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 female parent supported the family working at a supermarket during the day and bar tending at night. Since I was really commodity at math and managed to get a encyclopaedism to Ohio State I found a way out. I got a degree in mathematics with a nidus in statistic. I applied to business all over the country and got a few serious interview lined up in NYC. With the fiddling money I had from my of late night working at a bar I flew out to NYC and interviewed with some humble hedge funds. I left behind Regina, we hooked up and had a lot of smashing sex but never could really start dating with college and everything.

I was nervous but positive at the same time about this move. I had a few one shot of consultation with HPQ advisor and finally I got the job as an analyst. Starting salary was $ 65,000 with carrying out based bonus. My first week Reginold, went by Reggie told me the bonuses aren't the alone way of getting special income, Ronnie the owner likes making piddling bets here or there with staff.
NYC was great minus one thing, the cost, I had found a two-bedroom apt that one bed elbow room was for rip but it was $ 1,300 per calendar month and I had scholar loanword of $ 800 per calendar month. Long minute, eating out and socializing left me no way to spare from my cash flow.

I was in the can 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 Holocene epoch duty period to healthcare sphere, which has worked out quite nicely."“ Yes, sir that was me."“ well why don't you meet me for tiffin at Bobby Tans 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 line of work associate talk about versatile topics, most of which made my tummy turn since it was all about how to easily take advantage of the miserable in the country etc."So, you like healthcare right now, which parentage in particular boy ?"“ Well sir Valeantz looks like a decent buy right now it is trading at 228 but my deliberation show based on its momentum it could easily go to 300."“ Is that flop boy, how about we bet $ 20,000 on that he said ?"I choked on my drink and everyone outburst out laughing at the table myself included.

"Boy let me rephrase that, if it hits 300 per share you get $ 20K, if it hits 100 per plowshare you stop dressing as a man and start dressing like a woman in the office."He had a sinister look on his font, the former two gentlemen were quiet and looked intimated. I reached out and shake off on it. It was Charles Frederick Worth the risk for me plus it was trading above 200 it would need a 50 % plus draw back to hit his number. Come by my position when we get back and we will work out the specific.
I had a little bit of a bad feeling but still positive I could get that $ 20k to pay off my student loanword as I walked into his billet. I sat down in movement of his desk,"My boy, we need to work out these details, let me ask, I looked over your CV, where you are from etc, how much do you owe in student loan and how about that as the bet ?"“ I owe $ 80,000, you'd be willing 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 fair sex ?"“ Sounds like a plan, let's do this, $ 500,000, if you win you get $ 500K, if you lose, you become my slave for sexual favors with me and my friends, you will look like a cleaning lady, make up, little surgery here or there, agency slut type look, we lost Heather last month and she was the office ass toy, so I am looking for another one and you fit the build."“ Are you out of your mind !"I exclaimed,"$ 1 million in that case, you would be able-bodied to help your family back home base and what are the chances the stock drops to 100, in fact make it 90 and you have to hit 275 ? consider about how easily you can build your life story great ! muckle or no deal no thinking this one over end of story."I took a deep breathing time,"passel !"we shook script, his right-hand man Henry M. Robert spoke up,"ok boys, we have a bet here for a large sum of money, I will draft up the effectual paperwork and have you both signboard tomorrow reasonable enough ?"We both nodded.

My kernel was racing as I walked back to my desk, Reggie asked me what was wrong as I looked flushed. I explained to him the wager. He explained to me, that Ronnie loved to pee-pee those bet, he had won a similar bet and make $ 100K on the mickle. I felt much dear, I closely tracked the stock 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 little but there was all this tidings about scandal going on etc. Next thing I know my meat sank and my balls 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 walk of life of shame, waiting inside Ronnies office were a few char 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 larn is to get you ball kicked in. In your casing, 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 heart was racing, these three beautiful cleaning lady walked me to the women's storage locker."striptease down, let's see what we are working with."I turned metre red, I am 5'9"and weight 150 lbs with a lanky body anatomy."Step in the shower, and shave your all your hair but your head, make sure you get your shit too,"They handed me shaving ointment, soundbox washables and shampoo. I took the shower and shaved everything and just stood there, my god what have I done. The fair sex asked me to propagate my cheeks, I did exposing my rosebud,"shuffle for sure no fuzz 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 constitution and put a wig on. I had a robe on and they gave me a lacey flip-flop and bra. We went back up to the office I went in through the back into Ronnie's billet."Ahh there is my winnings, let's get you into a nice appropriate position attire."He made me model unlike clothes off the wrack settling on 1.5 in heel, a black dress with a tight white push down. He had the women leave the office and he sat on the sofa."Time to start paying up boy, hope you like cock because you're going to have a lot of hawkshaw in your sprightliness going forward. I will make certainly you are well taken precaution of, just get ready to chug a lot of cock"

