The Leatheress 102 – “The Full Monty”

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The Leatheress 102 – “The Full Monty””The Leatheress” – Episode 102″The Full Monty”Growing up, I had always been secretly in love with dressing up in women’s clothes; the rule always was, the shinier and softer, the better. In my more formative years, this began with satin nighties and underwear that I’d “borrowed” from the female members of my household, but my lust was always most reserved for leather. Oh, how I used to search out and spend intimate hours with any pics of sexy women in leather that I could find. So naturally when I moved out of home, and had a little more privacy, I wanted to get myself a little collection of leather of my own. It was slow to start, but I’d managed to gather myself a black leather motorcycle jacket, a tight, black leather miniskirt, and a delicious pair of matching gloves to make up my first outfit. I loved it, SO much…it was my soft, leather escape from the world.As I explored this fetish growing up, it led to a few more of them. First, I discovered lipstick…oh, how I love my lipstick. It is just the epitome of femininity; nothing makes me feel more like a sexy woman than having my lips smeared with lipstick. The redder, the better. But the fascination with my lips also led me to get into smoking while I dressed up, or even if I was just doing my lips to jerk off. I love a sexy woman who smokes…the way it swirls around her, the smell of it intruding into everything, the ring of lipstick on the filter. It just turns me on like nothing else. And a sexy woman with slick lips, smoking AND in leather…? THAT was what did it, for me. So much so that it was also what I began to WANT to be; to experience everything it had to offer. And THAT is where men began to come in. I began to fantasize about being a leathered up slut with slick lips, puffing sexily on cigarettes while a man had his way with me. But I was never JUST into guys…I had a certain “type” to be sure. On that list included guys like David Hasselhoff, Burt Reynolds, and this hotshot local news reporter named Bruce Watkiss. He was an every day appearance to me; always something new and often involving the sexy black leather jacket that he loved to wear on-air.The thing about Bruce was, I actually KNEW Bruce. Or eventually came to know him. After years of watching him on the news and fantasizing about him, through life’s turn of events I eventually came to work at the same news station as he, as a videographer. And as luck would have it, we started getting paired up a lot and got to know each other pretty well. So well in fact, that he invited myself and a few other guys over one night to play poker while his wife was out of town. The one other guy who showed that night left early, and as the night went on for Bruce and I (like I was going to leave before I had to?), one thing led to another and I ended up blowing him on his black leather sofa. Even though I didn’t get to dress up like in my fantasies, it was a wonderful experience, and sure didn’t do anything to HELP my desire for the man…it made it worse. I didn’t want to come right out and ASK him to let me blow him again, but as luck would have it, I didn’t HAVE to.One day when we were driving together to a car crash in Avondale, he just came right out and asked; “So, Sadie (his wife) is going out of town again, Friday…you, uh, want to come play some poker?””Ted and the guys too?” I asked.”Oh, Ted was a lightweight pussy, last time; I say we just keep it a more…private game.””Private, huh?” I remember winking at him. “Like as in, higher stakes?”He smiled. “You bet.”We got to talk about it a little more on the way home, but it was a long drive out and back, and so I ultimately ended up asking him if he’d have a problem with me “dressing up” for him. After informing him of what “dressing up” would entail, he was rather well interested…possibly even a little enthused. We decided that would be our Friday together…I’d come by, dress up in my best outfit, and we’d let the night take us where it would. Needless to say, since it was only Wednesday, I spent the next two nights dressing up and fantasizing about what was planned to come. Then, it finally did…and lara escort oh, what a night it turned out to be!I arrived shortly after dark, around 7:30 or so, dressed in my normal wear with my clothes and lipstick packed away in a tote bag. I remember thinking while walking in, this one was possibly going to be quite an experience; the bar area was more dimly lit than it had been during our first encounter, soft music was playing on the stereo, the smell of the cigar that he’d recently been puffing on was lingering in the air, and he had a bottle of whiskey on the coffee table next to his black leather loveseat ready for us. Shortly after I got there, we had a couple of shots to start the night and after a little obvious flirting with him, I excused myself to go and dress up.I remember that, besides being rather buzzed from the whiskey we’d drank, I was also almost overcome with anxiety more than once at that point. Was he going to be as cool with this as he’d thought? What if I was so badly un-passable that he’d just giggle and decide it was time for me to go? I ended up taking a good half hour in that bathroom, first getting fully undressed, then sliding into each piece of my hot leather outfit, one at a time. First, the miniskirt. Sliding it over the soft, silky legs that I had shaved the night before in anticipation, I got a raging hard-on and had to take a few moments to relax. I then went ahead and tugged