My Sister's Teddy Bear

My sister left me her teddy bear when she started college.

It really should've been our teddy bear. Dad won it for both of us at the Livingston County Fair and Rodeo on one of those rigged balloon popping games, shortly after the accident...

Who knows how much money he must have poured into distracting us, but he probably could have purchased the real thing instead of the fuzzy, plush, entirely too comfortable human-size teddy bear. But Ted Danson (our dad picked the name) became part of the family, a symbolic memory of how our family got through the tragedy.

Technically it was both of ours, but it had to stay in one room. And while I got visitation some nights, as time went on my dad became less vigorous about enforcing the rule about sharing, until even I began to think of it as Madison's.

I suppose we had our fair share of fights, but for the most part, I lived in awe of my sister. Like every younger sister, I was always trying to fit in with her older, cooler friends. There had been this clash when I was still in junior high, when my sister was the freshman, where the location and age difference proved a barrier. But once I got to high school, there was a gradual blending of our worlds.

For the past few years, we had been nearly inseparable, exactly like when we were kids. We played volleyball together, loved the same art teacher, and on some nights when I woke up from a particularly bad night terror, she let me sneak into her bed, head nestled against her larger bosom, soothed by the sound of her breathing...

I have had night terrors since the accident.

I can't say that Madison became like a mom, that would have been too much to ask, but she tried to bridge the gap. She answered all those uncomfortable questions, helped me through those awkward questions and earlier bras, even if my chest never transformed to her size.

We didn't look anything alike, a constant source of anxiety for an introvert like me. Madison was blonde, I had darker, chestnut-colored hair. I guess we were both pretty, but in a different sort of way. Or maybe I was cute and she was hot.

She had the flamboyant, flirting personality while I was the dark and brooding artist, more interested in my sketchbook then boys. She belonged as Prom Queen or Head Cheerleader, though both sorts of posturing were beneath her. I guess I was more the shy, kind of cool girl at the comic book store, the mythical one who actually enjoys the artwork.

I didn't really know what I was going to do without my sister. All of my friends had been inherited, and there was this gnawing dread that my popularity would wane without her.

And that I wouldn't do a damn thing to stop it.

Of course, I got more hand-me-downs with the course of her move. It brought me to tears several times (an easy enough thing to do), reminding me too much of the day we went through all of Mom's things, deciding what to keep and what to throw away. I remember thinking identical thoughts about each object, from the old torn and stained script of that freshman play to those Taco Bell advertisements.

Stupid, I know, but everything they made me throw away made me feel as though it was another part of her I would forget. It was the same thing with Mom. Each of these things came imbued with a memory, and yeah I might just hold onto that time we stole a box of advertising pamphlets and built them into a paper house while Martin looked frantically for them...

But what if I forgot?

What if I forget that senior English paper Madison turned on The Grapes of Wraith? How I'd noticed the spelling mistake right before fifth period when it was far too late to do anything about it? What if I forgot that ratty looking trapper keeper she carried to class, those days she bothered to bring as much a pencil?

There were many patient arguments (ok, temper tantrums) as we decided what to pack, what I would keep, and what to throw away.

Okay, so I didn't take it well.

I inherited enough nonsense to be a cold open on a hoarding documentary, but the big haul was her old computer now that she had a new laptop to take with her to college.

And of course, Ted Danzon, who began to serve as a pillow/surrogate sister.

I would sleep in on his oversized chest, draping his heavy arms around me, noticing that he still smelled like her...

School had been the hardest, it was a place that I had only experienced through Madison, my sherpa through the maze of high school. Feeling alone and isolated, I withdrew a lot at the start of my senior year, feeding into my depression. I harbored this thought, the idea that Mom's death had been harder on everyone else, because Dad and Madison had to look after me.

I was wallowing.

It was a month before I used the computer to fill out an SAT registration. But once I finished, I started casually clicking around, finding a treasure trove of memories. There were pictures of all of us, different plays and short stories I'd written, memes and inside jokes, enough of a virtual claptrap of nostalgia to satisfy me for weeks...

I don't even know what anything was labeled. Madison had the tendency of naming her files based on whatever feeling she currently wanted to express. So documents titled Fuck Me Or Ms. K Takes It Up the Ass were actually old homework assignments. But I was doing a thorough search, really wading into the depths of self-pity when I saw the first one...

Madison posed up against the gigantic teddy bear, her legs and ass on display in those tight-fitting black volleyball shorts. But there was no sports bra or uniform on her bare back. It was almost tasteful, like a 1950's cheesecake shot a wife might send her soldier.

Still, my eyes lingered on the bulge of her breasts, her nipples hidden by Ted's fur.

I shot him a knowing look, then let out a laugh.

I knew my sister had sex. Telling me the details had been part of the deal in exchange for me covering with Dad. But this was new. But from the timestamp on the webcam, I couldn't match up the photo with any ex-boyfriend.

Had she just done this for fun?

There were dozens of other pictures and videos in the innocuously titled file. For days, I blocked out my curiosity, trying to respect her privacy even as those rationalizations snuck into my head. After all, we had showered together on the team. I'd seen her naked and knew all about the three men she'd fucked.

But it became an obsession. Most of all, I remembered the look on her face, how much fun she seemed to be having in this private display of exhibitionism.

It was so her.

And yet I didn't think entirely about her face. I tried rationalizing it away even as I squirmed in my seat, trying to pretend my pussy wasn't responding to these incestuous thoughts.

