The Leatheress 103 - "Closing Time"

As far as I was concerned, that late autumn a few years ago, I was easily the luckiest closeted crossdressing and bisexual fetishist in the world. Ever since I was quite young, I'd had a secret desire for dressing up in sexy women's clothing, painting my lips up, and smoking long cigarettes while acting out intricate fantasies about spending passionate evenings with plenty of men; real, famous, or completely imagined. But when my first opportunity to step out and indulge in these passions for real first presented itself, it happened in an amazing way. You see, when I started a new job fresh out of college as a videographer for my local news station, I got an opportunity to actually meet one of the men who was pretty much in the "famous" category....a hotshot local reporter named Bruce Watkiss, who loved to wear his own hot leather jacket during his reports, and had inspired many of my fantasies for years.As my good luck would have it, we began get paired together often. So much that, eventually, he had invited me over to his house to play poker with "the guys". Only one other guy showed, and after he left early, things took a turn between Bruce and me, and I ended up sucking his cock on his black leather loveseat. We continued to be paired together at work, and a few weeks later, he asked me over to his house again...this time alone. I took that opportunity to bring up the idea of dressing up for him, and he was into it. We met up that early November night and I spent a wonderful evening with him, dressed up in my best leather outfit as I not only blew him again while dressed up, but we actually ended up having sex together, fulfilling another serious bucket-list fantasy of mine. Plus, we were still working together like normal, and it didn't make things at all awkward.So then one day, en route to a three-car accident scene involving an ambulance in Surprise, that he reached his hand out from the driver's seat and grabbed my knee. He told me that he had a friend who owned a nearby bar, and he was going to be doing the guy a favor and closing it for him, tomorrow night....and then he asked if I might be interested in a "change of scenery"? As in, would I be interested in driving somewhere late a night, meeting you in a closed bar, and obviously having sex, again? Um, where do I sign up? We spent the rest of our trip out to do the story and back formulating a plan to meet.The next night, I arrived outside of the bar at a nearby golf course at a little after midnight, at the time it was set to close. The main exterior lighting was out, affirming that it was, in fact, closed. I sat in the car for a moment looking through my backpack, which was full of my leather clothes, makeup, and cigarettes, then sighed in anticipation before opening the door and getting out. There was something rather surreal about that walk across the dark parking lot to the door; a feeling of exposure to the world pressed in on me, raising my anxiety to a quite uncomfortable level as I finally reached the locked front door and knocked on it with my keys, a signal we'd devised, the day before. I stood there waiting in angst, as if a thousand eyes were watching, and knew what was in my bag and what my intent was. Suddenly, there was a sound at the door, and I looked back at it.As I saw Bruce's face on the other side of the glass, smiling that hot grin of his, a strange feeling of relief washed over me and I found myself smiling back. An odd feeling of comfort, like I hadn't really felt before and seemed to raise as many questions at it did calm some other concerns. But as he finished fumbling with the lock and swung the door open, I got right back into the mood and wasted no time stepping in with him. The interior was a typically intimate little bar setting, not unlike expected; dimly lit, a few tables, a bar, a pool table, and a small dance area in front of a tiny stage. The smell of smoke lingered in the air from the evening's previous activities as Bruce poured me a shot of bourbon and I gulped it down. He then went into the office to finish some of the night's paperwork, and I stepped into the bathroom to dress up.I had brought the same black leather jacket, gloves, and miniskirt that I'd worn on our previous encounter, but this time I wanted to change it up a little. So I also had a pink satin blouse and a pair of sheer black pantyhose. I had shaved before leaving the house (legs, too) in excited anticipation of the experience to come. I so wished at that moment that I had a pair of sexy shoes or boots to wear, but my feet are kind of large, so finding them in my size wasn't easy, to begin with. As I slid the black leather motorcycle jacket over my shoulders and zipped it over the satin blouse, I rubbed my silky legs together and relished the feel of the pantyhose under my tight miniskirt while reaching for my lipstick. Sliding the red shaft over my lips over and over again until they felt sufficiently slickened up, I put the tube away in a jacket pocket and lit a long, white Virginia Slim in the mirror, breathing out a plume of smoke before turning around and reaching for the door....it was time to go hang out at the bar with one hot man!Turned out that Bruce hadn't quite finished up in the office, yet. I decided not to waste too much time, stopping only to pour another stiff shot of bourbon and grabbing him a beer before I walked over to the office door and slipped in. He looked up from the desk and smiled, then just sighed and closed the notebook he'd been writing in. As I walked over to the desk to hand him his beer, he stood up and walked around to my side of it and took it.Clinking our glasses, we both took a good drink, and sat our glasses down on the desk. He then reached out and pulled me into him, and I gasped in excitement as my own hard-on was shoved up against his, between his jeans and my miniskirt. But then he moved in and tried to kiss me, causing me to instantly draw back"What?" He asked."It's...." I stammered. "I'm just not into kissing, really. Just not - I'm sorry." I was suddenly worried I'd just killed the whole mood, maybe ruined the entire night's plans....but then he just grinned and squeezed my ass with his right hand."No worries," he smiled. "I'm sure we can do PLENTY of better things..."And with that, it was on, again. As I took a long drag from my cigarette and breathed a cloud of smoke at him, he stepped back and into the desk, and I dropped down to my knees in front of him. His belt and button were much easier to work with, this time, and it was not long at all before I held his