The Lottery Winner's Challenge - Cover

The Lottery Winner's Challenge

Copyright© 2011 by John D

Chapter 7: Entering the forest

It took me a long time to get to sleep as my head was buzzing with the possibilities of what could be in store for myself and flashergirl the following day.

I was woken on by the sound of an envelope being pushed under my door at around 8am and got out of bed to open it.

'Dear finalist,

We have arranged a tray of breakfast to be brought to your room at 9am. Do not leave your this floor of the hostel for anything and do not talk to any other contestant or ex-contestant. We will collect you at around 10.30 and take you to the final.

Failure to abide by these rules will result in instant disqualification.

Lots of love,

Angelina'

I feel back on the bed and dozed until I was woken by a loud knock on my door. Breakfast had arrived and I got up naked to take the tray from the receptionist. Breakfast, was not cereal and milk but a full cooked breakfast complete with a morning newspaper. Well a News of World.

I took my mind off the impending challenge and flicked through the newspaper but before long I was torn from my thoughts by another loud knock at the door. One of Angelina's maids was there and I was ordered downstairs before being blindfolded and led into a minibus that was parked
around the corner. We waited for ten minutes before I heard someone else getting in and the vehicle starting. About twenty minutes later, the minibus ground to a halt on a bumpy road and there door opened. The maid led me out, letting me catch my head on the top of the bus as I got down from the vehicle and then walked about ten minutes across uneven ground.

My blindfold was roughly taken off me and I opened my eyes to see Angelina and the two maids. Flashergirl was next to me and she threw us each a bag. We were surrounded by thick woodland.

'All six ex-contestants and two of my ... ummm ... friends are in this wood. Each of them have three cards - a pink one, a blue one and a gold one. The gold card is sealed in an envelope and contains a number from -1 to 6, dished out at random. The blue and pink cards have challenges or tests. You have an hour to approach as many people as you want and ask them for the dare. Mark takes the blue card and Marie the pink. If you complete the challenge in front of them you get the golden envelope which must be opened at the end of the game when we tot up the points.

The wood is about three quarters of a mile wide and a mile long and there are also four umpires who are dressed with blue sashes across their chest to ensure fair play. We have placed the ex-contestants and therefore you will find your challenges next to big wooden panels which are painted in white littered around the forest. Once you have done a dare, the other finalist cannot also complete the dare from the same person. Any questions?'

I shook my head and opened my bag.

'Get changed into those and I will blow my whistle in two minutes.'

Flashergirl and I hurriedly changed into a long T-shirt which only just covered my crotch and a basic set of plimsolls. I left my clothes in the bag I was given and stood on the edge of the path looking into the wood.

'Good luck', I said to flashergirl and held my hand out.

'You too', she replied and hugged me instead.

'When I sound my klaxon after an hour you must be back here within five minutes.' Angelina told us and we got ready to enter the wood'

'PEEEEEEPPPPPP'

flashergirl and I ran off in opposite directions, tripping over branches I fought my way past the undergrowth away from the beaten track. The trees thinned out slightly and then started going downhill. I tried to look round for a white board and before long found a path worn out through the
bracken and fern which was growing. This led to a small copse, where bigboy19 was sitting on a chair opposite a big white wooden block, about three foot high.

'Hello mate', he greeted me as I walked fervently up to him. 'There ya go' passing the blue envelope across.

I tore it open and read out aloud.

'You do not have to complete this but your challenge is:

How many people of the same sex have you had sexual relations with?'

I smirked. 'Five. You, tord_phreak, londonjames, icum4u and myself.'

'Very good', he replied and passed me a gold envelope. As I went to leave he took a blue sash out of his pocket and put it on.

'Are you an umpire now?' I asked.

'Yes. I'll follow you if you like'

'Sweet. You can hold onto the envelope then. Its hardly though I have any pockets'. Bigboy19 put the golden envelope he had just given me into his inside pocket and he followed me out of the clearing.

'I can't tell you where any of the other people are, but I have seen the map', bigboy19 confided, 'and I wouldn't spend too much time walking in that direction or that direction if I were you.'. He pointed further down the track the way I had just come and further into the forest'

'Why are you helping me?', I asked.

'Oh come on. You've been a great sport all week. Both of you have. Pity you aren't going to share the million really'

'Hmmm' I hummed and we half-walked, half-jogged in silence for a bit.

'You two would make a good couple. Mind you, I'd have thought that about Josie but I am not so sure now.'

