Anally Submissive Gilly Ch. 01

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Author’s note: The following is a true story, or at least as true as my memories of the girl who had my virginity. I wrote it mostly to get myself off, and I share it here not out of generosity but due to my sick exhibitionism. It is primarily an anal tale, as the title implies. However, subsequent chapters may be listed under BDSM, Fetish, etc. This is a realistic story. It is about raw flesh and real bodies and the psychological genesis of intense sexual fetishes. Later chapters will include no scat play, but will deal with some of the smellier realities of two inexperienced young people experimenting with anal sex. Also, it has not been edited or exaggerated to provide you with a better wank. So, to the offended prudes and the men with flopping little peckers who will inevitably comment—thanks in advance. It kind of turns me on to upset you so much.


After I lost my virginity, it took me only a week to claim the anal virginity of the same girl. Her name was Gilly, and we dated for about two years. Gilly was an odd girl, prone to violent fits of temper, living in denial about the oddness of her family life and of her own predilections. I’m not sure I ever truly loved her. I never felt for her the kind of love I have known later in life, consuming passion or intense affection, but I remember being very attached to her. By the time we met I was frustrated by seemingly endless rejections and missed connections, and I really just wanted someone to experiment with. She, it turned out, was looking for a husband. But experiment we did, and it set me on a lifelong quest for a particular kind of woman: voluptuous, highly feminine, extremely submissive, and receptive in every hole of her body.

I was twenty years old, she twenty-two. We met in an anthropology class at university. It took me most of the term to get alone with her, although she was more than willing from the very beginning. In fact, she had seen me around school and thought of me as “the cute guy,” she would later reveal. The problem was really all mine, though I can’t take all the blame. My school had more than its share of merciless cock-teases, so by the time we met I was almost immune to female signals of interest. No amount of suggestive words or receptive body-language would convince me that a girl was serious about fucking. Even a hand on my naked cock, or for that matter a mouth, meant little to me. When it even got that far, almost always it would end with some real or faked psychological crisis on her part before either of us were sexually satisfied. I could count the times I had cum with another person in the room on one hand. As far as stories went, I got everything from traumatic memories of molestation to the sudden feeling that I was “a brother.” In response I had tried everything short of rape, from sensitivity to macho fits of rage to abject groveling, all of which failed. Although I had never had sex, I was more jaded about it, in a way, than I have ever been since.

Knowing little about women, I was equally attracted to most of them. I liked fat girls, skinny girls, blondes, Asians, big boobs, small boobs. As far as I was concerned, almost anything would do. Gilly was more than all right. She belonged to a sorority, had long silky brown hair, pale skin, and pretty blue eyes. She was about 5’5″, on the stout side and dressed to hide it. We lived in a very body-conscious place, and big girls like her were considered as unattractive as skinny guys like myself. I am still very tall and thin at 32, but in those days I was an absolute beanpole, six feet seven inches of pure skin and bone. I had long brown hair, bleached golden blonde in places by the sun—I lived on the beach—and a deep tan to go with it. Having never seen a man’s erection except in porn, I believed I had a small-to-average cock. The seemingly anti-aphrodisiac effect of seeing it on girls had lately made me wonder if it was substandard. Gilly would soon disabuse me of this notion.

The first time I got truly interested in her was when I was flirting with her—I had decided to be a cunt-tease to match them point for point—after hearing a lecture on primate sexual adaptation. I asked her if she thought Spider-Man or The Thing was more sexually well-adapted. (Yes, in addition to being skinny, I was more than a bit of a dork.) She wasn’t familiar with the superheroes, so I explained about Spider-Man’s super-agility and the Thing’s huge dimensions and dense granite body structure. At the thought of this huge stone cock she made an amazing face—a wincing, puckered look of pain with a saucy grin shining through it. More importantly, she lifted one of her legs off the ground. I had never seen that before, a woman willing to play around with the thought of erotic pain, and I was interested. Jacking off over the next few days, I thought about her and my interest grew. I resolved to ask her out.

