Jills Older Sister

If there is anything better than leaving work early on a sunny Friday afternoon in July, maybe it's knowing that you have the house to yourself for the whole weekend. These precious few days had been marked on my calendar for over a month now. Not any calendar at home of course. Jill, my wife, would have had a bird if she ever caught me looking forward to anything that actually brought me a little joy. Why? Because my beloved spouse of 14 years is a vindictive, hypersensitive, control freak who has dedicated her married life to denying me even the smallest of pleasures. But then what the hell, I didn't need to dwell on the pitiful state of my marriage right now. Jill and our daughter were gone till Sunday and for the next 48 hours my time belonged only to me.

I parked my car out on the street and sprinted up the stairs through my front door. Normally this was taboo as Jill insisted that I park in the alley that runs behind our house and use back door. She claimed that too many coming and goings at the front of the house was a clear indication that the inhabitants were decidedly "lower-middle-class". I then proceeded to commit a whole series of divorce worthy offenses: leaving my shoes in the hallway, my suit in a heap on the bedroom floor and not thoroughly bleaching down the bathroom after a particularly satisfying piss. The weekend had barely begun and I was already having a ball.

I rooted out my grubbiest T-shirt and most faded shorts and slipped them on. The only thing left on my agenda was to make myself a sandwich, grab a cold bottle of Bud and make my way out to the pool in our backyard. Passing by Jill's exquisitely fussy and over-decorated bedroom (yes, we slept in separate rooms), I briefly considered going in and having a little fun. Nothing upsets Jill more than someone messing with her ridiculous army of little glass knick-knacks. But I quickly thought better of it. If Jill ever concluded I was responsible for disturbing her carefully ordered room, the likely punishment was a lengthy withdrawal of sex. Not that we did it that often to begin with. But the last thing I needed was to have sex even more infrequently.

Things weren't always like this between my wife and I. Sure, Jill has always been somewhat of a control freak. But the cute little dirty blonde dynamo I met in college at least used to enjoy sex. Then, like today, she knew what she wanted and had no compunction about going out and getting it. We first met up on one of those university ski-trips. If you're unfamiliar with these college standbys, the formula goes something like this: get a busload of horny college kids, jam them into as few condo's as possible, add copious amounts of vodka and beer then sit back and let nature run her course. Jill didn't know me, but I knew her - everyone knew Jill whether they wanted to or not. She was one of the organizers of the trip and spent most of the weekend compulsively ensuring everyone was having a good time.

You could say that I ended up as one of her "special projects". What can I say? I'm not that good in social situations. By nature I'm pretty quiet and keep to myself most of the time. I know that my demeanor can put people off; they confuse my shyness with aloofness. But nothing could be further from the truth. I really didn't want anyone looking after me, but Jill wasn't the kind to take no for an answer. For two solid days she fluttered around introducing me to women. All for naught, though. Experience had taught me that I would never talk a woman into bed. It had taken me two months just to get up the nerve to ask a girl in my Spanish class out on a date. But despite my obvious ineptitude with the opposite sex, Jill doggedly pressed on.

When I look back at what happened next I really can't help but laugh. Some might characterize what she did next as a charity fuck. But anybody who says that doesn't know my wife very well. Jill isn't one for charity, but she sure is a hellcat when it comes to getting her own way. She somehow took my inability to get laid as a failure on her part. And since Jill doesn't accept failure all that well, it was up to her to put things right. On the last night of the trip I decided to slip away from the increasingly rambunctious party and make my way back to my assigned bedroom. By this time I was exhausted by Jill's constant attention and figured I would let both of us off the hook for at least one evening. I was on the floor in my sleeping bag, just about to nod off, when I heard someone enter the room. I could barely make out the figure of Jill slipping in and quietly closing the door behind her. At first I figured she was here to ball me out. So I quickly offered up a lame excuse to keep her happy:

"Jill, I appreciate everything you're doing for me, but I think I picked up some kind of bug. What do you say we take the night off and let me get some sleep?"

She whispered back: "Don't be so stupid. We both know what a lost cause you are. Now just shut up and enjoy."

