I met Hillary at the first job I ever had. She was the admin assistant in my department, so we interacted on an almost daily basis. She was a few years older than me, someone I got on with really well. Dark hair, deep eyes, always smiling, slender, not very "busty" but just curvy enough. I DEFINITELY noticed her. But me being young and new to the real world, I was always trying to be very cautious about my work behavior and relationships and didn't want to jeopardize anything. So although I liked her, I put any thought of asking her out clear out of my mind. However, to be totally honest, from the day I first saw her at work, I most definitely noticed her small, very round, subtly-wiggling-from-side-to-side bottom when she wore certain pants. And I noticed that she wore pants more often than skirts or dresses.
I'm that ass-obsessed guy who used to fantasize about my classmates' bottoms from middle school onward, always mentally undressing my female classmates whenever I walked behind them and especially when they wore tight jeans or short shorts. Always wondering about what happened to them at the doctor's office, wondering if they got examined in the same intimate and shocking way that I did. And I'm still like that today. And Hillary, well she was the first adult I fantasized about after I'd left college and entered the Real World. To be even more honest, in those first months at that job, I lot of my masturbation fantasies involved Hillary and undressing her and imagining playing with that bottom of hers in very naughty ways. I never in a million years thought that I would ever see her naked, in the flesh, her whole body, for real and up close and intimate.
A year or so into the job Hillary and I were talking often, casually, friendly, but not in a flirtatious way. One day I was telling Hillary about a solo trip I was planning to take that summer up to the mountains, not camping, but rather, staying in these little lodges, some would say cheap and musty but they were kind of charming to me, and she told me that she'd spent a lot of time up there with her family as a kid, camping. Eventually she sort of invited herself along on my trip. I just agreed, and I was happy to have her come along. Still thinking very naively, I didn't even put together right away what was happening, or that obviously we'd be spending each night together in a small room, sharing a nearby bathroom. She later admitted she had been very deliberate about all this as the attraction was mutual from the beginning apparently. The first night of the trip was wonderful, talked late into the evening, went to bed, slept in our respective bunks, nothing happened. Dressing, undressing, bathroom activities, all those were done privately, discreetly, undiscussed.
The following day, another great day outdoors, and during the evening chat over wine in the room, she, being older and the more mature and confident one by far, made her move, boldly. We were chatting very easily, now in a slightly flirty way. At one point we were sitting on the floor next to each other when Hillary leaned toward me and looked me right in the eyes and said "I want you to make love to me". She didn't even start at "I want to kiss you." I still have a hard time believing it. My gulp was probably very loud. Soon, after my expression of shock and me not knowing what to say other than "Yes, I want to too", she smiled, leaned in and kissed me. Again, shock. And such a delicious feeling, her lips on mine. And then rather quickly the clothes came off, and then the underwear, and I was in a hazy, floating air of disbelief that this was all happening.
I was so young then. So naive. In hindsight, I can say that it never got extremely crazy sexually that night: a lot of kissing and caressing, my loving to have her small, hard nipples in my mouth, brief oral, she sucked my cock, looking up at me and smiling, ending eventually with missionary intercourse, with the condoms she brought. Both of us were happy but still hesitant. I wasn't a virgin, but still I was nervous. I think this was because I looked up to Hillary, respected her, because she was clearly a mature adult. I didn't want to do anything wrong or to offend her. It was like that for the next few nights, foreplay and gentle vanilla fucking, always with the lights low. Weird, we were so tentative, looking back. And we never discussed what happened each night, neither during the act nor throughout the next day. Not that I was worrying about it. I was in heaven to be honest.
Then, the last night of the trip, again drinking wine in the room before dinner, lights all on, clothes all on, chatting, laughing, and I felt suddenly like I didn't want to wait until after dinner. And what I wanted was to see her body, her skin, all of it, in this full light. And I remember thinking "she and I have been naked for the last few nights and I don't even feel like I've actually looked at her body." That gorgeous body, or so I envisioned. Our encounters had always occurred in a low-light atmosphere. So, I started kissing her. I began taking her clothes off. And she was not in the least inhibited. And then my clothes. She clearly wanted this, liked it. I felt confident. I knew we were getting along very well in general on this trip, that she liked me a lot. I just realized that she wanted this moment, wanted me to fuck her, and that she knew I wanted her just as much.
And it was incredible to look at Hillary in her full, beautiful nakeness. Wow. Can't even put words to it. But honestly, eventually, I didn't hesitate much longer to see what I'd desired so badly. I rolled Hillary over onto her stomach and stared down at her bare bottom. For a long time, took it all in. That gorgeous ass that I'd undressed so many times at work, that I had avoided exploring during those previous nights, that I was afraid to touch too much because she would think I'm perverted if I did, that I was fascinated by, so round and firm and oh god, that shadow disappearing in between her cheeks where just a hint of dark hair was now visible to my eyes. So gorgeous, as I'd long imagined, and yet sat there barely believing that I was actually looking at it. Hillary was of Italian heritage on one side of her family, so her skin was a lovely light brown color, but her bottom was nonetheless fairly pale, distinctly lighter than the rest of her body. Her breasts, too, were lighter, and her nipples were quarter-sized and dark brown. I could see that she had a few moles on her back and some very tiny ones, almost like freckles, on her bottom cheeks and on the backs of her legs too.
I remember this particular night so well now, years later. I lowered my body against her backside, began to lay against her, slowly rubbing my very hard penis against her bottom, in her crack, reaching under to hold her small breasts with my hands, gently pinching and caressing her nipples, kissing and breathing into her neck, smelling her skin, her hair, eventually pushing against her bottom harder, feeling my penis rubbing between her cheeks now. I was used to doing this with my college girlfriend who always let me cum on and between her cheeks. And hearing Hillary moan, a low moan that sounded like pure enjoyment and lust and I don't know what else. Once I heard those real, guttural noises I sat up, straddling her thighs, and looked down at her lovely ass, put my hands on her cheeks and leaned down toward her. I didn't care at that point what she would think. I wanted this.
