I came from a Youngstown OH, my folk was really misfortunate growing up and life wasn't easy. My father moved out and left us when I was only 10 and my female parent supported the kin working at a supermarket during the day and bar tending at Nox. Since I was really good at maths and managed to get a learning to Ohio State I found a way out. I got a academic degree in maths with a focusing in statistics. I applied to jobs all over the country and got a few estimable consultation lined up in NYC. With the lilliputian money I had from my late dark 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 cracking sex but never could really start dating with college and everything.

I was nervous but confident at the same time about this move. I had a few rounds of interviews with HPQ Advisors and finally I got the job as an analyst. Starting salary was $ 65,000 with performance based fillip. My first hebdomad Reginold, went by Reggie told me the incentive aren't the only way of getting extra income, Ronnie the owner likes making little bets here or there with staff.
NYC was great minus one thing, the toll, I had found a two-bedroom apt that one bed way was for rent 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 room to spare from my cash flow.

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

Wow this is so wind up, I get to eat with Ronnie, he was loaded. We sat down and I listened to him and two other business organization associates talk about versatile topics, nearly of which made my stomach turn since it was all about how to easily ingest reward of the poor in the country etc."So, you like healthcare right now, which stock in particular boy ?"“ fountainhead sir Valeantz looks like a decent buy right now it is trading at 228 but my computing show based on its impulse it could easily go to 300."“ Is that correct boy, how about we bet $ 20,000 on that he said ?"I choked on my drunkenness and everyone burst out laughing at the table myself included.

"Boy let me reword that, if it hits 300 per plowshare you get $ 20K, if it hits 100 per parcel you stop dressing as a man and commence dressing like a woman in the office."He had a sinister looking on his face, the early two gentlemen were quiet and looked intimated. I reached out and shook on it. It was Worth the endangerment for me plus it was trading above 200 it would need a 50 % plus pull back to hit his identification number. Come by my federal agency when we get back and we will figure out 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 position. I sat down in front of his desk,"My boy, we need to figure out out these details, let me ask, I looked over your resume, where you are from etc, how often do you owe in student loans and how about that as the wager ?"“ I owe $ 80,000, you'd be willing to bet that much on one stock ?"“ Absolutely boy, how a great deal do you want 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 plan, let's do this, $ 500,000, if you win you get $ 500K, if you lose, you become my hard worker for sexual favors with me and my friends, you will look like a fair sex, stimulate up, small surgery here or there, spot adulteress type smell, we lost Heather 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 head !"I exclaimed,"$ 1 million in that case, you would be capable to help your phratry back household and what are the chances the line drops to 100, in fact make it 90 and you have to hit 275 ? intend about how easily you can make your life large ! hand or no deal no thinking this one over end of story."I took a deep breath,"Deal !"we shook bridge player, his right man Robert spoke up,"ok boys, we have a bet here for a large sum of money, I will draft up the sound paperwork and have you both sign tomorrow fair enough ?"We both nodded.

My heart 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 do those bet, he had won a similar bet and make $ 100K on the deal. I felt much easily, I closely tracked the farm animal for the few months 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 program about outrage going on etc. adjacent thing I know my philia sank and my balls pulled up, 110, 100, then it happened it closed at 75. Henry Martyn Robert approached me, Ronnie would like to see you in his position.

I took my walkway of shame, waiting inside Ronnies office were a few woman 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 get a line is to get you balls kicked in. In your caseful, literally, now Renee make him look pretty,"she looked at me,"Come with us to the women's locker room in the gym downstairs."My nitty-gritty was racing, these three beautiful womanhood walked me to the women's locker."comic 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."stair in the exhibitor, and shave your all your hair but your head, make indisputable you get your asshole too,"They handed me shaving cream, trunk dry wash 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 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 bureau I went in through the back into Ronnie's office."Ahh there is my winnings, let's get you into a decent seize part attire."He made me simulate unlike clothes off the rack settling on 1.5 inch heels, a pitch-black dress with a soaked white clitoris down. He had the women leave the office and he sat on the sofa."sentence to start paying up boy, hope you like shaft because you're going to have a lot of dick in your life going forward. I will have sure you are well taken fear of, just get ready to chug a lot of cock"

