I came from a Youngstown OH, my kin 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 safe at math and managed to get a scholarship to Ohio United States Department of State I found a way out. I got a degree in maths with a focus in statistics. I applied to jobs all over the country and got a few good interview lined up in NYC. With the piffling money I had from my late dark working at a bar I flew out to NYC and interviewed with some minuscule hedge pecuniary resource. I left behind Regina, we hooked up and had a lot of great sex but never could really get down dating with college and everything.

I was uneasy but sure-footed at the same time about this movement. I had a few bout of interviews with HPQ adviser and finally I got the job as an psychoanalyst. Starting remuneration was $ 65,000 with carrying into action based bonus. My first-class honours degree week Reginold, went by Reggie told me the bonuses aren't the only if way of getting extra income, Ronnie the owner likes making small bets here or there with staff.
NYC was majuscule 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 bookman loans of $ 800 per month. farseeing hr, eating out and socializing left me no elbow room 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 shift 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 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 twist since it was all about how to easily pick out advantage of the poor in the country etc."So, you like healthcare right now, which stock in particular boy ?"“ Well 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 correctly boy, how about we bet $ 20,000 on that he said ?"I choked on my drink and everyone fit out laughing at the table myself included.

"Boy let me reword that, if it hits 300 per contribution you get $ 20K, if it hits 100 per ploughshare you stop dressing as a man and start dressing like a char in the office."He had a sinister look on his human face, the former two valet were quiet and looked intimated. I reached out and agitate on it. It was worth the risk of exposure for me plus it was trading above 200 it would need a 50 % plus root for back to hit his telephone number. Come by my office when we get back and we will work out the specifics.
I had a little bit of a bad spirit but still confident I could get that $ 20k to pay off my scholarly person loans as I walked into his office. I sat down in front of his desk,"My boy, we need to work out these details, let me ask, I looked over your resume, where you are from etc, how much do you owe in student loan and how about that as the wager ?"“ I owe $ 80,000, you'd be will to bet that much on one gillyflower ?"“ Absolutely boy, how lots do you require on top of that,"“ How about $ 100,000 plus the $ 80,000 if you want me to walk around like a adult female ?"“ Sounds like a plan, let's do this, $ 500,000, if you win you get $ 500K, if you lose, you become my slave for intimate favors with me and my friends, you will look like a charwoman, constitute up, petty surgery here or there, business office fornicatress character look, we lost Scots heather lastly month and she was the part 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 avail your family back abode and what are the chances the gillyflower drops to 100, in fact make it 90 and you have to hit 275 ? Think about how easily you can make your aliveness great ! Deal or no deal no thinking this one over end of story."I took a deep breath,"hatful !"we shook hired man, his right-hand man Robert spoke up,"ok boys, we have a bet here for a gravid sum of money, I will draft up the sound paperwork and have you both mark tomorrow reasonable enough ?"We both nodded.

My sum was racing as I walked back to my desk, Reggie asked me what was awry as I looked flushed. I explained to him the bet. He explained to me, that Ronnie loved to make those bets, he had won a similar bet and stool $ 100K on the deal. 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 small but there was all this newsworthiness about scandal going on etc. Next thing I know my heart sank and my balls pulled up, 110, 100, then it happened it closed at 75. Henry Martyn Robert approached me, Ronnie would like to see you in his office.

I took my walk of shame, waiting inside Ronnies role were a few fair sex with article of 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, right way to determine 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 char'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 trunk frame."stone's throw in the rain shower, and knock off your all your whisker but your top dog, make trusted you get your cocksucker too,"They handed me shaving cream, body wash drawing and shampoo. I took the shower and shaved everything and just stood there, my god what have I done. The woman asked me to open my cheeks, I did exposing my rosebud,"shuffle 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 robe on and they gave me a lacey lash and bra. We went back up to the office I went in through the spine into Ronnie's office."Ahh there is my winning, let's get you into a nice capture function attire."He made me pattern different clothes off the wrack settling on 1.5 in heels, a black dress with a tight white button down. He had the women leave the office and he sat on the couch."Time to go paying up boy, hope you like tool because you're going to have a lot of dick in your animation going forward. I will make for certain you are well taken attention of, just get ready 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 pants and pulled out his member. I protested as I cried,"Ryan, no one likes a shock job where the woman is crying before they even gag. Now you made this bet and could make become rich, it was worth the bet for you and this is deserving it for me. Now if you don't check up your end, go back home and start working at the supermarket where your mom is because kiss any former career dear bye. I can easily end you and your family from any normal macrocosm. Now open up and clear you tears !"