I gently, firmly pulled her bottom open, using my thumbs, wide, and looked her her anus. And there it was. I just stared at it. I was in a kind of shock, loving so so much to see it, finally, with my own eyes, this thing I'd daydreamed about. Almost not believing that she could even HAVE an anus. My boy brain has never come to terms with the fairer sex actually defecating, but that's another topic. But yet there it was inches from me. I will tell say that, yes, Hillary gasped audibly at this initial, somewhat sudden exposure of her most private place, and her breathing became heavier, but she didn't say anything as I explored her gorgeous bottom. Did not pull away or prevent me in any of way of doing this. She had not showered since the morning, I thought suddenly to myself, but she looked, her anus looked, beautiful. Small, cute, so tender, so clean. It was a "pucker" in that her anus was tightly shut, perhaps due to surprise, shock, embarrassment, excitement, maybe all of those things.
And so I continued looking, staring, exploring Hillary's bottom hole: its colors (brown, a little purple and pink), its wrinkles (not heavily creased but rather faint), the slightly bumpy areas around the rim where the wrinkles were a bit irregular, her dark hairs (not a lot really but dark and all around her hole and some above between her cheeks, though none on the cheeks themselves), her tender skin in her cleft which was a deep pink and distinctly different from the skin of her paler cheeks, and the almost imperceptible movements of that lovely opening as she tensed up and relaxed during this prolonged inspection. I touched her anus tentatively with my fingertip as I held her cheeks open, lightly around the rim. She let me. No flinch or pulling away. Holding her open firmly, pulling her little hole open a bit more with my thumbs, noticing the deep deep pink and red-purple colors inside her anal passage. Amazing, I thought, Hillary allowing me to do this, to see this part of her.
I leaned in further and, obviously feeling bold and just so excited, kissed her bottom hole. Gently, slowly. One after another. OHHHHHHH, if I thought looking at her asshole was a powerful, feverish feeling, well this was another threshold altogether. I could not believe I was doing this, using my lips on her anus in this way. So wrong. But so good. Pulling my head up to look at her little hole, repeatedly. And after who knows how long, and now feeling almost unrestrained in my confidence and ecstasy: I then licked Hillary's anus, just a bit with the tip of my tongue, for god knows how long. Hard to describe the moaning breaths oozing out of her mouth at this point. Circling her tiny opening around and around, feeling her textures on my tongue, eventually pushing the tip in slightly, listening to her gasping louder. In, a bit further, feeling her hole grip the end of my tongue, almost like her hole kissing my tongue. My face buried in her bottom and my mouth connected, so intimately, with her warm, soft, firm asshole. I loved the smell, nothing bad at all, but a very distinct, warm odor that I got to know very well over the next several months. In such a short span of time this evening I felt Hillary and I had crossed some very hard boundaries, moved into a completely new place where neither of us, not me at least and not her I later learned, had ever been. I was still operating in a state of disbelief. And of pure joy.
By this point, of course, I could literally feel and hear and see how she so craved this, just like me. She'd said no words, nor had I. I felt a connection with Hillary now about this fundamental desire, this gut craving. At that point the feeling in my body was beyond intense, like boiling blood. This was such a huge turning point in my sexual life. To meet someone like me, who understood this feeling I'd long had and been ashamed of having. A feeling that had never been reciprocated and obviously that I could not talk to anyone about. Hunched over her bottom, her wide open cheeks, my heart pounding in my chest, I wanted something even deeper, literally and otherwise. I wanted more, wanted to be closer to her, to be inside her, in her ass, to penetrate her *there*. I sat up, still holding her bottom open, my fingertip against her sweet little opening, I asked: "Can I put my finger in?" She replied, still in that gasping breath, "You can do anything you want to me." WOW, I thought to myself. No one had ever said that to me and certainly never in this circumstance. Still somehow tentative and, trying to be sort of "respectful", I said, "OK, I'll just put it in a little bit".
Then I gently pushed my index finger into her saliva-slick anus up to about the 2nd knuckle. It's funny the specifics you remember about some events in life. Her bottom hole held my finger, grasped it tightly. I felt the heat in there around my finger, so so tight and warm, a feeling I'd only felt before when I'd put my own finger in my own bottom as a teenager. Her groaning deepened. In and out very slowly I pushed, as I watched in total fascination, my eyes inches from the open cleft of her bottom. Soon, I sat up where I could see the length of her body, her hair, her face sideways on the bed, eyes staring, sometimes slightly closed and then wide open, and mouth agape, hands grasping the bedsheets, squeezing them at times, so intense, so beautiful, her round bottom open with my finger fucking her asshole. Then leaning in and watching the penetration up close again. The details, those soft pale cheeks with tiny freckles and open pale pink and also slightly purple-hued crack and pulsing brown & deep pink orifice, this hole gripping my finger, the saliva bubbling a tiny bit as I moved in and out of her, the wet dark hairs surrounding her variously colored flesh, and hearing her inhaling and exhaling and moaning all the while.