I looked into the mirror and started to cry, I went from a pretty goodness 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 blow job where the woman is crying before they even gag. Now you made this bet and could have become rich, it was deserving the bet for you and this is deserving it for me. Now if you don't moderate up your end, go back home and start working at the supermarket where your mom is because kiss any early career good bye. I can easily end you and your kinsperson from any normal existence. Now open up and earn you tears !"

I wiped away my tears and approached his crotch, I looked down at his flaccid penis maybe about 5 inches slightly thick."That a girl, he said, now suck this like the slovenly woman you are."As he said this he grabbed the back of my head and lined it up with his dick."Relax girlfriend, slow your ventilation, my cock will farm inside your sass but I will slowly bob your head up and down nicely."I pushed my tongue forward toward the tip and licked it. To my surprisal, it didn't gustatory perception bad, it was rather salty. I did my best impression on what I say from the pornos I've watched and took the nous in fully. He moaned in acceptance 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 prick slowly growing inside my back talk.

I just wanted this to end, I bobbed furiously, my hands caressed his orchis, flash slurping audio came out of my oral cavity. He put his hand behind my head and I felt him labor down harder, his dick must have been about 6 - 6.5 inches now and maybe 1.5 inches wide. I might have got been down 4 in when I felt his tip slam against the back of my throat causing me to gag. He had shoved my chief down and with both workforce behind my head held me smashed. I continued to cash in one's chips, tears streamed down and spittle flowed from his mouth. He buried my expression into his pubes and release quickly allowing me an chance to breath as I gasped for air. While trying to catch my breath he just kept pushing down my head as I dodged his cock, rubbed my spit all over my face.
"Isn't animation funny, one day you're some popular college kid banging girl the next you've got your foreland buried in some older man's private parts while you choke on his pecker and the day after that two dude are using you like a Chinese finger trap ! Now take that cock again and sallow my cum before I shove it in your ass !"With that I realigned my oral fissure over his cock and his thrusted it into my mouth. Gagging disturbance followed as I fought to survive this violation on my mouth. He furiously fucked my face for about 5 minutes before burying my face back down and pumping scads 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 come in."Oh short infant, well employment on that gag reflex so you look like less of a whore when you're done. Here is your traveling bag with you outfit for tomorrow. Please see Dr. Regario next month on the 15th at 10 am. Here is his poster. He has a picayune oeuvre to do on your nil John Major just a few particular of work. In the meantime, you are to take these pills, they will shit anal and other action hurt less. Lastly here is a bag with sex toy's stern spark plug from 2 column inch to 6 inches that will stretch your ass for anal sex, please employment up to these"Ronnie stood up,"Now head home kid, it's getting late, get a good night's residual to let this settle in."

For the next month, I came into body of work dressed as a adult female, Reggie just nodded with a poop happens around here kind of aspect. No one seemed shocked at all. Reggie mentioned that same damn happened to heather before she left. My roomie didn't say much, a bit confused at first but I explained the deal and he said he would have got taken the deal too. I was really sour and bowl over, 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 MD's appointment was for tomorrow.

The succeeding cockcrow I took my clock time getting up, showered, got ready 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 situation. He reassured me everything is two-sided, per Ronnie's order there was a footling work he wanted but nothing major. I didn't even want to live 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 fearful amount of botheration, 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 side hurt, my breast hurt, my ass damage. 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 piece of ass !"I'm going to fucking kill you !"I screamed out, quickly security measures came into the room and held me down. Dr. Regario walked forward."Ryan, listen here, I have fiat paid for from Ronnie your boss, along with several documents signed by you as part of a bet you two made, he does this shit all the time. He ordered, backside implants, lip injections, eyebrow lifts, hair implants, lazer hair removal, ass bleaching and cleansing, calf implants, breast implants, castration and liposuction, near of the fat from your mid-section and arms in now in your ass. I do bear to say you came out pretty deuced hot though !"

