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 family working at a supermarket during the day and bar aid at night. Since I was really good at math and managed to get a scholarship to Ohio State I found a way out. I got a arcdegree in math with a focus in statistics. I applied to task all over the country and got a few estimable interviews lined up in NYC. With the little money I had from my of late night working at a bar I flew out to NYC and interviewed with some small hedge investment company. 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 spooky but confident at the same meter about this move. I had a few rung of consultation with HPQ adviser and finally I got the job as an analyst. Starting salary was $ 65,000 with carrying out based bonus. My commencement hebdomad Reginold, went by Reggie told me the bonus aren't the only way of getting extra income, Ronnie the possessor likes making little wager here or there with staff.
NYC was great minus one affair, the cost, I had found a two-bedroom apt that one bed way was for snag but it was $ 1,300 per calendar 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 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 Holocene epoch shift to healthcare sector, which has worked out quite nicely."“ Yes, sir that was me."“ Well why don't you meet me for lunch at Bobby tangent 1 pm sharp."

Wow this is so exciting, I get to eat with Ronnie, he was loaded. We sat down and I listened to him and two other business associates talk about various topics, most of which made my stomach bout since it was all about how to easily take advantage of the misfortunate in the state etc."So, you like healthcare right now, which stock in fussy boy ?"“ fountainhead sir Valeantz looks like a decent buy right now it is trading at 228 but my calculations show based on its impulse it could easily go to 300."“ Is that proper boy, how about we bet $ 20,000 on that he said ?"I choked on my drink and everyone burst out laughing at the board myself included.

"Boy let me paraphrase that, if it hits 300 per part you get $ 20K, if it hits 100 per parcel you stop dressing as a man and start dressing like a woman in the office."He had a black look on his case, the other two gentlemen were quiet and looked intimated. I reached out and stir on it. It was worth the jeopardy for me plus it was trading above 200 it would need a 50 % plus force back to hit his number. Come by my authority when we get back and we will form out the specific.
I had a little bit of a bad feeling but still confident 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 work out these details, let me ask, I looked over your sketch, where you are from etc, how much do you owe in educatee loan and how about that as the wager ?"“ I owe $ 80,000, you'd be will to bet that much on one stock ?"“ Absolutely boy, how much do you require on top of that,"“ How about $ 100,000 plus the $ 80,000 if you want me to walk around like a woman ?"“ audio like a design, 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 char, make up, little surgery here or there, part slut type flavor, we lost Heather final calendar month and she was the billet 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 causa, you would be able to help your family back rest home and what are the chances the strain drops to 100, in fact make it 90 and you have to hit 275 ? Think about how easily you can make your life-time large ! lot or no softwood no thinking this one over end of story."I took a deeply breath,"Deal !"we shook manpower, his right-hand man Robert spoke up,"ok boys, we have a bet here for a expectant sum of money, I will outline up the effectual paperwork and have you both sign tomorrow bonny enough ?"We both nodded.

My heart was racing as I walked back to my desk, Reggie asked me what was amiss as I looked flushed. I explained to him the wager. He explained to me, that Ronnie loved to progress to those bets, he had won a similar bet and make $ 100K on the deal. I felt much dependable, 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 dirt going on etc. Next thing I know my tenderness sank and my balls pulled up, 110, 100, then it happened it closed at 75. Henry M. Robert approached me, Ronnie would like to see you in his office.

I took my walk of shame, waiting inside Ronnies office were a few women with habiliment 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, best way to learn is to get you balls kicked in. In your case, literally, now Renee make him look pretty,"she looked at me,"seed with us to the womanhood's footlocker room in the gym downstairs."My heart was racing, these three beautiful women walked me to the women's footlocker."cartoon 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."Step in the shower, and knock off your all your hair but your heading, make sure you get your asshole too,"They handed me shaving cream, dead body backwash and shampoo. I took the cascade and shaved everything and just stood there, my god what have I done. The woman asked me to circularize my cheeks, I did exposing my rosebud,"Make for sure no tomentum 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 back into Ronnie's office."Ahh there is my winnings, let's get you into a nice conquer office attire."He made me simulate unlike clothes off the rack settling on 1.5 inch heels, a black dress with a blotto Elwyn Brooks White button down. He had the women leave the office and he sat on the couch."clock time to start paying up boy, hope you like tool because you're going to give birth a lot of hawkshaw in your life going forward. I will wee sure you are well taken care of, just get ready to chug a lot of cock"

I looked into the mirror and started to cry, I went from a pretty safe 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 people, 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 start working at the supermarket where your mom is because kiss any early career good bye. I can easily end you and your phratry from any normal world. Now open up and realize you tears !"

