I came from a Youngstown OH, my family was really poor growing up and life wasn't easy. My father moved out and left us when I was only 10 and my mother supported the kinsfolk working at a supermarket during the day and bar attention at night. Since I was really respectable at math and managed to get a scholarship to Ohio state I found a way out. I got a level in mathematics with a focus in statistics. I applied to problem all over the country and got a few honest interview 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 hedgerow investment company. I left behind Regina, we hooked up and had a lot of nifty sex but never could really set out dating with college and everything.

I was nervous but convinced at the same time about this move. I had a few rhythm of interviews with HPQ Advisors and finally I got the job as an analyst. Starting remuneration was $ 65,000 with operation based bonus. My first week Reginold, went by Reggie told me the bonuses aren't the lonesome way of getting duplicate income, Ronnie the proprietor likes making picayune bet here or there with staff.
NYC was not bad minus one thing, the cost, I had found a two-bedroom apt that one bed room was for snag but it was $ 1,300 per month and I had student loan of $ 800 per month. Long minute, eating out and socializing left me no way 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 faulting to healthcare sector, which has worked out quite nicely."“ Yes, sir that was me."“ Well why don't you meet me for tiffin at Bobby burn 1 pm sharp."

Wow this is so shake, I get to eat with Ronnie, he was loaded. We sat down and I listened to him and two other business associate degree talk about various topics, nigh of which made my stomach good turn since it was all about how to easily exact advantage of the poor in the land etc."So, you like healthcare right now, which parentage in fussy boy ?"“ Well sir Valeantz looks like a decent buy right now it is trading at 228 but my figuring show based on its momentum it could easily go to 300."“ Is that compensate boy, how about we bet $ 20,000 on that he said ?"I choked on my drinkable and everyone burst out laughing at the table myself included.

"Boy let me paraphrase that, if it hits 300 per share you get $ 20K, if it hits 100 per share you stop dressing as a man and depart dressing like a woman in the office."He had a menacing look on his face, the other two gentlemen were tranquillize and looked intimated. I reached out and shake on it. It was worth the jeopardy for me plus it was trading above 200 it would need a 50 % plus deplume back to hit his figure. Come by my bureau when we get back and we will work out the particular.
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 place. I sat down in front of his desk,"My boy, we need to act upon out these contingent, let me ask, I looked over your sketch, where you are from etc, how much do you owe in pupil loans and how about that as the bet ?"“ I owe $ 80,000, you'd be leave to bet that much on one stock ?"“ Absolutely boy, how a great deal do you require on top of that,"“ How about $ 100,000 plus the $ 80,000 if you want me to take the air around like a woman ?"“ Sounds like a design, let's do this, $ 500,000, if you win you get $ 500K, if you lose, you become my hard worker for intimate favors with me and my friends, you will look like a cleaning woman, throw up, little surgery here or there, office staff slut type flavor, we lost heather last month and she was the part roll in the hay toy, so I am looking for another one and you fit the build."“ Are you out of your mind !"I exclaimed,"$ 1 million in that showcase, you would be able to help your phratry back home and what are the chances the line of descent drop to 100, in fact make it 90 and you have to hit 275 ? Think about how easily you can create your life-time great ! Deal or no pot no thinking this one over end of story."I took a deep intimation,"plenty !"we shook hands, his right-hand man Robert spoke up,"ok boys, we have a bet here for a declamatory sum of money, I will draft up the legal 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 wrong as I looked flushed. I explained to him the stake. He explained to me, that Ronnie loved to constitute those wager, he had won a similar bet and make $ 100K on the deal. I felt much better, 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 little but there was all this news about outrage going on etc. future affair I know my tenderness sank and my lump 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 base on balls of shame, waiting inside Ronnies place were a few women with vesture rack 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, considerably way to get word is to get you ball kicked in. In your typesetter's case, literally, now Renee make him look pretty,"she looked at me,"Come with us to the woman's storage locker room in the gym downstairs."My heart was racing, these three beautiful women walked me to the char's locker."landing strip down, let's see what we are working with."I turned rhythm red, I am 5'9"and weight 150 lbs with a lanky physical structure soma."Step in the shower, and knock off your all your hair's-breadth but your head, make sure you get your asshole too,"They handed me shaving cream, organic structure wash and shampoo. I took the cascade and shaved everything and just stood there, my god what have I done. The cleaning woman asked me to overspread my face, I did exposing my rosebud,"shuffle sure no hairsbreadth 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 war paint 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 business office I went in through the rear into Ronnie's office."Ahh there is my profits, let's get you into a nice reserve office attire."He made me mock up different clothes off the rack settling on 1.5 inch heels, a Joseph Black dress with a tight tweed button down. He had the women leave the function and he sat on the couch."clip 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 seduce sure you are well taken concern of, just get ready to chug a lot of stopcock"

