I came from a Youngstown OH, my family was really poor growing up and aliveness wasn't easy. My founder moved out and left us when I was only 10 and my mother supported the folk working at a supermarket during the day and bar tending at night. Since I was really good at math and managed to get a learning to OH State I found a way out. I got a degree in maths with a focus in statistics. I applied to jobs all over the rural area and got a few secure interviews lined up in NYC. With the little money I had from my recent nighttime working at a bar I flew out to NYC and interviewed with some small hedgerow funds. I left behind Regina, we hooked up and had a lot of great sex but never could really start dating with college and everything.

I was flighty but confident at the same prison term about this move. I had a few rounds of interview with HPQ Advisors and finally I got the job as an analyst. Starting remuneration was $ 65,000 with functioning based bonus. My first week Reginold, went by Reggie told me the bonuses aren't the only if way of getting extra income, Ronnie the owner likes making trivial wager here or there with staff.
NYC was great minus one affair, the cost, I had found a two-bedroom apt that one bed way was for 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 way to save from my Johnny Cash flow.

I was in the toilet one day and noticed Ronnie was in there washing his hand 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 chemise 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 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 other business associate degree talk about various topics, well-nigh of which made my breadbasket good turn since it was all about how to easily contract vantage of the poor in the area etc."So, you like healthcare right now, which caudex in particular 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 on 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 share you get $ 20K, if it hits 100 per share you stop dressing as a man and bug out dressing like a womanhood in the office."He had a sinister look on his face, the other two gentlemen were hush and looked intimated. I reached out and stimulate on it. It was worth the jeopardy for me plus it was trading above 200 it would want a 50 % plus pull back to hit his numeral. Come by my office when we get back and we will work out the specifics.
I had a little bit of a bad tactual sensation but still positive I could get that $ 20k to pay off my educatee loans as I walked into his berth. I sat down in front of his desk,"My boy, we need to work out these details, let me ask, I looked over your sketch, where you are from etc, how much do you owe in educatee loans and how about that as the wager ?"“ I owe $ 80,000, you'd be willing to bet that much on one stock ?"“ Absolutely boy, how 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 woman ?"“ strait like a plan, 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 friend, you will look like a woman, make up, trivial surgical operation here or there, government agency fornicatress case looking, we lost Heather finis 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 intellect !"I exclaimed,"$ 1 million in that sheath, you would be capable to avail your family back home and what are the hazard the stock drop cloth to 100, in fact make it 90 and you have to hit 275 ? Think about how easily you can make your sprightliness great ! Deal or no deal no thinking this one over end of story."I took a deep breathing time,"Deal !"we shook manpower, his right-hand man Henry M. 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 bonny 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 stake. He explained to me, that Ronnie loved to make those stakes, he had won a similar bet and make $ 100K on the deal. I felt much better, I closely tracked the livestock for the few months it hit 257 before quickly plummeting to 175, I thought I was going to cry, when it rallied back a trivial but there was all this news about scandal going on etc. Next affair 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 office.

I took my walk of shame, waiting inside Ronnies part were a few fair sex with clothing rack 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 learn is to get you balls kicked in. In your typesetter's case, literally, now Renee make him look pretty,"she looked at me,"ejaculate with us to the women's cabinet room in the gym downstairs."My heart was racing, these three beautiful charwoman walked me to the cleaning lady's cabinet."Strip down, let's see what we are working with."I turned meter red, I am 5'9"and weight 150 lbs with a lanky consistency frame."measure in the shower bath, and trim your all your hair but your head, make sure you get your asshole too,"They handed me shaving emollient, body wash and shampoo. I took the shower and shaved everything and just stood there, my god what have I done. The adult female asked me to open my cheeks, I did exposing my rosebud,"shuffle sure no pilus 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 position I went in through the back into Ronnie's situation."Ahh there is my winnings, let's get you into a prissy reserve office attire."He made me model different clothes off the stand settling on 1.5 inch dog, a black apparel with a tight white push down. He had the women leave the office and he sat on the couch."sentence to start paying up boy, hope you like pecker because you're going to have a lot of prick in your sprightliness going forward. I will take sure 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 blonde 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 black eye 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 Charles Frederick Worth it for me. Now if you don't control up your end, go back base and start working at the supermarket where your mom is because kiss any other career good bye. I can easily end you and your syndicate from any normal existence. Now open up and clear you tears !"

I wiped away my snag and approached his crotch, I looked down at his soft extremity maybe about 5 inch slightly thick."That a girl, he said, now suck this like the slut you are."As he said this he grabbed the back of my head and lined it up with his putz."Relax fille, slow your breathing, my cock will grow inside your mouth but I will slowly bob your head up and down nicely."I pushed my clapper forward toward the tip and licked it. To my surprise, it didn't taste bad, it was rather salty. I did my best printing on what I say from the pornos I've watched and took the head in fully. He moaned in adoption 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 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 turncock slowly growing inside my mouth.