With that Jill leaned over and locked the door. She moved over in front of the window and was instantly and gloriously silhouetted against the moonlight streaming into the room. She pulled off her fashionable ski sweater and kicked off her jeans. Resplendent in a matching pair of white panties and tank top, she looked ravishing. Though Jill is quite petite, just over 5 feet tall, there is nothing petite about her curves. Her breasts, though small by most standards, actually look plump and full when contrasted against her teenager-like frame. Through the thin cotton of the t-shirt material I could discern her nipples becoming erect. She was possessed enough not to rush the moment, giving me ample time to devour her with my eyes as the reality of what was happening began to make itself known to my hardening cock. As she wiggled out of the tank top, she fixed her eyes upon me and the corners of her mouth curled up into a shy grin:

"Are you enjoying yourself Stuart? Maybe you want to strip down as well and unzip your sleeping bag."

Wordlessly I complied, kicking off my shorts and letting my very erect dick spring free. Jill continued undressing by slowly relieving herself of those sheer panties - the dark triangle between her legs now drawing all my attention. She tiptoed over to my prone body as I opened up my sleeping bag for her. She crawled in and stretched out next to me as I felt her lithe body make contact against my bare skin. I moaned a little and gave an involuntary shudder. Jill proceeded to slowly rub herself against me. Her naturally firm breasts were pushed up against my chest. She then proceeded to drag her tits down the length of my torso until they came to a tantalizing rest at my groin before making her way back up my body. The sensation was incredible and she kept this up until I thought I was in danger of cumming all over her stomach. But she stopped just in time, choosing instead to make more definitive contact with me. She grabbed my cock with both hands, holding me firmly while she began to pepper my shoulders and neck with kisses. I reached over and cupped her small but nicely rounded ass in my hands. She responded by squeezing my cock tighter and working her kisses up my chin to my waiting mouth.

We stayed in this embrace for I don't know how long. Though not exactly a virgin, my past fumbling experiences with sex had left me unprepared for the onslaught of sensations and emotions that were now overwhelming me. I guess I had started to buck insistently in her hands:

"Slow down there Stu, we've got lots of time. Don't get impatient on me now."

With that comment she disappeared into the sleeping bag. The next thing I knew she was licking my cock, teasing it really. She flicked her tongue randomly up and down my shaft, occasionally kissing the tip and then dragging her full wet lips back and forth across my hardness. I lay back, almost afraid that she was going to stop. Then, ever so slowly, those enticing lips engulfed me. As I entered her mouth I could feel her tongue continuing to flick around the bulging head of my cock. She began to bob up and down, taking most of me within her mouth. Little by little she began to pick up the tempo. In no time I was past the point of return. I whispered to her that I was about to orgasm and she pulled away, letting me explode all over the sleeping bag.

"My turn now Stu."

She crawled out of the sleeping bag and made her over to one of the empty beds in the room. She sat down on the edge of the mattress and let her legs dangle below her. She was rubbing her breasts as she spread her legs for me, beckoning me forward with her eyes. I crawled over and kneeled down on the carpet between her taut thighs, her glistening pussy a few short inches away from my face. Maybe I was showing some reluctance, goodness knows I wanted to dive in. I wanted nothing more than to lick and taste her. No, the real problem was my lack of experience. I had never done this before and I was at a loss as to where to start. She seemed to sense this, though, and put me at ease:

"Don't worry Stuart, I will tell you exactly what I want. Just do what I say."

She grabbed the back of my head and pulled me to her. She was as good as her word, guiding me along as I began to kiss and lick that stunning little pussy. She kept up a running commentary, letting me know when even the smallest changes were required in either tempo or positioning:

"....that's it Stu, now press harder with your tongue.....good, a little faster now.... Oh, not too fast Stu,.... that's right now.... Keep it up, your doing fine....now run your tongue up to my clit...."

I did exactly as instructed, all the while her smell and taste were driving me to abandon. But Jill remained assuredly in control, never letting my enthusiasm interfere with what she wanted. She climaxed with a couple of muffled orgasms and we collapsed together back on my sleeping bag. We held each other and I was hoping that after a short rest we would go a little further. But Jill told me she needed to get back to the party. She got dressed and with that she was gone.

