I came from a Youngstown OH, my family was really poor growing up and life history wasn't easy. My father moved out and left us when I was only 10 and my mother supported the family working at a supermarket during the day and bar attention at night. Since I was really goodness at math and managed to get a erudition to Ohio province I found a way out. I got a degree in math with a focus in statistics. I applied to jobs all over the country and got a few practiced interview lined up in NYC. With the little money I had from my late night working at a bar I flew out to NYC and interviewed with some small hedge stock. I left behind Regina, we hooked up and had a lot of capital sex but never could really take up dating with college and everything.

I was nervous but confident at the same time about this motility. I had a few cycle of interviews with HPQ consultant and finally I got the job as an analyst. Starting salary was $ 65,000 with carrying out based bonus. My initiative calendar week Reginold, went by Reggie told me the bonus aren't the only way of getting extra income, Ronnie the proprietor likes making little stake here or there with staff.
NYC was neat minus one thing, the cost, I had found a two-bedroom apt that one bed elbow room was for rent but it was $ 1,300 per month and I had student loanword of $ 800 per month. Long hours, eating out and socializing left me no room to give up from my cash flow.

I was in the bathroom one day and noticed Ronnie was in there washing his hands as I was."Hey kid you new here ?"he asked. I nodded,"my public figure is Ryan ”."Ah, yes Ryan you were the one that suggested the recent shift to healthcare sector, which has worked out quite nicely."“ Yes, sir that was me."“ Well why don't you meet me for tiffin at Bobby Tans 1 pm sharp."

Wow this is so exciting, I get to eat with Ronnie, he was loaded. We sat down and I listened to him and two other business associates talk about various topics, most of which made my stomach turn since it was all about how to easily ingest advantage of the poor in the commonwealth etc."So, you like healthcare right now, which farm animal in item boy ?"“ well sir Valeantz looks like a enough buy right now it is trading at 228 but my calculations show based on its momentum it could easily go to 300."“ Is that flop boy, how about we bet $ 20,000 on that he said ?"I choked on my drink and everyone burst out laughing at the table myself included.

"Boy let me reword that, if it hits 300 per share you get $ 20K, if it hits 100 per share you stop dressing as a man and embark on dressing like a woman in the office."He had a dark look on his face, the other two gentlemen were quiet and looked intimated. I reached out and shook on it. It was worth the peril for me plus it was trading above 200 it would need a 50 % plus commit back to hit his figure. Come by my office when we get back and we will work out the specifics.
I had a short bit of a bad feeling but still confident I could get that $ 20k to pay off my pupil loans as I walked into his spot. I sat down in forepart of his desk,"My boy, we need to work out these contingent, let me ask, I looked over your CV, where you are from etc, how often do you owe in student loans and how about that as the wager ?"“ I owe $ 80,000, you'd be willing to bet that much on one farm animal ?"“ Absolutely boy, how lots do you need on top of that,"“ How about $ 100,000 plus the $ 80,000 if you want me to walk around like a charwoman ?"“ Sounds like a program, let's do this, $ 500,000, if you win you get $ 500K, if you lose, you become my slave for sexual favors with me and my friends, you will look like a woman, seduce up, little operating theatre here or there, power slut type look, we lost Heather live month and she was the office roll in the hay toy, so I am looking for another one and you fit the build."“ Are you out of your mind !"I exclaimed,"$ 1 million in that eccentric, you would be able to help your crime syndicate back home and what are the hazard the stock drops to 100, in fact make it 90 and you have to hit 275 ? suppose about how easily you can wee your life groovy ! Deal or no deal no thinking this one over end of story."I took a deep breath,"Deal !"we shook hands, his right man Robert spoke up,"ok boys, we have a bet here for a orotund sum of money, I will muster in up the sound paperwork and have you both sign tomorrow bonny enough ?"We both nodded.

My heart was racing as I walked back to my desk, Reggie asked me what was wrong as I looked flushed. I explained to him the wager. He explained to me, that Ronnie loved to attain those stake, he had won a exchangeable bet and make $ 100K on the batch. I felt much better, I closely tracked the stock for the few month it hit 257 before quickly plummeting to 175, I thought I was going to cry, when it rallied back a niggling but there was all this news about scandal going on etc. succeeding thing I know my heart sank and my bollock pulled up, 110, 100, then it happened it closed at 75. Henry M. Robert approached me, Ronnie would like to see you in his office.

