I came from a Youngstown OH, my family was really poor growing up and biography 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 care at night. Since I was really good at math and managed to get a scholarship to Ohio state of matter I found a way out. I got a grade in math with a centering in statistics. I applied to jobs all over the commonwealth and got a few good consultation lined up in NYC. With the little money I had from my late nighttime working at a bar I flew out to NYC and interviewed with some little hedge monetary fund. I left behind Regina, we hooked up and had a lot of great sex but never could really start dating with college and everything.

I was nervous but confident at the same metre about this motion. I had a few beat of interviews with HPQ Advisors and finally I got the job as an analyst. Starting salary was $ 65,000 with performance based fillip. My first workweek Reginold, went by Reggie told me the bonuses aren't the only way of getting supernumerary income, Ronnie the proprietor likes making picayune bets here or there with staff.
NYC was great minus one thing, the cost, I had found a two-bedroom apt that one bed room was for rent but it was $ 1,300 per month and I had educatee loanword of $ 800 per month. Long hours, eating out and socializing left me no room to save from my cash flow.

I was in the bathroom one day and noticed Ronnie was in there washing his hired hand as I was."Hey kid you new here ?"he asked. I nodded,"my epithet is Ryan ”."Ah, yes Ryan you were the one that suggested the late transmutation to healthcare sector, which has worked out quite nicely."“ Yes, sir that was me."“ fountainhead why don't you meet me for lunch 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 early business associates talk about versatile topics, almost of which made my breadbasket turn since it was all about how to easily rent advantage of the pathetic in the country etc."So, you like healthcare right now, which caudex in particular boy ?"“ wellspring sir Valeantz looks like a decent buy right now it is trading at 228 but my figuring show based on its momentum it could easily go to 300."“ Is that right 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 rephrase that, if it hits 300 per share you get $ 20K, if it hits 100 per share you stop dressing as a man and start dressing like a cleaning lady in the office."He had a sinister look on his case, the other two gentleman were placidity 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 pull back to hit his telephone number. Come by my office when we get back and we will shape out the specific.
I had a little bit of a bad touch but still surefooted I could get that $ 20k to pay off my student loanword as I walked into his office. I sat down in front of his desk,"My boy, we need to work out these detail, let me ask, I looked over your survey, where you are from etc, how much do you owe in student loans and how about that as the stakes ?"“ I owe $ 80,000, you'd be uncoerced to bet that much on one stock ?"“ Absolutely boy, how a lot do you desire on top of that,"“ How about $ 100,000 plus the $ 80,000 if you want me to walk around like a woman ?"“ phone like a plan, 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 ally, you will look like a charwoman, take a leak up, little surgery here or there, authority adulteress type flavor, we lost broom last calendar month and she was the office fuck 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 case, you would be able to help your family back household and what are the hazard the stock drib to 100, in fact make it 90 and you have to hit 275 ? believe about how easily you can take a crap your animation gravid ! quite a little or no bargain no thinking this one over end of story."I took a mystifying breath,"Deal !"we shook custody, his right-hand man Robert spoke up,"ok boys, we have a bet here for a turgid sum of money, I will draft up the sound paperwork and have you both sign tomorrow fair enough ?"We both nodded.

My heart was racing as I walked back to my desk, Reggie asked me what was unseasonable as I looked flushed. I explained to him the wager. He explained to me, that Ronnie loved to make those bets, he had won a similar bet and have $ 100K on the mass. I felt much intimately, I closely tracked the inventory for the few calendar month 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 news about scandal going on etc. Next matter I know my heart sank and my balls pulled up, 110, 100, then it happened it closed at 75. Robert approached me, Ronnie would care to see you in his role.

I took my walk of ignominy, waiting inside Ronnies office were a few women with clothing wrack 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, outflank way to learn is to get you balls kicked in. In your casing, literally, now Renee make him look pretty,"she looked at me,"seed with us to the women's footlocker room in the gym downstairs."My heart was racing, these three beautiful charwoman walked me to the cleaning lady's locker."landing strip down, let's see what we are working with."I turned cadence red, I am 5'9"and weight 150 lbs with a lanky body frame of reference."Step in the cascade, and knock off your all your hair but your brain, make sure you get your asshole too,"They handed me shaving pick, consistency washables and shampoo. I took the shower and shaved everything and just stood there, my god what have I done. The woman asked me to fan out my cheeks, I did exposing my rosebud,"Make sure no hair 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 makeup and put a wig on. I had a gown on and they gave me a lacey G-string and bra. We went back up to the office I went in through the back into Ronnie's office."Ahh there is my win, let's get you into a nice reserve office attire."He made me model different apparel off the rack settling on 1.5 inch blackguard, a black dress with a closely whitened release down. He had the women leave the office and he sat on the couch."Time to get down paying up boy, hope you like cock because you're going to have a lot of peter in your life going forward. I will pee sure as shooting you are well taken tending of, just get gear up to chug a lot of cock"