Being allowed in to such an entirely private, personal area of Hillary's body was overwhelming my young, inexperienced senses. Just earlier in the evening we were simply friends-with-vanilla-benefits, not a bad thing but not much different from a few other women I'd been with in my life. But now, that had all changed. Just knowing how much she actually liked and desired this, desired me of all people to do it to her. 'Intensity' doesn't even begin to describe it. Of course. No words really do, even now. This very naughty, nasty, improper, yet totally irresistible exploration lasted for some time that evening. I have no idea how long it was. In fact, on this night we did not have proper sex, intercourse that is. I don't recall either of us having an orgasm, though honestly I felt like I was on the edge of coming the entire time. That night was only about crossing THAT boundary. Satisfying THAT desire. What we did do that night, after we'd exhausted her ass and my tongue and finger, was talk. We just talked about this desire, this craving, this need, for this part of our bodies.
I remember we were laying there on our backs, naked, side by side, staring up at the ceiling, silent for a long time. Finally she said "Did you do that before?" in a tentative voice. I replied, "No. I never have". My head was racing with things to say and ask Hillary right then, but I couldn't find the words. So just whispered, "Did YOU ever?", assuming that this was also a first for her. She replied, "Me neither." Then she said something that really caught my attention: she said, "The only person I can remember who has seen my bottom like that is my doctor." I wanted to hear more about this. I said "Oh, really, what was that for?". She said it was when she was about 12 years old and had been very constipated and her mother took her to the doctor, a man, she said, because I asked. She said the doctor had her lie on her side on the exam table. And then he pulled her underwear down to her thighs. Already she said she felt awkward and then "all of a sudden" he spread her cheeks and pushed his finger inside her, feeling around inside. Hillary said she was now totally shocked and bewildered as this had never happened to her before, having her bottom opened and examined and, especially, penetrated like that. She'd had no idea what to expect and was afraid to say anything while it happened to her. She said also that her mom was there watching everything, which she said made her feel better because she could see her mom as this exam was happening. I asked Hillary what she was feeling while his finger was insider her bottom, and she mentioned having conflicting feelings: scared and embarrassed on one hand but nonetheless secure because of her mother's presence. She said she was horrified that the doctor's finger would have poop on it but she never saw it after he took it out.
The doctor then told her mother that she would need an enema. Hillary said she had no idea what an enema was then. She said her mom was just telling her to relax as the nurse brought in the full bag and tube. She asked her mom what they were going to do with it, and her mom just tried to calm her by telling her it would make her feel better. Without much discussion or warning she said the doctor applied lube around her hole and pushed the nozzle into her anus and released the water. She said this was also very shocking for her to again have her bottom violated, and also that it was uncomfortable as the water entered, and also she was afraid she would not be able to hold it. But she said she didn't say anything further, though she knows she must have had a scared look on her face because her mother tried to calm her and tell her to let the doctor do this so she wouldn't feel constipated anymore. Hillary said, as we lay there side by side, that the entire enema experience was something that she'd thought about it many times in her life, though never told anyone. That the feelings of shock and embarrassment remained but that they were "exciting thoughts" to look back on. She lay her hand on my bare chest and said she was "so happy", "so excited", to tell me about this.
I didn't ask any more questions, though images of her at the doctor's were definitely in my head now. Her story made me think of my exam at my own pediatrician's during puberty. I felt like this was the perfect time to talk to someone about that very affecting experience. So I said something like, "Hillary, I had something sort of like that happen at the doctor's when I was the same age as you." She said "Oh really?!?! I wanna know!", holding me tighter. I then told her that it was something that happened during a routine annual exam, something I'd never told anyone, that I was embarrassed about. "Richard, you can tell me. You can trust me, you know that, right?", reaching for my hand and squeezing it. Basically I told her about how I lay there face down, 12 years old, as the doctor lowered my underwear, exposing my bare bottom for the first time in my young memory, how shocking that alone was.
And then how my blood and nerves exploded in heat and shame as he spread my cheeks wide open to examine my anus visually. I told Hillary how that made me feel, how I thought about those few seconds, with his eyes focused on my bottom hole, for days and weeks and really for the rest of my life. I told her about how I began exploring my own bottom after that exam, looking at it in a hand mirror when I was home alone, then bending over in front of a full length mirror so I could open my bottom and see my anus more fully. How I began thinking about other girls' bottoms, about my female classmates at the doctor's office, wondering about what went through their minds and the doctor looked at their most private place. And how ultimately I'd concluded that my desire was unique to me and probably wrong, and how I had always felt guilty for my craving, for wanting to look at girl's bare bottom, to caress and feel it, to see her little hidden hole, to touch and explore that forbidden place. As I said all of these things, in more detail that I'm writing here obviously, Hillary finally said, with such passion in her voice, "Oh, yes, me too! Me too!" And she held my arm very tightly, whispering "Oh Richard", and rubbed her body close against me as I admitted all these memories and feelings, occasionally saying "Mmmm" warmly in agreement and support.
After some silence, my heart pounding, I admitted, " Hillary I want you to know that I've wanted to see your bottom so bad since I met you last year." She lifted her head and looked down at my face, "REALLY?". I continued to admit, "I stare at you often at work, at your bottom whenever you walk past." She just kept looking at me with a huge grin. "Hillary, actually, I've pulled down your pants so many times in my mind." It became easier, and more exciting, to be honest with Hillary as the night continued. It was she who had opened up literally to me, and now I was opening up, my mind and thoughts and experiences, to her. It felt so good. And, to use the word she often used, so "exciting".
"OH MY GOD, REALLY??" she replied to my last admission, cuddling in tighter to me, her head now on my chest. I kept going. "To be honest, I wanted to see more than just your bare bottom, but also, um, I wanted to see in between too, Hillary." There, I'd said it. Admitted it. It was silent between us for a few seconds. I continued, "And I loved looking at you like that tonight. Your bottom is so beautiful." Seems weird to write this, but I do remember telling her those words. Hillary gripped me and pulled me close to her and said, in a sort of breathless, breaking voice, "Ohhh, that is so exciting!" and started to half-laugh. "Oh my god, I didn't know there was someone else who wanted this too."