I took my walk of shame, waiting inside Ronnies office were a few adult female with clothing racks etc."My boy, you win some you lose some, I didn't even see that coming this quickly but I also didn't see it hitting $ 275, best way to study is to get you clump kicked in. In your case, literally, now Renee make him expect pretty,"she looked at me,"semen with us to the women's footlocker elbow room in the gym downstairs."My heart was racing, these three beautiful women walked me to the women's locker."Strip down, let's see what we are working with."I turned beat red, I am 5'9"and weight 150 lbs with a lanky body frame."dance step in the shower, and plane your all your pilus but your foreland, make sure you get your asshole too,"They handed me shaving cream, torso lavation and shampoo. I took the exhibitor and shaved everything and just stood there, my god what have I done. The charwoman asked me to propagate my boldness, I did exposing my rosebud,"Make for certain no haircloth is there, now shave it again."They weren't joking around this was for real.
When I stepped out they dried me off and started applying war paint and put a wig on. I had a robe on and they gave me a lacey G-string and bra. We went back up to the situation I went in through the back into Ronnie's part."Ahh there is my win, let's get you into a nice appropriate office attire."He made me model different clothes off the rack settling on 1.5 inch heels, a Shirley Temple Black wearing apparel with a tight Edward White button down. He had the charwoman leave the role and he sat on the lounge."clip to begin paying up boy, hope you like rooster because you're going to let a lot of dick in your life sentence going forward. I will take sure you are well taken care of, just get ready to chug a lot of pecker"

I looked into the mirror and started to cry, I went from a pretty good looking guy, to a blond bimbo in one day. With that he unzipped his pants and pulled out his member. I protested as I cried,"Ryan, no one likes a blow job where the womanhood is crying before they even gag. Now you made this bet and could get become copious, it was worth the bet for you and this is worth it for me. Now if you don't control up your end, go back place and start working at the supermarket where your mom is because snog any other career soundly bye. I can easily end you and your family from any normal macrocosm. Now open up and solve you tears !"

I wiped away my tears and approached his crotch, I looked down at his flaccid penis maybe about 5 inch slightly thick."That a girlfriend, he said, now suck this like the loose woman you are."As he said this he grabbed the back of my head and lined it up with his dick."Relax girl, slacken your breathing, my shaft will grow inside your mouth but I will slowly bob your psyche up and down nicely."I pushed my clapper forward toward the tip and licked it. To my surprisal, it didn't appreciation bad, it was rather salty. I did my best impression on what I say from the pornos I've watched and took the top dog in fully. He moaned in banker's acceptance and I just bobbed up and down slowly working in as many inches as I could.

"spirit up at me, I have to see you with my cock buried in your passably picayune oral fissure, you realize there is no way out but to do a good job."I stared up at him, tears still building, bobbing up and down as I felt his cock slowly growing inside my oral fissure.

I just wanted this to end, I bobbed furiously, my hands caressed his bollock, loudly slurping sounds came out of my mouth. He put his script behind my head and I felt him force down harder, his dick must cause been about 6 - 6.5 in now and maybe 1.5 inches wide. I might ingest been down 4 inches when I felt his tip slam against the back of my pharynx causing me to gag. He had shoved my promontory down and with both deal behind my psyche held me tight. I continued to asphyxiate, tears streamed down and spittle flowed from his mouth. He buried my font into his pubis and release quickly allowing me an opportunity to breath as I gasped for air. While trying to catch my breath he just kept pushing down my head as I dodged his dick, rubbed my spit all over my face.
"Isn't life history funny, one day you're some popular college kid banging girlfriend the next you've got your head buried in some honest-to-god man's crotch while you choke on his cock and the day after that two dude are using you like a Formosan finger's breadth trap ! Now take that cock again and sallow my cum before I shove it in your ass !"With that I realigned my sass over his cock and his thrusted it into my oral fissure. Gagging noises followed as I fought to come through this Assault on my mouthpiece. He furiously fucked my face for about 5 min before burying my face back down and pumping heaps of salty slimy cum into my belly. As he let go I choked and gasped for air. He pulled his pants up and sat back at his desk as I struggled to get to my groundwork.

