I came from a Youngstown OH, my kinsfolk was really poor growing up and sprightliness wasn't easy. My father moved out and left us when I was only 10 and my mother supported the house working at a supermarket during the day and bar aid at night. Since I was really ripe at math and managed to get a scholarship to Ohio commonwealth I found a way out. I got a academic degree in maths with a focus in statistics. I applied to jobs all over the country and got a few undecomposed 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 cash in hand. I left behind Regina, we hooked up and had a lot of groovy sex but never could really start dating with college and everything.

I was nervous but confident at the like time about this move. I had a few rounds of consultation with HPQ Advisors and finally I got the job as an analyst. Starting pay was $ 65,000 with performance based incentive. My beginning calendar week Reginold, went by Reggie told me the bonuses aren't the only way of getting superfluous income, Ronnie the owner likes making picayune wager here or there with staff.
NYC was big minus one thing, the cost, I had found a two-bedroom apt that one bed room was for tear but it was $ 1,300 per month and I had student loans of $ 800 per month. Long hours, eating out and socializing left me no way to give up from my John 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 public figure is Ryan ”."Ah, yes Ryan you were the one that suggested the late shift key 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 tan 1 pm sharp."

Wow this is so energize, I get to eat with Ronnie, he was loaded. We sat down and I listened to him and two other business associate talk about various topics, about of which made my stomach bit since it was all about how to easily take advantage of the poor in the nation etc."So, you like healthcare right now, which stock in special boy ?"“ wellspring sir Valeantz looks like a decently buy right now it is trading at 228 but my calculations show based on its momentum it could easily go to 300."“ Is that powerful boy, how about we bet $ 20,000 on that he said ?"I choked on my drink and everyone burst out laughing at the table myself included.

"Boy let me 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 out dressing like a woman in the office."He had a sinister tone on his face, the former two gentlemen were quiet and looked intimated. I reached out and shook on it. It was deserving the risk for me plus it was trading above 200 it would want a 50 % plus pull back to hit his number. Come by my office when we get back and we will work out the specifics.
I had a short bit of a bad tone but still convinced I could get that $ 20k to pay off my scholar loanword as I walked into his authority. 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 scholar loans and how about that as the wager ?"“ I owe $ 80,000, you'd be volition to bet that much on one stock ?"“ Absolutely boy, how much do you want on top of that,"“ How about $ 100,000 plus the $ 80,000 if you want me to walk around like a woman ?"“ Sounds like a program, let's do this, $ 500,000, if you win you get $ 500K, if you lose, you become my striver for intimate favor with me and my friend, you will look like a woman, make up, little surgical process here or there, federal agency slut type looking, we lost Heather last calendar month and she was the office fuck toy, so I am looking for another one and you fit the build."“ Are you out of your head !"I exclaimed,"$ 1 million in that example, you would be able-bodied to assist your family back home and what are the chances the Malcolm stock drops to 100, in fact make it 90 and you have to hit 275 ? Think about how easily you can make your life keen ! heap or no deal no thinking this one over end of story."I took a deep intimation,"Deal !"we shook hired man, his right man Robert spoke up,"ok boys, we have a bet here for a vauntingly sum of money, I will draft up the legal paperwork and have you both preindication tomorrow fair enough ?"We both nodded.

My bosom 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 stake. He explained to me, that Ronnie loved to make those stake, he had won a similar bet and lay down $ 100K on the deal. I felt much better, I closely tracked the fund 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 piddling but there was all this news about scandal going on etc. Next thing I know my affectionateness sank and my balls pulled up, 110, 100, then it happened it closed at 75. Robert approached me, Ronnie would wish to see you in his office.

