Crossdressing, Piss and Sex

This is a work of fiction, a fantasy that I would love to come true. It also contains 'pissing' (aka 'watersports'), crossdressing, and a crossdressers sex with men, so if you are not into these subjects, this story might not be for you, you have been warned. Also, comments are welcome, but please note, I'm NOT a professional writer, if I was, I wouldn't be writing for free. I know I'm not perfect and my style might not be what you like, but it is unique, and it's mine and I write because I enjoy writing and my readers love reading them, and my readers are the primary reason I do it at all. I also proofread and hope I catch every grammatical inaccuracy, but something might slip by, and I'm sorry if that happens, I try my best. Hope you enjoy.

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One in the morning.

I am a kinky crossdresser. Have been most of my life. I'm not 100% passable, but close. I really enjoy going out late at night to a normally secluded parking area near where I live, which is adjacent to a golf course, when I can't manage to arrange a hookup. No houses around, and it sits at the edge of town along a main road but is far enough from the road that you cannot see anything unless you actually pull in. There are no lights either. There is a small pavilion with two picnic tables under it, and it's surrounded by trees. The area is well maintained throughout the year, and is a carry-in, carry-out spot...you bring it, you take it.

What I normally do is come here late at night, dressed up, leave my pickup truck, and walk to the pavilion. I'll then sit on the picnic table and jerk off. Sometimes I'll blindfold myself, not allowing myself to remove it until I cum, therefore running the risk of someone pulling in while I can't see them, sitting there on a picnic table, dressed in women's clothing, stroking my cock til I blow my load. Self discipline is everything, I always stay true to myself when doing something like this. Being late at night, after midnight usually, reduces the risk, but there are still quite a few vehicles that pass by, though over the years I have seen that hardly anyone ever pulls in at night. So it's a 'safe' risk, yet still risky enough to be exciting. One particular night will forever be etched in my memory.

It was a Thursday night in June. I prefer weeknights because most people are in bed by 10 or 11, further reducing the chances of being caught. I was sitting around the house, bored stiff, contemplating what to do. I decided to put an ad on Doublelist for a hookup, but not just any old hookup, I wanted this one to count. I was experiencing a 'dry spell' and really needed to have some dicks in my ass, and soon. Being a weeknight, I was kind of playing against the odds as I never usually get too much interest during the week, but still, not everyone works days, weekdays, or work at all. They just had to have transportation...and show up. My ad stated my stats and what I wanted:

'52 y/o CD, dress fully with wig, short dress, nylons, etc, looking for s e x and would love a bunch of guys to piss on me and soak me down, tonight at at the parking area by the Vista Springs Golf Course at about 1:00 am. I will be bent over the picnic table with a blindfold on, lubed and ready to go. Do me, then empty your bladder on me. Don't reply, just show up. I'll plan on being there for an hour, longer if the interest is there. Please be clean and d&d free. Any age, race and body type, I won't even see you. Don't be shy. '

I posted the ad at around 9 pm, and by 10 I had received quite a few replies (nobody ever listens), all of them basically saying 'I' ll be there' or the like, and one asked what I would be wearing. I didn't reply to anyone, I left it at that, and began getting ready, though I had a couple hours yet...plenty of time. Before I began my transformation, I went to the garage and got a painters plastic 'drop cloth' and draped it over my seat in my truck. If I was going to end up covered in piss, I didn't want to ruin my seats. I disabled the outside motion-activated flood lights so I wouldn't be exposed when I left the house dressed as I would be, and went back inside to start preparing for what I hoped would be an amazing night.

I took a shower and shaved everything I could, face, legs, pits, chest...it would be too dark for anyone to notice any body hair, but I would know it was there and I know it would bother me. Not to mention, nothing beats the feeling of sliding a pair of nylons up a freshly shaven pair of legs! Drying off, I head to my room and my walk-in closet, filled to capacity with skirts, dresses, hosiery, shoes, wigs, purses, jewelry, and a makeup table with a large mirror and light. I would walk in a man, and walk out a woman. The closet got a LOT of use!

