1 comments/ 29880 views/ 1 favorites Pushing the Envelope By: THISISTHEAGE I wasn't sure why I was about to enter the club. Actually, that's a lie. I knew why I was there. Why I was standing at the entrance of the "weird" club under the bridge nestled among the run-down warehouses, homeless people and street-walkers. It's just, well, it's just that I had an affinity to the music, the people and the setting. It wasn't so much that I got off doing something I wasn't supposed to do. It's more than I was doing what always got me the most excited, the most revved up. Circumstances and a quality upbringing just took me another route from those typically residing in such places. VP's of Fortune 250 companies aren't supposed to hang out at places like this. They are supposed to dine at fine restaurants, relax listening to jazz or chamber music and make themselves comfortable in a country club setting. I always find those settings to be a bit pretentious and superficial. It's not that I can't integrate myself into those settings. Hell, one almost has to to succeed in business. I just know I don't really need to immerse myself among groups of people trying to live a lifestyle they can't afford or one that helped them compensate for their lack of self-worth. At the heart of it, I am a bit of a loner, with the ability to morph myself into the role needed to succeed. Clubs like these…didn't need that flexibility. I entered the club. And, as hard I might try, I knew I didn't quite fit in. Of course, these people are less judgmental, but they didn't arrive in a M5, wearing an Armani shirt, Lucky Jeans, sporting a Tag watch and Allan Edmonds shoes. Oh well, there are benefits to success. Nine Inch nails pulsed in the background. No dance mixes here, just beats that hit you right in the gut. Cigarette and Reefer smoke filled my nostrils. The blue and red giving the club light required a pupil adjustment. I had the time; I was going to be there all night. I began to find my way to the bar on the far left of the club. Of course, along the way there were the requisite colored rooms. At least they weren't VIP rooms filled with wannabes. The Red Room with it is shaggy couch and walls contained several leather-clad Mistresses with female and male subs on leashes. The blue room with its retro furniture housed the early 20's group of silicone-filled girls and drunk boys who were too scared to explore the club but needed to feel of excitement of a "dirty" night out. I didn't feel compelled to explore the secluded rooms lit only by candles and filled with lots of exposed skin. My spot at the end of the bar provided me with a great view of the dance floor and entrance. I settled in and watched the Amazon bartender walks toward me. She wore tight jeans, a black wife-beater cut off just below her enormous chest and black cowboy boots. A bra wasn't needed on her 38DD chest. The tattoo around her belly button just didn't do it for me, but she certainly was someone both men and women would notice and fantasize about. She didn't even ask me for a drink, she just looked at me. I ordered a Bombay Sapphire and Tonic and watched her walk away from me. "I bet she could wear someone out," I thought to myself. With drink in hand, I watched the crowd. For some reason, my eyes glanced over to the entrance as the most stunning woman I'd ever seen walked in. She stood maybe 5'9", just a bit shorter than my 6'1" frame. Her brown suede skirt was zipped tight against her lower body but not so tight I couldn't get a glimpse of her stockings and garter through the front and back slits in her skirt when she walked. Her calf-high boots were a special fetish for me. Her ass sat high atop her gloriously long legs. I could witness the firmness of her ass through the snug fitting fabric of her skirt. Her black blouse allowed one to see-through to an Aubade demi bra. The fullness of her breasts was clearly visible. Her lips covered with black provided no protection for what I was sure were legendary oral skills. Her nails, like her lipstick, were black. Her brunette mane fell to the top of her ass. The choker she wore completed her outfit. This was the woman I long had fascinated about during my many travels. She exercised at my health club and was the manager of the Starbucks on my way to work. Her nametag read Samantha. I'd never really talked to her, but had long pleasured myself to the thought of orally worshipping her wetness. I guessed her age closer to late 30's than to my 34 years. She reeked of sex. No woman should be able to look that hot. I never even talked to her, and she owned me. I watched her follow the same path I had taken only 45 minutes earlier. She finally found her way to the bar. I was amazed someone so stunning arrived alone. Women of her beauty aren't supposed to go anywhere solo. She ordered a Shiraz. "Yes," I spoke to myself, "A women after my own heart." It was obvious from the Amazon's not so casual hand-touching and the way she asked my desire to repeat her drink order that I wasn't the only one captivated by this regal woman. I did my best to catch her attention. It really is kind of amazing. No matter how successful a man may become, a beautiful woman always has the upper hand. I suppose the blatant staring wasn't the best approach, but damn she was beautiful. If she had any idea how many times I had fallen asleep thinking about her she would understand my trance. She didn't dance nor talk to anyone; she watched the crowd much like myself. After another drink, I decided it was time to approach this vision of so many, shall we say, explosive thoughts. "Hello." She gave me a quick glance and resumed her crowd