I propped myself up on my elbow and looked down at her as she lay naked next to me, "Hillary, I loved it. Seriously. I loved looking at you like that. I wanted it." I then was even more blunt. "And seeing inside you, inside your..." (I recall a hesitation because I had not yet used this explicit word with Hillary yet) "...your anus." Hillary looked up at me with huge eyes and a smile, and I continued. "And feeling inside you with my finger. And smelling and tasting your bottom too. I wanted to put my tongue in you. I had to. I had to do that to you, Hillary." Her smile grew as she looked down for a moment (like blushing?) and then looking back into my eyes. Hillary's voice was slightly shaking now, sort of giggling, saying things like, "I loved it... I loved that you saw me like that... I was waiting for you to touch me there but I couldn't say it... it's too private... it's so embarrassing." And then she said, "I want to feel it again." (pause, deep breath) I said, "I want that too, Hillary", this time looking her straight in the eyes, instead of up at the ceiling (I can still picture that ceiling with its old style lighting fixture).
As we lay there on the bed, I remember feeling like I was floating. My brain was in the most incomprehensible headspace. Just a short time before all this, Hillary was merely my colleague, my older, very respected, very beautiful colleague, someone basically untouchable as far as I was concerned and, although she was clearly enjoying my company, who I simply never imagined as someone I could ever spend personal time with, let alone kiss, let alone anything beyond that. And yet here we were, side by side, naked, having just experienced, for me (and for her, I was now learning), the single most profound, intense, and intimate sharing of my and our lives. Her voice broke me out of my spell. "But Richard... can I... ask you something?" she said, very hesitantly. "Of course", I said, thinking she was going to continue asking about what I had just done to her, or maybe she would ask more about my doctor, or maybe even my past experiences with other women. "Can I see YOUR bottom?" she asked with a smiling but terribly serious look on her face.
I was taken aback. Honestly, I had not thought of this as I lay there. Despite everything that had just happened that night, despite all my fantasies and solo orgasms about Hillary's ass, not to mention all the bottoms of every woman I'd ever thought about in my nastiest daydreams, despite my shameful craving, since puberty, to submit myself to a women, to submit MY bottom to someone and have them DESIRE to expose and examine and explore and violate me, on, around, and in my own little pink hole. I was surprised Hillary asked me this because it was so unexpected. Only one woman who I dated in college, Ann, ever looked at or touched my anus with a finger. And although she never made me feel bad about it, I could sense that she did it as a favor of sorts, not as something she would ever have done of her own accord. Ann was accommodating but not into it. I almost felt she did it despite her misgivings (though to her credit, she never said "no"). So I still felt much shame and guilt about this fetish, this desire, this need of mine... all of which kept me from thinking of pursuing it. Kept this craving locked away in my head. All because of the fucked up prejudices against a male wanting such a thing and my fear surrounding it.
As a young, virgin teenager I could not imagine asking a woman one day to do any such thing. I used to touch myself there when I was a teen, gently, sometimes with a bare fingertip, other times with a vaseline covered finger, savoring the electric, intimate feeling, imagining someone else doing that to me, imagining a young woman putting her finger between my cheeks and touching me there. I would do this, watching myself in the mirror, watching me violate my own ass (but never looking at my face by the way, such was my shame). But, feeling like I must be the only person in the world with such notions, feeling that I was absolutely wrong and weird and bad to have such desires, feeling like I could never express these feelings to another human being, I assumed and decided that those would remain private desires and private acts, never to be shared with someone else. ESPECIALLY this need to submit my bare bottom to someone else.
Oh but now, Hillary had actually asked me. Asked me if she could see my bottom. But exactly was she wanting? "What? What do you mean?" I responded. A feeling of heat came over me, my gut tightening up yet again. Was I about to submit my own backside to someone else, to my same desires? Did Hillary really want this? I mean, she must right? But do I really want her to? What if she is just saying this because she feels she has to? Polite reciprocating? What if she regrets asking me? What if she thinks my ass is ugly and gross? Anyway maybe I'm not clean, I thought lying there at the end of a long sweaty day. And anyway, I know I have hair down there and maybe that's gross to her. Do women really want guys' asses? Guys asses are not pretty, women's asses are pretty. All these thoughts raced through my head over and over in a matter of seconds.
I said, "Hillary, you don't have to do it. It's OK." Seems ridiculous now of course, but at that moment, I really was hesitant, giving in obviously, an unquestioned reaction, to all those negative feelings and prejudices and, simply, to the shame of admitting that I desired such a thing. Ridiculous because is it not obvious that this lovely woman Hillary WANTS this?! Of course it's the most obvious thing now. Oh, I was so young and naive then. "You don't want me to?" she said, looking a bit confused. And now I saw her own discomfort, her own shame perhaps. Was I denying her what she wanted and what she had assumed I wanted? She was just like me, of course! I here I was pushing her away, making her feel terrible! And my pushing her away like this perhaps confirmed for her that this desire was more "her" and not "we". I felt awful as soon as she said this, and I tried saving the moment.
"Well, um, I mean, I don't want you to think that you HAVE to do something to me just because I did that to you." I was stumbling as I spoke. "Look, Hillary, I mean, it's OK if you don't want to see me... there... I just..." And she sat up a bit and put her hand on my face and cut me off. Remember I said that Hillary was the mature one? She was so amazing how she calmed the situation and brought us back to a state of pure passion and lack of inhibition. This incredible woman's deep dark eyes looked right into mine. "I DO want to, Richard. I've seen YOUR bottom in my own imagination and now I want to see it for real." I was stunned. Didn't know what to say or do. Barely comprehending that this was The Moment. " Hillary..." I started to say, not knowing what words would come next. None did. I was smart enough to know that I simply needed to listen to her, to obey her. To submit to her.
