2 comments/ 14958 views/ 14 favorites My Sweet Clairette By: MrNiceguy777 I had just come close to having a second woman drink my piss. So close that I could - well, almost taste it. She told me she was more than willing to suck cock and drink everything I gave her. Though I wasn't really attracted to her, I found her willingness to drink piss irresistible. In fact, I was practically on fire to see her do it along with whatever else might come to mind. Unfortunately though, my desire for her rested heavily on her commitment to act as my personal urinal. Complicating things, she seemed to feel that it was also important that I should find her attractive too. Personally, if a girl told me that she found me physically hideous, but that for some reason couldn't resist sleeping with me, my reaction would be to revel in my magnetism...and to sleep with her. I guess we all have our standards. It's just too bad this sticking point came up in conversation before we met to consummate things. Once it became clear that her and I wouldn't be getting together, I was back trolling the dating line for girls. Only now I had a new sense of what was possible and with that sense came the additional goal of finding a girl to drink my piss. I don't recall exactly how long it took for the subject of pissing to be successfully worked into a conversation, but I remember that it took less time than I would have expected. Really I don't think it took longer than two or three weeks before I found a girl who responded with surprising enthusiasm. The first girl from the line that I spoke to about piss was Claire. She was twenty-six, 5' 5", 130 lbs. with medium length brown hair, green eyes and was doing a masters in political science. Claire had a really relaxed attitude about meeting people as well as what she was looking for on the line. In terms of her features and her proclivities, Claire seemed a bit like a female version of me. I was thirty-two, 6', 190 lbs. with brown hair, green eyes, and like her I had some fairly pornographic ideas about sex. I really felt like I wanted to meet her, so I was a little hesitant about bringing up piss games for fear of scaring her off. The conversations were just so open though, that it eventually it came up when we discussed some of the things that we had tried. I told Claire about Han, the ex-girlfriend who made a deal to drink my piss if I let her stay the night after I caught her cheating. Claire said that she could see what was in it for me, but she thought that my ex had no dignity. I told her at the time I kind of felt that way too, but the thought just made it more exhilarating. Claire also told me that in her opinion I had let my ex off too easy and that she still would have kicked her out afterwards anyway. I really should have taken note of that attitude. That led me to also telling Claire about the last woman I met from the line and how she was into sucking my cock and trying to drink my piss. Even though it no longer seemed likely happen, I still told Claire that we were trying to get together. I also told Claire that I wasn't sure I was really attracted enough to the woman to go ahead with it. In truth of course I was well past my initial reservations, but I wanted to appear at least moderately discriminating about where I was willing to put my dick. The temptation to show oneself in the best possible light is often just too difficult to resist. That wasn't what I should have worried about with Claire though, because her response was, "What are you waiting for? A mouth is a mouth." A presumably common enough attitude in prison showers, but not even from the sluttiest girls that I've known have I heard such an emotionless deconstruction of oral pleasure. Better yet Claire was intrigued by the idea of drinking piss and wanted to give it a try. As her only conditions she wanted to try it in the shower and wanted to be able to stop if she didn't like it. She also wanted to meet at a bar near her place in case things didn't work out. Like I mentioned before, Claire seemed like female version of me. I didn't like making the travel effort for a blind date either. In this case though I was willing to make an exception. Putting the plan into action turned out to take a little time. First I was out of town for a week with work and next Claire was tied up for a few weeks on her thesis. In the meantime I was still calling the dating line and keeping myself entertained. Finally though we were able to pick a good night to meet. It was a Friday night, so if things worked out I wouldn't have to worry about work the next day. We had each other's descriptions and to help spot each other we added some detail about what we would be wearing. Claire picked a pub near her place and a little more than a month after we first spoke I was heading out to meet her. Claire lived near the Annex, south of Bloor St, so it was a simple subway ride from my place over to her neighborhood. The Annex is right near the University of Toronto and it's a pretty active part of town with a vibrant mix of bars and restaurants. I walked into the pub where we were to meet and since it wasn't crowded yet, I presumed Claire would be easy enough to spot. As I walked past the bar I noticed a nice looking girl with brown hair a bit past her shoulders. She was sitting at a small table on her own and looked up from the book she was reading as I passed. For a moment I hoped that she was Claire, until I realized her clothes didn't match our arrangements. Too bad I thought as I continued to the back of the pub, which I found