Fuck Me Shoes: The Flip Side

In the taxi she reflected on what had just happened. She had been taken by a man she hardly knew, but already trusted deeply to a dark club where she had been a toy for strangers to explore and arouse. She had been intimately exposed and wanton in surrendering to her own pleasure in a way that would have shocked even her a couple of hours earlier.

All the time he had watched over her and she had been aware of that at a deep almost animal level of awareness. Although she could not have verbalized it before, this deep care was a great part of what she sought in this life.

He smiled at her and asked, "Our next stop will be a complete contrast to what you have experienced so far this evening. Are you ready to continue?"

While she had no idea what she was in for and that fact scared her (in an exciting way) she also knew that she trusted him so deeply that she had no inclination to stop now or do anything to displease him.

So she nodded.

He took out his mobile phone and she heard him say "Be ready in 5 minutes".

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Five minutes later the taxi stopped outside a townhouse. He helped her out and she noted that he did not pay the driver; there must have been some prior arrangement.

The door was opened by a young girl in a maid's outfit. She said nothing, and they walked into a smart hallway and up a sweeping set of stairs. He took led her into a room where three men stood.

The men were different builds, one tall and slim, one short and well build, and one tall and slightly overweight. They were dressed identically in dark shirts and trousers. In addition each one wore a silky mask over their face, leaving holes for their mouth, nose and eyes. Each mask was a different color, one red, one blue and one green.

"These are my associates", he said, "and you will treat them with respect"

"You have just enjoyed an experience where your pleasure was paramount; you had to give nothing and nothing was expected from you. Now we flip the coin. In the next hour you will be delivering pleasure to these men and will receive nothing in return other that the pleasure of servitude"

"There will be an element of chance in what unfolds and there will be some small elements of choice. I will place three balls in this black bag, one red, one blue and one green. You will draw a ball and that will determine which of my associates is to be the next recipient."

"Additionally you will note the three boxes on the desk. Each of these contains instructions on how you are to pleasure the chosen man, some materials for you to use and, maybe, a choice or two." A smile crossed his face as he said this.

"I will repeat that you will receive no pleasure in return. You will not taste any of these men or receive any cum. Should you cum yourself during this experience, the evening will immediately end and you will be sent home. Do you understand?"

She heard herself say, "Yes. I understand," but had made no conscious effort to do so. This was unfolding with a strange inevitability.

She was falling deeply under his spell. He seemed to know what she wanted; what buttons to push even more than she did. While she had loved the brazen behaviour he had elicited from her in the club, this task seemed to hit a more sensitive spot.

Her choices were largely gone. She was here to serve; to be used, but not just used. Used in a way he had engineered and now controlled. He was there with her to see it all went well and she knew that a good performance from her would please him greatly.

Quite what the consequences of a bad performance would be she did not know, but she did know she didn't want to find out.

The very worst would be for him to discard her with no way to atone and the very thought of this was already brought heavy dread to her heart.

She now looked at the three boxes. Each was the size of a shoe box and black. She wondered what they held. She would know soon enough.

He held the black bag out and said, "Choose a ball."

She dipped her hand in and pulled out the green ball. At the sight of the green ball, the men in the red and blue masks silently left the room.

"Now pick a box."

She opened the one in the middle with some trepidation. Inside was a card that she would read in a moment, a pair of latex gloves, and three flavored condoms.

The card read as follows:

You will give oral pleasure to this man. You will use your mouth only to achieve this and you will not touch any other part of him sexually. To ensure this is just his pleasure you will wear the gloves supplied and he will wear a condom. Your choice in this task will be which flavor condom you use.

You will clean him after with the enclosed wet wipes and tissues.

Remember you are not to taste this man!

Yeuch! She hated giving a blowjob with a condom, but otherwise this should be easy. She knew she would do as required and expected to feel cheated by not tasting the man or his cum. The choices she had were strawberry, banana or orange. A spark of mischief in her immediately chose the banana one. Somehow it seemed appropriate.

She donned the latex gloves, pinging them as she did, picked up the condom, wet wipes and tissues and she walked towards the "Mr Green." He stood with his feet slightly apart and his arms behind his back. She knelt in front of him and looked back at her Master for assurance. On seeing his nod she started to unzip the man.

His cock was neither soft nor hard. It was uncut and, as she lifted it from his fly, about 4 inches long and averagely thick. It was not ready to wear a condom yet so she started to caress him with her gloved hands.

It felt strange and instinctively she went to take it in her mouth. She heard a disapproving cough and suddenly remembered she was not allowed to taste the man. Instead she pursed her lips and gently blew on the head of the penis as her hands rolled back the foreskin. Slowly the cock grew and stiffened. As it grew it also became hotter and she was aware that her breathing had become shallower and quicker.