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 trouser and pulled out his extremity. 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 have become rich, it was worth the bet for you and this is worth it for me. Now if you don't obligate up your end, go back home and start working at the supermarket where your mom is because kiss any other career good bye. I can easily end you and your kinfolk from any normal existence. Now open up and clear you tears !"

I wiped away my tears and approached his fork, I looked down at his flaccid member maybe about 5 in slightly thick."That a girlfriend, he said, now suck this like the slut you are."As he said this he grabbed the back of my school principal and lined it up with his cock."Relax young woman, slow your ventilation, my turncock will grow inside your mouth but I will slowly bob your headland up and down nicely."I pushed my natural language forward toward the tip and licked it. To my surprise, it didn't taste bad, it was rather salty. I did my best impression on what I say from the pornos I've watched and took the head in fully. He moaned in sufferance and I just bobbed up and down slowly working in as many inches as I could.

"Look up at me, I have to see you with my stopcock buried in your passably picayune mouth, you realize there is no way out but to do a undecomposed job."I stared up at him, rent still building, bobbing up and down as I felt his tool slowly growing inside my mouth.

I just wanted this to end, I bobbed furiously, my hands caressed his balls, meretricious slurping sounds came out of my mouth. He put his hand behind my read/write head and I felt him push down harder, his shaft must have been about 6 - 6.5 inch now and maybe 1.5 inches wide. I might have been down 4 inches when I felt his tip shaft against the back of my pharynx causing me to gag. He had shoved my head down and with both hands behind my head held me fast. I continued to choke, bout streamed down and saliva flowed from his mouth. He buried my face into his pubic bone and passing quickly allowing me an opportunity to breath as I gasped for air. While trying to catch up with my breathing spell he just kept pushing down my oral sex as I dodged his cock, rubbed my spit all over my typeface.
"Isn't life story funny, one day you're some popular college kid banging girls the next you've got your head buried in some onetime man's genitals while you choke on his cock and the day after that two fellow are using you like a Chinese finger trap ! Now take that cock again and sallow my cum before I shove it in your ass !"With that I realigned my oral cavity over his tool and his thrusted it into my mouthpiece. Gagging stochasticity followed as I fought to survive this rape on my mouth. He furiously fucked my face 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 foot.

I looked in the mirror, I looked like a mess. He threw a towel to me and called for Renee to fall in."Oh poor baby, well work on that gag reflex so you look like to a lesser extent of a whore 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 notice. He has a niggling oeuvre to do on your zippo major just a few detail of oeuvre. In the lag, you are to take these pills, they will make anal and other activities hurt less. Lastly here is a bag with sex toy's butt fire hydrant from 2 inches to 6 inches that will stretch your ass for anal retentive sex, please study up to these"Ronnie stood up,"Now head home kid, it's getting late, get a thoroughly nighttime's rest to let this patch up in."

For the future month, I came into work dressed as a woman, Reggie just nodded with a shucks happens around here kind of look. No one seemed shocked at all. Reggie mentioned that same shit happened to heather before she left. My roomie didn't say much, a bit upset at kickoff but I explained the deal and he said he would give taken the deal too. I was really moody and derangement, but Ronnie didn't do anything else that was sexual. I gained a bunch of weight probably from eating and being depressed. I noticed on my calendar the Doctor's date was for tomorrow.

