Do You "Care to Dare!"

My names Matt and I live in a pretty boring town where very little happens. So I was surprised one morning, walking through town I saw a film crew, and had to find out more.

As I neared, someone with a clipboard came up to me and asked me a few questions. How old I was? 24. Was I single? yes. Did I live locally? yes. Would I be interested in taking part in a new fun TV programme airing on Channel 6? OK, I replied.

Soon I was introduced to the presenter Steve, who was pretty slick with shiny white teeth and you could tell he would try it on with all the girls.

Without warning, the camera was rolling and Steve went straight into TV mode.

"Hello and welcome to a BRAND NEW series. Its called "Care to Dare!" and we find out how far people will go for cash!" Steve then turned to me and the cameraman swung the camera round. "Hi, and whoooo are yoooou?" Steve asked.

"My names Matt and I am 24." I replied.

"Do you fancy some lovely cash?" As he said it, he pulled out a wad of crisp twenty pound notes.

I thought to myself, my girlfriend Tara has left me, I am having to pay the crazy rent and am seriously skint. So I said "Yes, please."

Steve went on "More importantly do you.................CARE TO DARE?"

"OK" I said cautiously."

"You don't sound that sure, Matt!" Steve jumped in.

"Yes, I definitely want to CARE TO DARE!" I said quite forcefully.

Steve collected a set of cards with instructions on them. "Round 1. Right here, in the middle of this fair town, I want you to give me your shirt for £100. Do you CARE TO DARE?"

It didn't take me long to decide as the shirt was from Primark and cost £8. "Yes" I replied and took off the shirt.

Steve handed the shirt to an assistant.

"Round 2. Right here, I want to give you £100 for your shoes and socks. Do you CARE TO DARE?"

That was a no brainer as they were cheap trainers. Now I was bare footed.

"Round 3. Right here, I want to buy your trousers for £250. CARE TO DARE?"

OMG, I didn't fancy standing in the middle of town in just my pants, but that would make it £450. So I agreed.

"Round 4. Right here, I want to buy your underpants. What if I offered you £550 to make it a round £1,000? Do you CARE TO DARE?"

A thousand pounds would be amazing in my bank account, but I would be naked, so I declined.

Steve jumped back in "What if we added another £500, making the total £1,500. Do you CARE TO DARE?"

In my mind I was thinking, shit, shit, shit, that is an awful lot of money. Rather than think twice, I whipped off the underpants and handed them over.

Steve was all smiles. "Wow, what a wonderful contestant you are Matt. You have won £1,500 and we have only just started." Only my hands stopped the camera and public from seeing everything.

Steve turned to the camera and said. "We will be right back to this lovely market town and our great contestant Matt, after this small commercial break!"

As we stood around the lady with the clip board asked me to sign a contract. She said it was just a standard waiver and gave the programme certain rights. I had to be really carefully I didn't expose myself as I signed the contract. It was then that I looked around and saw there was quite a crowd gathered to watch. Thankfully I didn't spot anyone I recognised.

After what felt like an age of standing there naked, they were ready to film the next segment.

Steve went straight back to big smiles. "Hi and welcome back to CARE TO DARE. Matt here has taken me for £1,500 so far, but will he get more?"

Steve turned to me. "Matt, you have been really great so far and definitely you do CARE TO DARE. But will you CARE TO DARE some more?"

I didn't know what he was going to dare me to do, but I was just thinking of the money so agreed.

"That's wonderful Matt. So what if I offered to double your money to £3,000?"

I didn't even hesitate and said "yes".

Steve put his hand up "hahaha, that was a little hasty, you don't know what I am going to ask you to do. So for £3,000, you are to let us give you a complete make over, from head to foot, no questions asked and we have full control. But once you say yes, if you back out, you lose everything."

Before I could answer, Steve looked over at the clipboard lady and asked her "Have you got the contract signed?" She held it up and waved it about.

Steve said "So matt, for £3,000 will you let us give you a complete makeover at one of this towns top businesses?"

I was hesitant, but thought why not and it was £3,000, so I nodded and said "ok".

Steve looked to camera "You have witnessed that folks, this town has some great people like Matt here who definitely does CARE TO DARE!"

