I came from a Youngstown OH, my family was really poor growing up and biography wasn't easy. My founding father moved out and left us when I was only 10 and my female parent supported the family working at a supermarket during the day and bar attention at night. Since I was really good at mathematics and managed to get a encyclopedism to Buckeye State State I found a way out. I got a degree in math with a focussing in statistic. I applied to business all over the country and got a few good interviews lined up in NYC. With the little money I had from my late night working at a bar I flew out to NYC and interviewed with some small hedging funds. I left behind Regina, we hooked up and had a lot of great sex but never could really go dating with college and everything.

I was uneasy but surefooted at the same time about this move. I had a few rounds of interviews with HPQ consultant and finally I got the job as an analyst. Starting salary was $ 65,000 with performance based bonus. My beginning week Reginold, went by Reggie told me the fillip aren't the only way of getting extra income, Ronnie the owner likes making fiddling bets here or there with staff.
NYC was cracking minus one thing, the price, I had found a two-bedroom apt that one bed way was for rip but it was $ 1,300 per calendar month and I had scholarly person loanword of $ 800 per month. foresightful hours, eating out and socializing left me no room to spare 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 lunch at Bobby Tans 1 pm sharp."

Wow this is so rouse, I get to eat with Ronnie, he was loaded. We sat down and I listened to him and two other business familiar talk about respective issue, most of which made my abdomen turn since it was all about how to easily guide advantage of the poor in the commonwealth etc."So, you like healthcare right now, which origin 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 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 drunkenness and everyone flare-up 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 ploughshare you stop dressing as a man and embark on dressing like a woman in the office."He had a sinister look on his typeface, the other two valet de chambre were quiet and looked intimated. I reached out and rock on it. It was Worth the endangerment for me plus it was trading above 200 it would need a 50 % plus pull out back to hit his telephone number. Come by my government agency when we get back and we will work out the particular.
I had a petty bit of a bad tactile sensation but still confident I could get that $ 20k to pay off my student loanword as I walked into his role. I sat down in front of his desk,"My boy, we need to work out these point, 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 bet ?"“ I owe $ 80,000, you'd be volition to bet that much on one ancestry ?"“ Absolutely boy, how very much 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 woman ?"“ strait like a architectural plan, let's do this, $ 500,000, if you win you get $ 500K, if you lose, you become my striver for sexual favors with me and my friends, you will bet like a woman, make water up, little operation here or there, office slut eccentric looking at, we lost Calluna vulgaris last 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 judgment !"I exclaimed,"$ 1 million in that case, you would be able to help your crime syndicate back home and what are the opportunity the livestock drops to 100, in fact make it 90 and you have to hit 275 ? Think about how easily you can make your life great ! pile or no deal no thinking this one over end of story."I took a deep breath,"Deal !"we shook hands, his right-hand man Henry Martyn Robert spoke up,"ok boys, we have a bet here for a boastfully sum of money, I will draft up the legal paperwork and have you both sign of the zodiac tomorrow evenhandedly enough ?"We both nodded.

My eye was racing as I walked back to my desk, Reggie asked me what was wrong as I looked flushed. I explained to him the wager. He explained to me, that Ronnie loved to progress to those bets, he had won a standardised bet and make $ 100K on the raft. I felt much punter, I closely tracked the Malcolm stock 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 malicious gossip going on etc. Next matter 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 clothing racks etc."My boy, you win some you lose some, I didn't even see that coming this quickly but I also didn't see it hitting $ 275, best way to learn is to get you balls kicked in. In your case, literally, now Renee make him bet pretty,"she looked at me,"seminal fluid with us to the womanhood's locker room in the gym downstairs."My meat was racing, these three beautiful women walked me to the women's locker."Strip down, let's see what we are working with."I turned beat red, I am 5'9"and weight 150 lbs with a lanky body frame."stone's throw in the exhibitor, and knock off your all your hair's-breadth but your oral sex, make sure you get your shit too,"They handed me shaving cream, physical structure washout and shampoo. I took the shower and shaved everything and just stood there, my god what have I done. The woman asked me to spread my impertinence, I did exposing my rosebud,"brand 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 thong and bra. We went back up to the office I went in through the rear into Ronnie's office."Ahh there is my winnings, let's get you into a nice appropriate office attire."He made me model dissimilar clothes off the rack settling on 1.5 inch heels, a Joseph Black wearing apparel with a tight white push down. He had the women leave the office and he sat on the couch."time to start paying up boy, hope you like cock because you're going to make a lot of dick in your life history going forward. I will create sure you are well taken care of, just get make to chug a lot of stopcock"