I wiped away my bout and approached his crotch, I looked down at his flaccid member maybe about 5 inch slightly thick."That a girl, he said, now suck this like the loose woman you are."As he said this he grabbed the backbone of my oral sex and lined it up with his dick."Relax young woman, slack your breathing, my shaft will grow inside your backtalk but I will slowly bob your foreland up and down nicely."I pushed my tongue forward toward the tip and licked it. To my surprisal, it didn't taste perception bad, it was rather salty. I did my best impression on what I say from the porno I've watched and took the read/write head in fully. He moaned in toleration and I just bobbed up and down slowly working in as many inches as I could.

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

I just wanted this to end, I bobbed furiously, my deal caressed his musket ball, loud slurping sounds came out of my mouth. He put his hand behind my head and I felt him fight down harder, his dick must throw been about 6 - 6.5 inches now and maybe 1.5 inches astray. I might have been down 4 inch when I felt his tip slam against the vertebral column of my throat causing me to gag. He had shoved my head down and with both hands behind my pass held me soaked. I continued to choke, tear streamed down and saliva flowed from his mouth. He buried my case into his pubes and discharge quickly allowing me an opportunity to breath as I gasped for air. While trying to catch my breath he just kept pushing down my mind as I dodged his cock, rubbed my tongue all over my face.
"Isn't life good story, one day you're some popular college kid banging miss the next you've got your head buried in some older man's crotch while you choke on his cock and the day after that two gallant are using you like a Chinese fingerbreadth lying in wait ! Now take that rooster again and sallow my cum before I shove it in your ass !"With that I realigned my mouthpiece over his cock and his thrusted it into my mouth. Gagging dissonance followed as I fought to outlast this violation on my back talk. He furiously fucked my face for about 5 moment before burying my face back down and pumping stacks 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 understructure.

I looked in the mirror, I looked like a mess. He threw a towel to me and called for Renee to come in."Oh poor child, well workplace on that gag reflex so you look like less of a tart when you're done. Here is your suitcase with you outfit for tomorrow. Please see Dr. Regario next calendar month on the 15th at 10 am. Here is his card. He has a little work to do on your nada John Major just a few detail of workplace. In the meantime, you are to take these pills, they will take a crap anal and other bodily process hurt less. Lastly here is a bag with sex toy's hindquarters sparking plug from 2 in to 6 inches that will stretch your ass for anal sex, please body of work up to these"Ronnie stood up,"Now head home kid, it's getting late, get a ripe night's residual to let this sink in."

For the side by side month, I came into work dressed as a womanhood, Reggie just nodded with a darn happens around here kind of look. No one seemed shocked at all. Reggie mentioned that Saame shit happened to heather before she left. My roommate didn't say much, a bit confused at world-class but I explained the deal and he said he would feature taken the pot too. I was really moody and upset, 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 physician's engagement was for tomorrow.

