HOW HIGH HEELS by Debra Darling



Have you ever wondered what it might be like to stand in a pair of women’s shoes for several hours? If you ever tried it, you would know what was going through Donna’s mind right now. She had just spent the last two hours balancing herself on her toes as she stood in a pair of pumps with six inch high heels.


The evening had begun as a lark. Jim, who often dressed up as a girl and called himself Donna had met up with Stephanie and taken her to the weekend party of the KC group. Stephanie had expressed an interest in B and D at the last crossdresser’s meeting, and Donna had offered to escort her to a meeting of like-minded people.


Donna had dressed in a red outfit for the evening and then set out to meet Stephanie. She had started with a red corset which could actually be laced down to a twenty six inch waist. This was a ten inch reduction from Jim’s normal waist, and could only be tolerated for a short time.


The corset was heavily boned and when laced, kept the upper body ramrod straight. It also was hour-glass shaped, and imparted quite a figure to the wearer. The result was to emphasize the hips and bust while minimizing the waist.


This had only been laced about half way closed, so it was still comfortable. Red garters hung down and these had been fastened to a pair of very sheer, beige colored hose of the finest silk. Just touching then excited Donna. Wearing them kept her in a state of high sexual desire.


Two silicon bust pads nestled in the bra cups at the top of the corset. These were so realistic they even bounced with every movement. The result, when combined with the cinching and boning of the corset was a very realistic cleavage.


Over this went a red slip with a lade hem and lace cups which cradled the false breasts. Red thong like panties were drawn up her crotch and over her hips.


The feel of all the satin which rustled and slid across each other with every movement insured that Donna would enjoy her evening. She just loved wearing such finery.


The dress was a work of art. Made of the finest Quiana fabric, it slithered over her body. It was long sleeved, and also a bright red in color. It had a scoop neck, with a sash which crossed her bosom in the front. The dress fell in many folds to below her knees and had a red applique of fine sequins which started at the bust line and reached to below the waist.


The dress had yards and yards of fabric in the skirt. It moved about as she walked, brushing her silken covered legs in a very sensually manner.


Donna thought this was the sexiest dress she owned. It covered her much more than some of her strapless numbers, and revealed very little, but the feel was so sensual. Wearing this she felt like she could seduce any man she might meet.


At this point we should probably digress for a moment. Donna loved to flirt with men, and she was pretty enough to attract their attention, but she never went any further than flirting.


She had never kissed a man. The thought of a man’s lips on hers was a total turn off. The idea of a man running his hand up her leg and under her skirt was repulsive. She knew she could never submit to sexual contact with a man.


One time she had been dancing with a man, his hand on her waist. He had pulled her close and held her tightly as the music played. Her breasts had pressed against her chest, and she had thrust her hips forward as her partners often did.


As her crotch came into contact with his, she felt the bulge press against her. This guy was excited and he wanted her. She had pulled away and left him on the floor alone.


Her heels were specially selected for tonight. She did not intend to be standing or walking around much, so she had chosen her red sandals. These had a closed toe, and a strap which started at the vamp and wound up around her ankle. A red leather bow graced the instep.


The heels were about four inches high and very narrow. The result was a very sexy pair of shoes which called attention to her long legs, but offered little support at the ankles. Each step had to be made carefully or her heel would turn under.


Her blond hair was piled high on her head and long dangly earrings hung from her lobes. These were clip earrings as she had chosen to not pierce her ears. She had a job in a very square business and could never explain pierced ears to her co-workers.


Stephanie was dressed in a simple skirt and blouse outfit with black pumps of modest height. The whole experience was new to her, and she was going to be an observer for most of the night. She just wanted to see what this scene was all about.


Donna had insisted on some form of bondage as her price for escorting Stephanie to the event. As a result, Steph wore a rhinestone studded slave collar with matching wrist bands. These were more ornamental than functional.


The other band, however, the one which no one knew about was very functional. This one was made of leather and was fastened tightly around the base of Steph’s cock and balls. Donna had watched as Steph had raised her skirt and lowered her panties.


Donna had reveled in the embarrassment Steph displayed as she fastened the device on her organs. She had pulled it to the last notch despite the pain and then snapped the small padlock. Donna had the key, and she whispered in excitement what Steph was going to have to do to get it back.


Stephanie was not sure if Donna was serious. She certainly hoped not. One thing was certain though. Steph was going to remain in a state of arousal until that strap was loosened. No amount of stimulation would overcome the pain and the constriction and allow her to cum. She was going to build up quite a load in her balls. Whoever she finally got to fuck was going to get a real gusher when she was finally spurted.


