person for many years. That said, anal was one area that we didn’t really approach.

This wasn’t because either of us were opposed to it…and both of us, probably due to our pasts, weren’t really clamoring for it either for whatever reasons. That said, on MANY occasions when MM is buried deep in me from behind as I gripped the bedding for traction, while he slammed into me, he has wedged his thumb into my asshole and alternately fucked both of my holes. Surprisingly, this has ALWAYS felt AHHH-MAZZZING to me, and when combined with the squeaks of the bed, my pre-orgasmic cries of pleasure, and his sexy ‘pillow talk’ about him and another guy filling me up in raw sensual ways, it’s really taken some of our sessions to another whole level.

Since this has been so positive for us, and nothing like I’ve experienced before, I decided to try again the oft-touted, porn-endorsed subject of anal intercourse. I need this – for me – to wipe out my experiences from before to prove that with the right partner, even something like this could be an awesome thing.

In preparation, we started doing more finger play in that area…various positions during regular penetration, and especially nice was when he would give me oral, and stick fingers into both my holes while his tongue delivered its magic to my clit. WOW! The sensations from all those nerve endings being stimulated together always made me cum faster and harder!

After being comfortable with that, we moved onto some toy play periodically, starting with thinner anal beads, and working up slowly to some of my more slender glass dildos. Mixed with plenty of lube, there’s virtually no discomfort at all. Mind you, this process was a slow evolution over months of play, and only happened when both of us felt a desire for this, and more importantly, when my tummy and backside felt up to the task! (Also, as you know, with backside play there’s a lot more involved not only with prep, but cleanup as well, so adding this into the mix brings a bit of additional baggage as well…when your goal is a quickie before sleep, best to steer clear of anal pokage!)

Recently, all I had on was a black lace bra and I was on my knees sucking MM’s cock, something I absolutely LOVE doing. He loves my tits, and with them this close to being bare, he quickly became very hard. I slowly bobbed up and down, while he moaned and watched me intently. What he didn’t know was that I already had inserted a small butt plug into me, one that I’ve been using for awhile to help stretch and get used to. Most of you have seen pictures of MM’s cock, and it’s definitely on the thicker side, which was always a distant concern for this new type of play.

I pushed him back onto the bed and climbed on top, unhooked my bra and tossed it aside, his gaze never wavering, and then brought my tits down to his face. He turned his head and sucked a hard nipple into his mouth, causing me to groan and push my tit harder against his mouth. He bit down on my nub, putting it between his teeth and pulled on it until it popped back out and then turned to my other tit, doing the same. He moved back and forth from tit to tit, sucking, biting and licking.

I pulled my tits from his wandering mouth and moved up to sit on his face, straddling his head using the headboard as a brace with my very wet pussy hovering over his mouth. He ran his tongue from the bottom of my slit to the top, then back again, occasionally stopping to suck and nibble on my lips. As I raised myself up and away from his face, he now saw the shiny object in my ass. At that moment, we shared one of ‘those’ looks and both knew where this was headed – he could tell exactly what I wanted.

I kneeled next to him and we embraced and passionately kissed, almost as urgently as when we first started. After a few moments we disengaged, and I got down on the bed with my ass in the air while he got the lube from my nightstand. I reached back and pulled my cheeks wide apart and he gently removed the warm metal plug that had been readying his place for him. After some tender kisses and touches, he took the bottle of slippery gel and squirted a liberal amount on my rosebud. He slowly pushed a finger in and I moaned out loud, backing up into him. He slowly fucked my ass and then added a second finger opening my hole even wider.

“That feels really good,” I told him. “I want you in me now!”

He squirted a generous amount of lube on his thick shaft and moved into position for my first ever ‘real’ ass fuck, and I was more than ready. He put the head at my entrance and pushed gently until my hole gave way and his cock began to slide in. This was much different than going into my pussy, which yielded with much less effort. I felt some resistance, but no pain, and as much as I wanted him to just shove his cock right in, we both knew that nice and slow was definitely the way to go. He was being overly cautious and I respected and appreciated him for all his concern, as he paused often, allowing my body to relax and accommodate him.