deserted. Claire was supposed to be at the pub ahead of me, so I was hoping that she was just late and not going to be a no-show. Returning back to the bar to order a beer I noticed that girl was still looking towards me. As I waited for the bartender she got up from her table, walked over to me and asked if I was meeting someone? It turned out that this was indeed Clair, misleadingly dressed, but exceeding expectations. Claire's deceptive attire got us right into a conversation without any awkward feeling out period. Claire first claimed that the clothes she planned to wear were in the wash, but soon came clean and admitted that the wardrobe was insurance in case I had lied about my description. I smiled and told her that I was relieved to have met her minimum standards. Claire squeezed my arm and said, "It's not like that, but I'm really happy how things turned out." Claire had softer features than I had imagined. She seemed so decisive and assured on the phone that I had imagined she would have a bit of a harder edge to her looks. Her hair was natural and not overly styled, in fact that characterization in general would appropriately describe her looks. She looked like an outdoorsy girl next door. Claire wore very little make up and her clothes had a hint of the urban grunge look so common to the campus. Claire's clothes were loose fitting, but her voluptuous proportions were undisguised and she clearly could have looked good in anything. She had pale skin, and soft looking pink lips, her nose was lightly freckled and she had green eyes that could best be described as feline. I usually find that green eyes need closer study be fully appreciated, but Claire's eyes had an immediate appeal. We really clicked with each other from the start. We sat and talked about so many things and as the night went on we both managed to get fairly drunk. I couldn't help but think that under normal circumstance with a date going this well I would typically have been starting to think about setting up with another date or even spending the night together. I shared my thoughts with Claire, then leaned in close and whispered to her, "Looking at you now I can't believe that I already know that I'll soon be pissing in your mouth." Claire smiled almost inwardly as if savoring the image and pulled my hand down and pressed it against her pussy. She told me she could hardly get anything done over the last few days thinking about tonight. "Do you want to get going?" I asked. "Hell yeah, let's go!" she said. It was mid-December and there'd recently been a fairly decent snowfall. Despite the snow, it wasn't overly cold for the time of year. It was a good night for a walk and Claire's place that was a few blocks south of Bloor. On the walk to Claire's we abandoned all efforts to keep our hands to ourselves. Whether playfully freezing each other with our cold hands or more serious and time consuming explorations, we were really getting to know one another. As a result, what normally would have been a fifteen minute walk was shaping up to take much, much longer. Walking south on Euclid Ave, we passed a park on the west side that seemed a good spot to take a few moments to intensify our groping. We moved off the street to a darkened walkway that ran between two fenced off tennis courts. From there slow lust filled kisses progressed to the point that I had Claire's jacket open her shirt bunched up over her creamy tits. As soon as I had her breast in my hands I knew I loved them. I don't know if it's the result of my tastes or circumstances, but the majority of women that I've had extended relationships with have been either petite or had athletic bodies. While none of these girls had especially large breasts, regardless of their size, they all had nice form that worked great with their bodies. Aside from that though, when I have been with an attractive and amply endowed women it's almost like another world. Well maybe not another world, that might be too much, it's more like getting an unexpected customer upgrade. It's like getting the window seat at a restaurant with a nice view. It doesn't change the quality of the meal, but it does enhance the experience. I was feasting on Claire's breasts and had her jeans undone too. Claire's pants were midway down her hips, just far enough so that could play with her wet pussy. With Claire moaning I offered her my fingers to give her a taste of her juices. "Does it taste good?" I whisper to her. "Yes, it does," was her hushed reply. I turned Claire around and pulled her jeans down farther to give my mouth full access to her asshole and pussy. Claire's pussy was frothing with juice, and just as she claimed, she tasted really good. Claire was a complete horny mess as I licked her pussy and ass, spreading her ass cheeks to get my tongue as deep up her puckered hole as possible. Claire had previously told me that she wasn't into anal and while girls usually know by the age of 26 where they stand on the subject, my tongue has a past record of convincing girls to try. In fact my tongue has earned me a few anal requests. I did want to get to Claire's place though, I really wanted to take a piss and I especially wanted to see Claire drink it. I stood up behind Claire, reaching around I grabbing her pussy from behind and with her pressed against the fence I filled her with single thrust. Once my cock was coated with her juice I pulled out said, "How 'bout you take a taste of yourself and then let's hurry to your place." Claire turned quickly and got on her knees. She ran her tongue up and down my shaft