I came from a Youngstown OH, my family was really poor growing up and animation wasn't easy. My sire 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 Nox. Since I was really good at math and managed to get a learnedness to Ohio State I found a way out. I got a academic degree in math with a nidus in statistic. I applied to jobs all over the country and got a few skillful consultation lined up in NYC. With the picayune money I had from my latterly night working at a bar I flew out to NYC and interviewed with some small hedging investment trust. 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 flighty but confident at the same time about this move. I had a few rounds of interviews with HPQ advisor and finally I got the job as an psychoanalyst. Starting salary was $ 65,000 with carrying into action based fillip. My kickoff week Reginold, went by Reggie told me the bonuses aren't the only way of getting extra income, Ronnie the owner likes making piffling stakes here or there with staff.
NYC was keen minus one thing, the cost, I had found a two-bedroom apt that one bed elbow room was for split but it was $ 1,300 per month and I had student loans of $ 800 per month. Long hour, eating out and socializing left me no room to spare from my cash flow.

I was in the toilet one day and noticed Ronnie was in there washing his hands 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 recent teddy 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 early business companion talk about various topics, nearly of which made my abdomen turn since it was all about how to easily accept advantage of the poor in the country etc."So, you like healthcare right now, which stock certificate 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 momentum it could easily go to 300."“ Is that right on boy, how about we bet $ 20,000 on that he said ?"I choked on my swallow and everyone explosion out laughing at the board myself included.

"Boy let me rephrase that, if it hits 300 per share you get $ 20K, if it hits 100 per percentage you stop dressing as a man and originate dressing like a woman in the office."He had a sinister face on his face, the other two gentlemen were tranquillity and looked intimated. I reached out and shook on it. It was worth the risk for me plus it was trading above 200 it would need a 50 % plus extract back to hit his number. Come by my part when we get back and we will work out the specifics.
I had a little bit of a bad feeling but still sure-footed I could get that $ 20k to pay off my student 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 lots do you owe in scholar loanword and how about that as the bet ?"“ I owe $ 80,000, you'd be willing to bet that much on one gillyflower ?"“ Absolutely boy, how much do you require on top of that,"“ How about $ 100,000 plus the $ 80,000 if you want me to take the air around like a woman ?"“ Sounds like a design, let's do this, $ 500,000, if you win you get $ 500K, if you lose, you become my striver for sexual party favour with me and my friends, you will calculate like a charwoman, make up, little surgery here or there, office slut type face, we lost Heather endure month and she was the power 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 slip, you would be able to help your family back home and what are the hazard the stock certificate drops to 100, in fact make it 90 and you have to hit 275 ? Think about how easily you can make your life great ! mountain or no deal no thinking this one over end of story."I took a abstruse breath,"Deal !"we shook hands, his right-hand man Henry M. Robert spoke up,"ok boys, we have a bet here for a large sum of money, I will draft up the legal paperwork and have you both sign tomorrow fair enough ?"We both nodded.

My mettle was racing as I walked back to my desk, Reggie asked me what was legal injury as I looked flushed. I explained to him the wager. He explained to me, that Ronnie loved to stool those bets, he had won a similar bet and make $ 100K on the mickle. I felt much better, I closely tracked the line of descent for the few month it hit 257 before quickly plummeting to 175, I thought I was going to cry, when it rallied back a slight but there was all this newsworthiness about malicious gossip going on etc. Next matter I know my heart sank and my lump pulled up, 110, 100, then it happened it closed at 75. Henry Martyn Robert approached me, Ronnie would care to see you in his office.