I looked into the mirror and started to cry, I went from a pretty good looking guy, to a blond bimbo in one day. With that he unzipped his drawers 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 got become rich, it was worth the bet for you and this is deserving it for me. Now if you don't book up your end, go back home and start working at the supermarket where your mom is because osculation any other career good bye. I can easily end you and your class from any pattern beingness. Now open up and elucidate you tears !"

I wiped away my rent and approached his genitalia, I looked down at his flaccid penis maybe about 5 inches slightly thick."That a girl, he said, now suck this like the slut you are."As he said this he grabbed the cover of my top dog and lined it up with his dick."Relax girl, slow your breathing, my cock will grow inside your mouth but I will slowly bob your head up and down nicely."I pushed my spit forward toward the tip and licked it. To my surprise, it didn't taste bad, it was rather salty. I did my best picture on what I say from the pornography I've watched and took the foreland in fully. He moaned in acceptance and I just bobbed up and down slowly working in as many column inch as I could.

"Look up at me, I have to see you with my turncock buried in your pretty short oral cavity, you realize there is no way out but to do a thoroughly job."I stared up at him, tears still building, bobbing up and down as I felt his tool slowly growing inside my backtalk.

I just wanted this to end, I bobbed furiously, my manus caressed his balls, meretricious slurping phone came out of my mouth. He put his hand behind my foreland and I felt him push down harder, his tool must feature been about 6 - 6.5 inches now and maybe 1.5 inches encompassing. I might stimulate been down 4 column inch when I felt his tip jibe against the spine of my throat causing me to gag. He had shoved my head down and with both hands behind my top dog held me tight. I continued to suffocate, tears streamed down and spittle flowed from his mouth. He buried my face into his pubic bone and release quickly allowing me an opportunity to breath as I gasped for air. While trying to overtake my breath he just kept pushing down my head as I dodged his cock, rubbed my spittle all over my face.
"Isn't life funny, one day you're some popular college kid banging girlfriend the adjacent you've got your headspring buried in some older man's crotch while you choke on his pecker and the day after that two gallant are using you like a Chinese finger trap ! Now take that dick again and sallow my cum before I shove it in your ass !"With that I realigned my mouth over his cock and his thrusted it into my mouth. Gagging racket followed as I fought to survive this assault on my sassing. He furiously fucked my human face for about 5 bit before burying my case back down and pumping heaps of salty slimy cum into my belly. As he let go I choked and gasped for air. He pulled his pant 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 less of a working girl when you're done. Here is your suitcase with you outfit for tomorrow. Please see Dr. Regario adjacent calendar month on the 15th at 10 am. Here is his scorecard. He has a trivial employment to do on your goose egg major just a few point of study. In the interim, you are to learn these oral contraceptive pill, they will make anal and former activities hurt less. Lastly here is a bag with sex toy's keister plugs from 2 inches to 6 in that will unfold your ass for anal sex, please work up to these"Ronnie stood up,"Now head home kid, it's getting late, get a unspoilt night's rest to let this root in."

For the adjacent month, I came into workplace dressed as a charwoman, Reggie just nodded with a shit happens around here kind of aspect. No one seemed shocked at all. Reggie mentioned that Lapplander shit happened to heather before she left. My roomie didn't say much, a bit confused at low but I explained the deal and he said he would have taken the deal too. I was really moody and upset, but Ronnie didn't do anything else that was intimate. I gained a crew of weight probably from eating and being depressed. I noticed on my calendar the Dr.'s appointment was for tomorrow.

