I came from a Youngstown OH, my family was really hapless growing up and life wasn't easy. My Father of the Church moved out and left us when I was only 10 and my female parent supported the category working at a supermarket during the day and bar tending at night. Since I was really well at math and managed to get a scholarship to Ohio State I found a way out. I got a arcdegree in math with a focus in statistics. I applied to jobs all over the country and got a few good audience lined up in NYC. With the little money I had from my previous Nox working at a bar I flew out to NYC and interviewed with some small hedge fund. I left behind Regina, we hooked up and had a lot of slap-up sex but never could really originate dating with college and everything.

I was nervous but confident at the same fourth dimension about this move. I had a few rounds of interviews with HPQ advisor and finally I got the job as an psychoanalyst. Starting salary was $ 65,000 with carrying out based incentive. My first week Reginold, went by Reggie told me the bonus aren't the only way of getting redundant income, Ronnie the owner likes making little bets here or there with staff.
NYC was great minus one matter, the cost, I had found a two-bedroom apt that one bed room was for rent but it was $ 1,300 per month and I had student loanword of $ 800 per month. Long hr, eating out and socializing left me no room to spare from my hard currency flow.

I was in the privy one day and noticed Ronnie was in there washing his deal 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 shift to healthcare sphere, which has worked out quite nicely."“ Yes, sir that was me."“ fountainhead why don't you meet me for dejeuner 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 former line of work associates talk about various topics, most of which made my venter turn since it was all about how to easily take advantage of the poor in the country etc."So, you like healthcare right now, which broth in particular boy ?"“ Well sir Valeantz looks like a right buy right now it is trading at 228 but my calculations show based on its impulse it could easily go to 300."“ Is that decently boy, how about we bet $ 20,000 on that he said ?"I choked on my potable and everyone burst out laughing at the board myself included.

"Boy let me rephrase that, if it hits 300 per percentage you get $ 20K, if it hits 100 per portion you stop dressing as a man and start dressing like a woman in the office."He had a minacious looking at on his typeface, the other two man were quiet and looked intimated. I reached out and sway on it. It was worth the risk for me plus it was trading above 200 it would involve a 50 % plus pull back to hit his identification number. Come by my place when we get back and we will run out the specifics.
I had a lilliputian bit of a bad look but still convinced I could get that $ 20k to pay off my scholarly person loans as I walked into his government agency. I sat down in nominal head of his desk,"My boy, we need to work out these details, let me ask, I looked over your resume, where you are from etc, how a great deal do you owe in bookman 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 lots do you want on top of that,"“ How about $ 100,000 plus the $ 80,000 if you want me to walk around like a womanhood ?"“ audio like a programme, let's do this, $ 500,000, if you win you get $ 500K, if you lose, you become my hard worker for sexual favors with me and my champion, you will look like a woman, score up, footling surgery here or there, power slut case look, we lost broom last month and she was the office 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 subject, you would be able to assist your class back home and what are the prospect the stock dip to 100, in fact make it 90 and you have to hit 275 ? think about how easily you can prepare your life corking ! Deal or no sight no thinking this one over end of story."I took a deep breath,"trade !"we shook hands, his right-hand man Henry Martyn Robert spoke up,"ok boys, we have a bet here for a with child sum of money, I will draft up the legal paperwork and have you both foretoken tomorrow bonnie enough ?"We both nodded.

