Ladies Night Out 42 min read

A brutal fantasy about trampling by multiple women willing to inflict pain and damage.

written by The Penguin
original source of the story was Mistress Destiny's Femdom Forums

Chapter 1

Joe sighed as he thought about the bar where he took a job last month. It was Friday morning and he knew that he would be so busy, too busy to take a break and his boss was a bitch as well. She seemed to dislike him personally.

He always got the worst jobs like cleaning up the restrooms after someone “yacked on the phone or pissed everywhere”. It was a funny thing but the women’s washroom was always dirtier than the men’s. Jana always found something nasty for Joe to do but “what choice do I have?” thought Joe.

I want to go back to school to get my degree so I can get a better job, but this job will have to do for now as I have to pay my own way; dam my sister for using up all the college money. There’s none left for me.

Anyway, I enjoy looking at Jana; she had the biggest boobs and they were perky too, just like a 20 yr old, nice long legs too! And for some reason, Jana always wore high heels even though she was tall. About 6′ without the heels Joe estimated so he always had to look up at her when she ordered him about the bar. For some reason, this always turned him on.

Joe always got a woody when Jana talked down to him and that was frequently! Jana seemed to enjoy doing this to all the staff she always hired people shorter than her except for the doormen, they were huge, real animals. There was even one woman bouncer they called her “spike” about 6′ 3″ a real Amazon type, Joe wasn’t even sure if she was a woman, she was so muscular.

Joe enjoyed Jana talking to him even if it meant getting yelled at as her boobs were at eye level and she stood so close too! Joe always got an eyeful every time and it made it hard to listen to what Jana was saying so he often had to ask her to repeat herself and this always annoyed Jana. They were really nice ta-ta’s, what Joe wouldn’t give to bury his face in Jana’s boobs! Her legs were so long he swore her inside seam was longer than he thought was humanly possible. Those luscious legs, how Joe dreamed of having those wrapped around his head, shuddering at the thought of Jana cracking his neck like a nutcracker with her long muscular legs.”Oh, the possibilities,” he whispered to himself as Joe boarded the number 10 downtown express bus.

Joe passed the time imagining how it would feel being dominated by Jana or just being trampled by the women who got on and off the bus as he rode into town. He kept count of how many women wore shoes that Joe would like to be stepped on by. 40 on average; the record still stood at 95 one summer day, it helped pass the time when Joe was on the bus, plus it was fun too.

Once in a while when the bus is filling up a woman would sit next to Joe and he would sneak a peek at her shoes pretending to look in his bag for a book to read. If Joe had to stand he would try and stand behind some woman with nice shoes on hoping the bus would lurch causing the woman to stumble and step back on to Joe’s foot. Joe always wore soft canvas shoes or flip-flops (in the summer) for maximum feel on the odd occasion he got lucky.

Joe got to the bar early as he knew that Jana would be there just thinking of ways to make him miserable and he was not wrong this time either!
“Joe I need the bathrooms cleaned and then you can take out the trash, and don’t forget to clean the kitchen fat traps too,” she barked while continuing to fill out the day’s food and bar orders. “Yes boss,” Joe said as he shuffled off to the kitchen to get the mops. “Oh, and by the way Joe, we are having a ‘ladies night’ tonight with male strippers so it’s going to be busy and you better not slack off or you will be in trouble,” snarled Jana.

Joe quickly got to work cleaning as he wanted to be finished as soon as possible. When it was “ladies night” the women would pack in and drink large quantities of alcohol and they would tip well too! If he didn’t finish soon enough the other waiters would scoop more customers and he would get smaller tips. One good night would pay for his books for the semester thought Joe as he hurried through his tasks. Joe rested his chin on the mop surveying the cleaning job he had just completed in the woman’s bathroom when something slammed into his arise pushing Joe forward headfirst into the toilets where he landed face first in the toilet water.

Before Joe could take a breath a foot pushed Joes head underwater, Joe struggled but the weight was too much. Just as Joe thought he would suck in water the pressure lifted and a hand grabbed his hair pulling up his head out of the water and wrenched it back twisting Joe’s neck painfully. “Lucky you did an adequate job boy otherwise who knows what you might have swallowed,“ laughed Jana, “Now quit slacking off or else I will make you clean them with your tongue before you go home tonight.”

Joe rubbed his neck as he admired Jana’s arise and legs as she stalked out of the women’s washroom. He had a woody. Her shoes were so nice and worn and she had used them on him too. Joe couldn’t believe what just happened as he dried off his head and went out to the kitchen to clean the fat traps. Joe completed the disgusting task of dredging out the fat traps when he felt someone watching him. Turning around Joe found Jana watching him again. “Just as well for you cause if I had found you goofing off I would have buried your face in that bucket of smelly fat with my foot.” Jana turned on her heel and walked away Joe heard her say: “I was looking forward to stuffing his head in that fat bucket too,” as she walked back into her office.

Joe watched her disappear inside thinking about what Jana had said. “She sure had a mean streak in her,” he thought. “Well, I had better get this finished or I won’t get enough tables to make some good tips tonight.”

