A Bit of Grey

It is of worthy note, here, good readers, to tell you that it is a rare tale indeed that Grey writes about himself. Yes, Grey's tales are often fantasies and fictions, though make no doubt, every story I write, I enjoy. Often I wish to be the man in them or a mere observer of the events that unfold. Also, do not think that, while fantasies, I have no desire to partake in some of the extreme kinks of which I write. Nor should you think that, at some point, I have not already done so.

But, even if a story I write contains the elements of something I have seen or done, I still do not write my own experiences. Or, rather, I have not until this point. Maybe I will after this, I don't know. Even though I will not shy from proclaiming my perversions - of which there are many and many people would consider some of them most foul - I somehow feel that what I have actually done is for me, not for you, my readers. Maybe this is my flaw as a writer, that I do not reveal my true self to those who would read my stoires, but my own experiences are just that, my own. There have been quite a few people along the way with whom I have shared these things - my partners in crime during them, at the very least, and usually others whom I know to be of similar taste. But, mostly, I hold these memories dear, keep them quiet, and look forward to the time when I meet the right person (people) with whom I can partake of such delicious depravity once more.

But I am breaking that silence with you, here and now. This is not the greatest of my exploits - at least not in my mind, but everyone rates experiences differently - nor is it by any means the most perverse, though again, this is a subjective metric. This was, however, one of those great moments in a life. A stepping stone, if you will, and maybe the first leap into what I have experiences since. The first step is, they say, the most important.

But we must set the stage now. As this is an autobiography, let me take you back some years. I was in high school, a senior. I was not the most 'popular' of people, and I say 'popular' because the word does not describe how many people like you or how well people like you. I was well like in school and had many friends from across the board - jocks, marching band people, nerds, cheerleaders, the druggies, the hippies, and even the sluts. Looking back, I wish I had hung out more with the sluts (being both male and female) as I feel like I could have jumped into orgies and swinging much earlier than I actually did. But despite being well-liked with a versatile group of friends, I was not one of the popular kids. That suited me fine.

So who was I? I was a nerd. I played Dungeons & Dragons - yes, I will admit that, even now. In fact, I will go one step further and admit this: I still do play. I am not embarrassed, and think on this, my readers: D&D is really only practice for fantasies and role-playing. It helps stimulate the imagination, and if you have read many of my stories, I think you will see I have no lack of that. It becomes very easy to play dirty and fall into a role if you have been doing it recreationally for so many years. I found it also helped when I joined a student theater group in college, but that may be a story for another time.

I was a nerd; a literature nerd. I took extra English classes in high school because I liked them. I was chief editor of the school literary magazine when I was a senior. I spent a lot of time working on that. I was not, however, some pale skin, glassed up, brace face geek. I was average - a bit stocky, but held my weight well. Nothing really striking, be it an amazing feature or some wild defect. By all outside appearances, I was a regular student, one of the school's elites being in the college prep classes. Oh, and I should mention, this was a catholic high school so we had the stupid ties and slacks and stuff. Of course, all the girls were in fairly see-though blouses and short plaid skirts. It was a worthwhile trade off in my opinion.

But, unbeknownst to the world, I was, even then, a sexual freak. To give you a little hint, I had discovered porn in my old brother's room when I was 12, maybe a little younger. I was mesmerized by it. Truly, this was the pinnacle of human achievement - pictures of naked chicks! Of course, I later discovered porn videos, which was followed by 'kinky' porn videos - whipping, bondage, anal sex. All that good stuff that is supposedly kinky, but you and I know that is so far from real kink that it's as plain as the missionary position.

The big change of my life came when I was about 14 and I found one of those magazines which is supposedly letters written in by real people. I don't know if it was or not, but the stories were great. There were three stories that changed me, three that I read over and over again. One was an incest story, the first I had ever read, about a brother and sister having sex. Somehow that forbidden act just appealed to me even though I have no female relatives with whom I could have engaged in suck a thing.

The second was a story of a woman being dominated by two men, being told to suck them off, crawl around on all fours, and drink their cum from a dog bowl. I even remember the line - she was ordered to beg for them to fuck her, and she was doing so, though it was done without descriptions in the text, and then the girl says ". . . Or you can just piss all over me and make me lick it up. Whatever you want . . ." I had never heard of such a thing, but damn if that did not send my imagination and teenage hormones into a frenzy. Pissing on a girl and making her lick it up. That was something!

The third was even better. It was narrated by a female who was talking about her wedding night and how when she and her groom got to their suite, she had to piss from having had too much champagne. He tells her to go piss, but follows her into the bathroom. She asks if he's planning on watching, and he says no, but goes in with her anyway. She hikes up her dress and sits on the toilet, only to find him lapping at her now-bare cunt. She tells him to move or get peed on - he says to go ahead. She wasn't sure she wanted to, but had to go so bad it was already trickling out, so she lets loose. He stays there, lapping it up, sucking at her clit and piss-hole. When she's finished and is reaching for the toilet paper to wipe, he stops her and licks it all up himself. She said she was so hot, she just pushed him down and mounted him. She wrapped up her little narration by saying how they still do the golden showers, only it's usually in a tub, and her husband isn't always the one of the receiving end. I never so much wanted an experience to happen to me as I wanted to be the guy in that story.

