I came from a Youngstown OH, my family was really inadequate 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 encyclopedism to Ohio state of matter I found a way out. I got a degree in math with a focal point in statistics. I applied to chore all over the res publica and got a few good interviews 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 hedge pecuniary resource. 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 neural but confident at the same prison term about this motility. I had a few rounds of interview with HPQ Advisors and finally I got the job as an analyst. Starting salary was $ 65,000 with public presentation based bonus. My low week Reginold, went by Reggie told me the fillip aren't the only way of getting surplus income, Ronnie the proprietor likes making lilliputian bets here or there with staff.
NYC was great minus one thing, the monetary value, I had found a two-bedroom apt that one bed room was for rent but it was $ 1,300 per calendar month and I had bookman loans of $ 800 per calendar month. hanker 60 minutes, eating out and socializing left me no room to save from my Cash flow.

I was in the bathroom one day and noticed Ronnie was in there washing his hired man 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 recent shift 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 suntan 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 former business sector associates talk about various topics, about of which made my stomach tour since it was all about how to easily lease vantage of the inadequate in the country etc."So, you like healthcare right now, which stock in detail boy ?"“ Well sir Valeantz looks like a comme il faut buy right now it is trading at 228 but my calculations 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 burst out laughing at the table myself included.

"Boy let me rephrase that, if it hits 300 per contribution you get $ 20K, if it hits 100 per percentage you stop dressing as a man and get going dressing like a char in the office."He had a dark look on his aspect, the early two gentleman were quiet and looked intimated. I reached out and shook on it. It was worth the risk for me plus it was trading above 200 it would need a 50 % plus pull back to hit his number. Come by my part when we get back and we will work out the specifics.
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 office. I sat down in figurehead of his desk,"My boy, we need to work out these detail, let me ask, I looked over your curriculum vitae, where you are from etc, how much do you owe in scholar loans and how about that as the wager ?"“ I owe $ 80,000, you'd be volition to bet that much on one stock ?"“ Absolutely boy, how very much do you want on top of that,"“ How about $ 100,000 plus the $ 80,000 if you want me to take the air around like a woman ?"“ strait like a plan, let's do this, $ 500,000, if you win you get $ 500K, if you lose, you become my striver for sexual favors with me and my booster, you will look like a woman, clear up, little surgery here or there, power adulteress eccentric look, we lost Heather last month and she was the agency roll in the hay toy, so I am looking for another one and you fit the build."“ Are you out of your creative thinker !"I exclaimed,"$ 1 million in that case, you would be able to avail your family back home plate and what are the chances the stock drops to 100, in fact make it 90 and you have to hit 275 ? conceive about how easily you can make water your life great ! Deal or no deal no thinking this one over end of story."I took a late breath,"mess !"we shook manus, his right-hand man 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 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 wager. He explained to me, that Ronnie loved to relieve oneself those bets, he had won a like bet and cause $ 100K on the bargain. 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 scandal going on etc. Next thing I know my eye 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 position.

I took my walk of pity, waiting inside Ronnies office were a few cleaning woman with clothing wheel 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 learn is to get you ball kicked in. In your case, literally, now Renee make him appear pretty,"she looked at me,"seminal fluid with us to the women's cabinet room in the gym downstairs."My heart was racing, these three beautiful women walked me to the cleaning lady's locker."Strip down, let's see what we are working with."I turned round red, I am 5'9"and weight 150 lbs with a lanky body anatomy."Step in the shower, and shave your all your tomentum but your fountainhead, make certain you get your asshole too,"They handed me shaving cream, body wash and shampoo. I took the exhibitioner and shaved everything and just stood there, my god what have I done. The woman asked me to spread my cheeks, I did exposing my rosebud,"brand indisputable 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 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 part I went in through the rear into Ronnie's office."Ahh there is my winnings, let's get you into a nice seize office staff attire."He made me model unlike clothes off the stand settling on 1.5 in heel, a black dress with a tight white clit down. He had the woman leave the part and he sat on the couch."clip to start paying up boy, hope you like cock because you're going to have a lot of shaft in your animation going forward. I will make sure enough you are well taken care of, just get ready to chug a lot of shaft"

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 pants and pulled out his fellow member. I protested as I cried,"Ryan, no one likes a gust job where the woman is crying before they even gag. Now you made this bet and could have got become fertile, it was worth the bet for you and this is Charles Frederick Worth it for me. Now if you don't withstand up your end, go back home and pop out working at the supermarket where your mom is because osculation any former career good bye. I can easily end you and your folk from any rule existence. Now open up and elucidate you tears !"

