Thirteen Tasks

August 9^th 2017

What an incredible day, oh yes that's right, I need to introduce myself my name is Eric Myers, and I am 28 years old. Today the most incredible thing happened, there I was minding my own business when I got a call from an unknown number saying I had been chosen for a special reality contest where the Winner would become a Multi-Millionaire. Now of course I was sceptical but the caller knew exactly who I was and even where I was, now admittedly that came across a little creepy but who am I to argue, I've always wanted to be a part of a reality competition and the game seems quite simple.

"All you have to do is complete 13 tasks, all of which reward you with a sum of money and if you complete all 13 tasks you will be the winner of the grand prize, however failing to complete any of the tasks results in losing all the money you have earned up to the point. Thus is your last chance to back out Mr Myers, your first task is very simple and that is to take a picture of yourself which also acts as your application form, doing this will earn you 100 to be deposited in your bank account so Mr Myers do you accept?"

Like Hell I accepted, easiest 100 bucks I've ever made in my life , yes I was a little weary at first but I had nothing to lose and low and behold after completing the task my bank balance was credited with 100 into my account, sweet. Who knows what fun tasks I'll have to do in the future, besides I'm currently unemployed living at home and in dire need of an adventure, plus the money couldn't hurt, life is finally looking up for me.

August 10^th 2017

Okay so it looks like things may not exactly what I anticipated but I think I'll be ok. My next task came in today in which all I had to do was take another picture except this time I had to be naked in the photo, definitely not what I was expecting at all, I sure didn't expect nudity to be a part of this game but I was assured that this game was all about pushing myself to my limits, building confidence and giving me the power to do all the things I've ever wanted to do but was too afraid to do. Besides this task was worth 250 and while I have zero confidence in my body and I was a little weary of what this picture would be used for or what it meant for the future tasks, I got up the courage and took the photo, after all its hardly going to do any harm and it really was easy money and to be honest I do feel more confidence in myself than I had before.

So what if the game involved nudity of some sort, hell honestly if I can become a Millionaire by being nude, that's perfectly fine by me. I wonder what tomorrows task will consist of.

August 11^th 2017

Looks like the game is heating up, task no 3 was pretty simple really, just book a hotel for myself away from home for the weekend and I will win 1,000, whoa this game is fun thus far and its only getting started. The money from the last tasks will more than help fund the hotel until I get my next amount which I will receive once I arrive at the hotel, I wonder what tasks I will have to do but the excitement is building and I have been wanting a weekend away for some time now so this is a win win.

August 12^th 2017

I am finally here and so excited to begin this day , I have been told to get myself sorted, get something to eat and prepare for my next task I am just so excited to get things truly started.

So remember that excitement I was telling you about? Yeah this game might be different than I anticipated, my 4^th task was not what I expected

"So Mr Myers I assume you are well fed and have settled in to your hotel room, now the real fun begins. You will follow the directions to the store I want you to go to, once you are there, await further instructions"

That part was just normal like usual until of course I got to the required location which was an Adult store. I had never ever been in one before so I will admit I got hard the minute I got to the shop as I wondered what was going to be my task here but I didn't have to wait long as I received the text that I was waiting for.

"Now that you are here your task is very simple, all you have to do is purchase an outfit and some toys for a very special lady. All you need to get is a sexy outfit, a Dildo, butt plug and lube of course."

Taken a little off guard as this game has suddenly become rated R I couldn't help but still be quite aroused at the prospect of what was to come so I did as was instructed. While I had no idea what to actually get I sure as hell didn't want to make any mistakes and fail the task so I had a quick look around to see what to get while also getting over my fear of the man at the counter thinking I was buying all these things for myself as I definitely don't swing that way though I couldn't help but get turned on by all the sex toys around me. I bought an outfit, a nice slutty red one (I so hope I get to see the girl who wears it) a nice 8 Inch Dildo with suction cup, a medium butt plug and 2 bottles of lube. Somebody is going to have some fun later though I still can't figure out where I fit onto all this as I am kind of worried as to where this is going to lead especially the butt plug as that feels like it's more for me but that can't be right plus everything else clearly states a women is going to be involved so I definitely have that to look forward to.

So I arrived back at the hotel and received another message instructing me to take a shower and just as I was ready I got a call that really made me comfortable

"Task number 5 for 2500 is here, all you have to do is take a nice shower, included in the shower are razors shaving cream and lotions to get your body super smooth for the entertainment later on, of course you can always back out of the game though that will mean losing all your money so far and since you have paid for this hotel room and bought quite a bit at the adult store that may cause you some troubles. Never fear, there really is nothing to worry about, nothing wrong about a guy who is clean shaven plus I can already tell it has you quite excited"

I will admit I blushed as he said those words because despite my predicament I was hard as a rock and admittedly being shaven all over wasn't the end of the world as the hair would grow back plus it's not like I've had a very active sex life up till now so it should be ok, after all I am getting 2500 for doing this so I might as well go ahead with it.

