Gurl Story

“This one right here” Max said. “This little sissy is perfect!” Max and his two friends had spent the last few weeks scouring Craigslist personal ads for a small crossdressing sissy that they could take advantage of in the back room at Max’s dive bar. “I’ll email the cunt with a few pics of my nine-inch cock – see if she bites!” he bragged to his friends. Sure enough, two hours later, the CD named Holly liked and commented on Max’s pictures. Throughout the day Max and Holly swopped information and emailed each other, then Holly decided to send Max pictures that he wanted (face, her little sissy cock, ass and bending over with a butt plug). Max emailed the pictures the little crossdressing faggot to his buddies and wrote - “Look! – this sissy could pass easily, and even has little tits like a real chick! Oh, shit this is gonna be fun!” The guys all agreed that Holly was to be the one.

Holly had said in her last email that she would be available that night, and that was perfect for Max and his buddies. Max, told her the name of a bar that would be a safe place to meet and told her it was a quiet out of the way place and wouldn’t be too busy. But he knew all the regular pervs would be there watching porn on some of the monitors. Most of the people in that neighborhood avoided his sleazy bar, especially the women, knowing extremely hardcore porn was playing, and hearing of the disgusting things that took place there. It was a small, dirty below ground bar and the business above the bar had been closed for years, but stupidly she believed Max when he said it was safe.

Holly arrived right on time not wanting to be late for her date with Max, but she also had a can of mace in her purse, just in case. She wore wearing a cute velvet thigh-length black dress with cute purple top, long black stockings and black heels. Max asked her to wear her long red hair curly, so she did. She hesitated as she looked down at the dumpy bar, took a deep breath then double-checked her purse to make sure the can of mace was full. This was a big step for Holly; meeting a stranger here but his pictures and what he wrote in his emails were so hot and she thought she was ready, and walked down the concrete stairs. Stopping at the door she tried to calm the butterflies in her stomach and warning signs all around her. When she opened the door, she noticed the dimly lit bar only had a few people inside, all men of various ages and stages of intoxication. Just before she had a chance to reconsider her agreement to meet Max here, the bartender asked, “Can I help you, hon?” “I…I’m just looking for a friend that was going to meet me here.” “Oh, you must be Holly,” extending his hand “I’m Jake…Max should be here in a couple of minutes” “You know Max? Holly asked. “Yep, this is his place” Jake responded. “Have a seat and let me get ya a drink!” As Holly walked over to where Jake motioned her to, she could feel eyes undressing her. “Don’t mind them, it’s not often we get real lookers in here” he halfway laughed. “And don’t you worry none, you’re safe here.” Holly was started her Bacardi and Coke (very heavy on the Bacardi) when Max and two other guys walked in.

Max immediately recognized Holly, and she looked just like the pictures she sent him. “Damn she’s or he is hot!” he whispered to his friends. Holly turned on her bar stool and watched the men approach. “Hey Holly!” Max exclaimed. “You made it, great. Well this is this is Paul and Jon, and I believe you already know Jake my bartender.” Once introductions were made, Max stepped back, eyeing Holly. “Damn, I can’t believe you are not a real woman” Holly couldn’t believe he said that out loud, in front of everyone. “MAX!!!” Holly squealed. Max explained to her that his close friends knew what he preferred sexually, and they wanted to meet her after seeing her pictures. Holly turned beet red knowing Max shared the pictures for his eyes only with his friends. Holly looked at the bartender and ordered a double Bacardi with no ice to escape the embarrassing humiliation revelation.

“But, if it makes a difference, they all think you are gorgeous baby” That comment from Max brought a smile to her face. Then he put his hands on her shoulders and told her she was the prettiest girl in the whole bar. Again, knowing there were zero women in the bar, Holly chuckled. Max continued to make jokes; and between the alcohol, Max’s and his friends compliments, Holly felt more comfortable and Jake kept the Bacardi flowing. Max stepped up to Holly, hiking her dress up so that the lacy stocking tops were visible, and said quietly in her ear “You and I are gonna have some fun tonight.” Another warning that went over her head.