I wiped away my split and approached his privates, I looked down at his flaccid member maybe about 5 in slightly thick."That a girl, he said, now suck this like the adulteress you are."As he said this he grabbed the back of my head and lined it up with his putz."Relax lady friend, slow your ventilation, my cock will arise 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 smut 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.

"Look up at me, I have to see you with my stopcock buried in your pretty little mouth, you realize there is no way out but to do a good job."I stared up at him, tears still building, bobbing up and down as I felt his cock slowly growing inside my back talk.

I just wanted this to end, I bobbed furiously, my deal caressed his balls, gimcrack slurping auditory sensation came out of my mouth. He put his helping hand behind my head and I felt him push down harder, his putz must have been about 6 - 6.5 column inch now and maybe 1.5 inches wide. I might ingest been down 4 column inch when I felt his tip jibe against the back of my throat causing me to gag. He had shoved my head down and with both custody behind my promontory held me tight. I continued to choke, rip streamed down and saliva flowed from his mouth. He buried my fount into his os pubis and loss quickly allowing me an opportunity to breath as I gasped for air. While trying to catch my breath he just kept pushing down my head as I dodged his putz, rubbed my spit all over my face.
"Isn't life funny, one day you're some democratic college kid banging young woman the adjacent you've got your head buried in some older man's crotch while you choke on his cock and the day after that two beau are using you like a Chinese finger trap ! Now take that prick again and sallow my cum before I shove it in your ass !"With that I realigned my mouth over his prick and his thrusted it into my mouth. Gagging noises followed as I fought to pull round this assault on my mouth. He furiously fucked my facial expression for about 5 moment 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 mass. He threw a towel to me and called for Renee to get in."Oh pitiable baby, well employment on that gag reflex so you look like less of a prostitute when you're done. Here is your grip with you outfit for tomorrow. Please see Dr. Regario side by side month on the 15th at 10 am. Here is his plug-in. He has a small piece of work to do on your nada major just a few items of workplace. In the meantime, you are to take these tab, they will make anal and other natural action hurt less. Lastly here is a bag with sex toy's butt male plug from 2 column inch to 6 inches that will stretch your ass for anal sex, please work up to these"Ronnie stood up,"Now head habitation kid, it's getting late, get a good night's rest to let this settle in."

For the next 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 Saami asshole happened to heather before she left. My roommate didn't say much, a bit confused at first but I explained the mountain and he said he would give birth 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 system of weights probably from eating and being depressed. I noticed on my calendar the MD's assignment was for tomorrow.

The next morning I took my time getting up, showered, got cook and put on my blonde wig for the day. I arrived at Dr. Regarios office at 10 am and filled out a bunch of paperwork and consent forms. I was called into his office. He reassured me everything is reversible, per Ronnie's orderliness there was a little work he wanted but nothing major. I didn't even want to get it on what he had in intellect. He laid me on the table and gave me some gas as I slowly fell asleep.
I awoke in an awful quantity 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 fount hurt, my chest of drawers hurt, my ass hurt. As I looked down there was something on my chest blocking some of my view."Ohhh my god, what the fuck did you do !"I yelled out. They gave me chest implants ! What the roll in the hay !"I'm going to fucking down you !"I screamed out, quickly certificate came into the elbow room and held me down. Dr. Regario walked forward."Ryan, listen here, I have guild paid for from Ronnie your hirer, along with respective papers signed by you as component of a bet you two made, he does this shit all the time. He ordered, nates implants, lip injections, eyebrow lifts, hair implants, lazer hair remotion, ass bleaching and cleansing, calf implants, breast implants, castration and liposuction, about of the fat from your mid-section and arms in now in your ass. I do have to say you came out pretty damn hot though !"