My heart was racing as I walked back to my desk, Reggie asked me what was faulty as I looked flushed. I explained to him the wager. He explained to me, that Ronnie loved to urinate those wager, he had won a similar bet and pee $ 100K on the deal. I felt much ameliorate, I closely tracked the strain for the few month it hit 257 before quickly plummeting to 175, I thought I was going to cry, when it rallied back a slight but there was all this news show about dirt going on etc. Next thing I know my heart sank and my balls pulled up, 110, 100, then it happened it closed at 75. Henry Martyn 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 charwoman with habiliment stand etc."My boy, you win some you lose some, I didn't even see that coming this quickly but I also didn't see it hitting $ 275, proficient way to con is to get you balls kicked in. In your case, literally, now Renee make him look pretty,"she looked at me,"Come with us to the womanhood's locker elbow room in the gym downstairs."My heart was racing, these three beautiful womanhood walked me to the charwoman'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."Step in the shower, and shave your all your hair but your head, make sure you get your asshole too,"They handed me shaving cream, organic structure laundry and shampoo. I took the shower and shaved everything and just stood there, my god what have I done. The woman asked me to circularize my cheeks, I did exposing my rosebud,"make sure as shooting no whisker 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 composition 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 office."Ahh there is my winnings, let's get you into a nice appropriate office attire."He made me pattern dissimilar clothes off the single-foot settling on 1.5 inch heels, a black frock with a close blanched clit down. He had the fair sex leave the bureau and he sat on the couch."Time to start paying up boy, hope you like shaft because you're going to bear a lot of dick in your aliveness going forward. I will name sure you are well taken care of, just get ready to chug a lot of turncock"

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 gasp and pulled out his member. I protested as I cried,"Ryan, no one likes a C job where the char 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 Charles Frederick Worth it for me. Now if you don't hold up your end, go back abode and start working at the supermarket where your mom is because kiss any other career sound bye. I can easily end you and your household from any normal creation. Now open up and unmortgaged you tears !"

I wiped away my tears and approached his genitalia, I looked down at his flaccid fellow member 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 head and lined it up with his peter."Relax daughter, slow your breathing, my cock will originate inside your oral cavity but I will slowly bob your head up and down nicely."I pushed my natural language forward toward the tip and licked it. To my surprise, it didn't taste perception bad, it was rather salty. I did my best impression on what I say from the pornos I've watched and took the head in fully. He moaned in acceptation 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 cock buried in your pretty picayune mouth, you realize there is no way out but to do a sound job."I stared up at him, weeping still building, bobbing up and down as I felt his cock slowly growing inside my sass.

I just wanted this to end, I bobbed furiously, my hands caressed his lump, loud slurping sounds came out of my mouthpiece. He put his script behind my head and I felt him press down harder, his dick must have been about 6 - 6.5 inch now and maybe 1.5 inches wide. I might get been down 4 inches when I felt his tip slam against the back of my throat causing me to gag. He had shoved my head down and with both manus behind my head held me tight. I continued to kick the bucket, rip streamed down and spittle flowed from his mouth. He buried my fount into his pubic region and firing quickly allowing me an chance to breath as I gasped for air. While trying to catch my breath he just kept pushing down my fountainhead as I dodged his cock, rubbed my spitting all over my face.
"Isn't life history funny, one day you're some pop college kid banging girls the next you've got your straits buried in some sure-enough man's genital organ while you choke on his hammer and the day after that two dude are using you like a Formosan finger gob ! 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 rima oris. Gagging noises followed as I fought to survive this rape on my mouth. He furiously fucked my look for about 5 proceedings before burying my brass back down and pumping lots 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 mess. He threw a towel to me and called for Renee to get in."Oh poor baby, well oeuvre on that gag reflex so you look like less of a whore when you're done. Here is your travelling bag with you outfit for tomorrow. Please see Dr. Regario adjacent calendar month on the 15th at 10 am. Here is his card. He has a trivial piece of work to do on your nil major just a few item of work. In the meantime, you are to take these birth control pill, they will piddle anal and former activeness hurt less. Lastly here is a bag with sex toy's stub plugs from 2 column inch to 6 inch that will stretch your ass for anal sex, please employment up to these"Ronnie stood up,"Now head home kid, it's getting late, get a good Night's rest to let this resolve in."

For the following month, I came into work dressed as a woman, Reggie just nodded with a darn happens around here kind of tone. 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 first base but I explained the hatful and he said he would experience taken the lot too. I was really Dwight Lyman Moody and upset, but Ronnie didn't do anything else that was sexual. I gained a gang of weighting probably from eating and being depressed. I noticed on my calendar the medico's appointment was for tomorrow.

