The Late Night Walk

This story is fiction. It did not happen...but I wish it would. It's been a while since I've written anything, but as it's been a while since anything real has happened, I wanted to add another story to my 'collection'. Thank you all who've replied with positive, encouraging words. This is for you. One more little 'disclaimer'...this story is a fantasy about what I enjoy, what I would want to really do, and thus contains, at the end, some pant-shitting/pissing, so if that turns you off...don't read. It's MY fantasy that I'm sharing with you.

I'm middle aged, a bit overweight but not fat, and I love to crossdress. I really love to get fucked while dressed, and embrace that opportunity any time I can. I also love going out late at night, either fully dressed, including wig and makeup, dressed like a slut, or wearing just enough to not be noticed by the casual observer. Unbeknownst to me this night, that very same 'casual' observer would be very alert and at the top of his game, which would work out beautifully for both of us.

It was about 2 am, and finally spring felt like it was supposed to, nice and warm, and a beautiful night. I decided to go for a late night walk, dressed a little risky, but not over the top. I chose a pair of black tights, my black Danskin shimmerey pants, and my favorite pair of black flats. I just LOVE how tights look in flats. Now, close up, it's obvious the pants are women's, and looking at my feet...dead giveaway. But...it was late. The risk was there, albeit lower than had it been earlier, and it's the risk that turns me on so much. But it was late...would anyone really notice?

I left my house for my walk about 2:15. I had to shit pretty bad and the plan was I would walk about a mile down the road, let it out, and walk back home with a huge load squishing around in my panties. I always wear panties and tights under my pants. Always. And I love shitting myself every chance I get. Love pissing too...the feeling of my hot piss running down my tights and into my shoes...LOVE it. So, as I said, that was the PLAN.

I got about a quarter of a mile down the road when I notice a man standing in front of his house. I know him to be alone, usually tending to his maple trees or anything else outdoors, but have never seen him outside so late. Maybe he won't notice. It's dark. I keep walking, my heart is pounding harder now. I'm nervous, excited, horny, and the latter of those feelings is what drives me to continue. Not that I had ANY expectation that anything would happen, but I thought it would at least make my little 'trip' that much more enjoyable, and the subsequent orgasm that much more powerful.

"Hello" I hear from the man. Shit! "Hi" I reply. I keep walking. But he starts walking toward me. Ok...I'm busted. He in no way looks threatening, I just didn't want to feel embarrassed. "Nice night, huh?" he said. I was on the opposite side of the road, and I stayed there. "Sure is" I replied. He says "Love what you're wearing". That's when I realize I'm standing under one of only a handful of streetlights on our rural road! Not right under it, it was about two houses down, but bright and exposed me to anyone with a sharp eye.

"Um...thanks. It's a little fun, and comfortable", not really knowing what else to say. So, I cross the road to greet him, nothing else to hide at this point. We made some small talk and I loosened up and ended up telling him what my plan was for my walk, figuring maybe I could be on my way now. I really had to go by now. That's when he told me he has a foot and leg fetish and asked if I would let him touch my legs and feet. I immediately got rock hard, and it was at that point hoping things would progress from there! I accepted his invitation into his house, and was instantly glad I took my walk tonight.

Inside was a kind of dated but clean home, and we sat at the kitchen table and had a glass of wine. He asked if I would feel comfortable taking my pants off so he could check out my legs. I was only too happy to do this. And he was very happy with what he saw! He drops to his knees and says "stop me if I do anything you don't want me to." He starts caressing my legs and my ankles, which drives me wild! His hand makes it up to my very hard cock, caressing that as well, ever so gently. Looki into my eyes for approval, and after receiving no indication to stop, pulls down the waistband of my tights and panties and takes my hard cock in his mouth!

This feels absolutely incredible! It's the best blow job I've EVER had. I'm close to cumming, I let him know. He moans something indistinguishable and keeps working on my throbbing cock. I can't hold back, and explode in his mouth. He doesn't swallow, and it runs out of his mouth and into my panties. It feels amazing. Even though I just came, I still feel horny. I want him. I want him to fuck the shit out of me! He must have read my mind, as he got up and led me to his bedroom. I lay on the bed and he is once again caressing my legs. I ask him to lick my ankles, I just love my ankles being touched and licked and caressed.

As I lay there on his bed, on my back, my own cum is slowly running down my balls and my ass! He pulls again at the waistband of my tights, this time exposing my ass. I then feel a finger, then two, enter me. I remind him I'm not 'cleaned out' and ask if he'd like me to go empty myself out. "It's ok, I can shower afterwards. I want to watch your load fill your panties when we're done." That made me start to get hard again! He said he had some lube but by the feel of it, from my own cum he deposited in my panties, I didn't need it. He was right, his fingers slid right in and I was thoroughly wet and ready for giving pleasure to my new friend.

His fingers removed, he now kneels before me, my ankles on either side of his neck, and he pulls out from his pants a huge cock! Oh man...I'm gonna love this! He guides his rock-hard manhood into my waiting, willing cock-starved ass and proceeds to fuck me like he's never been laid! It was then I realized he had no condom on. Fuck it. I asked if it was safe to not use one, and he assured me he was safe. Besides, I'd be shitting it out right afterwards anyway, and there's NO WAY I'm stopping the Ecstasy Express at this point. He's banging me for a good 15 minutes when he stops suddenly. Then, to my incredible pleasure, I feel his cock pulsating against my ring...he's shooting his load inside of me! It goes on for almost a minute! It was absolutely fucking amazing!

After it stops, he pulls out and I can feel what feels like a lot of cum running out of my hole. What a feeling. He lays beside me and asks if I would like to do this again sometime. "Fuck yeah! As many times as possible!" I told him I could even come fully dressed and made up, to which he expressed a great desire! I said I'd have to drive over so I could leave from my garage and not walk down my street dressed like that...but maybe I'd have the guts to do just that providing it was really late like tonight.

I tell him I have to get back now, and it's time to relieve the pressure built up inside me. I stand up and turn my back to him so he can watch as fill my tights. I release my hold on my muscle and immediately feel his cum shoot out, coating the inside of my panties, followed by a huge load that I'd been saving all day, for my anticipated solo pleasure. The load of shit totally fills my panties and it's so much that some of it escapes into my tights and down my legs. It's a most amazing feeling. I put my pants back on and he kisses me. Wow. This might be a great relationship we started. I ask if tomorrow night would be ok, to which he was only too happy to affirm. So we are on again for tomorrow night, at which time I will come fully dressed. I might even walk down to his house like that...

We say goodbye til tomorrow, and as I stand outside his house, I need to pee badly, so why wait? I let it go, my hot piss running quickly down my legs and filling my shoes! It was a lot, seemingly going on for 30 seconds, and by the time I was empty, my shoes were filled and my panties, tights and pants were totally soaked! But what a wonderful feeling to walk back down my street with soaking wet pants, a huge load of shit squishing around in my panties and the everlasting memory of just having been fucked, with hopefully many more to cum! Step by step I ponder the question every woman has...'what WILL I wear tomorrow.'