I came from a Youngstown OH, my kinfolk was really poor growing up and life 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 tending at night. Since I was really well at maths and managed to get a scholarship to Ohio State I found a way out. I got a grade in maths with a focus in statistics. I applied to jobs all over the state and got a few thoroughly interviews lined up in NYC. With the minuscule money I had from my recently night working at a bar I flew out to NYC and interviewed with some low hedge funds. I left behind Regina, we hooked up and had a lot of groovy sex but never could really start dating with college and everything.

I was nervous but confident at the like time about this movement. I had a few rounds of consultation with HPQ consultant and finally I got the job as an analyst. Starting salary was $ 65,000 with performance based bonus. My low gear week Reginold, went by Reggie told me the bonuses aren't the only way of getting extra income, Ronnie the possessor likes making petty bets here or there with staff.
NYC was bang-up minus one thing, the cost, I had found a two-bedroom apt that one bed room was for rip but it was $ 1,300 per month and I had bookman loans of $ 800 per calendar month. retentive hours, eating out and socializing left me no way to give up from my Cash flow.

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

Wow this is so turn on, I get to eat with Ronnie, he was loaded. We sat down and I listened to him and two other business comrade talk about various topics, almost of which made my stomach tour since it was all about how to easily take advantage of the hapless in the nation etc."So, you like healthcare right now, which livestock in particular boy ?"“ wellspring sir Valeantz looks like a decent buy right now it is trading at 228 but my calculations show based on its impulse it could easily go to 300."“ Is that right wing boy, how about we bet $ 20,000 on that he said ?"I choked on my drink and everyone flare-up out laughing at the tabular array myself included.

"Boy let me paraphrase that, if it hits 300 per part you get $ 20K, if it hits 100 per share you stop dressing as a man and set out dressing like a woman in the office."He had a minatory look on his face, the early two gentlemen were quiet and looked intimated. I reached out and throw off on it. It was worth the risk for me plus it was trading above 200 it would need a 50 % plus get out back to hit his number. 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 student loan as I walked into his office. I sat down in front of his desk,"My boy, we need to work out these particular, let me ask, I looked over your resume, where you are from etc, how much do you owe in student loanword and how about that as the stake ?"“ I owe $ 80,000, you'd be bequeath to bet that much on one stemma ?"“ Absolutely boy, how practically do you need on top of that,"“ How about $ 100,000 plus the $ 80,000 if you want me to take the air around like a char ?"“ audio like a program, let's do this, $ 500,000, if you win you get $ 500K, if you lose, you become my striver for intimate party favour with me and my booster, you will look like a woman, relieve oneself up, trivial surgery here or there, business office strumpet character feel, we lost Heather conclusion month and she was the office staff fucking 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 subject, you would be able to help your family back base and what are the hazard the ancestry free fall to 100, in fact make it 90 and you have to hit 275 ? Think about how easily you can make your life gravid ! Deal or no hand no thinking this one over end of story."I took a oceanic abyss breathing place,"Deal !"we shook deal, his right-hand man Robert spoke up,"ok boys, we have a bet here for a great sum of money, I will enlist up the legal paperwork and have you both sign tomorrow fair enough ?"We both nodded.

My eye was racing as I walked back to my desk, Reggie asked me what was haywire as I looked flushed. I explained to him the bet. He explained to me, that Ronnie loved to throw those bets, he had won a similar bet and stool $ 100K on the mass. I felt much better, I closely tracked the stock for the few months it hit 257 before quickly plummeting to 175, I thought I was going to cry, when it rallied back a little but there was all this intelligence about malicious gossip going on etc. future thing I know my philia sank and my balls pulled up, 110, 100, then it happened it closed at 75. 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 women with article of clothing stand 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, substantially way to larn is to get you balls kicked in. In your case, literally, now Renee make him look pretty,"she looked at me,"Come with us to the women's locker room in the gym downstairs."My heart was racing, these three beautiful women walked me to the women's locker."cartoon 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 torso frame."stair in the rain shower, and shave your all your hair but your foreland, make surely you get your asshole too,"They handed me shaving cream, body wash and shampoo. I took the shower and shaved everything and just stood there, my god what have I done. The woman asked me to propagate my cheeks, I did exposing my rosebud,"brand surely no whisker 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 make-up and put a wig on. I had a robe on and they gave me a lacey thong and bra. We went back up to the billet I went in through the back into Ronnie's office."Ahh there is my win, let's get you into a Nice seize billet attire."He made me sit different apparel off the rack settling on 1.5 column inch blackguard, a black wearing apparel with a smashed Andrew D. White clitoris down. He had the women leave the position and he sat on the lounge."Time to start paying up boy, hope you like tool because you're going to consume a lot of dick in your life going forward. I will make sure you are well taken care of, just get quick 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 blonde 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 woman is crying before they even gag. Now you made this bet and could let become rich, it was worth the bet for you and this is worth it for me. Now if you don't hold up your end, go back dwelling and come out working at the supermarket where your mom is because kiss any other career good bye. I can easily end you and your family from any pattern existence. Now open up and crystallise you tears !"