The next cockcrow I took my time getting up, showered, got ready and put on my blonde wig for the day. I arrived at Dr. Regarios role at 10 am and filled out a bunch of paperwork and consent forms. I was called into his power. He reassured me everything is two-sided, per Ronnie's decree there was a little body of work he wanted but nothing John R. Major. I didn't even want to know what he had in idea. He laid me on the table and gave me some gas as I slowly fell asleep.
I awoke in an tremendous sum 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 harm. As I looked down there was something on my chest blocking some of my position."Ohhh my god, what the nookie did you do !"I yelled out. They gave me breast implants ! What the fuck !"I'm going to fucking obliterate you !"I screamed out, quickly security came into the elbow room and held me down. Dr. Regario walked forward."Ryan, listen here, I have parliamentary procedure paid for from Ronnie your chief, along with several documents signed by you as part of a bet you two made, he does this shop all the clip. He ordered, butt implants, lip injections, brow rhytidoplasty, hair's-breadth implants, lazer haircloth removal, ass bleaching and cleanup, calfskin implants, white meat implants, expurgation and liposuction, most of the fat from your mid-section and arms in now in your ass. I do induce 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 hormones you were taking really helped in making your breast double 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 word is, was, not, am, you were a man, after we cut off your balls you just have what Ronnie song's, a sissy clit left that can't produce sperm. And all these text file here protect me, you should record more carefully when betting with Ronnie."

Oh, my god, they cut off my ball, I couldn't process this right now, strangely it didn't injury. My will for getting turnover was gone, I had no feeling.
Renee was waiting in the pressure group for me as she helped me gather my belongings and escorted me to her car. She drove me home,"So is some excited to see how their beautiful new body looks."I said aught just sat there crying."Ryan or Reann, take the next month off for retrieval, Ronnie has deposited $ 50,000 into your write up to console you. Take it easy, we will send intellectual nourishment over and everything to ease 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 Bible as I walked in with patch and the obvious translation.
About a calendar month later I got gear up for body of work, I really did look hot, huge mamilla, fat ass, big sass, small waist everything. My cock used to be around 6 inch now barely 5 and skinny when hard. The DVD was fully of sissified sex and hypno, I used my dildos and butt plugs. For some understanding the dildos really made me cum and regular porn did nothing, probably the 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 happy. Ronnie wants to see you after work."

Right as everyone was leaving for the day I walked into Ronnie's office."My god you look beautiful ! Let's test those backtalk out."He said as he undid his pant. I walked over and got on my genu, I took his rooster in my backtalk and bobbed up and down slurping this time taking it all no problem."Someone has been practicing I see. God those mouth make it so much better"because of those lips drool was sliding out around his pecker and running down my face.
rightfield after that I heard the door open and the cleaning gang came in, I immediately stopped and pulled off mortified. Ronnie grabbed my pass,"Don't plosive consonant dear ! Hey you two stay a while, isn't she pretty, this is Reann, think back the Whitney Young guy that works here this is him after surgery."He just hold pumping and a few moments later he pushed my drumhead all the way in and shot 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 me break him in. His ass has to be tight as hell, consider it an early Christmas present."I could hear them walking over as Ronnie let up on my head.

The two men smiled, with a Spanish people dialect they said,"holy shit Ronnie, this was that young new guy, my god you gave him the raging set of titmouse an ass I've ever seen on a doll, let alone a beau. I'm not gay, but fuck that ass looks juicy as perdition and those lips 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 if one in the elbow room that will bear one up her pussy !"

I looked at them one was marvellous maybe 6'3"the former one short and fat maybe 5'6"both Spanish and variety of grimy looking. They both started unzipping their knickers when two fat prick plopped out. My mouth dropped and I looked at Ronnie,"But they are too big ?"“ Not for my minuscule slut, up on the desk you go, and depart sucking."I stood up and the two men pulled my dame and panties down, I froze, they unbuttoned my top and took my bra off."Wow look at those tits !"They pushed me and turn away me over the desk. The tall one walked in front of me and started jerking his dick, it was getting harder maybe, 8 or 9 inches 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 expression at this lump of center Reann ! And suck that big fat cock !"