She was ready to start properly now. She tore the foil wrapper off of the condom and immediately smelt the banana aroma. She smiled to herself and gripped the teat between her teeth pulling the rolled body against her lips. She moved her head forward and towards the glistening cock and positioning the teat over its end used her lips to push/unroll the condom down its length.

This meant that she took the whole of the cock in her mouth in the first move and somehow she found she did not mind the taste. The flaccid teat at the end felt strange against the back of her mouth, but that was all.

Covering her teeth with her lips she started to move along the length of this cock. It did feel different in the condom, but not bad and she was warming to her task.

She moved her hands to the man's trousered arse and stabilized her movement.

She felt his hips tense and increased the pace and pressure. As she felt a small tremble she changed tactics. She started to hum sending small vibrations through his cock.

This hit the spot and she felt him start to move with her. She guessed this involuntary and a good sign as he had given no encouragement before this point. She tried to look up at his eyes, but the mask obscured them. His head did seem to be tipped back slightly and that too seemed to be a good sign.

The restrictions on touching, tasting and feeling frustrated her, but it also concentrated her mind on the task in hand and reading the smaller signs of his growing excitement.

The humming really did work and in a short while she felt his hips tense more and his cock seemed to grow. As she felt this, she pulled him deep inside her mouth and although almost gagging felt him spurt and fill the condom. He spurted five or six times and each time she heard a small "aaagggh" escape his lips.

As his orgasm subsided he slowly moved her head back and flicked her tongue over cock head as it left her. It was obviously very sensitive now and she saw a shiver run through him.

She watched the erection subside and at an appropriate point supported the glistening condom and eased it off him.

Letting the cock rest on one hand she used a wet wipe to gently clean the cock of any remaining cum. She dabbed it dry with a tissue and only just remembered not to kiss it.

Replacing the man's cock inside his trousers. She closed his fly and stood up.

Removing her gloves like a surgeon and leaving them on the small pile of debris, she returned to her Master's side. He leant and kissed her gently saying, "Well done," before dismissing "Mr Green" with a nod.

Surprisingly she did not feel cheated. Instead she felt pleased that she had performed the task and had received her Master's appreciation.

He offered her the black bag again and this time she retrieved the red ball.

His hand guided her back to the boxes. This time she opened the one on the left. It contained a new pair of latex gloves, some lubricant, a single condom, wet wipes and tissues and a card.

This time the card read as follows:

You will ride this man's cock until he comes. You will not receive any of his cum nor will you taste him. A bench will be provided for him to lie on so that you may straddle him with your feet on the floor.

You have two choices, which once made cannot be changed. The first is whether to be naked or dressed while the second is which way you wish to face, his head or his feet."

Again this seemed pretty easy, although she was not sure if she could control her own orgasm. She had heard that, when faced with similar constraints, men thought of anything that was unsexy, maybe she would try it.

She thought of her choices for a moment and decided to stay dressed. It seemed more in keeping with the intent of the task, which is to give pleasure, but not to receive any. Also it was easy. Since the club she was not wearing knickers so all she needed to do was hike her skirt up to her waist.

She was pondering the question of which way to face when "Mr Red" entered the room. He was naked and carrying a padded bench. The bench was around 5 feet long, 18 inches wide, and about 18 inches high. He placed it in the middle of the room and lay on it. His head rested on his hands at one end, his back along the length of the bench, and his feet fell either side.

His cock was semi-erect. This cock was circumcised and looked bigger than the last one. His body had a fair costing of dark hair, something she liked.

At this point she decided that she would face him, but that first of all she needed to arouse him and apply the condom.

She knelt beside him and sat back on her heels. She was suddenly aware that she was wearing those shoes again. She knew now that they would forever be connected with this evening.

She slipped on the gloves and started to caress his cock. As it stirred, she placed a little lubricant in the palm of one hand and started wanking him.

Long strokes from base right up to the tip, her hands gently closing over the head.

Soon it was hard and up so she opened the condom and this time applied it with her hands. It didn't reach the bottom of this cock….it was bigger.

She stood up and hitching up her skirt she straddled him, her cunt over his cock. Slowly she bent her knees and guided his cock to her cunt opening. She was still wet from all the activity in the club and he slipped in easily.

She gasped involuntarily as she took him in.

She placed her hands lightly on his chest and started to perform. It was a complicated sexual ballet lifting herself on and off him. Well not quite off, she always had at least the tip of his cock inside her. In addition she started adding a slight twist of her hips on each downward stroke, first twisting one way and then the other.

She soon found her thighs hurting. She had ridden men before but always from a kneeling position, never while standing in high heels.

She needed to rest her legs so she settled on him and felt his cock hit her cervix. She was fully impaled and now she started to rock back and forth, while also squeezing her cunt muscles in time with her rhythm.

She was getting to him, but it was also getting to her. She was getting aroused and nearly lost herself in this scene. Her head was back, her breathing rugged.

