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. For my part though, I wasn't really attracted to her, but found her willingness to drink my piss irresistible. In fact, I was practically on fire to see her do it along with whatever else might come to mind, but unfortunately my desire for her rested heavily on her commitment to act as my own personal urinal. Complicating things, she seemed to feel that it was also important that I should find her attractive. Personally, even if a girl went so far as to tell me that she found me physically hideous, but that for some reason couldn’t resist wanting to sleep with me, my reaction would be to revel in my magnetism—and to sleep with her. I guess we all have our own standards. It's just too bad this sticking point came up in conversation before we met to consummate things.

Once it became clear that she and I wouldn't be getting together, I was back trolling the dating line for girls. Only now I had 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 any longer than two or three weeks before I found a girl who received the subject with interest.

The first girl from the line that I spoke to about piss was Claire. Claire was twenty-six, 5' 5", 130 lbs. with medium length brown hair, green eyes and was doing her masters in political science.

Claire had a really relaxed attitude about meeting people as well as what she was looking for. 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 have 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 drinking. The conversations were just so open though that it eventually it came up.

First I told Claire about Han, the ex-girlfriend who made a deal to drink my piss if I let her stay the night after she was caught cheating. Claire said that she could see what was in it for me, but she thought 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.

Then I told 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 told Claire that I wasn't sure I was really attracted enough to the woman to go ahead with it though.

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 can be just too difficult to resist.

That wasn't what I should have worried about with her though, because Claire's 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, she was intrigued by the idea of drinking piss. As her only conditions, Claire wanted to try drinking my piss 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.

Putting the plan into action though was proving slow developing. 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 line and keeping myself entertained.

Finally 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 headed 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 great variety of bars and restaurants. Interesting stores too, especially if you count tastefully appointed Honest Ed’s – look it up.

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 car 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 this was Claire, until I realized her clothes didn't match our arrangements. Too bad, I thought. I continued to the back of the pub and found it deserted.

She was supposed to be at the pub ahead of me, so I was hoping that she was just late and wouldn't 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? Misleadingly dressed, but exceeding expectations, this was Clair.

Claire's deceptive attire got us right into a conversation without any awkward feeling out period. Claire first explained that the clothes she planned to wear were in the wash, but then 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.”

I told her I'd done the same thing myself, though I'd never completely altered what I agreed to wear. I had only changed an article here and there for deniability in case of a real meeting disaster.

Claire had softer features than I had imagined. She seemed so decisive and assured on the phone that I unconsciously expected a bit more of a harder edge to her looks. Her hair was natural and not overly styled, in fact that could describe her looks in general. She looked like an outdoorsy girl next door. Claire wore very little make up and her clothes had a hint of the urban grunge edge 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 as the night went on, all the while the both of us getting fairly drunk. I couldn't help but think that under normal circumstance, with a date going this good, I would typically be starting to think about the possibility of a night together. A few shared touches and kisses would potentially confirm an unspoken plan to sleep with one another. How wild our time in bed together would be would have to be sorted out as we go.

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.

While we finished our beers and waited to settle our bill we could hardly keep our hands off each other. We whispered shocking sweet nothings to one another that to a causal listener could possibly have been confused as nasty threats.

Finally we headed out from the pub. 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, which was good since Claire's place was a few blocks south of Bloor.

On the walk back 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.

I don't want to generalize, but based on a very limited sampling group I find that if you put a few beers into a yummy post graduate student, that they take forever to walk home.

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 on a darkened walkway that ran between two fenced off tennis courts. From there slow lust filled kisses progress to the point that I had Claire's jacket open her shirt bunched up over her lovely 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 athletic with rather tight 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 wet fingers from her pussy.

“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 asshole as possible. Claire had previously told me that she wasn't into anal and while girls usually know by the age of twenty-six where they stand on the subject, my tongue has a past record of convincing girls to try. In fact my tongue has earned anal requests for my cock.