Chapter 2

“I’m so bored since I dumped Scott; I need some man action,“ thought Wendy as she looked over the male prospects in the office. “Dan? No, he’s too good looking to be straight. Hmmm, what about John?” eying John Wendy casually walked past pretending to go to the photocopier, as she passed she spotted the new photos of a woman on John’s cubical wall. “Dam looks like some cougar got to John already,” annoyed Wendy stalked over to the copy machine and saw fax come through. “Another junk fax! When will they stop this crap?”

She picked it up to throw into recycling “wait a minute this is just what the doctor ordered, Roosters is having a ladies night – all right!” Free cover for parties over 20 women and the organizer gets four free drinks too! “It just gets better and better.”

Wendy went around the Office whispering to all of the girls “ladies night at Roosters; all of us are going!”

“I’ll go, it sounds like a blast,” they whispered back. They kept it quiet so that the lawyers wouldn’t get wind of it as the firm was very conservative and would frown on this kind of thing. The dress code in the office forbids women wearing pants or casual clothes even on Fridays. Dresses were allowed but they had to be no longer than just below the knee. Sweater sets and suits with skirts and pantyhose were the standard preferred dress style with high heeled dress shoes naturally.

One of the partners even made it known that flat shoes would result in the woman wearing them not getting a good Christmas bonus. All the women knew this and followed the code as the bonuses were substantial, to say the least, even though they secretly resented it. One woman challenged the dress code but she was somehow fired and never got a job at a lawyer’s office again.

Nothing was ever proven to substantiate any claims made by the women either. So they all suffered through it and quietly vowed to somehow get revenge one day. Carol whispered to Wendy: “I’ll call Heather at the Bank and see if she will tell the girls and then we can get together if there’s more of us it will be so much more fun.”

“Let me know how many by 3 pm and I will reserve some tables. We need 20 to be able to reserve there,” Wendy said to Carol as she kept an eye out for the boss, rubbing her hands at the thought of the fun night ahead. “So far you, me Sandy, Susan, Vicki, Jenny, Brenda, Ashley, Diane, Sabrina, and Kelly all want to go.”

“That’s excellent,” commented Carol as she continued to type furiously, “I’ll check back with Heather at the bank on my break to see how she’s doing.”

Heather got off the phone and went around the bank talking quietly to the girls about “ladies night”. She also did not want her boss (an older female sourpuss Doris, that no one liked, even the customers) to find out or she would find a way of stopping them. Jessica, Mary, Joanne, Nicola, Cindy, Alison, Anne, Carman, and Cleo confirmed to Heather that they would go. “For sure,” they said.

Unbeknown Doris overheard the women at lunch talking about tonight when she was in the toilet. Annoyed at not being asked Doris decided to crash their party anyway. Later after lunch, Carol slipped a note to Wendy saying that 10 girls from the bank confirmed that they would come. “That’s just enough,” thought Wendy. She picked up the phone and called the bar: “Can I speak to the manager please?”

A few moments later Jana picked up the phone: “Hello, Jana speaking.” Wendy talking quietly asked to have enough tables for 24 near the stage. “Sure, no problem. Give me your credit card number to hold the tables and we will waive the cover charge, and your name too. Then I can give your drink tickets to you when you come in the door,” advised Jana as she took the details. ”Great,” said Wendy, “we should be there around 5:30 pm in time for the show at 7 pm.”

“Excellent, oh, and one other thing I neglected to tell you, we will be having a free draw at the end of the night and the prize will be kept secret until then,” said Jana.

“Well, this is getting better and better. Hey, by the way, you sound familiar to me. I knew a Jana Morrison in Collage at Simon Fraser University in 90-92,“ Wendy mentioned as she thought back to her college days. “Wendy French is that you?” screamed Jana excited to run into an old friend.”Yes, yes, it is I’ll catch up with you when we get there. Right now I have to get back to work. The old bastard boss is eying me again,” breathed Wendy as she quickly terminated the call. “Dam,” she thought, “just once I’d like to get back at the partners for the way they treat us, women. It pisses me off that they get away with their chauvinistic old boy’s club ways. It’s just not fair. This dress code and nylons are getting so expensive too; those bastards should have to pay for them, better yet, wear them too. Dam I need a drink. Well, I have to get this report done or I’ll never get out of this hell hole,” she sighed looking at the clock for the fiftieth time.

Just before 5 pm the old codger came out of his office and said: “Wendy, I need this done before you go tonight,” he said as he dropped a file on Wendy’s desk. “Yes sir,” Wendy said looking it over, typing faster than she had ever done. It was just finished at 5 pm. Wendy threw the file back on the old bastards desk as she rushed for the elevator just in time to catch the rest of the girls as they headed out.

Chapter 3

It was almost lunchtime and the kitchen had made egg salad, and ham&cheese sandwiches for the staff. It was such a nice day Joe took his lunch outside to get a real break and went to the back of the parking lot to a small city park nearby. “I can get a little peace and sunshine for 1/2 hr,” he thought to himself as he carried the fresh sandwiches out with him and found a quiet place behind a tree to sit.