before taking me in. After she sucked my cock for a minute or two I pulled out and said, "OK, let's go." "Alright," she weakly agreed, but obviously she was ready to be fucked right there on the spot. Though she had agreed to go, Claire was still all over me as we resumed our walk. It probably took us about ten minutes just to cover the hundred or so feet to the other side of the tennis court. At the other end of the court there was a small parking lot with a big snow pile at the back of it. I couldn't hold it any longer and I told Claire that I really needed to piss. I asked if she was ready for a drink, but Claire declined and said that I had to fuck her first. "OK," I said, "I'm sure there'll be more for you later." I took out my cock and while making out with her I pissed in the snow bank. When I finished Claire demanded, "I want you to fuck me right now!" Claire was already sliding her jeans down and I grabbed a handful of snow and ground it into her snatch. While holding the wad of snow on Claire's pussy I pulled her ass back toward me and slide my cock through the snow into her hot cunt. We started fucking standing up, but without the fence to brace against I eventually pushed Claire down into the snow. I had Claire face down and ass up in the snow bank and no matter how hard we fucked, her ass was pushing back to welcome my thrusts. All the while my snow filled hands were grouping her pussy and pinching her thick nipples while we feverishly fucked. We were right beside where I pissed too and even though my beer infused urine was only slightly yellow the snow was still notably discolored. I reached over and grabbed a small handful of piss saturated snow and said to her, "Now that I'm fucking you I want you to have the taste of my piss." Responding, Claire opened her mouth and I fed her some infused snow. I couldn't help but fuck her harder. "Do you like it?" I asked. "Yes! Yes I do," Claire breathlessly replied. "Do you want more?" I asked. "Yes, please," she said and I fed her a little more of my gelato. As I fucked her I positioned her a bit little closer to my piss and told to help herself. She responded by burying her face right in the middle of the piss perforated snow. I just had to push Claire's face deeper into the snow as well as I driving my cock deep into her pussy. Buried to the hilt inside Claire I just couldn't hold back. Unable to stop myself I let loose what felt like torrents of sperm splashing into Claire. As we lay there in the snow recovering Claire turned her face back to me and we kissed. I could tell by the way her tongue deeply explored my mouth that she wanted to share the taste of my piss. We got up and gathered ourselves together for the remainder of the walk. I asked how she liked her first experience with piss and she said that she felt so dirty doing it and that she didn't want it going to my head, but that was one of the best fucks she ever had. Of course it did go straight to my head, news like that always does. Claire said the piss wasn't bad at all and that she couldn't wait for more. She thought having it mixed with snow made it easier. I thought to myself that it was like watering down whiskey. Of course I'm a bit of a purist and now that I'd given Claire a taste I couldn't wait to fill her mouth with my single malt, straight up and neat. The way her mouth had engulfed my cock earlier really made me want to see it filled to the brim with my piss. Afterwards I'd fuck her long and hard with her tummy feeling all warm and full. I'd fuck her as long and hard as I could, all the while she'd have the taste of my urine coating her mouth and its scent on her breath. After our fuck in the snow we made better time. We arrived back at her apartment and had the place completely to ourselves. Claire did have a roommate, but fortunately she was already finished her semester and had gone home for the holidays. Claire had a ground floor apartment and her room was at the back in an extension that jetted into the backyard from the kitchen. The room was pretty big with lots of windows and had its own en suite too. It was real luxury living for a student. Claire opened a bottle of red wine, we stripped down out of our snow covered clothes and she snuggled up to me on the couch in her room. I told her she was not only the most interesting person that I met off of this line, but without doubt the best looking too. Despite what Claire said about a mouth being a mouth, it's not really true, especially if someone has a visual bent like me. I wondered if Claire would be charmed if I told her how much more I thought I would appreciate pissing in her mouth than anyone else I could think of. Admittedly it's not the sort of line that every girl would be receptive to, but when you're looking into the lust fill eyes of a naked girl who's stoking your cock, different rules seem to apply. When people are horny as hell a lot of things that might not seem that savory under normal circumstance, suddenly begin to make a lot of sense. Claire slung her left leg over my leg and I could feel the cum filled wetness of her pussy on the top of my thigh. She was still clutching my rigid cock and pressing it against her stomach. While Claire was grinding her pussy on my leg I was humping against her stomach with the head of my cock prodding and dampening her tits with pre-cum. With my finger I swiped an oozing drop of pre-cum from the eye of my cock and offered it to Claire to taste. I let Claire demonstrate some of her intentions on my finger, before removing my dampened digit and lowering it down to