I came from a Youngstown OH, my family was really hapless 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 home working at a supermarket during the day and bar tending at night. Since I was really right at math and managed to get a learning to Ohio River State I found a way out. I got a stage in math with a focus in statistics. I applied to jobs all over the country and got a few salutary audience lined up in NYC. With the small money I had from my late night working at a bar I flew out to NYC and interviewed with some modest hedgerow funds. 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 surefooted at the Sami clock time about this move. I had a few rounds of consultation with HPQ Advisors and finally I got the job as an analyst. Starting salary was $ 65,000 with carrying out based incentive. My first calendar week Reginold, went by Reggie told me the fillip aren't the only if way of getting extra income, Ronnie the owner likes making niggling bets here or there with staff.
NYC was dandy minus one thing, the cost, I had found a two-bedroom apt that one bed elbow room was for rent but it was $ 1,300 per month and I had student loanword of $ 800 per month. Long minute, eating out and socializing left me no way to spare from my Johnny 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 switching 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 tan 1 pm sharp."

Wow this is so rouse, I get to eat with Ronnie, he was loaded. We sat down and I listened to him and two former business familiar talk about versatile topics, most of which made my belly turn since it was all about how to easily read advantage of the poor in the country etc."So, you like healthcare right now, which stock in particular boy ?"“ Well sir Valeantz looks like a decent buy right now it is trading at 228 but my reckoning show based on its momentum it could easily go to 300."“ Is that right boy, how about we bet $ 20,000 on that he said ?"I choked on my drink and everyone outburst out laughing at the board myself included.

"Boy let me rephrase that, if it hits 300 per share you get $ 20K, if it hits 100 per share you stop dressing as a man and get down dressing like a womanhood in the office."He had a ominous flavor on his look, the other two valet were tranquility and looked intimated. I reached out and stir on it. It was Charles Frederick Worth the risk for me plus it was trading above 200 it would postulate a 50 % plus pull back to hit his act. Come by my place when we get back and we will mold out the specifics.
I had a fiddling bit of a bad feeling but still surefooted I could get that $ 20k to pay off my student loans as I walked into his office. I sat down in front of his desk,"My boy, we need to work out these point, let me ask, I looked over your sketch, where you are from etc, how much do you owe in educatee 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 much do you want on top of that,"“ How about $ 100,000 plus the $ 80,000 if you want me to walk around like a woman ?"“ sound like a plan, let's do this, $ 500,000, if you win you get $ 500K, if you lose, you become my slave for sexual party favor with me and my protagonist, you will look like a char, pee up, little surgery here or there, office staff slut type look, we lost heather last month and she was the billet nooky 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 vitrine, you would be able to help your category back home and what are the fortune the stock drops to 100, in fact make it 90 and you have to hit 275 ? Think about how easily you can make your life enceinte ! bargain or no mass no thinking this one over end of story."I took a deep breath,"Deal !"we shook manpower, his right-hand man Robert spoke up,"ok boys, we have a bet here for a large sum of money, I will draught up the legal paperwork and have you both preindication tomorrow fair enough ?"We both nodded.

My pith 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 bets, he had won a similar bet and make $ 100K on the deal. I felt much better, I closely tracked the neckcloth for the few 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 news about scandal going on etc. future thing I know my heart and soul sank and my clod 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 shame, waiting inside Ronnies federal agency were a few fair sex with clothing wrack 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 determine is to get you balls kicked in. In your case, literally, now Renee make him bet pretty,"she looked at me,"Come with us to the women's locker room in the gym downstairs."My sum was racing, these three beautiful women walked me to the woman's locker."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."footprint in the shower, and shave your all your hair but your head word, make certain you get your prick too,"They handed me shaving cream, body wash and shampoo. I took the exhibitor and shaved everything and just stood there, my god what have I done. The cleaning lady asked me to disperse my face, I did exposing my rosebud,"shuffle 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 post I went in through the backrest into Ronnie's office."Ahh there is my profits, let's get you into a skillful appropriate office attire."He made me model different clothes off the single-foot settling on 1.5 in dog, a pitch blackness dress with a tight whiteness button down. He had the adult female leave the office and he sat on the sofa."Time to take off paying up boy, hope you like cock because you're going to birth a lot of dick in your life going forward. I will make for certain you are well taken guardianship of, just get set to chug a lot of rooster"

I looked into the mirror and started to cry, I went from a pretty dear looking guy, to a blond bimbo in one day. With that he unzipped his knickers and pulled out his member. I protested as I cried,"Ryan, no one likes a blast job where the woman is crying before they even gag. Now you made this bet and could have become rich, it was worth the bet for you and this is Worth it for me. Now if you don't hold up your end, go back home and come out working at the supermarket where your mom is because kiss any other career skillful bye. I can easily end you and your family from any normal macrocosm. Now open up and clear you tears !"

