I came from a Youngstown OH, my kin was really pathetic growing up and life wasn't easy. My Fatherhood moved out and left us when I was only 10 and my female parent supported the family working at a supermarket during the day and bar attention at Nox. Since I was really proficient at math and managed to get a encyclopedism to Ohio state of matter I found a way out. I got a degree in maths with a focus in statistics. I applied to jobs all over the country and got a few good interviews lined up in NYC. With the fiddling money I had from my late nighttime working at a bar I flew out to NYC and interviewed with some small-scale hedge investment firm. 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 queasy but positive at the Sami clip about this move. I had a few round of drinks of interviews with HPQ adviser and finally I got the job as an analyst. Starting salary was $ 65,000 with performance based fillip. My outset week Reginold, went by Reggie told me the bonuses aren't the entirely way of getting redundant income, Ronnie the owner likes making piddling bet here or there with staff.
NYC was keen minus one thing, 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 scholar loans of $ 800 per calendar month. farsighted 60 minutes, eating out and socializing left me no way to spare from my cash flow.

I was in the bath one day and noticed Ronnie was in there washing his mitt as I was."Hey kid you new here ?"he asked. I nodded,"my gens is Ryan ”."Ah, yes Ryan you were the one that suggested the Recent epoch shift to healthcare sector, which has worked out quite nicely."“ Yes, sir that was me."“ well why don't you meet me for lunch at Bobby Tans 1 pm sharp."

Wow this is so exciting, I get to eat with Ronnie, he was loaded. We sat down and I listened to him and two early business fellow talk about assorted topics, to the highest degree of which made my stomach turn since it was all about how to easily contract advantage of the poor in the country etc."So, you like healthcare right now, which lineage in particular proposition boy ?"“ Well sir Valeantz looks like a decent buy right now it is trading at 228 but my computation 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 swallow and everyone burst out laughing at the table myself included.

"Boy let me rephrase 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 forbidding look on his face, the early two gentlemen 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 involve a 50 % plus draw back to hit his number. Come by my authority when we get back and we will play out the specifics.
I had a little bit of a bad feeling but still sure-footed I could get that $ 20k to pay off my student loans as I walked into his government agency. I sat down in figurehead of his desk,"My boy, we need to work out these details, let me ask, I looked over your CV, where you are from etc, how much do you owe in student loan and how about that as the bet ?"“ I owe $ 80,000, you'd be bequeath to bet that much on one stock ?"“ Absolutely boy, how often do you require on top of that,"“ How about $ 100,000 plus the $ 80,000 if you want me to walk around like a adult female ?"“ sound like a programme, let's do this, $ 500,000, if you win you get $ 500K, if you lose, you become my slave for sexual favors with me and my ally, you will reckon like a woman, make up, little surgery here or there, position slut type look, we lost Heather hold out month and she was the business 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 case, you would be capable to help your family back home and what are the chances the stock drops to 100, in fact make it 90 and you have to hit 275 ? remember about how easily you can nominate your life history great ! Deal or no slew no thinking this one over end of story."I took a cryptic breath,"Deal !"we shook hands, 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 legal 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 untimely as I looked flushed. I explained to him the wager. He explained to me, that Ronnie loved to make those bets, he had won a alike bet and make up $ 100K on the deal. I felt much punter, I closely tracked the inventory 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 tidings about scandal going on etc. side by side matter I know my heart sank and my balls pulled up, 110, 100, then it happened it closed at 75. Robert approached me, Ronnie would like to see you in his role.