The only resistance I met was a series of quaint, “good-girl” boundaries that drew our courtship out over illegal bahis a series of dates. She spent the night with me from the first date on but sex was not immediately on her agenda. At first she was unwilling to undress herself or touch me below the waist, although early in the morning after our first date—because I said it might let me sleep—she allowed me to jerk off as I lay next to her. It was very old-fashioned, almost fifties, her gradually letting me touch her breasts and so on. Throughout the ordeal our making-out was so passionate that I never felt I was being led on. Also the serial nature of it put me at ease, since college-aged cock-teasing usually begins and ends in the course of one night. It turned out that her apparent prudishness had less to do with a (very mild) Episcopalian upbringing, and more to do with her poor body image. I believe she wanted to build up a “relationship” before I could reject her simply for the way she looked naked. She had only fucked one guy before me, a boyfriend that lasted a couple of years, though she was apparently quite experienced in what she called “macking,” a category of activity that went as far as blowjobs but included simple kissing. She had been much skinnier and very popular in high school. She gained weight while with her first “real” boyfriend, who had left her the year before she met me.

I was naked in front of her from the very first night; I knew my skinny body was no great shakes but I saw no point in hiding it. I got a little thrill from spending my evenings naked with a clothed woman—it was strangely infantilizing, compellingly vulnerable—but it was no substitute for seeing her naked. She was willing to satisfy my cock well before she would do the same for my eyes. During this phase she sucked my cock a bit—something she wanted to do but that I wasn’t yet comfortable with, having never received a satisfying blowjob. More to the point, she gave me some terrific hand jobs with massage oil, and quickly became the woman who had given me the most orgasms of anyone besides myself. Not such a great achievement, really, since no one else had previously given me more than one.

I pressured her to “take it all off.” There was a lot of buildup to the first night she disrobed in front of me. I had been an avid student of the naked female form since early childhood, and I was highly excited by the prospect of seeing any girl naked. I knew what night it was finally going to happen, and it occupied me all day long, distracting me from lectures and casual conversations. When we got to the point, in my bedroom, she was visibly nervous, I would almost say terrified. I could see her lower lip trembling. She was wearing a “fat girl” dress of cream and blue plaid flannel, a thing with large round buttons that was tight around her tits but bagged out below them, like a maternity dress. Her fingers shook as she undid those big buttons. Beneath were a bra and panties that I don’t recall, since they were gone in a matter of seconds. As soon as she was naked she lay on her back on the bed, looking up at me with those crystal-blue eyes. I had never before seen such a look of fear, vulnerability, anticipation—a look that ceded all control to me, and asked only for my mercy.

All in all, I liked what I saw. Her body reminded me of art and porn from the nineteenth century, a ghostly-pale, hourglass figure with plenty of belly and a big, lush, brown bush. I saw what I thought were scars on her boobs and hips and asked what they were. “Stretch marks?” she said, utterly mortified. I had simply never seen stretch marks before. Now I realize they must have been “battle-scars” from her sudden transition from skinny to thick. I ran my hands over her body and told her she was beautiful. Her face softened a bit. I asked her to turn over.

Later I would find out that my anal seduction of Gilly began, more or less inadvertently, at this moment. I thought any man would want to see and study his woman’s ass; even as a virgin, I knew that the ass was one of the best parts of a woman. I had read lots of sex manuals and knew I wanted to try anal sex. But my need to see her ass had little to do with this—I just wanted to see her, all of her, naked. She didn’t view it the same way; no one before me had ever asked to look at her ass. By her own account, she thought “Why does he want to see that?” In her mind it was all about her ass being violated for the very first time, and she met this prospect with the appropriate mix of fear and longing and the feeling of sheer exposure.

And she had a lovely ass. Big, round in the profile view, square in the head-on. Flaring out from her narrow waist it was even more reminiscent of the olden days than her frontal view. I was surprised, but not put off, by a dusting of light brown hair at the margins of her deep, dark crack. I was, in short, enamored of her ass. After a long examination of it I asked—really, ordered—her to turn over again. My mouth went right to the pussy, a illegal bahis siteleri nice pink pussy set in the midst of her unruly bush, and I ate and ate and ate. I couldn’t really see her reaction, a fact that remains my main problem with eating cunt. She writhed and I could hear her gasping. My head was squeezed between her thick, plush thighs. When my jaw got tired, I looked up at her, and she said:

“Wow, you’re really good at that.”