My spunk 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 teat duplicate ds by the way, they gave us just enough tissue paper around the edges."I thought I was dreaming earlier until he made that comment. I just started to cry."physician you can't leave me like this, I am a man, I can't go place like this."The Dr looked at me"Well the key word is, was, not, am, you were a man, after we cut off your chunk you just have what Ronnie vociferation's, a sissy clit left that can't green goods sperm cell. And all these document 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 damage. My will for getting upset was gone, I had no spirit.
Renee was waiting in the foyer for me as she helped me amass my holding and escorted me to her car. She drove me rest home,"So is some energize to see how their beautiful new body looks."I said nothing just sat there crying."Ryan or Reann, take the following month off for recovery, Ronnie has deposited $ 50,000 into your history to solace you. Take it well-off, we will send food over and everything to allay your recovery. These DVD's are for you to watch over and civilize that ass by the way."My roomy was shocked, and just didn't say a word as I walked in with bandage and the obvious translation.
About a month later I got prepare for work, I really did depend hot, huge boob, fat ass, big brim, pocket-sized waist everything. My cock used to be around 6 inches now barely 5 and skinny when knockout. 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 porn did nothing, probably the pills.

When I arrived back at employment I got a lot of smell. 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 field as everyone was leaving for the day I walked into Ronnie's power."My god you look beautiful ! Let's mental testing those lips out."He said as he undid his pants. I walked over and got on my knees, I took his cock in my back talk and bobbed up and down slurping this meter taking it all no problem."someone has been practicing I see. God those lips make it so much meliorate"because of those backtalk drool was sliding out around his cock and running down my face.
right hand after that I heard the threshold open and the cleaning crew came in, I immediately stopped and pulled off necrose. Ronnie grabbed my head,"Don't stoppage honey ! Hey you two stay a piece, isn't she pretty, this is Reann, remember the young guy that works here this is him after surgery."He just observe pumping and a few instant later he pushed my school principal all the way in and tear a shipment 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 prick, how about you two help me relegate him in. His ass has to be tight as hellhole, consider it an early Christmastide 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,"sanctum shit Ronnie, this was that immature new guy, my god you gave him the hottest set of breast an ass I've ever seen on a dame, let alone a dude. I'm not gay, but fuck that ass looks juicy as hell and those sass 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 way that will get one up her pussy !"

I looked at them one was grandiloquent maybe 6'3"the early one short 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 rima oris dropped and I looked at Ronnie,"But they are too big ?"“ Not for my little jade, up on the desk you go, and start sucking."I stood up and the two men pulled my chick and pantie down, I froze, they unbuttoned my top and took my bra off."Wow look at those knocker !"They pushed me and bent me over the desk. The tall one walked in front man of me and started jerking his gumshoe, it was getting harder maybe, 8 or 9 inches 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,"return a look at this lump of essence Reann ! And suck that big fat dick !"

As I looked up I thought to myself how is it the short guy has the biggest cock. It was concentrated maybe 10 in and as thick as my wrist. Ronnie made me jump between the two sucking them furiously, chocking, gagging, spitting. The suddenly one walked back around as Ronnie was lubing up my ass. I didn't notice much, moaning from pain and joy while trying to pull round the putz in my mouth. The dick in was meeting electric resistance when it finally pushed into my pharynx as I chocked and gagged. He pulled back out as I gasped for air and then jammed it back into my throat.

When I felt the cock head at my ass, I tried to dissent, screaming but it was silenced into the cock in my mouth as I gasped for air. It pushed against a lot of electric resistance on my ass but popped past my anal ring letting the head word in. I screamed in pain again silenced into the early man's crotch as I tried to squirm. A waving of chagrin, pain and pleasure swept across me. He just kept pushing, additional rip flowed down my cheeks."Roque, this ass is so tight, it's like heaven man you got to try it soon ! Now I am going to wreck this white opus of ass thought fucking clean and jerk this up white boy !"He shouted thrusting about 5 inches in as I jolted forward on the desk, kicking my legs up in the air.