The next morning I took my 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 cluster of paperwork and consent word form. I was called into his spot. He reassured me everything is reversible, per Ronnie's society there was a little work he wanted but nothing John R. Major. I didn't even want to sleep with what he had in creative thinker. He laid me on the board and gave me some gas as I slowly fell asleep.
I awoke in an awful amount of money 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 expression damage, my chest hurt, my ass scathe. As I looked down there was something on my chest blocking some of my view."Ohhh my god, what the shtup did you do !"I yelled out. They gave me breast implants ! What the fuck !"I'm going to fucking stamp out you !"I screamed out, quickly security came into the room and held me down. Dr. Regario walked forward."Ryan, listen here, I have monastic order paid for from Ronnie your boss, along with several documents signed by you as division of a bet you two made, he does this betray all the metre. He ordered, butt implants, lip injections, brow lifts, hairsbreadth implants, lazer fuzz removal, ass bleaching and cleaning, calfskin implants, breast implants, emasculation and liposuction, most of the fat from your mid-section and weapons system in now in your ass. I do have got to say you came out pretty damn hot though !"

My affection sank and I passed out. I awoke again."That happened a lot around here, perfectly convention. Those hormones you were taking really helped in making your bosom double ds by the way, they gave us just enough tissue around the edges."I thought I was dreaming earlier until he made that scuttlebutt. I just started to cry."MD 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 glob you just receive what Ronnie call's, a Milquetoast clitoris left that can't produce sperm. And all these written document here protect me, you should say more carefully when betting with Ronnie."

Oh, my god, they cut off my balls, I couldn't mental process this right now, strangely it didn't hurt. My will for getting upset was gone, I had no feeling.
Renee was waiting in the lobby for me as she helped me gather my property and escorted me to her car. She drove me home,"So is some unrestrained to see how their beautiful new torso looks."I said zip just sat there crying."Ryan or Reann, take the next calendar month off for convalescence, Ronnie has deposited $ 50,000 into your account to soothe you. Take it easy, we will send off food over and everything to ease your recuperation. These DVD's are for you to watch and train that ass by the way."My roommate was shocked, and just didn't say a word as I walked in with bandage and the obvious translation.
About a month later I got cook for work, I really did look hot, Brobdingnagian mammilla, fat ass, big backtalk, low shank everything. My pecker 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 butt end plugs. For some rationality the dildos really made me cum and regular porn did cypher, probably the pill.

When I arrived back at body of work I got a lot of looking. 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 as everyone was leaving for the day I walked into Ronnie's place."My god you look beautiful ! Let's run those lips out."He said as he undid his pants. I walked over and got on my knees, I took his stopcock in my mouthpiece and bobbed up and down slurping this fourth dimension taking it all no problem."person has been practicing I see. God those lips make it so much better"because of those lips drool was sliding out around his peter and running down my face.
Right after that I heard the door open up and the cleaning crew came in, I immediately stopped and pulled off mortified. Ronnie grabbed my header,"Don't plosive speech sound dear ! Hey you two stay a spell, isn't she pretty, this is Reann, commemorate the young guy that works here this is him after surgery."He just restrain pumping and a few moments later he pushed my read/write head all the way in and shoot a onus deep down my throat. 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 offset cock, how about you two help me separate him in. His ass has to be tight as hellhole, consider it an ahead of time Dec 25 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 shit Ronnie, this was that young new guy, my god you gave him the hottest set of tits an ass I've ever seen on a chick, let alone a buster. I'm not gay, but fuck that ass looks juicy as nether region and those mouth 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 but one in the room that will make one up her slit !"

I looked at them one was improbable maybe 6'3"the other one shortstop and fat maybe 5'6"both Spanish and form of grimy looking. They both started unzipping their pants when two fat turncock plopped out. My mouth dropped and I looked at Ronnie,"But they are too big ?"“ Not for my footling loose woman, 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 looking at at those bosom !"They pushed me and crouch me over the desk. The marvellous one walked in front man of me and started jerking his dick, it was getting harder maybe, 8 or 9 inch and really fat. He pushed it into my mouth, 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 aspect at this lump of meat Reann ! And suck that big fat cock !"

As I looked up I thought to myself how is it the unforesightful guy has the biggest cock. It was hard maybe 10 column inch and as midst as my wrist joint. Ronnie made me tack between the two sucking them furiously, chocking, gagging, spitting. The abruptly one walked back around as Ronnie was lubing up my ass. I didn't notice much, moaning from pain in the ass and pleasure while trying to pull round the pecker in my oral cavity. The prick in was meeting electrical 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 turncock head at my ass, I tried to protest, screaming but it was silenced into the cock in my back talk as I gasped for air. It pushed against a lot of resistance on my ass but popped past my anal mob letting the head in. I screamed in botheration again silenced into the former man's crotch as I tried to squirm. A wafture of humiliation, hurting and pleasure swept across me. He just kept pushing, extra tears flowed down my brass."Roque, this ass is so tight, it's like Eden man you got to try it soon ! Now I am going to wrack this Edward White art object 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 stage up in the air.

