‘Christ, Lottie,’ Charlie asked me once. ‘Where did you even learn to do that?’
The ‘that’ in question, on this occasion, was being fucked in the ass. It’s not exactly a thing I’m always desperate for—I have gone long periods without it, and I can confirm that no major problems, mental or physical, ensue when this is the case—but, ever since I had impulsively asked Charlie to put his cock in there the first time we hooked up, it had become somewhat of a signature act of our relationship, whatever exactly that relationship was.
Anyway, it wasn’t as though there was nothing in it for me. If I was already pretty fond of that sensation of the first entry, that ‘oh my god, that’s my smallest and tightest hole, and it feels like someone’s shoving their whole arm in there’ feeling, it came to be something that I craved more than anything else; just thinking about the way Charlie would slowly tease my asshole with the tip of his cock, letting me feel that same feeling over and over again before he entered me fully, would have me sitting in a warm puddle at the most inopportune of moments. It got to be the case that only those deep-lying, shuddering orgasms would really satisfy me, and I liked the eagerness with which Charlie responded when I told him, matter-of-factly, that fifteen minutes of him licking my asshole, his fingers digging into and splaying the flesh of my ass, his tongue penetrating to the very core of me, was the price of entry.
So we got through scores of those pump-top bottles of lube, rapidly installed as a permanent fixture next to each of our beds. Charlie became happier, at least occasionally, to leave my cunt unfucked, preferring to let me look back between my legs and to watch long, thick strands of sticky fluid paint my thighs pearlescent white, hanging artfully from the peak of my clit until they snapped into a widening damp patch on the sheets. We eventually took the proper precautions and dispensed with the condoms, and he would leave me oozing thick streams of cum, my asshole pink and raw and a little bit sore. And, if I asked, he would lick it from where it leaked into the valley of my ass, and kiss me as he stroked the hair out of my face, his mouth tasting of asshole and cum and the wayward and glassy flow from my pussy.
Well. I got a little sidetracked there. Anyway, when Charlie asked me this—I think on this occasion, he had fucked my ass long and hard, and then pulled out to cum all over my ass and my cunt, and I was playing with it absentmindedly with my fingers—I told him, and judging by his behaviour for the rest of that evening, the answer rather excited him. It makes sense, I suppose, since my introduction to the ass play world would probably run counter to a lot of people’s expectations.
It would be a little perverse to call me a late bloomer, but in some ways I felt it was the case; I spent five years of my life having furtive, irregular, deeply sensible sex with the boy I started dating in school, and it wasn’t until my undergraduate years, spent at what in Britain we call a plate-glass university, that I had my sexual awakening. There were fistfuls of free condoms and uncomfortable, prison-issue mattresses, there were clumsy efforts at styling one’s pubic hair while a harrumphing line formed outside the bathroom, there were drunken, aggressively-tonguey kisses. There was the time I saw a guy getting a blowjob behind a pool table, as though that offered any privacy at all. And eventually there was Lucy, and then things really got interesting.
Lucy wasn’t my first partner at university; nor was she my first female partner, in case you think this is that kind of story. But she was definitely the most memorable. Lucy was tallish and blonde—things, already, that I am not—with amazing curves—ditto—and a wardrobe which was intimidating in its variety. One day she would wear a leather jacket, her cleavage spilling forth from the excuse for a top she wore underneath it; the next a boyish, preppy collared shirt; the one after that a minuscule pair of shorts, fishnet tights and a Beastie Boys t-shirt. She was a couple of years older than me. She also had a sulky, aloof demeanour, the worst case of resting bitch face you’ve ever seen, and saved any flashes of warmth for special occasions and even more special individuals. Literally all of this made me desperate to fuck her.
And fuck her I did. Put briefly so we can get to the good stuff, we hung back after a class, had one of those long, freewheeling, late-adolescent conversations, I was eventually able to coax her into a barely-open-mouthed, nervous semblance of a laugh, and pretty spontaneously we started kissing until campus began to darken around us. We made our way back to my flat, I discovered that Lucy wore Pikachu boyshorts under her pencil skirt (no, really), we fell asleep to one of her confusing Spotify playlists, and at about six in the morning she shrugged her clothes back on and slunk out, like a grumpy cunt.
So, naturally, it happened again, and pretty soon afterwards. It was a Friday night, all Lucy’s flatmates were out, and I was lying naked on her bed. Lucy sat between my legs, her knees folded sideways underneath her, her knickers still on (no cartoon characters this time, sorry), staring intently at my cunt as she explored me with her fingertips. Every now and then she paused to take a sip of her drink (generally, I think, this was bottom-shelf red wine out of a mug), framing, slightly compressing and then freeing her tits between her upper arms as she did. Lucy’s boobs were an absolute marvel, soft and heavy and round, with big, darkish pink nipples. They made me feel like a clumsy teenage boy, so badly did I always want to weigh them in my hands, squeeze them, kiss her sternum between them, suck her nipples while she looked down at me, amused and condescending but with a glow of pleasure in her eyes.
Sometimes, as the weeks went on, Lucy would make me come with practiced, commanding gestures, then lie back and calmly await me to do her bidding, which I would, sometimes taking directions from her, other times slowly and freely licking the large, slick and salty lips of her cunt, her high whimpers of pleasure strangely vulnerable as I neared her clit. But other times she would calmly explore my body with that funny, amused intrigue, her desire mingling with something like fascination, pulling a little roughly at my nipples or, now, probing and splaying my pussy as though amazed that it looked so different from hers.
