The Winter of My Delight Pt. 01

I used to be quite the barfly, scoring free drinks off the horny men I flirted with while pretending to care about whatever they prattled on about. It didn't matter to me, so long as I got free booze and their undivided attention.

Back in my heyday, I was smoking hot. Giant D-sized breasts that simply defied gravity. I kept myself fit and trim, exercising on the regular. My fiery red hair and sparkling green eyes would draw everyone's attention as I entered the bar.

I would select whatever lucky man most caught my interest that night, saunter on up to him, and let him buy me drinks as he discreetly felt me up.

More nights than not, my time at the bar would end with the guy driving me out to a hotel where I repaid the drinks with a night of sex, the rougher and more humiliating, the better. That was the only way I knew of to banish the demons haunting me from the dysfunctional, abusive house I'd grown up in.

As I got older, my breasts started to sag, and my metabolism slowed down. I gained a little weight, not enough to truly be fat, but enough to no longer be the pornstar of men's wildest fantasies. As my face wrinkled and my hair grew grayer and thinner, I attracted fewer and fewer men. I started having to be less and picky to keep the free booze flowing.

I started choosing men looking to do nastier and more dangerous things to me. I began saying yes to sleazier and dirtier men to keep the attention I craved to distract me from my pain. In the past two decades, I've lost track of how often I've been beaten, pissed on, smeared with shit, and eaten out filthy butt cracks just to keep the booze flowing. Often, instead of going to a hotel, I'd be dragged to the men's bathroom of the bar, the whole place privy to the sounds of my abuse. To my shame, I also found myself aroused ever deeper as I stooped to new lows to please the dirt bags I serviced. Up until a couple years ago, I had a steady stream of nasty men who enjoyed taking advantage of my "services" to do the kinds of things to me no woman with self-respect would let them do. I still masturbate to those memories, re-enacting pieces of them in my mind as I stick my fingers up my crotch.

This kind of man would often grow bored of me after I fulfilled their fantasies a couple times. They would soon stop showing up at the bar, deciding to look for more "respectable" hookups in other joints. Over time, I became known as the bar's discount whore, willing to do anything for a shot of alcohol. The regulars shunned me, but I never cared, so long as I was able to get drunk.

Unfortunately, as I got older, fewer and fewer men saw me as a sex object, no matter how enticing I tried to make myself. I'm now 63, and I end up spending the night at the bar alone far too often. I'm far too broke to afford enough booze to get my alcoholic body drunk by myself, and the bartender knows me too well to let me open up a tab. He'd gotten burned too many times in the past when I'd guzzled more booze than I could pay for.

Tonight, I ordered a rideshare home and waited for it to arrive. I was horny again, and started idly playing with my crotch. My underwear disappeared, lying crumpled on the street, forgotten; I have no idea where. I gave myself easy access to play with my pussy. As I stimulated myself rubbing my fingers against the ring piercing my clit, my mind drifted back to a time I had been stiffed on a bottle of booze, one of the darkest, most erotic incidents in my adult life...

15 years ago, I was still in the attractive MILF range. I flirted with Mike, the new bartender there to make sure I stayed on his good side. I'd learned that it could save me a lot of hassle if the bartender kept an eye out for my welfare if things got out of hand.

I even offered to give him a blowjob once after he kept a particularly nasty customer from grabbing me by the arm and dragging me off, threatening to sell me to his favorite brothel. The greatest humiliation that night was the gentle pity in Mike's eyes when he turned me down, saying that he didn't need anything from me.

I repaid his kindness three years later by climbing all over that same cruel prick when he offered me a bottle of vodka to go with him back to his friend's hotel so the two of them could spitroast me while they watched late night TV. He'd already bought me enough shots of whisky that my judgment was impaired; I said yes.

The look of disappointment and hurt in Mike's eyes burned me as the prick grabbed my arm and roughly dragged me off. He had me give him a handjob in the cab of his truck as he drove back to the hotel.

