I came from a Youngstown OH, my family was really poor growing up and lifetime wasn't easy. My forefather moved out and left us when I was only 10 and my mother supported the menage working at a supermarket during the day and bar tending at night. Since I was really dear at math and managed to get a erudition to Ohio State I found a way out. I got a degree in math with a focal point in statistics. I applied to jobs all over the body politic and got a few salutary interviews lined up in NYC. With the little money I had from my late dark working at a bar I flew out to NYC and interviewed with some pocket-sized hedge funds. 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 surefooted at the same time about this motility. I had a few round of golf of interviews with HPQ adviser and finally I got the job as an analyst. Starting salary was $ 65,000 with performance based bonus. My start week Reginold, went by Reggie told me the bonuses aren't the entirely way of getting extra income, Ronnie the owner likes making fiddling bet here or there with staff.
NYC was majuscule minus one matter, the cost, I had found a two-bedroom apt that one bed room was for rip but it was $ 1,300 per month and I had scholarly person loanword of $ 800 per month. yearn hours, eating out and socializing left me no room to spare from my Cash flow.

I was in the bathroom 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 switch to healthcare sphere, which has worked out quite nicely."“ Yes, sir that was me."“ well why don't you meet me for dejeuner at Bobby Tans 1 pm sharp."

Wow this is so energise, I get to eat with Ronnie, he was loaded. We sat down and I listened to him and two other occupation associates talk about various topic, most of which made my stomach turn since it was all about how to easily take reward of the hapless in the country etc."So, you like healthcare right now, which blood in particular boy ?"“ fountainhead sir Valeantz looks like a becoming 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 deglutition and everyone outburst out laughing at the table myself included.

"Boy let me reword 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 char in the office."He had a sinister facial expression on his face, the former two gentlemen were quiesce and looked intimated. I reached out and escape from on it. It was worth the risk for me plus it was trading above 200 it would necessitate a 50 % plus displume back to hit his phone number. Come by my place when we get back and we will knead out the specifics.
I had a little bit of a bad feeling but still confident I could get that $ 20k to pay off my educatee loans as I walked into his office. I sat down in front of his desk,"My boy, we need to puzzle out out these details, let me ask, I looked over your resume, where you are from etc, how very much do you owe in student loanword and how about that as the wager ?"“ I owe $ 80,000, you'd be unforced to bet that much on one farm animal ?"“ Absolutely boy, how much do you desire on top of that,"“ How about $ 100,000 plus the $ 80,000 if you want me to take the air around like a cleaning lady ?"“ 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 favor with me and my friends, you will look like a woman, attain up, little surgery here or there, office slut type look, we lost Heather last month and she was the post 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 kin back dwelling house and what are the hazard the stock dip to 100, in fact make it 90 and you have to hit 275 ? Think about how easily you can make your spirit bully ! raft or no hand no thinking this one over end of story."I took a deep breath,"spate !"we shook work force, his right-hand man Robert spoke up,"ok boys, we have a bet here for a large sum of money, I will outline up the legal paperwork and have you both augury tomorrow fair enough ?"We both nodded.

My heart was racing as I walked back to my desk, Reggie asked me what was untimely 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 make $ 100K on the mess. I felt much undecomposed, I closely tracked the stock for the few months it hit 257 before quickly plummeting to 175, I thought I was going to cry, when it rallied back a fiddling but there was all this intelligence about malicious gossip going on etc. Next thing I know my pump sank and my testicle pulled up, 110, 100, then it happened it closed at 75. Robert approached me, Ronnie would wish to see you in his position.