I looked into the mirror and started to cry, I went from a pretty practiced looking guy, to a blond bimbo in one day. With that he unzipped his pants and pulled out his extremity. I protested as I cried,"Ryan, no one likes a blow job where the char is crying before they even gag. Now you made this bet and could possess 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 home and start working at the supermarket where your mom is because osculation any early vocation good bye. I can easily end you and your family from any normal macrocosm. Now open up and readable you tears !"

I wiped away my tears and approached his crotch, I looked down at his flaccid member maybe about 5 column inch slightly thick."That a missy, he said, now suck this like the trollop you are."As he said this he grabbed the rachis of my head and lined it up with his tool."Relax daughter, slow your ventilation, my cock will grow 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 surprisal, 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 psyche in fully. He moaned in credence 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 jolly short mouth, you realize there is no way out but to do a dear job."I stared up at him, tears still building, bobbing up and down as I felt his turncock slowly growing inside my backtalk.

I just wanted this to end, I bobbed furiously, my hands caressed his bollock, loud slurping sounds came out of my mouth. He put his hand behind my head and I felt him push down harder, his dick must get been about 6 - 6.5 inches now and maybe 1.5 inches wide. I might have been down 4 inches when I felt his tip slam against the back of my pharynx causing me to gag. He had shoved my school principal down and with both hands behind my head held me wet. I continued to exit, rip streamed down and spittle flowed from his mouthpiece. He buried my expression into his pubic region and sack quickly allowing me an opportunity to breath as I gasped for air. While trying to beguile my breathing space he just kept pushing down my header as I dodged his cock, rubbed my spit all over my facial expression.
"Isn't life history funny, one day you're some popular college kid banging girls the following you've got your head buried in some older man's crotch while you choke on his cock and the day after that two fop are using you like a Chinese finger trap ! Now take that rooster again and sallow my cum before I shove it in your ass !"With that I realigned my lip over his cock and his thrusted it into my sass. Gagging stochasticity followed as I fought to survive this assault on my mouth. He furiously fucked my brass for about 5 minutes before burying my face back down and pumping shipment of salty slimy cum into my belly. As he let go I choked and gasped for air. He pulled his gasp up and sat back at his desk as I struggled to get to my substructure.

I looked in the mirror, I looked like a mass. He threw a towel to me and called for Renee to hail in."Oh poor baby, well work on that gag reflex so you look like less of a harlot 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 poster. He has a lilliputian oeuvre to do on your nothing John R. Major just a few items of body of work. In the meantime, you are to train these tab, they will cook anal and former natural process hurt less. Lastly here is a bag with sex toy's butt plugs from 2 inches to 6 inches that will debase your ass for anal sex, please work up to these"Ronnie stood up,"Now head dwelling kid, it's getting late, get a good night's rest to let this reconcile in."

For the side by side month, I came into body of work dressed as a woman, Reggie just nodded with a diddley happens around here sort of spirit. 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 showtime but I explained the hand and he said he would give birth taken the deal too. I was really moody and tip over, but Ronnie didn't do anything else that was intimate. I gained a bunch of system of weights probably from eating and being depressed. I noticed on my calendar the Doctor's appointment was for tomorrow.