the entrance of her asshole. I massaged Claire's asshole open, slowly circling her rim until I could feel her welcome reception of my fingers. Leading by example I brought my finger from her asshole to my mouth for re-moistening, then returning my finger and pressing it deeper inside. We continuing to grind against each other, but with greater urgency. The next time I removed my finger from Claire ass I offered it to her to suck. She accepted and her mouth worked my fingers like she would a delicious cock. I could feel her tongue circling my digits as she worked them in and out of her mouth. "Are you ready to suck my pissing cock?" I asked. "Yes, I am," she said. "Do you want to do it here or in the shower?" I asked. "You decide Mike," she said. "Here's perfect," I replied. "I want to see you work without a net and drink my piss right here on your couch without wasting a drop." With a bit of a shy smile Claire said, "OK, I want to see if I can do it too." Then patting the couch she asked, 'Where do you want me?" Claire had a futon couch and like most futons the mattress was sliding down the back of the couch. It was about time for the drooping mattress to be positioned back up on its frame, but for the moment it was positioned perfectly for what I had in mind. I had Claire sit up on the couch with her head tilted back just over the top edge of the mattress. I stood in front of her on the couch with a foot on each side of Claire. My right knee braced against the back of the couch and my cock poised in front of her face. Claire took my cock in her mouth and started working on it. At first I enjoyed letting her go to town and I helped by guiding the back of her head for greater penetration. Under normal circumstance this would have been the start of a great blow job, but pissing needs different sorts of encouragement. I told Claire that my cock just needed to relax to piss and that she should just let me hold my cock still in her mouth until I could go. With her free hand rubbing and fingering her pussy, Claire lightly squeezed my balls with the other hand while my cock soaked in her warm mouth. I'm not exactly sure how long it took for me to start to piss, but it seemed like quite a while. Despite all the beer we drank, I guess I wasn't quite queued up for another piss so soon after our earlier stop at the park. I didn't mind though, Claire had a great mouth for happily accommodating a cock. Despite the sense of anticipation there's nothing that I couldn't enjoy about my cock resting in Claire's mouth. I think for girls it can be tough though not to try to produce results when there's a cock in their mouth. Every so often Claire would start working on my cock again and I would just have to remind her to relax. Even with the inside knowledge, so to speak, the prospect of my pee's arrival was weighing on me too. I think the anticipation of how my piss would be received when it flowed for the first time into Claire's mouth was something that was incredibly thrilling. Would it be too much for her to deal with or would she readily drink it down? Would she hate it and try to muddle through or would she love being so filthy? Since Claire was only the second girl to try drinking my piss, I really hadn't sorted everything out yet about what I liked so much about doing it. I knew though that I was beyond turned on to have such an attractive girl willing to drink my piss. My Sweet Clairette I wish I could have known how the wait for what was to come affected Claire too. Did it make her nervous? Was she impatient? Did the wait build excitement? I'd love to be able to have known. In the meantime to sooth us both I stroked my fingers through her hair until the first trickle of piss finally ran into Claire's waiting mouth. The initial flow into her mouth would have been little more than a dribble. The start of my piss would have been thick as it flushed out and combined with the laggard sperm remaining from our fuck in the park. With Claire's head tilted slightly back and the head of cock fully engulfed, I filled her mouth for the first time with a lush mix of sperm infused piss. I could feel Claire's tongue roaming over the head of my cock and probing its eye, as if trying to staunch the flow into her mouth. Claire's eyes were closed in a look of serene repose, seeming every bit like someone intent on enjoying every new sensation and unfamiliar taste. She really did look sexy as hell, naked on the couch with my cock in her mouth and when her eyes opened and met mine it was electric. Her eyes on their own conveyed a certain sexual mystique, but looking into them and knowing that without objection my cock was filling her mouth with piss was exalting. It took some time to get going, but once the piss started to flow it was a pretty long and incredibly satisfying. Maybe not just for me either, because Claire barely spilled a drop and really seemed to be savoring what she was doing. I tried to pace my piss so that Claire wouldn't be overwhelmed. It's not always the easiest thing to do, especially with how hard my cock was in her mouth. I let Claire manage my cock while I just tried to concentrate on my flow. She grasped my shaft in her hand, keeping me directed into her mouth. Claire controlled the depth of my cock in her mouth and mostly nursed from the end of my pissing dick. At the beginning Claire took the approach of a normal blow job. The few spills she made were when she failed to master my discharge at the back of her mouth. It wasn't so much that Claire would choke, she was pretty damn good with a cock in that