Last Will and Testament Ch. 04

Holly checked her E-mails at lunchtime on her mobile phone. Just one new message. Sender: Mr. Pointer.

It was now about a week since she had completed the second of her tasks. She still had three more to go if she wanted to get her hands on her million pound inheritance. Three more ex-boyfriends, three more tasks.

Things had been somewhat awkward at work since her previous task. Her supervisor, Dan, and a number of her other colleagues had been present to witness the final part of her previous task. They had seen her naked, licked ice cream from between her legs and watched as she gave her ex-boyfriend a blow job. None of them had mentioned it to her directly, but she had overheard many of them telling their colleagues, and by now she was sure the entire office knew.

She opened the E-mail. The time, place and boyfriend's name were there, but of course no details of the task that she was to perform.

Holly tried to guess what it may be that she would be expected to do for Sam. Sam had been her very first boyfriend, the boy she had lost her virginity to. Their relationship had ended when she slept with his best friend, Rick. Perhaps somewhat stupidly, they had slept together at a party at Sam's house -- Sam had walked in on them, and, though she had pleaded with him to forgive her, tried to suggest that Rick had almost forced her to, he was having none of it. She hadn't seen him since that night. She'd dated Rick for a short while, but it didn't work out.

She knew that Sam was a fitness trainer, and wondered whether the task would be linked to this. She liked to think of herself as quite fit: she did work out in the gym occasionally. Perhaps it wouldn't be so bad.

***

Holly arrived at Sam's house at the appointed time -- 10am on a Saturday morning. The house was a small one on a back street in an inner-city suburb.

Checking that she had the correct house number, she walked up the drive and knocked. Sam answered almost straight away.

It was strange seeing him again, years after their last encounter. He was still hot -- he had always worked out a lot and played a lot of sports, and this was obvious from his body. The memories came flooding back to her of how happy she had been with him. Not only had he had the looks; he had had a great personality too. He had adored Holly, and had always paid her plenty of attention. It had been clumsy sometimes, yes, but she had been his first girlfriend, and he'd had all the right intentions.

Sometimes she regretted cheating on him. Perhaps if she hadn't they could still be together now. She saw his facial expression, and could see that as much as he was trying to hide it, just seeing Holly again had brought back the hurt of that night when he had caught her with Rick. She regretted that.

Sam showed her into the living room, where Mr. Pointer was standing.

"Well, let's get it over with, then," Holly said.

Mr. Pointer produced the envelope and passed it to Sam. Sam tore it open, read the contents, and looked thoughtful.

As with the previous task, he allowed Mr. Pointer to see it, but did not reveal the instructions to Holly. Unlike either of the previous tasks, however, Sam explained that as he would have to make some arrangements, the task could not be completed today. She would have to come back tomorrow. She protested to Mr. Pointer, but he agreed with Sam -- arrangements would have to be made; it might be inconvenient, but she would have to come back.

*** That night Holly thought back over her time with Sam. She had felt so different then. She had been very shy at school, and it was not until she met Sam early on in her time at University that she had even been out on a date. She still had not had much confidence and had been very flattered when he asked her out. He was the boy all the girls wanted to date.

She remembered their first date. He'd taken her to an expensive restaurant. He'd saved up his wages from his Saturday job for weeks to take her. It had been really awkward -- neither of them had known what to do or say. But there had been something between them.

She remembered the dates afterwards, the growing chemistry, eventually the night that his parents were away. They had planned everything. He had promised to buy the condoms, but she knew him. For all his tough guy image, he'd be too embarrassed. She was right. Fortunately she'd taken the initiative to buy some herself. Extra large. That's what her friends had suggested they'd need. Truth was, she was rather scared that he might be.

The night had come and he had done a fantastic job. He'd cooked her a romantic meal. OK, so it tasted terrible, but he'd made the effort. He'd even scattered rose petals up the stairs. Seriously. Despite his tough guy image, he was so gentle with her, and as she lay there in his arms, she couldn't imagine ever being with another guy.