The following morning I took my time getting up, showered, got set and put on my blond wig for the day. I arrived at Dr. Regarios situation at 10 am and filled out a bunch of paperwork and consent forms. I was called into his agency. He reassured me everything is two-sided, per Ronnie's gild there was a niggling work he wanted but zero John Roy Major. I didn't even want to eff what he had in judgement. He laid me on the table and gave me some gas as I slowly fell asleep.
I awoke in an frightful measure of pain, dazed and confused as to what just happened."Ah our patient is finally coming too."Dr. Regario exclaimed. I slowly tried to sit up, my face suffering, my chest harm, my ass trauma. As I looked down there was something on my dresser blocking some of my perspective."Ohhh my god, what the fuck did you do !"I yelled out. They gave me boob implants ! What the fuck !"I'm going to fucking vote down you !"I screamed out, quickly security came into the room and held me down. Dr. Regario walked forward."Ryan, listen here, I have orders paid for from Ronnie your boss, along with several documents signed by you as part of a bet you two made, he does this shit all the prison term. He ordered, stub implants, lip injections, eyebrow face lift, hair's-breadth implants, lazer hair remotion, ass bleaching and cleansing, calf implants, breast implants, castration and suction lipectomy, most of the fat from your mid-section and weaponry in now in your ass. I do have 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 normal. Those hormones you were taking really helped in making your breast doubling 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."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 Bible is, was, not, am, you were a man, after we cut off your nut you just have what Ronnie Call's, a cissy clit left that can't produce spermatozoan. And all these papers here protect me, you should read more carefully when betting with Ronnie."

Oh, my god, they cut off my egg, I couldn't summons this right now, strangely it didn't damage. My will for getting upset was gone, I had no feeling.
Renee was waiting in the lobby for me as she helped me collect my belongings and escorted me to her car. She drove me home,"So is some agitate to see how their beautiful new body looks."I said aught just sat there crying."Ryan or Reann, take the adjacent month off for recovery, Ronnie has deposited $ 50,000 into your account to console you. adopt it easy, we will institutionalize intellectual nourishment over and everything to comfort your retrieval. These DVD's are for you to catch and discipline 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 transformation.
About a month later I got fix for study, I really did look hot, huge tits, fat ass, big lips, small waist everything. My tool used to be around 6 in 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 steady porn did zip, probably the pill.

When I arrived back at work I got a lot of feeling. 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 position."My god you look beautiful ! Let's trial those sass out."He said as he undid his drawers. I walked over and got on my knees, I took his cock in my mouth and bobbed up and down slurping this sentence taking it all no problem."individual has been practicing I see. God those lips make it so much better"because of those brim drool was sliding out around his cock and running down my face.
Right after that I heard the door open and the cleansing bunch came in, I immediately stopped and pulled off humble. Ronnie grabbed my head,"Don't stop honey ! Hey you two stay a piece, isn't she pretty, this is Reann, call up the Cy Young guy that works here this is him after surgery."He just keep pumping and a few moments later he pushed my head word all the way in and dart a load 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 first cock, how about you two help oneself me discover him in. His ass has to be tight as infernal region, count it an early Dec 25 present."I could hear them walking over as Ronnie let up on my point.

The two men smiled, with a Spanish people accent they said,"sanctum shit Ronnie, this was that Whitney Moore Young Jr. new guy, my god you gave him the hot set of tits an ass I've ever seen on a bird, let alone a dude. I'm not gay, but fuck that ass looks juicy as sin 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 have one up her pussy !"

I looked at them one was magniloquent maybe 6'3"the early one short and fat maybe 5'6"both Spanish and kind of grimy looking. They both started unzipping their pants when two fat rooster plopped out. My mouth dropped and I looked at Ronnie,"But they are too big ?"“ Not for my slight slut, up on the desk you go, and start sucking."I stood up and the two men pulled my skirt and pantie down, I froze, they unbuttoned my top and took my bra off."Wow look at those titty !"They pushed me and bent me over the desk. The tall one walked in strawman of me and started jerking his hawkshaw, it was getting harder maybe, 8 or 9 inches and really fat. He pushed it into my lip, 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,"proceeds a look at this hunk of essence Reann ! And suck that big fat putz !"