I took my walk of ignominy, waiting inside Ronnies office were a few cleaning woman with 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, best way to learn is to get you balls kicked in. In your font, literally, now Renee make him look pretty,"she looked at me,"seed with us to the cleaning lady's cabinet room in the gym downstairs."My heart was racing, these three beautiful woman walked me to the women's footlocker."slip down, let's see what we are working with."I turned beat red, I am 5'9"and weight 150 lbs with a lanky consistency frame."Step in the shower, and trim your all your haircloth but your head, make sure you get your asshole too,"They handed me shaving cream, trunk wash and shampoo. I took the shower bath and shaved everything and just stood there, my god what have I done. The adult female asked me to propagate my cheeks, I did exposing my rosebud,"make for certain 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 thong and bra. We went back up to the office staff I went in through the back into Ronnie's role."Ahh there is my win, let's get you into a nice appropriate office attire."He made me mock up different clothes off the rack settling on 1.5 column inch heels, a dim frock with a tight white button down. He had the women leave the spot and he sat on the couch."prison term to start paying up boy, hope you like cock because you're going to have a lot of peter in your living going forward. I will name for certain you are well taken aid of, just get set to chug a lot of shaft"

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 phallus. I protested as I cried,"Ryan, no one likes a blow job where the cleaning woman is crying before they even gag. Now you made this bet and could have become racy, it was deserving the bet for you and this is worth it for me. Now if you don't hold up your end, go back dwelling house and initiate working at the supermarket where your mom is because osculate any other career good bye. I can easily end you and your family from any normal universe. Now open up and enlighten you tears !"

I wiped away my rent and approached his privates, I looked down at his flabby member maybe about 5 inches slightly thick."That a missy, he said, now suck this like the slut you are."As he said this he grabbed the cover of my headspring and lined it up with his dick."Relax girl, slow up your respiration, my cock will grow inside your oral cavity but I will slowly bob your psyche up and down nicely."I pushed my lingua forward toward the tip and licked it. To my surprise, it didn't taste bad, it was rather salty. I did my well impression on what I say from the pornos I've watched and took the head in fully. He moaned in acceptance and I just bobbed up and down slowly working in as many inches as I could.

"flavour 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 sound job."I stared up at him, tear still building, bobbing up and down as I felt his cock slowly growing inside my backtalk.

I just wanted this to end, I bobbed furiously, my hands caressed his nut, loud slurping sounds came out of my mouth. He put his hand behind my head and I felt him push down harder, his dick must make been about 6 - 6.5 inch now and maybe 1.5 inches wide. I might cause been down 4 column inch when I felt his tip jibe against the back of my throat causing me to gag. He had shoved my caput down and with both hands behind my pass held me loaded. I continued to choke, crying streamed down and spittle flowed from his mouth. He buried my grimace into his pubes and press release quickly allowing me an opportunity to breath as I gasped for air. While trying to enamour my breath he just kept pushing down my promontory as I dodged his cock, rubbed my spit all over my expression.
"Isn't life sentence funny, one day you're some popular college kid banging girls the next you've got your school principal buried in some older man's fork while you choke on his cock and the day after that two dude are using you like a Taiwanese fingerbreadth 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 rooster and his thrusted it into my back talk. Gagging randomness followed as I fought to survive this assault on my mouth. He furiously fucked my side for about 5 minutes before burying my aspect back down and pumping oodles of salty slimy cum into my belly. As he let go I choked and gasped for air. He pulled his trouser up and sat back at his desk as I struggled to get to my foundation.

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 baby, well employment on that gag reflex so you look like less of a whore when you're done. Here is your grip with you outfit for tomorrow. Please see Dr. Regario next month on the 15th at 10 am. Here is his board. He has a little work to do on your zip major just a few items of piece of work. In the meantime, you are to charter these anovulant, they will make anal and other natural process hurt less. Lastly here is a bag with sex toy's butt plugs from 2 inches to 6 column inch that will dilute your ass for anal sex, please study up to these"Ronnie stood up,"Now head base kid, it's getting late, get a good night's rest to let this settle in."

For the next month, I came into work dressed as a cleaning lady, Reggie just nodded with a dickhead happens around here kind of facial expression. No one seemed shocked at all. Reggie mentioned that same shit happened to heather before she left. My roomy didn't say much, a bit confused at first but I explained the deal and he said he would have taken the stack too. I was really moody and disconcert, 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 fitting was for tomorrow.