respect. It was more the case that with a full cock in her mouth that she couldn't manage a perfect seal. Escaping piss would run from her mouth, dribble from her chin and drip down onto her beautiful breasts. There never seemed to be so much piss lost that it reached the couch, but Claire's neck, shoulders and tits were dappled with droplets of piss that seemed to conveniently adhere to her body. She looked like a sultry cock loving slut that just stepped out from the sauna, only it wasn't sweat. I loved it all. I loved her sucking my pissing cock and I loved tilting her head back, seeing and hearing my pee splash into her open mouth. I especially adored when she would look me in the eyes as she swallowed mouthfuls of my piss. Her eyes would flutter and close as she drank my fluids and then brightly reopen with a dreamy vacancy. When I finished I grabbed her head and drove my cock deep into her accommodating mouth. After a few deep thrusts I withdrew to rub and hump Claire's lovely face with my wet cock. Relaxing afterwards, I extended my arms in a stretch and uttering an containable, "Wow!" Countering with a satisfied smile Claire purred her agreement, "Wow." Since Claire's roommate was a non-smoker, lighting up was normally verboten in the apartment. However, in light of her roommate's extended absence and our recent disregard for normal etiquette regarding the treatment of human waste, Claire decided breaching house smoking rule wouldn't be such a big deal. Sitting back on the couch together I lit up one of my smokes for us to share. I had my right arm around Claire while we smoked and she cuddled up against me. The feel of her soft damp breasts against my skin and the taste and heat of Claire mouth when we kissed augured well for perversely wonderful night together. I wasn't planning on using the actual bathroom that much that night, but I did notice that the en suite attached to Claire's room had a double tub, so I suggested we try taking a bath together. "Sounds like that could be fun," Claire replied. Claire stood up and I reached out my arm so that she could pull me up. After feigning a bit of annoyance Claire grabbed my arm and tried to pull me. "Jesus you're heavy," she complained as she leaned back to use her body as a counter weight. The technique worked and once I was upright I had to hold tight and pull Claire back up to vertical too. Claire dropped the cigarette in the toilet and handing me her lighter asked that I light the candles around the tub while she peed. I took the lighter from her while my free hand found her wet pussy and I asked Claire, "Would you rather try pissing in my mouth?" "Are you sure?" she asked. "I think so," I truthfully explained. "You just turn me on so much that I can't help but want to try too." I'd come to see drinking piss as a particularly complete act of submission. To drink human waste from another person for their pleasure just seems so erotically debasing. While my piss flows into a girl's mouth, by drinking it she's completing the power transmission back to me. The power flows back upstream against the current, coursing through my cock and filling my body. It feels incredible, it's not an orgasm, but it's so incomparably pleasing and I wanted Claire to know first hand that feeling too. I was also just so turned on with what Claire had done, that I was thirsty for her piss too and I wanted to know how it would feel to be her pee drinking slut this time. I got into the tub and lay on my back. My feet were up on the side of the tub, so that I had enough room to lay flat on my back. Claire stepped in and straddled my face and lowered her pussy onto my mouth. I've got to admit when a girl has me turned on I've never had any reservations about sucking a girl's pussy after fucking them. I've eaten my own cum out of a girl on plenty of occasions. In this case though, I never really got much of a chance to note the cum leaking from Claire's pussy, because she started pissing as soon as her pussy touched my mouth. With my nose just peeking out from her lightly trimmed mound, I could look up over Claire's modest belly and voluptuous tits and see her intently staring down at me. Claire filled my open mouth with piss and kept splashing my face when I'd closed my mouth to swallow. With my arms I lifted Claire off my face just enough, so that I could see the piss spray from her. I position her, so that the stream mostly found its way to my mouth, but it was a pretty wild spray. Her piss was intently warm with a scent and taste that was lighter than I expected. I wanted to do a good job and I drank her piss without reservation. The biggest challenge was there was no interruption to her stream. Trying to drink as much of her piss as I could, I eventually opted to hold Claire close and suck on her pussy lips to better control the jets filling my mouth. Finally with Claire's piss reduced to a trickle, I changed my approach from one that focused on managing the flow as best I could to ordinary pussy licking. Instead of sucking on her fleshy cunt to make sure I drank as much pee as possible, my tongue explored her piss dampened pussy. There were a few things that really stood out to me when Claire pissed in my mouth. The taste wasn't bad or overpowering, but near the end there was just so much piss to drink that it started to feel overwhelming. I felt bloated with piss. It was like being in a beer chugging contest. I'd never really factored that in for my recipients. Since Claire's first drink followed on the heels of a recent piss, she got off relatively easy by