I came from a Youngstown OH, my family was really poor growing up and life history wasn't easy. My Fatherhood 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 tending at night. Since I was really proficient at math and managed to get a scholarship to OH State I found a way out. I got a arcdegree in math with a focus in statistics. I applied to line all over the country and got a few good consultation lined up in NYC. With the little money I had from my previous night working at a bar I flew out to NYC and interviewed with some small-scale hedge stock. 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 flighty but confident at the same time about this move. I had a few troll of interviews with HPQ Advisors and finally I got the job as an psychoanalyst. Starting salary was $ 65,000 with carrying out based fillip. My first workweek Reginold, went by Reggie told me the incentive aren't the only way of getting surplus income, Ronnie the possessor likes making picayune stake here or there with staff.
NYC was bang-up minus one matter, the monetary value, I had found a two-bedroom apt that one bed room was for economic rent but it was $ 1,300 per calendar month and I had student loan of $ 800 per month. long minute, eating out and socializing left me no room to part with from my cash flow.

I was in the toilet one day and noticed Ronnie was in there washing his mitt 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 geological fault to healthcare sphere, which has worked out quite nicely."“ Yes, sir that was me."“ Well why don't you meet me for lunch at Bobby sunburn 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 job associates talk about various topic, nigh of which made my stomach crook since it was all about how to easily take reward of the hapless 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 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 tabular array myself included.

"Boy let me paraphrase that, if it hits 300 per portion you get $ 20K, if it hits 100 per share you stop dressing as a man and start dressing like a woman in the office."He had a sinister look on his aspect, the other two gentlemen were serenity 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 necessitate a 50 % plus pull back to hit his number. Come by my office when we get back and we will work out the specifics.
I had a fiddling bit of a bad look but still sure-footed I could get that $ 20k to pay off my scholar loans as I walked into his office. I sat down in front of his desk,"My boy, we need to work out these particular, let me ask, I looked over your resume, where you are from etc, how much do you owe in student loanword and how about that as the wager ?"“ I owe $ 80,000, you'd be willing to bet that much on one line ?"“ Absolutely boy, how often 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 program, let's do this, $ 500,000, if you win you get $ 500K, if you lose, you become my slave for intimate favors with me and my friends, you will seem like a woman, make up, little operating theatre here or there, federal agency hussy eccentric look, we lost ling stopping point month and she was the power 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 case, you would be able to help your family line back house and what are the prospect the livestock cliff to 100, in fact make it 90 and you have to hit 275 ? Think about how easily you can attain your life great ! pile or no tidy sum no thinking this one over end of story."I took a thick breath,"Deal !"we shook hands, his right man Robert spoke up,"ok boys, we have a bet here for a great sum of money, I will enlist up the sound paperwork and have you both sign of the zodiac tomorrow fair enough ?"We both nodded.

My ticker 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 take a shit those bets, he had won a similar bet and spend a penny $ 100K on the deal. I felt much respectable, I closely tracked the stock for the few month it hit 257 before quickly plummeting to 175, I thought I was going to cry, when it rallied back a petty but there was all this news about dirt going on etc. adjacent matter I know my gist sank and my chunk 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 office were a few women with clothing single-foot 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, sound way to learn is to get you balls kicked in. In your typesetter's case, literally, now Renee make him await pretty,"she looked at me,"seed with us to the women's cabinet room in the gym downstairs."My heart was racing, these three beautiful cleaning woman walked me to the women's locker."cartoon strip down, let's see what we are working with."I turned beatnik red, I am 5'9"and weight 150 lbs with a lanky body frame."Step in the cascade, and plane your all your fuzz but your head, make surely you get your asshole too,"They handed me shaving pick, consistence wash and shampoo. I took the exhibitor 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 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 flip-flop and bra. We went back up to the billet I went in through the back into Ronnie's part."Ahh there is my winnings, let's get you into a dainty appropriate office attire."He made me model different dress off the rack settling on 1.5 inch blackguard, a contraband dress with a tight white button down. He had the women leave the position and he sat on the couch."Time to pop paying up boy, hope you like cock because you're going to have a lot of cock in your lifespan going forward. I will create sure you are well taken tending of, just get quick to chug a lot of cock"

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 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, 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 kiss any other vocation honest bye. I can easily end you and your family from any normal creation. Now open up and exonerate you tears !"

I wiped away my tears and approached his crotch, I looked down at his flaccid extremity maybe about 5 column inch slightly thick."That a girl, he said, now suck this like the slovenly woman you are."As he said this he grabbed the back of my heading and lined it up with his pecker."Relax missy, slow your breathing, my cock will grow inside your oral fissure 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 belief on what I say from the pornos I've watched and took the capitulum in fully. He moaned in acceptance and I just bobbed up and down slowly working in as many in as I could.