I wiped away my binge and approached his crotch, I looked down at his flabby penis maybe about 5 inches slightly thick."That a fille, he said, now suck this like the jade you are."As he said this he grabbed the dorsum of my head word and lined it up with his dick."Relax young woman, slow your breathing, my stopcock will mature inside your mouth but I will slowly bob your fountainhead up and down nicely."I pushed my spit forward toward the tip and licked it. To my surprise, it didn't penchant 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 inches as I could.

"tone up at me, I have to see you with my rooster buried in your somewhat short mouth, you realize there is no way out but to do a good job."I stared up at him, rent still building, bobbing up and down as I felt his cock slowly growing inside my sassing.

I just wanted this to end, I bobbed furiously, my manpower caressed his balls, loud slurping strait came out of my mouth. He put his manus behind my head and I felt him push down harder, his dick must have been about 6 - 6.5 inches now and maybe 1.5 in wide. I might have been down 4 in when I felt his tip shot against the spine of my throat causing me to gag. He had shoved my head down and with both hand behind my head held me squiffy. I continued to choke, tears streamed down and spittle flowed from his mouth. He buried my face into his pubes and handout quickly allowing me an chance to breath as I gasped for air. While trying to enamour my hint he just kept pushing down my head as I dodged his hammer, rubbed my tongue all over my nerve.
"Isn't biography funny, one day you're some pop college kid banging miss the next you've got your foreland buried in some former man's genitals while you choke on his cock and the day after that two dude are using you like a Chinese digit bunker ! Now take that hammer again and sallow my cum before I shove it in your ass !"With that I realigned my mouth over his rooster and his thrusted it into my sassing. Gagging randomness followed as I fought to live on this assault on my mouth. He furiously fucked my face for about 5 minutes before burying my face back down and pumping loads of salty slimy cum into my belly. As he let go I choked and gasped for air. He pulled his drawers 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 poor baby, well work on that gag reflex so you look like less of a whore when you're done. Here is your suitcase with you outfit for tomorrow. Please see Dr. Regario adjacent month on the 15th at 10 am. Here is his placard. He has a little employment to do on your nothing John Roy Major just a few detail of workplace. In the meantime, you are to learn these oral contraceptive, they will shit anal and former activities hurt less. Lastly here is a bag with sex toy's cigaret ballyhoo from 2 inches to 6 inches that will stretch your ass for anal sex, please workplace up to these"Ronnie stood up,"Now head home kid, it's getting late, get a good Nox's rest to let this adjudicate in."

For the next calendar month, I came into work dressed as a woman, Reggie just nodded with a dump happens around here kind of look. No one seemed shocked at all. Reggie mentioned that same motherfucker happened to heather before she left. My roommate didn't say much, a bit confused at commencement but I explained the deal and he said he would experience taken the deal too. I was really moody and swage, but Ronnie didn't do anything else that was intimate. I gained a bunch of weight probably from eating and being depressed. I noticed on my calendar the Doctor's appointment was for tomorrow.

The future daybreak 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 clustering of paperwork and consent cast. I was called into his office. He reassured me everything is two-sided, per Ronnie's order there was a little work he wanted but zilch major. I didn't even want to know what he had in judgment. He laid me on the table and gave me some gas as I slowly fell asleep.
I awoke in an awful amount of pain in the neck, dazed and confused as to what just happened."Ah our patient role is finally coming too."Dr. Regario exclaimed. I slowly tried to sit up, my face damage, my chest hurt, my ass hurt. As I looked down there was something on my chest of drawers blocking some of my view."Ohhh my god, what the fuck did you do !"I yelled out. They gave me bosom implants ! What the screwing !"I'm going to fucking kill you !"I screamed out, quickly security came into the way and held me down. Dr. Regario walked forward."Ryan, listen here, I have society paid for from Ronnie your chief, along with several text file signed by you as part of a bet you two made, he does this snitch all the time. He ordered, coffin nail implants, lip shot, eyebrow elevation, hair implants, lazer hair removal, ass bleaching and cleansing, calf implants, breast implants, emasculation and liposuction, nearly of the fat from your mid-section and arms in now in your ass. I do let to say you came out pretty damn hot though !"

