A White Christmas

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Cross-dressing Santa Finds Unexpected Fun.
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Ever since I tried on my sister's tights when I was a kid, I've had a strong attraction to wearing pantyhose. Fast-forward 40+ years and I still love wearing them (and heels) in various forms, but now I need to shave my legs for them to look their best on me!

I'm not what you would consider a "full-blown" CD - I'm not even close to passable as a woman - but I have always liked how pantyhose look and feel on my legs and butt. I'm also somewhat of an exhibitionist and I occasionally go out flashing to get my thrills. Finally, although I like sex with women and consider myself straight, I am attracted to a well-groomed cock, too!

It was around Christmas time and I had a Santa suit that I picked up when my kids were little. It got put away and I kinda forgot about it for a few years. One evening while the misses and kids were out of town, I was strutting around the house in my heels and suntan hose, legs freshly shaven for the occasion, when it occurred to me that I still had the Santa suit and thought it might compliment my current state of dress, given the time of year and all. I retrieved it from the attic, slipped on the jacket and checked myself in the full-length mirror. "Seasonably hot!" I thought as I spun in front of the mirror to get the full view. The jacket was just barely long enough to cover all but the very bottom of my butt, and with the heels and pantyhose - it was perfect for the season and my mood!

I hurriedly put on a pair of sweat pants and sneakers, threw my heels in a bag, jumped in the car and took off for the downtown area to spread my version of holiday cheer! Once I got to a secluded place away from my neighborhood, I pulled over, kicked off the sneakers and sweats and slipped into my 4-1/2" black heels. I was back in the car (sleigh?) in a minute and off I went on my journey.

Initially I was a quite nervous driving around among other motorists and pedestrians wearing essentially nothing below the waist, but I soon calmed down a bit, reasoning there was very little chance of a passerby being able to see how undressed I actually was. I mean, driving around in a Santa jacket at Christmas time isn't exactly unusual or suspicious, and that's the most anyone could see without walking right up to the car and looking in which, I rationalized, wasn't likely to happen. Feeling a bit more relaxed, I started enjoying my little erotic scene, secret though it was.

After a short while I decided to get a bit more adventurous. I came to a stop light and there was a car with three ladies stopped next to me. The ladies yelled out of their passenger-side window, "merry Christmas, Santa!" I waved out my open window and repeated back to them, "Merry Christmas!" I then pretended that I need to get something from the trunk while the traffic was stopped. I got out of the car and sauntered back to the hatch, all the while trying to be as natural and un-reacting as possible. I grabbed a package from out of the hatch, threw it into the back seat and hopped back in behind the wheel. Well, there was a lot of hooting, hollering and fan-fare from the car next-door - "Ooooh, you the bad bad Santa!" one of them said. Before the light turned green and we went our separate ways, they let me know that they thought my outfit was pretty sexy! Just the encouragement I needed to hear to continue my escapade!

I stopped a few more times when there wasn't too much traffic and gave a quick glimpse to a random pedestrian or someone waiting for the late bus home. I kept a "safe" distance, so as not to freak anyone out, but close enough to give a good show. I got a few cat calls and a few troubled looks as well, but in all, it was going OK and I was having a bit of fun.

I was driving a couple blocks off the main street when a voice called out, "hey Santa!" I didn't see who said it or exactly where it came from, but it was a male's voice and it came from the sidewalk behind a row of parked cars. Feeling a little less timid now and wanting to investigate the interest in my costume, I U-turned a couple blocks down and headed back toward the shout-out. A man stepped out from between the cars parked along the curb, flagging me down. My heart was racing as he approached because he was about to see right into the car and get a pretty good view of my scantily-clad bottom half. It took a concentrated effort for me to stay calm and not overthink things. I just pushed the button, unlocking the passenger door with a familiar "chunk." He opened the door and said again, "hey Santa!" having not yet gotten a full view of me. With the cabin light on, if there was any question of my apparel up to that moment, it was answered now! When he looked in, his eyes lit up. He flashed a big toothy smile and in perfect Barry White tone said, "Allll-righhht!"

"Can I give you a ride?" I asked and without hesitation he jumped in and we took off down the road!

"Whatcha doin' dressed up like that?" he asked, not in a judgmental way, but more like a prodding tone - like he knew why, but he wanted to hear me say it.

"I'm celebrating the Holiday spirit," I said, coyly. I turned briefly to look him in the eye and asked, "Wanna join me?"

"Yeah man, I'm down!" chuckling a bit as if to say, "you don't have to ask me twice!"

"I'm Hershel," he said.

"I go by Jimmy," I replied.

"Oh, OK, that's cool with me 'Jimmy.' You got NICE legs...can I touch them?" I grabbed his hand and placed it on my exposed thigh and he gently carressed me from knee to hip - his touch was intoxicating. Any sense of panic I had moments before was suddenly overcome with excitement. "I think this is going to be good!" I thought to myself.

Hershel must have detected my arousal because he quickly took his hand back off my hip and, without taking his eyes off my legs, hooked his thumbs inside the waistband of his sweats, lifted his bottom off the seat, and dropped trau down to his ankles with a fluid calmness that suggested this was nothing new to him.