Yeah things have gotten worse, admittedly that was very nice soothing shower and I feel so smooth and I was turned on throughout when I got out I realised my clothes were gone, I searched all throughout my room and while nothing else was missing all my clothes were gone, all that was left was the outfit I had bought earlier which was really nothing more than a bra, panties, stockings and a pair of high heels and of course I still had it in my head at that time that the outfit was for some girl, oh how I was naïve as I'm sure you can probably guess by now where this story is heading as I finally got a text explaining the situation in a way that while a turn on slightly horrified me.

"Task number 6: Put on your new outfit Mr Myers or should I say Ms Myers ha-ha, I have also prepared a long black haired wig for you as well as inflated the chest of the bra you will be wearing, Complete this task and you will win 10000."

I'm pretty sure I was white as a ghost after reading that text, there was no woman, I was the women and here I was tasked with wearing that outfit which could only mean that those toys were for me, still thought for whatever reason it caused my dick to get hard once again. There was no way I was using those toys but yet this was only task 6, things were only going to get worse from here but stopping now wasn't an option, it's not like I could leave without my clothes plus if I took things step by step I knew I could get through this after all I would receive 10000 for just putting on the outfit which did nothing to remove my arousal, pre cum probably soaked the panties I had to wear. There I was 10000 richer as I checked my bank balance and awaited the nest task in fear, after all here I was in a hotel room dressed as a woman with sex toys in my possession and 7 tasks more to go, what could possibly go wrong? I couldn't back out now, I was already too far down the rabbit hole as I nervously awaited my next task just as my phone rang.

"Ah Erica, you are doing wonderfully, I am here to give you not just your next task but your next two task and they both earn you 25000 each, task number 7 is to lube out that boi pussy of yours and insert the butt plug up your ass, make sure to use plenty of lube. Task number 8 then is pretty simple, With the butt plug still inserted I want you to stick your dildo on the wall at the correct height leaving on your knees sucking on it for the foreseeable future, you mustn't stop until I give you your next task, I want you to give that dildo a thorough sucking and make sure to practice your deep throating skills, you will gag a lot at first but practice will make perfect I promise"

What was I to do? I have no choice but to obey, I don't know why or what is going on with me but I am finding this whole ordeal to be quite arousing as frightening as it may be, I'd be lying if I told you that I wasn't curious to try out the toys after all a guys g spot is in there ass and it's not like I will be sucking a real cock so there I went and lubed up my asshole as well as the plug and gently pushed it up my ass, it was weird at first and even a little painful but then it was quite pleasurable and my dick was rock hard at this point. I have to admit the full feeling was a huge turn on as I fastened the dildo to the wall and got down on my knees prepared to suck on the dildo wishing I had bought the 6 inch one but nope I had to buy the 8 inch one. I started by licking the dildo and gently pushed it in struggling not to gag on it as I tried my first deep throat, I was sucking on it for like 5 minutes rock hard and still couldn't manage any more than about 2-3 inches in my mouth at one time, as much as a turn on as it was I was hoping my phone would ring but another 5 minutes had passed and still nothing, by now I could actually get the dick in my mouth all the way to the balls and it felt amazing, at that moment I didn't care what came next or why this was happening or who was behind all this as I was having the time of my life. Suddenly the phone rang and told me to remove the butt plug as it was now time to ride the dildo for 50000 I just jumped on it, it was amazing my ass against the dildo, I couldn't possibly explain the feeling of when the dildo was first pushed all the way into my ass other than it was like the best sex I have ever had and then some, I didn't care what was going anymore I just wanted to keep fucking my ass and stroke myself till I came but unfortunately I was prevented from stroking.

I had my next call while I was riding the dildo much to my caller's amusement as they gave me my horrifying 10^th task

"I'm sure you will be pleased to hear that I have posted an add on craigslist for you and even arranged everything for you, since you enjoyed tasks 8 and 9 so much I thought it was only fair than 10 and 11 were with the real thing, somebody will be at your room in 10 minutes looking for a blowjob in which you will swallow his cum and after that another man will be there to fuck your virgin ass, enjoy sissy"

Ok so now the time panic really started to settle in, I couldn't do this, this was all fantasy, not reality, I will admit that the toys were fun I am not gay, yes iv long realised that I will do a lot for sexual pleasure and I still super turned on but this was different but as I contemplated my situation I got a text with a link to a video clip of everything that went down so far in that hotel room, it was all going to go public, I had no choice, I had to get ready and brace myself as fantasy was about to become reality, I was going to give my first blowjob and lose my anal virginity and there was nothing I could do to change that, besides there was always part of me that wanted some excitement in my life and for fantasy to become reality, besides once these tasks are over I can take my money and get away from all this.