I took my pass of shame, waiting inside Ronnies office were a few fair sex with article of clothing racks etc."My boy, you win some you lose some, I didn't even see that coming this quickly but I also didn't see it hitting $ 275, best way to larn is to get you balls kicked in. In your vitrine, literally, now Renee make him calculate pretty,"she looked at me,"semen with us to the women's locker room in the gym downstairs."My heart was racing, these three beautiful women walked me to the women's storage 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."stride in the shower, and shave your all your haircloth but your head, make for certain you get your arsehole too,"They handed me shaving cream, eubstance 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 impertinence, 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 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 office I went in through the vertebral column into Ronnie's office."Ahh there is my winnings, let's get you into a Nice seize post attire."He made me sit different clothes off the wheel settling on 1.5 inch dog, a black wearing apparel with a tight white clit down. He had the women leave the role and he sat on the couch."fourth dimension to pop out paying up boy, hope you like cock because you're going to let a lot of tool in your life going forward. I will name trusted you are well taken care of, just get ready to chug a lot of cock"

I looked into the mirror and started to cry, I went from a pretty commodity looking guy, to a blond bimbo in one day. With that he unzipped his pant and pulled out his phallus. I protested as I cried,"Ryan, no one likes a coke job where the woman is crying before they even gag. Now you made this bet and could ingest become rich, it was worth the bet for you and this is worth it for me. Now if you don't contain up your end, go back home and start working at the supermarket where your mom is because buss any other career dependable bye. I can easily end you and your kin from any pattern world. Now open up and clear you tears !"

I wiped away my bust and approached his privates, I looked down at his flaccid penis maybe about 5 inch slightly thick."That a girl, he said, now suck this like the slattern you are."As he said this he grabbed the dorsum of my head teacher and lined it up with his dick."Relax girl, slow your breathing, my cock will mature inside your back talk 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 sense of taste bad, it was rather salty. I did my best opinion on what I say from the porn I've watched and took the head in fully. He moaned in toleration and I just bobbed up and down slowly working in as many inch as I could.

"feeling up at me, I have to see you with my cock buried in your passably lilliputian mouth, you realize there is no way out but to do a good job."I stared up at him, bout still building, bobbing up and down as I felt his tool slowly growing inside my mouth.

I just wanted this to end, I bobbed furiously, my hands caressed his balls, brassy slurping sound came out of my sass. He put his hand behind my nous and I felt him push down harder, his dick must let been about 6 - 6.5 inches now and maybe 1.5 inches all-embracing. I might feature been down 4 inch when I felt his tip slam against the back of my throat causing me to gag. He had shoved my read/write head down and with both hand behind my head word held me cockeyed. I continued to choke, snag streamed down and saliva flowed from his back talk. He buried my fount into his pubes and release quickly allowing me an opportunity to breath as I gasped for air. While trying to catch my breath he just kept pushing down my nous as I dodged his turncock, rubbed my spit all over my face.
"Isn't life funny, one day you're some pop college kid banging girls the next you've got your head buried in some Old man's genitalia while you choke on his dick and the day after that two dude are using you like a Formosan digit gob ! Now take that hammer again and sallow my cum before I shove it in your ass !"With that I realigned my oral fissure over his pecker and his thrusted it into my oral fissure. Gagging noise followed as I fought to endure this assault on my mouth. He furiously fucked my aspect for about 5 minutes before burying my look back down and pumping lashings of salty slimy cum into my belly. As he let go I choked and gasped for air. He pulled his gasp up and sat back at his desk as I struggled to get to my feet.

I looked in the mirror, I looked like a heap. He threw a towel to me and called for Renee to come in."Oh pitiable baby, well study on that gag reflex so you look like lupus erythematosus of a woman of the street when you're done. Here is your suitcase with you outfit for tomorrow. Please see Dr. Regario next calendar month on the 15th at 10 am. Here is his wag. He has a little body of work to do on your zippo major just a few token of work. In the meantime, you are to take these pills, they will pull in anal and other activities hurt less. Lastly here is a bag with sex toy's butt wad from 2 inches to 6 in that will stretch your ass for anal sex, please work up to these"Ronnie stood up,"Now head family kid, it's getting late, get a good night's eternal rest to let this settle in."

For the adjacent month, I came into work dressed as a woman, Reggie just nodded with a shit happens around here kind of looking. No one seemed shocked at all. Reggie mentioned that same bullshit happened to heather before she left. My roommate didn't say much, a bit broken at commencement but I explained the deal and he said he would throw taken the deal too. I was really temperamental and upset, but Ronnie didn't do anything else that was sexual. I gained a lot of weighting probably from eating and being depressed. I noticed on my calendar the medico's appointment was for tomorrow.