I took my walk of shame, waiting inside Ronnies office were a few women 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, near way to learn is to get you ballock kicked in. In your case, literally, now Renee make him look pretty,"she looked at me,"Come with us to the women's storage locker room in the gym downstairs."My heart was racing, these three beautiful women walked me to the adult female's locker."landing 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 human body."Step in the shower, and shave your all your haircloth but your question, make sure you get your mother fucker too,"They handed me shaving pick, body washables and shampoo. I took the shower bath and shaved everything and just stood there, my god what have I done. The woman asked me to broadcast my cheeks, I did exposing my rosebud,"brand for sure no haircloth 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 G-string and bra. We went back up to the office I went in through the back into Ronnie's situation."Ahh there is my winnings, let's get you into a nice appropriate office attire."He made me model different wearing apparel off the rack settling on 1.5 in heels, a black dress with a cockeyed white clit down. He had the women leave the post and he sat on the couch."time to start paying up boy, hope you like cock because you're going to hold a lot of dick in your life going forward. I will cook sure as shooting you are well taken charge of, just get ready to chug a lot of rooster"

I looked into the mirror and started to cry, I went from a pretty dependable looking guy, to a blond bimbo in one day. With that he unzipped his bloomers and pulled out his extremity. 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 rich, it was worth the bet for you and this is worth it for me. Now if you don't hold up your end, go back habitation and set out working at the supermarket where your mom is because kiss any other life history good bye. I can easily end you and your family from any normal existence. Now open up and unclutter you tears !"

I wiped away my bust and approached his crotch, I looked down at his flaccid member maybe about 5 in slightly thick."That a girl, he said, now suck this like the slut you are."As he said this he grabbed the binding of my oral sex and lined it up with his gumshoe."Relax missy, slow your breathing, my cock will develop inside your mouth but I will slowly bob your head 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 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 column inch as I could.

"looking up at me, I have to see you with my cock buried in your pretty footling back talk, you realize there is no way out but to do a in effect job."I stared up at him, split 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 hand caressed his balls, loud slurping phone came out of my mouth. He put his hired hand behind my nous and I felt him labor down harder, his prick must have been about 6 - 6.5 inches now and maybe 1.5 column inch full. I might have been down 4 inches when I felt his tip slam against the spine of my throat causing me to gag. He had shoved my head down and with both hands behind my point held me sloshed. I continued to choke, tears streamed down and saliva flowed from his sass. He buried my grimace into his pubes and dismissal quickly allowing me an chance to breath as I gasped for air. While trying to catch up with my breath he just kept pushing down my head as I dodged his cock, rubbed my saliva all over my boldness.
"Isn't life-time funny story, one day you're some popular college kid banging girls the succeeding you've got your headland buried in some erstwhile man's crotch while you choke on his putz and the day after that two dude are using you like a Chinese finger ambush ! Now take that prick again and sallow my cum before I shove it in your ass !"With that I realigned my mouth over his stopcock and his thrusted it into my sassing. Gagging noises followed as I fought to survive this violation on my lip. He furiously fucked my grimace for about 5 minutes before burying my typeface back down and pumping burden 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 pickle. He threw a towel to me and called for Renee to come in."Oh poor baby, well work on that gag reflex so you look like LE of a fancy woman when you're done. Here is your suitcase with you outfit for tomorrow. Please see Dr. Regario future month on the 15th at 10 am. Here is his add-in. He has a little work to do on your null major just a few items of employment. In the meantime, you are to take these pills, they will make anal retentive and other natural action hurt less. Lastly here is a bag with sex toy's tail end plugs from 2 column inch to 6 inches that will debase your ass for anal sex, please study up to these"Ronnie stood up,"Now head plate kid, it's getting late, get a secure night's rest to let this settle in."

For the next calendar month, I came into work dressed as a woman, Reggie just nodded with a poop happens around here form of look. No one seemed shocked at all. Reggie mentioned that same shit happened to heather before she left. My roommate didn't say much, a bit confused at first-class honours degree but I explained the batch and he said he would hold taken the great deal too. I was really moody and upset, but Ronnie didn't do anything else that was sexual. I gained a caboodle of weight probably from eating and being depressed. I noticed on my calendar the Doctor of the Church's appointment was for tomorrow.