watching. "Hello," I said again. This time she didn't even look. In fact, she looked away. "Son-of-a-Bitch," I thought to myself. I finally get up the nerve to talk to this creature and she wants nothing to do with me. I stood for a second, stared at her profile and watched her place her drink on the bar and find her way to the bathroom. I thought about following her, but it was evident she didn't want me around. I turned around to go back to my spot at the bar. There was a drink waiting for me. The Amazon was smirking at me. "Bitch," I said under my breath. I slowly finished this, my last drink and made my way to the bar. Despite the smirk, I gave the Amazon a quality tip. I made my way to the exit still hurting from the search for the woman of my dreams. I felt a firm grip on my right hand. I stopped and turned only to find my dream staring in my eyes. "Are you leaving?" she purred. Her smell intoxicated me. Her eyes seduced me. I couldn't believe the depth of green in her eyes. "How in the world is this woman so unbelievably attractive?" I questioned myself. "The surroundings aren't too receptive tonight." "I would have expected more from you. The night is young." "I'd thought I'd change my venue." I responded. "I think you should stay," she spoke in my ear while rubbing her breast against my chest. Her breath lingered just a bit in my ear. The fingers of her left hand playfully tickled my neck. I could feel her nipple against my pectoral. I am sure she could feel the beginning of my arousal. I pulled away from her just a bit to scan her body language. She gripped my hand even harder and pulled me to the dance floor. Chemical Brothers showered down on us as we began to dance. It was hard to move among the throng of people, but it only gave me the opportunity to pull her even closer. I fully expected her to challenge me, but she seemed almost comfortable pressed against my athletic frame. She definitely knew how to move her long, sexy body. She worked her right leg between mine and pulled herself even closer to me. Her toned arms alternated between gripping the back of my head and raising them above her head. Her belly piercing, not to mention her flat, defined abs, was visible when she raised her arms. My arousal had grown to its full potential. I stared at her body with lust. I longed to kiss her gothic lips, to make love to them, to fell them pressed against mine as my tongue snaked its way inside her mouth. Finally, I pulled her close to me. Her nipples were clearly visible through both bra and shirt. She gave me a quick glance and leaned forward to kiss me. My dream…my passion…I was finally kissing her. The fact that I didn't cum right there still escapes me. She outlined my lips with her tongue before playfully biting my lower lip. And then I could feel her tongue inside my mouth. Our tongues danced together and then took turns exploring each other's mouths. It was like no kiss I had known before. So many months of dreaming, hoping and then it finally happened. I was weak in the knees. There was no way should could not feel the passion I had for her. My arousal had grown to uncomfortable levels. I could feel her smile at my plight as she kissed me. I worked my down to her neck only to hear her moan in my ear. Her nipples became even harder, and I lowered my left hand to run my palm against the skin of her upper chest. "I'm soaking wet," she whispered as she moved her tongue around my outer ear. "I've thought about this for months," I admitted. Slowly she turned herself around and positioned her ass against my cock. She leaned against my chest and put her hands behind her back. I glanced over the dance floor and found no one but one of the young 20 something hotties in the blue room watching us. I gave her a crooked smile as she watched in amazement. Samantha found her way to my fly and unbuttoned my pants. The relief I so desperately needed was available. My cock sprung through the fly of my boxers. Samantha did nothing to help my problem. Her hand gripped my erection while she smiled at me with her head tilting against me chest. Our "fan" watched without complete fascination. To my amazement, Samantha squatted down just a few inches until my cock was positioned underneath her skirt. I could feel the warmth of her thighs against my arousal. Her legs were wet with her own moisture. She bent forward slightly until my cock had found its way through her thighs against the vision of so many of my dreams. She gave me a quick glance over her should and pushed against me. I entered her quickly. I could feel her wetness surrounding my cock. I heard her moan as my head pushed farther and farther into her. We continued to dance slowly with my member inside her. I kissed the back of her neck while my fingers traced the outline of her nipples through her shirt. I felt her grow wetter as my cock pulsed several streams of cum. She moaned even louder as my orgasm splashed against her g-spot. We continued to dance as my cock withdrew to its normal length. I could feel my cum on the inside of her thighs. Samantha put her hand inside her skirt, dipper her finger into her wetness and licked if off her forefinger in front of me. Samantha leaned forward and kissed me, put my cock back in my pants and slowly buttoned my jeans. She then grabbed my hand and pulled me to the exit. After two steps, she stopped, looked at our observer and gave her a come-her motion. Our visitor grabbed Samantha's hand and joined me in our pursuit of the most stunning creature. Pushing The Envelope Where do I start something like this, right from the beginning or lead up to it with a description? I suppose I'll give you some