The Challenge

All the girls had decided they wouldn't mention the prostitute role until they had all done it. The men knew it was them but no one had confirmed it. They were uneasy which made the girls happy. Those who had been with the prostitute had been made to pay by their shocked wives.

Now it was her turn. She didn't know how she had allowed herself to be persuaded to become a prostitute. She had hoped to avoid it as she wasn't sure she could pull it off. When she practised it in front of the others, before they started, she was so embarrassed but so wet. All had praised her. Listening to those who had already done it only heightened her desires but they had pushed the boundaries beyond what they and she had thought to do. How far was she prepared to go?

Ted was conflicted as he arrived at the pub. He thought it was between Jessie and Linda if the prostitute came along this evening. The others had said while they'd been sure at the beginning, during the act, they hadn't been sure it was their wives. Their wives had been angry as there was evidence of their indiscretions and they had been made to pay for their transgression. He couldn't believe Babs had flashed her pussy to them all. She was normally so reserved. Bob had told them afterwards how conflicted he had been wanting her to but not wanting her to. Overall, it was fantastic. He was worried when he came back in due to the eyes it wasn't Babs. When they saw him on the Saturday, Bob said when he got home, he had to grovel as she saw the blue lipstick on his cock. She had him eat her out for hours before fucking him senseless.

If it was Jessie, what did he want her to do? He didn't know. As he entered, he was shocked to see how busy it was tonight.

The others were there.

Eric looked nervous. He tried to cover it up, "Maybe we should ask for a cover charge as it's costing us a fortune these Thursday's nights."

Ron, George and Bob nodded. They were relaxed, their wives had been through the pub. At least they thought they were, it was part of their game, surely. No one had lasted long enough to get a prostitute story so far. They wouldn't find lookalikes to play them. No, it was them but?

They were on their second drink, busy chatting away when they became aware the background noise had stopped. A very busy pub was dead quiet.

They looked up and saw what had stopped all conversation.

There was a blond bombshell walking into the pub. Her hair was in pigtails but still came down to mid breast. Speaking of breasts, these were astounding. They seemed very large with no droop. The gold satin and sheer blouse was striped, which showed that she was braless and much of her breasts. The gold micro mini was three inches short of her stocking tops. The suspenders looked strained. The four-inch heels made her legs and bum look awesome.

As she walked past the customers, a few tried to buy her a drink. A couple, having had a few drinks, asked, "How much love?" She smiled and replied, "I'm very expensive but you won't have had any better!" She leaned towards them and whispered in their ears. They blushed.

Ted had gotten up and pulled her gently, "If you join my friends, I'll buy you a drink, away from these ruffians. What would you like?"

Ted pointed her to the others. The crowd parted so he found himself at the bar. He ordered and didn't have to pay. The barman said, "Just seeing her is worth that. You lucky bastard!" He grinned.

Ted joined the others. Their eyes were on stalks. The satin strip just covered the nipples but not all the areolas. The sheer allowed an amazing view of those breasts. Each was hard.

Ron had asked her name as Ted returned, "Helen!"

They looked surprised, so she continued, "After Helen of Troy. Men have fought over me. My looks, body and bum have raised many from the dead."

They laughed. Ted was finding it difficult to concentrate. Helen was sitting facing him. He saw her face, the gold lipstick, gold nails. Her breasts were stupendous. The blouse hid yet showed them off to perfection. As he looked down, he saw a gold belly jewel. The short skirt allowed a lot of thigh to be seen. He was hard. It didn't help as she licked her lips as she stared at his erection.

She leaned over towards Ron as he spoke. Her legs opened slightly and he saw her mons was covered by gold satin panties. He relaxed slightly as he knew the others wouldn't see anything like what Joanna had shown. At least he did, until she leaned slightly away from him towards Eric. Her pussy was highly visible through a sheer gusset. There was a letter H attached to one of her labia's.

Ted was shocked. He didn't understand his reaction. He was even harder. He wanted her to display herself yet he was so afraid. Was this what he saw on Bob's face last week? He struggled with the conversation.