Stepping back, Max pulled Holly off the bar stool and led her over to the pool tables. He continued “How about we play a little pool, you bending over in that dress is going to be the best thing this place has seen in years” “And when the boys see those sexy legs, I’m going to have to fight’em off” he joked. “Come on babe, it’ll be fun…and I will make sure the guys don’t get too rowdy…promise.” That was all Holly needed, coupled with the confidence builder of her fourth drink (two doubles) and in her buzzed state. Not thinking, she asked Jake to put her purse behind the bar. Jake took her purse with one hand and offered her yet another drink with the other. As Holly accepted the drink from Jake, Max whispered to his other friend “When this little cunt starts playing pool and bends over for a shot, the guys will be able to see all of those nice sissy legs and cute little ass. That’ll turn them on!!” As soon as the game began, all eyes were on Holly – watching her bend over as she took shot after shot; each ending in a miss after miss. Max’s plan was working. Every time Holly bent over, the guys were telling her to take another shot, so they could see more of her backside.

Max looked around and saw one of the drunks in the bar was actually whacking off underneath a table. Looking at her bend over the pool table, Max proclaimed loudly, “CAN YOU FUCKS BELIEVE THAT IS A FUCKING GUY?!” with a huge grin. The bar got quiet. Holly continued to shoot at the pool balls, oblivious to what was happening around her. One of the guys stood behind Holly, putting his hand up her short dress, in mid-shot. She turned around to see what was going on, but he lifted it anyway saying “Man, I can’t believe they you’re not really a girl!” Then after rubbing the crotch of her panties shouted, “This bitch has got nuts?!“Then another voice said “Hell, anything that looks that good in a dress is a bitch to me!” Max told Holly to put down the pool cue for a minute and he grabbed her by the shoulders and turned Holly’s back to the group of men. Lifting she dress up over her waist and saying. “Now I ask you gentlemen, is this not an ass that was made for fucking?” The small crowd observing her sexy shapely pale ass in those white flowery silk panties made so many comments about how pretty and feminine she looked, it was a shame she mistook the group’s lust for a juicy white ass for adoration. The men whistled and hollered. Holly blushed and pulled her dress back down; then resumed her game of pool. She felt like the sexiest woman on the planet.

Then the feeling came crashing down. Holly, even in her heels had to scooch over the table to make a shot. Seeing her leaning over the table, with that nice ass in the air, and one foot off the floor was the breaking point. As she was lining up her shot, she was suddenly pushed down on her stomach and held her in place over the pool table by strong beefy hands. Someone took her pool stick and she was told “Don’t move” From behind. Her short velvet black dress was hiked up over her back; and her panties were snatched down revealing her nice round pale ass to the crowd. Holly did her best to push down up her dress, but her arms were grabbed and pulled across the table. There were simply too many guys to fight off! Even in her sloshed and befuddled mind, she kept thinking “WHAT IS HAPPENING?!” Holly struggled to get away, but her attempts were met with just being pushed down harder. Her heart sank further when she saw Max, just sitting there enjoying his beer and watching the show. “Spread the whore’s legs!” came a husky, wheezy voice from behind her. The men laughed, but Holly wanted to scream; but a sticky hand covered her mouth.

She heard the group of intoxicated men whistle and make humiliating comments. Over the roar of the excited men that surrounded her; she heard Jake the bartender announced to the crowd that he put up the “Bar Is Closed” sign, and the rowdy room got even louder. It was a lonely underground dive bar surrounded by a bunch of closed businesses on a slow night. There was not cavalry coming to the rescue.

Next, Holly hands slap and grope her ass, her balls and sissy cock. An old toothless guy that smelled like vomit, licked two fingers and jammed them as far up her asscunt as his fingers would go while repeating “You like this, don’t ya, little faggot?” He enjoyed the tightness of her anal ring squeezing, trying to expel his dirty digits, and of course her reaction to what he was doing to her. Holly kept calling out for Max, even with the hand over her mouth; but hands continued to probe everywhere underneath her. Her ass and sissy balls were slapped, pulled, someone was trying to jackoff her small limp clitty as she did her best to fight to break free. Then what she feared happened, she was saving gift for Max if their date went the way she wanted. She felt the first cock enter her upturned ass. She wiggled to avoid the unknown cock from entering her but it was futile. She lost it and started to weep openly, and with that, Jake turned up the volume on the jukebox. Just as the cock in her was coming, she felt him withdraw then warm liquid paint her asshole, pale cheeks and balls. The old vomit-smelling man asked if she liked it, and someone grabbed a handful of Holly’s red hair and nodded her head “yes” for the cheering horde. Max, finally stood up, telling the old man “I told you I would get you a piece of ass Carl, now fork over the cash!” Carl happily gave him a $50 and said, “That was the best pussy I had in 20 years” then Max said, ‘That was the ONLY pussy you had in 20 years, and the crowd burst into laughter.