The adjacent morning I took my time getting up, showered, got prepare 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 oeuvre he wanted but cipher 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 abominable total of painful sensation, dazed and confused as to what just happened."Ah our affected role is finally coming too."Dr. Regario exclaimed. I slowly tried to sit up, my cheek hurt, my chest suffering, my ass scathe. 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 fuck !"I'm going to fucking belt down you !"I screamed out, quickly security came into the way and held me down. Dr. Regario walked forward."Ryan, listen here, I have orders paid for from Ronnie your party boss, along with various documents signed by you as part of a bet you two made, he does this shit all the clip. He ordered, cigaret implants, lip injectant, eyebrow lifts, hair implants, lazer hair's-breadth removal, ass bleaching and cleansing, calf implants, breast implants, castration and suction lipectomy, almost of the fat from your mid-section and arms in now in your ass. I do have to say you came out pretty goddamn hot though !"

My nub sank and I passed out. I awoke again."That happened a lot around here, perfectly convention. Those hormones you were taking really helped in making your tits stunt man ds by the way, they gave us just enough tissue around the edges."I thought I was dreaming earlier until he made that remark. 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 intelligence is, was, not, am, you were a man, after we cut off your balls you just induce what Ronnie cry's, a sissy clit left that can't green groceries sperm. And all these papers here protect me, you should register 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 tone.
Renee was waiting in the lobby for me as she helped me garner my belongings and escorted me to her car. She drove me dwelling house,"So is some commove to see how their beautiful new body looks."I said nil just sat there crying."Ryan or Reann, take the next calendar month off for convalescence, Ronnie has deposited $ 50,000 into your account statement to soothe you. Take it easy, we will send food over and everything to ease your recovery. These DVD's are for you to watch and train that ass by the way."My roommate was shocked, and just didn't say a word as I walked in with bandage and the obvious transformation.
About a month later I got set up for work, I really did search hot, huge tits, fat ass, big lips, small waist everything. My tool used to be around 6 inches now barely 5 and skinny when tough. The DVD was fully of sissy sex and hypno, I used my dildos and rear hype. For some understanding the dildos really made me cum and regular erotica did zilch, probably the contraceptive 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 well-chosen. Ronnie wants to see you after work."

Right as everyone was leaving for the day I walked into Ronnie's position."My god you look beautiful ! Let's mental test those lips out."He said as he undid his pant. I walked over and got on my knees, I took his prick in my mouthpiece and bobbed up and down slurping this meter taking it all no job."person has been practicing I see. God those brim make it so much better"because of those sassing drool was sliding out around his cock and running down my face.
rightfield after that I heard the door overt and the cleaning work party came in, I immediately stopped and pulled off mortified. Ronnie grabbed my promontory,"Don't stop dear ! Hey you two stay a while, isn't she pretty, this is Reann, commemorate the young guy that works here this is him after surgery."He just keep pumping and a few import later he pushed my head all the way in and fritter a load deep down my pharynx. I whipped my face 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 dick, how about you two help me break him in. His ass has to be tight as hell on earth, consider it an early Xmas present."I could hear them walking over as Ronnie let up on my head.

The two men smiled, with a Spanish dialect they said,"holy place shit Ronnie, this was that young new guy, my god you gave him the spicy set of pap an ass I've ever seen on a chick, let alone a gallant. 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 tool in your ass, Reann is the simply one in the room that will have one up her pussy !"

I looked at them one was tall maybe 6'3"the early one short and fat maybe 5'6"both Spanish and sort of grimy looking. They both started unzipping their pants when two fat cocks 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 get going sucking."I stood up and the two men pulled my skirt and panty down, I froze, they unbuttoned my top and took my bra off."Wow look at those teat !"They pushed me and turn away me over the desk. The tall one walked in front end 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 rima oris, 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 smell at this hunk of essence Reann ! And suck that big fat cock !"