Golden showers became a particular obsession of mine, and I spent many hours looking at pics on the net (of course, it took hours to look at the maybe 20 pics that were available back then). Lord, each one was more magical than the last, and I had some great masturbation sessions looking at pics of women being showered with golden waters, seeing it fill their mouths and pour across their beautiful tits.

Of course, it is only so long after searching the web for watersports that you will run into a site that also features scat and shit eating. My world expanded once again, and another kink was added to the growing list of things that really got my turned on - lesbians, orgies, anal sex and cum shots had made the list long before.

However, I fear that I may have, in narrating the realization of my sexual 'deviance,' misled you. This story is not about my first scat experience, nor is it about my first experience pissing on a girl and receiving the same from her (actually, I took it a step beyond by drinking down the wondrous nectar she provided). These are some of my best experiences ever, but also some of my most personal. Maybe, in time, I will regale you with these tales as well, but not now. This is the story of the first time I had anal sex with a girl - which precluded the other experiences mentioned above by a few years.

So, I was a senior with a secret - I was a fucking sex freak. In my mind, there was no one around me who liked that kind of thing. I was the odd ball out. I had, for a time, gone through a phase where I thought there was something wrong with me for liking these things, but I had gotten over it by this point. When Sexual Deviance came up in my psych class, I just nodded and grinned as we went through the list and I realized I had most of the fetishes listed (though, gladly, for me they are not fetishes in the true definition of the word).

I had a girlfriend at the time - Mary. Nice girl, very sweet and kind We had been together for a few months before oral sex, a few months later, sex. She wasn't my first, I wasn't hers, but we still weren't quick to jump in bed together. We made sure we knew each other and actually liked one another before then. And, as what happens when you are a teenager, we fell madly and deeply in love.

After we had finally done the deed, I eventually talked to her about anal sex, but she wasn't really into it. She thought it would hurt, and due to a few inexperienced fumbles with the first guy she had had sex with, she had been hurt anally. That whole "wrong hole" joke does happen. From what I understand, he hadn't tried to penetrate, but there had been a few accidental jabs, and those can be a bitch. For all I knew, he was testing the water and found it a bit cold - but I don't know the guy so I can't say for sure.

So, she was against it, but I was hell bent for it. My last girlfriend hadn't been into it either; she wouldn't even let me touch her asshole. That meant that I couldn't even try to woo her into it. Mary was a different story, though. She let me play with her ass a bit, but she didn't let things go very far. But I had a starting point, and sometimes that is all you need.

I wanted to try to persuade Mary into trying out new things. If I could get her into to anal, maybe I could get her into to water sports. I was afraid of mentioning my particular kinks, so I never brought up all those crazy things I wanted to try. I figured all in good time; we'll start small and get on to bigger and nastier things as time went on.

I guess I should mention that I had discovered anal self stimulation years before this, too, so I knew I liked having my ass played with. And this was something I brought up. She would accommodate, sometimes, but nothing very intense. Normally just a little stroke along my ass, if I was lucky, during foreplay. Not much else. Once, just once when we were drunk, she actually rimmed me, which was amazing - I thought I would cum just from that if she had gone longer. She knew I loved it, I had told her so, but she wasn't too keen on doing it again.

It went like that for a while, just some touching during sex, and that was it. Then I made up my mind that I was going to tempt her into it. During sex, when I was doing her doggy style, I would caress her ass, crawling a little with my fingers on her soft ass cheeks, which she liked, and I'd give her a spank every so often. And slowly, over time, I would gently rub the puckered lips of her ass with my thumb. I would suck on my thumb, to get it wet, give and a rub, then wet it again, rub and wet, rub and wet as I was fucking her. I was gentle, but varied my pressure as I did it. Sometimes I would be real light, just gliding over the surface; other times, I would press a little harder, pushing just a bit into her anus.

I did this for a while, and noticed that she sounded more excited when I played with her ass during sex; she would push back against my thumb a little. I knew I needed to go slow, to really rouse her to it, but I had time. I also started rimming her lightly every once in a while. We would be playing around in bed, and I would be playing with her bum - I did that a lot. Grey is a tit man, no doubt, but while the lips are on the nips, the hands roamed the soft flesh of her bottom, squeezing and scratching and spanking. I would flip her on to her stomach and kiss her ass, lick across that delicate skin, give a little nibble, then a spank. I would graze her flesh gently with my lips, and flick my tongue into the clef of her ass, not deep enough to be licking my destination, but a hint of what was to come. I would tease her for a while, make like my tongue was about to sweep through her forbidden valley, then dart away just before it. I would rub her slit with my hand and I did it, getting her wet and horny - she would moan into her pillow as I administered to her, taking my time to bring her to her peek.

And then when her body was hot and ready, when she was feeling her climax beginning to rise, I would spread her glorious globes and bury my mouth between them and unleash my lust with my tongue. I would get hard when I was playing with her ass, but as soon as my mouth locked onto her anus, I was so fucking turned on it was unbelievable. I would kiss and lick and suck at her hole, long tongue-kisses pushing in just a bit with the tip of my tongue, never quite penetrating her. I would lick and lap at her, suckle and moan, and my fingers would work her clit, driving her more and more into her own pleasure until she would be cumming and humping my face, my mouth never leaving her beautiful asshole. When Mary's screams stopped and her hips stopped bucking, only then, when her orgasm was finally spent, would I release her delicious back passage. Then I would mount her and fuck her juicy cunt, normally making her cum again as I did so.