She heard a cough and suddenly realized the danger. Her Master did not want her to fail, and, as she was new, he was giving her a little help, this would not always be the case. As her experience grew so would his expectations.

She now saw the muscular pain in her thighs as the safety mechanism she needed and raised herself up again.

She set about fucking him now, a professional job so to speak, up and down, squeezing and twisting being sure to watch him for signs of a growing orgasm. She started to feel his hips move under her, rising to meet her, and she knew he was close.

She intensified the pace until she felt him tense and his cock grow. She immediately settled in him, engulfing him in her cunt and squeezed her muscles in time with his spurts. It felt warm, but not wet coz all his cum was held in the condom.

With him spent she stayed where she was for a few moments before lifting off him completely, one hand slipping between her legs to hold the condom in place.

With her skirt still over her waist, she knelt beside him and watched the erection subside. As it did, she removed the condom and cleaned his cock, using her hands to slowly ease out the last drops. While she was not allowed to feel or taste any of this, she could still smell him. She loved the after-sex smell, him, her and spunk.

When she was satisfied she was done, she stood up, removed the gloves, straightened her skirt, and returned to her Master's side. He smiled broadly.

Inwardly she had an even broader smile. She could feel that while he was testing her, he was also helping her. He did not want her to fail. With that her trust in him grew greater.

Two down, one to go.

Only Mr Blue was left so no ball to pick this time. As if summoned, Mr. Blue entered and immediately went down on his hands and knees in the centre of the room. This seemed odd, but then again she hadn't opened the last box.

Her Master brought it to her and watched as she opened it. Inside were the usual latex gloves, wet wipes and tissues. In addition this time there was a more lubricant, a slim, smoothe vibrator and a larger thicker realistic looking dildo with very prominent veins. And, of course, the card.

It read:

You will bring this man pleasure through his arse. You are reminded that you will receive no cum nor will you taste any part of him.

You may choose which tools to use and how and you may, if you wish, use your hand to wank him as an additional stimulus."

This was new to her, but she had read about some of this, how to ease the tight hole, how to stimulate the prostate, etc

Now this was new territory for her. If this had been first how would she have coped? Now, having completed the first two she felt ready for anything.

Momentarily a thought flitted across her mind. Had there ever been any choice or uncertainty in this? Had her Master engineered the order of the tasks too> She could not see how, but almost as soon she realised it didn't matter. He had demonstrated how he would look over her and take her to places she needed to go, both inside and outside her head.

Here goes, she thought.

Having put on the inevitable gloves, she placed some lubricant on her right index finger and moved to kneel behind "Mr Blue." Using her left hand to part his buttocks, she started to stroke his tight hole. The lubricant made her finger slip easily over it and in no time she found herself pressing down a little more with each pass. After 20 or so strokes the tip of her finger just popped into the hole.

She felt him clench at first, but then relax. She then started shallow movements with her finger with each forward stroke entering him a little deeper. Soon she had most of her finger inside and was moving it faster.

Time to move on. She took her finger out, placed a second beside it, added more lubricant, and pushed both inside, easily. She worked the two fingers, then three. He was pushing back towards her so she presumed he was enjoying it.

Removing her fingers, she decided to use the vibrator. She lubed it, switched it on, and pushed it into the waiting arse. Instead of using it to fuck him, she slowly moved it around looking for the best spot.

She knew she found it when he gasped and again his arse clenched. Now that she knew where it was, she set about teasing it, stimulating it, moving back and forward over it, touching it lightly and firmly.

His hips were moving more too and as she looked below she saw that he had a raging hard on. Now for the final phase.

She pulled the vibrator out and he visible deflated. She quickly lubed up the dildo and was soon pushing it back in. This was thicker and she felt more resistance. It stretched him more, but soon it was in all the way to its plastic balls.

She adjusted her position to the side slightly and as she started fucking him with the dildo, her other hand wrapped itself around his hard cock and started wanking him. She kept a rhythm such that when the dildo was in deep her hand was just as the tip of his cock; as her hand slid down his cock the dildo was pulled from his arse.

He caught on quickly and soon he was doing the work (though she suspected he wasn't supposed to!) moving his hips as her hands and the dildo stayed still. He was double fucking himself. He soon reached a shuddering climax, his cum shooting onto and splashing off the wooden floor.

As she let go of him he slumped, but he stayed on his hands and knees. As previously she used the wipes and tissues to clean him, cock and arse, before mopping his cum from the floor.

When she was done she stood up and returned to her Master. Behind her she heard "Mr Blue" leaving.

This time she had felt more in control of the task, maybe this was a little of how a Dom feels? If so she could see the attraction, but in recognising this she also reinforced the submissive role that she knew was hers by birth.

Her Master lifter her face and smiled at her.

"You have done well, little one. I am pleased."

And with that he kissed her lips and offered his hand. What would the rest of the evening bring?