CROSSDRESSER IN PICNIC AREA

his is my first attempt at a fictional/fantasy story. All my stories thus far have been true, honest, and accurate, as much so as I can recall. But I kind of ran out of true stories that were worth sharing (for now, but I’ve got some ‘irons in the fire’ and hopefully I’ll have another true story to share fairly soon).

The story I will tell here is something I would love to happen for real soon, remaining at this time, however, a fantasy. Again, this is NOT a true story. Hope you enjoy, and as this IS fiction, I welcome any and all comments on whether or not I can write for real or if I should just stick to true stories or to being a reader LOL.

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Written as if a true story, remember, this one isn’t!

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Sitting around the house late Saturday night, wife sleeping in the family room, me bored, nothing on TV. Hundreds of channels yet nothing to watch. Scanning through the stations trying to find something worth my attention, I catch a commercial for a clothing store chain. Bon Ton or Kohl’s or Target, don’t recall, don’t care, I was just captivated by the hot models in the hot fashions they were advertising.

Hot because I’d love to fuck them in what they’re wearing, as well as GET fucked while wearing what they were wearing on the TV commercial! Sexy minidresses and tights and ankle boots and high heels, in vibrant colors as well as black, my all time favorite ‘must have’ color. 98% of everything I own is black. It’s a foolproof, any occasion, any season color that HAS never and WILL never go out of fashion. It also provides a much better chance of blending into the night so as to not attract unwanted attention on those occasions when I am walking around a park or some other dark, secluded yet public place. I love black. Yes, black cock too.

Being a crossdresser, and really, really into it, I can honestly say I own ‘more skirts than shirts’, more nylons than socks, more dresses than pants. I so hate the clothes that society, in its cruel, closed-minded intolerant attitude, SAYS I should wear. I wish we lived in a TRULY free society, free of persecution and bigotry, free to walk down the street wearing whatever the hell you wanted to wear, without the fear of being beaten or killed.

But that society doesn’t exist, and people like me are forced to stay ‘in the closet’ and hide our true identities. Two gay men can walk down the street holding hands and might get some dirty looks, and yes, they still might get beat, but they have a much better chance of getting where they’re going unscathed compared to a man in women’s clothes, even a convincing one. As long as it’s known that he’s a man, the crossdresser or transvestite runs a much higher risk of being harmed, at the least shamed and embarrassed in front of anyone around.

So, bored and now horny and turned on by the beautiful women in their beautiful outfits, I knew something had to give. I was already wearing a pair of panties and silky sheer pantyhose to bed, so I just lay back and start to play with myself. After a few minutes, I’m really not getting anywhere. There comes a point in time when what pleases you up to that point, simply no longer offers the same pleasure, satisfaction or fulfillment. I needed more. So I grabbed my phone and started through my Internet favorites under the ‘porn’ category, which consists of fully-clothed-sex sites and shemale/crossdresser sites.

Browsing through these, however, only succeeded in making me more horny, yet less able to satisfy myself. I needed more. I needed to do what they were doing in the videos! Now, I’ve been screwed many times before, and I love it, but it’s not something that just happens. It takes a lot of effort, with placing an ad and weeding out the phonies (with only marginal success), and having someone actually show up when they say they will.

And after all that, they have to be able to get it up and perform. I can’t tell you how many letdowns I have dealt with. Why do these guys who can’t get it up even bother replying to a sex ad?

So onto my favorite website I go. Craigslist! Not 100% successful, but definitely affords the best chance possible compared to any other means of hooking up. I place my ad: “Crossdresser looking to get fucked, outdoors or your place.” I got plenty of replies, all liked the outdoors idea, as nobody had a place they could use. That’s fine. It’s dark and late.

My wife knows about my crossdressing and is cool with it, and she knows I like to take a late night drive while dressed. She just doesn’t know what I actually do when I go out. Well, usually I do just drive around, but occasionally I’ll meet up with someone like I will tonight. I picked the one reply that sounded the most sane, and normal as possible. We talked about what we’d do, and got very turned on, more so than we already were!

There is a 24-hour food market near our home, with a large parking lot. I prefer to meet somewhere that is still open, as it doesn’t draw the attention of the local police patrol. We agreed to initially meet here, talk for a few minutes, kind of releive some nerves, and go from there.