I wiped away my tears and approached his crotch, I looked down at his flabby penis maybe about 5 column inch slightly thick."That a girl, he said, now suck this like the adulteress you are."As he said this he grabbed the dorsum of my head and lined it up with his dick."Relax little girl, decelerate your respiration, my turncock will rise inside your mouth but I will slowly bob your head up and down nicely."I pushed my tongue forward toward the tip and licked it. To my surprisal, it didn't taste bad, it was rather salty. I did my intimately impression on what I say from the pornos I've watched and took the caput in fully. He moaned in acceptance and I just bobbed up and down slowly working in as many inch as I could.

"Look up at me, I have to see you with my hammer buried in your moderately little sass, you realize there is no way out but to do a unspoilt job."I stared up at him, rip still building, bobbing up and down as I felt his cock slowly growing inside my mouth.

I just wanted this to end, I bobbed furiously, my hands caressed his balls, loud slurping speech sound came out of my mouth. He put his hand behind my head and I felt him drive down harder, his dick must cause been about 6 - 6.5 inches now and maybe 1.5 inches wide. I might feature been down 4 inches when I felt his tip slam against the binding of my throat causing me to gag. He had shoved my head down and with both workforce behind my headspring held me tight. I continued to give-up the ghost, teardrop streamed down and saliva flowed from his sass. He buried my face into his pubes and loss quickly allowing me an opportunity to breath as I gasped for air. While trying to catch my intimation he just kept pushing down my head as I dodged his cock, rubbed my tongue all over my brass.
"Isn't aliveness funny story, one day you're some popular college kid banging girls the succeeding you've got your headland buried in some senior man's crotch while you choke on his cock and the day after that two fashion plate are using you like a Formosan finger trap ! Now take that cock again and sallow my cum before I shove it in your ass !"With that I realigned my mouth over his cock and his thrusted it into my mouth. Gagging dissonance followed as I fought to subsist this assault on my oral fissure. He furiously fucked my case for about 5 minutes before burying my face back down and pumping loads 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 pes.

I looked in the mirror, I looked like a pickle. He threw a towel to me and called for Renee to come in."Oh short babe, well oeuvre on that gag reflex so you look like less of a cocotte when you're done. Here is your traveling bag with you outfit for tomorrow. Please see Dr. Regario next month on the 15th at 10 am. Here is his lineup. He has a little piece of work to do on your zippo Major just a few item of oeuvre. In the lag, you are to film these pills, they will make anal and other action hurt less. Lastly here is a bag with sex toy's butt plugs from 2 column inch to 6 inches that will stretch out your ass for anal sex, please work up to these"Ronnie stood up,"Now head home base kid, it's getting late, get a good Nox's rest period to let this reconcile in."

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

The next morning I took my time getting up, showered, got fix and put on my blond wig for the day. I arrived at Dr. Regarios office at 10 am and filled out a bunch of paperwork and consent forms. I was called into his agency. He reassured me everything is two-sided, per Ronnie's parliamentary procedure there was a little piece of work he wanted but cipher major. I didn't even want to know what he had in intellect. He laid me on the table and gave me some gas as I slowly fell asleep.
I awoke in an frightful total of annoyance, 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 boldness hurt, my chest of drawers damage, my ass hurt. As I looked down there was something on my chest of drawers blocking some of my view."Ohhh my god, what the roll in the hay did you do !"I yelled out. They gave me breast implants ! What the shag !"I'm going to fucking kill you !"I screamed out, quickly surety 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 various written document signed by you as office of a bet you two made, he does this shit all the time. He ordered, butt implants, lip injection, supercilium lifts, hair implants, lazer hair remotion, ass bleaching and cleansing, calf implants, boob implants, castration and liposuction, nigh of the fat from your mid-section and coat of arms in now in your ass. I do have to say you came out pretty beshrew hot though !"

My heart sank and I passed out. I awoke again."That happened a lot around here, perfectly normal. Those hormones you were taking really helped in making your titmouse reduplicate ds by the way, they gave us just enough tissue around the edges."I thought I was dreaming earlier until he made that gossip. I just started to cry."physician you can't leave me like this, I am a man, I can't go house like this."The Dr looked at me"Well the key word is, was, not, am, you were a man, after we cut off your Lucille Ball you just have what Ronnie telephone call's, a epicene button left that can't produce sperm cell. And all these documents here protect me, you should read more carefully when betting with Ronnie."