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

I just wanted this to end, I bobbed furiously, my script caressed his balls, loudly slurping strait came out of my oral fissure. He put his hand behind my head and I felt him push down harder, his hawkshaw must have been about 6 - 6.5 inches now and maybe 1.5 in wide. I might sustain been down 4 in when I felt his tip slam against the back of my pharynx causing me to gag. He had shoved my head down and with both bridge player behind my head held me tight. I continued to go, rip streamed down and spit flowed from his mouth. He buried my boldness into his pubes and release quickly allowing me an opportunity to breath as I gasped for air. While trying to arrest my breath he just kept pushing down my head as I dodged his cock, rubbed my spit all over my face.
"Isn't life funny, one day you're some democratic college kid banging girls the future you've got your head buried in some sometime man's crotch while you choke on his prick and the day after that two beau are using you like a Chinese finger's breadth 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 cock and his thrusted it into my mouth. Gagging noises followed as I fought to survive this ravishment on my mouth. He furiously fucked my expression for about 5 minutes before burying my font back down and pumping slews 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 animal foot.

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 babe, well work on that gag reflex so you look like less of a prostitute when you're done. Here is your suitcase with you outfit for tomorrow. Please see Dr. Regario next month on the 15th at 10 am. Here is his card. He has a little employment to do on your zilch John Major just a few point of workplace. In the meantime, you are to take these pills, they will make anal and early bodily function hurt less. Lastly here is a bag with sex toy's butt plugs from 2 inches to 6 in that will stretch your ass for anal sex, please body of work up to these"Ronnie stood up,"Now head household kid, it's getting late, get a good Nox's quietus 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 looking at. 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 outset but I explained the deal and he said he would have taken the deal too. I was really moody and swage, 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 good morning I took my meter 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 crew of paperwork and consent forms. I was called into his office. He reassured me everything is reversible, per Ronnie's order there was a little work he wanted but nothing major. I didn't even want to sleep together what he had in nous. He laid me on the table and gave me some gas as I slowly fell asleep.
I awoke in an awful amount 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 hurt, my chest hurt, my ass suffering. As I looked down there was something on my dresser blocking some of my view."Ohhh my god, what the fuck did you do !"I yelled out. They gave me bosom implants ! What the fuck !"I'm going to fucking vote out you !"I screamed out, quickly security came into the way 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 contribution of a bet you two made, he does this shit all the time. He ordered, nates implants, lip injections, eyebrow aerodynamic lift, hair implants, lazer hair remotion, ass bleaching and cleansing, sura implants, tit implants, expurgation and liposuction, most of the fat from your mid-section and limb in now in your ass. I do deliver to say you came out pretty damn hot though !"

My heart 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 tit bivalent 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 of the Church you can't leave me like this, I am a man, I can't go abode like this."The Dr looked at me"Well the key word of honor is, was, not, am, you were a man, after we cut off your Lucille Ball you just have what Ronnie outcry's, a Milquetoast button 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 clump, I couldn't physical process this right wing now, strangely it didn't scathe. My will for getting upset was gone, I had no feeling.
Renee was waiting in the foyer for me as she helped me gather my belongings and escorted me to her car. She drove me dwelling house,"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 write up to soothe you. Take it easy, we will station food over and everything to still your convalescence. These DVD's are for you to watch and train that ass by the way."My roomy was shocked, and just didn't say a watchword as I walked in with patch and the obvious transformation.
About a month later I got fix for piece of work, I really did look hot, immense knocker, fat ass, big lips, pocket-sized waist everything. My cock used to be around 6 inches now barely 5 and skinny when hard. The DVD was fully of milksop sex and hypno, I used my dildos and stub plugs. For some rationality the dildos really made me cum and unconstipated porn did nothing, probably the contraceptive pill.

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 felicitous. Ronnie wants to see you after work."

right wing as everyone was leaving for the day I walked into Ronnie's office."My god you look beautiful ! Let's examination those lips out."He said as he undid his pants. I walked over and got on my knees, I took his turncock in my mouth and bobbed up and down slurping this metre taking it all no problem."Someone has been practicing I see. God those lips make it so much better"because of those lips drool was sliding out around his cock and running down my face.
rightfulness after that I heard the door open and the cleanup crowd came in, I immediately stopped and pulled off gangrene. Ronnie grabbed my straits,"Don't stop honey ! Hey you two stay a while, isn't she pretty, this is Reann, remember the young guy that works here this is him after surgery."He just keep pumping and a few moments later he pushed my drumhead all the way in and shoot a onus deep down my pharynx. I whipped my face for cum and saliva.

The two Spanish men just laughed. Ronnie told them,"Hey no one has ever broken him in, I am his beginning cock, how about you two avail me break him in. His ass has to be tight as blaze, consider it an early Yule present."I could hear them walking over as Ronnie let up on my school principal.

The two men smiled, with a Spanish accent they said,"Holy shit Ronnie, this was that young new guy, my god you gave him the hottest set of tits an ass I've ever seen on a bird, let alone a buster. I'm not gay, but fuck that ass looks juicy as hellhole 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 only one in the room that will deliver one up her pussycat !"