Once we made it to the room and the door closed, he swept me off the ground in a crushing bear hug. His friend threw a hood over my head and they set me down. The two tore my clothes apart stripping me bare. They proceeded to make a game of pinching me and twisting as hard as they could before I pushed their hands away. My nipples, ass cheeks, and pussy lips were favorite spots. They tormented me for a solid five minutes this way, sniggering when they got me to yelp in pain. This attention caused my cunt began to quiver in anticipation. As cruel and degrading as it was, the danger excited me.

Once they grew bored with that, they guided me across the room and placed me on my hands and knees before taking the hood off. They had pulled a pair of chairs in the hotel suite facing each other right in front of the tv. I was kneeling on the floor between them. My johns for the night were sitting in the chairs above me, their legs fencing me in.

One shoved his dick up my ass and put his feet on the small of my back. The other scooted his chair up until his dick was in my mouth before also placing his feet on my back.

"get busy, slut," the prick I'd rejected in the past said, "Fuck his dick with your ass while sucking me off."

I hurriedly began to obey, excited by the uniquely degrading experience. Once I had a good rhythm established, he turned on the tv to a random channel. The two of them engaged in small talk, ignoring me completely unless I slowed my pace on either end too much. That would cause the one unhappy with me to grind his shoe into me, a reminder of why I was there.

I thought I'd discovered the lowest I could get in that moment. I was being used as a fuckable ottoman by two men who didn't even consider me worthy of insulting. I had the same function as the tv: a background entertainment as the two men reminisced about old times.

When his friend came in my ass, he put his feet down, grabbed my hair, and twisted my head until I managed to awkwardly turn around between them.

When I was finally repositioned, the friend shoved his now-flaccid, shit-smeared dick in my mouth, indicating I should suck his dick clean. The prick, meanwhile, got up, stood on my ankles, pinning them, and jacked off onto my back. Hot strings of jizz sprayed across my back and into my hair. When the friend had determined I'd cleaned his dick well enough, he nodded to the prick who twisted my head around and made me suck out the last drops of cum. They used my hair to wipe their dicks dry.

They sat back down and propped their feet up on me. Then the two of them had the conversation which lead to an even newer low.

"Damn, bro. What did this skank do to you? I've never seen you fuck a whore with such a hate boner."

"Yeah, I know; this one's personal. The uppity bitch rejected me a while back, thought she was too good for me. Slapped me and laughed in my face as her pet bartender threw me out that night. I've been waiting years for her to become desperate enough to come crawling back to me. You should have seen the barkeep's face as the bitch walked out with me. The little twink looked so hurt."

"What the hell? This trash thought she was too good for you?"

"Well, she used to, back when she was a little younger and her tits didn't sag quite so much."

"Speaking of, I saw a porno once where two dudes played darts, except they used an old whore's giant, saggy tits as dart boards. Do you think this bitch would let us try that with her?"

"I dunno" he said, "Let's find out"

For the first time since I got there, both men gave me their undivided attention and spoke to me.

"What do you say, doll? Mind if we play a game with you?"

I had agreed to stay with them all night, fuck them, and even try to get them stiff afterwards to try for round two, but I hadn't agreed to be their pincushion for a game of darts. I was already sore and it was beginning to look more and more like they were lying about giving me booze as a parting gift.

However, my pussy had never been more wet and aroused. Against my better judgment, I just couldn't resist the thought.

"Yes!" I quickly said, before I could let my brain stop my pussy from deciding.

My world was spinning as they hollered in excitement. Had I really just agreed to this? Was I really so excited by the idea of letting two strangers play a game with my body? Was I really that pathetic of a booze whore?

YES was the resounding answer from my twisted, fucked-up soul. Yes we are this kind of depraved.

"Cunt, get up and stand against the wall by the bed, arms and legs spread wide for us.

To my shame, I meekly did just that. I was humiliated, willingly choosing the most depraved, dehumanizing act of my life. I'd never been more turned on.

I was thrilled by the danger of not knowing what would happen, if I would ever be free of these two, or if I'd just signed up for a lifetime of degradation and slavery. My pussy lips were slippery, sliding against each other as I walked up to the wall and pressed my back into it, limbs spread wide.

Prick walked up and threw that bag over my head again. His arms pinned mine arms to the wall as his friend taped them down with industrial-strength adhesive tape. Its acrid glue gripped my skin tight, threatening to never let go. They then pulled my legs further apart until, stretching me until I thought I would tear. The growing tension stimulated something deep in my aged cunt, and the pain of their maneuver pushed me over the edge. It was the most powerful, crushing orgasm I have ever had.

