[MF] Fondly remembering my very first time anal experience

Wrote this several years ago…
————————

It’s been a very long time since anyone has worked my ass over. My boyfriend’s not into it, which is fine, but I do remember the first time, when I was an innocent barely 18 year old girl, me and a boy got a toothpaste-style tube of KY and we headed back to his place. It was only our second meeting. On our first, I was so wet with anticipation before even our first kiss that I had soaked my panties completely through. It was maybe the wettest I’ve ever been, aside from the luxurious, wild gushing I later became capable of so many years later. In fact, that was also with someone unfamiliar, a playfully rough man and his delicious, smooth girlfriend.

But that is another story. Back to my boy, the first boy to take my ass. He gave me such good head, which was the first time for me to get licked and fingered at the same time… and patiently, with him listening, feeling for the cues of my body– now speeding up to match my quickening rhythm, now slowing down to tease me, curling his fingers inside me, making me pull his head in closer, demanding, pleading don’t stop, oh please don’t stop. And while I was being consumed in this new bliss, he started sliding just the tip of his lubed pinky finger into my ass.

It was such an alarming feeling at first, even though I knew to expect it. That part of me was so sensitive, to be touched and penetrated there sent a raw electric jolt straight to my core. And he eased me into it, as it was his first time too, going so slowly, little by little, until his whole pinky finger and then, after that, his thumb, slid all the way into my pink, virgin ass. He was gentle, so cautious, not wanting to hurt me even while desiring to take me.

And then I needed more, urgently. I craved his hard cock inside me, just as he craved to fuck my tightness, which he had been too scared to ask of girls before me. He worked on opening me up to take just the tip at first, as I alternately bucked back against him and jerked forward, away from the occasional pain and panic of it when I tensed up too much… until eventually he inched up to sliding his whole cock in and out, impossibly slowly, keeping me relaxed, with his hands on my hips or reaching around to caress my tits, my face, my throbbing clit. We were both almost shaking with the intensity of this new, kinky, forbidden thing.

I don’t even remember the rest, except that this was before any boy had made me or even seen me orgasm and he would remain no exception. I vaguely remember swallowing his cum out of some sense of obligation and the strange adult inkling of intimacy that it gave me. But most of all I remember being an awkward teen, fucking with the music turned up in a room plastered with rock posters and Christmas lights, moaning into the pillows with each slow, deep thrust into my tight ass, hoping his family couldn’t hear.

Source: reddit.com/r/gonewildstories/comments/c01sz3/mf_fondly_remembering_my_very_first_time_anal