I looked into the mirror and started to cry, I went from a pretty respectable looking guy, to a blond bimbo in one day. With that he unzipped his pants and pulled out his fellow member. I protested as I cried,"Ryan, no one likes a reverse job where the woman is crying before they even gag. Now you made this bet and could have become fertile, it was Worth the bet for you and this is worth it for me. Now if you don't retain up your end, go back house and start working at the supermarket where your mom is because buss any former career good bye. I can easily end you and your family from any formula existence. Now open up and clear you tears !"

I wiped away my tears and approached his fork, I looked down at his flaccid extremity maybe about 5 inches slightly thick."That a girl, he said, now suck this like the strumpet you are."As he said this he grabbed the back of my promontory and lined it up with his dick."Relax missy, slow your external respiration, my shaft will grow inside your oral fissure but I will slowly bob your head word up and down nicely."I pushed my tongue forward toward the tip and licked it. To my surprise, it didn't taste bad, it was rather salty. I did my best stamp 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 inch as I could.

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

I just wanted this to end, I bobbed furiously, my bridge player caressed his balls, tacky slurping sounds came out of my sassing. He put his script behind my header and I felt him push down harder, his dick must have been about 6 - 6.5 in now and maybe 1.5 column inch wide. I might get been down 4 inches when I felt his tip jibe against the back of my pharynx causing me to gag. He had shoved my head down and with both bridge player behind my head held me plastered. I continued to suffocate, teardrop streamed down and spit flowed from his mouth. He buried my boldness into his os pubis and release quickly allowing me an opportunity to breath as I gasped for air. While trying to catch my intimation he just kept pushing down my nous as I dodged his dick, rubbed my spittle all over my facial expression.
"Isn't life good story, one day you're some democratic college kid banging girls the next you've got your headway buried in some onetime man's crotch while you choke on his pecker and the day after that two dude are using you like a Taiwanese finger's breadth trap ! Now take that cock again and sallow my cum before I shove it in your ass !"With that I realigned my sass over his cock and his thrusted it into my lip. Gagging noises followed as I fought to endure this assault 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 feet.

I looked in the mirror, I looked like a mess. He threw a towel to me and called for Renee to number in."Oh poor baby, well workplace 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 calendar month on the 15th at 10 am. Here is his card. He has a lilliputian work to do on your nada Major just a few items of work. In the meantime, you are to take these pills, they will make anal and other natural action hurt less. Lastly here is a bag with sex toy's butt chew from 2 in to 6 inch that will adulterate your ass for anal sex, please employment up to these"Ronnie stood up,"Now head habitation kid, it's getting late, get a good night's rest to let this settle in."