I looked in the mirror, I looked like a mess. He threw a towel to me and called for Renee to follow in."Oh poor baby, well piece of work on that gag reflex so you look like less of a whore when you're done. Here is your travelling bag with you outfit for tomorrow. Please see Dr. Regario following month on the 15th at 10 am. Here is his card. He has a little oeuvre to do on your nothing John Major just a few particular of study. In the meantime, you are to fill these oral contraceptive pill, they will make anal and other body process hurt less. Lastly here is a bag with sex toy's butt plugs from 2 inches to 6 inches that will dilute your ass for anal sex, please work up to these"Ronnie stood up,"Now head home kid, it's getting late, get a undecomposed nighttime's rest to let this locate in."

For the future calendar month, I came into work dressed as a cleaning woman, Reggie just nodded with a shit happens around here form of flavour. No one seemed shocked at all. Reggie mentioned that same shit happened to heather before she left. My roommate didn't say much, a bit confused at first but I explained the deal and he said he would have taken the heap too. I was really moody and trouble, but Ronnie didn't do anything else that was sexual. I gained a bunch of weighting probably from eating and being depressed. I noticed on my calendar the Doctor's appointment was for tomorrow.

The next morning I took my sentence getting up, showered, got set and put on my blonde wig for the day. I arrived at Dr. Regarios office at 10 am and filled out a caboodle of paperwork and consent variety. I was called into his office. He reassured me everything is reversible, per Ronnie's parliamentary procedure there was a little work he wanted but aught major. I didn't even want to do it what he had in mind. He laid me on the table and gave me some gas as I slowly fell asleep.
I awoke in an awful total of pain, dazed and confused as to what just happened."Ah our patient role is finally coming too."Dr. Regario exclaimed. I slowly tried to sit up, my human face hurt, my pectus scathe, my ass hurt. As I looked down there was something on my chest blocking some of my view."Ohhh my god, what the fuck did you do !"I yelled out. They gave me breast implants ! What the fucking !"I'm going to fucking kill you !"I screamed out, quickly security came into the room and held me down. Dr. Regario walked forward."Ryan, listen here, I have orders paid for from Ronnie your boss, along with respective documents signed by you as part of a bet you two made, he does this ca-ca all the clip. He ordered, fag implants, lip injections, eyebrow lifts, hair implants, lazer hair removal, ass bleaching and cleaning, calfskin implants, knocker implants, emasculation and liposuction, most of the fat from your mid-section and coat of arms in now in your ass. I do sustain to say you came out pretty damn hot though !"

My heart sank and I passed out. I awoke again."That happened a lot around here, perfectly normal. Those hormone you were taking really helped in making your titmouse two-base hit ds by the way, they gave us just enough tissue paper around the edges."I thought I was dreaming earlier until he made that comment. I just started to cry."Doctor you can't leave me like this, I am a man, I can't go home like this."The Dr looked at me"Well the key word is, was, not, am, you were a man, after we cut off your balls you just have what Ronnie call's, a sissy button left that can't green goods sperm. And all these papers here protect me, you should read more carefully when betting with Ronnie."

Oh, my god, they cut off my balls, I couldn't process this right field now, strangely it didn't hurt. My will for getting upset was gone, I had no intuitive feeling.
Renee was waiting in the lobby for me as she helped me gather my belongings and escorted me to her car. She drove me nursing home,"So is some agitate to see how their beautiful new consistency looks."I said nothing just sat there crying."Ryan or Reann, take the side by side month off for recovery, Ronnie has deposited $ 50,000 into your accounting to console you. Take it comfortable, we will commit intellectual nourishment over and everything to ease your retrieval. These DVD's are for you to follow and condition that ass by the way."My roomy was shocked, and just didn't say a word as I walked in with bandages and the obvious transformation.
About a month later I got ready for study, I really did take care hot, huge tits, fat ass, big backtalk, small-scale waist everything. My stopcock used to be around 6 inches now barely 5 and skinny when laborious. The DVD was fully of sissy sex and hypno, I used my dildos and butt sparking plug. For some ground the dildos really made me cum and regular porn did nothing, probably the pill.

When I arrived back at work I got a lot of looks. I went to my desk and cried. Reggie came over,"Reann, it's not that bad, you look so pretty, you should be happy. Ronnie wants to see you after work."

right hand as everyone was leaving for the day I walked into Ronnie's office."My god you look beautiful ! Let's test those sassing out."He said as he undid his pant. I walked over and got on my stifle, I took his cock in my mouth and bobbed up and down slurping this sentence taking it all no job."someone has been practicing I see. God those brim make it so much best"because of those back talk drool was sliding out around his rooster and running down my face.
right hand after that I heard the room access open and the cleaning gang came in, I immediately stopped and pulled off sphacelate. Ronnie grabbed my forefront,"Don't stop consonant beloved ! Hey you two stay a while, isn't she pretty, this is Reann, remember the young guy that works here this is him after surgery."He just prevent pumping and a few moments later he pushed my head all the way in and fritter a load deep down my throat. I whipped my face for cum and expectoration.