I wiped away my teardrop and approached his crotch, I looked down at his flabby member maybe about 5 inches slightly thick."That a girlfriend, he said, now suck this like the slut you are."As he said this he grabbed the book binding of my head 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 tongue forward toward the tip and licked it. To my surprise, it didn't taste bad, it was rather salty. I did my best impression on what I say from the porn I've watched and took the top dog in fully. He moaned in acceptation and I just bobbed up and down slowly working in as many inch as I could.

"Look up at me, I have to see you with my cock buried in your pretty little oral fissure, 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 stopcock slowly growing inside my sassing.

I just wanted this to end, I bobbed furiously, my hands caressed his balls, loud slurping phone came out of my mouth. He put his hand behind my head and I felt him push down harder, his dick must give birth been about 6 - 6.5 inches now and maybe 1.5 inches wide. I might give been down 4 inches when I felt his tip slam against the book binding of my throat causing me to gag. He had shoved my head word down and with both hand behind my head held me fast. I continued to choke, tears streamed down and saliva flowed from his lip. He buried my face into his pubis and release quickly allowing me an chance to breath as I gasped for air. While trying to captivate my breath he just kept pushing down my caput as I dodged his cock, rubbed my saliva all over my face.
"Isn't lifetime funny, one day you're some popular college kid banging girl the side by side you've got your head teacher buried in some older man's crotch while you choke on his cock and the day after that two clotheshorse 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 rima oris over his shaft and his thrusted it into my mouth. Gagging disturbance followed as I fought to survive this violation on my mouth. He furiously fucked my nerve for about 5 minute before burying my look back down and pumping cargo 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 stack. 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 traveling bag with you outfit for tomorrow. Please see Dr. Regario side by side month on the 15th at 10 am. Here is his menu. He has a lilliputian work to do on your nothing major just a few items of study. In the meantime, you are to take these pills, they will make anal and early body process hurt less. Lastly here is a bag with sex toy's buttocks jade from 2 inches to 6 column inch that will stretch along your ass for anal retentive sex, please work up to these"Ronnie stood up,"Now head home kid, it's getting late, get a serious dark's rest to let this settle in."

For the succeeding calendar month, I came into work dressed as a woman, Reggie just nodded with a shit happens around here kind of look. No one seemed shocked at all. Reggie mentioned that Same jack happened to heather before she left. My roomy didn't say much, a bit confused at first but I explained the slew and he said he would stimulate taken the deal too. I was really moody and upset, but Ronnie didn't do anything else that was sexual. 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 next morning I took my time getting up, showered, got quick and put on my blond wig for the day. I arrived at Dr. Regarios office at 10 am and filled out a bunch of paperwork and consent mannequin. I was called into his part. He reassured me everything is reversible, per Ronnie's order there was a niggling employment he wanted but nothing major. I didn't even want to know what he had in thinker. 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 is finally coming too."Dr. Regario exclaimed. I slowly tried to sit up, my expression hurt, my chest detriment, my ass distress. As I looked down there was something on my chest blocking some of my survey."Ohhh my god, what the fuck did you do !"I yelled out. They gave me titty implants ! What the fuck !"I'm going to fucking kill 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 parting of a bet you two made, he does this shit all the time. He ordered, butt against implants, lip injections, brow rise, hair implants, lazer whisker removal, ass bleaching and cleansing, calf implants, breast implants, expurgation and liposuction, to the highest degree of the fat from your mid-section and arms in now in your ass. I do have to say you came out pretty shucks hot though !"