For the following month, I came into workplace dressed as a charwoman, Reggie just nodded with a bullshit happens around here kind of look. No one seemed shocked at all. Reggie mentioned that like shit happened to heather before she left. My roommate didn't say much, a bit confused at first but I explained the hand and he said he would take taken the pile too. I was really moody and disordered, 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 succeeding morning I took my time getting up, showered, got set up 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 business office. He reassured me everything is reversible, per Ronnie's guild there was a short body of work he wanted but nix John R. Major. I didn't even want to bonk what he had in judgement. He laid me on the table and gave me some gas as I slowly fell asleep.
I awoke in an frightening measure 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 face hurt, my chest injury, my ass hurt. As I looked down there was something on my bureau blocking some of my purview."Ohhh my god, what the fuck did you do !"I yelled out. They gave me breast implants ! What the piece of tail !"I'm going to fucking kill you !"I screamed out, quickly security came into the elbow room and held me down. Dr. Regario walked forward."Ryan, listen here, I have Holy Order paid for from Ronnie your party boss, along with several documents signed by you as division of a bet you two made, he does this shit all the time. He ordered, butt end implants, lip injections, brow facelift, hair implants, lazer hair removal, ass bleaching and cleanup, calfskin implants, chest implants, emasculation and liposuction, nearly of the fat from your mid-section and subdivision in now in your ass. I do give to say you came out pretty damned 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 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 word is, was, not, am, you were a man, after we cut off your globe you just possess what Ronnie birdcall's, a sissy clit left that can't produce sperm. 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 outgrowth this right now, strangely it didn't trauma. My will for getting perturbation was gone, I had no feeling.
Renee was waiting in the entrance hall for me as she helped me pile up my belongings and escorted me to her car. She drove me home,"So is some agitate to see how their beautiful new body looks."I said nothing just sat there crying."Ryan or Reann, take the next month off for retrieval, Ronnie has deposited $ 50,000 into your account to console you. Take it easy, we will transmit food over and everything to ease your recovery. These DVD's are for you to watch and prepare that ass by the way."My roomy was shocked, and just didn't say a Scripture as I walked in with bandages and the obvious transmutation.
About a calendar month later I got ready for work, I really did appear hot, huge titty, fat ass, big lip, small shank everything. My tool used to be around 6 inch now barely 5 and skinny when backbreaking. The DVD was fully of sissy sex and hypno, I used my dildos and butt plugs. For some grounds the dildos really made me cum and even porn did nothing, probably the tablet.

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 wing as everyone was leaving for the day I walked into Ronnie's office."My god you look beautiful ! Let's test those lips out."He said as he undid his knickers. I walked over and got on my knees, I took his hammer in my mouthpiece and bobbed up and down slurping this prison term taking it all no problem."Someone has been practicing I see. God those lips make it so much best"because of those back talk drool was sliding out around his peter and running down my face.
right hand after that I heard the threshold undefended and the cleaning crew came in, I immediately stopped and pulled off mortified. Ronnie grabbed my head,"Don't stop honey ! Hey you two stay a while, isn't she pretty, this is Reann, recollect the Pres Young guy that works here this is him after surgery."He just hold open pumping and a few moments later he pushed my drumhead all the way in and shot a encumbrance deep down my pharynx. I whipped my face for cum and spittle.

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

The two men smiled, with a Spanish people emphasis they said,"Holy shit Ronnie, this was that young new guy, my god you gave him the hottest set of tit an ass I've ever seen on a chick, let alone a clotheshorse. I'm not gay, but fuck that ass looks juicy as infernal region and those back talk 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 birth one up her kitty-cat !"

I looked at them one was tall maybe 6'3"the other one shortly and fat maybe 5'6"both Spanish and kind 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 short strumpet, up on the desk you go, and start sucking."I stood up and the two men pulled my chick and panties down, I froze, they unbuttoned my top and took my bra off."Wow look at those pap !"They pushed me and turn away me over the desk. The tall one walked in front of me and started jerking his tool, it was getting arduous maybe, 8 or 9 inches and really fat. He pushed it into my sassing, I gagged and slurped. The early one started eating out my ass as I moaned. The guy behind stopped licking and walked around with Ronnie,"proceeds a flavor at this hunk of kernel Reann ! And suck that big fat cock !"

As I looked up I thought to myself how is it the short guy has the biggest stopcock. It was hard maybe 10 inches and as thick as my wrist. 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 pull through the cock in my oral fissure. The hawkshaw in was meeting resistor 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 protest, screaming but it was silenced into the prick in my oral fissure as I gasped for air. It pushed against a lot of impedance on my ass but popped past my anal retentive gang letting the head in. I screamed in pain again silenced into the other man's crotch as I tried to wriggle. A wafture of humiliation, infliction and joy swept across me. He just kept pushing, additional split flowed down my buttock."Roque, this ass is so slopped, it's like heaven man you got to try it soon ! Now I am going to wreck this white slice of ass thought fucking clean and jerk this up white boy !"He shouted thrusting about 5 inch in as I jolted forward on the desk, kicking my branch 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 face plowed into the other man's cock showing no relief valve from the prick. He pulled out and rammed it back in getting maybe 8 column inch in, pulling out again before ramming me into the early man's turncock again as his glob slapped against my niggling cock that was just dangling there.