Eric asked if she wanted another drink and she said yes. He went to the bar, looking closely at her breasts as he passed her. Helen came over to sit beside Ted. He knew the others would now be seeing her intimately if she opened her legs further.

The conversation flowed and Ted didn't realise his hand had strayed to her breast. He was feeling it and the nipple expanded. He undid two more buttons so at least half her breasts were exposed. He heard some gasps from the crowd.

Helen looked at him and smiled, "Naughty boy. Are you looking to buy or does one of the others wish to buy? I'm not cheap but you won't get a better titty fuck/blow job than mine."

George smiled, "What would it take to buy your knickers?"

Helen laughed, "Oh, these," as she opened her legs and leaned back, "They're very expensive. It would cost you £60." She closed her legs.

Soon there was sixty pounds on the table. Helen had never been so aroused. She saw the desires in their eyes. The more she saw their erections, the more she soaked her knickers. She stood up and slowly peeled her knickers down her legs and placed them on the table. There was silence, apart from some gasps of shock, in the pub. She sat down and opened her legs so they saw the H. Her pussy was wet and engorged, very inviting. She laughed as they licked their lips.

Ted was shocked beyond belief. Helen was enjoying the view she had of four hard cocks in front of her and the feel of the one she was stroking beside her. She knew she had to hurry things or she'd lose what little control she had left.

"Well, have you decided if you want me or not. I'm sure if you don't, you friends will."

Ted stood up and held her arm, "Let's go. As she turned to him, he saw how much of her breasts he had exposed. He almost came then. The whole valley was visible. He didn't see her pussy wink at the others. They did and almost came. As they walked out of the pub, those who were closest showed such desire, Helen almost came herself.

Once in the back car park, she turned to him and said, "What do you want?" "Your famous titty fuck blow job," he replied eagerly. She nicely asked for her money which he paid.

Helen slowly unbuttoned the rest of the blouse, pulled his trousers down and released his hard cock. She added some lube to her breasts and began to slowly tease his cock, tonguing the tip as it came near her mouth. She quickened the pace and used more tongue. Very soon, Ted was bucking, trying to fuck her tits. She massaged her breasts firmer and held his cock in her mouth. He came quickly. To his surprise, he didn't go soft.

Helen smiled, "I hope you confirm the best ever. I've even left you hard so you can impress your friends or do you want more?"

Ted looked at her, "The others saw your pussy, openly bare. From what I saw through your panties, it looked fantastic. I'd love to fuck it."

Helen smiled, "That's £30." Ted paid.

Helen leaned over a car's bonnet and hitched her skirt up, "Some say my bum is made to be watched when fucking me. What do you think?"

Ted growled, "Wow! It's certainly made for watching." He put his cock in her extremely wet pussy. He tried to go slow but her pussy was wanking him hard. She was bucking back strongly against his thrusts. Even though he had just cum he felt himself cumming again far too soon. Once he stopped, she pulled away, turned round and licked him clean.

She kissed him lightly on the cheek and said, "I have to go. I'll be back another night. It was so good."

He watched her walk away and he felt himself react to that bum as it swayed and the bottom of her bare cheeks came into view.

As he returned to the pub and made his way to his friends, his face showed his shock. He told them what he did. Ron burst his thoughts, "Hope Jessie doesn't find out!"

"Fuck! What if it wasn't Jessie?" he thought.

Ted's night started to go wrong when he undressed and Jessie pointed to the gold lipstick on his cock. He was a penitent soul for a couple of hours showing his devotion to her pussy.

Day 24; -Friday - Debbie - Errant Student

George was happy arriving home. He had passed his medical the previous night with flying colours. At least that's what he saw as he came. This month so far had been unbelievable. What was on tonight's menu, he wondered.

As he came into the living room he saw a student standing there. Her brunette hair was in bunches. She had no makeup on. Her white blouse was strained against some awesome looking breasts. Her charcoal skirt failed to clear her bum cheeks. The holdup stockings were white. She had on school shoes. Her face looked worried.

As she saw him, she straightened herself which brought those tits out to perfection. She licked her lips.

She spoke quietly and nervously, "Sir, Mistress Cruella has sent me to you for punishment. Here is her note."