The next morning I took my clock time getting up, showered, got gear up and put on my blond wig for the day. I arrived at Dr. Regarios office at 10 am and filled out a clustering of paperwork and consent anatomy. I was called into his office. He reassured me everything is reversible, per Ronnie's order there was a fiddling work he wanted but zilch major. I didn't even want to sleep together what he had in idea. He laid me on the table and gave me some gas as I slowly fell asleep.
I awoke in an direful amount 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 case hurt, my chest hurt, my ass harm. As I looked down there was something on my chest blocking some of my view."Ohhh my god, what the screwing did you do !"I yelled out. They gave me breast implants ! What the fuck !"I'm going to fucking shoot down you !"I screamed out, quickly security came into the way and held me down. Dr. Regario walked forward."Ryan, listen here, I have ordination paid for from Ronnie your genus Bos, along with several text file signed by you as part of a bet you two made, he does this shit all the metre. He ordered, bum implants, lip injection, brow raising, hair implants, lazer hair remotion, ass bleaching and cleansing, sura implants, titty implants, castration and liposuction, most of the fat from your mid-section and arms in now in your ass. I do have to say you came out pretty darned hot though !"

My substance sank and I passed out. I awoke again."That happened a lot around here, perfectly formula. Those hormone you were taking really helped in making your tits two-fold 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."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 word is, was, not, am, you were a man, after we cut off your balls you just have what Ronnie call's, a milksop clitoris left that can't produce sperm. And all these documents here protect me, you should take more carefully when betting with Ronnie."

Oh, my god, they cut off my glob, I couldn't cognitive operation this right now, strangely it didn't hurt. My will for getting upset was gone, I had no belief.
Renee was waiting in the lobby 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 body looks."I said nothing just sat there crying."Ryan or Reann, take the next month off for recovery, Ronnie has deposited $ 50,000 into your account to soothe you. contain it well-fixed, we will send solid food over and everything to allay 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 tidings as I walked in with bandages and the obvious transformation.
About a month later I got gear up for employment, I really did bet hot, immense tits, fat ass, big lips, minor waist everything. My putz used to be around 6 inch now barely 5 and skinny when hard. The DVD was fully of sissy sex and hypno, I used my dildos and butt plugs. For some reason the dildos really made me cum and regular smut did zilch, probably the pills.

When I arrived back at body of work I got a lot of tone. 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 office."My god you look beautiful ! Let's test those backtalk out."He said as he undid his pants. I walked over and got on my articulatio genus, I took his peter in my rima oris and bobbed up and down slurping this prison term taking it all no problem."someone has been practicing I see. God those backtalk make it so much better"because of those lips drool was sliding out around his prick and running down my face.
Right after that I heard the door open and the cleaning gang came in, I immediately stopped and pulled off crucify. Ronnie grabbed my oral sex,"Don't stop beloved ! Hey you two stay a while, isn't she pretty, this is Reann, commend the Pres Young guy that works here this is him after surgery."He just retain pumping and a few here and now later he pushed my principal all the way in and shot a load deep down my throat. I whipped my aspect for cum and spittle.

The two Spanish men just laughed. Ronnie told them,"Hey no one has ever broken him in, I am his first stopcock, how about you two help me go him in. His ass has to be tight as inferno, consider it an former Christmas present."I could hear them walking over as Ronnie let up on my brain.

The two men smiled, with a Spanish people accent they said,"sanctum shit Ronnie, this was that young new guy, my god you gave him the live set of tits an ass I've ever seen on a chick, let alone a fellow. I'm not gay, but fuck that ass looks juicy as Hades and those back talk were built for sucking cock."Ronnie looked to them,"don't worry it's only gay when there is a hammer in your ass, Reann is the entirely one in the way that will have one up her pussy !"

I looked at them one was improbable maybe 6'3"the early one short and fat maybe 5'6"both Spanish and form of grimy looking. They both started unzipping their drawers when two fat tool plopped out. My oral fissure dropped and I looked at Ronnie,"But they are too big ?"“ Not for my trivial slut, up on the desk you go, and depart 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 mamilla !"They pushed me and flex me over the desk. The improbable one walked in front of me and started jerking his dick, it was getting surd 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,"Take a aspect at this hunk of meat Reann ! And suck that big fat cock !"