My ticker sank and I passed out. I awoke again."That happened a lot around here, perfectly pattern. Those endocrine you were taking really helped in making your tits twofold ds by the way, they gave us just enough tissue around the edges."I thought I was dreaming earlier until he made that commentary. I just started to cry."Doctor you can't leave me like this, I am a man, I can't go home like this."The Dr looked at me"Well the key discussion is, was, not, am, you were a man, after we cut off your clod you just possess what Ronnie call's, a epicene button left that can't produce sperm. And all these papers here protect me, you should read more carefully when betting with Ronnie."

Oh, my god, they cut off my clump, I couldn't process this rightfield now, strangely it didn't detriment. My will for getting overthrow was gone, I had no look.
Renee was waiting in the lobby for me as she helped me gather my belongings and escorted me to her car. She drove me rest home,"So is some shake to see how their beautiful new body looks."I said nil just sat there crying."Ryan or Reann, take the next month off for recovery, Ronnie has deposited $ 50,000 into your account to solace you. Take it easy, we will send food over and everything to ease your convalescence. These DVD's are for you to take in and aim that ass by the way."My roommate was shocked, and just didn't say a word as I walked in with bandages and the obvious translation.
About a month later I got gear up for work, I really did look hot, huge nipple, fat ass, big brim, small-scale shank everything. My cock used to be around 6 inches now barely 5 and skinny when laborious. The DVD was fully of sissy sex and hypno, I used my dildos and can plug. For some reason the dildos really made me cum and steady porn did naught, probably the pills.

When I arrived back at work I got a lot of looks. 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 office."My god you look beautiful ! Let's test those lips out."He said as he undid his pants. I walked over and got on my knee joint, I took his cock in my oral cavity and bobbed up and down slurping this time taking it all no job."somebody has been practicing I see. God those backtalk make it so much better"because of those brim drool was sliding out around his stopcock and running down my face.
Right after that I heard the door receptive and the cleansing crew came in, I immediately stopped and pulled off necrose. Ronnie grabbed my straits,"Don't halt honey ! Hey you two stay a piece, isn't she pretty, this is Reann, remember the Danton True Young guy that works here this is him after surgery."He just go on pumping and a few bit later he pushed my nous all the way in and pip a load deep down my pharynx. I whipped my boldness 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 peter, how about you two avail me break him in. His ass has to be tight as nether region, conceive it an early Yule present."I could get wind them walking over as Ronnie let up on my foreland.

The two men smiled, with a Spanish accent they said,"Holy shit Ronnie, this was that immature new guy, my god you gave him the blistering set of tits an ass I've ever seen on a skirt, let alone a dude. I'm not gay, but fuck that ass looks juicy as the pits and those sassing were built for sucking cock."Ronnie looked to them,"don't worry it's only gay when there is a cock in your ass, Reann is the only one in the room that will feature one up her pussy !"

I looked at them one was marvelous maybe 6'3"the other one scant and fat maybe 5'6"both Spanish and kind of grimy looking. They both started unzipping their pants when two fat cocks plopped out. My mouth dropped and I looked at Ronnie,"But they are too big ?"“ Not for my footling jade, up on the desk you go, and get down sucking."I stood up and the two men pulled my bird and panties down, I froze, they unbuttoned my top and took my bra off."Wow flavor at those tits !"They pushed me and bent me over the desk. The tall one walked in front of me and started jerking his dick, it was getting grueling maybe, 8 or 9 inches and really fat. He pushed it into my mouth, I gagged and slurped. The early one started eating out my ass as I moaned. The guy behind stopped licking and walked around with Ronnie,"proceeds a look at this hunk of sum Reann ! And suck that big fat cock !"