They had arrived at the party and checked in. Alyce had greeted them at the door. She smiled at Donna and made a reference about the last party. Donna had been a submissive that night and had done a scene involving saran wrap and whips. It was a scene she had decided to forget, but it obviously had affected Alyce.


The two had toured the facility, and then settled down to watch some of the early scenes. In the middle of one, Alyce had wandered by, and then she and Stephanie had disappeared. Donna was so absorbed in what was going on in the main dungeon, she did not really miss them for a while.


When Steph reappeared, it was with two goons in tow. These were two friends of Alyce’s and Donna knew from past experience how strong they were. They grabbed her arms and lifted her to her feet. She opened her mouth to protest, and Steph rammed a huge red rubber ball between her teeth.


A strap ran through the ball and around her head. It was cinched tight and she was unable to speak. She shook her head as she tried to get accustomed to having her mouth racked so wide open.


Her dress was removed and gloves pulled up her arms before Stephanie’s words began to penetrate her foggy brain.


“Alyce told me how much you like to have someone you do not know take charge of you and inflict long term punishment on your bottom,” she said.


Donna shook her head and tried to deny such feelings. She was a dominant, and she realized she actually hated the submissive role. The scene last month was because she wanted to learn about saran wrap bondage and the lesbian who specialized in it had insisted on a real scene.


“Oh, she also told me you would refuse at first, but to just ignore you,” Steph continued. “She also gave me some really great ideas for things to do to you.”


“Oh, great!” Donna thought. “First I get trapped into one of Alyce’s jokes, and then I find myself at the mercy of an amateur. What else can go wrong tonight?”


She was about to find out. The gloves which had been drawn up her arms had several buckles which assured they would not be removed. They also had straps and buckles which hung down from each thumb and finger.


Donna was led over to the center of the room. A chain hung down from the ceiling at this point. Stephanie removed Donna’s slip and her panties. She stood now in her corset, nylons, heels and her gloves. Her white skin made a sexy contrast to the red clothes.


Steph took the chain and wound it tightly around the base of Donna’s cock, trapping her balls as well. It was secured with a padlock which held everything in place. Donna studied the arrangement for a moment and realized she could not free herself. Someone would have to unlock the padlock and the key was nowhere to be found.


Next Steph ordered the two helpers to cinch Donna up. They complied and began to tighten the laces of her corset. Slowly they drew the edges of the garment closer and closer together. As the two ends tried to meet, Donna felt her middle being squeezed tighter and tighter.


Each time she gasped for breath, they would draw the thing a little tighter. She felt like she was going to die from lack of air if they did not quit.


At last the garment was fully tightened. The laces were tied off and the excess cut away. Donna now had a 38-26-34 figure as she swayed back and forth on her heels. She did not dare lose her balance or she would wind up hanging from her cock. Slowly she managed to calm herself down and regain her breath.


Her hands were now placed on her hips and the straps from her fingers and thumbs drawn tight. Her thumbs reached behind her back and her fingers came to the front. The straps crossed her back and stomach and fastened her opposite digits together. When tightened, she was helpless.


Stephanie showed her the leather paddle and the cat which Alyce had thoughtfully provided. A few cuts of each soon had her howling thorough her gag and dancing about on her tether.


Stephanie laughed and then brought out the coup-de-grace. This was a pair of high heeled pumps in black patent. The shiny shoes glistened in the light. Donna tried to protest as she saw that Stephanie intended to make her wear these monsters.


Her own shoes were removed and her feet forced into the incredible arch of these things. A full six inches high and needle sharp, the heels stabbed down to the floor. Donna found herself on the ball and toes of each foot, trying desperately to keep her balance. Her breasts were thrust out and her ass stuck out in the back as she tried maintain her balance.


Her toes were forced into the pointed toes of the shoes until her feet cramped with the pain. Patent leather shoe locks circled her feet at the instep and up around her ankles. They made certain she could not kick her way free.


For two hours she had stood in agony as guest after guest used the paddle and whip on her unprotected ass. She now was not sure which hurt the most, her ass or her feet and legs.


Stephanie had disappeared for quite a while, leaving her to the tender mercies of the other guests. None had been very tender. The women had concentrated on whipping her and watching her dance. The men had fondled her, feeling her curves and rubbing her crotch. Several had rubbed their bare cocks in the heated crack between her ass cheeks.