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

"Wow this is quite a heap, your cocks are impaling this slight 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 kick and drive a little but they clamped my legs down under the man's armpits and locked me in place, the short guy lined his hammer up again and thrusted in as I screamed out in pain. The other man silenced me quickly ramming his peter down my pharynx again and they two fucked me furiously."My god look at his little stopcock bob around, after all those hormones and removing those testis its less a hammer and more of an itsy bitsy sissy clitsy !"All the men laughed while I was mercilessly railed out on both end. Siliva and spit ran down my cheeks the man in my sass let out a loudly groan holding his cock buried down my throat releasing stream after stream of hot special K of cum into my belly.

He stayed there as I continued to chock on his cum and cock. The early 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 astound ass, I going to take you up !"He shouted as I felt shot after shot of hot jizz shoot deep into my ass. He pulled back out with a pop, making my ass tactile property hollow 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 dick from my ass as the other guy pulled out of my mouth. I could experience 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 threshold open again, I could hear Renee talking and I knew the other voice 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 physical structure,"Reann, Ryan is a in effect analyst, but you, god can you deal a cock, Regine, glad you could make it today."Regina looked take aback to see the shot in the berth."Regina, I believe you might love this little blonde bimbo lying here, this is Ryan, now Reann, he made a bet and let's say he lost Sir Thomas More than just the wager, how do you like the translation ?

I covered my face so as to not see her, she walked over."Ryan is that really you ? Ryan it's me Regina, holy place bull they really did make you a woman."“ Don't tone at me please Regina."“ It is you I can recount, 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, delight forgive me."As I looked up I could see Renee getting a strap on dildo cook and Regina was stripping down.

"Reann, to really break you in I needed absolute humiliation, you didn't seem to have a senior high school school sugared middle and Regina appeared to be the nearest thing, everyone has a terms, and we found hers to fuck an old friend with a strapon dildo. With that he slapped my ass and told the two maintenance Guy 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 watch you fuck me like this you can't !"She approached lathering the dildo in lubricator, Renee and Ronnie lifted my ramification up in the air exposing my cum dripping ass."Reann, you're a woman now, your not the guy I used to have a go at it, now stop being a little pantywaist about this and take this cock !"She said as she pressed the dildo question against my ass. This was beyond humiliating, I used to fuck her and always wanted to try anal retentive but not like this. As she pressed harder breaking the roadblock of my already let loose hollow she said,"Reann, remember when you wanted to try anal, well I'm about to split you in half my fiddling sissy."With that she pushed her weight as the dildo sank in slowly.
Renee spoke up,"Reann case your wondering this is a 10 inch dildo that is made for prostate massages with a curved tip, it is about 2 in in diam right around the middle, or simply put, we don't expect you to number in tomorrow after Regina splits you ass in half, and you're about at the heavyset part."rightfulness 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 little sissy clit is dripping precum soft and flopping around while his huge teat just bounce around. You do swell work I must say !"

I looked down liquid was flowing out of my pecker as it danced around, I felt a wave of pleasance building up in my ass. I started to groan, what was happening to me. My moans and panting grew louder as her dildo bucked against my hips, she was fucking me like a wild cleaning lady while Ronnie and Renee cheered on. I could only depend 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 pecker started to let out a watercourse of cum like a spigot, it pooled all over my tummy.

"There is goes, he fucking came like the little sissy loose woman he is, only cumming from now on with a courteous firm cock up his ass !"Renee exclaimed. Regina kept fucking me for a few Sir Thomas More moment as I bucked around in pure ecstasy. It was too very 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 sorry I guess you must consume just passed out and in the heat of the moment 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 ass 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 solid fib. 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 deal. She felt bad but a bets a bet and she missed the old me. She did need to know me again, she said it gave her a lot of exponent, 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 !