We didn't walk far, as I was shown into what looked like a hairdressers.

Steve spoke to camera "Ladies and Gentlemen was are lucky to be sponsored by 'Fine and Dandy' this lovely beauticians that will make you all feel wonderful, here in the centre of this fine town. Don't forget to make your appointment and contact details are on screen now and at the end of this programme."

Thankfully it was empty as I was directed to a room at the back, camera following.

Steve turned to me and said, "Right Matt, these ladies are going to give you a real pampering. Let them do their stuff and we will be back to see the results later. We hope to see a new you."

Soon I was laying down naked and receiving an Indian head massage. as that was going on another lady was working on my finger nails. I guess I must have fallen asleep as the head massage was amazing.

I didn't have a clue how long I had slept for, but was rudely awoken as Steve and cameraman came into the room.

"Hi, ladies and gentlemen. Lets see how the transformation is going."

As I had only just woken up, Steve asked the beauticians "So you lovely ladies, how are things going?"

One replied " Well you join us at a great moment as the final coat of nail polish has just dried and Matt will be finished."

I now suddenly came round, NAIL POLISH?!?! Looking down my body, there was shock after shock.

Then I heard Steve kick in again... "Right ladies tell me everything you have done for the makeover."

The nearest beautician to Steve replied "Well lets start with the basics. We have given Matt a full body exfoliation with a special chemical peel. So nothings going to come back for a good six months. We then gave his skin some precious creams to make it particularly smooth and soft. We gave his chest area saline injections to give good D sized breasts as well as injections into his buttocks to give shape. Matt has now got a lovely shoulder length bob style wig in his shade of brown. It has been fixed into place, so wont come off for at least a couple of months."

I looked down in shock at the two mounds on my chest!

The beautician went on. "We then have given him a full facial tattoo makeover and sorted those eye brow and lips. He now sports two pairs of earrings as well as two tongue studs. We have injected a suppressant into his groin, and have sorted his terrible toenails and given him hand nail extensions and of course painted and polished the lot."

I wondered why my tongue felt odd and now I realised I could feel the studs in my mouth.

The beautician finished off by saying "We have fitted a lovely floral cropped blouse to show that wonderful stomach area Matt has. Under the in-fashion skater skirt, we have given matt a pair of lovely bright pink Miami knickers that show the leg and round bum cheeks well. As Matt is just under five and a half feet, we have finished off with a cracking pair of lovely shoes with four inch stiletto heels."

I was then helped up and directed to the full length mirror. Complete shock came over me as I looked at myself. There before me was the spitting image of my ex girlfriend Tara, except I was wearing clothes far more revealing than she would ever have worn. Standing was difficult in the stupid high heels though.

Just then, Steve was back talking to camera... "So Matt has had his makeover, don't worry Matt it is all temporary, but lets see if you would still CARE TO DARE some more?"

Steve turned to me, "Matt you have been a great contestant so far and you have won an incredible £3,000! If I said to you, lets see what the public outside think of your makeover for another £1,000 to make £4,000 in total!"

I had gone this far and crikey I thought I looked good, so agreed.

Tottering out of the beauticians, back to the busy town centre, the lady with the clipboard had been busy. She had a group of about ten young men ready to give their opinion on camera.

Steve went over and asked them one at a time... "So, let me ask your opinion of this lovely young lady. We have given her a bit of a makeover and the question I want to put to you is...would you "Bed her", would you "Wed her" or would you "Dread her"?"

One after the other, they all said "Bed her". Not one dread but also not a single Wed.

Although I felt a little bit down from the reaction, they all fancied me obviously. Wait what am I thinking. I am a guy and have been dressed up a bit tarty.

As I was getting my head round everything, Steve started up again talking to camera. "So ladies and gentlemen. Matt here has had his makeover and what a success it has been. He is £4,000 better off and the reviews are very positive, but will Matt go further?"

Steve turned to me. "So Matt, or should I call you Mary. So Mary, you have got £4,000, but would you want to try for £8,000?"

My brain just went, Jesus £8,000 would do so much good for me right now I have got to say yes.

Steve asked me if we can walk to the local park and I could give him his answer there.