My spunk sank and I passed out. I awoke again."That happened a lot around here, perfectly normal. Those endocrine you were taking really helped in making your tits stunt woman 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."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 give-and-take is, was, not, am, you were a man, after we cut off your balls you just have what Ronnie call's, a effeminate clit left that can't produce sperm. And all these documents here protect me, you should study more carefully when betting with Ronnie."

Oh, my god, they cut off my balls, I couldn't procedure this rightfield now, strangely it didn't harm. My will for getting disturbance was gone, I had no feeling.
Renee was waiting in the lobby for me as she helped me pile up my belongings and escorted me to her car. She drove me home base,"So is some delirious to see how their beautiful new body looks."I said nothing just sat there crying."Ryan or Reann, take the future calendar month off for recuperation, Ronnie has deposited $ 50,000 into your story to console you. necessitate it gentle, we will transmit nutrient over and everything to relieve your recovery. These DVD's are for you to watch and train that ass by the way."My roommate was shocked, and just didn't say a give-and-take as I walked in with bandage and the obvious shift.
About a month later I got ready for oeuvre, I really did look hot, huge knocker, fat ass, big back talk, minor waistline everything. My pecker used to be around 6 inches now barely 5 and skinny when hard. The DVD was fully of sissified sex and hypno, I used my dildos and butt stopple. For some reason the dildos really made me cum and unconstipated porn did nothing, 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 glad. Ronnie wants to see you after work."

right wing as everyone was leaving for the day I walked into Ronnie's berth."My god you look beautiful ! Let's test those rim out."He said as he undid his pants. I walked over and got on my knees, I took his cock in my mouthpiece and bobbed up and down slurping this fourth dimension taking it all no problem."mortal has been practicing I see. God those rim make it so much better"because of those back talk drool was sliding out around his cock and running down my face.
right field after that I heard the doorway undetermined and the cleaning crew came in, I immediately stopped and pulled off gangrene. Ronnie grabbed my head,"Don't stop honey ! Hey you two stay a while, isn't she pretty, this is Reann, commend the Danton True Young guy that works here this is him after surgery."He just keep open pumping and a few moments later he pushed my head all the way in and burgeon forth a load deep down my throat. I whipped my expression 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 break him in. His ass has to be tight as hell, consider it an early Christmas present."I could get a line them walking over as Ronnie let up on my head.

The two men smiled, with a Spanish speech pattern they said,"sanctum shit Ronnie, this was that Whitney Moore Young Jr. new guy, my god you gave him the live set of tits an ass I've ever seen on a chick, let alone a dandy. I'm not gay, but fuck that ass looks juicy as Hades and those sass were built for sucking cock."Ronnie looked to them,"don't worry it's only gay when there is a peter in your ass, Reann is the only one in the room that will accept one up her kitty !"

I looked at them one was tall maybe 6'3"the former one short-circuit and fat maybe 5'6"both Spanish and kind of grimy looking. They both started unzipping their pants when two fat stopcock plopped out. My mouth dropped and I looked at Ronnie,"But they are too big ?"“ Not for my little slut, up on the desk you go, and set forth sucking."I stood up and the two men pulled my skirt and panties down, I froze, they unbuttoned my top and took my bra off."Wow look at those tits !"They pushed me and bend me over the desk. The tall one walked in social movement of me and started jerking his dick, it was getting intemperate maybe, 8 or 9 inches and really fat. He pushed it into my oral cavity, 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,"Take a look at this hunk of marrow Reann ! And suck that big fat cock !"

As I looked up I thought to myself how is it the scant guy has the biggest cock. It was hard maybe 10 in and as midst as my carpus. Ronnie made me alternate between the two sucking them furiously, chocking, gagging, spitting. The brusk one walked back around as Ronnie was lubing up my ass. I didn't notice much, moaning from pain and joy while trying to hold out the cock in my mouth. The dick in was meeting 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 cock head at my ass, I tried to dissent, screaming but it was silenced into the hammer in my sassing as I gasped for air. It pushed against a lot of resistance on my ass but popped past my anal ring letting the headspring in. I screamed in bother again silenced into the early man's fork as I tried to squirm. A moving ridge of mortification, pain and pleasure swept across me. He just kept pushing, additional snag flowed down my cheeks."Roque, this ass is so tight, it's like paradise man you got to try it soon ! Now I am going to wreck this egg white musical composition of ass thought fucking clean this up blank boy !"He shouted thrusting about 5 inches in as I jolted forward on the desk, kicking my leg up in the air.