I took my walk of life 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, expert way to ascertain is to get you testis kicked in. In your showcase, literally, now Renee make him calculate pretty,"she looked at me,"ejaculate with us to the adult female's locker room in the gym downstairs."My pith was racing, these three beautiful women walked me to the cleaning woman'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."tone in the shower, and shave your all your pilus but your forefront, make indisputable you get your bastard too,"They handed me shaving cream, body wash and shampoo. I took the shower and shaved everything and just stood there, my god what have I done. The adult female asked me to overspread my boldness, I did exposing my rosebud,"Make sure as shooting no whisker is there, now shave it again."They weren't joking around this was for real.
When I stepped out they dried me off and started applying physical composition 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 cover into Ronnie's office."Ahh there is my winnings, let's get you into a prissy appropriate office attire."He made me model different clothes off the rack settling on 1.5 column inch heels, a inglorious dress with a tight white clitoris down. He had the cleaning lady leave the office and he sat on the couch."meter to start paying up boy, hope you like turncock because you're going to have got a lot of gumshoe in your life story going forward. I will earn sure you are well taken care of, just get set to chug a lot of cock"

I looked into the mirror and started to cry, I went from a pretty serious 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 have become rich, 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 household and take off working at the supermarket where your mom is because kiss any former vocation honorable bye. I can easily end you and your folk from any pattern cosmos. Now open up and unclouded you tears !"

I wiped away my tears and approached his genitals, I looked down at his flaccid member maybe about 5 column inch slightly thick."That a girl, he said, now suck this like the slattern you are."As he said this he grabbed the binding of my head and lined it up with his gumshoe."Relax girl, slow your ventilation, my cock will grow inside your mouth but I will slowly bob your read/write head up and down nicely."I pushed my knife forward toward the tip and licked it. To my surprise, it didn't appreciation bad, it was rather salty. I did my best belief on what I say from the porn I've watched and took the head in fully. He moaned in acceptation and I just bobbed up and down slowly working in as many in as I could.

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

I just wanted this to end, I bobbed furiously, my hands caressed his clump, tawdry slurping phone came out of my mouth. He put his hand behind my head and I felt him labour down harder, his dick must have been about 6 - 6.5 inches now and maybe 1.5 inches astray. I might have been down 4 in when I felt his tip slam against the back of my pharynx causing me to gag. He had shoved my head down and with both hands behind my oral sex held me smashed. I continued to choke, tears streamed down and saliva flowed from his lip. He buried my face into his pubes and press 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 caput as I dodged his hammer, rubbed my tongue all over my face.
"Isn't life funny, one day you're some democratic college kid banging girls the next you've got your point buried in some senior man's genital organ while you choke on his cock and the day after that two clotheshorse are using you like a Chinese finger bunker ! Now take that tool again and sallow my cum before I shove it in your ass !"With that I realigned my lip over his peter and his thrusted it into my mouth. Gagging noises followed as I fought to live this assault on my oral cavity. 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 metrical unit.

I looked in the mirror, I looked like a pile. He threw a towel to me and called for Renee to follow in."Oh short child, well oeuvre on that gag reflex so you look like less of a working girl when you're done. Here is your travelling bag with you outfit for tomorrow. Please see Dr. Regario next calendar month on the 15th at 10 am. Here is his visiting card. He has a little work to do on your nothing John R. Major just a few items of workplace. In the meantime, you are to learn these pills, they will micturate anal and former bodily process hurt less. Lastly here is a bag with sex toy's butt plugs from 2 in to 6 column inch 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 effective Nox's rest to let this settle in."

For the next month, I came into employment dressed as a woman, Reggie just nodded with a shit happens around here kind of looking at. No one seemed shocked at all. Reggie mentioned that Lapplander shit happened to heather before she left. My roommate didn't say much, a bit mixed-up at first but I explained the deal and he said he would have taken the deal too. I was really Helen Wills and perturbation, but Ronnie didn't do anything else that was sexual. I gained a crowd of weight probably from eating and being depressed. I noticed on my calendar the Doctor's date was for tomorrow.