We did this for a few months. I tried to not push it; I would rim her only rarely, and while Mary said it didn't do much for her, she knew how much it turned me on, so she let me. Sometimes, when my passion was high, I wouldn't be able to help myself. My careful plans of not doing it too often would be shot if I was really horny; I just could not keep from feasting on her rear, especially if I had been drinking. Once she surprised me with some new, sexy lingerie - I spent nearly an hour tonguing her ass that night, just because I was so turned on.

Over this time, I began to realize a few things. First, I was sure she was doing things to get me turned on knowing that, when 'revved,' I would rim her ass. Second, the major reason she was so uptight about anal sex was the dirtiness issue. Now, like I said, I was already 'into' scat in that I loved jacking off to shit porn, and I mean the hardcore kind where people were shitting directly into other people's mouths and the receiver was chewing it up and swallowing it. While I had never had someone shit on me or vice-versa, I would have the in a heart beat. I licked her ass plenty of times, getting some small tastes, and really, it just turned me on more. Cleanliness was not an issue for me. Actually, it was the opposite - I liked the idea that it could be dirty! Third, and this goes along with the second one, I noticed that, on those rare occasions when we had the opportunity to shower together, she played with my own ass more, running her soapy wet fingers through my bum, rubbing circles across my anus, and even inserting her finger and giving me a little something extra. So, when the area was, in her perception, clean, Mary had no problem playing around the backdoor. She seemed to like it.

This gave me a few ideas on how best to proceed with my seduction of her ass. Obviously I had been working on it a while, but I had some direction in how to continue. The first step was in the shower where we were clean and she was comfortable. We were soaped up and pressed against each other, gliding our hands across slick, wet flesh. I rubbed my palms in circles over her nipples, making them perk up, excited, then mashed my chest against hers, kissing her passionately and squeezing her ass cheeks between my hands, giving one a hard spank which echoed in the confines of the shower. I slipped a finger into her ass valley and slid it quickly up and down, sawing my way down to her anus and doting on it a bit. She gasped as she nibbled on my ear, her hands raking my back. I loved that, too, and she did it hard, leaving welts across my skin.

"Turn around," I whispered to her. This was no surprise since, when we fucked in the shower, she often bent over and leaned against the back wall as I took her from behind. I slipped my soapy cock up into her ass cleavage, not directly in, but upwards, so that it rested lengthwise in the crack of her ass. I began to pump up and down, fucking her bum like I would her tits.

As I thought she would, Mary reacted with bliss, moaning into the wall as she thrust her butt back at me. She liked the stimulation on her asshole, stimulation without penetration. At first, I think she thought I was just doing it for a little fun before sinking into her, but no, I continued to hump her ass, loving the feel of her butt surrounding my cock. After a few minutes, she got into it, too, and wiggling her ass up and down, clenching her buttocks together around my dick, squeezing in short bursts, then relaxing for a few moments before clenching again.

She was breathing heavy as her pace and pleasure increased, and she just kept moaning more and louder. I was groaning loudly, too, which isn't something I do much. I am fairly silent during sex until I cum, unless of course there is some role playing involved or I'm talking dirty to a girl. But this time, I was groaning like a porn-star and even mumbling out the pointless "Oh yeah" and "fuck, that's good" and the like.

I kept pumping away, my cock fucking up and down between her soft ass-globes, sliding across her puckered ass-lips until I came, grunting loudly and thrusting hard with each jet. My cum exploded out between her ass and splattered all across her back. She was moaning along with me, excited by having my cum sprayed on her. Mary was never a "cum on my face" person, but she knew I liked it and didn't mind if I did it once in a while. It did turn her on a little to have my cum sprayed on her, and if she was already really excited - as she was now - it got her very hot.

Now finished, I sat down onto the slow underneath her and lock my lips onto her pussy, which was sopping wet. Yes, we were in a shower, but it's very easy to tell the difference between water and a juicy cunt, especially with your tongue. It only took a few minutes of going down on her to get her cumming, she was so turned on. We rinsed off, dried each other, and then went back to her bedroom. She was wild with lust and pushed me down on the bed the moment we got to her room. She climbed up on me and let her cunt engulf my cock. Mary usually preferred me on top, but when she was really turned on now and wanted to give me a special treat, she was quick to mount and ride me wildly. She went quick and hard, bouncing up and down with abandon, like a girl on a bucking horse. I always loved it when she got on top. We fucked hard and long a few more times before we had to stop - we had to be wary of her parents coming home. Needless to say, we had a great day, some hot sex, and I had confirmed that she was very responsive to anal stimulation when it was clean. She had been really turned on by my fucking of her ass crack; I knew what the next step would be.

And so I planned, prepped, and waited. When we had the time, I still would rim her, and when we showered, I would pay even more attention to her asshole, and her to mine, I was glad to say. We were slowly steeping up the backdoor action. It wasn't until spring break that I got to put my plan in action. But it was worth the wait.