”WHERE’S THAT LITTLE BASTARD JOE?” yelled Jana as she stomped around the bar looking for Joe.” I think he went to the park next door,” said Bob not wanting to attract Jana’s anger. Jana looked at him, her eyes narrowing in anger, then turned and stamped out of the bar to find Joe.

Joe was admiring a particularly nice looking young blond with a short skirt and sexy white sandals without looking he reached down to grab another sandwich when he felt a shoe. “Oh sorry I was just reaching for my lunch,” Joe said as he turned around. “Oh, I know you were you pervert and you never had a chance with her, you’re too ugly,“ Jana sneered at him. Joe looked down and saw that Jana had stepped on his sandwiches.

“You’re standing on my sandwiches.”

“Ops,” laughed Jana as she lifted her foot; one sandwich ‘the egg salad sandwich stuck to her sole. “Why don’t you eat the sandwich right off my foot,” asked Jana looking down at Joe. Joe thought: “why not?”

He had always wanted to try it so he bent down and started to eat. Besides: “I’m hungry too.”

“That’s right lick my shoe nice and clean,” said Jana, “you don’t want me mad at you do you, Joe?”

Joe quickly finished licking Jana’s sandal clean tasting the bar floor and street grit and park grass in the process. “Now my other shoe needs cleaning,” she said as she ground her heel into Joe’s ham & cheese sandwich. Joe sighed as he bent down again and started to eater his cheese sandwich off Jana’s heel. “Remember to lick every ounce off the heel, boy. You seem so hungry today. Have you been working hard?“ sarcastically talking down to him as she watched Joe cleans her shoe.

”All clean boss,” said Joe as he finished up. Jana stood on one shoe. Her heel sinking deep into the dirt as she lifted her other shoe up behind her and twisted to examine her sole and heel. “No, you’re not Joe. I can see some left, so keep working at it,” with that she put her shoe down for Joe.

Joe bent right down as the heel was just off the ground and put his tongue way out to get the last bit. Jana watched him and at the right time she slammed her heel down to pin Joe’s tongue to the dirt. “Got you,” laughed Jana, “I always wanted to do that,” she said as she squashed his tongue into the dirt.

Joe was stuck and helpless the pain was debilitating and he could do nothing at all, then relief as Jana lifted up her heel with Joe’s tongue stuck to it: ”See that you are back in 5 mines there’s lots of work to do,” with that Jana ripped her heel off Joe’s tongue and strode back to the bar, her heels sinking into the grass deeply with each step. “Thuken buth tha hert alottt,” Joe tried to say as he scraped the dirt off his swollen and sore tongue.

Joe had just finished his chores and was helping to set up the bar when Jana grabbed him by the arm, “Come with me,” she hissed. He went with her over to the corner: “I have an old college acquaintance of mine coming in with a large group of her friends and I am assigning you to look after them.” Joe nodded not saying anything. “I want you to get them anything they want and don’t screw it up,” Jana looked at him then. “If you screw this up I will fire you and you will never work in a bar again,” she threatened.

Joe swallowed, his mouth suddenly dry: “I won’t make a mistake,” he stammered. “Good, see that you don’t,” Jana then turned on her heel and stomped off barking orders as she went back to her office.

Joe and the other waiters started setting up for the show. Bob looked at Joe and shook his head: “I don’t know why Jana has got it in for you Joe, but I’m glad it’s you and not me.”

Joe kept working but did not say anything as he wanted to be ready in time. The door threw open and Jana came storming out or her office right up to Joe, her breasts almost bumping Joe right in the nose: ”Joe make sure you clean the floor and I want it hand-scrubbed, so on your knees boy, where you belong.”

Joe got out his cleaning bucket and brush and got to work. Bob watched with amusement. “You know it seems that every time she has boyfriend trouble she takes it out on you. You must remind her of her boyfriend you lucky devil.” “Yeah, I just have to keep this job for two more semesters then I should graduate,” Joe said as he stopped to check his work. Joe continued to scrub but he had to rest as it was hard work to clean the grimy floor. He stretched out like a cat putting his hands way out in front and his butt up in the air getting the kinks out of his back staying in this position for a few minutes.

“THUMP” something hard whammed into Joe’s balls, “son of a bitch, what was that?” Joe was thinking as another “THUMP” tossed him forward onto his stomach, his balls protesting the impact, “holy shit that hurt,” gasped Joe as he looked around to the left. His right hand started hurting as he had never felt it before, “what the f….” said Joe wiping his head to the right.

His eyesight was filled with Jana’s sandal right in front of his nose just an inch away, he looked just past her sexy 4″ block heeled strappy platformed sandal to see her other shoe crushing his right hand. “OW, YOU’RE CRUSHING MY HAND,” Joe cried as he watched Jana’s foot and toes whiten as she applied more pressure to crush Joe’s hand. “Well I warned you about goofing off,” sneered Jana. “I caught you again boy. Is there going to be a third-time boy?”

