A Double Punishment - Part II (the most humiliating payment)

I love the feel of chiffon against my skin, so when I found a Jonathan Simkhai white blouse while thrifting on Nantucket for a steal I jumped on it. It's a smidge too tight and the neckline is a very low square cut, that though covered with chiffon mesh, it's basically transparent and leaves little to the imagination. I've only worn it around the house, or under a jacket in public, when I wanted to feel a bit risque. Now, as per this insane payment, I'm had to wear it in public, with a dark skimpy bra underneath, and “Loser” embossed on my chest, that any near-sighted octogenarian could make out twenty feet away.

Trying to match with the blouse I put on some old blue jeans, a pair of light brown soft-leather heeled boots, and I confess (as per the victor's, a brute named Anakin, requirement to report on any and all “juicy parts”) I added a racy dark gray thong to match the bra. When I glanced in the mirror my heart sank. I looked like a cheap whore who wanted to flaunt her fake boobs during a sorority pledge week stunt. But there was nothing I could do, so I got into the car drove out to go shopping.

Leaving early in the morning, when hopefully the store wouldn't be crowded, I traveled almost 45 minutes to go to a town in the next state, to avoid being seen locally. When I parked near the main entrance of the fairly large grocery store (similar to a Big Y), I paused and looked around. Thankfully it wasn't that busy, but still my stomach was in a knot, yet even with all my nervous anxiety I caught myself unwittingly fondling my breasts, my nipples shamefully hard with anticipation.

Taking a deep breath, I got out of the car and marched into the store. If anyone started to stare, I resolved to head down a different aisle or to turn away pretending to look at an item. After quickly grabbing one of the those plastic handled shopping baskets I made a beeline to the nearest aisle and picked out a few random items. I figured getting twelve items counted as “shopping” and then I would go through the self-check out and escape.

After calming down a bit, I started to focus more on the shopping. Putting the Nudges' Grillers Dog Treats back (I don't even have a dog) I began to select items I really needed. Going from aisle to aisle, I passed a few people, and thankfully no one really took notice of me. As I neared my twelfth and final grocery, it dawned on me, no one really took notice of me, not one. I know it's incredibly shallow, and again forgive my arrogance, but being female, a blonde, in okay shape (yes, I know the picture I had to post shows I could lose a few pounds in the stomach - damn I hate that picture), and having had a boob job, I'm use to at least a few guys taking a look.

Slowing down my pace, I took my time, looking over different items, returning a few, walking back and forth between the different ends of the store, and still no roaming eyes. With a defeated sigh I headed for the checkout resigned to committing myself to a nursing home. As I went towards the self checkout, I noticed the express check-out clerk looking me over. At best he was in his early twenties, maybe even a senior in high school, working a summer job. When he realized I caught him checking me out he blushed and looked away in a most adorable and ego saving fashion. Stopping and browsing at the items in front of his booth I picked up a thirteenth and fourteenth item, and then after counting the groceries somewhat out loud, I looked up at the “Twelve Items Only” sign and then at him. Giving him a quick smile, I ask “I'm a bit over, do you mind if I cheat this one time?”

Okay, yes, I knew full well what I was doing. I admit it; It's fun to play with guys once in a while to see what you can get away with by a little flirting. Besides, there was no one behind me waiting and I doubt he really minded.

“Sure.” He quickly and nervously agreed and so I started to unload my basket and while making some small talk I enjoyed his struggle on wanting to look my chest and yet not get caught.

To my surprise and confusion he eventually just glared at my cleavage.

“Loser.” He called me.

“Excuse me?” I fired back, shocked and a bit offended.

“You've got 'Loser' written on your tits.'” He crassly stated almost laughing.

My stomach wrenched in two, I had completely forgotten about how I was dressed let alone the juvenile sign scribed on my chest, making this easily making one of the “top ten blonde moments” in my life. It was my turn to blush and look away. Reflexively, I covered myself with my hand and mumbled some lie about my boyfriend and myself having too many drinks last night.