on my leather gloves, their tight softness sheathing my hands in sexiness. Relishing in the sight of it in the mirror, I then used them to apply a thick coat of the deepest red lipstick that I owned and lit a cigarette before finally sliding my black leather motorcycle jacket over my shoulders and zipping it up. There I was; dressed up in the hottest woman’s outfit that I own, about to walk out the bathroom door and at the very least, suck Bruce’s cock again. I took another drag off of my cigarette, then dropped it in the toilet. After taking a deep breath, I opened the door and shut the lights off.Right away, I could tell he’d gotten things even more ready. Down the hallway I could tell that the bar area was even MORE dimly lit, and the music had been changed to a softer, sexier sound that included more saxophone and piano than guitar and drums. As I came to the open bar door, I could smell that he’d re-lit his cigar, which just helped to beckon me forward and into his lair. I stepped around the corner and brought us into each others’ view, and he looked up at me as we both took each other in for a moment. I remember the anxiety building quickly again as I looked at him sitting their on the black leather loveseat where I’d sucked his cock just a month or so before, his arms stretched out across the back with his cigar burning in one hand; but before I had a chance to collapse from the building worry, he tossed me a smile and a grin that set me to ease as he slowly stood.”I like…” he said, “come here.”I walked the ten or so steps over to him for what felt like an eternity; everything slow motion, like a movie. The soft feeling of the satiny lining of my jacket rubbed against my bare torso below as my tight miniskirt rubbed my cock with each step, slowly building an almost uncontrollable hard-on of my own as I did. I stepped up to him in the dark, smoky room and he handed me another shot of whiskey…we both tossed them back and put the glasses down, then he moved close and took me in his arms. He ran his hands down the back of my jacket to the tight leather covering my ass, while simultaneously moving in slowly from the front and rubbing his obviously hard bulge into my thigh. His hands squeezed my butt cheeks through the miniskirt as he pulled me in close for a moment where I was worried for a moment that he might try to kiss me…and I wasn’t ready to go there, yet.”Come here…” He said again, leading me by the leather-gloved hand as he stepped backward to the couch and sank back down into the middle of it. I took a moment to reach into the pocket of my jacket and grab the pack of Virginia Slims 120’s that I’d bought just for this experience, and after sliding one of the long, white cigarettes out, stuck escort lara it between lips so slick from lipstick that I almost thought that it was about to slip out and lit it as sexily as I could imagine before dropping down to my knees in front of him on the sofa. While he puffed away on his cigar, I stuck the cigarette in my lips and began fumbling with his belt, button and after what seemed like a protracted three-front WAR, finally got his zipper down. Taking another long drag from my own cigarette with my left hand and relishing in the feel of the leather glove on my freshly-shaven face, I made eye contact with him as I slipped my other glove under his underwear band and found his already-stiff cock with it.As he made a soft moaning sound, I struggled with his bulging member before finally withdrawing it from his pants. As it bobbed before me in all it’s veiny glory, I grabbed a condom from the nearby table and opened it, then slowly and salaciously used my gloves to slide it down his rod to the well-trimmed hair at it’s base. He put the cigar to his mouth and puffed again with a satisfied grin on his face, and as I took another long drag off of my cigarette, I felt fully free to just let go and enjoy the moment.And enjoy it, I did.Opening wide, I slid my lipstick-slickened lips across the bulbous tip while breathing out a cloud of smoke, and slid my way down the lubricant-greasy latex as far as possible, until his tip tickled my tonsils and made me gag. With a cough and a blast of saliva, I pulled back off of him and struggled to regain composure.”It’s alright,” he said softly, “take your time…we’ve got plenty of it.”This charged me back up, right away. I grabbed his pole with one hand, and shortly after dragging again with the other, dropped the cigarette in the ashtray and promptly took him into my mouth again. I slid as far down as possible on him, but was careful this time to avoid the spot that had caught me the first time. Sliding back up until I reached the tip, I sucked my way back down and began to work on forming a rhythm. He worked with me beautifully, finding my rhythm quickly and he slowly and softly bucked his hips up of of the couch, perfectly filling my mouth with every stroke. Saliva built up, and this led to my pace doing so, as well. I sucked his smooth shaft with earnest, reveling in the way it filled my mouth so perfectly, and also being mindful of my teeth while doing so. As I sucked him stroke after stroke, I discovered something that he really seemed to like; when I sucked him into my mouth, I would work my tongue around the bottom of him in a sort of “massaging” way which not only seemed to please him but also charged me up, as well. I was in heaven; here I was, on my knees before this man I’d fantasized about having sex with for years now, dressed in black leather and lipstick and sucking his swollen cock. I truly felt more feminine than I ever had before, and