I began by lubing my ass real good, then pulling on a pair of black crotchless panties, followed by a matching black lace-trimmed bra, inserting my D-cup silicon breasts. They were amazingly life-like and cost a pretty penny, but they were worth every one of those pretty pennies. I then pulled up a pair of black pantyhose, and as I did, as the nylon slid up my clean shaven legs, every nerve in my body tingled with excitement and anticipation. I then secured a gold ankle bracelet to my left ankle, then I pulled on a tight, black 'pencil' tube dress which came down to just below my ass, showing more leg than most women would ever dare show, but I primarily chose this dress for the material it was made from, which would soak up anyone's piss much better, rather than have it just run off like it would with other, less porous materials. I would skip doing my makeup as my blindfold is a solid, breathable black hood, covering my entire head from the top to my neck, and the makeup would just smear and is otherwise unnecessary for this plan.

Then came my shoes, and for this I picked a pair of black patent flats, easier to walk in grass, and better shows off my ankle bracelet. Topping it all off with one of my shorter wigs, I looked at myself in the mirror and was once again stunned at how I looked. Though I was 53 years old, I pulled it off very well, much better than before I had the bariatric surgery when I was really overweight. Now that I am nearly HWP, I can pull this off much better and have much more success with hookups, as well as a much better chance at passing! Luckily most all my clothes were always stretch material, so 95% of everything still fits well, most fits as it SHOULD now, and I have more options as to what I find at the thrift stores and even regular stores, more availability in the more normal size range.

I watched TV for a bit to kill some time, until about 12:45. I grabbed my small clutch, inserting my drivers license, debit card, and my phone, stuck three condoms in my bra in case anyone insisted on using one, grabbed my blindfold hood, and out of the house I went. The drive took only five minutes, so I arrived at about eight minutes to one. Luckily, as usual, the parking/picnic area was deserted. This would be so exciting! I would hear a car pull in, wondering if it was someone showing up because of my ad, or someone else just pulling in to rest or smoke or whatever, and would they see me? What would they do? Risk equals reward, hopefully that stands true tonight.

I took a deep breath, set my clutch on the center console, and left the safety of my pickup, locking it behind me, glad I got the keypad option so I didn't have to carry keys with me and possibly lose them in the grass. Now you may be asking why I would want to be soaked in other people's piss. Well, it's a fetish, I guess, but it's also a sign that I am a dirty, filthy slut, and this would make it official in a sense. And I just like how it feels to have that hot liquid soak into my clothes, run down my body, fill my shoes...

I picked the spot on the back side of the picnic table, where I was facing the road. I knelt down on the grass, pulled on my blindfold hood...and waited. My stomach was in knots, heart pounding. The anticipation grew to an almost unbearable level. I was hard, had been for a while now, since first getting dressed, but I didn't want to lose the desire to go through with this, so I didn't touch myself, but I certainly will after I'm done tonight. I just hoped that this would pan out. There were about ten replies to my ad, the one I said not to reply to, so I figured at least a couple should show up. I guess I'd see.

I didn't have to wait long. I heard two cars pull in to the parking area. Engines shut off. Car doors open and close. Footsteps on the pavement, turning into a slight shuffling in the grass. I knew they were close when I heard two men quietly talking with each other, hoping that they weren't going to do anything bad to me, but accepting the risk I had taken. It's always a risk.

My initial anxiety calmed when one of the men pulled up my dress, pulled down my hose and panties, knelt down behind me and stuck his cock into my waiting ass, not wasting any time! I never tire of the feeling of when a cock spreads my hole open and fills my tunnel between the outside world and the depths of my insides! I was well lubed so that helped his large tool get inside, where he stopped for a few seconds before starting a relentless thrusting in and out. I didn't know what the other guy was going to do, if he was going to try to lift the hood to gain access to my mouth, or piss on me while the other guy fucked me, but it was an amazing feeling not knowing what was next. Then I felt his hands caressing me all over, squeezing my silicon tits, rubbing my legs, while his friend was having his way with me. Had I known this method of hooking up would have been successful, I would have tried this long ago.