As I looked up I thought to myself how is it the shortsighted guy has the large cock. It was hard maybe 10 inches and as thick as my wrist joint. Ronnie made me alternate between the two sucking them furiously, chocking, gagging, spitting. The myopic one walked back around as Ronnie was lubing up my ass. I didn't notice much, moaning from pain and pleasure while trying to survive the pecker in my mouth. The prick in was meeting underground 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 protest, screaming but it was silenced into the dick in my oral fissure as I gasped for air. It pushed against a lot of resistance on my ass but popped past my anal retentive ring letting the head in. I screamed in nuisance again silenced into the other man's crotch as I tried to twist. A waving of mortification, pain sensation and pleasure swept across me. He just kept pushing, additional snag flowed down my cheeks."Roque, this ass is so smashed, it's like Heaven man you got to try it soon ! Now I am going to wrack this lily-white piece of ass thought fucking clean this up egg white boy !"He shouted thrusting about 5 in in as I jolted forward on the desk, kicking my legs up in the air.

It felt like my insides 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 cocks. He pulled out and rammed it back in getting maybe 8 column inch in, pulling out again before ramming me into the former man's putz again as his Ball slapped against my small cock that was just dangling there.

"Wow this is quite a batch, your cocks are impaling this little lady friend on both ends 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 give up and push a little but they clamped my branch down under the man's armpit and locked me in home, the short guy lined his cock up again and thrusted in as I screamed out in infliction. The other man silenced me quickly ramming his putz 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 lupus erythematosus a cock and more of an itsy bitsy sissy clitsy !"All the men laughed while I was mercilessly railed out on both death. Siliva and spit ran down my impudence the man in my mouth let out a loud moan holding his cock buried down my throat 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 former 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 shooting after dig 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 yip."Ohh god that ass was amazing."He exclaimed, the man slowly withdrew his peter from my ass as the other 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, sap, ashamed and humiliated as I lost my anal virginity.

I heard the doorway open again, I could hear Renee talking and I knew the early interpreter too. I glanced over and saw Regina talking to Renee, what the Hades was she doing here in New House of York. Ronnie walked over to my hobble body,"Reann, Ryan is a serious psychoanalyst, but you, god can you take a pecker, Regine, glad you could attain it today."Regina looked shocked to see the scene 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 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 crap they really did make you a woman."“ Don't look at me please Regina."“ It is you I can say, wow they did some work with you, I guess you really have changed. I am dingy dear 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 fix and Regina was stripping down.

"Reann, to really break you in I needed absolute humiliation, you didn't seem to have a senior high school school sweetened heart and Regina appeared to be the closemouthed matter, everyone has a price, and we found hers to bonk an old friend with a strapon dildo. With that he slapped my ass and told the two sustenance guy wire 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 peg up in the air exposing my cum dripping ass."Reann, you're a womanhood now, your not the guy I used to fuck, now stop being a little sissy about this and take 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 retentive but not like this. As she pressed harder breaking the barrier of my already loose kettle of fish she said,"Reann, remember when you wanted to try anal, well I'm about to dissever 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 column inch dildo that is made for prostate massages with a curved tip, it is about 2 inches 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 frigidness 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, expect what you did, his little sissy button is dripping precum cushy and flopping around while his huge tits just bounce around. You do great piece of work I must say !"

I looked down liquid was flowing out of my cock as it danced around, I felt a Wave of pleasance 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 pelvis, she was fucking me like a raving mad charwoman while Ronnie and Renee cheered on. I could only appear 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 ignite when all of a sudden my cock started to let out a current of cum like a faucet, it pooled all over my stomach.

"There is goes, he fucking came like the little sissy slattern he is, only cumming from now on with a courteous 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 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 no-account I guess you must make just passed out and in the heat of the moment we didn't bill. 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 shtup out, take the day off tomorrow, you've done plenty work today."

Regina and I went out to dinner, I was ashamed and told her the whole storey. She explained how they called her out of the blueness and offer $ 100,000 to sleep together you and an extra $ 50,000 if I really humiliated you. I didn't blame her for taking the trade. She felt bad but a wager a bet and she missed the old me. She did need to fuck me again, she said it gave her a lot of ability, she also wanted to see a guy rail me out, perhaps my roomie, guess I know what I am doing tonight at my apartment.

The end for now !