I did want to get to Claire's place though; I really wanted to piss and I wanted to see Claire drink it. I stood up behind Claire and grabbing her pussy from behind and pressing her against the fence I told her that I was going to fill her with my cock. Once my cock was covered with her juice I pulled out and told her, "Take a taste yourself on my cock and then let’s go to your place."

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 on, Claire was all over me as we continued to walk. It probably took about ten minutes just to cover the hundred plus feet to the other side of the tennis court.

At the other end of the tennis court there was a little parking lot with a big snow pile at the back of it. There I told her that I just couldn't hold it any longer and 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 pussy. While holding the wad of snow on Claire's snatch I pulled her ass back toward me and slide my cock through the snow into her hot pussy. I started fucking her slowly while standing and eventually pushed her 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 fucked.

We were right beside where I pissed 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 in your mouth." Responding, Claire opened her mouth and I fed her. 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 had to push Claire's face and muffled moans deeper into the snow as I drove my cock deep into her pussy and let loose what felt like a torrent of cum.

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. It always does.

Claire said the piss wasn't bad at all and that she couldn't wait for more. She thought having it 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. After I'd fuck her long and hard with her tummy feeling warm and full with piss and the taste of my urine coating her mouth and scenting her breath.

After we fucked we made better time. We arrived back at her apartment and we had the place to ourselves. Claire had a roommate, but she was already finished for the semester and had gone home for Christmas, so we’d be completely undisturbed.

Claire had the ground floor apartment and her room was at the back in an extension built off the kitchen that jetted into the yard. 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 then charmed Claire by telling her how much more I would appreciate pissing in her mouth than anyone else I could think off. Admittedly 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 and certainly Claire seemed appreciative. I think that when people are horny as hell there are a lot of things that suddenly seem like good ideas that under normal circumstance could seem a little unsavory.

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 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 and I returned my finger for deeper anal penetration.

We continuing to grind against each other, but with greater urgency. Again I removed my finger from Claire ass and this time offered it to her to suck. Claire accepted and her mouth worked my fingers like she would a delicious cock. I could feel her tongue circling my fingers 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 with a foot on each side of her, with my right knee braced against the back of the couch and my cock 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, helping by guiding the back of her head for greater penetration. Under normal circumstance this would have been the start of a great blow job and would have been expected and welcomed, but a piss blow job has different needs. I told Claire that my cock just needed to relax to piss and to let me hold my cock still in her mouth until I started to 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 mouth.

I'm not exactly sure how long it took for me to start to piss, but it seemed 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. If it were remotely possible, I imagine that I could easily spend days with my cock in a mouth like Claire's. Despite the sense of anticipation there's nothing that I couldn't enjoy about resting with my cock in her mouth. I think for girls though it's tough 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, on the delivery of my piss the anticipation was weighing on me too. Looking back the anticipation of how my piss would be received when it flows for the first time into girl's mouth is always thrilling. Will it be too much for them to deal with or will they readily drink it down? Will they hate it and muddle through or will they love being so filthy? Since Claire was only the second girl to drink my piss I hadn't really yet broken down my understanding of everything that I was enjoying, but I did know that I was beyond turned on to have such an attractive girl as Claire so willing to drink my piss.

I wish I knew how the wait for my piss affected Claire. Did it make her nervous? Did it make her impatient? Did it build excitement? I'd love to know. In the meantime to sooth us both I stroked and ran my fingers through her hair until the first trickle of piss 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 mixed with the sperm that remained in my cock from our fuck in the park. With Claire's head tilted slightly back and the head of cock fully engulfed, I filling her mouth for the first time with a lush mix of sperm and 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 of piss into her mouth. Claire's eyes were closed in a look of serene repose, seeming every bit like someone intent on enjoying every sensation and taste that until this moment was foreign and unknown.