background. My name is Daniel. For the most part I'm a happy-go-lucky kinda guy. My wife and I have a pretty healthy relationship. I enjoy her company and we get along really well when we're not individually stressing about work or the kids. We deal with things differently, which makes sense because of how different we are. My wife is a wonderful beautiful person. The kind of person authors and movie directors make you fall in love with with their work. A beautiful brunette, though she dyes it to have a strong, deep red glow. She's a little taller than most average woman, but not so much that it becomes off-putting with the deepest brown eyes you've ever seen. I like to think about her eyes as personifying her deep love and devotion. She's slightly larger than your average woman and it messes with her head. She always covers herself when she changes clothes with me in the room even though I've seen her naked for the past decade. Her lack of self confidence is a little disturbing to me, given how wonderful she really is. She's kind and gentle, always worrying about other's feelings and keeping herself in check. A modest woman, she's a hard worker and an honest soul. She simply lacks passion for many things. This is something I have in abundance. I am a gruff guy, kinda rough around the edges. My sandy-blonde hair shows both in both my hair AND my facial hair, which is a bit irritating. It sometimes looks like it's patchy because you can't always make out the blonde hairs on my face. I can be a bit lazy at times, which kind of explains why I have a short haired beard I'm always sporting around. My wife always tells me she loves my eyes though, because they have different colors mixed in and show at different distances from the pupil. A darker emerald green outer ring gives way to a brown interior. I'm also a little heavier than average, but my althetic type body helps conceal it very well. This doesn't really bug me, I've been this way my entire life. On the opposite side of my wife, I'm a tough but fair kinda guy. I don't place too much importance on people's "feelings", or atleast thats what I tell people who know me. It's not that I don't care, it's just that no one ever really showed me how to be careful when dealing with others to not hurt them emotionally. I grew up without a mother, and my dad is a country boy. His main area of focus was morales with a highlight on honesty. He always admired clever people, loving it when someone would come up with a new, more efficient way of doing something others failed to think of. I grew up aspiring to be the kind of person my dad would admire, but alot got left out emotionally. This difference has lead to rocky but steady relationship. Lately we've had some troubles with intimacy. I've been laid off for awhile from my factory job. It didn't bother me much, I was actually kind of relieved when it happened. The life of a factory worker is stressful as much as it can be intense. Long hours, low pay (unless your a supervisor), and NO appreciation.When they let many of us go, I switched my attention to finishing my associate's degree. My wife agreed to take a part time job, which should help us make do when combined with the little unemployment payments I get. Ever since then, we don't have sex much. We've never set records for amount anyways, but with her being tired from work it's driven her low sex drive even lower (did I mention her low self-esteem?). I've always worked tirelessly to try and find a way to increase her sexual desire through experimentation, but hardly ever do I find something that really drives her wild. Many things she likes in small doses spread out so that they don't get boring for her, like when I'm strumming her clit and slowly slid a finger down from her V spot to her backside. I tryed doing this multiple times, but she always wiggled and swatted me away and I got nowhere until I got her drunk. She's always more honest and open to new ideas when she has a buzz going. Having me play with her until she orgasims once, then going missionary for the big finally is kind of our thing. She payed no extra attention once night after we'd been having some drinks and we started our ritual upstairs. She allows herself to enjoy sex much more when intoxicated, so she moaned a little louder than normal when I sat next to her naked body and spread her with two fingers. Not to my suprise, she was wet already. I trailed her juices from her opening up over her clit and back down again, using my fingers to transfer her moisture to the clit. This always had a profound effect on her. Once she was wet enough from my fingers to slide across rather than rub her clit, she did her usual bucking around in delight. With this, I did the same thing I always do, and slide down to hug one of her thighs and rest my head on it while I slide my arm under her leg and finger her from under rather than over. This time I started something a little different. I made large sweeping strokes from top to bottom. I hit the climax of her parts and wiggle my finger on the top of her clit like I was ringing a small bell, then slowly drop all the way down to the opening of her pussy. I did this from time to time, though it had been awhile so she immediately noticed it was different. She made no protest however and I continued for 10 minutes or so. I knew she would begin to get impatient, one of my wife's very few character flaws along with being stubborn. Her ferver always gained alot of momentum if I would drag it out by going slowly. She was wet....VERY wet, something I had planned. You see, she would instantly become suspicious if I reached for the little KY bottle we bought