“Lucky man.” The clerk grinned.

“Yeah.” Is all I could come up with and after throwing a few twenties at him, I blurted out “keep the change.”

“Thank you!” I heard him gleefully exclaim as I fled the store.

I've haven't felt so humiliated in many many years. Sealing myself in my car I almost wanted to cry. It wasn't over, however. I now had to go home and spank myself long and hard to pay off lop747's punishment for being late on a post I owed him. I didn't cry, but instead for a brief moment, I again fondled myself, playing with my nipples, cupping my breasts, and with my finger tracing over the “Loser” written on my chest that had brought me such shame.

After the long drive that went by all to quickly, I obediently went directly to my bedroom, and after a resigned sigh, kicked off my boots and dropped my jeans. I kept the bra and shirt on, since I was commanded to wear them as part of the debt, along with the matching thong, that gave no protection, since the spanking was to be “on my bare ass.”

Grabbing my “husband”, the pink reading pillow bed wedge, I placed it in the middle of my bed, and after draping it with that “special” coarse worn towel, I mounted my favorite device to pleasure myself. With my legs spread wide, my rear end arched high, I first began to hump away, masturbating myself on my home-made sex toy. Through my little groans of sexual release, as I debased myself, I reflected on the day. This was by far the most embarrassing and degrading thing I have ever done during all my years of playing on getDare. I humiliated myself in front of a complete stranger in public. I feel like such a slut, which was only confirmed by the fact that I was gratuitously grinding away on my make-shift lover. As I began to approach what would be my first orgasm I finally remembered the main reason I propped myself on the reading pillow, and it wasn't to pleasure myself, for I had another punishment waiting for me.

“Damn it, this is going sting.” I muttered out loud as I redid the math for the number of days I was late and for the fact I wouldn't finish the story over the weekend. The revised total was 14 days, at 10 spanks per cheek for each day, that means 140 spanks for each cheek, for 280 total! Spanking is a turn on, but I've never spanked myself that many times. I began to think I kind of deserved it, however, for getting behind on several dares, being such a tease to the clerk, let alone being so stupid by forgetting what was I was wearing and what was written on my chest. This is the fate of those who lose and act shamefully, I realized, they are to humiliated and punished.

So, I started to spank myself, hard, as the payment required. As I tanned my ass bright crimson red I grinded away on the husband with even more intensely, the increasing painful stings only driving the insatiable disgraceful pleasure.

I confess, a few times I had to briefly stop my spanking. Twice because the sting became too much, which only made the next spank hurt even more. Once to strip off my thong, so that I could have better “contact” with my lover. And a couple times because of the increase intensity of the now rolling orgasm. All this caused me to lose count more then once. I probably spanked myself well over 300 times that day, just to make sure I paid my debt in full, and also merely out of sinful pleasure.

After the final spank, even with my ass now bruised, beaten and searing red, I continued to masturbate. Though the pain was bad, what was even worse was the realization that I would have to write in complete delete, this most humiliating day on getDare, and post it on the internet. In my mind's eye, I saw the clerk looking down at me with lustful glee. Then there was lop747, inspecting my ravaged ass cheeks with approval. And finally, I was in the getDare chat room. Anakin's voice was heard clearly over the cheers, jeers and cat-calls, “lose the shirt and bra, bitch,” he commanded, ordering me to strip naked for all to see, for I had to “make those tits bounce for the room.”

“You fucking bastard!” I think I said, almost yelling out loud, as I complied to this final degrading. Clumsily, I ripped off my blouse and bra, my hands shaking for the mental shame, rage and lust, that now felt so clear in my imagination. I bucked away on the pillow, arching my back, my bare breasts violently flopping around, to the point of pain, as I rocked myself to an explosive finish. When I was spent, sexually, physically, and mentally, I fell over into the bed, kicking the husband to the floor, while wrapping myself in one of my quilts. As my defeated sweat covered body quivered away, trying to recover from such an intense ass-whipping and even more powerful forced orgasm, I could hear Anakin laugh with sadistic satisfaction.