Donna was sore, mad, and very upset by now, but all she could do was moan in protest and sway back and forth on her painful perch. She vowed to get even with Stephanie and Alyce as soon as she got free. This was to be a long weekend, and she would get her revenge later.


She would soon see how Steph liked to be bound and helpless. Perhaps she would even arrange for her to be given to some of the randy men who always wandered around the edge of the scenes. Maybe that huge black guy with the gigantic equipment hanging down between his legs.


She had heard a couple of the women talking about him at the last party. They were in the bathroom and had thought Donna was just another girl.


“God,” one of the said. “I thought he would never cum. He almost split me in two with that monster, and it took nearly a half hour and every trick I knew to get him off.”


“I know,” the other replied. “Janice told me he likes to use the back door too. He says it takes longer, but he enjoys the extra leverage he can get. She watched him ravage a slave girl once. The poor girl could hardly walk when he finally pulled out of her poor rear entrance.


Donna gasped through her gag as Stephanie finally stepped back into view. She was dressed exactly like Donna, but without the gag. As she pranced over to Donna, a light seemed to gleam in her eyes.


“You’ll never guess who I ran into,” Steph began. “She says she is an old friend of yours and she knows exactly what turns you on.”


Stephanie seemed to just bubble over with excitement as she danced about. She seemed to have no trouble prancing about on her six inch heels, her hands securely fastened to her hips and her waist cinched tight.


“Her name is Susan,” Steph continued, “and she has volunteered to teach me a bit about all this and about you as well.”


Donna blanched at that name. It could only belong to one person, and the next thing she heard was the sibilant whisper of Susan’s voice in her ear.


This was not something Donna had planned for when she had invited Stephanie to the party. The things Susan whispered made Donna turn pale. Her laughter as she pointed to the huge black man was as evil as anything Stephen King could have dreamed up.


Donna shuddered at that sound, for she knew it meant Susan was enjoying herself. She also knew that Susan’s enjoyment would mean nothing but pain and humiliation for Donna.


Susan soon had Stephanie fastened up, standing in front of Donna. She removed Donna’s gag, and told her they would stand there facing each other until Donna had begged Stephanie by word and action to let her suck Stephanie’s cock and to shoot her cum down Donna’s throat.


Donna gagged as she thought of her assignment, and of having to seduce Stephanie in front of all her friends. She was going to have to whisper her endearments for all to hear. She was going to have to kiss Steph while all watched. She would run her tongue and lips around her throat, kissing her like a wanton in heat, causing Steph’s temperature and desire to rise even further.


She would rub her crotch hard into Steph’s crotch while the crowd stood around and cheered and made suggestions.


She thought about the band she had forced Steph to wear. She looked down to see it was still in place. Steph’s balls were swollen with desire and Donna had no doubt they were full of cum. She knew Susan would make certain all of that cum wound up inside of Donna.


She knew she was going to do all these things and more. All this so that she would get to give a public blow job.


Donna also knew that she would comply, and she would force herself to act the part of a wanton whore. She knew this because she knew Susan and the things Susan could dream up to make any man do her bidding.


The first incentive consisted of a curious pair of earnings. They were about twice as long as normal earrings and seemed to have attachments at both ends. These were for pierced ears, but this did not bother Susan. Two quick pops later and Donna had pierced ears.


Her objections did no good. She pleaded with Susan not to continue, and her reward was two more pops. Now she had two gold studs in each lobe as well. More objections won her a nose ring. She finally managed to bear her pain and humiliation in silence.


Susan laughed her evil laugh as each indignity was imposed. She was in a rare mood tonight, and had obviously decided to make some kind of an example out of Donna.


Two more pops and Stephanie had holes to match Donna’s. She looked a little bemused, as if maybe this had not been part of the plan.


The earrings were soon attached to the four helpless ears. Donna’s right ear was attached to Steph’s left and vice versa. Their lips were about three inches apart and their eyes stared into each other. Donna realized her job had just gotten a little bit harder.


She also knew that Susan would not stop with this. She clenched her ass cheeks in anticipation of the coming beating, but even she did not anticipate what Susan had conjured up for the crowd’s entertainment.


The sound of footsteps behind her was her first warning. She could not turn her head as they approached, but her eyes grew wide as she felt a pair of hands grab her bottom globes and pull them apart. Then next thing she felt was the blunt head of what could only be a cock come to rest on her sphincter.