Now, high school spring break is not like college spring break. We didn't have the money to go anywhere cool and we weren't hold enough for anything interesting. I have an aunt, however, who knows a beach house that was only a couple hours a way. Now, March is not the time of year to go to the beach, not where I live, but it is a great time to spend a weekend at a beach house with just your girlfriend and a fire place. And my aunt's very well-stocked liquor cabinet, to which we were welcome. Her parents thought she was going down with some female friends to one of their beach houses for the weekend, and while not happy about it, they let her go. My parents knew we were staying there together but they thought that we had a group going. I don't know if they thought that was 'safer' in some way, that we wouldn't have sex if our friends were there, maybe they just thought we were abstaining. Or, maybe, my parents were cooler than I ever gave them credit and they knew exactly what Mary and I were up to and they didn't try to stop us, knowing that, in truth, they couldn't stop us, only make it more difficult, which didn't help anyone.

So, there we were, that first night of the three we would be there together, sitting in front of a roaring fire, me leaning against the sofa, her leaning back against me, her head on my shoulder, and my legs stretched out around her body. We were sipping red wine and watching some movie we had rented. It wasn't porn - I hadn't gotten Mary to that yet, sadly - but it was about as close as movies can get and still have a real plot. It had nudity in it and movie-sex, which was enough to make it slightly arousing, but it was also watchable, which was good.

By the time it was over, we were both a little loose and really horny. I had, after all, been groping Mary with my free hand the entire time, as I often do. Gently massaging her boobs through her shirt, casually, too, like it was just something that happened and was in no way out of the ordinary, and she was moan softly as I did. She could feel my cock poking into her back, and when she shifted her weight, she did so with more wiggle than was actually necessary in order to grind her body against my hard-on. We often played like this, and when the movie was over, she turned towards me and we began making out in earnest.

I won't go into details; really, foreplay doesn't come out to well in text, and I have described far too much of it already in this story. Foreplay is something that comes across much better if seen, and best if experiences. Telling you how we kissed, how we touched, the way we moved ourselves as we reveled in our desire will still not be able to convey the fire and lust with which we did it. So just know that we spent a good long time kissing and groping, slowly stripping each other of our cloths, and then licking and nibbling the exposed flesh. Your mind will do the work that my words cannot.

We made love on the floor in the living room, and by that I do mean love - for we were deeply in love. It was the slow, passionate sex, the kind that can last hours, the kind that will bring tears to the eyes as two bodies gently thrust against each other. The type of sex had in the soft light of candles or, as we were, bathed by the warmth and crackles of a fire. We were spent and naked on the floor afterwards, holding each other close and glowing from the passion and love and heat of the moment. We poured some more wine and reclined together, talking in whispers of nothing really important, but understanding the importance of the moment.

But we were horny teenagers and such moments did not tend to last with us. As the afterglow of out mutual orgasms began to fade, our desire was on the rise, and soon our relaxing was over and we were at each other again, but without the tenderness of before. I was dripping wine across her body, I remember, and licking it off. She was shaking with mounting lust, loving it. I poured the wine across her breasts, sucking it as it streamed down her tits and across her nipples. I drank it from her naval and licked up the streams that rolled down her flanks. I poured thin streams down across her shoulder blades and lapped up the pool that formed in the small of her back.

And finally, both of our lusts peaking, I poured a little wine across her ass. I sucked away the red rivers from her butt cheeks, then moved tongue up and through her valley. Her body shivered as I licked at the merlot in her bum. She spread her ass cheeks with her hand, giving me full access to every drop. I held my mouth at the base of her crack and tipped the bottle, sending a small stream flowing between her pale globes, across her anus, and into my mouth. She purred as I drank it up, and then I licked her ass clean, giving her anus much more attention then it needed, but much less than I wanted to give. It was a quick rimming - at least relative to the amount of time I usually spent there - but it had us both extremely turned on.

As I said, we were both already pretty loose from the alcohol, and I had just drank down at least another quarter of the bottle. I can hold my liquor, always could, but I had worked up a fine buzz, and that always lowered my inhibitions. I'm already a pretty uninhibited guy, but I tended to shy away from my kinks lest I scare someone. I shied less when drunk, which, as I said before, usually led to me sucking and licking for a good deal of time at Mary's ass. Not this time, though - this time it pushed me to take the next step. I had been a little nervous about how to proceed, but with the wine in my system, my courage was inflated and I plunged right in with my plan.

"I brought us a new toy," I whispered to her, anything louder seeming somehow inappropriate in the current situation. Her eyes lit up with delight; she knew I had an older friend who worked at a sex story who would purchase vibrators and dildos for us. She had loved the ones I got for her, especially when I used them on her. The bag with our toys was near at hand, so I went for it. "It's not what you expect," I explained, trying to soften the shock. "And you can say no; that's fine. I don't want to push you." She knew that, I had always told her that there was no pressure and I never wanted her to do anything that she was not completely comfortable with.