Sam had always been a bit shy in the bedroom though. As she grew in confidence with him, there were things she wanted to try that he didn't want to do. He didn't even like her talking dirty to him. She loved him, she felt so lucky to have him, but she just wished he would be a bit more adventurous.

Then Rick ruined it. Rick was one of Sam's friends, and he was dating Amy, one of Holly's friends. Holly had confided in Amy about Sam's reluctance to experiment in the bedroom, and Amy in return had told her all about the different things she had tried with Rick. Amy must have told Rick about the conversation, and he started to taunt Sam about his reserved nature in the bedroom.

Well, that party had come, she had probably had too much to drink, and Rick offered to show her what she was missing. At first she had declined, but then she had got into an argument with Sam. She had accused him of paying too much attention to the other girls there. She was over-reacting, she realised now, but somehow she had ended up in bed with Rick. Sam had caught her, and that had been that for their relationship. Holly often wondered what would have happened had it not been for that stupid mistake.

*** The next day Holly turned up at Sam's house to see him waiting by the car with Mr. Pointer. After exchanging short greetings, they all got in the car, and Sam drove.

Soon Sam pulled in to a car park and they all got out of the car. Sam led them round a corner, and she saw the reason they were there.

In front of them was a large obstacle course, which she guessed Sam must use as part of his fitness training. Sam explained that the task was simple -- to complete the task she would have to complete the obstacle course.

He led her into a small hut. A group of four men, all dressed in khaki (as was Sam), were inside, some standing, some crouched on the floor.

"OK, we just need to get you into your uniform then you're ready to go," said one of them.

"Uniform?" Holly asked, looking around.

"Yes, just there," the man said, gesturing to what looked like an empty space.

Holly looked at Sam, confused.

Sam blushed.

"Your uniform is... well... invisible," he said quietly.

"You mean that I have to do the course naked?" Holly asked, not really surprised.

"Well, no, just in... well, the invisible uniform," Sam explained, unhelpfully.

"And where do I get changed?" Holly asked, already able to guess the answer.

"Here will do just fine," said another of the khaki clad men.

Six pairs of eyes -- Sam's, Mr. Pointer's, and the four other men's, stared at her.

Sighing, Holly started to undress. Firstly she took off her jacket, then looked around for somewhere to put it. She didn't want to put it on the floor, which looked very dusty and dirty. One of the men held out a hand and took it from her. Next she pulled her top over her head and handed this to him too.

She crouched to pull off her shoes and socks, pushing the removed socks into the shoes and placing them to one side. She winced as she had to put her bare feet down on the grotty floor. Next she took off her jeans, handing these too to the willing assistant.

Once again it was time to reveal her body to strangers. She reached behind her back to undo the clasp on her bra. The fact that she was in a small ramshackle hut rather than the safety of a house made her feel more nervous about exposing herself, and she delayed the reveal until the last moment, holding the bra to her chest as she pulled the straps over her arms. Finally she took a deep breath and pulled the bra from her chest, surrendering it to the man who was holding the ever growing pile of her clothes.

Finally it came to the last item protecting her modesty. She placed her right hand in front of her crotch and edged her knickers down using her other hand. She stepped out of them, being careful not to allow them to touch the floor, then handed them too to the man holding the rest of her clothes. She then joined her right and left hands together and held them in front of her crotch, giving her the slightest protection from the men's gaze.

The man holding her clothes picked up a rucksack which had been left in the corner of the room and shoved the clothes in there. Then he indicated back to the location of the supposed "invisible uniform".

"Now put your uniform on," he ordered.

Holly realised that this was a little charade they had planned. She was now expected to mime getting herself into a uniform.

"Um... so, underwear first, I suppose?" Holly asked.

"Why, how else do you normally dress?" one of the men asked, laughing.

Holly pretended to pick something up.

"Ah, she's gone for the g-string," laughed one of the men.

She tried to ignore him, and concentrated on pretending to put the underwear on. She did try to mime with one hand, but found it impossible, and had to use both hands, meaning that she completely uncovered her crotch.

"A bare pussy!" one of the men declared, and the others laughed.