“Ow, ow, ow, ow, no boss, there won’t, please get off my hand or I won’t be able to serve tonight,” Joe cried desperately. “Oh, all right, since you put it like that,” Jana looked down with a smirk on her face as she twisted her foot 90 degrees ensuring maximum pain and putting all of her weight on her foot as she walked off stepping over his head, naturally kicking Joe in the face so he would be distracted and then making sure she stepped on the other hand as Joe was too dazed to see that coming.

Joe felt his skin burn as Jana twisted her foot and his bones crunch then the kick in his face rocked his head causing Joe to blackout for a second, he saw too late, Jana’s left shoe heel come down hard on his left hand. The back edge first, the fingers taking most of the force crushing with so much pain it almost felt like she tried to cut them off with the back of her heel!

“I never thought that would hurt so much,” said Joe under his breath rubbing his hands and head, gasping in pain, while trying to keep working as best he could. Bob looked on in horror at Joe’s crushed hand.

“WELL, LET THAT BE A LESSON TO ALL OF YOU IF YOU GUYS. SLACK OFF JOE’S PUNISHMENT. IT WILL HAPPEN TO YOU TOO IF YOU DON’T WATCH IT,” shouted Jana over the music playing. With that, she kicked Joe so hard in the arse that he fell forward on to his sore hands. Joe yelped as he stopped himself from falling face-first into the dirty bucket. “Clang!” his head hit the side of the bucket and tipped it over spilling the water everywhere. Jana stamped through the water and kicked Joe again in the ribs. “OFFFH,” grunted Joe as he fell on his side. ”Keep making a mess and I will have to punish you some more,” said Jana as she grunted with the effort to kick Joe in the ribs a second-time. “THUMP!”

Joe felt his rib crack. He wasn’t sure but it hurt like when that car ran into him that time. ”I’ll clean up. Please don’t kick me again. Please!”

“Just clean it up,” snapped Jana walking away from Joe. ”Wow, man, I’m amazed at how much you are willing to take from her. You must really need this job,” commented Bob with a grin on his face. ”Just be glad she doesn’t pay attention to you,“ gasped Joe as he cleaned up.

Chapter 4

The rest of the afternoon went by slowly as all of the girls waited impatiently for 5 pm to come. It was a mad dash for the elevators as the high heeled women burst out of the offices and cubical not even stopping to put on their walking shoes. Running to the elevators in their heels all 11 of them eager to get out of the building. All of the girls squeezed into the elevator a sea of pantyhose, skirts, and heels.

“Looks like you just made it,” Carol said to Wendy watching her breathing hard. “Yeah, that bastard boss pulled the old, ‘type this out before you go, it won’t take a minute,’ routine.” “I just hate that it makes you want to smack him one,” replied Carol. “Better yet I imagine kicking the boss in the mouth,” said Wendy. “Since I have been taking kickboxing it has given me a whole new perspective,” she commented as the elevator dropped to the ground.

The express elevator shot down to the street level and they all piled out rushing for the doors. One guy got pushed aside and he cursed at them, “Bitches who you think you are?”

“We would have trampled you if you didn’t move,“ Wendy said over her shoulder as she shot through the entrance and out on to the street in the late sunshine. Like a mob the women quickly walked down the street crushing everything in the way with their shoes; cigarette packs, leaves, juice boxes, pop cans, whatever, it didn’t matter. Some of the women even seemed to go out of their way to step on anything they saw.

In the next block, the women from the bank caught up with the first bunch. Heather saw Wendy and fell in step with her. Walking quickly they chatted back and forth, their heels clicking in time with each other. Soon it was like an army of women marching in high heels down the street. Everyone got out of their way very quickly.

They threw open the doors at Roosters and the doormen waved them through. Everyone was excited as it was Friday night and they heard there was no cover for them. It meant they could have an extra drink or two. Wendy and Heather found their reserved tables and sat down picking the best spot. The girls looked around for the waiters when the Manager came over to speak to Wendy.

Jana hugged Wendy: “It’s been a while since college, but you haven’t changed at all.” “Not too much. I’ve kept in shape with exercise classes. I’m doing the kickboxing class right now,” said Wendy. “That’s a coincidence. I have been doing it for a few years now and have been in a few matches as well. We will have to catch up later. Here are your seats,” Jana indicated to the tables Joe set up, “and Joe will be your waiter for the night. If you have any trouble with him let me know and I’ll fix him.”

“Great,” Wendy said as she looked over Joe. “Get us drinks now boy, on the double,” Joe rushed around taking orders. They were a rowdy bunch, laughing at him, pinching his butt, playing with his hair, but Joe said nothing because it wasn’t worth the trouble and the tips would be good, too. And, he might as well enjoy himself. Joe came back with the drinks for some of the women.

He scanned the crowd looking at the legs and shoes dreaming about how nice it would be to have a girlfriend again. It had been awhile. He breathed deeply as he passed the drinks out enjoying the smell of numerous perfumes and scents around the women. Joe remembered how his last girlfriend had trampled him occasionally when he begged her. It was so good. She always wore heels and he had always helped her pick out her shoes for work and pleasure. He wasn’t allowed to “play” with her work shoes but he had her old shoes and the shoes that she brought from the “goodwill” store for him to “use”. Joe just couldn’t help it he had to use her “work” shoes because they always smelled so great and they were well worn too.