I pulled it out, and her eyes revealed her confusion. It was definitely not what she had expected, and she wasn't sure at first what it was. I was a bit embarrassed to admit it, but like I said, my buzz was lending me some courage, so I just said it. "It's an enema bag." Then she was a bit embarrassed, too, and a little taken back. I kept talking so as not to let an awkward silence kill the mood. "I know you ware a little worried about . . . cleanliness when it comes to . . . anal play. I thought, maybe, with this, you would relax and not worry so much about it."

She was thinking, I could see it. "You can say 'no,'" I assured her again, caressing her leg with my hand. "But I know you are more relaxed in the shower; you get a lot more out of it. I thought you would enjoy it more after this."

She smiled at me, then, and I relaxed. "Okay," she replied. "I'm not really sure how to . . . um, do it, I guess."

"I do. I'll help, if you want."

She finished off her wine. "I thought you would." I stood and helped her to her feet. She was actually more wobbly than I was, and I thought that maybe the alcohol was lending courage to her as well, and maybe she would have declined had we not been intoxicated.
I led her to the bathroom, which was fairly large as bathrooms go, and had a sizable tub. I ran the tap to get the water warm and instructed Mary to kneel on the floor and bend over the side of the tub. She did as I told her, and her ass was jutting out. She gave it a wiggle, so I gave it a smack, and she giggled as she looked up at me. "You like me bent over the tub, Grey?" she asked, wiggling again.

I nodded. "Yeah. I like staring at that pretty ass of yours." I filled the enema bag and closed off the top. I had gotten a bottle of lube from my adult-story working friend, a big one, too, figuring if this enema trick worked out we might be using it for more later.

I lubed up the small nozzle for the enema tube, then had Mary spread her ass for me so I could lube up her ass. I took my time, rubbing the slippery liquid around her hole, gently pushing in to her puckered entrance to slick up the insides, but just a little. I was very careful and thorough. She was panting a bit under the administration of the lube, and I used my other hand to caress her cunt to keep her aroused and pleasured.

When I thought she was ready, I took the tube and rubbed it across her asshole, letting her feel the instrument that would be penetrating her ass. It was barely thinner than my index finger, and the tip was flared just a little and rounded. She was cooing again, gentle pants of pleasure. I tell her that I'm about to insert it and she should push out. I saw her anus flare and open before my eyes - god, I wanted to drive and start licking away at her open asshole, but I refrained. I did drip some more lube on her ass and the started to insert the tube, whispering about how she should just relax and enjoy the feeling of it entering her.

She did enjoy it. She sucked in a long deep breath and held it for some time, releasing it in a long, low gasp of pleasure. I went slowly, pressing the plastic head into her welcoming anus. It moved in with ease, disappearing deeper into her body. I kept adding little drops of lube to the tube as it slid inside of her, making sure every bit was coated. I wiggled it a bit in her, a small twist now and then, all of with caused her to shudder and moan in delight, much to my amusement. So I decided to very gently fuck her ass with the tube, pulling it out just a little and then slowly sliding it back in, all the while drizzling more lube down her ass valley and into the enema tube.

And her moans continued to belay her pleasure, urging me on. I played with her ass for a few more minutes, pulling the tube out just a little more each time, but it was still a very shallow fucking. Her breath escaped her lungs in ragged sighs until she gasped out, "Is this turning you on?"

"God, yes," I muttered, shifting my body so my hard, hot cock was pressed up against her leg.

She was looking back at my face, a smile on her lips, as she mumbled, "You're suck a pervert."

I grinned back at her. "You knew that before now." I decided I had played enough for now, so I hooked the enema bag on the edge of sink. "Are you ready? I'm about to open the valve."

She sucked in another breath - she seemed to be enjoying just the penetration of her anus even without me playing with it - and she nodded. "Yeah, I'm ready."

I turned the knob and watched as the water flowed down through the tubing and into her ass.

"Ooooo," she purred as the warm water began to flood her insides. She closed her eyes, her head tilting back and rolling to one side and then the other as she mumbled her delight. "Ah, that tingles."

"Does it feel good?"

"Yes. Yes, it really does. It feels very good. Warm. Ahhh, yeah." Her body shook slightly as shiver of pleasure passed through her.

I moved, stepping into the bathtub and kneeling in front of her. She opened her eyes to see me presenting my cock to her. I was hard, my cock feeling like it was swelling so hard it was about to burst. She looked into my eyes for a moment, her lust visible; I'm sure mine was even more so. She lean forward, her lips wrapping around the head of my dick, and I leaned into her, pushing a few more inches into her mouth.

It wasn't a long blow job, but it was spectacular. I was surprised when I didn't bust my cum down her throat the second I was in. She sucked and bobbed her head along my shaft, blowing me with great enthusiasm than I had ever known. Every stroke of her lips across my rod threatened to unleash my cum, but I strained to hold back, wanting it to last. And I succeeded.

What ended the incredible joy was Mary removing her mouth from my cock and saying to me, "Grey, honey, I think I'm . . . ah, I think I'm full." She giggled; it was so cute and sex at the same time. Her ass was full.

"Okay, babe," I whispered to her, bending down to kiss her on the forehead. I got out of the tube and knelt down behind her, running my hands all over her ass, even giving it a quick spank and sharp nibble before I started to pull the tube out. Again, I was very slow, making sure to not ruin what was so far a very successful evening. It came out easily, I was glad to see, and her ass released the nozzle and closed back up, sealing the warm water up inside her rectum.