The succeeding morning I took my clock time 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 bunch of paperwork and consent forms. I was called into his office. He reassured me everything is two-sided, per Ronnie's order there was a little work he wanted but nothing John Roy Major. I didn't even want to know 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 amount of money of pain, dazed and confused as to what just happened."Ah our patient is finally coming too."Dr. Regario exclaimed. I slowly tried to sit up, my face hurt, my thorax suffering, my ass hurt. As I looked down there was something on my chest blocking some of my view."Ohhh my god, what the roll in the hay did you do !"I yelled out. They gave me knocker implants ! What the screw !"I'm going to fucking pop you !"I screamed out, quickly surety came into the room and held me down. Dr. Regario walked forward."Ryan, listen here, I have order paid for from Ronnie your boss, along with several papers signed by you as part of a bet you two made, he does this shit all the sentence. He ordered, butt implants, lip injection, eyebrow lifts, haircloth implants, lazer hair removal, ass bleaching and cleansing, calf implants, breast implants, expurgation and suction lipectomy, most of the fat from your mid-section and weapon in now in your ass. I do accept 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 formula. Those hormones you were taking really helped in making your tits double ds by the way, they gave us just enough tissue 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 password is, was, not, am, you were a man, after we cut off your balls you just have what Ronnie call's, a sissy clit left that can't green groceries spermatozoan. And all these document here protect me, you should learn more carefully when betting with Ronnie."

Oh, my god, they cut off my nut, I couldn't process this right field now, strangely it didn't injury. My will for getting turnover was gone, I had no belief.
Renee was waiting in the pressure group for me as she helped me gather my property and escorted me to her car. She drove me home,"So is some charge up to see how their beautiful new body looks."I said nothing just sat there crying."Ryan or Reann, take the next month off for convalescence, Ronnie has deposited $ 50,000 into your account statement to soothe you. take away it easy, we will station food over and everything to ease your recovery. These DVD's are for you to watch over and civilize that ass by the way."My roomie was shocked, and just didn't say a watchword as I walked in with bandages and the obvious transformation.
About a month later I got ready for oeuvre, I really did look hot, huge tits, fat ass, big lips, small waist everything. My shaft used to be around 6 in now barely 5 and skinny when hard. The DVD was fully of sissy sex and hypno, I used my dildos and arse plugs. For some reason the dildos really made me cum and regular porn did goose egg, probably the birth control 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 as everyone was leaving for the day I walked into Ronnie's billet."My god you look beautiful ! Let's run those lip out."He said as he undid his knickers. I walked over and got on my knees, I took his cock in my mouth and bobbed up and down slurping this clip taking it all no job."mortal has been practicing I see. God those backtalk make it so much better"because of those lips drool was sliding out around his cock and running down my face.
right wing after that I heard the doorway unresolved and the cleanup work party came in, I immediately stopped and pulled off mortified. Ronnie grabbed my head,"Don't stop beloved ! Hey you two stay a piece, isn't she pretty, this is Reann, think of the youth guy that works here this is him after surgery."He just keep pumping and a few moment later he pushed my head all the way in and fool a consignment deep down my pharynx. I whipped my cheek for cum and spittle.

The two Spanish men just laughed. Ronnie told them,"Hey no one has ever broken him in, I am his first cock, how about you two avail me bankrupt him in. His ass has to be tight as hell, consider it an early Yule present."I could pick up them walking over as Ronnie let up on my top dog.

The two men smiled, with a Spanish speech pattern they said,"Holy shit Ronnie, this was that offspring new guy, my god you gave him the hot set of titmouse an ass I've ever seen on a bird, let alone a fop. 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 shaft in your ass, Reann is the just one in the room that will have one up her cunt !"

I looked at them one was tall maybe 6'3"the early one unretentive and fat maybe 5'6"both Spanish and variety of grimy looking. They both started unzipping their pants when two fat putz plopped out. My mouth dropped and I looked at Ronnie,"But they are too big ?"“ Not for my little slut, 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 look at those tits !"They pushed me and crouch me over the desk. The tall one walked in front of me and started jerking his dick, it was getting harder maybe, 8 or 9 column inch and really fat. He pushed it into my back talk, 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 lump of meat Reann ! And suck that big fat cock !"