The next dawning I took my sentence getting up, showered, got fix and put on my blond wig for the day. I arrived at Dr. Regarios government agency at 10 am and filled out a crew of paperwork and consent forms. I was called into his authority. He reassured me everything is two-sided, per Ronnie's fiat there was a little workplace he wanted but naught 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 painful quantity 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 fount suffering, my thorax scathe, my ass hurt. As I looked down there was something on my chest blocking some of my thought."Ohhh my god, what the fuck did you do !"I yelled out. They gave me breast implants ! What the fuck !"I'm going to fucking kill you !"I screamed out, quickly protection came into the room and held me down. Dr. Regario walked forward."Ryan, listen here, I have orders paid for from Ronnie your honcho, along with several documents signed by you as section of a bet you two made, he does this shop all the time. He ordered, border implants, lip injectant, eyebrow lifts, hair implants, lazer hairsbreadth remotion, ass bleaching and cleansing, calf implants, breast implants, emasculation and liposuction, near of the fat from your mid-section and blazon in now in your ass. I do have 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 hormones you were taking really helped in making your tit double 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."Dr. 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 parole is, was, not, am, you were a man, after we cut off your ball you just ingest what Ronnie claim's, a sissy clit left that can't produce spermatozoan. And all these papers here protect me, you should read more carefully when betting with Ronnie."

Oh, my god, they cut off my clump, I couldn't appendage this rightfield now, strangely it didn't trauma. My will for getting upset was gone, I had no look.
Renee was waiting in the pressure group 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 physical structure looks."I said nothing just sat there crying."Ryan or Reann, take the following month off for convalescence, Ronnie has deposited $ 50,000 into your explanation to console you. Take it tardily, we will send food over and everything to ease your recuperation. These DVD's are for you to watch and educate that ass by the way."My roommate was shocked, and just didn't say a parole as I walked in with bandages and the obvious transformation.
About a month later I got ready for study, I really did look hot, huge tits, fat ass, big rim, small waist everything. My cock used to be around 6 column inch now barely 5 and skinny when hard. The DVD was fully of sissy sex and hypno, I used my dildos and fundament plugs. For some reason the dildos really made me cum and regular porn did nix, probably the pills.

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 office."My god you look beautiful ! Let's mental testing those lip out."He said as he undid his knickers. I walked over and got on my knees, I took his cock in my sass and bobbed up and down slurping this time taking it all no problem."Someone has been practicing I see. God those lip make it so much better"because of those lips drool was sliding out around his prick and running down my face.
right wing after that I heard the door open and the cleaning gang came in, I immediately stopped and pulled off mortified. Ronnie grabbed my header,"Don't stop honey ! Hey you two stay a while, isn't she pretty, this is Reann, remember the Loretta 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 pip a encumbrance deep down my pharynx. I whipped my case for cum and spit.

The two Spanish men just laughed. Ronnie told them,"Hey no one has ever broken him in, I am his first pecker, how about you two help oneself me break him in. His ass has to be tight as hell, consider it an other Christmas present."I could get wind them walking over as Ronnie let up on my head.

The two men smiled, with a Spanish speech pattern they said,"sanctum shit Ronnie, this was that young new guy, my god you gave him the raging set of tits an ass I've ever seen on a wench, let alone a swell. I'm not gay, but fuck that ass looks juicy as underworld and those lip 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 tall maybe 6'3"the former one shortsighted and fat maybe 5'6"both Spanish and kind of grimy looking. They both started unzipping their knickers when two fat cocks plopped out. My backtalk dropped and I looked at Ronnie,"But they are too big ?"“ Not for my fiddling slut, up on the desk you go, and pop 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 mamilla !"They pushed me and flex me over the desk. The improbable one walked in battlefront of me and started jerking his dick, it was getting harder maybe, 8 or 9 in and really fat. He pushed it into my mouth, 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 flavor at this lump of meat Reann ! And suck that big fat stopcock !"

As I looked up I thought to myself how is it the forgetful guy has the biggest peter. It was severely maybe 10 inch and as midst as my articulatio radiocarpea. Ronnie made me alternate 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 pleasure while trying to come through the dick in my rima oris. The dick 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 lip as I gasped for air. It pushed against a lot of resistance on my ass but popped past my anal ring letting the straits in. I screamed in painfulness again silenced into the former man's crotch as I tried to worm. A Wave of chagrin, pain in the ass and pleasure swept across me. He just kept pushing, additional tears flowed down my buttock."Roque, this ass is so tight, it's like Heaven man you got to try it soon ! Now I am going to wreck this livid piece of ass thought fucking clean and jerk this up Andrew D. White boy !"He shouted thrusting about 5 inches in as I jolted forward on the desk, kicking my legs up in the air.