years before. She tryed anal with me before, but refused to let me do it my way. I wanted her to enjoy it, after all if she didn't then I knew I probably wouldn't get a second chance at it. She just wanted it over with so she forced me to go fast and it obviously hurt. I continued to spread her moisture around, making my way up to the top and ringing the bell to keep her interested while I kept moving the lubricant further south. It happened so gradually that she hadn't noticed I wasn't even on her pussy anymore, rather the no man's land between back and front when i hit the southern pinnacle that was rapidly advancing. Her breathing was getting faster during the downstroke, she had to have known where this was going but she continued her lack of acknowledgement towards my actions and just enjoyed the ride. The booze were definately doing their job. Slowly I started to feel the terrain of her skin between her pussy and the back button sloping more sharply down and I knew I was getting close to the grand prize. This was the farthest I'd gotten before her fears and insecurities pushed me off. I was getting nervous, I REALLY wanted to add this extra angle to our love life. I mean, how awesome would it be if I could start to experiment on her with the plugs while we did it. That basically would double the amount of positions we had in my mind because each would be different if she had a plug in her ass while doing it. I had to make this transition as smooth as possible. I couldn't just go for gold, even if I had taken this much time already to get her ready. This would require more finess. Slowly, one stroke then two strokes I found myself stopping right on the ridge of her back hole, afraid to make contact. Finally I decided I had to cross the threshold. I increased the length of the next stroke by a presumable inch or so, essentially passing over it, letting my finger graze the hole. "Ahhhh...", a slight gasp escaped her throat. She enjoyed it! I knew she would, I just freakin knew it. If there was any doubt in my mind about what she would think or if she would like it, it vanished right then and there. I gained alot of confidence from her small, almost indistinguishable outburst and continued to graze her over and over letting the moisture settle and reduce the friction on her hole. Now I will have one last threshold to cross, uncharted territory. This could make or break my case and now more than ever I had to proceed with caution. Bide my time until it was just right, but how would I even know when to make the push? Luckily for me, the signs were a little easier to read than I would have expected. With every brush of my finger over her little button, her breathing increased in speed and strength. She was getting close. I knew I'd hear her typical moan pattern she always did. It always reminded me of the old baseball announcer sound clip when he yells over the radio, "going!!......going!!!......GONE!!!" in which his voice gained pitch and volume over those three famous words. The only difference was she only used one sound. The same moan for each pitch and volume stretched out over a 6 second period. An idea came in my head. I'd listen for the moans and on the count of two, thrust in with one steady push. The game was set. Gaining in momentum, she slowly started to arch her back and grab the sheets. "ahhhh..." she moaned. Here it came.... "AHHHH...." louder than before. Do or die time... I rested my fingertip on the rim, slowly adding pressure to it until it started to make way. It was suprisingly easier than I expected, I must have dragged this on quite a while. Within the matter of a second I had the fingertip halfway in past the fingernail. "baby?!?!", she half yelled in confusion and suprise. She was trying to sound angry but she and I could both tell her heart wasn't into it. She enjoyed this, and I knew I would be doing this again even though we hadn't fully commited yet. "Here goes nothing" I thought to myself as I gave the command to my hand to start pushing. The finger slowly started to disappear into her rectum. I didn't stop until I couldn't push any further. Mid-way between the first and second knuckle she arched fully back and lifted her butt off of the bed completely letting the final rallying cry escape... "AHHHH!!!" she cryed out as she seemingly was hit by lightning. Her body convulsed and shook violently, thrashing about so hard that some of the pillows she was using were thrown from the bed. The initial orgasmic shock subsided and she was able to once again make contact with the bed with more than just her shoulders and feet. The reality that she had a finger in her ass took a few seconds to hit her brain, but was soon in full realization and she rapidly ushered me out of her. "I TOLD you." I snickered. I knew I had that same devilish grin I always had on when I made a point pretty clear to someone who opposed me. She didn't respond, she COULDN'T respond. she was completely spent. It was as if she placed all her sexual energy into one blast of pleasure. "So now will you admit you like it in your ass?" I asked, somehow unrealistically expecting her to drop her defenses and come to the "dark side" as she called it. With that she covered her face in embarassment. "UGGGG" she let out in slight frustration. This time I could tell she was only frustrated because she had been wrong. She staired at the ceiling for a few moments, apparently zoning out before realizing that I was still waiting for an answer. "NO!!" she yelled with only half the vigor she'd have had if she were serious. She covered her face again and slightly laughed to herself. Did I mention she was stubborn?