tagAnalWhich Hole Is That?

Which Hole Is That?

byDiggMe©

I walked into the bar just after 9 pm. It was a new place to me, first time I had been in it, or in this town for that matter. The day had been rough and I needed to relax a bit and unwind. For me that meant a couple of beers and shooting some pool. I just wished that I had brought along a pair of jeans to wear, but I had not planned on a casual night out and made do with what I had in my bag.

The bar was your typical biker pub. Well maybe they wouldn't mess with me. The parking lot was fairly empty so I figured I would be ok. I went in, bought a bottle of Miller Lite and got some quarters for the pool table. There was an empty table in the corner so I went over, set down my beer and opened my pool case to get my stick. Glancing around, I noticed there were several people with their own sticks, so I figured I wasn't out of line there either.

I rarely played pool in anything but jeans. This night I had on a low cut tight stretchy tank top and a skirt that swished around my knees. I usually wear longer skirts to help hide my ample ass but this one was shorter and very full and I really liked the way I looked in it. I had pulled on my favorite pair of undies, black satin bikinis that tie on both hips and some black seamed thigh high hose with a black lace garter belt. Since a car accident in the 80s I couldn't wear high heels, not my preferred 4-5 inch heels, but I had pulled on a pair of 2 inch mules, against doctors orders. Under my tank top I wore one of my favorite front hook black lace bras, I like to buy them a size too small so they make my breasts look more impressive. Not that I think they are that impressive, but a modest 40B usually gets a few looks.

I racked up the balls and, chalking my stick as I walked around the table, studied the balls and planned my game. I began walking my way around the table, practicing a few harder shots and working on relaxing my mind. I glanced up when you walking in the door and went to the bar for a drink. I couldn't help noticing you, as you glanced around the room. I felt your eyes resting on me. Just as I sank the last ball you walked over to my table and asked me if I wanted a game.

I took a moment to study you before I answered. Looking up, I figured you for about 6'1 or 2" over a foot taller than my 4' 11 3/4" in my bare feet. I guess I could claim 5' in my heels. Short cropped brown hair with a touch of grey, blue eyes and a nice bushy mustache. Inwardly I blushed, imagining a mustache ride. Clean cut and dressed carefully, however, casually, I didn't feel threatened, so I agreed to the game.

Since it was my table, you racked the balls and I bent over the kitchen to break. The first game I won convincingly, the second you suggested a side bet of a drink. That was fine and when I won you walked over to the bar for my Lite and another soda for you. By the third game I was beginning to feel the beers, becoming more relaxed and flirty. You seemed to enjoy that. The next game you asked for a more interesting bet...underwear. If I won, you would give me your boxers (you would go to the bathroom and remove them). If you won, you wanted to claim your prize right there at the table. Well I figured since they tied on the sides, I could get them off without too much show, so I agreed. After all I had won 3 straight games.

And I was hustled. I broke the table and never got another shot. You ran the table and then walked up behind me running your hands down the sides of my thighs.

"Ok, I want my prize and I get to remove them." you whispered in my ear. Your hand slid up the side of one of my thighs, pushing my skirt before it until you reached the tie on the side of my panties. You pulled on the end and it easily came untied. You let my skirt drop a bit and started pushing up the other side to finish claiming your prize. Once you had untied the other edge, you pushed my feet apart slightly with your feet and they fell down to the floor.

You turned me around, grasping my shoulders and leaned down to kiss me, pushing your tongue into my mouth, your mustache tickling my upper lip. Instinctively I sucked on your tongue, hard, pulling it farther into my mouth. One of your hands snaked down to my chest and you brushed your hand across my nipple.

I sucked in my breath quickly, feeling myself flush. You leaned down and whispered into my ear.

"How about something a little more dangerous?"

"What do you have in mind" I gasped back.

"If you win, I'll set you right on this table and give you a mustache ride you will never forget." I looked at him startled, had he read my mind, I thought. "If I win, I will claim my prize right here on the table too."

I looked over at him, "and just what prize would that be?"

"I want to fuck your ass" you said looking into my eyes.

My heart skipped a beat. Could this man really see into my mind? How did he know that I had been thinking about having anal sex lately? That it had been the center of my fantasies for months? And to be forced to give it up in front of strangers? Win or lose, the men in the bar were in for a show. I only hoped that watching would be the extent of it.

"Alright,"I agreed "on one condition"

"What would that be?" you replied.

"I just don't want this to turn into a gang bang, can you keep me safe that way?"

"I am sure I can" you replied. And since you are a good sized man I felt you could.

"I think you can too. You're on."

The game seemed to go on forever. We both missed shot after shot but before long we were both on the 8 ball. After several attempts, you finally made the shot and won the game. Every time we had passed, walking around the table, you had run your hands over my ass or down my hip. I had the feeling you didn't have a problem with my big ass.

The one mistake I did make, was not looking down sooner. It wasn't until you made the 8 ball, that I looked down at the bulge in your trousers. I could see the outline of your cock against your pants leg. It looked enormous! I had seen longer cocks, had enjoyed a few of them too, but I had never seen one near as wide as the one hidden in your pants appeared. I know the popular word now a days is "girth" well I could see, that yours had a lot of girth!

A look of panic crossed my face. When you saw it you walked over to me and leaned down. Kissing me deeply, you ran your hands over my ass and began pulling my skirt up.