fully-erect cock in one hand while reaching into my jacket for a condom with the other as I puffed away at the cigarette in my lips. Finally pulling my smoke away after one more drag, I dropped it in the ashtray and opened the slickened rubber before slowly using my gloved hands to roll it rather teasingly down his rigid, warm shaft. He squirmed some against the desk, and for the first time, I felt what I could only imagine a sexy woman in the same position goes through when she knows that she has her man's FULL attention. Finally reaching his well-trimmed pubic hair at the bottom with it, I pursed my slick lips together and winked and blew a kiss at him before going in.My lips slid luciously over his bulging tip, and I took him in just as far as I could on the first stroke; of course, which resulted in a rather embarrassing gag reflex. I pulled off and coughed, regaining my composure quickly and going right back in, noticing with a grin the ruby red ring of my lipstick around the base as I grabbed it with my gloved hand and immediately began stroking him as I concentrated on sucking the top half. I was again amazed at just how BIG he was; I honestly considered myself no slouch in the penis size department, but Bruce certainly had me beat by a good inch and some noticeable girth. I worked him with every ounce of passion that I could muster, sliding my tongue along the bottom of his shaft while my lip slid along the top, and he moaned softly while thrusting his hips good and slowly, working up a delicious rhythm with each saliva-slicked quaff that I made. I began to play with his near-hairless balls with one set on gloved fingers, while simultaneously stroking his shaft with the other set. One of his hands rested comfortably on the back of my head as I continued to suck him in earnest, but he didn't shove or push with it; just held it there, somewhat reassuringly. His thick cock filled my slick lips and mouth so comfortably, and I was relishing in the moment and just loving the full sexiness that I felt, dressed in black leather and sucking off for the third time a man I'd fantasized about for years."Okay, okay, wait..." he said, and backed off some into the desk as I slid my lips back from him and looked up questioningly. "Hold on, just give me a sec. Getting a little too hot, baby; and I'm not ready to finish just yet."I grinned, taking a moment to run my lipstick over my lips again before striking a match and lighting a new 120. As I exhaled the first cloud of smoke in his direction, Bruce got a wry grin of his own and moved toward me. His arms slid around me and he pulled me close, as we both stepped back into the open office doorway. He seemed to almost go to kiss me again, then turned at the last moment and buried his face instead into my neck, just above the collar of my jacket. I sucked long on the slick filter of my cigarette, relishing in the taste and feel of the smoke in my lungs as he slid a hand up my skirt while kissing and sucking at the bare skin of my neck and shoulder."What do you want, baby?" He asked."Oh, I want you to fuck me...." I breathed softly.We pivoted around, and this time, I found myself with my butt up against the desk and him in front of me. I slid up and onto the desk as his hands worked my miniskirt up around my waist. He then grabbed at the pantyhose covering my ass with both hands and tore them apart, exposing a wide hole around my waiting rectum. While he opened a tube of lube that he seemed to produce from nowhere, I took another drag from my cigarette and watched as he worked a palm-sized pat of the lube all over his rubber-covered shaft. After then simply dropping the tube to the floor, he moved in on me and wasted no time at all moving in.When Bruce had fucked my ass the first time, he had done me doggy-style from behind, and had moved rather slowly and deliberately, being careful with me, as he knew it was my first time. This time, we were in a much more missionary position on the desktop and I could tell he was much more excited and much more at ease, and he went right for the glory. The thick head of his cock shoved through my waiting anus with a slickened ease, and a sharp jolt of shocking pain, causing me to gasp as he continued sliding into me, all the way to the hilt on the first thrust. Right away he pulled back and thrust again, but this time wasn't as shocking. As he slid in another three, four, five times, uncomfort quickly faded and was replaced with that lustful feeling of just being so FILLED with him. I moaned and sucked on my cigarette as he fell into a rhythm that was much more to-the-point; much more FUCKING than it was being soft and careful like our first time.I kicked one leg up and over his shoulder as he continued fucking me into the bar manager's desk, and one of his hands grabbed at the collar of my jacket, unzipping it some and popping a button on my satin blouse. I didn't care; taking a final drag off of my cigarette and dropping it to the stone floor, I shoved back into him with each push. I began to heat up quickly in my leathers, and sweat formed soon after, which only seemed to heighten the experience for both of us. His cock drove into me, over and over with reckless abandon, causing me to cry out in delight and sheer lust. I was lost in the moment when suddenly I felt him shake a little bit, and he unexpectedly pulled back and out of me, shockingly pulling me back into reality.Before I could question anything, however, I saw him yank the condom off. With a quick stroke or two of his now bare cock, he suddenly gasped, and a load of thick, white cum burst from his head and splashed across the front of my jacket. He continued to stroke, and another shot blew across my leather sleeve, before another landed on the miniskirt bunched around my waist. I found myself losing the battle to hold out, and as yet another jet of white cum splashed across my jacket, burst into an orgasm myself. He worked a leg in between my own and rubbed his thigh against my own cock as I lost my own load all over the desk and my pantyhose. He then pulled me into him and held me close as we both did our best to hold onto the bliss of our near-mutual climax. If he'd have told me he wanted to cum all over me before we'd started, I might not have been too thrilled with the idea; but laying across the desk beneath him and covered in loads of it from both of us, I felt a reassuring DIRTINESS that I found myself rather intrigued with. As he finally stood up and I slid a new cigarette between my lips, I could only think of asking him one thing..."What are we going to do to top THIS?"