was loving every second of it.When he actually asked, I didn’t quit hear him right, and had to stop sucking him long enough to ask him to repeat himself.”Do you want me to fuck you?” He asked again.Well, this was really going to change everything, wasn’t it? But kneeling before him in my tight black leathers, with my lips and his cock smeared with red lipstick, I couldn’t think of anything that I wanted more at that moment. Stroking his spit-covered member with one gloved hand, I muttered the answer that would change everything.”Give me your best, cowboy.” I said with a wink. Smiling that sly grin again, he began to get up as did I. He moved around behind me, his hand rubbing the front of my chest through my jacket, as if I had tits to play with. I bent over to grab my cigarettes off of the floor, almost stumbling as I felt his stiff cock press into the leather of my skirt and into the crease of my ass cheeks. As I fumbled with getting a new cigarette out and into my gloved fingers, he grabbed and popped open a tube of K-Y lube that had been sitting on the table. While I slipped a fresh cigarette into my lips and lit it, he slid his hands over my skirt and pushed it up over my ass…the feeling of the soft miniskirt sliding lara escort bayan over my smooth skin and having my ass open and exposed to him was filling me with electricity I’d never felt before. I reached down and slid my own cock into the skirt around my waist doing my best to store it out of view in preparation for what he was about to do to me. While I took another long drag from my cigarette, he squirted some of the lube into his hand and worked it over his throbbing cock.”Are you sure?” He asked me.”Oh, Bruce…” I literally moaned like a sex-starved cock queen. “Give it to me, baby.”He reached out with the lube and squeezed, and a deliciously slick blob of it landed square between my ass cheeks, sliding between them as the greasy head of his cock pressed against me while I stood prone and spread-legged before him over the couch. I shuddered, dragging off of my cigarette in lust as he shoved for the first time. Delightful as he felt pressing against my back door, he didn’t enter me on the first time. It wasn’t the second or third, either. In fact, it took him about six of seven shoves against my overly-sensitive backdoor before he finally popped the head in.I was in mid-drag on my cigarette, when it happened, and it stopped me cold. As the tip of his swollen cock popped into my tight anus, pain took over lust. Suddenly, everything seemed to hurt; my entire body was lit up from it, and I had to struggle to keep from dropping my cigarette in shock. He reached around both hands in front of me, softly pulling me back into him and telling me calmingly and assuringly to relax and wait it out…he assured me it would be just fine. I almost asked him to stop, it hurt so bad. But I also knew from personal experience fucking myself for years with everything from candles to other devices much larger that he was probably right. I stood prone below him with my knees on the front of the loveseat his face over my shoulder and my own in the soft leather cushions in front of me, and he softly moved his hands over the back of my jacket and shoved again slowly, bringing another sharp blast of pain.But as he slowly began to shove again and again, obviously being as tender as possible, the pain quickly began to fade. And it began to be replaced by the feeling I’d known for a while, but never quite for REAL. As Bruce began to work up to his own rhythm, the feeling of being just so FULL of him took over me. I sucked on my cigarette as I began to buck back against his thrusts, timing it to push against him each time as he pushed into my electrified rectum, lost in a feminine lust I still cannot quite explain. It just felt SO much better than fucking myself with tools EVER could have; it was literally everything I could have imagined and SO much more. He could have fucked me forever, for all I cared at that moment. I bucked back against him with an eagerness I’d never felt before, feeling nothing short of SEXY as he fucked me across the front of his leather sofa.It was quite obvious, when he came; and happened a little quickly for my taste at that moment. I had just it another cigarette and was breathing out a cloud of smoke when he began to stammer some in his moans, and the angle of his shaft slipping into my asshole changed. His hands squeezed my hips, and he shoved into me in earnest, filling me almost painfully with every inch of himself. Even though he was wearing a rubber, I swear that I could feel it, blasting into me with each heavy thrust. I relished in the sexy feeling for a moment, and his bucking shoves worked down into a soft sliding again, his breath hot against my ear as he struggled to catch it again.”Oh, oh God YES…” he murmured, then without warning he slid out of me, leaving me suddenly feeling so EMPTY. But he was finished; that much was sure. No use complaining, I thought…I’d gotten what I wanted out of this. I slowly sucked another drag off my Virginia Slim, softly breathing out smoke as he dropped onto the couch beside me and I slid in beside him, softly rubbing his quickly-softening and satisfied cock with my glove as we both enjoyed the afterglow together for a few moments. After finishing my cigarette, I got up and went back to the bathroom, re-dressing before it was time to head home. But before I did, he said the one thing to me that made the whole night even THAT much more better….”We have GOT to do this again….”

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