The following morning I took my clip 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 form. I was called into his place. 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 have sex what he had in creative thinker. He laid me on the tabular array and gave me some gas as I slowly fell asleep.
I awoke in an horrific 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 side hurt, my bureau hurt, my ass trauma. As I looked down there was something on my bureau blocking some of my view."Ohhh my god, what the piece of tail did you do !"I yelled out. They gave me breast 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 Order paid for from Ronnie your genus Bos, along with various documents signed by you as part of a bet you two made, he does this shit all the time. He ordered, butt implants, lip injections, eyebrow nip and tuck, hair implants, lazer hair removal, ass bleaching and cleansing, calf implants, breast implants, castration and liposuction, most of the fat from your mid-section and weaponry in now in your ass. I do have to say you came out pretty imprecate hot though !"

My affection sank and I passed out. I awoke again."That happened a lot around here, perfectly convention. Those hormones you were taking really helped in making your mamilla stunt man ds by the way, they gave us just enough tissue around the edges."I thought I was dreaming earlier until he made that remark. I just started to cry."medico you can't leave me like this, I am a man, I can't go rest 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 yell's, a pansy 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 egg, I couldn't process this right now, strangely it didn't hurt. My will for getting upset was gone, I had no feeling.
Renee was waiting in the vestibule 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 dead body looks."I said nothing just sat there crying."Ryan or Reann, take the succeeding month off for recovery, Ronnie has deposited $ 50,000 into your account to console you. ingest it easygoing, we will send food for thought over and everything to ease your recovery. These DVD's are for you to check and train that ass by the way."My roommate was shocked, and just didn't say a Son as I walked in with bandages and the obvious transformation.
About a calendar month later I got ready for study, I really did look hot, vast tits, fat ass, big lip, belittled waist everything. My cock used to be around 6 inches now barely 5 and skinny when difficult. The DVD was fully of sissy sex and hypno, I used my dildos and fag plugs. For some reason the dildos really made me cum and regular porn did cipher, probably the anovulatory drug.

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 as everyone was leaving for the day I walked into Ronnie's function."My god you look beautiful ! Let's test those sass out."He said as he undid his pants. I walked over and got on my knees, I took his putz in my oral fissure and bobbed up and down slurping this time taking it all no job."individual has been practicing I see. God those lips make it so much dear"because of those lips drool was sliding out around his hammer and running down my face.
right wing after that I heard the doorway out-of-doors and the cleaning crew came in, I immediately stopped and pulled off mortified. Ronnie grabbed my head,"Don't stay love ! 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 hold pumping and a few mo later he pushed my read/write head all the way in and buck 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 putz, how about you two serve me break him in. His ass has to be tight as underworld, take it an betimes Christmas present."I could hear them walking over as Ronnie let up on my head.

The two men smiled, with a Spanish emphasis they said,"sanctum shit Ronnie, this was that youthful new guy, my god you gave him the hottest set of tits an ass I've ever seen on a chick, let alone a fellow. I'm not gay, but fuck that ass looks juicy as Hades and those back talk were built for sucking cock."Ronnie looked to them,"don't worry it's only gay when there is a putz in your ass, Reann is the only one in the way that will own one up her pussycat !"

I looked at them one was tall maybe 6'3"the other one short and fat maybe 5'6"both Spanish and kind of grimy looking. They both started unzipping their bloomers when two fat pecker plopped out. My mouth dropped and I looked at Ronnie,"But they are too big ?"“ Not for my piddling slut, up on the desk you go, and start 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 front of me and started jerking his hawkshaw, it was getting intemperately maybe, 8 or 9 column inch 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 peter !"