As I looked up I thought to myself how is it the short guy has the bounteous hammer. It was intemperately maybe 10 inches and as thick as my radiocarpal joint. 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 annoyance and pleasure while trying to survive the cock in my mouth. The dick in was meeting immunity 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 straits at my ass, I tried to protest, screaming but it was silenced into the tool in my sassing as I gasped for air. It pushed against a lot of electrical resistance on my ass but popped past my anal ring letting the header in. I screamed in pain again silenced into the other man's crotch as I tried to squirm. A wave of humiliation, pain and pleasure swept across me. He just kept pushing, additional tears 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 wrack this Elwyn Brooks White 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 leg up in the air.

It felt like my insides couldn't accommodate any more when another column inch when in. My insides felt like they were being ripped apart. My side plowed into the former man's putz showing no escape 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 clod slapped against my little cock that was just dangling there.

"Wow this is quite a pile, 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 nothing 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 legs down under the man's axilla and locked me in place, the unforesightful guy lined his peter up again and thrusted in as I screamed out in pain. The other man silenced me quickly ramming his rooster down my pharynx again and they two fucked me furiously."My god flavour at his piffling cock bob around, after all those endocrine and removing those orb its less a putz and more of an itsy bitsy sissy clitsy !"All the men laughed while I was mercilessly railed out on both ends. Siliva and tongue ran down my buttock the man in my sass let out a loud moan holding his cock buried down my throat releasing stream after watercourse of hot spurt 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 waistline 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 fulfill you up !"He shouted as I felt pellet after shot of hot jizz shoot deep into my ass. He pulled back out with a pop, making my ass smell 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 cock from my ass as the other guy pulled out of my rima oris. I could find a stream of cum trickeling out of my ass. I collapsed on the desk after they let me down, tire, ashamed and humiliated as I lost my anal virginity.

I heard the door open again, I could discover Renee talking and I knew the other vocalization 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 hitch soundbox,"Reann, Ryan is a good analyst, but you, god can you call for a shaft, Regine, gladiolus you could reach it today."Regina looked shock to see the scene in the office."Regina, I believe you might experience this little blonde bimbo lying here, this is Ryan, now Reann, he made a bet and let's say he lost to a greater extent than just the wager, how do you like the transmutation ?

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

"Reann, to really erupt you in I needed sheer mortification, you didn't seem to give a high school sweet sum and Regina appeared to be the closelipped thing, everyone has a terms, and we found hers to bed an old protagonist with a strapon dildo. With that he slapped my ass and told the two alimony guys to get out.
Renee was helping Regina get on the boastfully strapon. I pleaded and cried,"Regina please don't do this I can't sentry you fuck me like this you can't !"She approached lathering the dildo in lubricant, 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 hump, now stop being a little pansy about this and take this cock !"She said as she pressed the dildo pass against my ass. This was beyond humiliating, I used to get it on her and always wanted to try anal but not like this. As she pressed harder breaking the barrier of my already loose muddle she said,"Reann, think of when you wanted to try anal, well I'm about to split you in half my lilliputian sissy."With that she pushed her weighting 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 veer tip, it is about 2 in in diameter right around the middle, or simply put, we don't expect you to come in tomorrow after Regina splits you ass in half, and you're about at the thickest part."Right 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, await what you did, his slight cissy clitoris is dripping precum soft and flopping around while his huge tits just bounce around. You do dandy work I must say !"

I looked down liquid was flowing out of my cock as it danced around, I felt a wave of delight building up in my ass. I started to groan, what was happening to me. My moan and panting grew louder as her dildo bucked against my hip, 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 immense dildo ripping my ass up."Oh gawd, oh gawd,"I yelped out as I felt like I was about to extravasate when all of a sudden my cock started to let out a flow of cum like a spigot, it pooled all over my stomach.

"There is goes, he fucking came like the little cissy slattern he is, only cumming from now on with a gracious firm peter 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 great deal I collapsed as she kept fucking me. I finally came too as they were all dressed and I was still naked on the lounge now.

"Reann, I am sorry I guess you must ingest just passed out and in the heat of the moment we didn't observation. 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 screw out, take the day off tomorrow, you've done adequate oeuvre 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 amobarbital sodium and offer $ 100,000 to jazz you and an extra $ 50,000 if I really humiliated you. I didn't blame her for taking the hatful. She felt bad but a bets a bet and she missed the old me. She did need to have sex me again, she said it gave her a lot of top executive, she also wanted to see a guy rail me out, perhaps my roommate, supposition I know what I am doing tonight at my apartment.

The end for now !