"Turn over for me, Richard. Now. Please." I didn't move at first. I just stared at her lovely face, realizing what she had just said. And the grin on her face got bigger and she said, "I have thought about this for sooo long. I've wanted to know what you look like -- back there -- for a long time." GULP. Deeeeeep breath. Deeeeep exhale. And I rolled over on the bed, watching her face as I did, my bottom uncovered and exposed now to her greedy eyes.
"Mmmmmmmm, ohhhhhh my, yes, Richard. So beautiful, god!" Hillary was now in charge, though she wasn't acting like it. She was just being herself, open, honest in her desiring of this moment. As she said this, my gut tightened yet again and my exposed cheeks felt truly bare, my heart racing, hands gripping the sheets and pillow. I had nothing to look at but the pillow and the wall in front of me. I couldn't see what was happening. I felt entirely at her mercy, submissive to her, and it felt so good and so helpless. And soon I felt her warm soft hands on my bottom, lightly caressing up and down, a bit like she wasn't sure what to do exactly. "Oh so sweet, so beautiful" she kept saying things like this, like I was the most precious person on earth, almost like mumbling to herself. I stared straight ahead as I felt her thumbs tracing along my crack. I don't remember how long she sat their straddling my legs, caressing and looking at me. I recall also hearing her breath and making little soft sounds like "oh!" to herself -- I suppose, like me when I sat above her backside, enjoying the anticipation, the sight of me unclothed and submitting to her entirely.
Without any announcement or talk, her fingers crept into my crack and pulled apart my cheeks. I remember I dropped my head down into the bed and closed my eyes, my fists tight, concentrating on that feeling, that incredible feeling, one I'd felt shame about for so long. The cool air of the room now touched what had been unseen and untouched skin. Private skin, my most private area. And now, oh god, at long last, so wonderful, this was part of my experience, of her experience and of her memory forever, this woman who I could hear breathing behind me as she held me open and looked at that most delicate, intimate spot, my anus. "Richard, you are so beautiful."
Needless to say, I was frozen, and beyond happy, beyond excited, beyond stimulated. It was like my ass, my asshole, was the center of everything. I loved knowing that she was seeing me like this. "Oh Richard, it's so exciting to see your bottom, your asshole, it's open for me. It's so exciting!" Hillary said many such things as she held me open. After who knows how long, after she readjusted her hands a few times, pulling my ass open over and over, she began to touch my asshole. It felt like she was putting fingers or thumbs on it and stretching it apart, I could feel the taught skin, the pulling and prying. I had never felt so open, so vulnerable. "Ohhh, the smooth skin inside... it's sooo dark, so pink!" she whispered, playing and opening and examining me. I was in utter disbelief and delight that she wanted this and was doing this to me. Heaven. I didn't want it to end. Hillary just kept talking and mumbling with something like happiness mixed with shock as she explored me.
My mind and body euphoric and floating, the memory of lying on my pediatrician's exam table years earlier suddenly came back to me: facedown, my bottom exposed, another person's hands on my bare skin, opening up this secret area that really no one should ever see, me feeling totally out of control, trusting the doctor, now trusting Hillary, with something so very private. I had told her the details of that exam, as a 12 year old, just earlier in the evening. It was indescribable to be having those memories flooding through my head as I lay there, as it was happening all over again in a sense, as I knew Hillary was looking down at my open cheeks, as I felt her hands pulling them apart. It was like reliving a memory that had been with me so intensely (but only in my mind) for so many years. I had to share these feelings with her, "Hillary, it's like you're the doctor, seeing me like this. I can't believe this happening!" And she said something like, "I know, I feel like a doctor! It's so amazing to examine your bottom, so exciting to do this to you!"
After some time of Hillary examining me, slowly, patiently, deeply, I was suddenly hit with another shock as I felt her breath and then the tip of her tongue touch me as deeply I could imagine. Not around my hole but right in the deep center of my opening. Of course, this was so beyond anything a doctor or nurse would ever do obviously, so now we entered into a whole new place, together. Hillary did not start by kissing my cheeks and working her way inward, no. She pulled my anus open firmly and went in right where I felt it most intimately, most electrically. I won't bother trying to describe the sensations. Her mouth and tongue then examined every area from deep inside my hole to the outer rim of my stretched sphincter, and all the way up and down the (slightly hairy) crevice of my cheeks. My hair back there, she later told me, did not bother her at all, in fact she said she liked seeing it, as it's "what you really are, Richard". Over and over, with repeated pauses as she lifted her head up, never letting my cheeks close. Had my penis not been firmly buried against the bed, I would have come already. It felt like I was about to orgasm over and over and over.
Again an odd thought suddenly crossed my mind, that twinge of "oh my god, am I clean for her?". Too late for that I figured. This pang was one thing I brought up later when we were discussing what had just happened. I think I said something actually quite crude like, "I hope I wiped myself good", and what I recall was her answer -- she never acted embarrassed or looked away from my gaze -- was "oh no, you looked so beautiful."