The two Spanish men just laughed. Ronnie told them,"Hey no one has ever broken him in, I am his first dick, how about you two help me discover him in. His ass has to be tight as Hades, reckon it an early Xmas present."I could see them walking over as Ronnie let up on my heading.

The two men smiled, with a Spanish accent they said,"holy shit Ronnie, this was that young new guy, my god you gave him the hottest set of titmouse an ass I've ever seen on a chick, let alone a dude. I'm not gay, but fuck that ass looks juicy as hell and those lips were built for sucking cock."Ronnie looked to them,"don't worry it's only gay when there is a cock in your ass, Reann is the only one in the room that will have one up her cunt !"

I looked at them one was magniloquent maybe 6'3"the other one short and fat maybe 5'6"both Spanish and form of grimy looking. They both started unzipping their pant when two fat turncock plopped out. My oral cavity dropped and I looked at Ronnie,"But they are too big ?"“ Not for my little jade, up on the desk you go, and start sucking."I stood up and the two men pulled my skirt and panties down, I froze, they unbuttoned my top and took my bra off."Wow look at those tits !"They pushed me and bent me over the desk. The tall one walked in nominal head of me and started jerking his dick, it was getting severely maybe, 8 or 9 in and really fat. He pushed it into my mouth, I gagged and slurped. The early one started eating out my ass as I moaned. The guy behind stopped licking and walked around with Ronnie,"takings a look at this hunk of meat Reann ! And suck that big fat dick !"

As I looked up I thought to myself how is it the unretentive guy has the biggest cock. It was knockout maybe 10 inch and as thick as my wrist. Ronnie made me take turns between the two sucking them furiously, chocking, gagging, spitting. The dead one walked back around as Ronnie was lubing up my ass. I didn't notice much, moaning from hurting and delight while trying to survive the cock in my mouth. The tool in was meeting electric resistance when it finally pushed into my throat as I chocked and gagged. He pulled back out as I gasped for air and then jammed it back into my throat.

When I felt the cock head at my ass, I tried to dissent, screaming but it was silenced into the cock in my mouth as I gasped for air. It pushed against a lot of resistance on my ass but popped past my anal ring letting the head in. I screamed in bother again silenced into the other man's crotch as I tried to squirm. A wafture of chagrin, painful sensation and pleasance swept across me. He just kept pushing, additional tears flowed down my cheeks."Roque, this ass is so tight, it's like Eden man you got to try it soon ! Now I am going to wreck this Andrew D. White art object of ass thought fucking clean this up White boy !"He shouted thrusting about 5 inches in as I jolted forward on the desk, kicking my ramification up in the air.

It felt like my insides couldn't accommodate any more when another column inch when in. My insides felt like they were being ripped apart. My grimace plowed into the early man's prick showing no escape from the stopcock. He pulled out and rammed it back in getting maybe 8 in in, pulling out again before ramming me into the former man's putz again as his musket ball slapped against my little cock that was just dangling there.

"Wow this is quite a sight, your cocks are impaling this fiddling young woman on both end like an accordion ! Why don't you lift him up ?"With that I tried to protest but nothing helped, they lifted me off the desk and flipped me upside down rotating me in midair, I tried to complain and push a little but they clamped my legs down under the man's axilla and locked me in place, the short guy lined his cock up again and thrusted in as I screamed out in painful sensation. The other man silenced me quickly ramming his cock down my throat again and they two fucked me furiously."My god look at his little pecker bob around, after all those internal secretion and removing those egg its lupus erythematosus a cock and More of an itsy bitsy sissy clitsy !"All the men laughed while I was mercilessly railed out on both ends. Siliva and spit ran down my nerve the man in my mouth let out a gimcrack moan holding his cock buried down my pharynx releasing stream after stream of hot green of cum into my belly.

He stayed there as I continued to chock on his cum and stopcock. The other man firmly grabbed men around my waist also letting out a burden moan, pulling me toward him as hard as he could."Oh my god what a fucking astonish ass, I going to meet you up !"He shouted as I felt crack after shot of hot jizz shoot deep into my ass. He pulled back out with a pop, making my ass feel empty and then slammed it right back in as I let out a yelp."Ohh god that ass was amazing."He exclaimed, the man slowly withdrew his cock from my ass as the early guy pulled out of my rima oris. I could feel a stream of cum trickeling out of my ass. I collapsed on the desk after they let me down, expel, ashamed and humiliated as I lost my anal virginity.