As I looked up I thought to myself how is it the short guy has the biggest cock. It was unvoiced maybe 10 inches and as thick as my wrist. Ronnie made me alternate between the two sucking them furiously, chocking, gagging, spitting. The shortsighted one walked back around as Ronnie was lubing up my ass. I didn't notice much, moaning from pain and pleasure while trying to endure the stopcock in my oral fissure. The gumshoe 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 protest, screaming but it was silenced into the hammer in my mouthpiece as I gasped for air. It pushed against a lot of impedance on my ass but popped past my anal retentive ring letting the head in. I screamed in pain again silenced into the other man's privates as I tried to twist. A wave of mortification, pain and pleasure swept across me. He just kept pushing, additional tears 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 wreck this white piece of ass thought fucking clean and jerk this up whiteness boy !"He shouted thrusting about 5 inches in as I jolted forward on the desk, kicking my pegleg 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 hammer. He pulled out and rammed it back in getting maybe 8 inches in, pulling out again before ramming me into the other man's cock again as his balls slapped against my little cock that was just dangling there.

"Wow this is quite a batch, your peter are impaling this footling little girl on both end like an accordion ! Why don't you lift him up ?"With that I tried to resist but nothing helped, they lifted me off the desk and flipped me upside down rotating me in midair, I tried to kick and advertise a little but they clamped my stage down under the man's axilla and locked me in shoes, the short guy lined his turncock up again and thrusted in as I screamed out in pain. The other man silenced me quickly ramming his cock down my throat again and they two fucked me furiously."My god aspect at his footling rooster bob around, after all those endocrine and removing those clump its less a cock and Sir Thomas More of an itsy bitsy epicene clitsy !"All the men laughed while I was mercilessly railed out on both ends. Siliva and spit ran down my cheeks the man in my mouth let out a tacky moan holding his cock buried down my throat releasing stream after stream of hot K 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 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 sate you up !"He shouted as I felt shaft after injection 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 turncock from my ass as the former guy pulled out of my oral fissure. I could sense a stream 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 capable again, I could take heed 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 good analyst, but you, god can you drive a peter, Regine, glad you could puddle it today."Regina looked appall to see the scene in the post."Regina, I believe you might know this petty 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 transformation ?

I covered my font so as to not see her, she walked over."Ryan is that really you ? Ryan it's me Regina, holy place 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 sorry honey but Ronnie is paying me a lot of money to do what I am about to do, please forgive me."As I looked up I could see Renee getting a strap on dildo set and Regina was stripping down.

"Reann, to really get out you in I needed absolute chagrin, you didn't seem to have a high school gratifying inwardness and Regina appeared to be the closelipped thing, everyone has a price, and we found hers to eff an old friend with a strapon dildo. With that he slapped my ass and told the two maintenance guy wire to get out.
Renee was helping Regina get on the gravid strapon. I pleaded and cried,"Regina please don't do this I can't sentinel you fuck me like this you can't !"She approached lathering the dildo in lube, Renee and Ronnie lifted my legs up in the air exposing my cum dripping ass."Reann, you're a woman now, your not the guy I used to fuck, now stop being a minuscule milksop about this and take this cock !"She said as she pressed the dildo nous against my ass. This was beyond humiliating, I used to fuck her and always wanted to try anal but not like this. As she pressed harder breaking the barrier of my already loose jam she said,"Reann, remember when you wanted to try anal retentive, 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 curved tip, it is about 2 inches in diam rightfulness around the middle, or simply put, we don't expect you to do 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 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 sissy I am."Ronnie, look what you did, his niggling pantywaist clitoris is dripping precum diffused and flopping around while his immense mamilla 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 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 hips, she was fucking me like a wild cleaning lady 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 putz started to let out a current of cum like a faucet, it pooled all over my abdomen.

"There is goes, he fucking came like the lilliputian effeminate jade he is, only cumming from now on with a skillful firm shaft up his ass !"Renee exclaimed. Regina kept fucking me for a few Thomas More proceedings as I bucked around in pure ecstasy. It was too lots I collapsed as she kept fucking me. I finally came too as they were all dressed and I was still naked on the lounge now.

"Reann, I am blue I guess you must have just passed out and in the heat of the moment we didn't notice. Are your ok."Regina asked. I nodded to them Let's get you dressed and out of here she said. Ronnie and Renee were heading out,"Hey Reann lock up and get the piece of tail out, take the day off tomorrow, you've done enough work today."

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

The end for now !