Max told the guys holding her down to let her go, then Holly immediately jumped up, pulled down her dress over her sticky ass and ran to Max wrapping her arms around him and whispered “Thank you” like he was her savior as she held him tight. Max groped Holly’s ass then push her to arm’s length. “Pull down your top, sissy. Let the boys see your cute little boobies!” Holly had a surprised and confused look on her face. “Open your top, or I’ll do it for you!” Max said. Her eyes were already red and mascara streaking from her ordeal over the pool table as fresh tears streamed down her cheeks. She unbuttoned her top as ordered to the cat-calls of the disgusting men, the while time mouthing “I want to go home.” When she was finished, she pulled off her black, lacy bra, allowing her little pert, 36A, breast to pop out. There were cheers from all of the guys. One guy said “Hell, that definitely is not a dude!” Max took Holly’s hand and started to lead her to the back room, stating “Lets you and me go have some fun, cunt!” They got to the back- room door; and Max told her to wait there a second. She stood silently as the tears flowed, and wondered why she was so stupid. As her head began to clear, she thought about the mace in her purse and her shoulders dropped, remembering giving her purse to Jake. Max went back to the pool room, and told the group of horny men “Let me show you how to fuck pussy!” as the small crowd followed, he returned to Holly waiting for him.

Max returned to where Holly was standing, grasped her hand and walked into the back room. His hands went from her shoulders then to Holly’s gentle perky boobs; he gently massaged them. She stood still and emotionless when he started pulling on them like he was trying to milk a cow. “Umm, I just love these boobies bitch! He said.” He grabbed the boobs and pulled down. “Get my big cock ready for your faggot cunt!” Max said. Holly, wanting to home again, went to her knees and took Max’s hardening cock into her mouth. “That’s it baby! Make it grow, so I can fuck you good!” He said. Holly sucked his cock deeply into her mouth, but it wasn’t deep enough for Max. He held her head and pushed into her throat. Holly gagged but the gagging just let Max in deeper. He liked how her gagging throat gripped his shaft. Holly struggled and then Max pulled leaving a stream of gagged up puke bridging across her mouth, and his slicked-up monster. “Good job slut!” he said. “Now let’s try out that pussy”.

There was an old bed with a nasty, stained mattress. Max grabbed Holly by the back of her hair and planted her on all 4’s, with her knees on the edge of the bed. He spread her sissy legs far apart and stepped in between them. Holly’s throat provided all the lube his nine-inch, uncut throbbing cock needed. Placing the head of his cock against her rectum, Max said “If you aint a woman now, you soon will be!” Grabbing Holly’s hips, he thrust the entire length of his cock into her, all at once. Her scream could be heard in the barroom over the music of the jukebox. Max was grinding so hard, his hairy crotch felt like sandpaper against her smooth, rounded ass. “That’s it baby! Open up for Daddy!” Max exclaimed! Holly whimpered as Max let his entire length nestle in her bowels; letting her feel each time his cock pulsed.

Max started fucking. Long, deliberate strokes. Holly’s tried her best to take Max in her asscunt but this ordeal and abuse just made her want to puke up everything in her stomach. “Man, that cunt takes a cock better than any woman I know!” “Bitch, if you had any man left in you went you got here, it will be gone by the time we finish with you!” Max picked up the pace and in a few minutes, he was ready to cum. ‘Cmon, sissy, take Daddy’s sperm!” he exclaimed while drilling deep in her a last time and ejaculated his load into Holly’s ass cunt. Holly whimpered and was almost relieved as she felt his cock pump sperm in her butthole. Before he pulled his greasy cock out, he yelled at the group, some with their cocks already out “WHO’S NEXT!” “Oh no…” she thought.

Her mind went someplace far away with shame as she continued to be victimized and videoed. Max said “Now, stay in that position” Max barked as he used her ass cheek to wipe the crap off his cock. Spent cum dribbled out her open asscunt down to the mattress. As soon as he stepped away, Jon stepped up and shoved his cock into her. “We gonna pull a train on you, sissy whore!” he said. Holly moaned and openly sobbed again. She realized, too late, she was going to have to take them all, and she didn’t have a choice. “I love fucking ass!” Jon exclaimed and he pistoned his cock in and out of Holly’s opened-up pussy. Once Jon had finished, another took his place. As soon as one cock empties its load or played tart practice with her ass and balls, it was replaced by another, and another. Holly’s arms grew weak and she laid her head down on the mattress, her ass way up in the air. She had lost count of the number cocks that had deposited their loads into her. The last guy fucked her as he was drinking a beer. When he pulled out, he shoved the neck of his beer bottle into Holly’s worn out asscunt. “Enjoy my beer, faggot!” he said laughing; and then the room was empty. Holly was too exhausted and overwhelmed to move her body an inch. She lied on the dirty bed, the entire bottom-half of her body was wet from the cum of a dozen men with a beer bottle stuck up her sore sissy cunt.