I needed to keep my eyes on the road, but I was now distracted by something I had only previously seen in the highest quality porn vids. Hershel was a little taller than average, with a healthy, somewhat muscular build and a confident look about him. And he had every reason to be confident - he was very handsome by any measure and his cock was nothing short of glorious - already very firm, he stood easily 9 inches with a generous, but not disproportionate, girth - and I was eager to service it!

"Where should we go?" I asked Hershel. He gave me directions to a quiet park nearby and I made our way there just as quickly as I could. I couldn't get the parking brake activated quick enough...I jumped out of my seat and went around to the passenger side to open his door for him. With his sweat pants bunched around his ankles he had a bit of difficulty getting to his feet, but soon enough he was out of the car and standing, quite proudly, before me. There was nothing to say - I dropped to my knees beside the car and took that beautiful ebony shaft into my mouth. Before long I had gotten comfortable with his size and was worshipping his entire length with my throat. With one hand, Hershel gently rubbed the back of my head while bracing himself against the car. I took his other hand and firmly placed it on my head, suggesting that I'd like him to be in charge. He took my hint and slowly increased the rhythm of his cock gliding between my lips. Hershel was soon thrusting forcefully into my mouth, which salivated profusely as his large, hanging shorn balls slapped the underside of my chin. I was becoming dizzier with lust the longer we went at it.

Suddenly, Hershel took a small step back, dislodging himself from my hungry mouth and asked, "can we go all the way?" Normally I keep my bi activities to oral, but I had been thinking almost from the moment I first saw his perfect specimen, that I might not be able to resist the temptation to let him play in my backyard, and I had the feeling he was going to ask! I hesitated briefly and told him I was nervous about the idea, but he said he wouldn't be able to finish on just a BJ, and he promised to go easy. I thought about it for just a moment and, kneeling in front of him directed, "When you cum, I want it on my face." It wasn't a request.

"I'll be a good boy, Santa!" he chortled, acknowledging that he wasn't in charge of everything!.

My heart pounding now in double-time, I clambered back on my feet. The combination of my quivering legs, the un-steadiness of my stance in heels and my vision blurred through the tears of deep-throating his big cock caused me to stumble a bit as I turned to face the car. Hershel grabbed me by the waist from behind to provide some support and I involuntarily gasped when his rigid meat brushed between my cheeks. I leaned over the hood, bracing my upper body with my arms, elbows locked straight. Hershel began to slide my hose down over my backside when I reached behind and pulled them back up.

"Second thoughts?" he asked.

"No," I said matter-of-factly. "I want you to rip them open so you can fuck me!"

Resuming my position on the hood, Hershel wasted no time in grabbing the back of my hose with both hands and pulling them apart across the seam to gain access. He quickly but gently guided his bulging head to it's target and slowly worked it in, going a little deeper with each stroke. It was a bit painful at first, but before a minute had passed (or was it ten minutes?) Hershel was thrusting to the hilt, his lap slapping into my butt, filling the chilly night air with a clapping noise that sounded to me like thunderous applause! This must have really been his kinda scene because before very long Hershel's steamy hot breath whispered over my shoulder, "do you want a white Christmas, Santa?" I involuntarily grinned from ear to ear and exclaimed, "I love a white Christmas!"

As soon as Hershel pulled out I spun around and dropped to my knees with my mouth open wide, tongue sticking out as far as it could reach. I leaned back a bit and braced myself by holding the ankles of my nylon-clad legs. Hershel said with a grunt, "Damn Santa, you're so fuckin' hot!" With that he let fly with an enormous torrent of cum that plastered my face, tongue, hair, jacket and lap at least six times as he groaned with a deep passion. I licked my face clean the best I could and cleaned up the rest of me with a towel that I kept, "just in case!"

Our adventure ended as quickly as it began. I drove Hershel back to where I picked him up and we said goodbye. I go back there often, hoping to cross paths with him again.

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4 Comments
pantylvr2pantylvr2over 1 year ago

Very hot, loved it

Hornybim70Hornybim70over 1 year ago

Loved the story, very very hot and wished I were Santa!

gest90gest90over 1 year ago

i read that wishing i was Hershel, then i pictured myself as him, then i was imagining i was him, all signs of a good story. i am a very picky reader & i don't mind a detailed description of someone when it is setting the scene for an original sex scene that doesn't use stereotypical language. as for being 'passable'? beauty is in the eye of the beholder & i've met a few mature men who wouldn't attract me, who after some make-up, hair & wardrobe became attractive females. naturally younger men who were/are beautiful females but the more mature who have been dressing for a long period have an unique persona that is more sexually attractive & attracting than any other gender or mixture of two or more.

that's my opinion & your story conveys this perfectly. well worth developing further.

AnonymousAnonymousover 1 year ago

Hey, that's not the way it's supposed to be. Santa is supposed to visit every neighborhood and give all the good little boys a nice gift. I've been especially good this year, so Santa, what do I get. ;-) MLF

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