I caressed and spanked a little more before she said, quite urgently, that she really had to go and couldn't hold it much longer. To my dismay (though not unexpected), I had to leave the room then, my last site being her sitting naked on the toilet, ready to expel her enema. I would have loved to have stayed in there, to have presented my cock for her to continue sucking as she evacuated her bowels. Or to even have knelt before her, spread her legs, and lapped at her cunt while she sat on the toilet and unleashed her enema into the water below. I knew she wasn't ready for such things, but I couldn't help but imagine each situation, flipping between the two as I slowly jacked my cock. I could hear the faint sounds of her expulsion through the door, and that only added to the orgasm that I could feel coming on. I was very careful to not jack too hard or fast; as turned on as I was, it was difficult to keep from cumming.

It felt like a long time, but it was probably only a minute or two before I heard the toilet flush and the door open. I think she was surprised to find that I was right outside the door, but she was smiling up at me and suggested that I give her another.

I was delighted to hear that. Not only had she liked it, but she wanted to repeat it! So we did. I took even more time to lube up her ass, pushing my finger a little inside as I did it, giving her a quick fingering, which had her gasping and moaning. Fucked her longer and harder with the tube, and she groaned even louder and swayed her hips in time with my thrusting, pushing her ass back against the tube. She was really getting into it as was practically begging for me to unleash the water into her bum.

So I did as she asked, then climbed in in-front of her and had her suck me off again. She went slow, keeping her lips loose and only flicking her tongue lightly along my shaft. She knew I was ready to burst and was teasing me, keeping me going as long as she could. And then, with no warning at all, she started to suck in earnest and really fucked my dick with her lips. The shock of the sudden shift in pace put me over the edge and I literally shouted as I came, filling her mouth with jet after jet of my cum. I had never felt such pleasure as wave after wave rippled through my body. I just kept spurting, and each blast seemed long. For a second, I feared I had lost control and was pissing down her throat.

She tried to swallow, but bent over like she was and totally unprepared for the amount that spewed out, she couldn't. Globs of spunk were splattering across the basin of the tub, but it didn't matter. Hell, I barely even noticed.

When I finally came down from my ultimate high, she was still gently sucking on my cock, drinking down the last drops that oozed out. I was panting, completely out of breath and still a little dazed when she informed me she was full. Needless to say it took a few moments for me to compose my self and set about releasing the enema tube from her clenching hole.

Once again, I had to leave the room as she released her bowels, but that was fine. I was still feeling the afterglow of my orgasm. The break in the action gave me some time to settle. I noticed that my cock hadn't settled at all, though; I was still rock hard.

There was the flush again, and then Mary emerged from the bathroom. She said nothing, but took my hand and let me to the bedroom. She climbed up onto the bed on all fours, her ass facing me. She was wiggling it as me and smiling back at me. "Come on, Grey. Don't you want to lick my ass?"

I recall very clearly that I don't recall how I got from the doorway to her ass. It actually sticks out in my mind because my lips were sealed around her anus and my tongue was flicking along the wrinkled skin of her asshole and the only thought in my mind was 'how the hell did I get here?' It was like her words somehow transported my body to her and then I was there sucking away. It's funny, really, the things you remember - that one stray thought. It's locked in there forever - the memory of this perfect moment will always be punctured by that one thought of 'how did I get to her ass?'

But I was there, licking and sucking away like I never had before, and I had always rimmed her with enflamed lust and wanton desire. But this time, it was maddening; I was feasting away like never before, like a starving man attacking his first meal in days. And my fervor was only excited by Mary, herself. She was humping my face with her ass, which was new, and she was much louder than ever before during such activity. More than moans, she was actually vocalizing her pleasure, calling out my name and telling me to lick her asshole. "Lick it, Grey," she cried out. "Lick my ass. Yeah, lick my ass!" That spurred me on, of course. I still get hard when I think about her saying it - I can still hear her voice. God what a turn on.

She screamed and humped against my mouth, and I continued to tend to her anus, sticking my tongue as deep as I could into her anus - which most of you may know, if not very far. Tongues are not long, nor are they particularly hard, so penetrating such a tight opening is not easy, but you can get the tip inside and wiggle that around. And that got quite the reaction from her, making her legs shake and her ass buck. I felt her weight shift on the mattress, and then I felt her hand on the back on my head, pushing me deeper into her ass. She had risen onto just her knees, which did cause her ass cheeks to clench a bit and squeeze my face. It also made it more difficult to lick at he, but her hand pushing me into her helped, and it was amazingly erotic. For the first time ever, she was urging me on more and more, and it just made me insane with desire. I think she came from my rimming her from the way her body shook and the sound of her voice - I regret now not having asked about it at some point, but I didn't. I believe that she did, and for me then, it was enough.

As she calmed down, whether from an orgasm or just and intense explosion of pleasure, she fell back onto her hands. "Do you want to fuck my ass now, Grey?" she asked, her voice low.

She wasn't much for using such language, really, and only said things like 'fuck me' and the like when she wanted to turn me on or during sex. The things that girl said during sex was actually astounding, especially since she never remembered after. She couldn't tell you what kind of noises she made or even if she said anything at all, but she was pretty vocal during the act, which I found very sexy.