As I looked up I thought to myself how is it the short-circuit guy has the expectant cock. It was hard maybe 10 inch and as midst as my articulatio radiocarpea. Ronnie made me flip-flop between the two sucking them furiously, chocking, gagging, spitting. The short one walked back around as Ronnie was lubing up my ass. I didn't notice much, moaning from pain and pleasance while trying to survive the cock in my mouth. The gumshoe in was meeting 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 shaft school principal at my ass, I tried to protest, screaming but it was silenced into the peter in my mouth as I gasped for air. It pushed against a lot of impedance on my ass but popped past my anal ring letting the head in. I screamed in pain again silenced into the other man's fork as I tried to wrestle. A moving ridge of humiliation, pain and joy swept across me. He just kept pushing, additional rip flowed down my brass."Roque, this ass is so tight, it's like heaven man you got to try it soon ! Now I am going to wreck this Caucasian spell of ass thought fucking clean this up white 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 Sir Thomas More when another in when in. My insides felt like they were being ripped apart. My face plowed into the early man's cock showing no leak from the shaft. He pulled out and rammed it back in getting maybe 8 inch in, pulling out again before ramming me into the other man's shaft again as his balls slapped against my slight hammer that was just dangling there.

"Wow this is quite a sight, your cocks are impaling this little girl on both ends 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 kick and push a fiddling but they clamped my legs down under the man's armpits and locked me in home, the abruptly guy lined his cock up again and thrusted in as I screamed out in pain. The former man silenced me quickly ramming his cock down my throat again and they two fucked me furiously."My god facial expression at his small rooster bob around, after all those internal secretion and removing those orchis its less a cock and More of an itsy bitsy sissy clitsy !"All the men laughed while I was mercilessly railed out on both conclusion. Siliva and spit ran down my cheeks the man in my mouth let out a loud moan holding his pecker buried down my throat releasing flow after stream of hot jets of cum into my belly.

He stayed there as I continued to chock on his cum and cock. The other man firmly grabbed men around my waist also letting out a shipment groan, pulling me toward him as hard as he could."Oh my god what a fucking amazing ass, I going to fill you up !"He shouted as I felt shot 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 yip."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 back talk. I could feel a stream of cum trickeling out of my ass. I collapsed on the desk after they let me down, fagged, ashamed and humiliated as I lost my anal virginity.

I heard the room access assailable again, I could get word Renee talking and I knew the other voice too. I glanced over and saw Regina talking to Renee, what the hell was she doing here in New York. Ronnie walked over to my limp physical structure,"Reann, Ryan is a thoroughly analyst, but you, god can you drive a cock, Regine, glad you could make it today."Regina looked shocked to see the tantrum in the bureau."Regina, I believe you might know this petty 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 case so as to not see her, she walked over."Ryan is that really you ? Ryan it's me Regina, holy crap they really did make you a woman."“ Don't face 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 dear 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 shoulder strap on dildo ready and Regina was stripping down.

"Reann, to really break you in I needed downright chagrin, you didn't seem to have a high schooltime cherubic nub and Regina appeared to be the closest matter, everyone has a price, and we found hers to fuck an old friend with a strapon dildo. With that he slapped my ass and told the two maintenance guys to get out.
Renee was helping Regina get on the big 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 lubricant, 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 jazz, now stop being a slight sissy about this and study this cock !"She said as she pressed the dildo headland against my ass. This was beyond humiliating, I used to jazz her and always wanted to try anal retentive but not like this. As she pressed harder breaking the barrier of my already loose pickle she said,"Reann, remember when you wanted to try anal retentive, well I'm about to split you in half my picayune sissy."With that she pushed her weight as the dildo sank in slowly.
Renee spoke up,"Reann incase your wondering this is a 10 in dildo that is made for prostate massages with a curving tip, it is about 2 inches in diam rightfield around the middle, or simply put, we don't expect you to fall in tomorrow after Regina splits you ass in half, and you're about at the thickest part."right hand 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 sissy I am."Ronnie, attend what you did, his piddling sissy clit is dripping precum soft and flopping around while his huge mammilla just bounce around. You do nifty study I must say !"

I looked down liquid was flowing out of my cock as it danced around, I felt a moving ridge of delight 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 risky woman while Ronnie and Renee cheered on. I could only calculate 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 erupt when all of a sudden my tool started to let out a watercourse of cum like a faucet, it pooled all over my stomach.

"There is goes, he fucking came like the trivial milksop slut he is, only cumming from now on with a nice firm cock up his ass !"Renee exclaimed. Regina kept fucking me for a few Sir Thomas More instant as I bucked around in pure raptus. 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 sofa now.

"Reann, I am sorry I guess you must get just passed out and in the rut of the moment we didn't notice. 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 piece of 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 get laid you and an extra $ 50,000 if I really humiliated you. I didn't incrimination her for taking the tidy sum. 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 train me out, perhaps my roommate, guesswork I know what I am doing tonight at my apartment.

The end for now !