My substance sank and I passed out. I awoke again."That happened a lot around here, perfectly normal. Those internal secretion you were taking really helped in making your tits double up 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 house like this."The Dr looked at me"Well the key word is, was, not, am, you were a man, after we cut off your balls you just have what Ronnie call's, a Milquetoast button left that can't garden truck sperm. And all these documents here protect me, you should read more carefully when betting with Ronnie."

Oh, my god, they cut off my balls, I couldn't process this right now, strangely it didn't hurt. My will for getting derangement was gone, I had no feeling.
Renee was waiting in the foyer for me as she helped me collect my property and escorted me to her car. She drove me nursing home,"So is some excited to see how their beautiful new body looks."I said nothing 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 transmit food over and everything to ease your recovery. These DVD's are for you to watch and train that ass by the way."My roomie was shocked, and just didn't say a word as I walked in with bandages and the obvious transformation.
About a month later I got ready for work, I really did look hot, huge tits, fat ass, big lip, diminished shank everything. My cock used to be around 6 in now barely 5 and skinny when hard. The DVD was fully of pansy sex and hypno, I used my dildos and nates plugs. For some reason the dildos really made me cum and regular smut did nothing, probably the tablet.

When I arrived back at body of 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 felicitous. Ronnie wants to see you after work."

rightfulness as everyone was leaving for the day I walked into Ronnie's bureau."My god you look beautiful ! Let's mental test those lips out."He said as he undid his bloomers. I walked over and got on my knees, I took his dick in my mouth and bobbed up and down slurping this time taking it all no problem."Someone has been practicing I see. God those sassing make it so much better"because of those rim drool was sliding out around his cock and running down my face.
right after that I heard the room access open and the cleaning bunch came in, I immediately stopped and pulled off mortified. Ronnie grabbed my head,"Don't diaphragm honey ! Hey you two stay a while, isn't she pretty, this is Reann, remember the unseasoned guy that works here this is him after surgery."He just proceed pumping and a few moments later he pushed my head all the way in and germinate a payload 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 me conk out him in. His ass has to be tight as sin, believe it an too soon Yule present."I could get word them walking over as Ronnie let up on my promontory.

The two men smiled, with a Spanish people idiom they said,"holy shit Ronnie, this was that unseasoned new guy, my god you gave him the blistering set of titmouse an ass I've ever seen on a chick, let alone a fellow. I'm not gay, but fuck that ass looks juicy as pit and those lips 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 solitary one in the room that will cause one up her puss !"

I looked at them one was tall maybe 6'3"the other one short and fat maybe 5'6"both Spanish and variety 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 slovenly woman, up on the desk you go, and depart 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 titty !"They pushed me and bend me over the desk. The tall one walked in front of me and started jerking his shaft, it was getting harder maybe, 8 or 9 in and really fat. He pushed it into my back talk, I gagged and slurped. The other one started eating out my ass as I moaned. The guy behind stopped licking and walked around with Ronnie,"Take a look at this hunk of meat Reann ! And suck that big fat stopcock !"

As I looked up I thought to myself how is it the short guy has the biggest cock. It was hard maybe 10 column inch and as thick as my radiocarpal joint. Ronnie made me flip-flop 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 hurting and pleasure while trying to survive the cock in my backtalk. The tool in was meeting resistance when it finally pushed into my pharynx as I chocked and gagged. He pulled back out as I gasped for air and then jammed it back into my throat.

When I felt the cock straits at my ass, I tried to dissent, screaming but it was silenced into the cock in my oral cavity as I gasped for air. It pushed against a lot of impedance on my ass but popped past my anal pack letting the headway in. I screamed in pain again silenced into the other man's genitals as I tried to writhe. A wave of humiliation, painfulness and pleasure swept across me. He just kept pushing, extra tears flowed down my boldness."Roque, this ass is so tight, it's like Eden man you got to try it soon ! Now I am going to wreck this T. H. White patch of ass thought fucking clean and jerk this up albumen 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 interior couldn't accommodate any more when another inch when in. My insides felt like they were being ripped apart. My case plowed into the former man's hammer showing no evasion from the cocks. He pulled out and rammed it back in getting maybe 8 inch in, pulling out again before ramming me into the early man's cock again as his globe slapped against my slight tool that was just dangling there.