That was the first time I came during my time as a human dart board that night; it was far from my last.

My shoulders sagged and I was mildly delirious as they taped my legs to the wall as well. Once they were done with that, they applied several wide strips across my chest underneath my breasts so tightly I could barely draw breath, pinning me in place.

My legs ached, I could only take in shallow breaths, and my crotch burned with need, already demanding more stimulation. I felt my juices build up on the tips of my pussy lips, dripping and forming small streaks of fluid along the wall. The bag came off my head as they shoved my panties in my mouth to gag me, taping it shut. They then put a blacked out face shield on my head, promising they'd treat me right by "protecting the money maker." The derisive snorts that followed their proclamation underscored their "concern" for my safety and ignited a twitch in my pussy, leading to another orgasm. I found myself dreading and anticipating what was to come.

The two of them drew targets on my breasts, each nipple a bullseye. They then each wrote something on my chest just above my breasts. I discovered later that they had each signed their names above one of the targets. They then went back and forth throwing darts at me that night. Both of them were terrible shots and most darts missed me or would land on my belly or chest. They insisted that they would keep going until they each got a bullseye. Time crawled past as they alternated shots. They kept tally marks under their signatures, denoting how many rounds passed before they succeeded.

Eventually, one of them succeeded in pinning my areola. That dart was left in as a trophy. The other man began unleashing a stream of darts, trying to match the feat while the first one just sat there laughing at him. Another twelve shots later, he landed his mark as well. As the two of them inspected their handiwork, they noticed a trickle of fluid trickling down the wall.

"Aw, shit, did the bitch piss herself?"

"No way, bro. You made sure she peed before she left the bar, right?"

"True, true. Wait, you don't think she-"

"Aw, shit! Yeah, bro, I think so!"

Each of them stuck two fingers up my vagina and took their hands back. They each took a long, hard sniff before busting into uncontrollable laughter. From the moment the darts started flying, I had found myself so stimulated by the fear and humiliation that I had begun to cum repeatedly, each orgasm flowing into the next.

Exhausted, I felt darkness overtake me as the two of them tried to wedge a bottle of beer up my cunt. I had a stray thought, wondering if it would fit. I'd take wine bottles up there before, but I had always warmed up to it, and they hadn't done any prep work. I didn't know if I was loose enough to take it. My musings faded away as the world faded to black.

When I woke up, the suite was lit only by the flickering light of the tv, left on with a commercial for some brand of cereal playing. My tormentors were snoring loudly, cradling each other in a gentle embrace. With a start, I realized that I had been left on the wall, a forgotten, discarded toy. The beer bottle they had been trying to shove in me had rolled under the edge of the bed. I figured they had managed to get it up there, but it had fallen out and rolled sometime after they collapsed into bed together.

My weight pulled on the tape and loosened it enough that I managed to tear one of my arms free. After removing my gag and spitting my underwear out, I got myself down from the wall, falling with a thud to the floor. I paused for a long moment, afraid I had woken the two of them. They continued to snore.

One of the darts left in my nipples came loose as I fell. To my surprise, I realized I'd forgotten they were there. I carefully removed the other as I got to my feet. I took a moment to examine myself in the bathroom mirror. That was when I discovered their signatures, as well as the tallies declaring it took them seven and ten rounds each to hit their mark. My breasts were covered in pinpricks where their darts had stuck, tiny red spots that looked like mosquito bites. Removing the remaining tape was agony, the sticky stuff peeling off only slowly and with great effort. I bit down on a towel to prevent myself from screaming as I removed each strip, inch by painful inch. My skin protested the abuse, marking the ordeal with wide, red stripes. Doing the best I could to clean myself while staying quiet, I decided it was time to leave. My clothes were shredded so I stole one of their shirts to cover myself and fled into the night.

At least, I started to. I made it all the way to the door. I even reached the handle, but then I remembered that bottle of beer. Those pricks owed me alcohol, and if I wasn't going to get the full payment for my services, at least I could take the consolation prize. Besides, after what they just did to me, I could really use another drink...