Now I just had to figure out what to wear. I decided to keep my black, silky sheer pantyhose on, over my black boy-shorts. I chose one of my usual favorites, a short black cocktail dress (you know, ‘the little black dress’) that I’ve been fucked in probably more times than a slutty woman would have been had SHE owned this dress. For my shoes I decided to go out of my ‘comfort zone’ (which usually consists of shoes with straps) and I slipped on my 4″ black pumps.

I can walk pretty good in women’s shoes, but I don’t usually have much opportunity to walk far as my shoes are usually up in the air! Now I’m not passable, I’m up front about that. But I shave my face, legs and chest, and in my auburn wig and a little makeup, from a distance I’m not too bad, and from behind I’m smokin! Never had a complaint, I can assure you of that.

I grabbed one of my smaller purses, tossing in my license and cards, my cell, a couple condoms, a couple paper towels and small bottle of lube, having already used it to make sure my hole was nice and slick for what would hopefully come shortly. I head to my vehicle, luckily parked in our attached garage so nobody is none the wiser should anyone be up and looking out their windows at this hour. It’s great to at least have THIS freedom, to be able to leave my house already dressed instead of trying to find a place to change.

I get in, close the door, and hit the garage door opener, starting my truck and heading to the meeting site. It’s only a mile from home, so I’m there in a minute. Driving in 4″ heels is a little challenging, but I manage nicely, though getting IN my truck is even more of a challenge, as 4″ heels don’t work well with 3″ tube step bars, needing to be extra careful so as not to turn an ankle. I turn off the dome light so whenever I open the door, I’m not giving a show to anyone who wasn’t invited to the ‘party’.

I pull into the parking lot. He is here, waiting, as promised, in an unused corner of the lot. That’s always a good thing, though many times previous, when I was stood up, it was a relief as well as a disappointment; it’s always nerve-wracking to meet a total stranger for sex, especially another man, it’s a big chance one takes. But here he was, obviously serious and committed to do what we talked about.

We had agreed that if he liked what he saw, he would get in my truck and we’d go find somewhere dark, private…and outdoors. I pull up to his car and introduce myself. He’s white, about 45, maybe 6′ and about 230 pounds, decent shape, and seems like a nice, normal, safe guy who just isn’t having his needs met at home, which is always the case in my experience.

Even single guys like CD’s because they can get their rocks off by fucking a warm body in a short skirt, nylons and heels, without the wine-and-dine drama of dating and all the shit associated with just trying to get laid. A warm, wet hole is a warm, wet hole! Most of these guys only do it once, some regret it after the fact, and many don’t even consider themselves bi or gay as long as their cock is between stocking-clad legs hanging out of a short skirt.

I open my door to show him the goods. He is quite happy with what I have to offer. So he climbs in my big truck, having a much easier time of it than I did just 5 minutes before. He slowly reaches over and gently caresses my smooth, pantyhose covered legs, his hands surprisingly smooth for a guy. Turns out he works with computers, so his hands wouldn’t be rough anyway.

He runs his smooth hand along my leg, a tiny bit higher each return trip toward my dress, eventually reaching UNDER my dress, slowly inching toward my own manhood. I can tell he is very excited, as he is squirming in his seat and his pants look like they’re about to bust open.

I slowly reach over and rub his tool through his jeans, feeling his huge member getting even bigger and harder! I couldn’t wait to have this cock stretching the walls of my ass! He unzips his pants and frees the largest cock I had ever seen to that date. I’m not into oral, but something was different about tonight.

Tonight, for the first time in years, I didn’t just feel like a bisexual guy in drag, but I actually felt 100% real woman! I can’t explain it, but for now, at this moment on this night with this man, I WAS a real woman. I mean, I KNEW I WASN’T a real woman, of course, but I FELT a real woman, and it was a feeling like no other, a feeling I never, ever wanted to end, though I knew it inevitably would. I would find myself doing, and feeling, things I never have before.

I leaned over toward his lap and took his huge cock in my mouth. I’ve only ever done this before merely as part of the ‘package’, or just to get someone hard enough to give me what I wanted. I’ve never enjoyed it, never craved it, and certainly would NEVER meet just for a blow job.

You want me to blow you, if you insist, I will, but only if I get what I want in the end (ok, pun INTENDED). I could only take so much in as he was truly huge, but I did my best, and for the first time EVER, I was ENJOYING giving head! I was really running with the moment, again hoping it would never end.