Oh, my god, they cut off my balls, I couldn't mental process this right now, strangely it didn't hurt. My will for getting upset was gone, I had no notion.
Renee was waiting in the vestibule for me as she helped me gather my belongings and escorted me to her car. She drove me home,"So is some excited to see how their beautiful new eubstance looks."I said zero just sat there crying."Ryan or Reann, take the succeeding calendar month off for convalescence, Ronnie has deposited $ 50,000 into your account to comfort you. take on it easy, we will send solid food over and everything to facilitate your recovery. These DVD's are for you to watch and take aim that ass by the way."My roommate 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 work, I really did face hot, huge titty, fat ass, big brim, small waist everything. My cock used to be around 6 inch now barely 5 and skinny when hard. The DVD was fully of sissy sex and hypno, I used my dildos and fag plugs. For some reason the dildos really made me cum and regular porn did nothing, probably the birth control pill.

When I arrived back at work I got a lot of flavor. 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 as everyone was leaving for the day I walked into Ronnie's office."My god you look beautiful ! Let's examination those brim out."He said as he undid his pants. I walked over and got on my stifle, I took his cock in my lip and bobbed up and down slurping this time taking it all no problem."Someone has been practicing I see. God those lips make it so much better"because of those lips drool was sliding out around his hammer and running down my face.
right wing after that I heard the doorway heart-to-heart and the cleaning crew came in, I immediately stopped and pulled off humiliate. Ronnie grabbed my head,"Don't stop honey ! Hey you two stay a while, isn't she pretty, this is Reann, recollect the young guy that works here this is him after surgery."He just keep pumping and a few moments later he pushed my head all the way in and shot a incumbrance deep down my throat. I whipped my look for cum and spit.

The two Spanish people men just laughed. Ronnie told them,"Hey no one has ever broken him in, I am his first cock, how about you two assist me break him in. His ass has to be tight as hell, turn over it an too soon Christmas present."I could hear them walking over as Ronnie let up on my forefront.

The two men smiled, with a Spanish accent they said,"Holy shit Ronnie, this was that Lester Willis Young new guy, my god you gave him the hottest set of tits an ass I've ever seen on a bird, let alone a fashion plate. I'm not gay, but fuck that ass looks juicy as the pits and those lips were built for sucking cock."Ronnie looked to them,"don't worry it's only gay when there is a prick in your ass, Reann is the simply one in the way that will deliver one up her pussy !"

I looked at them one was tall maybe 6'3"the other one light and fat maybe 5'6"both Spanish and kind of grimy looking. They both started unzipping their trouser when two fat hammer plopped out. My lip dropped and I looked at Ronnie,"But they are too big ?"“ Not for my little loose woman, up on the desk you go, and start sucking."I stood up and the two men pulled my skirt and pantie down, I froze, they unbuttoned my top and took my bra off."Wow feel at those tits !"They pushed me and deform me over the desk. The marvelous one walked in figurehead of me and started jerking his dick, it was getting severely maybe, 8 or 9 column inch and really fat. He pushed it into my sass, I gagged and slurped. The other one started eating out my ass as I moaned. The guy behind stopped licking and walked around with Ronnie,"take a look at this hunk of meat Reann ! And suck that big fat cock !"

As I looked up I thought to myself how is it the short guy has the biggest cock. It was unvoiced maybe 10 inches and as thick as my wrist joint. Ronnie made me alternate between the two sucking them furiously, chocking, gagging, spitting. The short-change one walked back around as Ronnie was lubing up my ass. I didn't notice much, moaning from infliction and pleasure while trying to survive the cock in my mouthpiece. The pecker in was meeting resistance when it finally pushed into my pharynx 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 protest, 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 retentive ring letting the oral sex in. I screamed in pain again silenced into the former man's crotch as I tried to wriggle. A wave of humiliation, pain and pleasure swept across me. He just kept pushing, additional weeping flowed down my cheeks."Roque, this ass is so tight, it's like Shangri-la man you got to try it soon ! Now I am going to wreck this Andrew D. White part of ass thought fucking clean this up ovalbumin boy !"He shouted thrusting about 5 in in as I jolted forward on the desk, kicking my legs up in the air.

It felt like my interior couldn't accommodate any more when another inch when in. My insides felt like they were being ripped apart. My case plowed into the other man's rooster showing no escape from the cocks. He pulled out and rammed it back in getting maybe 8 column inch in, pulling out again before ramming me into the other man's cock again as his ballock slapped against my piddling cock that was just dangling there.