George noted the tears appearing in her eyes. He read the note before he allowed himself to appraise the young lady in front of him, knowing she was waiting to see his reaction. He heard her breathing quickly. He could feel her fear. Mistress Cruella only sent the worst miscreants to him for punishment.

He looked at her, a stern look on his face. He spoke firmly, "Mistress Cruella says that in class you have been inattentive, stubborn and argumentative. It was your turn to be the class model and you refused to strip off. Everyone else had been a life model previously and you drew them with no questions asked. You were the final one. You objected as no one else had both pussy and arse plugged by vibrating dildos. You refused and fought her when she tried to put the nipple and clit clamps on you. The other pupils were to draw you as you climaxed, the nuances of colours as your body exploded was the final portrait needed for them to pass their exam.

"You refused. You refused. Helena, you think you are above everyone else here. You are a student and you will do as you are told."

He grabbed her and marched her to his private room. Once within he found the restraints as he had left them from the day before when another pupil had misbehaved. He threw her on the table and quickly secured her arms and legs. Before he began he placed a gag in her mouth. All her struggles had been in vain and she tensed watching him, fearing what was to come.

He opened a drawer and took out two large vibrating dildos. Helena gasped. They were far bigger than the ones Mistress Cruella had tried to put into her. As he rummaged about she feared what else he would bring. Her worst fears were realised when she saw him holding the nipple and clit clamps.

He spoke, firmly, no trace of emotion, yet she saw his cock was interested in her. "Helena, you will be the class model when I have finished with you. You will be happy to be their model. If Mistress Cruella says you look unhappy, we will do it all again and again until you are just a quivering wreck."

He slowly removed her blouse and made sure he spent time caressing her tits. At first he was soft watching her eyes as she tried to resist the emotions her body was feeling. When he saw the first seeds of desire he pulled them more firmly causing her nipples to expand. He played with them for five minutes until she was rising from the table. Her flushed face, the shine on her body showed she was being aroused. He put the nipples clamps on. He could see her try to scream but the gag stopped it.

He lifted her skirt exposing her pussy. He was glad it was bare, all the better for the other students to see how a woman's body changed as she orgasmed. At least she had obeyed the school rules. No girl was allowed to wear underwear unless on their period.

He felt her pussy and as he expected it was wet, very wet. He took some lube from the drawer and began to lube up her bum. She was trying to escape his finger then the second one but she couldn't. He saw her reaction as he gently finger fucked her arse. He felt it relax. As it did he grabbed the dildo and inserted it. He did it firmly, not allowing her to control the situation. She was crying as it entered her fully. Her scream would have been heard by many in the school if she hadn't been gagged.

She was watching warily through the tears as he took the second dildo and inserted it into her pussy. She had never had one so big in her. She felt his fingers run over her pussy lips and down her perineum and around her bum before repeating and repeating. Without her consent her body was rising from the table. She could feel the beginnings of an orgasm as the dildos began to vibrate.

She saw his eyes stop on her breasts and he began to pull at the nipple clamps. The sensations overcame her resistance and she orgasmed. Her body trashed around for about fifteen seconds before it subsided. There was to be no reprieve. Soon she was building to another orgasm. She felt the clit clamp go on. Was it pain or ecstasy? Soon the vibrations drove her to another orgasm. She almost dislocated her shoulders as she tried to get her hands to stop the dildos. She was thrashing about, no control over her body.

The vibrations died down and she briefly thought the worst was over. She felt the nipple and clit clamps begin to vibrate and tighten. How did they do that? Her nipples were in pain and ecstasy but her clit was beyond pain. She was fucking or trying to fuck the clit clamp. She couldn't control her body's reaction. She was moaning around the gag. Had she not been gagged she'd have been begging to be released, this was too much. Pleasure/pain/pleasure. Slowly it appeared every cell in her body was about to cum. She was frantically trying to get out of the restraints with no success.

Her body was jumping from the table. She was glad it was padded as she'd be badly bruised. Her mind was leaving her body as the biggest orgasm of her life overtook her. Her hips were fucking an invisible man. He would have been a rodeo rider if he could have stayed on as her hips bucked uncontrollably. Her pussy and tits were trying to cum first but it was a dead heat. She convulsed for a minute as she came and came and came.