And then Hillary continued to push things further, her need (and mine) was so great. "Richard I need to be inside you" she said gently, both of us knowing I didn't need to reply or give permission. It was going to happen no matter what. Not even sure I could say anything at that point anyway. Maybe I nodded my head in reply, not sure. I don't think I did say anything the entire time, beyond grunts and moans. At first, I could feel her fingernail touching my wet, tender opening as she said "Relax for me, Richard". She began pushing in firmly, whispering, "it's going to feel so good." She pushed all the way up to her last knuckle, slowly, but without pausing, though I could hear her breath, "Ohhhh...OH!...Ohhhhhhhh..." It was a very different feeling than just being touched there. It was urgent, big, invasive, tight, impaled, hot. Though her finger was in me, my hole engulfing her finger, I felt that it was me who was trapped, as if she controlled me. I didn't speak but I do remember the massive exhales and UGHs that exploded from my mouth. She continued her breathing and her own moans of clear delight. She later said how exciting it was to see her finger disappear into me, and to feel how very "warm and smooth" it was around her finger. She wasn't exactly fucking me with her finger, but rather, exploring me, pulling it all the way out, tracing a fingertip around my anus, then pushing back in again, sometimes slowly, sometimes quickly (I gasped more than once at that) all the way in. It's like I could feel her looking at this wonderful violation, could feel her eyes right *there*.
At this point my head was really fucked up, spinning, out of control really. I was entirely at her mercy, desperately loving what was happening, wanting it not to end, wanting to do it to her again, wondering what the next step after this is. At some point, we both sort of collapsed and lay next to one another. This night did not end with intercourse or orgasm. Those were not the goals. We were spent. And also I think really we were in a total state of disbelief, not quite believing that this had actually just happened. And we said so to each other, before eventually falling asleep.
The next morning we were due to head home. At breakfast we said barely anything. Yet we ate and could not stop looking at each other, right in the eyes, smiling, both knowing what the other was thinking, which -- we later agreed -- was basically this: "that was indescribably powerful what just happened last night, nasty and dirty and certainly never to be shared with anyone else, and we both know it was right and necessary, and now this is the first time I'm looking at you fully knowing what all of you, your whole body, your most intimate parts, what you look like for the first time and no longer have to undress you in my mind, and I know you are thinking the exact same thing as I am now, and mostly I know that you know that when we get back home, it's all going to happen again because we both need it to, especially after we sit in the car for several hours today not able to touch one another, and that it will happen in the days to come because it has to, the feeling and the act and the submission and the need is too good and too irresistIble for us." We actually later laughed as we realized how frighteningly, explicitly similar our thoughts and desires really were.
Every time after that, when Hillary was feeling her need, feeling dominant, wanting to be (sweetly) in control, she would ask, in different ways and with those pretty, pleading dark eyes of hers, always leading to the same end. "Richard, will you show me your bottom, please?" "Richard, will you pull your pants down for me, please?" "Richard, will you lie down on the bed on your tummy, please?" "Richard, will you come here and bend over for me, please?" "Richard, may I have a look inside your bottom, please?" "Richard, may I open your cheeks please?" "Richard, may I kiss your tight little hole, please?" And so on. I never said no. And I did the same to her when I was "in charge", when I felt Hillary to be in a submissive mood (it was always obvious, as she would hug me and rest her head on my chest and be silent, waiting for me to say something). Each of us enjoyed being at times dominant, at times submissive. And we realized how much each other liked the explicit talking, saying exactly what we wanted to do and were going to do to each other. It was just part of this new sexual life we were now sharing.
Both wanting our "explorations" to continue, Hillary and I agreed to meet for a drink after work a few days later our vacation. Neither of us really wanted to sit in a bar over a drink; all we wanted was to tear each other's clothes off and do naughty things to one another. So we bailed, grabbed a taxi, and headed to my place. As we sat in the back seat, Hillary said, "Look" and opened her purse for me. I looked in and saw a new tube of KY-jelly. I said something like "Is that for what I think it's for?" with a smile. She just smiled back at me and gripped my bicep like she wanted to crush it.
We were quickly naked and on my bed, hands and eyes and lips and tongues roaming all over each other, but Hillary, in her very submissive demeanor, wanted to get straight to me fucking her in her bottom. That's exactly why she went out and bought the KY (I'd heard of KY but never used or even touched it). She reached for her purse and handed me the KY-jelly tube as she turned over to lie facedown on the bed, her legs straight, and her bottom looking oh so plump and delicious, her pale cheeks and dark crack just begging to be opened, and now, also, to be penetrated. I hesitated, wanting to be sure that what I thought was going to happen was actually what she wanted, she glanced back at me over her shoulder and quietly said: "Fuck my ass now, Richard. Please." No matter that I knew this was to happen, hearing her say such things always made it 1,000 more intense. This was, by the way, something I had never done before, anal intercourse. I asked Hillary, "Have you ever done this before?", to which she replied calmly "No". I opened the tube and squeezed some jelly onto my fingers and onto my hard penis.
Then I opened her cheeks with my left hand as I squeezed some jelly onto her very tightly puckered anus, and spreading it around a bit. "Are you ready?" "Yes, Richard" she whispered. Pulling her left cheek wide, I guided my cock into her bottom with my right hand, very steadily and slowly. I was surprised how easily the tip of my incredibly hard cock slipped in, though it was extremely tight. Very warm and so tight. This sight I was looking down at...WOW. I was just an inch or so inside her and didn't move yet. "Is it OK?" I asked. "Oh god... yes. Wait. Mmmmm..." Hillary grunted. "OK, you can fuck me, just be slow." Given how small I knew her anus to be (as most people's are), I went slowly. I remembered very well how my large-handled hairbrush had felt in my own asshole when I was 13, bigger than my own finger. I had told Hillary about that, as we lay together in the cabin up in the mountains, and also about how I later had used candles to fuck myself. And about the times I'd pushed a semi-cooked carrot into my anus, wanting to feel something soft & warm & firm in my bottom. THOSE confessions made Hillary's eyes as wide as I'd ever seen them.