I was shocked, and it must have showed.

"That's why you gave me an enema, wasn't it? You wanted anal sex. You wanted to fuck my ass. I'm ready. God, I want to try it so bad. Please, Grey, do it. Fuck my ass."

I will say this, and I'm sure it will come as no surprise to anyone who has desired something so much as I did this and then had their wish granted: there are times I jack myself off just to the memory of her voice saying those words to me. Over and over, "Please, Grey, do it. Fuck my ass." As far as I'm concerned, it's still one of the hottest things a woman can say, her begging you to fuck her in the ass - right up there is having a girl begging you to piss on her tits and in her mouth. But this being the first time I had heard such a thing, it had a remarkable power and potency that every instance of it since just does not possess. But I am digressing again.

I regret that I had to rush back to the bathroom to get the lube, but I must admit that I don't think I had ever moved so quickly in my life. I was lubing her up again, dipping my finger into her tight shitter as far as I could to really grease up her insides as well. I coated my own cock up real slick as well, and rubbed the head up and down across her asshole, loving the way the textured flesh of her anus felt against the sensitive head.

"Please be gentle," she whispered, her voice tinged with nervousness. I could tell that, despite her desire, she was still scared. She had liked everything I had done to her ass so far, but the memory of the pain that can result from carelessness was surfacing.

"I will," I swore to her. "If it hurts at all, tell me. Just tell me to stop, and I will." And I would have, too.

I eased in slowly, and I felt her ass opening as she pushed, just like she had with the enema tube. "Lean back into me," I whispered. I was caressing her back and ass gently with my hands, making sure to keep up a level of contact, of intimacy. While this was what I wanted, I wanted the experience to be wonderful for both of us, and I knew that touching her not only helped her relax, it made this more endearing.

She did as I instructed, leaning her weight back against me and pressing her ass against my cock. I held still, my hands on her ass to help ease her back. There was a bit of strain as she pushed back, the very tip of my dick pressed into the tight, puckered hole; I could hear her tense up and suck in a deep breathe. I rubbed my hands gently across her body, urging her to relax again, and it a moment she did so and I could feel her anus pulse open and begin to accept my cock.

There was a fierce hotness on my cock head and a hard tightness that was slowly giving way to soft, velvety pleasure. We were moving very carefully, letting her ass absorb my cock a piece at a time. I was in heaven! It was absolutely amazing feeling the warmth and tightness engulf member, and every bit that slid in to her ass made me moan in delight.

She was fairly silent, and I was afraid that she was hurting herself but was continuing for my pleasure. While I would appreciate such a sacrifice, I did not want that. Over the course of several minutes, sometimes with a short pause for her body to adjust to this new intrusion, I penetrated her rear, and her butt cheeks met my thighs, then pressed tightly against me, gobbling up every last bit of my dick until it completely stuff deep inside the hot confines of her body.

At last she sighed, almost as in relief, but she mumbled, satisfied and elated, "I took it all!"

"Yeah," I whispered in return, unable to come up with anything better to say.

"God I feel so full," she said. "You feel so big inside me! So tight! Does it feel good?"

"Fuck yeah! So good." Then, much to my surprise, I felt her ass constrict hard on my shaft, squeezing with all her might. It was a quick burst, but it made both Mary and myself groan. "That feels great!"

"Yeah," Mary replied, giggling between pants. "It feels really good. But so big." I could tell she was worried about do anything more just holding me inside of her, afraid it would hurt. She started to clench her anus, squeezing tight just for a moment, releasing, then doing it again, over and over. Neither of us moved, holding completely still as if doing otherwise would ruin the magic of the moment, and she squeezed my cock with her ass in quick, wondrous pulses.

Finally, she spoke again, breaking the drone of constant moaning that had been resounding from our chests. "Spank me," she requested. She did that often - she had always been one for a good spank. And I did so, slamming my hand hard against her smooth flesh. The vibration teased my cock, and I felt her anus and cheeks clench from the impact. It was incredible! I did it again, smacking the other buttocks, and got the same reaction.

"Oh god," I mumbled. "That feels so fucking good!"

She leaned forward, her ass slowly releasing my shaft, but only an inch or so, before she leaned back and engulfed me completely once again. My entire body quaked from the pleasure of it, while she let out a long groan as her ass slid back to meet my hips. She waited a few moments, pulsing her ass rapidly on my shaft, then leaned forward once more, a little further this time before sliding back down again. I let her go at her own pace, not wanting any inference on my part ruin this for her. She continued this way until she was pulling nearly all the way off my dick before driving her ass back against me with a fairly quick stroke. Each time, we both gasped and panted, enjoying every second of it.

"Mmmmm," she sighed. "I'm ready. Fuck me, baby. Fuck me hard."

While I had been enjoying the slowness of our first anal experience, I had to admit that my instinct was to take over and pound away until I exploded. I was patient, knowing that it was by far the best way to go about it, but now that I had permission, every animalist instinct roared to life, and my hips started pump away with all the vigor my body could manage.