“WHERE’S MY DRINK?” startled Joe back to reality. Joe looked around to see who yelled at him, an attractive blond-haired woman glared at Joe. “WELL, BOY?” Joe replied: “Coming right up miss,” as he looked down at her shoes “God, they were nice 4 in. high black with those new wide heels that were narrow from the side. What I wouldn’t give to have her stomp on my nuts with those shoes here thought.”

As Joe walked away, someone called out: “Heather.” He saw the blond turn and reply. “Ah, so that’s her name, nice name, too.” He had always liked that name. A few minutes later Joe returned and passed out the rest of the drinks and rushed around taking more orders for drinks and food, collecting empties and emptying ashtrays.

He hustled his butt managing always to get glimpses of short skirts, legs, and heels. The women were getting rowdier and rowdier as they drank. Before long Joe had trouble getting some of them to pay for their drinks. He was slipping through the crowd of women taking every opportunity to brush up against them and drink in their scents as he waited on the tables when someone grabbed the drinks off his tray.

“Hey, put that back. I’ll be right with you to take your order,” Joe blurted out as he turned his head to see who had taken the drinks. “Fuck you,” the three women yelled at him in unison. Joe had had enough and he knew that that was the one thing he could get someone kicked out, for not paying for drinks, even Jana would have to agree on this. “I’m going to get the Bouncers right now,” Joe yelled back as he threaded through the women to get to the door.

Chapter 5

“OH, NO YOU’RE NOT,” Wendy yelled. “GET HIM,” and she launched a kick to Joe’s groin with her gold-tipped Nine West 3 in. high heeled pump. Joe felt it slam into his dick and balls and doubled over in pain. From behind another woman kicked him in the back of the knee popping the joint forward, hen another kick, much stronger, by a tall red-haired woman who had a platform sandal on. Joe sank to his knees: “OW, that hurt,” he gasped.

Wendy looked at him in contempt then she smiled: “I have been taking kickboxing for exercise.” She asked: “How does this feel?” as she wound back and buried her pump into Joe’s stomach. All Joe could do is cough and gasp for air as he doubled over in pain. Slowly he realized he was resting his face on Wendy’s pumps smelling in her heavenly scent with every breath.

“GET YOUR PATHETIC FACE OFF MY SHOES!” she screamed at him. Joe turned his head looking for the sound, dazed and confused he struggled to orient himself. He rolled over onto his back and sat up, slowly. All Joe could see was female legs, delicious pantyhose covered legs and high heels shoes, sandals, pumps, slingbacks, d’Orsay pumps, court shoes, Mary Jane’s and some knee-length boots as well. Joe thought he had died and was in heaven.

“Let’s get him,” Joe heard someone say. Hands grabbed at him ripping his shirt off. Joe saw a court shoe swing towards him, too late. Joe tried to avoid it but it still kicked him in the face. Joe saw stars as his head snapped back.

When he came to he was surrounded with shoes pressing closely. His legs felt cold so he lifted his head slightly and saw that his pants, socks, and shoes had been removed. He could hear women talking above him but not exactly what they were saying: “ex-boyfriend…….. Ex-husband………. bastard cheated….. fu…boss I hate that bastard…….. Ever had an under….. heels.” Then they all turned to face him. Joe could sense the hostility from some of the women. “This is what I’d like to do to my lazy husband,” exclaimed Susan. With that, she drew her high heeled boot back, way back.

Just in time, Joe managed to look up to see Susan standing between his open legs, swinging her foot forward as she stepped forward (as if she was kicking a football a free-kick as it were). Joe tried to cover with his hands but they were tangled around the ladies legs and he was a little too late! Susan’s stiletto-heeled boot slammed into Joe’s balls and the base of his dick so hard he moved back almost a foot on the bar floor. Joe fell back and let out a shout. As he opened his mouth to scream Jenny shoved her well worn white rectangular 4 in. high heeled pump deep into Joe’s mouth to stifle his scream.

“That should keep the little bastard quiet,” sneered Jenny looking down at him. She leaned on her heel until Joe stopped making all sounds except for choking noises. “Ease up a little, we don’t want to finish him off too soon,” Wendy cautioned Jenny. “Ok, but just remember I get to stomp on his head when we are finished with him,” Jenny eased up on her leg and shifted her weight a little so Joe could breathe again. “Let’s do a conga line,” suggested Susan. “I’ll go first,“ with that she stepped up onto Joe’s groin sinking her heel into his balls.

Joe gasped in pain as Susan squished his balls and dick then she shuffled forward and then Heather stepped up on Joe’s dick with her 4-inch high heeled black patent pumps giggling as she did, “I’ve always wanted to do this. I hope I don’t hurt you,” she said as she looked down at Joe grunted as he was busy trying to withstand Susan’s stiletto-heeled boots. Wendy followed next as all the women moved forward. Joe gave up resisting as Susan stepped off his face. Wendy marched across Joe digging her heels in as she went. Kelly stepped up next: “This is what I’d like to do to my boss,” she said targeting Joe’s dick with her worn office pump, slowly pressing down on the base, lifting up her other shoe so that the full weight was driving her heel into Joe’s pelvic bone.