Claire 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 urination. Not only for me, but honestly for Claire too as she barely spilled a drop. I tried to pace my piss so that Claire wouldn't be overwhelmed. It's not always the easiest thing to do, especially with a hard cock and she did have my cock rock hard. I let Claire manage my cock while I concentrated 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, but her first and few spills happened when she failed to master my flowing cock discharging at the back of her throat. It wasn't so much the Claire would choke; she was pretty dam 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 and dribble from her chin, running down to her beautiful breasts. There never seemed to be so much piss lost to reach the couch, but Claire's neck, shoulders and tits were dappled with droplets of piss that seemed to willfully 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 liked her sucking my pissing cock, I loved tilting her head back and filling her open mouth with piss and hearing my piss splash into her mouth. I especially adored when she looked me in the eyes as she would swallow a mouthful of my piss. Her eyes would flutter and close as she drank my fluids and then brightly reopen with a pleased intensity.

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 stretched extending arms and uttering an uncontainable, "Wow!"

Countering with a satisfied smile Claire purred her agreement, "Wow."

Since Claire's roommate was a non-smoker, smoking was, normally verboten in the apartment. However, in light of her roommate's extended absence and Claire’s recent disregard for normal etiquette concerning the consumption of human waste, she decided that breaching house smoking rules would be acceptable. Sitting back on the couch together I lit up one of my smokes and we shared the cigarette. I had my right arm around Claire while we smoked and she cuddled up against me. The feel of her soft damp breasts felt great against my skin and the heat and taste of Claire's mouth augured well for a continuing great night together. As long as Claire was with me I wasn't planning on using the actual bathroom that much, but I did notice that the en suite attached to Claire's room had a double tub, so I suggested we have a bath together.

Once in the washroom 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."

It's another story, but when I was living with Han I had a brief affair with a girl that I worked with. I was twenty-seven at the time and she twenty, but she seemed much younger. She was so innocent and her body was so slender and girlish. We did so much together, including pissing in each other's mouths. Curiously though she didn’t seem particularly kinky or depraved; it always seemed more like she just didn't know any better.

One day while Han was at work that girl and I took turns pissing each other’s mouths. I swallowed some of her piss, but I mostly just let it run out. It tasted stronger than I thought it would, but its failure to really excite me might have had as much to do with the absence of the power dynamic I enjoyed. I think I like to be the one pissing and I like knowing that there are girls dirty enough to drink my piss.

I've also 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 submitting to drink it the girl is transmitting power to me, upstream and through my cock and filling my body. It feels incredible. It's not an orgasm, but it's so incomparably pleasing.

In that vein I wanted to show Claire what it felt like to have someone lick her pussy while she pissed and to give her experience of knowing that someone is drinking her warm urine right from her body. Mostly though I was just so turned on with Claire that I was thirsty for her pee and to see how it would feel to be her piss drinking slut.

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 and I especially like to spit it back into a girl's mouth. In this case though, I never really got much of a chance to appreciate 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 in rapt study.

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. It was warmer than her body with a lighter scent and taste than my previous experience. 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 piss flow management to ordinary pussy licking. Instead of sucking on her fleshy cunt to make sure I drank as much of her pee as possible, my tongue explored her piss dampened pussy. Try as I might, no matter how much I tried to lick her dry, her pussy just kept getting wetter. Go figure.

There were a few things that really stood out to 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 starts 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 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 drink a full night's piss. She was so tiny and I had so much piss. To say nothing of the less than fully voluntary agreement that forced her to do it. It didn't awaken any new feelings of empathy in me though; it just added one more facet to the experience to savor. 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.

Meanwhile I was still licking Claire's wet pussy with my head in a puddle of her piss. I slide her down off my face and onto my cock. My cock slide effortlessly into her wet pussy and Claire lowered her face down to mine and in full embrace she licked my face. Taking her turn to show her 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 and finally I said, "Let's fill the bath."