comparison to the full bladder that she released for me. It made me think back to when Han drank my piss. I had a new understanding of how difficult it must have been for her to force down a full night's piss. She was so tiny and I gave her so much piss to drink. Considering the coercion that went into getting Han to do it, it really must have been a task for her to manage swallowing every last drop. The insight didn't awaken any new feelings of empathy for Han, but the better understanding of the effort that I'd just been given did add another element for me to savor as part of my memory. Aside from that, the feeling that I had drinking Claire's piss was one of pure and filthy surrender. I know Han felt resentment, but I wonder if she felt anything else. I wonder that if on any level she enjoyed being made to drink my piss. I suppose I'll likely never know. Meanwhile I was still licking Claire's wet pussy with the back of my head in a puddle of her piss. Then when I couldn't wait any longer, I pushed Claire off my face and slid her down towards my cock. I slipped effortlessly into her wet pussy and once inside her Claire lowered her face to mine. In full embrace her tongue returned the appreciation by tasting the residue of piss she left on my skin and in my mouth. We had a slow grinding fuck lying in the tub until finally I suggested, "Let's take a bath." We let the water run and rinsed the tub. Despite drinking each other's piss somehow bathing in it still didn't have appeal. Once the piss was gone Claire closed the stopper and I fucked her from behind against the tiled wall and played with her breasts while the tub filled around our feet. Claire's tits were just so substantial, they were real treats to grab while we fucked. Claire's tits had real personality and I was memorized by the way they swayed and their fleshy jiggle. Once the tub was full we slid down into the hot water and relaxed. We spooned with my cock deep in her pussy and we were buoyed together in the large tub. We continued to lightly fuck and I told her that I wanted to shave her pussy which was a favorite grooming service of mine. Claire was a little reluctant, not the least because her occasional use of her roommate's shavers was apparently a point of friction between the two of them. Just like for anything else that night though, Claire was game and any reticence quickly forgotten. For now we'd deal with shaving Claire's pussy silky smooth and later, if needed, Claire could smooth things with her roommate. I soaped up Claire's pussy and slowly started shaving her mound. Claire studied my progress with particular attentiveness as I shaved up close to her labia and clitoris. For some reason most women seem to get a little nervous when I shave around their clit. I don't know why, praise Allah, I've never made a slip. Then as a standard part of my aftercare I treated Claire's naked pussy to soothing licks from my tongue. Once the water cooled we got out of the tub, dried each other off and reconvened to Claire's bed. Despite Claire's claim that she was steadfastly opposed to anal, I figured that if she was ever going to waver tonight would be the night. I love to deflower girls' assholes and convincing the reluctant is always special. Besides, between having filled Claire's cunt with a load earlier in the night, along with being a bit drunk, my cock was feeling a little desensitized. I was thinking if I were going to pump another load of cum into Claire, that I might need the added debauched tightness of her virgin ass. After all, when you've just been fucked in a snow bank at the side of the road, drank from a pissing cock and had an orgasm while a guy you just met licked your pussy and drank your piss, does it really still make sense to refuse anal sex? I didn't exactly pose it like that to Claire, but I did let my tongue do the talking. I got on top of Claire and we kissed deeply while my stiff cock slid back and forth over the lips her pussy. I didn't enter her, instead I just let Claire feel my cock against her wetness. Then I began working my my way down to Claire's body. I stopping at her tits and I feasted on her sumptuous breasts before running my tongue down to Claire's now hairless pussy. Her cunt was so juicy that I could have licked it forever. Instead though I rolled her over and plunged my cock into her sopping pussy as Claire gasped. Then I began licking Claire's neck with my cock in her pussy. I started slowly licking down Claire's spine and as my tongue worked its way down my glistening cock slid from her pussy. Claire let out a plaintive moan that was tempered and mollified by the promise of my tongue's progress. As my tongue started its accent up from the small of her back, Claire's ass began to rise in welcoming anticipation. My tongue pushed through the cushy cleavage of Claire's butt cheeks and plunge into her tasty asshole. Claire moaned again, but this time without a hint of complaint. I probably spent about fifteen to twenty minutes doing everything I could with my tongue to open Claire's asshole. Claire ever so helpfully reached back to hold her ass cheeks apart to maximize my oral access. I circled her rim endlessly and pushed my tongue as deep up her ass as I could go. All the while playing with Claire's clit, I'd press the heel of my hand against her button and Claire would push back her ass and clit against me. Eventually my tongue ran an inch or so down to a wetter nexus. I don't know if I've ever licked a hotter or juicier pussy. Claire's pussy was so damp that after a few minutes I could barely