Once everything had been setup in a quiet part of the park, Steve spoke to me and camera. "So Mary, would you be interested in going for £8,000? If you say no, you can walk away with £4,000. But if you say yes, you have to do what we dare you to do! Please remember if you say yes and then don't do what we dare you to do, you lose everything! You do understand don't you?" I nodded that yes I understood the risk, but £8,000 is still £8,000.

"Yes please." I replied.

The clipboard lady came forward with a small earpiece and lifting the wig hair to one side, slipped it into my ear. She asked if I could hear from it and I could.

Steve went on "So for £8,000 now, do you see that tall guy walking down the path. I want you to go up to him and give him a kiss, a nice proper loving kiss!"

I was thinking, OK a bit yuk, but for £8,000, a silly snog isn't a problem. As I walked up the path towards the tall chap, I was talking to myself saying "eight grand, eight grand, eight grand."

When the man got close I heard Steve talk in my ear, "Well done Mary, your doing a great job."

I walked in front of the tall man to stop his stride, closed in and started to kiss him.

His arms swung round my body and held me in tight. He was a good six inches taller than me and that was with me wearing those four inch heels. So he stooped down to kiss me. I didn't know how much kissing I had to do for the money.

I heard Steve in my ear piece, "Well done, keep going!"

I didn't know what to do with my hands, so I put one on his shoulder and the other behind his head. His kissing got more passionate and soon his tongue was sliding into my mouth. I wasn't thinking yuk, I was just thinking £8,000. One of his hands fell onto my now plump bum cheek, while the other clamped my head close to his. I couldn't move away even if I wanted to.

In my ear I then heard "That was wonderful, but maybe £16,000 would be the figure you want to go home with?"

I couldn't answer, but Steve went on "If you back out of the kiss now, you have won £8,000 and can walk away. If you stay for more and it will be much, much more, you will be £16,000 better off!"

I was in a dreamland just thinking of £16,000 in my bank account. The trouble was even if I just wanted the £8,000, I physically couldn't pull away from this mans strong arms as he held me tight.

Steve spoke in my ear again "So it seems your up for the £16,000, so let the fireworks begin."

The tall man lifted me slightly and my feet were off the ground. Soon he had taken me a short distance to a grassy area with a solid wood picnic table. I briefly had the chance to look round and couldn't see anyone. Before I could think twice, the tall guy, had his hand under the skirt, caressing my round bum.

After a while he moved us towards the picnic table. With ease, he lifted me up, so I was on my back on this table. He carried on kissing me and was then feeling my new breasts.

Steve spoke again "Your doing wonderful, soon you will have won the £16,000."

I was still away with the fairies, as the guy unzipped his trousers and pulled out a cock that was easily twice the size of mine. I just kept on thinking of £16,000 as he placed the tip of his penis at my mouth. I slowly opened up and soon four or five inches of his still limp dick was in my mouth. I hadn't a clue how to suck a cock, but what ever I did he seemed to enjoy and the penis gathered strength and got harder.

Very carefully he started to slip his cock in further and then back out again. As he did so he played with my breasts. The trouble was that they actually hurt when he groped them a little too hard. As he pinched one of my nipples I gave out a groan of pain and that seemed to excite him and his manhood. His gentle careful slide, changed to a more forceful and heavy stroke. I could feel his cock head hitting the back of my throat and yet there was still a good few inches left to enter my mouth.

His thrusts got stronger and stronger until his tip went past the back of my mouth and down my throat. He held it there for a few seconds and then pulled back out. He carried on like this for ages.

The crown of his penis when down my throat stopped me from breathing or saying anything, so when Steve said into my ear "Last chance to back out and walk away with £8,000." I could do nothing.

Concentrating on this massive penis, I was suddenly shocked as I felt two men grab my hands and direct them onto two more cocks. The men got me to wank them. Even now I was still thinking of the £16,000 prize as I felt another man step forward. He parted my legs and lifted them up. The tall man at my head end, grabbed my ankles and pulled them towards him. My bum was now fully on show as I felt the knickers being pulled out of position and, oh my god, I felt a semi hard penis at my hole. Hands parted my bum cheeks quite forcefully and without any care, the cock tip was rammed into my arsehole. I screamed, but that only excited the tall guy and his cock in my mouth.