I had no choice, my heart was beating faster than ever before, I had butterflies in my stomach the size of eagles, all the adrenaline going through me I could hardly think straight and then there was a knock on the door, this was it, the moment of truth.

It went better than expected to be honest, my main issue was what the smell of cock was going to be like, after all a Dildo is one thing but an actual Cock is another matter altogether, the man arrived, smiled and dropped his pants and said "Well suck it bitch not I haven't got all day, thankfully he didn't seem to be in the mood for anything else as I certainly wanted nothing more than just to suck his cock and get him out of there but once I got his dick inside my mouth and his moans began I have never felt as hard in all my life, yes there was a smell but and musky taste but that was quickly replaced with my saliva as I sucked his cock form base to tip while also stroking him at the same time, he was a bit smaller than the dildo I had practiced on which was a relief, I even surprised myself after with thoughts of happiness and this wasn't the guy that was fucking me as I wanted a bigger cock for that. Oh who am I kidding I'm an official sissy now, It was only a few minutes before I made him cum and I swallowed my 1^st load, I had satisfied him and it actually pleased me, what the hell has happened to me, I wasn't disgusted with the load like I thought I was going to be, all I wanted was to cum but I have made it so far, I wasn't going to stop now, the man pulled up his pants and left saying "I hope we can do this again sometime."

So task 10 down only 3 more to go and I was free and I knew what was coming, I got cleaned up and prepared for what was to come. I was so horny I desperately needed to cum, I rushed to the door the minute I heard a knock and awaited the next man, he was bigger than the first and nice again to my surprise all I could think of was that I hoped his cock would be big enough and I got my wish, it must have been 8 inches and just like the first guy he wanted me to suck his cock and I couldn't even think to argue I was just to horny I got my knees once again and did my best to give him a blowjob of a lifetime, I never even stopped to think what I was actually doing and before I knew it I was on the bed panties down ass up on all fours ready to lose my anal virginity.

My god was it 100 times better than the Dildo, every thrust was pure bliss, my cock rock hard feeling like it was ready to burst, just when I felt like I would finally get to cum from anal alone he pulled out turned me out and give my 1^st facial, I was stunned but there nothing I could do.

"That was awesome slut I hope to hear from you again" he said as he left. Shocked after the realisation over what happened I didn't even get to react before the phone rang.

"Ah Erica what a fine slut you have become the only step now is two cocks at once, or maybe 3, no 4, ah I know what would be perfect for you, A Gangbang, get showered up you are going to the hotel room across from yours to be the entertainment for Party, enjoy."

All I could hear after that was laughter followed by the sound of the call ending, why did I ever think things would be so simple, what could possibly be the final task if this isn't it, the thought while horrifying I would be lying to say if the prospect wasn't at all arousing, my hard on still hadn't gone away, I was desperate to cum, I had no choice I had come way too far to back out now, I got ready and prepared myself for what was to come.

8 cocks, 8 of them were waiting for me, I knew it was going to be there a while but I had no idea what they had in mind, first I had to do a little tease and then they brought out a table and held me down to it and tied me face first on the table, I was trapped with no choice but to suck off those at my face and take all cocks up my ass, I hoped it was just going to be over quick but no such luck, they all took turns getting warmed up with a blowjob and then fucking and Cumming in my ass while the next person moved in for his blowjob, once I had sucked off the eight guys and was getting ready for what I thought was my last anal fucking, the first guy had come back he was ready to go again, I honestly lost count of how many blowjobs I had to give, how much cum I swallowed, how many times I had been fucked, not only did I finally cum but I must of leaked buckets of precum and even came multiples times just from anal alone, it was finally over, I didn't even get more than a towel to clean up with as I gingerly made it back to my hotel room as I awaited my final task, I would soon know what separated me from becoming a Millionaire, the nerves were high but after everything I had been through I knew I could do anything, another gangbang? Easy I thought to myself and once it was over I could forget all this had ever happened, I just hoped I would never have to relieve any of this ever again and that nobody would find out, it was a part of the agreement after all, as I re-entered my hotel room I got my last message, my last task and there was a box on the bed. This was it the moment the moment of truth.

I read the message with simply stated "Inside the box is your final task, failure to do so means that your most recent hotel activities will be broadcast on all your social media sites as well as on the top porn sites"

This was it, I had no choice but to follow this task and it would all be over at least that's what I thought as I opened the box and realised what my final task was as I looked at the chastity cage inside

"Put this on and yes I have the key, it will only open once you have completed Phase 2 of the game"