And so our sex life went from the clothed to the naked, setting us on a path that led ineluctably to her rectum. As for cunt sex, I was the one who slowed down that adventure. Once or twice, by myself, I had tried on condoms for “practice” and I couldn’t imagine performing, let alone enjoying myself in one. Gilly had already told me that she was very paranoid about getting pregnant and would not let me in her pussy without a rubber. So the first time we tried to fuck I lost my erection at the sight and horrible latex smell of the device. She was loath to try to bring me back, since she said the shrinkage was a sign that I wasn’t “ready.” So despite my grumbling we decided to wait another week or so. Our making-out got kinkier. One afternoon between classes I fucked her c-cup tits, oiling them up and sawing my cock between them from above. The result was one of the most prodigious facials I have ever seen in real life or in porn. I have always been a “big spender,” so to speak. Gilly didn’t mind at all; she actually seemed to like being glazed with my seed, though I imagined it must be a humiliating sensation.

One night, while we were fooling around naked in bed, I asked her if anyone had ever put his finger in her ass. She said no with a surprised but curious look in her eyes. Not knowing entirely what I was doing—totally inexperienced myself—I put my ring finger against her anus. I think the logic behind this choice was that I wanted to use one of my longer fingers, but wanted to avoid the insulting implications of using my middle finger, like “giving her the finger.” I’ve since overcome any such compunction.

I had only seen the female anus, or any anus other than my own, in magazine porn, which by this time (the early nineties) was all hairless. So I was somewhat surprised to find a ring of crinkly hair around her hole. It wasn’t a turnoff, but I was a little disappointed; I had pictures in my head of the beautifully lickable and, I know now, usually waxed or lasered assholes that I had seen so wantonly spread in Club and Barely Legal. I can also say from later experience that her hole was fleshier than most, with a good grip. The hair shouldn’t have surprised me, since I had noted hair in her crack during my inspection of her naked body.

If the feel of the hole was mildly disappointing, the effect of my very long, slim, knobbly finger on Gilly was beyond my wildest dreams. She began to gasp orgasmically as soon as it entered her. To my astonishment the hole felt damp, like a cunt just beginning to get turned on. Encouraged by her labored breathing, I thrust into her to the last knuckle, eliciting one of the muted, high-pitched mewls that were the loudest noise she ever made during sex. If some of this was good, I reasoned, more must be better. So I withdrew and pushed back in more roughly, establishing a pattern of rhythmic stabbing. My force increased steadily as I continued to push and push my finger into her ass. It turned me on, mostly the fact that she was letting me do this, and the submissive way she was taking it. Yet at the same time I was turned off by the idea that I might be touching shit. I looked down and noted no shit color on my finger, but the moisture still puzzled me. I can’t remember whether I was actually erect or not. The display of her first anal pleasure was altogether too overwhelming for me to focus on my cock. In what seemed like just a few seconds she had one of her quiet, gasping cums and her ass expelled my finger. I thought, she is shitting me out. Once removed I instantly brought the digit to my nose.

Gilly was beaming. “Everything okay?” she said. It was very euphemistic, maybe to the point of being irritating.

“It’s weird,” I replied. “You felt wet.”

“Wet with what?” she said, looking astounded. The fluid on my finger smelled like girl, and nothing more. It remains a mystery to me to this day. Those girls I’ve been with since Gilly who were most receptive to assfucking had this same characteristic. Multiple sex books insist that the anus does not produce its own lubrication, but this comes in the midst of warnings so dire (and, it turns out, so easily disproved) that I often suspect sex manuals are underwritten by the lube industry.

“God,” she said, “I don’t think I ever came so fast in my life.”

“Do you think you would like my whole cock in there?”

She nodded vigorously with a sort of manic look in her eyes and a weird, tight-lipped grin. But we both somehow understood that was for another night.

The canlı bahis siteleri loss of my virginity came rather anti-climactically a few days later. I think it was, above all, my knowledge of her anal sensitivity that excited me beyond my fear of condoms. Here was a special girl, I knew now, and more than possessing her I wanted to please her. I still thought anal sex was more of a perverse than a physical pleasure to the fuckee. I wanted her to actually feel good, too, and for that I overcame my prophylactic phobia.