Glad to be changing the subject I pressed him for an answer, and it appears they weren't speaking at breakfast. We rounded a corner and saw big_boned_lucy waiting for me dressed in a Roman toga. She too was sat opposite a big white box in a clearing.

'Your challenge', she said a handed me the pink envelope. I lifted my T-Shirt up to reveal my flaccid penis.

'I need a blue one. Look'. She grinned and passed me the blue envelope instead.

Reading out loud, 'You do not have to complete this but your challenge is:

Fill the test tube the ex-contestant has with semen in front of him or her'

'You going for it?'

'Of course' I said and whipped my cock out again. I was already getting hard and began pumping furiously when I realised that I didn't have the test tube. I held my hand out and Lucy passed it to me giggling.

Stroking harder and harder I could feel myself getting nearer and nearer. With a tiny shudder, I felt my muscles contract and I pressed the top of the test tube onto my cock and let it dribble in.

Rolling my fingers down my penis I drained any semen left and passed the tube to Lucy who put the rubber plug in and passed me the golden envelope.

Bigboy19 and I left very quickly with my distinctly unsatisfied. Lucy has always struck me as slightly desperate and I didn't really want her inviting herself to be with us for the next half an hour.

'Where now?' I asked as soon as we were out of earshot from Lucy.

'I don't know, but I would guess going this way', he said, subtly extending his finger further up the path.

'What a good idea!' I exclaimed in mock surprise.

'So tell me, what would you spend your money on?'

'If I won? I don't know. House. Car. Holiday and a night of drinks on me I suppose'

'A million pounds is a lot of money. I'm not I sure I would ever go to work. Or back to it'

'You'd get bored' I told him and he shook his head.

The path forked and Bigboy19 instinctively took the right hand fork deeper into the wood.

'Oh I'm sorry. Do you want to go this way?' he asked jokingly.

'Nah don't think so. I would have chosen right' I lied.

The path soon narrowed and then disappeared and I was beginning to doubt bigboy19's directional and navigational skills as we hacked our way through the thickening bushes and unseen trip hazards. I was about to question his knowledge of the map when we stumbled into a little clearing and Josie was waiting, dressed only in a see-through rubber apron. She nodded at Bigboy19 who was staring at her intently'

'Your challenge', she said holding a blue envelope out.

I took it from her and read it:

'You do not have to complete this but your challenge is:

To enter the buttplug provided into yourself and then perform oral sex to the ex-challenger. The buttplug cannot be removed until the klaxon has sounded and the points totalled.'

'No problem', I said and took the little bag from Josie, which contained a four inch buttplug and a bottle of KY Jelly. I smeared the plug in KY and then reached around and gently lubed my arsehole. I slid in no problem, but felt ever so uncomfortable, like I was ever so slightly contispated.

I looked at Josie and guided her onto the large beach towel she had just laid out. She spread her legs and I began devouring her slit, concentrating on massaging her hole and then up to her clitoris and back circling it as I went.

I heard her start to breathe out faster and then mew slightly. I used my hands to pop open her hood and began sucking on her clit and felt her muscles in her leg twitch. She sat up slightly and then began groaning in pleasure.

'Oh yeah, thats it', she cried as my lips pursed over her exposed clit and I began sucking on it.

'Ahhhh ... UGGGGGGGGGGGGGGGGHHHHHHHHHHHHHHHHHHHHH HHHHHHHHHHHHHHHHHHHH', she screamed and her muscles tensed. Waves of pleasure cascaded through her and she shuddered. Her hands went to her hips and she lifted my face upto hers kissing me passionately.

'I'm sorry.', I said pulling myself away from her before my stiffening penis could go too near her holes and my willpower disappear. 'That's bigboy19's job'

Bigboy19 smiled at me and passed me three golden envelopes. 'Cheers mate'

'Ummmm?' I went to ask him where I was to go but didn't want Angelina's sister to know we had bent the rules.

He nodded towards a tree 10 metres away I took the hint.

'See ya later', I called out and ran off towards the tree. It wasn't long before I encountered a blackberry bush and went around it, but this led to more bushes and soon I was being dragged off the original bearing I wanted to take. I was just about reaching the end of my patience when I came into a clearing, which unfortunately contained no ex-contestant. It was also at the end of the forest and so I turned around to climb out of the copse in a slightly different direction. This too was blocked by a holly bush before too long, and in trying to go around it and keep on the right path, I found another clearing. With one of Angelina's friends.

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