Joe could only gurgle around Jenny’s heel. Pressing his tongue down, his eyes bulging in pain. Kelly then placed her other heel into Joe’s stomach. Again, with full weight on one foot. Jenny commented: “You are good. Did you have dance lessons?” “Ballet actually,” replied Kelly. Diane looked carefully then steadied herself and leaped into the air landing both pearlized pointed toe high heeled pumps directly on Joe’s groin. The 3-inch narrow heels slamming into Joe so hard he thought they had gone completely through him and hit the floor.

Joe screamed as best as he could,  but the music was a little too loud and Jenny saw what was coming and pressed down in anticipation muffling Joe enough. Diane waited for the girls to move forward and then jumped up again landing on Joe’s stomach pounding her heels down through his stomach. And then another hop on to his chest sinking Joe’s chest allot as she was a little “big-boned.” Laughing down at Joe, Diane chuckled: “I sure wish you were my boss ’cause I would jump up and down for each time he was mean to me and that would take all night.” Cindy looked down: “Well now he took Diane’s jumps so I’ll be ok to do a stampede.”

With that, she proceeded to step up on Joe’s tenderized groin with her black patent slingback pumps with a nasty stiletto heel. Once she was settled on Joe’s groin Cindy started jackhammering Joe, as she slowly walked up his body, each foot moving forward an inch all the way up to his neck. Joe suffered in continued agony with each stiletto heel step. ”My girlfriend never caused this much pain,” he thought as he suffered through Cindy’s relentless hammering. Then Nichol stepped onto Joe’s balls with her wide 4-inch heeled oxford pump.

Joe gasped in pain as he felt his nuts squish. Wow, that’s a big heel, it got both of them. He cried as tears came out when Nichol’s full weight pressed down, then relief as she stepped forward onto his stomach. It was a holiday as she walked on Joe and stepped off his face. “I always wanted to do that,” Nichol laughed. Joe was too tired to look up to see how many were left to walk on him. It seemed endless as each woman stomped on his dick after saying how much they wish he was their “husband, ex-husband, boss, ex-boyfriend, etc.

With each trample, the women made sure Joe felt their heels digging in painfully as they stomped their way across him. Finally, it was Sabrina’s turn. She rubbed her hands together in anticipation tilting her shoe to the side to check her heel. “Nice these will do some damage,” Sabrina said looking down at the worn but sharp 4-inch high square gold metal heel on her cream-colored Nine West pumps. “I can’t wait to see what kind of mark these babies will leave on him. I only wish he was my cheating ex-husband. Then I would really work him over. Oh, well, you can’t have everything.”

Sabrina carefully placed her heel right on Joe’s left ball pressing down until she saw Joe flinch. “Just right, now to step up with the other one.” Joe gasped with renewed pain this hurt so much more than the others, it woke him right up. Joe tried to see but Jenny’s heel pressed down in his mouth and Joe gave up, it was no use. Sabrina bounced up and down on her heels harder and harder until looking down she spotted blood. “Nice.”

Then she stepped forward lifting her heel. The skin stuck to it ripping off at the last second as it stretched up standing on Joe’s stomach. With Heather helping her, Sabrina lifted her heel up behind her, the other sinking deep into Joe’s badly bruised stomach. Sabrina inspected her heel: “Yep, there’s blood on my heel. All right.” Then Sabrina stepped down and lifted the other heel and confirmed blood was on the other as well. Looking down Sabrina saw blood pooling around her heels. “Oh, you poor man,” she said sarcastically as she marched very slowly up Joe’s body cutting his skin with each step, letting the blood seep out around her heels.

Joe cried out with each step. It hurt so much more than Joe could have ever imagined. Then, all Joe could see was Sabrina’s heel right above his eye. Abruptly it moved forward a little. Joe looked up as much above his head as he could, he could just see Sabrina’s heel lowering down to his forehead. Joe tensed up. He knew what was coming. Her heel pressed down on Joe’s forehead slowly increasing the pressure. Joe waited for the blood to flow as he felt Sabrina’s square heel cut its way into his head.

Sabrina stood on her right heel pushing down on her heel as hard as she could: “I’m marking this one as mine.” She grunted, looking down as blood started to flow. Lifting her heel she saw it had cut into Joe’s head a perfect square. “Now your mine boy,” she laughed at Joe, dragging her heels across Joe’s stomach to wipe the blood off.

Joe just lay there too exhausted to resist. Pain all over his body throbbing with each heartbeat. Jenny saw that he was broken so she took her heel out of Joe’s mouth and just stood over Joe. Her shoes either side of Joes head continuing to drink, eat and chat with the women standing around Joe. Then Joe slowly pulled his legs up to his chest to help ease the pain; a taller woman looking down on Joe smiled at him and then started rubbing her wine red patent slingback pump on his body.