taste the residue of piss in my mouth anymore. The next step was to thoroughly wet a couple of my fingers in Claire's pussy and test the receptiveness of her ass. In no time at all Claire's asshole was accepting with silky ease, first one and then two fingers. In and out they went as deep as can be. I got on my knees behind Claire and pushed my cock into her pussy. With my fingers up Claire's ass I could feel every thrust of my cock in her pussy. Claire was completely responsive to having both holes filled, but I needed to manage the transition of my cock from her pussy to her ass. No matter how willing and responsive a girl may appear, a lot can go wrong with anal sex if entry isn't smooth. Before my ex Han introduced me to KY, I had always relied on pussy juice for lube and it just didn't reliably do the job. It's still fun to fuck a real ass slut without lube, but for first timers KY is key. With lube even the most reluctant of little sodomites seem to at a minimum be able to endure having their back doors knocked in. So despite Claire's previous declarations, I'd still brought a tiny tube of lube just in case I was able to change her mind. The KY was in the pocket of my jeans beside the bed, so I just reached down with my free hand and pulled out the tube. I liberally covered the fingers that had already been working Claire's ass and then re-entered them in her butt to coating her rectum with cool gel. Next I withdrew my cock from Claire's pussy and covered my dick head with KY. I positioned the lubed head of my cock at Claire's asshole and began working it in circles over her dilating sphincter. Then leaning close to Claire I whispered in her ear, "Are you ready?" "Yes," she replied "but please go slow." If you're about to fuck a girl in the ass for the first time and you think you'd like to do it again I'd recommend taking it slow too. So as Claire requested I slowly pushed the head of my cock into her virgin asshole. With uncharacteristic patience and caution I worked my cock deeper and deeper into Claire's ass. Claire had flattened out onto her stomach and I could feel the tension in her as she accepted my cock. Her body was under mine with my head behind her shoulder and with my face pressed against her I could smell the fragrance of her hair and the hint off piss on her breath. Under the circumstances the scent and the feeling of her asshole's spasmodic contractions around my cock were an obscenely seductive combination. Slowly pushing the pace of Claire's receptiveness I worked my cock deep into her ass. Claire was doing pretty good taking my cock and her hips were cresting up to receive my languid thrusts. The final inch of my cock seemed to breach her capacity though, as my deepest thrusts would cause her to hiss with pain and try to retract from my cock. Of course she couldn't retract completely, sandwiched between me and the bed there was no escaping without my withdrawal. Not that she wanted to escape, at least not completely. By now Claire certainly wanted her ass fucked and filled with cum, she just wasn't quite ready for a complete anal assault. Moderating my thrusts I tried to calibrate them to her maximum receptive depth. It's not an exact science, so now and again I would pierce through Claire's comfort zone. I did it often enough for the head of my cock to enjoy testing the unyielding capacity of her rectum, but not so much that Claire ever pleaded for restraint. When a girl is so boarder line on anal like Claire, I try to be cautious and not take more than I can get. Nonetheless, I didn't get girl's to drink my piss without some willingness to push the envelope. What I wanted to do was get Claire on her back with her legs over my shoulders, so I could see and feel her wet pussy against me every time I drove my cock into her ass. Considering what we'd already done it shouldn't be much of a barrier, but I was still weary about giving Claire any opportunities to reconsider. "I want to roll you over so I can see your face while I fuck you," I whispered. "Let me try to keep my cock in you while I turn you over." I rolled Claire on her side keeping my cock fully buried in her ass. But when I lifted Claire's leg over my shoulder my stiff cock wasn't far enough in and it sprang free. I shouldn't have worried about Claire having second thoughts though, because once I put both her legs over my shoulders she reached down grabbed my cock and guided it into her open asshole. Claire had a fairly high bed that was an ideal height for me to position a girl up against the side and fuck while standing up. I swung Claire around to the side of the bed, so that I could stand on the floor. I them moved Claire's butt to the edge of the bed and placed her legs up over my shoulders. In this position I was able to look down and see the fleshy pink lips of Claire's pussy, all open and glistening with juice and also had an unobstructed view of Claire's previously virgin ass stretched around my cock. I've always liked the impropriety of so clearly seeing my cock working in and out the wrong hole with the proper hole so close by, glistening, but unused. I like to lean forward while I drive my cock deep into a girl's ass and feel her wet pussy on my stomach. When I would do this to Claire her eyes that were closed in a sensual reverie would pop open with vivid intensity. The pleasurable pressure of my pelvis on her pussy (say that five times fast), no doubt helping to re-associate the twinge of pain that Claire would feel when my cock plunged to its deepest depths of her ass. With Claire's gleaming green