I knew no names, could see no faces, so I could only refer to them as 'guy 1' and 'guy 2', and hopefully there would be a 3, 4, 5 etc...but it was a success even if it ended here. My own cock had been hard the whole time and was ready to blow, but before that could happen, guy number 1 came in me with a loud moan, emptying what felt like a quart of cum into me, and I could feel each pulse and each shot of cum until he pulled out with a wet slurp. He stood up, I guessed, as I could not see anything, and nothing happened for probably a minute, then I began to feel a warmth hit my back, growing in size, wet, flowing, and running down the crack of my ass, running down my legs until it reached my knees and soaked into the ground upon which I knelt. He kept going, and going, I could not believe anyone could have this much piss in their bladder and still be able to fuck someone before emptying it, but this guy certainly did, and his bladder was huge! He single-handedly soaked my entire dress, lingerie, and my pantyhose all the way to my knees, his cum adding to the downward flow of his bodily fluids. I was in heaven!

Guy 2 then let his bladder go, drenching me even more, I could hear piss dripping off the bench of the picnic table onto the ground below, and I felt hot liquid soaking every inch of my clothing and running like a river down my back, through my crack and down my legs. My load was so ready to blow, if anyone or anything touched it, it would let loose with my own load like a cannon. Guy 2 then knelt behind me as guy 1 had done, and started rubbing his limp cock up and down my ass crack, lubricating it while waiting for it to grow. I heard another car pull up, shut off the engine, and close the door. Guy 3, I presumed. I was very glad it was a warm night, though even so, I was beginning to get a little chilled, being soaking wet.

Just then, before guy 2 could start taking advantage of me, all the piss that had soaked me made its way to my cock, which was locked and loaded, and the sensation of that, combined with all the other sensations of everything else that had just happened, was too much for it to hold back, and I shot my load into my panties and hose, adding still to all the liquids that soaked me from my back all the way to my knees, and the wetness was migrating up toward my shoulders.

Guy 2 had finally become hard and slid his cock into my already used hole, now well lubricated with the first guys huge load of cum. Happily, neither one requested a condom, and though it's a higher risk, it's safe to say most men who fuck crossdressers are not gay, most are married and just want what they don't get at home, so while there IS risk, it's much lower as the likelihood of a married guy with kids having an STD is much lower than someone who is gay. That's not science, I know, but I do feel more comfortable attracting married men.

Guy 2 finished in under 30 seconds, I don't think he had been laid in a long time, and I was happy to have made him happy...god knows he made ME happy, they both did! He pulled out and was replaced almost immediately by guy 3, who promptly unzipped and slammed his tool hard into my ass, taking the third spot on the roster. He banged me good and hard, but also must not have gotten any for a while, he lasted maybe two minutes. He shot his load into me but pulled out halfway through, shooting a few shots of cum right on my ass, immediately joining the river of piss and cum from the first two installments. He got up and stood behind me for a minute, then I once again felt a stream of hot piss hit the small of my back, further soaking my dress and underwear and following the path already forged, down my body, over my ass, down my legs, warming me up a little from the chill I had been feeling in the gently breeze.

Guy 3 didn't have as much to offer as the first two, but it was sufficient enough to be very pleasurable. I was bent over the bench of a picnic table, soaked to my skin with the piss of three guys, their cum adding to my piss-soaked panties that were suspended just below my ass, acting as a 'cum catcher' of sorts. When I'm done and pull my panties and pantyhose back up, I'm going to have a real treat! I thanked them for coming (cumming, haha), and they thanked me for being there, and they left me alone and drove off.

I stayed there for a while longer, but nobody else came. I removed my hood and checked my watch, it was 1:18 am. Seriously? All that happened in just 18 minutes? Wow. I decided to wait a bit longer. I had to piss myself, so I stood and got ready to go when I figured, I'm already soaked in piss not even belonging to me, so why not? I pulled up my panties and hose, and let it go. I just loved the warm sensation running down my legs and into my shoes, which had remained dry to this point as I had been on my knees while being soaked down, and that just added to the pleasure of the night.

Then I saw another car pull in, shut off the headlights and the engine, and two guys stepped out into the night. I replaced my hood and assumed my position, on my knees, leaning over the bench of the table. They approached me and one of them asked me to stay on my knees but to turn around and face them. That worried me a little, so I asked why, and he said he just wanted to piss on the front of me. I complied, and was rewarded with both men emptying their bladders, their very full bladders onto me, making me more wet than I ever thought possible. They seemed to piss for ten minutes, though I'm sure it was only 30 seconds or so.