So my cock slowly pushed into her little hole. Then slowly back out. I could hear her breathing deeply. I then did begin to move in and out quite easily and Hillary encouraged me to fuck her faster well before I expected to. We got up a nice rhythm. Really it never actually got fast, just smooth and deep and very warm. I felt so different from her vagina. I only lasted a couple minutes to be quite honest. I mean, watching my penis disappear into her gorgeous bottom, into her now deep pink and stretched anus (and the accompanying intense physical feeling, indescribable) was just too much. I came very hard as I held myself deep inside her, my hips right up against her cheeks. "Ohhh..." she said, something between a grunt and a giggle "I can feel you coming!" I'm surprised I remember her saying that given how loudly I was grunting and almost yelling as I came. The sounds coming from Hillary's mouth were so sweet and intense. I learned that Hillary often got so emotional in these intimate moments that she sort of laughed in a hesitant way, though she actually described the feeling as being on the verge of tears. I later listened to her closely, each time we were intimate, and realized that indeed her sounds were something between giggling and crying, unforgettable noises.
I lay on top of her for some time, my penis soft but still inside her anus. "Hillary, I'll pull out slowly" And I sat up a bit and gently pulled out of her. I remember clearly the feeling, how her anal passage squeezed me out, how strong that muscle really is. I noticed my cock was almost red and very shiny from the jelly (and completely clean, something I'd wondered about). I pulled her bottom open with my thumbs to look at her anus as she lay there silent. It was very pinkish-purple and slightly open, a deeper hue than I'd seen before, and not the tight pucker than I'd noticed up to that point in our very new relationship. "Are you OK?" I asked as I held her open. "Mmm, uh-huh. That felt so full. And I could feel your cum shooting inside me when you orgasmed!" she said with excitement in her voice, and still also that sort of weepy giggle, although she was laying flat out and unmoving, exhausted, as she said it. I never knew or even considered that someone could feel another person coming inside their ass.
Suffice to say, Hillary and I loved anal intercourse from that moment on. And we did it frequently. I can't remember many other times we had vaginal intercourse. Or rather, I know we did have vaginal intercourse because that felt good for us both too, but I rarely came inside her vagina from then on. I sometimes came in her mouth, especially when she was simultaneously sucking my cock and fingering my anus deeply, and, as we learned later, using her other hand to caress one of my nipples. Penis/anus/nipple stimulation is what makes me come like a volcanic explosion, something I first realized with Hillary. But other than that, my orgasms always occurred when we had anal sex, either with Hillary on her stomach (my favorite view) or her on her back with her legs pulled up to her chest. We liked that as we could watch each other's facial expressions and could talk more directly.
The other experience that came to light, that we both soon craved, was me "punishing" Hillary: specifically, me spanking her bare bottom. We were so interested in anything related to making our bodies feel good, especially "naughty things" and especially anything having to do with our unclothed, exposed bottoms, and anything where we could be in dominant & submissive roles.
One night when Hillary was facedown on the bed, and I was gently stroking her skin and basically just enjoying looking at her and touching her, the thought came to me to spank her. I had never been spanked as a child but knew kids who had been, including girl classmates. Of course, the idea of one of my cute classmates being spanked was mind-boggling to my little brain. I never knew if they were spanked bare-bottom but I wanted to assume so, and I also wondered if their dads did it to them and did their dads get any pleasure out of it. Sick, I know, but my teen brain couldn't understand how someone wouldn't get excited looking at these pretty girls' bare behinds. I had come to realize that Hillary liked when I took charge and liked everything I'd done to her bottom thus far, so why not? With no warning, I raised my hand flat and slapped her bottom, moderately hard, not really knowing what her reaction would be. Another women I'd once tried this before I got together with Hillary with did NOT like it at all and let me know it, so I had a little bit of trepidation. Hillary gasped and dropped her head deep into the bed covers, saying nothing, and giving no indication that I'd done anything wrong. No flinch, no protest, no pulling away, no reaching back to protect her exposed cheeks. So I did another. And another. Neither of us said anything. I continued with a few more, slightly harder, her cheeks quickly turning pink.
Then she turned over and looked up at me with a huge smile and held her arms out, so I just lay down on top her and she hugged me really hard. She whispered in my ear, "Mmm, it's good. I like that you did that to me." It seemed to be quite a powerful moment for her. It was pretty intense for me too, but definitely more so for her. I now wish I'd asked why. Was it something to do with her childhood? Had she been spanked? Or was it just the satisfaction of being dominated and of feeling under someone's control or care?. Again, surprising we didn't talk about that, given how open we were about the other aspects of our sexual life. But something told me that she would share it if she wanted and I shouldn't pry. Who knows? Obviously, I was looking forward to spanking her again. And I did, many times. Then one day, in my garage, I found a rattan stick. I immediately thought of Hillary's bottom. I cleaned it off and hit my bare leg with it a few times. Yes, I definitely hurt, a lot. I left it in the bedroom on the chair.
The next time she came over, once we got into the bedroom, I reached for it and made sure she saw me holding it, and I said, "Turn over and pull down your pants, Hillary". She dropped her head, smiled, quietly said, "Yes", and turned onto the bed, face down. She reached under to undo her pants and lowered them, and only them, to her knees. "And the panties", I said. She did not protest but I heard a distinct half-exhale, half-laugh that I'd come to know had nothing to do with laughing: this was Hillary's nervous, submissive sound, a sound she only made when she was feeling, all in one sudden second: excited, anxious, embarrassed, scared, thrilled, almost wanting to protest but only able to emit that faint giggle-grunt. After a pause, she lowered her panties over her bottom. Ohhh, yes, always a lovely lovely sight! I was more verbal than before. I told her that she would need to hold the bed tightly and not to move. I told her that the stick would hurt a lot. I asked her if she was ready. She said "Yes" with a definite *gulp* in her throat. She was clearly nervous but ready for this, wanting this. I methodically spanked her with that stiff, smooth rattan stick. It made a loud "WHACK" on her skin and her light flesh almost immediately turned pink in lines across her cheeks. She never yelled or tried to stop me, but she definitely grunted, louder as they continued, her forearms and hands straining as she gripped the bedspread. I was thinking that it really had to be painful. It sure looked painful. The pink lines darkened as I continued. She later said it hurt much more than my hand, but that it was better, admitting that she liked it more than just with my open hand.