As I looked up I thought to myself how is it the unretentive guy has the bountiful cock. It was hard maybe 10 inches and as midst as my articulatio radiocarpea. Ronnie made me tack 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 in the ass and delight while trying to pull round the cock in my back talk. The dick 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 cock head at my ass, I tried to resist, screaming but it was silenced into the peter in my oral fissure as I gasped for air. It pushed against a lot of resistance on my ass but popped past my anal retentive ring letting the school principal in. I screamed in pain again silenced into the other man's crotch as I tried to squirm. A undulation of abasement, painful sensation and pleasure swept across me. He just kept pushing, additional crying 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 bust up this white piece of ass thought fucking clean this up gabardine 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 inside couldn't accommodate any Thomas More when another inch when in. My insides felt like they were being ripped apart. My face plowed into the other man's peter showing no leak from the hammer. He pulled out and rammed it back in getting maybe 8 inches in, pulling out again before ramming me into the other man's cock again as his balls slapped against my fiddling cock that was just dangling there.

"Wow this is quite a slew, 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 recoil and advertize a slight but they clamped my legs down under the man's armpits and locked me in place, the short guy lined his rooster up again and thrusted in as I screamed out in pain. The other man silenced me quickly ramming his hammer down my throat again and they two fucked me furiously."My god look at his minuscule cock bob around, after all those hormones and removing those balls its less a putz 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 cheeks the man in my sass let out a trashy moan holding his cock buried down my throat releasing stream after flow of hot jet of cum into my belly.

He stayed there as I continued to chock on his cum and tool. The other man firmly grabbed men around my waist also letting out a loading groan, pulling me toward him as hard as he could."Oh my god what a fucking awful ass, I going to fill you up !"He shouted as I felt shot after blastoff 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 yelping."Ohh god that ass was amazing."He exclaimed, the man slowly withdrew his peter from my ass as the early 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, tucker out, ashamed and humiliated as I lost my anal virginity.

I heard the doorway open again, I could get a line Renee talking and I knew the other vocalism too. I glanced over and saw Regina talking to Renee, what the Scheol was she doing here in New House of York. Ronnie walked over to my limp torso,"Reann, Ryan is a dear analyst, but you, god can you make a dick, Regine, gladiolus you could construct it today."Regina looked shocked to see the scene in the office."Regina, I believe you might have a go at it this picayune light-haired bimbo lying here, this is Ryan, now Reann, he made a bet and let's say he lost more than just the stakes, how do you like the shift ?

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

"Reann, to really discover you in I needed absolute humiliation, you didn't seem to hold a in high spirits school mellisonant heart and Regina appeared to be the cheeseparing thing, everyone has a cost, 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 large strapon. I pleaded and cried,"Regina please don't do this I can't sentry you fuck me like this you can't !"She approached lathering the dildo in lubricator, Renee and Ronnie lifted my legs up in the air exposing my cum dripping ass."Reann, you're a adult female now, your not the guy I used to fuck, now stop being a short sissy about this and carry this cock !"She said as she pressed the dildo drumhead against my ass. This was beyond humiliating, I used to bed her and always wanted to try anal but not like this. As she pressed harder breaking the roadblock of my already loose jam she said,"Reann, remember when you wanted to try anal, well I'm about to dissever you in half my little sissy."With that she pushed her weight as the dildo sank in slowly.
Renee spoke up,"Reann incase your wondering this is a 10 inch dildo that is made for prostate massages with a slue tip, it is about 2 inch in diameter right around the middle, 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 fatheaded part."Right as she said that Regina withdrew the common cold 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 sissy I am."Ronnie, reckon what you did, his little sissy clit is dripping precum soft and flopping around while his huge tits just bounce around. You do great work I must say !"

I looked down liquid was flowing out of my cock as it danced around, I felt a wafture of joy building up in my ass. I started to groan, what was happening to me. My moan and panting grew louder as her dildo bucked against my hip joint, she was fucking me like a wild char while Ronnie and Renee cheered on. I could only bet up at the faces as they stared in a trance at the immense 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 spigot, it pooled all over my venter.

"There is goes, he fucking came like the niggling Milquetoast fornicatress he is, only cumming from now on with a nice firm tool 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 sorry I guess you must have just passed out and in the heat of the mo we didn't notification. 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 screw out, read the day off tomorrow, you've done enough oeuvre today."

Regina and I went out to dinner, I was ashamed and told her the whole write up. 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 rap her for taking the good deal. She felt bad but a stakes a bet and she missed the old me. She did require 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 roommate, guess I know what I am doing tonight at my flat.

The end for now !