Once the head was in, he pulled his cock back slightly and then eased forward once again. This time a couple more inches slid in fairly easy before I felt the same resistance. He pulled back and pushed forward again, slowly as before, and I felt the resistance give way. Soon, after repeating this, he was able to slowly slide his entire thick length into my very tight ass. We both moaned softly, as he held his cock very still deep in my ass, allowing both of us to get used to the tight and full feeling. I could tell that he definitely didn’t want to hurt me.

With my history, I was surprised how easily my ass had managed to swallow him whole – it was so tight, I could feel his pulse and mine as they began to beat together. “OK, baby, fuck my ass…I’m ready for you!”

He slowly pulled his cock half way out and then pushed it back in all the way…then pulled back again until all but about two inches were in me and slowly pushed back again…then withdrew all the way back until only his head was left in my tight hole. Then he pushed all the way in, and slowly built up a bit more speed. Naturally, I gasped a little with each of his thrusts, but that kind of added to the excitement and newness of it all.

I definitely felt ‘full’ and had similar sensations as needing to go potty, but surprisingly had no pain or discomfort. After checking with me to ensure all was good, he affectionately rubbed my backside and began to pick up the pace and started genuinely fucking my ass just like in those porn videos! For the first time in my life, the feeling of his very thick cock in my tight hole was incredible, and nothing like I’ve felt before. That very thought alone caused a rush of sexual pleasure to go up and down my spine.


He’s always expressed how tight my pussy felt, a benefit of me never giving birth vaginally, but said this was even more so. He got into a nice rhythm, burying himself balls deep with each stroke while digging his fingers into my hips for leverage. I had my legs spread incredibly wide and my right hand was between my legs rubbing my firm, engorged clit adding to the sensations. My eyes were closed and my mouth open as I spewed out nonstop ‘oohs’ and ‘ahhs’ as he steadily fucked my ass.

I felt every ridge, every curve, every loving muscle of his amazing cock, as he slid in and out of my ass. My hard nipples were on fire, and pulsing as he established a nice tender, gentle rhythm. It seemed like only a few minutes before I felt the impending climax come on. My body went rigid as I felt the first wave wash over me, and this spurred on his as well. Between my scream and clenching down on his cock, he began thrusting fast and furious as my orgasm surged thru my body. Then he went deep and still, as his began too. Right at that moment, his balls constricted and a blast of cum shot out of his dick, filling up the dark recesses of my ass with his hot seed for the first time ever. He thrust a few more times, drawing weak cries from me as he completely drained himself into me.

His cum went deep into my ass as my legs shook from the final ripples of my orgasm. When his cock stopped convulsing, he collapsed against me, both of us out of breath. We both went slack and my once-clenched ass relaxed and it took us both a few minutes to regain control of our senses. He softened and very slowly pulled out of me, and as he sat back he watched my well-fucked asshole as it closed back up to normal. As he did, droplets of his creamy load barely made their way out and slid down my crack. He told me later that this was sexier than he could have ever imagined.


We kissed tenderly and cuddled before drifting off to sleep, both of us exhausted from our new exciting exploits. It didn’t take long for me to reach a pleasant decision about anal sex. The careful prep definitely prevented any searing pain that I had anticipated. While not replacing other forms of sex that we both really enjoy, I can definitely see adding more sessions like this to our growing repertoire of possibilities!


15 comments on “First Time Anal

  • Great article. I wish there was more information like this around. As you say porn gives such a false idea of how anal sex (and all sex in general for that matter) work. Take time (weeks not minutes) take care, seduce each other and guys wait till she’s ready and she asks. Fingers tongues, go slow, go gently, make love. Make it divine for both of you.

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