Back in the bar, the guys were trading stories, laughing at what they had done to the sissy when, they hear a pounding at the door. “Can’t you fucking read, the bar is closed!” yelled Jake the bartender. “It’s me asshole!” the voice yelled back. “Sorry Bear…” Jake quickly jumped up and opened the door for him.

They call him Bear because he is built like one; 325 pounds and tough as nails. Long black hair, full beard and body hair that you could braid. “Where is she?” Bear asked. The guys filled him in on the evening’s party favor. “So, that sissy bitch is still back there?” he asked. Max replied, “Where the fuck is she going to go?!” “Well, y’all aint gonna have all the fun” as he strode to the back room. Jon exclaimed “The cunt is in for it now!” then grabbed another beer.

Finding the strength, Holly had rolled over onto her side and removed the beer bottle, her body weak and tired from the abuse. Trying to collect herself, she was startled to see a monster of a man leering at her from the doorway. It was Bear. “When they bring bitches in here, I’m usually first!” he said.” “My, you are a cute little thing, aren’t you?” Bear went to the edge of the bed and grabbed her ankles and forcefully and rolled her onto her back. “You had boys fucking you, now you’re gonna see what a man can do!” he exclaimed. He pulled Holly so that her ass was right at the edge of the bed. Holly got a scared look on her face as she viewed Bears monster cock. Beer-can thick with a huge mushroomed head and probably a foot long. Bear held Holly’s girly legs high, just below her heels as he positioned his cock against her swollen red asshole. He pulled Holly toward him, then pushed deep. He was all the way in and Holly is speechless. She gasps. Her insides had no choice but to open up as Bear buried himself into her. “Oh yeah!” Bear says. “This asshole is for me!” Bear started fucking her hard. Holly’s asscunt was stretched to the maximum, being destroyed by the invading bear meat. Bear horse cock blew out what was left of her pretty little ass. Pulling almost the full way out, then slamming in balls deep. With no heart, Bear looks down at his crying little victim, makeup smeared, nose running and long black mascara streaks on her pale read face “I’m gonna breed you, sissy slut!” Bear says has he picks up the pace a bit. The bed banged against the walls and squeaked louder than an old car. Holly’s mouth was opened but nothing would come out except the occasional “Awwwwww” She wondered if she would ever shit or walk right again.

Bears was driving harder and grunting like an animal, Holly felt like she had an arm up her asshole, Bear was like a machine with no “off” switch totally ruining her asscunt. In and out the vicious machine pumped and growled. Bear smiled and said, “Yeah bitch this is what it feels like to have a man’s cock in you!” Thrust, spurt, thrust, spurt. Holly moaned, and her legs shook as she finally got out one word “DADDY!!!!” Bear didn’t know if she was crying, having an orgasm or both. Now his powerful legs just kept pumping cock in her. “Take Daddy’s sperm, you little pussy!” Bear said between grunts as he buried himself deep in Holly’s guts, then his full nuts released Bear’s seed. “Oh yeah, baby, take Daddy’s cum deep in your ass bitch!” Bear exclaims as he finished pumping Holly full of his gooey white semen. Bear pulled out of Holly’s abused asscunt and his sperm (and some other fluids) flowed out her gaping hole. Holly reached back with both hands to inspect the damage, unable to close her legs. Bear, still uncaring, got on the bed, kneeling next to Holly’s face. “Now, clean Daddy’s cock, bitch!” He says as he presents this cock to her mouth. Holly, looking at the still huge slimy weapon that opened her up like a can-opener almost shook her head no. It was covered with mucus, cum and what he had fucked out of her. It only took a glare from Bear for a weary Holly to do as told. She took the limp fluid-covered cock in her mouth. Holly pulled back for a second, and sadly looked at him with her big blue eyes and said, “But it tastes like ass…” “Better get used to it bitch!” Bear snored back and pushed it back down her throat. After Bear was satisfied with how she cleaned the remaining slime from his cock, he hopped off the bed and left her there with a ring of slime around her mouth, and bits drooling down her chin. When he left the room, Holly returning to inspecting her gaping butthole.

Bear joined the other men at the pool table. Max jokingly asked, “Jez, with all that screaming is that sissy still alive?” They all laugh. Bear offhandedly said, “That little sissy can really take a cock! I think I have found me a new girlfriend!”