To make a long story short, I guess you could say things developed from there. To my surprise Jill looked me up once we got back on campus. It took a few months before we engaged in a repeat performance. But soon after we were an item and for the first time in my life I had regular sex to look forward to. Jill was still Jill though, and the cost of this welcome perk was the never-ending pressure she exerted on me to do things her way. By the start of the next school year I had, at her insistence, changed my major from philosophy to economics. I continued to submit to her plans and somewhat surprisingly ended up getting an MBA. We were married the summer after I finished grad school.

As I stood at the kitchen counter preparing the sandwich I had promised myself, I couldn't help but notice that things were getting pretty snug in my shorts. So I reached down and gave myself a satisfying little tug. Despite the nagging harpy that Jill had become, there was no doubt she has the power to turn me on. Thinking about the first time we had sex had really got me going. Too bad we made love so infrequently now. I suppose I should have left her years ago. But Jill knows I'll never do that. I couldn't bear to move away from my daughter. Also I get enough time away from her at work to keep me sane. Jill doesn't dare begrudge me the 70 hour weeks I regularly put in at the office. Though I may have started my career with a certain amount of reluctance, I am thoroughly at home in the business world. I have a knack for all things fiscal and my financial prowess has been amply rewarded with both titles and salary. Jill of course loves the money I make. She doesn't have to work and is free to join useless social committees and plan never ending renovations to our overly fashionable house.

With my sandwich done, I grabbed a beer and made my way out to the pool - boner and all. Balancing both beer and sandwich in one hand, I opened the sliding glass doors and stepped out onto the deck. Something was odd though. Some of the deck chairs were out of place. I stopped and looked around when all of a sudden I saw some movement out of the corner of my eye. Off to the side and away from the pool I could make out the figure of someone reclining in a lounger. I couldn't see who, though, as their back was to me. At first I figured it had to be Jill. But with closer inspection I realized that this person was too tall and too brunette to be my diminutive wife. I was about to say something when the figure turned around and spoke:

"Oh, hi there Stuart. I was wondering when you would get home. Hey, what's that in your shorts? Oh, poor Stuie. You've been thinking about moi again, haven't you? Really, someday you are going to have to give up this sexual fascination you seem to have with me. Honestly dear, nothing can ever come of it. Now, if you're not too busy, would you mind going back inside and getting me a glass of Chardonnay. And don't bother with that swill you seem to prefer. I brought my own bottle and it's chilling in the fridge."

And with that Vivian turned back around.

FUCK! What was she doing here? This simply could not be happening. I wish it were Jill sitting there. In fact I wish it were anybody. Just as long as it was not my wife's ball breaking older sister. SHIT! What did I do to deserve this? What unforgivable sin did I commit that now requires retribution in the form of this evil spawn of Satan. Sure, maybe Jill is no prize. But compared to Vivian my wife comes off as a saint. When it comes to making those around you feel less than worthless, Jill can't even hold a candle to her older sister. Vivian is and will always be the undisputed queen of stone cold nastiness. "A bitch without peer" is how her second husband referred to her after the divorce.

I lowered my sandwich to hide my still semi-erect dick and barked: "What the fuck are you doing here? Jill and Lindsay have gone to the city for the weekend and nobody told me anything about visitors."

Vivian just laughed and spoke without bothering to face me:

"Stuart, Stuart. Like you would have any say even if someone told you. No, this has been planned for a couple of weeks. I'm having my place fumigated and Jill graciously offered up her bedroom for the weekend to keep me safe from all those nasty sprays. I'm not surprised she didn't tell you, though. Just look how emotional you are. Now, how about that glass of wine?"

I stood there for a few seconds, frozen with fury and embarrassment. I took a couple of deep breaths and decided to keep my feelings to myself. There was no telling what I would say or do in the mood I now found myself in. I turned on my heel, went inside and made my way downstairs to the TV room. I had to get my thoughts together. I couldn't believe she was here and I was livid that she had caught me with an erection. It was just like her not to let something like that pass. Dammit, why does it always work out this way between the two of us? Just once I would like something to hold over her, something that would forever melt that haughty upper-crust façade she wore with such practiced ease.