eyes and open mouth so closely facing me as I folded her over to bury my cock in her ass, I let a big wad of spite dangle and drop from my lips into her waiting mouth for her to ruminate on. Claire's pussy was so wet that every time I drew back from her, stings of cum from her pussy to my stomach would stretch and collapse. It was a curious display of the tensile strength of Claire's vaginal fluids that begged for continuing repetition. It was a great ass fuck and for a first timer Claire's ass was given an extended ride. It took a lot of work for me to deliver a second load, but once I started getting close I didn't want it to end. I rolled Claire back on her stomach, so that I could feel her sumptuous body against mine when I came. With my hands reaching around Claire's body grasping her pussy and helping raise her hips, we increasingly worked together towards our orgasms. My Sweet Clairette Finally reaching the point of no return with my cock deep in Claire's ass, I felt the release begin and then nothing...I actually passed out with my orgasm. Through a fog I heard Claire with panic in her voice "Mike, Mike get off, I think I'm bleeding." Coming to though I stared to fuck Claire's ass again, but Claire said with some fright "Don't, I think feel blood in my ass. Am I bleeding?" Still humping I started to realize that my cock was unexpectedly softening and I begin to put things together. I'd never passed out when I came before, but I was starting to remember a powerful orgasm. "Um, that's not blood your feeling in your ass, it's my cum." I told Claire. I told her that I think my orgasm was just so draining that I passed out. I could feel Claire's body again relaxing under me. "I wasn't expecting how cum would feel in my ass." Claire said. "What a relief, it actually feels kind of cool now that I know I'm not damaged. I think I was really starting to freak out." Claire and I both lay back on the bed, had another smoke and we talked about our night. I had apparently made an anal convert out of Claire and we were both looking forward to the new piss games that we could play the next time we got together. We fell asleep holding each other. In the morning I woke up with Claire sucking my cock and we fucked one more time. When I was almost ready to cum I pulled out and came in Claire's mouth. After about another half hour relaxing we got out of bed, washed up and went back up to Bloor for brunch. Everything was going so well, my eggs benedict was served with a delicious dill sauce and we talked about our plans for the holidays. I felt we might be starting something, so I wanted to let her know my complete situation. I told her I didn't really consider it serious anymore, but that Han and I still had a long distance relationship. Claire asked me if Han knew I saw other people and I told her that technically she didn't. Then as I tried to explain the technicalities, Claire abruptly stood up and with previously unheard disgust in her voice said, "If there's one thing I can't stand it's someone who can't be trusted!" Claire grabbed her coat and hastily charged out the door. Stunned and embarrassed, I picked at my food as I waited for the waitress. After paying I walked back to Claire's to try to explain, but she either wasn't home or wasn't answering the door. The truth was that Han and I were all but through and neither of us could have had any expectations about the other's fidelity. We'd always been a dysfunctional couple and even though our occasional weekends with each other were filled with the promise of great fucking, we could never get together without fighting. I went home wishing that I could phone Claire, but I didn't have her number. Often when I met a women from the dating line I would give them my number up front, but I'd only get their's after meeting. If the date went well and I managed to demonstrate an acceptable level of mental stability, while generating a soupçon of attraction, I'd usually get the number. Sleeping together usually meant I was on track. Under this arrangement getting the number was kind of an end of date thing and I got most of the way there, but tripped just ahead of the finish line. I tried calling the dating line night after night for the next week or so, but I never heard Claire's voice. Before I headed back to Montreal for Christmas I wrote Claire a letter. The letter was part explanation, including news that I'd completely broken things off with Han, and part what I hoped was an enticing erotic recap of our night together. I went to Claire's place and again with no answer at the door I put her name on the envelope and left it in the mailbox. Later returning from the holidays I was hoping there would be a message from Claire. When I got inside I was excited to see that the answering machine message light was on. The first message was a friend's now out of date New Year's Eve party invitation, the next two were hang ups and then finally it was Claire. Only it wasn't Claire, it was Claire's voice, but based on the heated expatiation left me, apparently the girl I met liked to use her roommate's name when she called the dating line. The girl I met was quite livid about the letter I left for her, since her roommate 'Claire' had read it. Aside from bringing the real Claire into the loop on smoking in the apartment and her shaver use, there were apparently a number of other activities we had enjoyed that the girl I met had wanted to keep private. Based on the tenor of the message, insults aside, it didn't seem that she and I would be getting together again anytime soon.