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

"Wow this is quite a view, your cocks are impaling this little girl on both ends like an accordion ! Why don't you lift him up ?"With that I tried to protest but cypher helped, they lifted me off the desk and flipped me upside down rotating me in midair, I tried to kick and advertise a piddling but they clamped my legs down under the man's axillary cavity and locked me in plaza, the shortsighted guy lined his cock up again and thrusted in as I screamed out in botheration. The other man silenced me quickly ramming his pecker down my throat again and they two fucked me furiously."My god expression at his petty peter bob around, after all those hormones and removing those globe its LE a pecker and more of an itsy bitsy sissy clitsy !"All the men laughed while I was mercilessly railed out on both last. Siliva and spit ran down my cheeks the man in my mouth let out a flash moan holding his cock buried down my throat releasing stream after stream of hot jet of cum into my belly.

He stayed there as I continued to chock on his cum and cock. 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 amazing ass, I going to fill 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 flavor 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 early guy pulled out of my mouth. I could feel a stream of cum trickeling out of my ass. I collapsed on the desk after they let me down, exhausted, ashamed and humiliated as I lost my anal virginity.

I heard the door open again, I could get a line Renee talking and I knew the former 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 limp body,"Reann, Ryan is a sound analyst, but you, god can you take a rooster, Regine, glad you could stool it today."Regina looked shocked to see the scene in the office."Regina, I believe you might know this footling 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 nerve so as to not see her, she walked over."Ryan is that really you ? Ryan it's me Regina, sanctum crap they really did clear you a woman."“ Don't expression at me please Regina."“ It is you I can tell, wow they did some 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 strap on dildo make and Regina was stripping down.

"Reann, to really break you in I needed absolute humiliation, you didn't seem to have a gamey school Sweet philia and Regina appeared to be the closest thing, everyone has a monetary value, and we found hers to fuck an old friend with a strapon dildo. With that he slapped my ass and told the two criminal maintenance guys to get out.
Renee was helping Regina get on the large strapon. I pleaded and cried,"Regina please don't do this I can't watch you fuck me like this you can't !"She approached lathering the dildo in lube, Renee and Ronnie lifted my stage up in the air exposing my cum dripping ass."Reann, you're a woman now, your not the guy I used to do it, now stop being a little Milquetoast about this and take this shaft !"She said as she pressed the dildo read/write head 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 trap she said,"Reann, remember when you wanted to try anal, well I'm about to split up you in half my little sissy."With that she pushed her exercising weight as the dildo sank in slowly.
Renee spoke up,"Reann incase your wondering this is a 10 column inch dildo that is made for prostate massages with a swerve tip, it is about 2 inch in diam right wing around the midriff, 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 thickest 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 pantywaist I am."Ronnie, expect what you did, his little sissy clit is dripping precum soft and flopping around while his huge boob just bounce around. You do great employment I must say !"

I looked down liquidness 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 moan and panting grew louder as her dildo bucked against my articulatio coxae, she was fucking me like a wild woman while Ronnie and Renee cheered on. I could only take care up at the faces as they stared in a trance at the Brobdingnagian dildo ripping my ass up."Oh gawd, oh gawd,"I yelped out as I felt like I was about to flare when all of a sudden my cock started to let out a stream of cum like a spigot, it pooled all over my venter.

"There is goes, he fucking came like the little Milquetoast loose woman he is, only cumming from now on with a nice firm turncock up his ass !"Renee exclaimed. Regina kept fucking me for a few More minutes 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 couch now.

"Reann, I am sorry I guess you must have 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 roll in the hay out, subscribe to the day off tomorrow, you've done enough work today."

Regina and I went out to dinner, I was ashamed and told her the whole story. She explained how they called her out of the Amytal and offer $ 100,000 to roll in the hay you and an additional $ 50,000 if I really humiliated you. I didn't incrimination her for taking the raft. She felt bad but a stakes a bet and she missed the old me. She did want to bed me again, she said it gave her a lot of major power, she also wanted to see a guy rail me out, perhaps my roommate, speculation I know what I am doing tonight at my flat.

The end for now !