Thrice divorced, Vivian had ensured that each one of her "victims" brought her more wealth and (in a perverted way I will never understand) more social status. Of course she had no problem using both her money and social standing as weapons: means to toy with and belittle those around her. Honestly, I could write books on all the ways my sister-in-law has tormented me over the years.

For starters I would detail how she sabotaged my membership hopes at a golf club I had spent years trying to gain entry into. After a handful of futile attempts, one of the members finally took pity on me and explained how Vivian had used her nebulous connections with the membership committee to ensure I never got past the final vote.

The next chapter would then go on to detail how she screwed me out of a birthday surprise I had planned for my daughter. Back before the money really started rolling in, I saved for a full year to buy Lindsay a horse. I had my heart set on this and everyone except my daughter knew what I was up to. Then, the day before Lindsay's birthday, Vivian shows up with (you guessed it) a pony I could never hope to afford and pre-paid lessons at the most exclusive stable in town. What a fucking bitch.

I would also be remiss if I didn't mention the numerous times she has blatantly tried to split me and Jill up. Well, maybe blatant is a little too strong. Jill and Vivian don't always get along that well. But when they do talk I'm certain Vivian uses the opportunity to run me down. Sometimes I think the only reason I have stayed with Jill so long is to spite Vivian - preventing her the one victory she would dearly love to lord over me.

If this litany of abuse doesn't justify the hatred I have for my sister-in-law, I don't know what does. And this is just the start. I could go on and on. But as I sat there downstairs staring at the blank TV, sulking in the only comfortable chair in the entire house, I had to admit to myself the real reason I couldn't stand my sister-in-law. Despite all the cruel things she has done, despite every venomous barb directed by her at me, the force of my anger toward this woman actually had its genesis in the events of a weekend now 14 years in the past.

Though Jill and I were together for almost 4 years before our wedding, the only family I had ever met were her parents - and that was when they came out west to see Jill graduate from university. I knew Jill also had a sister and I knew she was married to some rich guy from Germany (Vivian's first marriage). But Jill seldom mentioned her. We planned to have our wedding back in Maine, figuring that if Jill's parents were going to put up the bucks the least we could do is have the ceremony close to their home. We arrived a couple of weeks before the wedding and made our way to my soon to be in-law's swank beach house.

The following week was a whirl of social engagements whose only purpose, as far as I could tell, was to test the outer limits of my boredom quotient. Jill was in her element, though, and was eating up all the attention being lavished on her. I, on the other hand, was surviving on pure grit. And by the weekend I had reached my limit. I think Jill sensed this as well, deciding that my gloomy presence was only going to weigh her down at the evening's planned cocktail party:

"You know Stuart, Vivian is supposed to get in tonight. Probably pretty late. It might be nice if someone was here when she arrived."

Music to my ears, finally an out. Trying desperately not to look too eager, I offered to make the sacrifice and stay home for the sake of Jill's sister. Jill flashed me a look that told me in no uncertain terms that she wasn't buying the attitude and would be exacting a steep price in the near future for her graciousness. I didn't care though, at that point no price seemed to steep. Finally I had some time to myself. For the first time in a week I felt able to take a deep breath free from all the feigned politeness and superficial niceties that seemed to underlie these plastic affairs.

Jill's parent's beach house really was incredible. The wall facing the ocean was constructed almost entirely of glass. The resulting effect was quite dramatic: as long as you were in the kitchen, dining room or living room, you felt as if you were on the beach. But I had no intention of hanging around. As soon as the cars left I made my way down to the water line and started walking. I had wanted to do this all week.

I couldn't have been any happier, the salt air was invigorating and the feeling of wet sand under my feet felt great. I could've gone on like this for miles, which is what I just about did. By the time night had fallen I finally remembered why I had been granted this reprieve. Vivian was due any time now and I needed to get back to the house. I turned around and started to hustle back. It was pretty dark, only the lights from all the beach houses told me I was making any progress. Finally at about eleven, I spotted my in-law's place and made my way up the path to their house. I saw immediately I was too late. My soon to be sister-in-law was standing in the living room staring out through those massive windows.