Joe looked at her in surprise: “You aren’t going to trample me like the rest of them?” he asked cautiously wheezing with each breath. “No, not at all,” replied Jessica, ”I like doing this, my old boyfriend had a foot fetish and enjoyed this.” Joe slowly let his legs down as he enjoyed the shoe massage he got harder and harder, his sore dick twitching with each swing of her shoe. Jessica started rubbing his sore dick up and down, her heel catching his ball sack each time giving just the right amount of pain. Jessica looked down at Joe and smiled as she rubbed her shoe back and forth, back and forth in a good rhythm. Joe tried to hold on as long as he could, mesmerized by Jessica’s shoe and leg swinging forward and back her wide heel, narrow from the side, scraping his balls forward and back like a grandfather clock pendulum swinging. They were quite new Joe could tell with a little wear but in very good condition with the heels still sharp enough to stimulate him.

At last, Joe couldn’t hold any longer he squirted everywhere some juice even went past Joe’s head. Jessica pressed down on Joe hard with her slingback pump rubbing harder causing Joe to shudder again when Jessica released the pressure from her shoe. Joe squirted again making another mess everywhere. After Joe recovered he looked around to see where his cum went. He soon found it on the calves of one woman and the front of another woman’s shoe! Joe thought he had seen that shoe before then it dawned on him who it belonged to. It was Jana’s sandal!

Chapter 6

Not good! Thought Joe he looked up to see if she had noticed. Jana was looking down at him and Joe could tell she was angrier than he had ever seen her.


Joe quickly cleaned her foot secretly enjoying the taste of her high heeled block heel sandal. “Now get up, get dressed and get back to work! I will deal with you later you piece of shit.” Joe looked around for his shirt and pants, hurriedly getting dressed. The women surrounded him while he was doing this.

“We haven’t finished with you yet,” Wendy and Jessica told him. “Yeah, I haven’t stomped on your head yet, and I can’t wait!” chimed in Jenny. Joe limped away still hurting from the kicks he got and went to the employee’s bathroom to finish cleaning up. Joe found his spare shirt, wincing as he put it on, from the cuts and bruises inflicted by the women.

He looked down and saw that the cuts that Jessica had made with her sharp heels had stopped bleeding. Touching them gingerly Joe recalled the incredible pain she caused while making the cuts, how that hurt! Joe quickly finished cleaning up and hurried out to continue working.

Warier Joe hustled around the tables serving drinks and food as the women in the bar anticipated the show was drawing near. The drinking was quick and Joe could hardly keep up with demand. The women consumed more booze than Joe thought possible. Joe looked up once in a while to the bar area and Jana was always watching him frowning and stomping her shoe when she saw him looking at her. Joe knew he was going to get it good from Jana when the bar closed. Well, he might as well make some money either way.

The show was starting and the first stripper came out. The woman went wild screaming and jumping up and down. Joe stopped and watched the women. “I never thought they would weigh so much and the shoes could hurt so much,” Joe was so mesmerized by the sight and his thoughts he never saw the kick coming. All he felt before he lost consciousness was a heavy blow to the temple.

Joe fell to the ground face down and was unconscious. “Well that was a really good kick Jana,” admired Wendy. “He deserves it, the lazy shit,” Jana said as she casually stepped on Joe’s hand grinding her foot and feeling the hand and fingers crunch underneath her sandal as she twisted her foot back and forth.

“I’ve been taking kickboxing for a couple of years now and I really enjoy it.” “Wow small world after all,” said Wendy looking down at Joe’s motionless form, “I have just started lessons myself. We should get together so I can learn how to kick like you. I mean, you really laid him out cold, see,” thump! Wendy landed her gold-tipped black pump on the side of Joe’s face, gouging his cheek with her heel, “he didn’t even wake up.”

“Well if I was him I wouldn’t want to lay there for long with these drunken women around. They will grind him into pulp,” said Jana looking around at the excited women.

Vicki stood up on her toes trying to see the strippers, “I can’t see even with my heels on,” she complained to Brenda standing beside her. Brenda looked around, “you must be about 5ft tall. Why don’t you stand on Joe he won’t mind. He’s passed out anyway.”

“Good idea. Help me up, will you?” replied Vicki with that she placed her navy blue pump heel right on Joe’s chest grunting as she pushed down with her pump. “That’s so much better,” exclaimed Vicki tapping Ashley on the shoulder, “come up here you can see much better.”

Ashley looked over then using Vickie to help she put her black patent platform sandal up on Joe’s stomach and stepped up. “It’s a little unstable, but I can see so much better,” replied Ashley digging her heels into Joe’s stomach, trying to anchor herself better. Stacy stumbled as she came back from the washroom, “what the fuck I’m not that drunk yet. What the hell is that waiter doing down there? He’s going to be sorry in the morning,” Stacy said out loud to no one in particular, tapping Ashley on the arm. “Help me up, will you? It’s hard to see,” asked Stacy as she placed one size 6 worn 3-inch wide heeled black office pump on Joe’s groin grunting as she stepped up on Joe .”That’s better. Thanks, Ashley,” said Stacy as she admired the strippers.