"Wow this is quite a sight, your cocks are impaling this little girl on both terminal like an accordion ! Why don't you lift him up ?"With that I tried to dissent but null helped, they lifted me off the desk and flipped me upside down rotating me in midair, I tried to kick back and bear on a little but they clamped my branch down under the man's armpits and locked me in topographic point, the shortly guy lined his cock up again and thrusted in as I screamed out in pain. The early man silenced me quickly ramming his cock down my throat again and they two fucked me furiously."My god face at his little rooster bob around, after all those hormones and removing those balls its to a lesser extent a cock and more than of an itsy bitsy sissyish clitsy !"All the men laughed while I was mercilessly railed out on both ends. Siliva and spit ran down my impudence the man in my mouth let out a garish groan holding his cock buried down my pharynx releasing current after stream of hot jets of cum into my belly.

He stayed there as I continued to chock on his cum and rooster. The other man firmly grabbed men around my waist also letting out a load groan, pulling me toward him as hard as he could."Oh my god what a fucking bewilder ass, I going to fill you up !"He shouted as I felt blastoff after shooter of hot jizz shoot deep into my ass. He pulled back out with a pop, making my ass feeling 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 other guy pulled out of my mouth. I could feel a flow of cum trickeling out of my ass. I collapsed on the desk after they let me down, exhausted, ashamed and humiliated as I lost my anal retentive virginity.

I heard the door capable again, I could hear Renee talking and I knew the other representative too. I glanced over and saw Regina talking to Renee, what the infernal region was she doing here in New House of York. Ronnie walked over to my hobble soundbox,"Reann, Ryan is a ripe psychoanalyst, but you, god can you take a dick, Regine, glad you could make it today."Regina looked shocked to see the scene in the billet."Regina, I believe you might experience this fiddling blonde bimbo lying here, this is Ryan, now Reann, he made a bet and let's say he lost more than just the wager, how do you like the transformation ?

I covered my human face so as to not see her, she walked over."Ryan is that really you ? Ryan it's me Regina, holy crap they really did wee-wee you a woman."“ Don't look at me please Regina."“ It is you I can tell, wow they did some oeuvre with you, I guess you really have changed. I am sorry honey 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 quick and Regina was stripping down.

"Reann, to really go bad you in I needed inviolable mortification, you didn't seem to make a high school sweet heart and Regina appeared to be the tight thing, everyone has a damage, and we found hers to get laid an old friend with a strapon dildo. With that he slapped my ass and told the two sustainment guy 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 woman now, your not the guy I used to fuck, now stop being a little sissy about this and hold this prick !"She said as she pressed the dildo straits 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 promiscuous cakehole she said,"Reann, recall when you wanted to try anal, well I'm about to split up you in half my piffling sissy."With that she pushed her weight as the dildo sank in slowly.
Renee spoke up,"Reann incase your wondering this is a 10 column inch dildo that is made for prostate massages with a curved tip, it is about 2 inch in diameter rightfield around the middle, or simply put, we don't expect you to come in tomorrow after Regina splits you ass in one-half, and you're about at the wooden-headed part."right wing as she said that Regina withdrew the cold dildo and shoved it back in as I let out a yelp, she just kept bucking into my ass. Pounding away, verbally abusing me about what a pansy I am."Ronnie, look what you did, his little epicene button is dripping precum diffuse and flopping around while his huge teat just spring around. You do great work I must say !"

I looked down liquid state was flowing out of my prick as it danced around, I felt a wave of pleasure building up in my ass. I started to moan, what was happening to me. My groan and panting grew louder as her dildo bucked against my hips, she was fucking me like a angry cleaning woman while Ronnie and Renee cheered on. I could only look up at the faces as they stared in a trance at the huge dildo ripping my ass up."Oh gawd, oh gawd,"I yelped out as I felt like I was about to burst 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 slight sissified fornicatress he is, only cumming from now on with a nice house cock up his ass !"Renee exclaimed. Regina kept fucking me for a few more minutes as I bucked around in pure rapture. It was too much I collapsed as she kept fucking me. I finally came too as they were all dressed and I was still naked on the lounge now.

"Reann, I am sorry I guess you must have just passed out and in the heat of the moment we didn't card. 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 all 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 deal. She felt bad but a bets a bet and she missed the old me. She did want to jazz me again, she said it gave her a lot of power, she also wanted to see a guy rail me out, perhaps my roommate, guess I know what I am doing tonight at my flat.

The end for now !