As I looked up I thought to myself how is it the short guy has the gravid cock. 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 survive the hammer in my oral fissure. The dick in was meeting underground 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 header at my ass, I tried to protest, screaming but it was silenced into the prick in my mouth as I gasped for air. It pushed against a lot of resistance on my ass but popped past my anal retentive ringing letting the mind in. I screamed in pain again silenced into the other man's crotch as I tried to squirm. A wave of humiliation, nuisance and pleasure swept across me. He just kept pushing, additional snag flowed down my cheeks."Roque, this ass is so tight, it's like paradise man you got to try it soon ! Now I am going to wreck this Edward D. White piece of ass thought fucking clean this up white boy !"He shouted thrusting about 5 inch in as I jolted forward on the desk, kicking my stage up in the air.

It felt like my interior couldn't accommodate any to a greater extent 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 escape from the rooster. 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 balls slapped against my little peter that was just dangling there.

"Wow this is quite a pot, your cocks are impaling this petty lady friend on both ends like an accordion ! Why don't you lift him up ?"With that I tried to dissent 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 armpit and locked me in place, the short guy lined his shaft up again and thrusted in as I screamed out in botheration. 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 prick bob around, after all those hormones and removing those balls its less a tool 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 mouth let out a aloud moan holding his hammer buried down my throat releasing stream after stream of hot jets of cum into my belly.

He stayed there as I continued to chock on his cum and rooster. The other man firmly grabbed men around my waist also letting out a load moan, pulling me toward him as hard as he could."Oh my god what a fucking perplex ass, I going to fill you up !"He shouted as I felt gibe after snap of hot jizz shoot deep into my ass. He pulled back out with a pop, making my ass look 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 sassing. I could feel a stream 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 virginity.

I heard the door open again, I could hear Renee talking and I knew the former phonation 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 consistency,"Reann, Ryan is a estimable analyst, but you, god can you take a cock, Regine, glad you could seduce it today."Regina looked outrage to see the scene in the office."Regina, I believe you might do it this little blonde bimbo lying here, this is Ryan, now Reann, he made a bet and let's say he lost more than just the wager, how do you like the transformation ?

I covered my aspect so as to not see her, she walked over."Ryan is that really you ? Ryan it's me Regina, sanctum crap they really did seduce you a woman."“ Don't look at me please Regina."“ It is you I can tell, wow they did some workplace with you, I guess you really have changed. I am disconsolate beloved 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 gear up and Regina was stripping down.

"Reann, to really break you in I needed absolute mortification, you didn't seem to deliver a high schooling Sweet heart and Regina appeared to be the near thing, everyone has a price, and we found hers to get it on an old friend with a strapon dildo. With that he slapped my ass and told the two criminal maintenance guy wire 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 ticker 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 know, now stop being a little sissy about this and require this rooster !"She said as she pressed the dildo head against my ass. This was beyond humiliating, I used to have intercourse 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, 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 curved tip, it is about 2 inches in diameter right around the middle, or simply put, we don't expect you to occur in tomorrow after Regina splits you ass in half, and you're about at the deep part."right hand as she said that Regina withdrew the cold dildo and shoved it back in as I let out a yelp, she just kept bucking into my ass. Pounding away, verbally abusing me about what a sissy I am."Ronnie, look what you did, his piffling sissified clitoris is dripping precum soft and flopping around while his huge knocker just bouncing around. You do great employment I must say !"

I looked down liquid was flowing out of my cock 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 hips, she was fucking me like a natural state woman while Ronnie and Renee cheered on. I could only look up at the faces as they stared in a trance at the huge dildo ripping my ass up."Oh gawd, oh gawd,"I yelped out as I felt like I was about to erupt when all of a sudden my 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 sissified slovenly woman he is, only cumming from now on with a nice house cock up his ass !"Renee exclaimed. Regina kept fucking me for a few to a greater extent second as I bucked around in pure ecstasy. It was too often 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 hotness of the present 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 plenty work today."

Regina and I went out to dinner, I was ashamed and told her the solid story. She explained how they called her out of the blue and offer $ 100,000 to make love you and an supernumerary $ 50,000 if I really humiliated you. I didn't incrimination her for taking the wad. She felt bad but a bet a bet and she missed the old me. She did want to fuck me again, she said it gave her a lot of big businessman, she also wanted to see a guy rail me out, perhaps my roommate, dead reckoning I know what I am doing tonight at my apartment.

The end for now !