I looked at them one was tall maybe 6'3"the early one little and fat maybe 5'6"both Spanish people and kind of grimy looking. They both started unzipping their pants when two fat pecker plopped out. My mouth dropped and I looked at Ronnie,"But they are too big ?"“ Not for my footling slattern, up on the desk you go, and start up sucking."I stood up and the two men pulled my bird and step-in down, I froze, they unbuttoned my top and took my bra off."Wow look at those tits !"They pushed me and crouch me over the desk. The marvellous one walked in front of me and started jerking his dick, it was getting harder maybe, 8 or 9 in and really fat. He pushed it into my sassing, 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 lump of inwardness Reann ! And suck that big fat peter !"

As I looked up I thought to myself how is it the short-change guy has the expectant cock. It was hard maybe 10 inches and as midst as my radiocarpal joint. Ronnie made me interchange between the two sucking them furiously, chocking, gagging, spitting. The curt one walked back around as Ronnie was lubing up my ass. I didn't notice much, moaning from pain and pleasance while trying to survive the cock in my mouth. The shaft in was meeting resistivity 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 stopcock mind at my ass, I tried to resist, screaming but it was silenced into the cock in my mouth as I gasped for air. It pushed against a lot of 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 waving of humiliation, hurting and pleasure swept across me. He just kept pushing, additional crying flowed down my cheeks."Roque, this ass is so loaded, it's like nirvana 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 column inch in as I jolted forward on the desk, kicking my legs up in the air.

It felt like my inside 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 cock showing no escape from the hammer. 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 egg slapped against my little cock that was just dangling there.

"Wow this is quite a sight, your shaft are impaling this small female child on both ending 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 sound off and press a little but they clamped my stage down under the man's armpit and locked me in home, the light guy lined his dick up again and thrusted in as I screamed out in pain. The early man silenced me quickly ramming his cock down my throat again and they two fucked me furiously."My god looking at his minuscule cock bob around, after all those endocrine and removing those balls its lupus erythematosus a cock and more of an itsy bitsy sissy clitsy !"All the men laughed while I was mercilessly railed out on both remnant. Siliva and tongue ran down my nerve the man in my mouth let out a loud moan holding his cock buried down my pharynx releasing watercourse after stream of hot spirt of cum into my belly.

He stayed there as I continued to chock on his cum and stopcock. 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 fill you up !"He shouted as I felt scene after shot of hot jizz shoot deep into my ass. He pulled back out with a pop, making my ass feeling 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 turncock from my ass as the former guy pulled out of my mouth. I could feel a watercourse of cum trickeling out of my ass. I collapsed on the desk after they let me down, dog-tired, ashamed and humiliated as I lost my anal retentive virginity.

I heard the doorway capable again, I could hear Renee talking and I knew the other voice 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 thoroughly analyst, but you, god can you consider a cock, Regine, gladiola you could cook it today."Regina looked offend to see the shot in the office."Regina, I believe you might bang this little light-haired bimbo lying here, this is Ryan, now Reann, he made a bet and let's say he lost more than just the wager, how do you like the shift ?

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 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 no-count 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 you in I needed right-down humiliation, you didn't seem to have got a high school sweet core and Regina appeared to be the closest affair, everyone has a damage, and we found hers to love an old booster 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 ticker 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 charwoman now, your not the guy I used to fuck, now stop being a little sissy about this and subscribe this cock !"She said as she pressed the dildo header 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 free hole she said,"Reann, remember when you wanted to try anal, well I'm about to split you in half my little sissy."With that she pushed her weightiness 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 twist tip, it is about 2 inches in diam right around the middle, or simply put, we don't expect you to fare in tomorrow after Regina splits you ass in half, and you're about at the wooden-headed part."right wing 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 Milquetoast I am."Ronnie, look what you did, his little sissy clit is dripping precum mild and flopping around while his Brobdingnagian tits just bounce around. You do great workplace I must say !"

I looked down liquid was flowing out of my cock as it danced around, I felt a waving of pleasure building up in my ass. I started to moan, what was happening to me. My groan and panting grew louder as her dildo bucked against my rosehip, she was fucking me like a uncivilised woman while Ronnie and Renee cheered on. I could only await up at the faces as they stared in a enchantment 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 cock started to let out a stream of cum like a faucet, it pooled all over my tummy.

"There is goes, he fucking came like the little sissified slut 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 minutes as I bucked around in pure ecstasy. It was too a good deal I collapsed as she kept fucking me. I finally came too as they were all dressed and I was still naked on the sofa now.

"Reann, I am no-account I guess you must have just passed out and in the heat of the bit we didn't poster. 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 ass out, take the day off tomorrow, you've done decent work today."

Regina and I went out to dinner, I was ashamed and told her the hale story. She explained how they called her out of the wild blue yonder and offer $ 100,000 to fuck you and an extra $ 50,000 if I really humiliated you. I didn't incrimination her for taking the raft. She felt bad but a bets a bet and she missed the old me. She did want to fuck me again, she said it gave her a lot of mogul, she also wanted to see a guy rail in me out, perhaps my roommate, guess I know what I am doing tonight at my apartment.

The end for now !