"Was she like that when she was with you?" another asked Sam.

"Um... no, she was always quite hairy down there," Sam said, quietly.

Holly found this discussion particularly embarrassing; a group of men standing around discussing her pubic hair. She remembered that she had worried for weeks before their first time whether she should shave, whether her being unshaved would put him off.

The imaginary g-string on, she reached for another item.

One of the men supplied the details.

"Not just a bra, a sports bra," he declared, laughing. "Stops your tits bouncing about as much. Sam's thoughtful like that."

She mimed putting on the bra. After that came the trousers, the shirt and the jacket. Having completed the ritual, she was of course as naked as when she had started. More naked, given that she was no longer covering her crotch.

The men continued to leer at her body and make lewd comments. Holly kept looking at Sam. He wasn't joining in. In fact, most of the time he wasn't even looking at her. He seemed somewhat embarrassed about the whole thing.

***

It was drizzling with rain as she walked out onto the obstacle course. The sky was filled with black clouds, and Holly was keen to get the task over with before a downpour began.

The men set themselves out around the course. One of them led her to the starting line. She looked at the first obstacle -- a high cargo net for her to climb. The man blew his whistle, and she set off.

The net seemed even higher than it looked once she started climbing it, but she made good progress up it. It was going to be difficult, she was sure, but the course shouldn't be anything she couldn't handle.

Reaching the top of the net she found a rope which she was supposed to swing down on. She grabbed on to the rope, wrapped her body around it, then jumped from the platform, swinging down. The ride ended with a splash in a large pool of cold, muddy water. She released the rope, stood up and looked down at her body, now covered in water and mud. She was looking forward to a nice hot shower when this was over.

Holly waded through the pool and out the other side. With the water dripping off her, she ran on to the next obstacle. It was a ladder of overhead monkey bars. She stood on the step at the beginning and reached up to grab the first bar. Her other hand joined her first, and she was now suspended from the bars. She started to move carefully along the bars, first moving one hand then bringing the other to join it. She was aware that her body was now completely exposed to the watching men, but tried to block this out and just focus on making her way safely along the bars.

She almost made it to the end, but a combination of her wet hands, the wet bar and a bit of over-confidence meant that she lost her grip and fell. The fall was not particularly far, but she landed rather ungracefully with her bottom taking the impact of the fall, much to the amusement of those watching. She quickly stood up and started to rub her now aching bottom.

She went to start on the monkey bars again, but Sam rushed over.

"Sorry, Holly, the rules are that if you fail to complete any part of the obstacle course you have to start the course again."

At least she had not got very far round, she thought, and started to head off for the starting line.

"Not so fast," Sam instructed. An air of authority was in his voice now. Perhaps now they were on the course, his professional trainer side was taking over.

"We don't want to be here all day, and judging by your performance so far, we might well be at this rate. So Simon asked me to help you along with a few extra incentives."

Holly didn't like the sound of that.

Sam asked Holly to get back on the monkey bars. She was confused, but complied. The rain was still coming down and the sooner this was over the better.

Holly looked down at Sam, and saw that whilst she had been getting back on the bars, one of his assistants had come over and handed him something. She realised almost immediately what it was. He stepped up to where Holly was hanging down from the bars, still gripping on tightly to avoid falling again. At first she thought it was a table tennis racket, but then she realised its actual purpose. It was a spanking paddle.

Sam stood behind her. She tried to look back to see what was happening but he ordered her to keep looking straight ahead.

"Holly, you don't realise how much you hurt me when you cheated on me with Rick. However much this hurts you, it won't be anything like that much. But it's time you were taught a lesson."

He delivered the first smack to her bottom. It was brought with some force, right onto her left buttock. She squealed out, mainly from surprise, but also from the feeling of the paddle making contact with her bottom, which was already sore from the fall. The blow made her body swing forward slightly, and she almost lost her grip on the bars.

Holly clutched on to the bars tighter and took a deep breath. She wasn't going to show him how much she was hating this.