We let the water run and rinsed out the tub, because despite drinking each other’s piss and having it dried onto our skin it seemed somehow inappropriate to bathe in it

When the piss was gone Claire closed the stopper and I fucked her from behind against the tiled wall as the tub filled around our feet. Claire's tits were a real treats to grab while we fucked. They were just so substantial. I liked the way they swayed and their fleshy jiggle. The major swaying of Claire's tits was notably in reaction to the trust of my hips, but there were subtle counter jiggles that though I enjoyed, I couldn't quite fathom. It was as if every time my cock plunged into Claire's cunt, that there was some wire running from her cervix to her tits that set off a secret reaction. Claire's tits had personality.

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 buoyant together in the large tub. We continued to lightly fuck in the tub and I told her that I wanted to shave her pussy - a favorite grooming service of mine. Claire was a little reticent, not the least because her occasional use of her roommate’s shavers was apparently a point of friction between the two of them. Like for anything else that night though, Claire was game and any reticence quickly forgotten. For now we'd deal with smoothly shaving Claire's pussy, and later Claire could worry about smoothing things with her roommate.

I soaped up Claire's pussy and slowly started shaving her mound bald. 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 a soothing 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 reticent 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 asshole. After all, when you've just been fucked in a snow bank at the side of the road, sucked and drank from a pissing cock and had an orgasm while a guy you just met licked your pussy and drank your piss, do you really have a right to deny anal sex? I didn't exactly pose it to Claire like that, 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. I worked my way down to Claire's tits and I feasted on her sumptuous breasts, before running my tongue down to her 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.

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 wetter or hotter 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 with silky smooth ease was accepting first one and then two fingers, in and out 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 now 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 to be for a first time ass fuck, a lot can go wrong if entry isn't smooth.

Before my ex Han introduced us 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 little sodomites seem to at a minimum be able to endure having their back doors knocked in. So despite Claire's declarations beforehand, I still brought a tiny tube of lube in case I could 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 been already working Claire's ass and then re-entered them in her butt to coat her rectum with cool gel. Then 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 I leaned over and 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. If you don't care one way or the other if you fuck her again then feel free to make her wince and beg for you to stop. Actually, human nature being what it is, I think of it both approaches seem to come with their share of repeat performances, though the later may require a false promise not to fuck their ass again. There were a few girls that I made this promise to repeatedly. Just like Lucy, I would always pull the proverbial football away, and just like Charlie Brown their backsides bore the brunt.

As Claire requested I slowly pushed the head of my cock into her virgin asshole. With uncharacteristic patience and careful deliberateness I worked my cock deeper and deeper up Claire's ass.

Claire had flatted out on her stomach and I could feel the tension in her as she accepted my cock. Her body was under mine and with my head behind her shoulder 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 obscenely seductive.

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 her impalement 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 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 the unyielding constraint of her rectum, but not so much for Claire to try to escape from my cock.

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 hers wet pussy on 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 a reticent ass fucker shouldn't be pressed too hard or given 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.

I swung Claire around to the side of the bed, so that I could stand on the floor. Claire had a fairly high bed that was an ideal height for me to fuck either a pussy or an ass from the floor. I positioned Claire with her butt at the edge of the bed and her legs up over my shoulders. I could look down and see the fleshy pink lips of Claire's pussy, all open and glistening with her juices. I also had an unobstructed view of Claire's once 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, empty and 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 the 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 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 to raise her hips, we increasingly worked together towards our orgasms.

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, that'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 good, 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 what my complete situation was. 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 just got up and said "If there's one thing I can't stand it's someone who can't be trusted!"

Claire grabbed her coat and briskly strode out the door. Stunned and embarrassed, I picked at my food as I waited for the waitress.

After I paid I walked back to Claire's to try to explain, but she either wasn't home or she 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 and I was 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 theirs 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 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.

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 inviting me to a now passed New Year’s Eve party, the next two were hang ups and then 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 roommates 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 the 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.