Cleo looked behind her to see who had their hand on her shoulder. ”That’s odd. I thought Ashley was shorter, allot shorter. Ah, ha, our little waiter is passed out on the floor! Well, he will be sorry when he wakes up. No, I take that back, if he wakes up!” Just for fun, Cleo amused herself grinding her white narrow heeled sandal into Joe’s head admiring the way her heel cut into Joes face leaving welts and cuts as she systematically ground up Joes entire head. Cleo watched the strippers while doing this, but she wasn’t into them at all. It was fun to be out anyway, looking down to survey the damage Cleo saw that Joe was bleeding from numerous cuts all over her shoe.

“Oops looks like that’s going to hurt. Dam there’s blood all over my new shoes,” said Cleo to herself. She dragged her shoe over Joe’s chest where ever she could find a spot, wiping the blood off her heel, ripping his shirt a little. “Help, help me” but no one heard the cry it was too noisy.

Chapter 7

Joe struggled to get the air. He opened his eyes to find a shoe grinding its heel into his cheek. “AHHH, that hurts,” he gasped. “Please stop it,” he cried. The heel stopped and lifted off. Ah, relief. Then the heel stabbed Joe’s face again an inch over. Joe’s cheek flooded with pain again as the heel ground its way in cutting his cheek again.

No one heard him over the music and women screaming. Joe resigned himself to the pain. Again relief than another stab by the sexy 4-inch heel. It seemed that the pain would never end. Then, the relief as the heel was lifted time after time. Joe felt his head bleed everywhere. He saw the heel soaked in blood and the sole too. At last, it stopped then Joe saw the woman looking down at him.

“Help me,” he cried. She saw him then she looked at her shoe turning it to the side, then she wiped it on his shirt. Once the white sandal was clean she bent down to get a closer look at Joe’s face. “Wow, my shoe really cut your face up harshly,” she commented examining Joe’s face.

“Help me I can hardly breathe at all,” gasped Joe. Cleo smiled at him and laughed, “I’ll help you boy .” With that, she stood up and tapped Ashley, Vicki, and Stacy on the arms. ”Your footstool is awake and he wants me to tell you three you’re all too fat to stand on him and you’re asses are really big too!”

Ashley looked at Stacy and Vicki in surprise. They looked back at her and each other then down at Joe. A tear formed in Vickie’s eye. The three women leaned in close. “Well, that’s just mean,” Ashley said. “Let’s get even,” growled Stacy. They talked a little more. Joe struggled for air. The weight of the three women was crushing him and exhausting him and he didn’t think he could last much longer.

“1 … 2 … 3 …. Jump,” they cried. Ashley, Stacy, and Vicki jumped up their heels driving deep into Joe’s flesh as they lept into the air slamming down stiff-legged. Their heels sank deeper into Joe. “Again 1… 2…. 3… Jump,” up the women went once more slamming their heels into Joe’s body. Joe cried out with each jump, weaker and weaker cries with each one.

He felt his ribs crack every time Vicki’s navy blue pumps’ heels pounded into his chest. Ashley was squishing his stomach so much Joe thought that her platform sandal heels were impacting his spine. She was driving her heels in so deep. Joe’s dick exploded in pain after the second jump from Stacy drove her wide 3-inch worn black office pumps into his nuts again and again. With each jump Stacy’s wide heels found their mark alternating between his nut sack and his dick with each jump.

Joe started crying from the pain it was too much for him. Cleo watched in fascination as the three women jumped up and down ten times. She bent down to get a good close look at Joe and started laughing when he cried from the pain. “I only wish you were my ex-husband. Oh well, you can’t have everything,” she chuckled and stood up then stamped on Joe’s face neatly twisting her foot and walked away laughing.

“How’s that for weight, you bastard, are we too heavy now?” asked Vicki bending down to get a closer look at Joe’s face. “Oh, no! It looks like Cleo marked up your face a little,“ Vicki tapped Joe’s face with her pump smearing the blood around then she cleaned her pump off on his shirt.

Joe looked up at Vicki trying to say something but nothing would come out. His eyes closed and he just lay there completely exhausted too weak to do or say anything. Joes’ shirt was ripped to shreds and the women’s heels had cut into Joes’ flesh everywhere; blood seeped from the cuts and onto the women’s shoes. “Aw, look, we made him bleed,” said Stacy.

They all looked down at Joe. “I bet that hurts a lot,” commented Stacy tapping some of the cuts with the toe of her scuffed up pump.”

“Quick. We’re missing the grand finale,” Ashley stood up quickly so she wouldn’t miss anything. Joe just lay there looking at the women standing on him wondering when he was going to escape the misery they were putting him through.


3 thoughts on “Ladies Night Out 42 min read

  1. Wow that’s all I can say what a wonderful story. Please keep up the good work I don’t know if these are women writing the stories for guys but I sure hope it is the women writing the stories thank you James

    1. Thank you for your comment, James. The author is The Pinguin and I am almost certain that The Pinguin is a male writer. Anyway, this story, like many others here was written over 20 years ago on a discussion board that does not exist anymore. If I find any more of his stories I’ll be adding it here to the collection.

  2. That was awesome,but i’m more into barefeet. It probably would’ve made me cum as i was reading if they would have taken the liberty of stepping out of their shoes and doing all the rest. Still excellent work.

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