I promised I wouldn't snoop, so I started sketching, trying to recreate the idyllic image, needing to capture how beautiful she had looked with my pencil.

And that's where it started...

I decided to look again, just for reference, forcing myself not to think about the tingling wetness below my waist.

More than a few times during the week, I'd resorted to rubbing my pussy against my favorite blanket. I know it sounds like a silly way to masturbate. Madison had even bought me a vibrator, I just hadn't been ready to use it.

I guess I was easing myself into it, content to let the desire build and build until I let it out by rubbing my thighs together against my Mickey Mouse blanket. There was something about it, the texture, the release after waiting for weeks. But a lot of times it overwhelmed me emotionally, and I started crying.

Once Madison had heard me, rushing into the bedroom to check on me. I had only been wearing a t-shirt, afraid that she knew what I had just been doing. And with the orgasm still not yet subsidized and my tears falling, my sister had held me, cuddling me until I calmed down.

And after...

It embarrassed me how I remembered it rather than what happened. I tried to tell myself it was natural. That I was just too inexperienced, because I couldn't deny the truth of it.

It had been the best sex of my life.

Is masturbation sex? Not technically, but emotionally? Mentally?

I like to think sexual expression is still special when it occurs alone. Masturbation can be self-love instead of self-hate if it isn't always perceived as a substandard substitute. Maybe it was just being eighteen, but I had been happy to take my time with myself, perpetually petrified at feeling silly at the end of another weeping climax.

Until now...

I thought of looking for that vibrator Madison had bought me, stopped only by the thought of what she would think of her sister fucking herself to the first time to her naughty pictures. So I forced down my feelings, rationalizing it, focusing on making each line exactly as the vision pixelated on the screen.

I finished, holding my drawing up to see the two images of my sister with her teddy bear.

She looked perfect.

I should have stopped then. All I can say is that I did pause, trying desperately to stop myself before clicking on the rest of the gallery.

I saw her turn, her nipples hard and swollen, one hand playfully tweaking them, the other reaching down into her black bottoms. The camera roll came out in a burst, creating these animated GIF presentations of my sister slowly pulling down the bottom, hiding her pussy as her breasts and hair bounced down.

Then she placed her hands on her hips.

My eyes went right to her bare vagina, just like her strip-tease intended.

Sure, I'd seen her naked, but not like this, so overtly sexual in the first of a dozen full-frontal photos.

And Madison was beaming, almost giddy with a natural smile.

I hadn't touched myself, not yet, but I could feel the fabric of my underwear against my pussy as I compulsively opened and closed my legs. It wasn't just a little wetness now, my panties were soaking wet, clinging to my cunt as I tried to hide the small little tingle of pleasure I got from moving just a little against the leg of the stuffed bear.

I could see Madison in between his legs, spreading her thighs and using two fingers to spread open her lips like a professional. I gasped, really seeing inside of my sister in a dozen more close-ups, then the camera pulled back to a different position.

This time, I saw my sister in a position remarkably like what I was doing, only facing the opposite direction. Her legs were spread in between the thigh of our teddy bear, her arms wrapped around Ted's shoulders, as though she was sitting naked on her boyfriend's lap.

Then photos changed into another animation, showing my sister grinding her pussy and down on the teddy bear's thigh. Her buttocks clenched, her head tilted back, facing the camera, a look of pure ecstasy on her face as she shook on the stuffed animal.

Was I watching her cum?

When I confessed to her about rubbing my blanket between my legs, so scared of sounding stupid, she had reassured me I was normal.

Madison said she had first used a stuffed animal...

At the time, I'd been too embarrassed to even think about it.

I looked away from my sister's naked body, absolutely glowing on the screen, before realizing how much I was rocking on Ted. His fur seemed to bristle in just the right way, his pelt exactly the right texture against my skin...

I thought about it, again for only a moment.

My panties never made it down my ankles as I scooted up and down the nearly person-sized leg. I twisted and turned, using my hands to hold him still as I slid up and down, too horny to care about the utter humiliation if I was discovered in this position. The computer continued playing the animation, me mimicking my sister in reverse, rubbing as her naked body titillated me again and again in my few and fading moments of focus.

Our teddy bear felt so good against my clit...

I adjusted, taking off my panties and shirt so that I could mimic my sister, fully nude and intimate with our teddy bear. Then I sat back against him, adjusting into the perfect position. I held his leg a little with my hands, bending down a little for leverage as I gyrated away, using my muscular thighs to squeeze around him as I bucked.

I craned my neck, struggling to both see and sate my aching pussy. I could sense the rising tingle up my pelvis, the anticipatory beginnings of the climax let loose in hot white warning flashes as I reached my finale, stopping only long enough to look at Madison one last time.

God, she was so beautiful.

I convulsed, nearly falling off Ted as the strongest orgasm of life overpowered my inexperienced sex. I shook and thrashed so suddenly that the only thing keeping me in place was my desperate desire for more. The last few waves of ecstasy slowed me down, turning me into a melted heap of contentment...

Curdling instantly into remorse and loneliness...

I cried, starting even before the afterglow of my orgasm ended, pouring out an ugly mixture of tears and mucus into Ted Danson, his plush arms strapped around me. I hugged him tight, letting him cuddle me, trying to again smell my sister over the fresh musk of sex...

It was enough to think of her, holding me after hysterical crying...

Enough to soothe me to sleep...

I can't really know what I dreamt and what I just wished I had imagined that vividly, but I had this image of Madison lying naked next to me.

Stroking my hair...

Understanding how I felt about her.