I think at first my intensity shocked her, for she tightened up for the first few strokes of my cock in and out of her ass, but soon she was completely relaxed again and screaming into her pillow. Her bucked with all the weight of her body, throwing herself forward, and then back at me, riding my cock in rhythm with my own thrusts. We were both animals, fucking now without gentleness or care, merely uncontained lust and wild passion.

It didn't last long. How could it? Even though I had already cum twice this evening, the build up of desire, the hot tightness of her amazing ass, and the realization of one of my fantasies put me over the edge quickly, and that was probably a good thing. I gave her fair warning though, shouting out in the heat of passion that I was going to cum, and she cried back, begging me to cum up her ass.

She was crying, I could hear it in her voice, and I was instantly concerned, but she started to call out at the top of her lungs, "God, it feels so good. Fuck my ass! Oh god, fuck my ass!"

I grabbed her hips and slammed my cock home, as deep and as far as I could and held her there as my orgasm finally exploded. I had thought I had cum a lot when I blasted down her throat in the bathroom, but that as mere drops to the buckets I was spraying into her bowels. I'm sure my perceptions may have been skewed to the amazing feeling washing through me, but it felt like I was cumming for ten minutes, now stop and shooting load upon load into her hot shitter. My cock was actually a little sore from all the contractions from shooting my jiz inside her!

We sat there for a few minutes, just panting and moaning in the aftermath of our first anal sex experience. I let myself go soft inside her, the last of my cum dribbling out into her rectum before her muscles tightened and squeezed my cock out. I stared at her ass for a moment, watching the hole slowly close. It was still a little relaxed and open, but I knew that was often the case after anal sex and it didn't worry me.

I leaned in and gave her ass a little lick, which made her shudder. I would have loved to planted my lips on her puckered anus and just kiss and lick, but this was not the time. Mary had been very giving to trying this, and I felt that rimming her now, while pleasurable for her, would be more for my enjoyment not hers, and I had had my share that night. It was time for her to get hers.

I got on my back and slid under her. I grabbed hips with my hands and lowered her cunt to my lips, my tongue seeking out her clit. I was amazed by the amount of juice that was flooding her pussy - even her thighs were wet, I could feel it against my face. She came very clicking, my tongue only flicking up and down her slit a couple of times before she was screaming out in pleasure, her legs quaking around my face as she came.

She adjusted herself on top of me so she was sitting directly on my face, no longer leaning forward on her hands and knees. I continued to eat her out as she rode my mouth, grinding her hips hard against my lips as I licked and sucked. She had a fistful of my hair and was pulling me roughly into her cunt. She was calling out all kinds of strange nonsense as I devoured her gushing pussy, bringing her to orgasm after orgasm.

I have no idea how long she road me, but eventually her cries died and she just toppled to the side, her head falling right into the pillows. I crawled up behind her, giving her a kiss on the lips. She smiled weakly at me and mumbled how wonderful that was - and how she was going to sleep now.

I nodded; I was exhausted as well, a definitely ready for bed. I pulled the sheets up over us and pulled her naked body tight against mine. She was already dozing off when I settled in. I was out in an instant as well.

I could go on to tell about the next day, the next week, and even Senior Prom, but those weren't part of this story, just continuations of. This story was about the first time I had anal sex, and that part is over. Maybe, someday, I will write down those other stories as well. Maybe.

To give you, my readers, so amount of closure on this, I will say this: this was not the last time Mary and I had anal sex. She did not become an anal addict, but she did enjoy it. Anal sex for us was never really spontaneous. She always required cleanliness, which did not both me - that was the only way she could relax and enjoy it. So be it. This, however, was a good thing, because sometimes she would prepare for anal sex beforehand. She would whisper to me "I'm clean," and that was an indication of things to come later that evening. Hearing her say those words was a real turn-on and I would look forward to when we would be alone so I could take advantage of it.

We broke up during the summer before college. We were going to different schools and we both knew that, while we loved each other very much, this was not the time in our lives to be tied down to someone who could not be there for us. Turns out she was already nursing a crush on a different guy, some one she worked with. That was cool because she didn't cheat on me, but it helped her see the harsh reality. There would be people at school that we were attracted to, there were other people she wanted to kiss, and touch, and fuck - she wasn't ready for it to just be me, and honestly, I was not prepared for it to be her, either.

It was the most amicable of break ups. Whenever we were home at the same time, we hung out and reminisced, talked about current flings and past lovers. We became even better friends after the break up, really. We ended up having sex twice after the relationship was over - once was a drunken hookup over a Christmas holiday, the other was after a serious boyfriend cheated on her. She came to visit me at school and she was a wreck. She wanted it, and it did help console her and make her feel loved by someone again, even if it wasn't the person she wanted. I was glad that there was no weirdness after either of those incidents.

She told me that she hadn't had anal sex since me; a few guys had wanted to try, but they just wanted to jump right in. She said they lacked my perseverance and conviction - no one else had every spent some much time working on getting up her butt. She said she kind of missed it, the rimming and ass-fucking, but she just didn't trust any of them to be gentle and make sure she enjoyed it as much as I had. It was quite the compliment. Of course, she told me this some years ago. She's engaged now, and we don't see each other very much anymore; her fiancé might have managed to slide up her back door, I haven't asked. Not yet.

Maybe I will the next time I see her.