I lay back and closed my eyes. Though there was something in Lucy’s manner which intimidated me a little, the way she touched me always had me dripping wet, and I sighed with contentment as she drew circles on my clit. Then her finger snaked wetly below the slit of my pussy, into the cleft of my ass, and I yelped a bit.
‘Don’t you want me to?’ Lucy asked.
I said I didn’t know. Over five years with my ex-boyfriend, he had never once expressed any interest in putting anything in my ass. Nor had it come up in any of my university fumblings, and—I did tell you I was a late bloomer—nor had I really been curious to try it out on my own.
‘Let me try a bit?’ she said.
‘Okay.’
A little gingerly, I shuffled my bum down the bed, lifting my legs a bit, not quite sure I wanted Lucy looking malevolently at my asshole. To her credit, she was very gentle; she stroked the outside of my ass with just a fingertip, first going only upward, then switching to small circles. She even deigned to put down her wine mug, and as she applied the thumb of her other hand to my clit, I started to relax. Only after minutes past, Lucy looking intently and carefully down at me, did I feel the tip of her finger make the slightest of explorations inside me. It didn’t hurt, or anything, but instinctively I tensed up.
‘Relax,’ Lucy said.
Again, she gently stroked the sensitive area around my asshole, and I started to like the way it felt, the way it spread a kind of warmth which seemed to flow into and around my pussy from below. When next she eased her finger inside me, I sighed with pleasure; as her finger went deeper, my eyes widened involuntarily at how much, how intensely I felt it. It wasn’t exactly painful, but I was amazed that a single finger could feel so deep.
As gently as she had started, Lucy stopped.
‘Not so bad?’ she said.
I shook my head.
‘How much was that?’
Lucy held up her index finger, and pointed somewhere about half way up her fingernail.
‘What? You’re kidding me.’
‘Mm-mm. Want to try some more?’
‘Maybe a bit,’ I said.
Lucy told me to roll onto my stomach, and I did. Almost immediately, I felt her warm lips and tongue on my pussy from behind, and I gasped. Her tongue was amazingly dextrous, as limber and as precise as her fingertips, and she focused its soft, warm attention on my clit until I almost forgot what she was there to do. Then, a minute or two later, her tongue was on my ass. For a moment, again, my instinct was to cringe with embarrassment at the thought of someone licking me somewhere so intimate, but this felt even better than what she had been doing with her fingers. Again there was that incredible sensation of warmth, of thousands of nerves lighting up with pleasure, and I was amazed at the thought that the girl who, a week ago, I had known only as the bitch from my literary theory seminar, was licking my asshole on her bed.
The sensation was so intense that I felt like I could come from it if only Lucy carried on for long enough. But she drew away, said something about how I had a cute little bum, and started rummaging in the drawer next to her bed. I wondered, with some trepidation, what tool or toy or implement she was about to remove, and was relieved to see it was something very small. I heard Lucy tear something, then felt a blob of something shockingly cold dripping into my ass.
‘Fuck, that’s cold,’ I said.
Lucy said ‘sorry’, and threw the plastic lube packet down onto the bed. It had, I think, some jaunty and inappropriate slogan on it about men’s dicks.
The afflicted area warmed up a little as Lucy started stroking it with the fingers of one hand. I was almost impatient to feel her finger inside me now, and again she didn’t keep me waiting for long. With a slightly wet, lubey sound, her fingertip slid back into my ass, a little easier this time than the first. I still wasn’t sure if Lucy had been teasing me before, but this time her finger felt shockingly deep. The pattern was just the same as before, though: it felt weird for a moment, maybe even hurt a little, and then my body belatedly told me that what I was feeling was pleasure. I started to moan a bit, and I felt Lucy gently twisting her finger, very slowly allowing more of it inside me.
Things suddenly felt a lot better as Lucy again used her free hand to play with my pussy, and it was as though there was pleasure radiating outward from the middle of me, from my cunt and my ass, tingling in my stomach and making my thighs shake. I shivered with delight as Lucy’s finger entered me deeply again, then whined a little when she took it out.
I thought I heard Lucy snicker behind me, and then suddenly I gasped again as something big and wide entered my ass. I’m quite sure it was only two fingers, clamped tightly together, but it felt like my asshole was being stretched all over again. My self-consciousness didn’t exactly disappear, but there was a delicious kind of vulnerability to it, the way I was opening myself up to Lucy in ways I hadn’t to anybody else. Combined with Lucy’s other hand, working tirelessly on my pussy, the pleasure of it all started quickly to overwhelm me.
‘I think I’m going to come,’ I said.
‘I think so too,’ Lucy said, and then seconds later, quietly but strangely sincerely, she said ‘good girl.’
This was more than enough to push me over the edge; my breath caught in my throat and turned seamlessly into a gasp, and then into a moan. The normal pulsing sensation of a deep, long-lasting orgasm felt five times as strong, and I could feel my ass clenching hard around Lucy’s fingers. It felt like my orgasm was never going to end, and it drew from me a series of panting, yelping moans, and I felt as though I was convulsing under Lucy’s hands. As the final throes died away, Lucy slowly drew her fingers out of my ass, which was met with a final whimper of pleasure as I collapsed, gasping, into the thin mattress of her bed.
For only the second time, I was sure I heard Lucy laugh. It wasn’t a remotely unkind laugh. She wiped the lube from her fingers with a tissue and threw it down next to where the lube packet had ended up.
‘I thought you’d like it,’ she said.
Source: reddit.com/r/gonewildstories/comments/i19kdz/1_ignorance_brings_chaos_not_knowledge_or_the