The side by side morning I took my clip getting up, showered, got quick 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 reversible, per Ronnie's club there was a picayune work he wanted but zilch 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 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 face hurt, my chest trauma, my ass detriment. As I looked down there was something on my chest blocking some of my view."Ohhh my god, what the ass 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 security came into the room and held me down. Dr. Regario walked forward."Ryan, listen here, I have orders paid for from Ronnie your foreman, along with several written document signed by you as part of a bet you two made, he does this rat all the time. He ordered, buttocks implants, lip injection, eyebrow lifts, hair implants, lazer hair's-breadth removal, ass bleaching and cleansing, calf implants, white meat implants, castration and liposuction, nigh of the fat from your mid-section and arms in now in your ass. I do have to say you came out pretty damn hot though !"

My mettle sank and I passed out. I awoke again."That happened a lot around here, perfectly convention. Those internal secretion you were taking really helped in making your tits threefold ds by the way, they gave us just enough tissue paper around the edges."I thought I was dreaming earlier until he made that gossip. I just started to cry."Doctor of the Church you can't leave me like this, I am a man, I can't go base like this."The Dr looked at me"Well the key word is, was, not, am, you were a man, after we cut off your balls you just birth what Ronnie vociferation's, a sissy clit left that can't green goods sperm. And all these text file here protect me, you should read more carefully when betting with Ronnie."

Oh, my god, they cut off my balls, I couldn't process this right now, strangely it didn't hurt. My will for getting turnover was gone, I had no feeling.
Renee was waiting in the lobby for me as she helped me gather my holding and escorted me to her car. She drove me family,"So is some excited 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 write up to console you. Take it comfortable, we will send intellectual nourishment over and everything to ease your retrieval. These DVD's are for you to watch and train that ass by the way."My roomy was shocked, and just didn't say a word as I walked in with bandages and the obvious transformation.
About a month later I got gear up for work, I really did wait hot, huge mamilla, fat ass, big back talk, lowly waist everything. My stopcock used to be around 6 inches now barely 5 and skinny when hard. The DVD was fully of sissy sex and hypno, I used my dildos and buns plugs. For some reason the dildos really made me cum and unconstipated porno did null, probably the contraceptive pill.

When I arrived back at work I got a lot of looking at. I went to my desk and cried. Reggie came over,"Reann, it's not that bad, you look so pretty, you should be glad. Ronnie wants to see you after work."

Right as everyone was leaving for the day I walked into Ronnie's part."My god you look beautiful ! Let's test those lips out."He said as he undid his bloomers. I walked over and got on my knees, I took his putz in my mouth and bobbed up and down slurping this sentence taking it all no problem."mortal has been practicing I see. God those sassing make it so much better"because of those back talk drool was sliding out around his cock and running down my face.
Right after that I heard the threshold undefendable and the cleaning crew came in, I immediately stopped and pulled off mortified. Ronnie grabbed my fountainhead,"Don't stop honey ! Hey you two stay a patch, isn't she pretty, this is Reann, remember the young guy that works here this is him after surgery."He just keep pumping and a few instant later he pushed my head all the way in and fool a burden 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 firstly cock, how about you two help me break him in. His ass has to be tight as hellhole, look at it an early Christmas Day present."I could hear them walking over as Ronnie let up on my head.

The two men smiled, with a Spanish people accent they said,"holy place shit Ronnie, this was that young new guy, my god you gave him the hottest set of breast an ass I've ever seen on a chick, let alone a dude. 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 cock in your ass, Reann is the only when one in the elbow room that will have one up her pussy !"

I looked at them one was tall maybe 6'3"the early one shortly and fat maybe 5'6"both Spanish and form 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 start sucking."I stood up and the two men pulled my chick and scanty down, I froze, they unbuttoned my top and took my bra off."Wow tone at those tits !"They pushed me and deform me over the desk. The tall one walked in front of me and started jerking his tool, it was getting backbreaking maybe, 8 or 9 in 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 core Reann ! And suck that big fat cock !"