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

"Wow this is quite a mountain, your cocks are impaling this piddling girlfriend 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 give up and push a little but they clamped my legs down under the man's armpits and locked me in place, the short 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 expression at his picayune cock bob around, after all those hormones and removing those chunk its LE 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 tongue ran down my face the man in my mouth let out a loud moan holding his hammer buried down my throat releasing stream after current of hot special K 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 load groan, pulling me toward him as hard as he could."Oh my god what a fucking amazing ass, I going to take you up !"He shouted as I felt snapshot after shot of hot jizz shoot deep into my ass. He pulled back out with a pop, making my ass tactile property empty and then slammed it right back in as I let out a yelping."Ohh god that ass was amazing."He exclaimed, the man slowly withdrew his peter from my ass as the other guy pulled out of my mouth. I could feel a stream of cum trickeling out of my ass. I collapsed on the desk after they let me down, consume, ashamed and humiliated as I lost my anal virginity.

I heard the door open again, I could hear Renee talking and I knew the other vocalism 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 body,"Reann, Ryan is a good analyst, but you, god can you film a cock, Regine, gladiolus you could take in it today."Regina looked traumatise to see the scenery in the place."Regina, I believe you might know this fiddling light-haired bimbo lying here, this is Ryan, now Reann, he made a bet and let's say he lost Sir Thomas More than just the wager, how do you like the transformation ?

I covered my 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 make you a woman."“ Don't look at me please Regina."“ It is you I can tell, wow they did some employment with you, I guess you really have changed. I am dreary 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 shoulder strap on dildo ready and Regina was stripping down.

"Reann, to really break you in I needed absolute humiliation, you didn't seem to possess a high school day sweet pith and Regina appeared to be the closest affair, everyone has a price, and we found hers to fuck an old admirer with a strapon dildo. With that he slapped my ass and told the two maintenance cat to get out.
Renee was helping Regina get on the orotund strapon. I pleaded and cried,"Regina please don't do this I can't vigil you fuck me like this you can't !"She approached lathering the dildo in lube, Renee and Ronnie lifted my ramification up in the air exposing my cum dripping ass."Reann, you're a woman now, your not the guy I used to make love, now stop being a short sissy about this and take this cock !"She said as she pressed the dildo forefront against my ass. This was beyond humiliating, I used to bang her and always wanted to try anal but not like this. As she pressed harder breaking the roadblock of my already loose hole she said,"Reann, retrieve when you wanted to try anal, well I'm about to split you in half my short 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 inches in diameter right around the heart, or simply put, we don't expect you to come in tomorrow after Regina splits you ass in half, and you're about at the thickest 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, attend what you did, his minuscule sissy button is dripping precum soft and flopping around while his Brobdingnagian mamilla just bounce around. You do neat work I must say !"

I looked down liquid state was flowing out of my stopcock as it danced around, I felt a wafture of pleasure 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 crazy woman while Ronnie and Renee cheered on. I could only look up at the faces as they stared in a enchantment 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 cock started to let out a current of cum like a faucet, it pooled all over my stomach.

"There is goes, he fucking came like the minuscule effeminate 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 minutes as I bucked around in pure ecstasy. 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 couch now.

"Reann, I am drear I guess you must let 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, postulate the day off tomorrow, you've done enough work today."

Regina and I went out to dinner, I was ashamed and told her the unanimous account. She explained how they called her out of the blue and offer $ 100,000 to have intercourse you and an supererogatory $ 50,000 if I really humiliated you. I didn't inculpation her for taking the deal. She felt bad but a stakes a bet and she missed the old me. She did want to be intimate me again, she said it gave her a lot of powerfulness, she also wanted to see a guy rail in me out, perhaps my roomie, guess I know what I am doing tonight at my apartment.

The end for now !