I heard the door open again, I could get a line Renee talking and I knew the other vox too. I glanced over and saw Regina talking to Renee, what the blaze was she doing here in New House of York. Ronnie walked over to my hitch consistency,"Reann, Ryan is a skilful analyst, but you, god can you take a cock, Regine, glad you could pass water it today."Regina looked appall to see the scene in the role."Regina, I believe you might experience this minuscule light-haired bimbo lying here, this is Ryan, now Reann, he made a bet and let's say he lost more than just the stake, how do you like the transmutation ?

I covered my cheek so as to not see her, she walked over."Ryan is that really you ? Ryan it's me Regina, holy crap they really did have you a woman."“ Don't look at me please Regina."“ It is you I can tell, wow they did some work with you, I guess you really have changed. I am sorry love but Ronnie is paying me a lot of money to do what I am about to do, please forgive me."As I looked up I could see Renee getting a strap on dildo prepare and Regina was stripping down.

"Reann, to really erupt you in I needed downright humiliation, you didn't seem to experience a heights school odorous kernel and Regina appeared to be the closest thing, everyone has a price, and we found hers to bang an old friend with a strapon dildo. With that he slapped my ass and told the two care guys to get out.
Renee was helping Regina get on the large strapon. I pleaded and cried,"Regina please don't do this I can't watch you fuck me like this you can't !"She approached lathering the dildo in lube, Renee and Ronnie lifted my legs up in the air exposing my cum dripping ass."Reann, you're a womanhood now, your not the guy I used to get it on, now stop being a little pansy about this and take this pecker !"She said as she pressed the dildo head against my ass. This was beyond humiliating, I used to fuck her and always wanted to try anal but not like this. As she pressed harder breaking the barrier of my already loose trap she said,"Reann, remember when you wanted to try anal retentive, well I'm about to split you in half my little sissy."With that she pushed her weight as the dildo sank in slowly.
Renee spoke up,"Reann encase your wondering this is a 10 inch dildo that is made for prostate massages with a curved tip, it is about 2 in in diameter right around the midriff, or simply put, we don't expect you to follow in tomorrow after Regina splits you ass in half, and you're about at the thickest part."Right as she said that Regina withdrew the moth-eaten dildo and shoved it back in as I let out a yip, she just kept bucking into my ass. Pounding away, verbally abusing me about what a pansy I am."Ronnie, face what you did, his lilliputian pantywaist clitoris is dripping precum soft and flopping around while his huge breast just bounce around. You do big workplace I must say !"

I looked down liquidness was flowing out of my cock as it danced around, I felt a wave of delight building up in my ass. I started to moan, what was happening to me. My moan and panting grew louder as her dildo bucked against my hips, she was fucking me like a wild woman while Ronnie and Renee cheered on. I could only expect up at the faces as they stared in a spell at the Brobdingnagian dildo ripping my ass up."Oh gawd, oh gawd,"I yelped out as I felt like I was about to erupt when all of a sudden my cock started to let out a stream of cum like a faucet, it pooled all over my stomach.

"There is goes, he fucking came like the little effeminate slut he is, only cumming from now on with a nice house dick up his ass !"Renee exclaimed. Regina kept fucking me for a few Thomas More minutes as I bucked around in pure Adam. It was too a lot I collapsed as she kept fucking me. I finally came too as they were all dressed and I was still naked on the couch now.

"Reann, I am sorry I guess you must have just passed out and in the high temperature of the moment we didn't poster. Are your ok."Regina asked. I nodded to them Let's get you dressed and out of here she said. Ronnie and Renee were heading out,"Hey Reann lock up and get the fuck out, take the day off tomorrow, you've done enough work today."

Regina and I went out to dinner, I was ashamed and told her the whole story. She explained how they called her out of the blue and offer $ 100,000 to fuck you and an extra $ 50,000 if I really humiliated you. I didn't blame her for taking the business deal. She felt bad but a bet a bet and she missed the old me. She did need to fuck me again, she said it gave her a lot of power, she also wanted to see a guy rail me out, perhaps my roomie, dead reckoning I know what I am doing tonight at my apartment.

The end for now !