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.

"ITOLD 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?