The two cocks inside me got a rhythm and thrust in at the same time. The pain coming from my sphincter was extreme and it wasn't going away with each thrust. The two I was giving hand jobs to made me speed up. It wasn't long though and the guy between my legs was pounding harder and faster and then all of a sudden, he stopped. After he had caught his breath he pulled out, only to be quickly replaced by the guy on my left.

The tall chap was still pushing deeper and deeper into my throat, and yet still more of his shaft remained outside my mouth. Thankfully the guy giving me anal had a smaller penis than the previous guy and my behind was coping with this invasion better.

As things progressed, another man took hold of my left hand and made me work his semi hard cock. The tall guy was now as deep as he could go and his hand rested on my neck to feel the insertions and my neck expand.

God alone knows how long this went on for before the second guy came in my arsehole and slipped away. Now he was replaced by the guy on my right. Oh, I didn't like this cock, it was short and very fat. Every thrust sent a stab of pain up my body but somehow I got used to it. Just then a sixth man came forward and now took my right hand for personal pleasure.

More men came in my bum and more men replaced them as it was getting dark. I tried to keep count. The tall man was still working my mouth, but I seemed to count either four or five had cum in my hole, yet there was still more men to come.

When finally the tall guy came with an almighty blast of hot semen, all the other men had finished and gone. The last to come in my backside, had put something big inside me and fiddled with it before leaving. The tall man finally spoke telling me to swallow it all and clean up his cock. I did what he asked and then in the gloom the tall man zipped up his trousers and was gone.

I laid there for what felt like ages and slowly got up. I hadn't heard from Steve in a while and wondered where they were. I felt for what was in my backside and it was some sort of butt plug, but I couldn't get it out. I straightened my knickers and skirt. Walking down the path, I think I had counted nine or was it ten men who had come in my arse.

Steve, clipboard lady and the camera man were nowhere to be seen. I searched every bush and thicket but nothing. So I slowly walked back towards town as I tried to digest all that had happened. Funnily I seemed to be fine walking with the high heeled shoes now, but that was small grace for what had gone on.

Where was Steve and his team? So much for me winning any money. In town I found the beauticians closed for the evening and no sign of any film crew.

I started to walk in the direction of home, but as I walked past the police station, I stopped and thought about reporting how I had been conned, so I entered.

Speaking to the desk clerk, I was soon taken into an interview room by a detective. I sat down on a hard chair, but doing so set off the butt plug in my bum. It would go between vibrate and thrust with the occasional shock. My cock went into overdrive and it felt like I would almost instantly cum in my knickers. But by sitting to one side, it stopped so I could concentrate and relay the days events as best as I could.

Half way through though the detective told me to sit up straight. Each time I did the damn thing in my arse would ping into life, so I soon was back on one side. It seemed to infuriate the detective and he called for assistance. Soon I had an officer force me to sit upright on the hard chair.

The butt plug was working overtime on my arse and as I tried to remember the days events, my cock spurted cum into my knickers, once and then a second time. There was literally no let up.

Being in a mind fugged state with my cock on fire, telling the detective what had happened was exceptionally difficult.

He then spoke back to me. "So you admit to a public decency offence for being naked in the middle of town. You then admit to sexual favours for the benefit of a cash reward which, please excuse me is prostitution. And as you admit it happened in the park, is another offence. Plus at no time have you said you were coerced or forced into these acts of depravity."

He looked at me sternly as he went on. "Would you like to get a criminal record and maybe spend some time in prison, or would you rather just forget the whole thing?"

The Detective finished with "In this town, prostitution has been eradicated. We have worked hard to get rid of this crime, so I warn you against this route as you will soon find yourself in deep water!"

I left the police station and headed home. As I walked in the evening air, I could feel the skirt sway and also flick up with the breeze. As a form of pyric victory, I noticed I could walk pretty well in the four inch stiletto heels.

Arriving at my flat, I realised I didn't have my key so had to call on the caretaker John. He was about sixty years old, had been the caretaker for years and was a bit weird.

John opened his door and instantly recognised me as "Hello Tara, I haven't seen you in a long time. Everything OK?"

In my best Tara impersonation I replied "I have lost my key and need to get into the flat."