As I looked up I thought to myself how is it the shortly guy has the biggest hammer. It was gruelling maybe 10 column inch 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 pleasance while trying to subsist the putz in my mouth. 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 dick head at my ass, I tried to resist, screaming but it was silenced into the cock in my mouth as I gasped for air. It pushed against a lot of resistance on my ass but popped past my anal mob letting the caput in. I screamed in pain again silenced into the other man's crotch as I tried to squirm. A wave of chagrin, pain and pleasure swept across me. He just kept pushing, extra split flowed down my impertinence."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 Caucasian piece of ass thought fucking clean and jerk this up white boy !"He shouted thrusting about 5 column inch in as I jolted forward on the desk, kicking my legs up in the air.

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

"Wow this is quite a plenty, your cocks are impaling this small girl on both end like an accordion ! Why don't you lift him up ?"With that I tried to protest 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 little but they clamped my peg down under the man's axillary cavity and locked me in place, the inadequate guy lined his cock 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 tone at his little shaft bob around, after all those hormones and removing those balls its less a cock and Thomas More of an itsy bitsy sissy clitsy !"All the men laughed while I was mercilessly railed out on both remainder. Siliva and spit ran down my cheeks the man in my oral cavity let out a aloud moan holding his rooster buried down my pharynx releasing stream after stream of hot honey oil of cum into my belly.

He stayed there as I continued to chock on his cum and cock. The former man firmly grabbed men around my waist also letting out a burden moan, pulling me toward him as hard as he could."Oh my god what a fucking flummox ass, I going to meet you up !"He shouted as I felt shot after shooter 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 cock from my ass as the other guy pulled out of my oral cavity. I could feel a watercourse of cum trickeling out of my ass. I collapsed on the desk after they let me down, exhausted, ashamed and humiliated as I lost my anal retentive virginity.

I heard the door surface again, I could hear Renee talking and I knew the early voice too. I glanced over and saw Regina talking to Renee, what the hell was she doing here in New House of York. Ronnie walked over to my limp body,"Reann, Ryan is a practiced analyst, but you, god can you take a cock, Regine, sword lily you could make it today."Regina looked shocked to see the scene in the office."Regina, I believe you might bang 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 shift ?

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

"Reann, to really expose you in I needed inviolable humiliation, you didn't seem to have a high shoal odorous heart and Regina appeared to be the closest matter, 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 sustenance bozo 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 picket you fuck me like this you can't !"She approached lathering the dildo in lube, Renee and Ronnie lifted my pegleg up in the air exposing my cum dripping ass."Reann, you're a woman now, your not the guy I used to have it off, now stop being a little sissy about this and lease this cock !"She said as she pressed the dildo head 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 barrier of my already loose golf hole she said,"Reann, recollect when you wanted to try anal, well I'm about to split 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 gland massages with a curved tip, it is about 2 inches in diameter right around the eye, or simply put, we don't expect you to fall in tomorrow after Regina splits you ass in one-half, and you're about at the stocky part."rightfulness as she said that Regina withdrew the moth-eaten 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, look what you did, his trivial emasculate clitoris is dripping precum easy and flopping around while his huge boob just bounciness around. You do dandy work I must say !"

I looked down liquid was flowing out of my pecker as it danced around, I felt a wave of pleasure building up in my ass. I started to moan, what was happening to me. My moans and panting grew louder as her dildo bucked against my rosehip, she was fucking me like a wild fair sex while Ronnie and Renee cheered on. I could only front up at the faces as they stared in a spell at the vast 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 prick started to let out a current 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 nice house putz up his ass !"Renee exclaimed. Regina kept fucking me for a few more transactions as I bucked around in pure exaltation. It was too much I collapsed as she kept fucking me. I finally came too as they were all dressed and I was still naked on the lounge now.

"Reann, I am disconsolate I guess you must take just passed out and in the heat of the moment we didn't posting. 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 body of work today."

Regina and I went out to dinner, I was ashamed and told her the completely tale. She explained how they called her out of the blue and offer $ 100,000 to fuck you and an extra $ 50,000 if I really humiliated you. I didn't blame her for taking the plenty. She felt bad but a bets a bet and she missed the old me. She did want to lie with 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 apartment.

The end for now !