So there was anal sex and spanking, but also, as time went on, we began (or continued, I should say) exploring each other in a quite clinical, doctor-like manner, and, oooh, this was a big moment, began using the bright bedside light as we did so, much like in a medical situation. We never said, "Let's play doctor" (and unfortunately, I did not think to go buy a rectal thermometer, too bad!), and never dressed like a doctor or nurse, but we did use the words 'examine' and 'inspect' and there was always the distinct sense of who was in charge/dominant, like the doctor, and who was submissive, like a patient. On more than one occasion she said, as she would push me back onto the bed, lifting my legs up, pushing my knees to my chest as she knelt down with her head at the level of my bottom: "Ohh, I feel like a doctor, seeing you like this." She liked to say things like this, and I certainly loved to hear it. I often said "I love being your patient, Hillary", which sounds dumb now, but it really was exciting for us both, to admit to being back in our own glorious childhood memories, only how shared with one another.
The first time we used a bright light, it was Hillary who did it. I loved when she took charge! One night, she had already pushed me, naked, onto my back and hunched over me, exploring my penis and testicles, literally examining every square centimeter of my skin, pulling the skin around the tip, looking at the my pee hole, inspecting the wrinkles and ridges on the backside of my cock, gently feeling my balls, lifting them up and to the side, really examining my genitals in more detail than any doctor ever had. Then Hillary instructed me to pull my legs tightly to my chest, now giving her full access to my genitals and also my anus. I watched in confusion-then-horror-then-glee as she moved onto the floor, grabbed the bedside lamp, turned it on, and positioned it so that it was shining inches from these most private areas. Now kneeling on the floor she started to touch my penis and testicles again, basically repeating the exam she'd just done. "Mmmmm, yes, let me see. Ooooh I can see much more clearly now", she said, or something like that. As she caressed even lower toward my anus she said, "I love how this area is textured, between your balls and your asshole... I love these tiny bumps. I love how it gets a bit less hairy there and more again at your asshole." Hillary was so good about describing what she was seeing, something I absolutely loved.
And then eventually, as she always did, she began to explore my anus. On her knees, her fingertips pulling my cheeks wide open, her head lowered, as the bright light shone on me. Caressing, pushing, pulling, opening, probing. She always loved to open me up and comment on the colors and textures, those "tiny bumps" above my anus near my balls and especially "the smooth skin" inside my bottom hole, which she loved to open and touch with her finger, and her tongue, the variation and lightness and darkness of colors, how the wrinkles and creases of my anus disappeared as her fingers stretched me open and reappeared as she released her grip. And of course, she always was sure to penetrate my anus fully, deeply, with one, two, eventually three fingers. Whenever I looked down at her, her face was always right THERE. God, she was so visual, just like me! She loved looking, loved being witness to these acts which were beyond intimate. Looking back up at me from time to time as she told me what she was doing and what she was feeling. And we did plenty of things that would never happen in a medical situation, but that didn't matter to us: we loved the fact that we took turns being "in charge", like a doctor or a nurse, that the other person simply had to submit to whatever wonderful indignities the other could think of. And, oh yes, I soon took my turn to shine that lamp on and between her bottom, wow, you really do see so much more with a bright light close up.
Suffice to say, Hillary and I continued to see each other for some time, several months it was by the end, but eventually I got transferred to another state, and that ended the relationship. I'm not sure that we were ever boyfriend/girlfriend, as we'd never actually stated that our relationship was anything more than sexual, no "I love you", no romantic dinner dates. So the breakup wasn't hard in a strictly romantic sense, but it was in the fact that we were two people who'd established a bond that neither of us had ever had, one based on an explicitly private understanding about ourselves and each other that could never be shared and probably never be repeated. For me, honestly, I've had some intense and intimate sexual relationships but none quite like this one. So it was very difficult to limit, after I left, our desires and needs to our memories and thoughts: we no longer had the physical outlet for them, couldn't touch one another or explore one another or be brutally honest about our cravings and naughty ideas face-to-face.
After my move, we sent each other some hand-written letters. Not messages or emails, for some reason, probably because we didn't want them on our phones. Very erotic, very explicit. This was the only outlet we had, other than masturbation, which we admitted in our letters was something each of us did often as we thought about each other. In one letter Hillary included a printed photo of herself, face down on her bed, naked, with one leg pulled up and her head resting sideways so that I could see the grin she had on her face. She positioned herself just so that I could see a bit of hair between her legs and cheeks, but no more details than that. The photo was taken from above, and I'm guessing her friend Sara (a professional photographer) probably took it for her. That in itself made me wonder what Hillary told Sara about why she wanted this photo taken. Anyway, I can't count how many times I looked at that photo, how many times I've masturbated to that photo. Many.
But one day a letter came from Hillary and she said she had started dating someone seriously, and that this would be the last letter. She was very polite but it was firm. I think she knew it had to be OVER. Honestly I was OK with that. Sometime later, she and that guy got married. After they had a baby, Hillary friended me on Facebook and updated me on her life. We send one another a message maybe once a year, just a real brief update on our lives. I admit that I used to try to read between the lines of her messages to see if she has any desire to discuss what transpired between us back then. But I know it really is over for her, yes, obviously, she moved on. But my memories never seem to.