I lifted my head and told him we needed to find that dark, private place, that I would pick up where I left off, and how much I needed that monster in my ass! I knew it might hurt…a lot, but I didn’t care. It would only hurt at first anyway, but some pain is part of the pleasure. I put the truck in drive, his hand never leaving my legs, and drove to a place I knew well, but had never taken, nor ever met a lover here. It was a popular place to fish in the river adjacent to the small parking lot, but luckily tonight was deserted.

I parked my truck, and went down on him again. His breathing was short and hurried, and I knew he was about to cum. I didn’t want to lose out on my opportunity for this cock pounding my ass, so I asked him how long it took him to recover, that I would let him blow his load in my mouth if he could still manage to fuck me soon thereafter.

This was a big deal for me. I had a bad experience once, the very first blow job I ever gave, the fucker came in my mouth without telling me, therefore souring forever how I felt about oral sex. Here I was actually WANTING him to cum in my mouth! He assured me he could be ready again in 20 minutes or less. That would work, because there was a picnic area through the fence of the parking lot, with lots of trees and picnic tables.

That’s where I wanted him to fuck me, and I wanted to make the moment last as long as possible. So I went back to work on his beautiful, huge cock, mine now as hard as his. Just then, he puts his hand up my dress, and starts fingerings MY hard tool. It was an absolutely amazing feeling! I felt my orgasm building.

It didn’t take long before I sprayed my built-up cum in my panties, I could feel it run down my balls and in different directions, the most powerful orgasm I’ve ever had! About 10 seconds later I felt his cock swell, then pulsate as his load exploded into my waiting mouth.

It’s so different when you expect it, and it didn’t hurt that I felt the way I did, like a total woman, a real cock craving slut! I hadn’t decided whether I would swallow or not, but I wanted to have the full experience as much as possible…so I closed my eyes, and swallowed his cum, while cleaning off the rest from his cock.

We both sat there for a few minutes, both out of breath and tired from what we both agreed was the best climax we’ve ever had, but I told him his next orgasm might be even better. I really couldn’t believe I just swallowed a load of cum, a huge load it was, too! We got out of the truck, my cock sticking to the inside of my panties and pantyhose, and actually starting to get hard again.

He said his was also coming back to life. We walked toward the picnic area, my 4″ heels clicking on the pavement, soon to be sinking into the grass of the picnic area. He reached for my hand, and held it as we walked toward the darker darkness of the night, into the wooded picnic area.

This was the most erotic thing I’ve ever felt, as we walk from the safety and privacy of my truck, to the unknown of a public place, separated from the safety of my truck by an open parking lot. Hopefully nobody else will come down here while we’re here, but it’s a gamble.

Public places always are, which is also what attracts me, and others like me, out to public places. I’m already hard again, so is my lover for tonight, he exclaimed. I reach over with my hand, still held by his, and feel his hardening cock, still out of his pants! He never put it away.

Sweet. I stroke his hard tool with both our hands, bringing his erection to full size once again, not 10 minutes after shooting his hot load into my mouth. I wanted this to be as exciting and as risky as possible, at least as far as a deserted picnic area goes. Still nobody has driven down here. I tell him I want to go as far as we can, or at least as far as I could walk in the grass in these heels.

I now have pre-cum forming on the end of my cock, as does he. Just as we get to the last picnic table, a car comes down to the parking lot. The driver shuts off the lights but doesn’t get out. There’s no way for us to be seen…unless the occupant or occupants of the newly arrived car got out and walked into the picnic area. Maybe they’re fucking each other in the car. Well, we weren’t going to worry about that for now. Besides, it was turning me right the fuck on, more than I thought possible. He didn’t seem bothered either, and I did feel safe with him anyway.

I sit my ass on the end of the last picnic table, opening my legs so he could get closer. He stepped closer and held me, then…kissed me full on the lips! It was fucking magical! I tingled with all of my senses, and was actually trembling somewhat. I couldn’t believe this was happening, and HOW it was happening. I told him I needed him in me now, and asked if he was comfortable not using a condom.

He said he would be more than happy to plant his seed in me, first asking for my assurance it was safe. I assured him it was, I was married and so was he, so the risk was minimal, if any, but worth it! He gently guided me back onto the picnic table so I was laying on my back, and raised my legs atop his shoulders. He reached down and pulled down my pantyhose.

His cock already wet, and my hole well lubricated, i was about to receive what I’d been waiting for all night. His cock, huge as it was, amazingly, and with the most sensational feeling, easily stretched past my opening and buried deep in my ass. He leaned over and kissed me passionately while making love to the woman I felt I was at that moment. The woman I WISH I was!