"Wow this is quite a deal, 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 dissent but zilch 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 armpits and locked me in place, the unawares guy lined his stopcock up again and thrusted in as I screamed out in pain. The other man silenced me quickly ramming his shaft 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 orb its to a lesser extent a prick and Thomas More of an itsy bitsy sissy clitsy !"All the men laughed while I was mercilessly railed out on both ends. Siliva and spitting ran down my cheeks the man in my mouth let out a brassy groan holding his cock buried down my pharynx releasing stream after stream of hot jets 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 shank also letting out a load moan, pulling me toward him as hard as he could."Oh my god what a fucking astonishing ass, I going to fill you up !"He shouted as I felt crack after shot of hot jizz shoot deep into my ass. He pulled back out with a pop, making my ass tone void 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 tool from my ass as the other guy pulled out of my mouthpiece. I could palpate a flow of cum trickeling out of my ass. I collapsed on the desk after they let me down, exhausted, ashamed and humiliated as I lost my anal virginity.

I heard the threshold open again, I could find out Renee talking and I knew the early vocalisation too. I glanced over and saw Regina talking to Renee, what the hell was she doing here in New House of York. Ronnie walked over to my limp body,"Reann, Ryan is a effective analyst, but you, god can you pack a rooster, Regine, glad you could wee-wee it today."Regina looked dismayed to see the aspect in the office."Regina, I believe you might know this little blonde bimbo lying here, this is Ryan, now Reann, he made a bet and let's say he lost more than than just the wager, how do you like the translation ?

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

"Reann, to really break in you in I needed absolute humiliation, you didn't seem to have a high school honeyed inwardness and Regina appeared to be the snug matter, everyone has a Leontyne Price, and we found hers to have intercourse an old friend with a strapon dildo. With that he slapped my ass and told the two 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 lubricator, Renee and Ronnie lifted my wooden leg up in the air exposing my cum dripping ass."Reann, you're a charwoman now, your not the guy I used to get it on, now stop being a little pansy about this and need this rooster !"She said as she pressed the dildo capitulum against my ass. This was beyond humiliating, I used to love her and always wanted to try anal but not like this. As she pressed harder breaking the barrier of my already loose maw she said,"Reann, retrieve when you wanted to try anal, well I'm about to dissever you in half my little sissy."With that she pushed her 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 curl tip, it is about 2 inch in diameter right around the middle, or simply put, we don't expect you to come in tomorrow after Regina splits you ass in one-half, and you're about at the thickest part."right wing as she said that Regina withdrew the insensate dildo and shoved it back in as I let out a yelp, she just kept bucking into my ass. Pounding away, verbally abusing me about what a sissy I am."Ronnie, look what you did, his little sissy clit is dripping precum easygoing and flopping around while his Brobdingnagian nipple just bounce around. You do outstanding work I must say !"

I looked down liquid was flowing out of my peter 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 moans and panting grew louder as her dildo bucked against my hips, she was fucking me like a wild womanhood while Ronnie and Renee cheered on. I could only look up at the faces as they stared in a trance at the huge 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 turncock started to let out a stream of cum like a faucet, it pooled all over my stomach.

"There is goes, he fucking came like the little sissy strumpet he is, only cumming from now on with a nice firm cock up his ass !"Renee exclaimed. Regina kept fucking me for a few more mo as I bucked around in pure hug drug. It was too often 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 give birth just passed out and in the heat 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, engage the day off tomorrow, you've done sufficiency work today."

Regina and I went out to dinner, I was ashamed and told her the altogether narrative. She explained how they called her out of the blue and offer $ 100,000 to fuck you and an duplicate $ 50,000 if I really humiliated you. I didn't rap her for taking the great deal. She felt bad but a bets a bet and she missed the old me. She did desire to fuck me again, she said it gave her a lot of might, she also wanted to see a guy rail me out, perhaps my roommate, guess I know what I am doing tonight at my flat.

The end for now !