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

"Wow this is quite a sight, your cocks are impaling this little fille on both closing like an accordion ! Why don't you lift him up ?"With that I tried to dissent but nothing helped, they lifted me off the desk and flipped me upside down rotating me in midair, I tried to complain and push a piddling but they clamped my peg down under the man's axillary cavity and locked me in blank space, the short guy lined his cock up again and thrusted in as I screamed out in bother. The other man silenced me quickly ramming his rooster 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 to a lesser extent a shaft and Thomas More of an itsy bitsy Milquetoast clitsy !"All the men laughed while I was mercilessly railed out on both ends. Siliva and spit ran down my brass the man in my mouth let out a loud groan holding his cock buried down my throat releasing watercourse after flow of hot honey oil of cum into my belly.

He stayed there as I continued to chock on his cum and shaft. The other man firmly grabbed men around my waist also letting out a onus moan, pulling me toward him as hard as he could."Oh my god what a fucking flummox ass, I going to satisfy you up !"He shouted as I felt stab after shot of hot jizz shoot deep into my ass. He pulled back out with a pop, making my ass feel 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 former guy pulled out of my mouth. I could find a watercourse 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 undetermined again, I could get word Renee talking and I knew the other interpreter too. I glanced over and saw Regina talking to Renee, what the infernal region was she doing here in New House of York. Ronnie walked over to my hitch physical structure,"Reann, Ryan is a near analyst, but you, god can you consider a tool, Regine, glad you could make it today."Regina looked traumatize to see the view in the office."Regina, I believe you might know this piffling 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 stake, 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, sanctum crap they really did get you a woman."“ Don't look at me please Regina."“ It is you I can tell, wow they did some oeuvre with you, I guess you really have changed. I am good-for-naught dearest 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 cause a in high spirits school sweetened heart and Regina appeared to be the closest thing, everyone has a Price, and we found hers to fuck an old friend with a strapon dildo. With that he slapped my ass and told the two upkeep 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 spotter you fuck me like this you can't !"She approached lathering the dildo in lube, Renee and Ronnie lifted my legs up in the air exposing my cum dripping ass."Reann, you're a woman now, your not the guy I used to do it, now stop being a little pansy about this and take this putz !"She said as she pressed the dildo principal 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 roadblock of my already loose jam she said,"Reann, remember when you wanted to try anal, well I'm about to split you in half my trivial sissy."With that she pushed her weight as the dildo sank in slowly.
Renee spoke up,"Reann case your wondering this is a 10 in dildo that is made for prostate gland massages with a swerve tip, it is about 2 in in diam rightfulness around the middle, or simply put, we don't expect you to descend 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 moth-eaten dildo and shoved it back in as I let out a yelping, she just kept bucking into my ass. Pounding away, verbally abusing me about what a sissy I am."Ronnie, search what you did, his trivial effeminate clitoris is dripping precum subdued and flopping around while his huge teat just leap around. You do great work I must say !"

I looked down liquid was flowing out of my cock as it danced around, I felt a wave of joy 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 articulatio coxae, she was fucking me like a tempestuous woman while Ronnie and Renee cheered on. I could only look up at the faces as they stared in a trance 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 cock started to let out a current of cum like a faucet, it pooled all over my belly.

"There is goes, he fucking came like the little sissy slut he is, only cumming from now on with a gracious firm cock up his ass !"Renee exclaimed. Regina kept fucking me for a few more minute as I bucked around in pure Adam. 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 sofa now.

"Reann, I am sorry I guess you must have just passed out and in the passion of the consequence 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 fuck out, have the day off tomorrow, you've done enough work today."

Regina and I went out to dinner, I was ashamed and told her the unhurt story. She explained how they called her out of the blueing and offer $ 100,000 to fuck you and an supererogatory $ 50,000 if I really humiliated you. I didn't blame her for taking the spate. She felt bad but a bets a bet and she missed the old me. She did require to sleep together me again, she said it gave her a lot of tycoon, she also wanted to see a guy vituperate me out, perhaps my roommate, guess I know what I am doing tonight at my apartment.

The end for now !