I remember it being a cool afternoon for late spring, and the light in my bedroom, blinds down, being dim and blue. She was up on all fours, ostensibly to aid my inexperienced cock in finding her puss-hole, but also displaying her puckered, hair-ringed asshole in a way that, I know now, was more lascivious than not. I had somehow rolled the condom onto myself and was excited, though not entirely hard. By sheer will I stuffed the semi-flaccid thing into her, and proceeded to stroke slowly in and out.

“Truckin'” by the Grateful Dead was on the radio, and I couldn’t help thinking: “Fuckin’, got my chips cashed in …” The whole thing seemed pretty seventies, except for the condom—the pubic hair, her pale and chubby body, the naturalness of it all. The feel inside her cunt was nice but, through the condom, not enough to make me cum. I was a death-grip masturbator in those days, probably due to my raging frustration; sometimes there would be blood on my hand when I got done wringing myself out. So through the extra-thick latex and bleachy lubricant of a Trojan-Enz, there was little more than a pleasant warmth—barely enough to surmount the discomfort of my dick in the condom.

Eventually I flopped out without finishing. Gilly was her usual quiet self, so I’m not sure what she did or did not feel. It was not until a couple more similar tries that she finally noticed the source of my problem. The rubber was cutting off blood to my (actually rather large!) cock like a tourniquet. We discovered Magnums, the larger size condoms, and had much better results. Eventually what worked best, though it scared her, was barebacking, with me coming on her back or across her fat belly. But this is an anal tale; the cuntfucking belongs in a different story, I think. Except when it was foreplay to the “main event.”

I lost my virginity to Gilly on a Wednesday. She would lose her second cherry to me that same Saturday. Like the unveiling of her body, the date was appointed in advance and greatly anticipated on my part. I understood, from lifelong, avid reading of every sort of fuck book from manuals to magazine letters, that lubrication was required. Being a starving student I opted for a small size of cheap Crisco salad oil, available at my local supermarket for less than a dollar.

She showed up at my door dressed in one of her cutest outfits, a green shirt with white polka dots, a short white skirt, and penny loafers with rolled-down socks. Her makeup was obviously done for a special occasion, including a lipstick a shade brighter than she usually wore. I smiled inside thinking about her at home, getting herself up for the purpose of getting fucked in the ass. I wondered if she felt anything back there as she carefully worked on her image in the mirror. The utter submissiveness of the gesture aroused me immediately—she had actually adorned herself to be more pleasing to me as I thrust my cock in her bottom.

It didn’t take me long to get her naked on my bed with her fat ass in the air. I left her waiting like that as I went to get the oil. I did not plan to leave her in such an expectant and humiliating posture, but I was pleased when I realized what I’d done. I was finding an inordinate amount of arousal in the fact that she was doing whatever I told her to do, that she had submitted already to me sodomizing her, and she would endure whatever it entailed. Now her naked butt, open and obscene, was on full display, waiting for me to assault it. My mind raced at the thought of the things she must be feeling, and the thought of myself as the cause of them.

I returned to the room naked, already half-erect, with a small glass bowl full of oil. She had not budged. A got up on my knees behind her, the oil at my side. I had no idea what I was doing, really. But I did know a lot of lubrication was supposed to help, so I put a whole handful of it on my cock, using my fist to work it up and down the shaft. It was far too much; in the end, my belly, thighs, and sides were completely greased, and my cock, dripping with oil, was purple and rampant to its full extent.

I dipped my index finger in the bowl and pushed it into her anus. Nothing had entered her there so quickly before, and Gilly gasped as I suddenly bottomed out in her rectum. I pulled out and pushed in a few times, enjoying the obscene squishing sounds. All my fingers had, since the first incident, grown quite accustomed to her asshole au naturel, but this was something new. I dipped my finger in the oil and shoved it in again, so a little lube spilled out around her ring. Knowing nothing of how to ready a woman for anal, really—I hadn’t even tried to turn her on with my hands or tongue—I decided she was ready.

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