If I had any dry spots before, there were none now...none. I was soaked to the bone, and it felt awesome, wonderful, like nothing I had ever felt before! This was a night that would go down as one of the best ever. I had so far been fucked by three well-endowed men, and soaked with the piss of five. I wanted to equal the number of fuckings I had received tonight to the number of guys who emptied their bladders on me, so I turned around and once again bent over the bench. But they asked me to lay on my back, on top of the table, which I did. The first one, who would be guy 4, lifted my legs onto his shoulders, at which time my own fluid that was in my shoes, MY piss, began to empty and run down my legs and onto his shoulders. I hoped he didn't mind, but he knew what this was all about and didn't seem to care that his shoulders got wet with urine.

He reached under me and pulled my panties and hose below my ass, stepped forward, and slid it in, my ass taking the fourth cock of the night! I don't usually get fucked this many times in a MONTH, yet here I am taking one after another, it's a dream come true. My cock was once again hard, but still confined in the front of my underwear. With my legs in the air, blindfolded and soaked, guy 4 fucked me silly, and for a good, long time. I don't know how long it was, but it seemed to have been 15 minutes easily. Just before he started going faster and fucking me harder, I felt my cock getting hard again, but he came before I could, which was fine, if I had to choose getting fucked or me cumming, I would always choose getting fucked, but don't get me wrong, I will never turn down a chance to cum WHILE getting fucked! When he let loose, I could again feel it inside me, filling me and adding to what was previously deposited in my body.

Being on my back this time, I could feel his cum run up my crack toward the small of my back, a totally new sensation detached from the prior sex. I had so much cum in me and on me, and so much piss soaking me to the bone, I felt like I could float away from where I was. I certainly felt like I was already floating on cloud 9! It would be fitting. But it wasn't over. I never wanted this night to end, and hoped they kept coming until the sun started to rise...though it might be hard to explain to my neighbors why I was dresses as such when I came home early in the morning, not that I had to answer to any of them, but still, I prefer to keep my antics reasonably private.

The other guy, guy 5, took up his position, lining up with my waiting hole and wasting no time, plowed me like it was his last day...god how I love desperate men! They always have so much energy and are so appreciative of what I have to offer, which is what they don't get at home. The only problem is that they don't last very long, but that's ok. I'm just happy to get fucked, having a cock in my ass is a never-ending desire, actually an addiction, that I could never, and would never live without. I am totally hooked, and have been for a very long time now. I only wish I had started sooner, I never even took my first cock until I was about 29 years old...I certainly missed out on a lot of good fucks, but I'm making up for it now.

I could tell guy 5 was on the verge, his breathing increased as did his pace, and his grip on my ankles, my pantyhose now only damp as the nights slight breeze had dried most of the thin nylon material. I had cum right after the first guy banged me, so the next three that followed did so after I had myself cum, and that was an experience unto itself! Never before had I ever been fucked AFTER I came...I usually lose interest, but over the past few years, I have found that I still do have the desire for a cock in my ass after I have blown my load, but up to this point I hadn't had the opportunity, and admittedly, when I'm horny myself, I enjoy the experience more. But tonight has shown me that I want dick in me no matter what my own level of arousal is! This has completely changed my whole perception on what I do...I love dick in my ass, no matter what! I would even take it if I wasn't dressed, should that opportunity ever arise.

Guy 5 had stopped for a minute, his cock still deep within me, to put off cumming. He wanted to make it last, and I was glad for that as my own tool had been hard again from the moment they both soaked me down before his friend had me lay on the table. I so badly wanted to cum again without touching myself, and I felt like I was ready to do just that. When he started up again, I immediately felt my cock twinge, and on his 5th renewed thrust, he hit my 'happy spot', and I came again for the second time that night, having never touched it. The sense of euphoria was overwhelming, like nothing I had ever felt before! While he was still pumping into me with a renewed energy, his friend, who either has an overactive bladder or had drank a couple bottles of water, stood on the bench and once again soaked me with his piss. This time it ran under my bra, around my silicon tits, and reached my neck, where it split off on either side of my neck, running along the table and along my back.