"Wow this is quite a wad, your shaft are impaling this small girl on both remainder like an accordion ! Why don't you lift him up ?"With that I tried to resist but naught helped, they lifted me off the desk and flipped me upside down rotating me in midair, I tried to kick and push a short but they clamped my legs down under the man's axilla and locked me in property, the short-circuit guy lined his dick up again and thrusted in as I screamed out in pain. The other man silenced me quickly ramming his cock down my throat again and they two fucked me furiously."My god smell at his little tool bob around, after all those endocrine and removing those ball its lupus erythematosus a putz and more of an itsy bitsy sissified clitsy !"All the men laughed while I was mercilessly railed out on both final stage. Siliva and spit ran down my cheek the man in my mouth let out a gimcrack groan holding his cock buried down my throat releasing watercourse after current of hot fountain of cum into my belly.

He stayed there as I continued to chock on his cum and shaft. The early man firmly grabbed men around my shank also letting out a load moan, pulling me toward him as hard as he could."Oh my god what a fucking astonishing ass, I going to fill you up !"He shouted as I felt dead reckoning after snap of hot jizz shoot deep into my ass. He pulled back out with a pop, making my ass feel empty and then slammed it right back in as I let out a yelp."Ohh god that ass was amazing."He exclaimed, the man slowly withdrew his cock from my ass as the 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, fagged, 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 spokesperson 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 hobble body,"Reann, Ryan is a good psychoanalyst, but you, god can you require a hammer, Regine, glad you could make it today."Regina looked shocked to see the view in the office."Regina, I believe you might know this little blonde bimbo lying here, this is Ryan, now Reann, he made a bet and let's say he lost Thomas More than just the wager, how do you like the transformation ?

I covered my nerve so as to not see her, she walked over."Ryan is that really you ? Ryan it's me Regina, holy place crap they really did make you a woman."“ Don't aspect at me please Regina."“ It is you I can tell, wow they did some body of work 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 shoulder strap on dildo ready and Regina was stripping down.

"Reann, to really break away you in I needed absolute humiliation, you didn't seem to accept a richly school odorous heart and Regina appeared to be the closelipped 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 hombre to get out.
Renee was helping Regina get on the great strapon. I pleaded and cried,"Regina please don't do this I can't spotter 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 milksop about this and take this shaft !"She said as she pressed the dildo headspring against my ass. This was beyond humiliating, I used to fuck her and always wanted to try anal but not like this. As she pressed harder breaking the barrier of my already loose hole she said,"Reann, call up when you wanted to try anal retentive, well I'm about to divide you in half my little sissy."With that she pushed her weight as the dildo sank in slowly.
Renee spoke up,"Reann encase your wondering this is a 10 inch dildo that is made for prostate gland massages with a curved tip, it is about 2 column inch in diameter right around the middle, or simply put, we don't expect you to total in tomorrow after Regina splits you ass in half, and you're about at the chummy part."right hand as she said that Regina withdrew the frigidness 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 little emasculate clit is dripping precum soft and flopping around while his huge tits just bounce around. You do neat study I must say !"

I looked down liquid was flowing out of my pecker as it danced around, I felt a wave of joy building up in my ass. I started to moan, what was happening to me. My moans and panting grew louder as her dildo bucked against my pelvic arch, she was fucking me like a fantastic womanhood while Ronnie and Renee cheered on. I could only face up at the faces as they stared in a spell 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 stream of cum like a faucet, it pooled all over my tummy.

"There is goes, he fucking came like the little sissy slut he is, only cumming from now on with a decent firm putz up his ass !"Renee exclaimed. Regina kept fucking me for a few more min as I bucked around in pure ecstasy. It was too a good deal 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 get just passed out and in the heating of the mo 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 nookie out, take the day off tomorrow, you've done plenty work today."

Regina and I went out to dinner, I was ashamed and told her the unhurt level. She explained how they called her out of the blue devil 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 deal. She felt bad but a bets a bet and she missed the old me. She did desire to fuck me again, she said it gave her a lot of power, she also wanted to see a guy fulminate me out, perhaps my roommate, guess I know what I am doing tonight at my flat.

The end for now !