Donna had never accepted a man in her ass before. She certainly did not want one there now, but she knew that Susan would get what she wanted one way or another.


She also knew that Susan would keep tormenting her until she had seduced Stephanie. She began to whisper sweet nothings to Stephanie, all the while thrusting her hips forward to avoid the contact at her rear.


It did no good. The cock just moved forward with her, putting even more pressure on her opening. She felt his muscles tense and knew what was about to happen. In order to avoid screaming, she plastered her mouth to Steph’s, kissing her with great force as she was penetrated.


Her tongue shot out as the cock shot in. Her crotch was buried tightly against Steph’s and her hips began to grind out her pain. She knew that everyone watching would think she was displaying great passion and enjoyment.


The chains kept her cock hard. Her hips were thrusting and grinding away and her lips were pressed against Stephanie’s. To anyone who did not know better, she was in the throes of deepest passion.


On and on the rape went, the cock thrusting in and out of her violated rear. Faster and faster it plunged in and out until it suddenly swelled up and began to spurt. Donna felt the cum like a fountain of molten juice in her churning guts. She could not help gasping out as more and more cum filled her up.


At last he stepped away, and Donna could pause to regain her composure. She was able to tell that Stephanie was getting excited. Soon she could probably be persuaded to succumb to Donna’s blandishments and agree to a blow job.


As Donna continued the task of seducing this innocent person so cunningly strapped to her own body she felt another set of hands on her bottom.


Her cheeks were again pulled apart and a new cock came to rest against her anal opening. This one seemed to be even larger than the monster which had just left her.


She glanced down as two hands reached around to cradle her breasts. The hands were black! This was the giant with the monster cock.


Donna braced herself as the hands worked their way down to her hips. The held her in place as the pressure increased.


She pleaded quietly with him to ease his way in. She knew she would have to accept him, but that thing he was pressing against her felt large enough to split her right up the middle.


Suddenly he pulled back on her hips and thrust forward. She screamed as the full length penetrated her at once. The lubrication of the previous fuck made it possible, but the pain was intense. She was crying as he began to slowly withdraw only to plunge back to the maximum depth on the return stroke.


Donna thought he would last forever. She could barely concentrate on seducing Steph as he pounded inside of her. At last she felt him speed up just a little and then shout as he began to fill her up with his spend. Of course, it did not end there. Many others lined up to get their shot at the helpless ass.


Two, three, four, Donna lost count. As fast as one cock shot its load into her, another took its place. She was being gang raped while she herself tried to convince the boy/girl in front of her to allow her to suck his cock.


At last Stephanie agreed, and Donna was released. She fell to her knees in relief, crying as she quickly took Steph’s throbbing cock between her red painted lips. Without the use of her hands, she could not make this a quick job. She must use her lips, and tongue and even her throat muscle to get this girl off.


When she felt the tell-tale swelling begin she readied herself to pull away, only to find Susan’s hands at the back of her head. She was thrust forward forcing Steph’s cock deep into her throat, and making sure she had to swallow all of her cum. A quick flick of Susan’s nimble fingers and the cock strap was removed.


Donna thought she swallowed at least a gallon of cum. Steph seemed to just keep spurting as all the love juice which had built up through the night was at last released. The cock stayed buried in her throat as Steph emptied herself in jolt after jolt.


“At least she would now be freed,” she thought. She found out that was not to be the case though. Instead Donna was placed into a sixty nine position with Stephanie. Each girl had a mouth full of stiffening cock. Each girl had a head fastened securely between her legs.


The two bodies were left in a small cubicle with the thoughts engendered by Susan’s parting words.


“It is now early Saturday morning. This party lasts until late Sunday night. You two are going to be my pets for the entire time. By the time it is over, you will beg to be allowed to wear those six inch heels home and you will be very talented slaves to your masters!”


Both girls shuddered at the thought, but each felt a string in her loins and a swelling in her mouth as she contemplated her future.

5 thoughts on “HOW HIGH HEELS by Debra Darling

    1. Thank you Debra, and good to hear from you. Do you know who did. meanwhile I will contact C.C. just check his view.

      Good to see you still writing. Looks like you took a couple of year off … bit like me 🙂

  1. Just wandering the internet and came across this again. I wrote the story for Cathy Slavik many years ago when she was still publishing.

  2. susan & steph need to be beaten witin an inch of their lives for justustice not revenge Donna or anyone deserved that kind of treatment!!!!!!

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