Now a second blow, this time to her right buttock. Holly had never been spanked before, and was surprised by how much it hurt. For the first time in her life, she wished that Sam didn't work out quite so much. Another hard smack back on her left cheek. Holly winced but didn't cry out. Smack, smack, smack. Ouch, ouch, ouch. He alternated the swats, spreading the punishment between each of her cheeks.

He only gave her ten smacks. It must have only been a short time, but it seemed like ages. Then he allowed her to let go on the bars, and this time she managed to land on her feet.

She looked at Sam. There was a look of satisfaction on his face, a small smile. She had hurt him all those years ago. Now he had his chance to get his own back.

Back to the start of the course. The whistle blew again. Up the cargo net again. Swinging down into the muddy water with a splash. Standing up, running to the bars. More careful this time. She completed the bars without incident. "Yes!" she exclaimed, and ran on to the next obstacle.

The next obstacle was a series of bars set at different heights. One of the men from the hut was standing by them, and explained to Holly what she must do. She must climb over the first one, go under the second one, over the third, etc.

The first few were not much of a problem, but as she got further on the ones she had to go over got higher and the ones she had to go under got lower. She had almost reached the end when she caught her foot on one of the bars as she went over it and fell, grabbing onto the next bar to break her fall. She looked round, hoping no one would have noticed, but saw Sam running towards her, carrying the paddle.

Sam led Holly to a bar that he thought of appropriate height, then ordered her to bend over it. It was a humiliating position to be in, naked, bottom in the air. Before he commenced the spanking, another lecture.

"Holly, I want you to remember this the next time you're thinking of cheating on someone. If you misbehave, you'll always get punished for it in the end."

Having got her into this position he once again commenced a spanking over her already sore bottom. Smack. He hit her right cheek first. Smack. Now on her left cheek. She winced but did not react. The third smack hit her on a particularly painful part of her right buttock, and she let out an exclamation of "ouch!" Almost immediately Sam delivered another smack to exactly the same place.

Six more whacks with the paddle followed. Holly managed to just about resist crying out again. She reassured herself that next time she would get this right -- he wouldn't paddle her a third time.

Back to the start of the course, and this time she tackled it with renewed determination. Up the cargo net, swing down on the rope -- splash. Across the monkey bars. Next it was over and under, over and under. She cleared the last one and gave another little cheer, mainly to herself.

She looked up to see what was next and her heart sank. They had set up a gauntlet for her to run through, and had hung large punchbags on either side for the men to swing. The four men had now lined up, two on each side, each holding one of the bags.

Holly stood at the start of the gauntlet, steeling herself. The men looked at her, expectantly. Finally she decided to go for it. She ran past the first man before he had a chance to release, narrowly avoided the second bag, but was hit by the third. It wasn't particularly heavy, but it caught her off balance and she fell to the floor. At least they had put down a padded mat to break her fall.

She scrambled to her feet and saw Sam running over again. This time though he didn't seem to be carrying the paddle.

"Something a bit different this time," he explained. "Joe here is going to get a reward for being the one to knock you over."

Holly looked at the man who had knocked her from her feet. He was the one who had earlier embarrassed her so much by asking Sam about whether she had been shaved when she was with him. He had a smirk on his face.

"Holly, stand here," Sam said, gesturing to a space near to the gauntlet.

Holly did as she was told.

"Stand with your legs apart and hands behind your head," Sam ordered.

She looked at him, but he just stared back at her defiantly. She dreaded what was coming next, but just wanted it over and done with. She did as she was told.

"Go on, Joe, she's all yours," Sam said.

Joe stepped forwards and stood facing Holly. He contemplated her exposed body for a minute, then reached out with his hands and grabbed her breasts. Holly's natural reaction was to stop him, to push him off, but she knew that this was not allowed. She kept her hands behind her head, out of the way.

Joe played with her breasts roughly. Firstly he gave each of them a good squeeze. Next it was her nipples' turn, and each was given a few hard tweaks. Then he had some fun bouncing them up and down and side to side with his hands. Holly hated having her breasts treated like this. She wished that she had been given another paddling instead.