"Don't worry," you whispered, "I bet you can find something in your purse to use as lube"

I looked up at you in shock then went and grabbed my purse. Digging around in it I found a small tube of flavored body oil. I handed it to you. You grabbed my arm and steered me back over to the pool table. Taking hold of the bottom of my tank top, you pulled it over my head and tossed it aside on the table. That got the attention of everyone in the bar. The bartender walked over to the front door and locked it, turning on the closed light. He grabbed a chair and took a front row seat to watch. Men gathered around on all sides.

"She lost a bet and I am going to claim my prize right now " you told the crowd. "I promised her that she would be safe, so you all can watch but no one joins in and no one tries to hurt her . Are you all ok with that? "

You looked over the crowd as the nodded in agreement. With that, you unhooked my bra and let my boobs pop free. My nipples were already puckered and you took a moment to suck on each one till they were hard. I moaned in pleasure, loving the attention to my breasts. With your hands you picked me up and sat me on the edge of the table, flipping my skirt up to take a look at my pussy.

"Well I prefer them shaved, but it'll due for now. I'm not having it anyway." You could see that my hair was damp and you dipped a finger into my slit, wetting it. You brought your finger to your lips, snaking a tongue out for a small taste, before shoving it into my own mouth .

"I want you to watch this" you said as you pulled off your shirt and laid it on the table. I could see that age was beginning to show, your stomach starting to loose the tightness of a younger man, still not bad though. My eyes followed your hands to your belt as you undid it, watching as you lowered your zipper and stepped out of your pants, putting them neatly with your shirt. I could see the tip of your cock peaking out of the leg of your boxers.

Next you pushed your boxers down and off your feet. As you stood back up your cock leaped into sight. My eyes widened as I saw it. I had thought it was huge and it was, bigger than anything I had ever seen before. I knew my small hand would never go around it. You pulled me off the table and put steady pressure on my shoulders so that I was forced to my knees. You pushed the head of your cock toward my mouth . I knew I would never get it all in but I did try, since it was already hard I didn't need to get him up, so I concentrated on licking it all over and getting it wet. After a few minutes you stepped back and stood me up again .

Turning me around, you picked me up slightly, so that the bend of my legs was at the edge of the table, my feet dangling inches off the floor. Flipping my skirt up over my waist, you stepped between my legs, pulling them apart. The position you put me in pressed my breasts down onto the rough felt of the table and the roughness caused my nipples to harden more.

You took the head of your cock and rubbed it along my slit a few times, eliciting a moan from my lips. I was trying my best to relax. You picked up the bottle of oil and squirted some into the bud of my ass, following with a finger, pushing oil into my tunnel. Even your finger was big in my ass. I was thankful for the oil and you were generous with it. I knew you wanted my ass more than anything, but I was glad you didn't seem to want to hurt me in the process. Well, at least not hurt me much.

The men were jockeying around for a better view and I heard several of them comment on the size of your cock. Finally you doused your cock with the oil, covering it as much as you could. I felt you press the head of your hard cock against my tiny hole. I stiffened momentarily. Relax I told myself, if you don't its going to hurt like hell. I sucked in a deep breath and let it out slow willing myself to relax my muscles and I felt the head of your cock force its way into my tunnel.

Most men would have stopped right there and let the body adjust, but you are not most men. You kept up steady pressure, continually pushing against me, your hands grabbing my hips. I felt my anal muscles stretching. Inch by inch, your massive cock wormed its way into my ass until over half of it was imbedded. The men watching started hooting and hollering. That seemed to spur you on and with a sudden push you shoved the rest of your cock into my ass. My mouth opened in shock, a grunt escaping my lips. Now you rested for a moment, the fronts of your legs pressed against the pool table, your balls slapped against my pussy. The audience really enjoyed that. And then you started pulling your cock back out as the walls of my tunnel gripped it. You pulled out till the head was just inside the ring and then shoved again. This time it slid in much easier. That was all the encouragement you needed.

Taking a firmer grip on my hips, you began positioning your cock into my ass, drilling it as fast and as hard as you could. Each stroke seemed to be harder than the last one. The force of your strokes causing my legs to bounce against the side of the table. My nipples rubbing around on the rough felt of the table were becoming more sensitive with each stroke. Back and forth you pounded my ass, sometimes slapping my cheeks, sometimes pulling my cheeks apart so you could watch your cock drilling into me. Your balls bounced against my pussy and clit, giving me tiny shocks but not enough contact to let me cum.

My groans were now moans of pleasure. I was enjoying your cock punishing my tender little ass. You were enjoying it too, I could tell. I could feel your cock swelling in my ass. I felt like I was going to split in two and you roughly used me for your own pleasure. With one more violent shove, you slammed your cock fully into my ass and I felt your release. Spurt after spurt of cum filling my ass. You began pumping again as my muscles milked your cum from your cock. Your hands reached up and gripped my breasts squeezing my nipples as you slammed your cock all the way in one last time, holding your cock imbedded until it began to shrink.

You stood up then and I heard a pop when you pulled your cock out of my ass. Reaching into the pocket of your jeans you pulled out my satin panties and wiped your cock off on them. As you pulled your clothes on, I continued to lay on the table edge, ass exposed to all who looked, my hole wide open and you're cum beginning to dribble out. Once you had dressed you pulled my skirt down over my ass and helped me to stand up. My knees weak, I gripped the edge of the table for support.

You gathered up my pool stick and case and my purse and offering me an arm, walked me out into the night. When we reached my car you opened the passenger door for me, kissing my forehead as you helped me in.

"That was great, we'll have to try that one again some time" you smile down at me, then closing my door you walk around and get in to drive us home.

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