George watched in awe as she came. He had never witnessed one like it. His cock was as hard as he could remember. He turned off the vibrations as she was done. He removed the gag so she could breathe better.

There was still a part to go but he changed it slightly. When she was able he took his cock out and fed it to her. In a firm voice he said, "Helena, I shall release you shortly to return to your class. You will walk to your classroom with the clamps and dildos in place. Mistress Cruella will pose you and control your orgasm so the others can record it. Once they have done that, you will return here.

"To show your class how you have been made subservient, I shall cum in your mouth. You will not swallow. Your fellow students will be able to draw your open mouth displaying my cum. Mistress Cruella will give you a note for me to tell me how long you managed to keep it in your mouth.

"Once you return, you shall fuck me until I cannot raise another erection. Do you understand?"

Helena nodded her acceptance. George began to fuck her mouth and soon filled it with his cum. He released her from the restraints and sent her to her classroom. It was a ninety-minute class so he would be waiting for her then. She walked away gingerly, aware of the dildos in her and those clamps.

Helena went to the classroom. Mistress Cruella was cruel. She had her pose with no dignity at all. She used the vibrators to stimulate her and she had three orgasms in front of her classmates. She was so embarrassed. It was the first one she swallowed the headmaster's cum. Her classmates laughed. She didn't like giving blowjobs and they knew it. None had been allowed to cum in her mouth.

The period seemed to be far longer than ninety minutes. Mistress Cruella gave her a note for the headmaster. She returned to his study. As she entered she saw the table was still out. She shuddered. She had endured enough, surely no more.

She handed him the note. He looked at it. He spoke softly, "You kept it until your first orgasm. Not too bad. Now bend over the table."

Helena did as she was told. She'd learned disobedience at this school was not tolerated. She was relieved when she felt the nipple clamps being removed although as the blood rushed in, the pain came as well. She stifled her tears. The clit clamp meant her clit screamed in pain as it was removed. She couldn't stifle the scream which accompanied it. The pussy dildo came out slowly. Perversely she was missing feeling it in her. When the anal dildo was removed she felt empty.

It was only briefly as the headmaster entered her pussy and began fucking her. There was no finesse, she was just a fuck vessel. Soon he exploded into her pussy. He didn't try and leave it, so she used her pussy muscles to massage his cock as she had been taught in the sex class. When he was hard, he congratulated her on her pussy's prowess before stuffing his cock up her arse. Again, he just fucked her. He added a few spanks which had her shout in pain. He came in her bum and let her recover before pulling out.

He left for a few minutes before returning. She had turned over as he had instructed. Her head was over the edge of the table allowing him to throat fuck her. He was brutal but didn't last long before he came in her throat.

He was done and sent her away.

Later, George and Debbie cuddled up closely in bed. George was concerned, "Debbie I hope this fulfilled all your fantasy. I know me cumming in your mouth while you were tied wasn't in it but you looked so gorgeous, your body's colours so arousing and your pussy was flooding everything, I was so aroused I had to do it."

Debbie smiled and kissed him, "George it did add to it. I know you were concerned when I explained this fantasy in front of Sharon. I've learned so much about myself I never thought. I never knew I could enjoy being so dominant until the other night. Yet I do have a need to be subservient on occasion. I saw how troubled you were when throat fucking me but George it made my dream. I didn't know the range of the vibrators' controls. I thought I'd just sit and relax but every now and again you switched them on until I had the three orgasms my fantasy said. Thank you, it took a lot for you to overcome your fears to do this for me.

"I love you so much. We've both learned so much and the great thing is there's still so much to learn. Even after the love month is over, we'll play new games."

George smiled, "I know, I never felt I could enjoy being so dominant over you. Last week when you exposed my need to be subservient I was so surprised how I enjoyed it. I know I had spoken about it but it was a fantasy I both liked and feared. In the end my reaction surprised me. We've both learned so much. We can play those again but not too often.

"One thing I would love to continue afterwards is you telling me naughty stories. I love that. I can't rate them in any order as all have been ten."

Debbie smiled and said, "I will. I love you."