It was the most incredible feeling ever, I felt so full, so feminine, so happy, so amazing! He pumped in and out of me for longer than anyone previous to him ever even came close to. His endurance was amazing, and probably helped along by his previous orgasm from my blow job I had given him not long before. With him still going to town, we never noticed the couple walking towards us until they giggled and turned around, picking another table a few down from ours.

We giggled ourselves, hearts pounding even harder now, continued on our quest to heavenly bliss, not giving two shits about having an audience. I was actually turned on like never before! I’ve never fucked in front of anyone! I don’t know if they were even paying attention to us, but it was a huge turn on nonetheless. I lost all track of time, hoping against hope that this moment would never end. But it would end, and when I felt his cock swell and his breathing get shorter, I knew the end was near. I felt his cum shoot into my ass, actually felt myself getting full, felt the warmth and expansion.

I asked him not to pull out til I took care of myself, but he started rubbing my cock through the front of my pantyhose which were still pulled up in front, and with his cock still in my ass, I came again, harder than I had after he first rubbed me to orgasm. Even after he went limp he still filled my void more than any HARD cock before him. When he pulled out, I stood up and pulled up my pantyhose, my legs wobbling beneath me. I felt his seed start to seep out.

We start walking back toward the parking lot, toward my truck, and right toward the couple who were doing the same thing a few tables down from where we were! At night, as dark as it was, it was doubtful they knew I was a guy. We walked past them, holding hands again, my heels sinking into the grass as I walked. About halfway to the parking lot, I felt my bowels rumble, figuring it was because of all the cum he filled me with. I started feeling like I had to shit, or at least release gas, and cum. I figured what do I have to lose? I’d rather feel comfortable.

I was going to wait til I got home to let it all out, but I was getting hard again already! And guess who else was getting hard again as well?! Well, here goes. I stopped trying to hold it in, and I let his cum gush out of my hole, filing my panties, and running down the legs of my pantyhose! I may have shit a little too. It felt amazing, his load of cum sloshing around in my panties as I walked! I was so wet.

As we approached the parking lot, another car came down the road. My lover grabbed me, held me and kissed me, creating the illusion of a couple making out in the night. The two people in the car parked, and got out walked toward us! We stayed locked in a passionate kiss, the couple passing by without a second glance, and continued toward what is obviously a sex hot-spot. As they disappear into the darkness, I was totally turned on again, and wanted him to take me again. He agreed, and I suggested, against all better judgement, to walk back into the picnic area! We picked the first table this time, my feet just unable to walk on anymore.

This time I bent over and he pulled down my already soaked pantyhose, and slid it in to my sopping wet cum-hole. I lay forward onto the table top, and he grabbed my hands and pulled them behind my back. He paused for a couple seconds, then I heard a metallic sound, then…HANDCUFFS! Dream come true! I’m handcuffed, bent over a table, taking a monster cock in my ass for a good 15 minutes straight! Best sex ever! Finally he swells one more time, and shot another quart of cum inside of me! I felt full again, and like I have to shit again too.

I asked him NOT to take the cuffs off until we get to the truck! This was hot. Before we start back, he pulls my cock out of my pantyhose and strokes it to orgasm! I saw my cum shoot a good 20 feet in the moonlight!

We get to my truck and he takes the cuffs off, and I let his cum shoot out of my ass, filing my panties even more, followed immediately by the biggest shit I’ve ever taken! Uh oh! I couldn’t believe what just happened, but I was ENJOYING it! The whole night has been amazing! Now I have a huge load of shit in my pantyhose, squishing around my thighs, working it’s way down my nylons.

I had a garbage bag that I knew I’d need in the event I got fucked without a condom, and I put the bag on my seat. I apologized for the smell, he was cool with it, saying he was actually getting hard AGAIN! I climb in, already difficult in heels, take a deep breath, and sit in the drivers seat. My load of cum and shit squeezed up between my legs, engulfing my cock and balls, and actually felt great! I might have to do this again!

I drove back to the market parking lot, and dropped him off at his car. I said how I’d love to see him again, how much I enjoyed this night! He said he had a great time as well, and said how much he wanted to see me again too…then he asked me how long it would take me to go home, shower and change into a clean outfit. We agreed to meet again in about an hour, and this time we hoped there WOULD be people at the picnic area!