I crawled under the bed, fumbling for the bottle. Just as I found it, the bed creaked, and I froze, terrified they would wake up and notice their entertainment had fled.

After a brief eternity, I decided they must have just shifted in bed, and crawled my way back out. I quickly darted out the slammed the door shut, and leaned up against it to drink my beer. I had earned it.

I didn't have anything else to open it with, so I had to pry off the cap with my teeth. While it hurt and was slow, I pried it open and began to gulp. Once emptied, I dropped the bottle in the hall and made my way home to crash and recover.

There are still nights I think back to that time and fantasize about what would have happened had I stayed, whether they would wake up and inflict new torments upon me, or whether they would have left me there when they checked out the next morning, leaving me to be discovered by the cleaning staff. I find the thought of both scenarios gets me wet fantasizing about it. I begin to play with myself as a sit on the sidewalk waiting for my ride.

I'm still fingering myself, my dress hiked up to my waist with no underwear in sight when my ride showed up. The 18-year old boy behind the driver's seat rolled down his window to confirm I was his ride when he realizes what I am doing an stares at me, hypnotized by the sight of a woman old enough to be his grandmother masturbating on the sidewalk.

The disgrace of the 18-year old boy staring at me brought me to climax quickly. Once my business is finished, I lean up against the driver's door to thank him for waiting. In my drunken, lurching state, one of my breasts slipped out and dangled between us. He stared at my wrinkled, pointy nipple as it wobbled back and forth.

"Thanks for waiting." I croaked, barely able to speak. I tried to present my breast for him to hold if he'd like, but the kid snaps out of his trance and told me to get in. Disappointed, I climbed into the back behind the passenger seat.

I grew bored on the twenty minute trip home, so I decided to play with the driver some more. I slipped my dress straps of my shoulders and let the top half of my dress fall down around my waist. Topless in the kid's back seat, I set about playing with my saggy tits, giving the kid a show. I reached up under each udder and began waving them about, angling them so my wrinkled nipples pointed straight up.

He becomes so distracted staring in the rearview mirror he misses a light and nearly t-bones an oncoming car. I cackle hoarsely as he snaps his attention forward. He studiously adjusts his mirror to avoid any further distraction and takes me to my destination.

When we arrive, he unlocks his car.

"Out."

That was the only thing he said to me, clearly still pissed off at the stunt I had pulled. I stumbled over to my front door and slumped down with my back against it. My world started to spin and I became ill. Vomit boiled its way up my throat and dribbled over my chin and down my exposed chest. After soaking through my dress, my bare ass sat in a puddle of my own filth. I then realize I'd pissed myself sometime since slumping down. The acrid smell of my own mixed excrement filled my nose as I blacked out.

I remember dreaming of violent, erotic, dark delights, one scene blurring into the next, though if pressed, I cannot figure out how to form them into words.

I woke up with the morning sun shoving spears of burning lights into my eyes. I was cold, damp, completely naked, my left tit hurt, and I was absolutely horny. After taking a minute to satisfy myself with my fingers, I reach up to the tit irritant and pull out the push pin, grabbing the note underneath and peering at the note my landlord left me. It was our system for him to communicate should he find me passed out. A both practical and fun system. The note read:

"Had to let you in your apartment. Again. I've hosed you off and fucked your cunt. Take a shower you damn whore. You reek."

He let me stay rent-free and I was his free use plaything anytime he felt like it. He was a busy, and rarely had time to indulge. Still, he was a sadist and enjoyed tormenting me from time to time. His youthful vigor was flattering to this flabby old cunt.

It was my idea for him to pin notes to my tits if I passed out and he wanted to tell me something. One of my favorite decisions, as it often meant I had a keepsake to my fun nights out, and those were getting rare enough that I started to value them much more than I did as a young slut taking her sexual power for granted.

As I playfully rubbed the pinprick, I basked in the joy of my life. I'm an old, horny bitch. I'm a filthy skank who's done it all, and gotten off to the most horrible, degrading, painful things imaginable. As I groan through the hangover threatening to tear my head in half, I consider how lucky I am to get to have this much fun as I fuck my way into my twilight years