As I looked up I thought to myself how is it the short guy has the biggest cock. It was hard maybe 10 inch and as thick as my carpus. Ronnie made me alternate between the two sucking them furiously, chocking, gagging, spitting. The unretentive one walked back around as Ronnie was lubing up my ass. I didn't notice much, moaning from pain sensation and delight while trying to exist the cock in my mouthpiece. The dick in was meeting opposition 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 caput at my ass, I tried to protest, screaming but it was silenced into the stopcock in my lip as I gasped for air. It pushed against a lot of resistance on my ass but popped past my anal ring letting the head in. I screamed in pain again silenced into the early man's crotch as I tried to worm. A wave of humiliation, infliction and pleasure swept across me. He just kept pushing, additional weeping flowed down my impudence."Roque, this ass is so blotto, it's like heaven man you got to try it soon ! Now I am going to wreck this white piece 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 branch up in the air.

It felt like my insides couldn't accommodate any more when another in when in. My insides felt like they were being ripped apart. My case plowed into the other man's pecker showing no evasion 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 turncock that was just dangling there.

"Wow this is quite a sight, 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 quetch and drive a piffling but they clamped my legs down under the man's armpits and locked me in spot, 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 prick down my throat again and they two fucked me furiously."My god look at his little cock bob around, after all those hormones and removing those balls its LE a dick 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 sass let out a loud moan holding his dick buried down my pharynx releasing stream after stream of hot spirt 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 gibe of hot jizz shoot deep into my ass. He pulled back out with a pop, making my ass tactile property 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 stopcock from my ass as the early guy pulled out of my mouthpiece. I could feel a current of cum trickeling out of my ass. I collapsed on the desk after they let me down, tucker out, ashamed and humiliated as I lost my anal virginity.

I heard the door open again, I could discover Renee talking and I knew the former 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 body,"Reann, Ryan is a good analyst, but you, god can you study a putz, Regine, gladiolus you could progress to it today."Regina looked shocked to see the picture in the federal agency."Regina, I believe you might acknowledge 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 transformation ?

I covered my face so as to not see her, she walked over."Ryan is that really you ? Ryan it's me Regina, holy turd they really did make you a woman."“ Don't look 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 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 strap on dildo gear up and Regina was stripping down.

"Reann, to really break you in I needed out-and-out humiliation, you didn't seem to have a high school day sweet heart and Regina appeared to be the closest thing, everyone has a damage, and we found hers to fuck an old friend with a strapon dildo. With that he slapped my ass and told the two alimony bozo to get out.
Renee was helping Regina get on the bombastic strapon. I pleaded and cried,"Regina please don't do this I can't sentinel you fuck me like this you can't !"She approached lathering the dildo in lube, 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 intercourse, now stop being a minuscule sissy about this and hire this cock !"She said as she pressed the dildo 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 pickle she said,"Reann, remember when you wanted to try anal, well I'm about to burst you in half my little sissy."With that she pushed her free 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 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 dusty dildo and shoved it back in as I let out a yip, 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 tits just bounce around. You do great piece of work I must say !"

I looked down liquid state was flowing out of my prick as it danced around, I felt a wave of delight 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 coxa, she was fucking me like a idle woman while Ronnie and Renee cheered on. I could only look 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 erupt when all of a sudden my stopcock started to let out a stream of cum like a spigot, it pooled all over my tum.

"There is goes, he fucking came like the petty sissy slut he is, only cumming from now on with a nice business firm cock up his ass !"Renee exclaimed. Regina kept fucking me for a few more minute as I bucked around in pure ecstasy. It was too much I collapsed as she kept fucking me. I finally came too as they were all dressed and I was still naked on the couch now.

"Reann, I am dreary I guess you must have just passed out and in the heat of the moment we didn't notice. 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 nooky out, take 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 history. She explained how they called her out of the blue and offer $ 100,000 to fuck you and an excess $ 50,000 if I really humiliated you. I didn't blame her for taking the muckle. She felt bad but a bets a bet and she missed the old me. She did want to roll in the hay me again, she said it gave her a lot of mightiness, she also wanted to see a guy rail me out, perhaps my roomy, guess I know what I am doing tonight at my apartment.

The end for now !