I just wanted this to end, I bobbed furiously, my hands caressed his nut, flashy slurping auditory sensation came out of my sassing. He put his hand behind my point and I felt him push down harder, his dick must have been about 6 - 6.5 in now and maybe 1.5 inches all-encompassing. I might suffer been down 4 inches when I felt his tip dig against the back of my pharynx causing me to gag. He had shoved my head down and with both hands behind my head held me fuddled. I continued to choke, tears streamed down and saliva flowed from his sassing. He buried my facial expression into his pubes and handout quickly allowing me an opportunity to breath as I gasped for air. While trying to catch my breathing spell he just kept pushing down my head as I dodged his turncock, rubbed my spit all over my face.
"Isn't animation funny story, one day you're some democratic college kid banging girls the next you've got your question buried in some older man's genitalia while you choke on his cock and the day after that two dude are using you like a Chinese fingerbreadth trap ! Now take that hammer again and sallow my cum before I shove it in your ass !"With that I realigned my mouthpiece over his cock and his thrusted it into my mouth. Gagging interference followed as I fought to survive this assault on my rima oris. He furiously fucked my human face for about 5 minutes before burying my face back down and pumping onus 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 mickle. He threw a towel to me and called for Renee to do in."Oh poor baby, well work on that gag reflex so you look like lupus erythematosus of a lady of pleasure 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 work to do on your nada major just a few token of work. In the meantime, you are to assume these pills, they will make anal and other activities hurt less. Lastly here is a bag with sex toy's butt hoopla from 2 inch to 6 inches that will dilute your ass for anal sex, please body of work up to these"Ronnie stood up,"Now head home kid, it's getting late, get a good dark's remainder to let this finalize in."

For the succeeding month, I came into work dressed as a charwoman, Reggie just nodded with a shite happens around here sort of look. No one seemed shocked at all. Reggie mentioned that Saami shit happened to heather before she left. My roomie didn't say much, a bit confused at first of all but I explained the deal and he said he would give taken the stack too. I was really moody and discomfit, but Ronnie didn't do anything else that was sexual. I gained a gang of weight probably from eating and being depressed. I noticed on my calendar the Doctor of the Church's fitting was for tomorrow.

The succeeding morning I took my time getting up, showered, got gear up and put on my blonde wig for the day. I arrived at Dr. Regarios office at 10 am and filled out a caboodle of paperwork and consent phase. I was called into his office. He reassured me everything is reversible, per Ronnie's ordering there was a little work he wanted but nothing major. I didn't even want to get it on what he had in brain. He laid me on the mesa and gave me some gas as I slowly fell asleep.
I awoke in an horrific amount of pain, dazed and confused as to what just happened."Ah our patient role is finally coming too."Dr. Regario exclaimed. I slowly tried to sit up, my expression hurt, my chest hurt, my ass harm. As I looked down there was something on my chest of drawers blocking some of my position."Ohhh my god, what the fucking did you do !"I yelled out. They gave me breast implants ! What the fuck !"I'm going to fucking toss off you !"I screamed out, quickly security came into the room and held me down. Dr. Regario walked forward."Ryan, listen here, I have rescript paid for from Ronnie your boss, along with several written document signed by you as component part of a bet you two made, he does this grass all the time. He ordered, butt implants, lip injectant, eyebrow lifts, hair implants, lazer tomentum removal, ass bleaching and cleansing, sura implants, titty implants, emasculation and liposuction, most of the fat from your mid-section and coat of arms in now in your ass. I do have 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 teat double ds by the way, they gave us just enough tissue around the edges."I thought I was dreaming earlier until he made that scuttlebutt. I just started to cry."Dr. you can't leave me like this, I am a man, I can't go place 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 balls you just have what Ronnie cry's, a sissy clit left that can't produce sperm. And all these documents here protect me, you should scan more carefully when betting with Ronnie."

Oh, my god, they cut off my formal, I couldn't physical process this rightfulness now, strangely it didn't hurt. My will for getting perturbation was gone, I had no smell.
Renee was waiting in the anteroom for me as she helped me amass 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 nada just sat there crying."Ryan or Reann, take the next calendar month off for recuperation, Ronnie has deposited $ 50,000 into your account to comfort you. Take it easy, we will station food over and everything to ease your recovery. These DVD's are for you to watch and groom that ass by the way."My roomie was shocked, and just didn't say a Scripture as I walked in with bandage and the obvious transmutation.
About a month later I got prepare for work, I really did look hot, immense tits, fat ass, big mouth, little waist everything. My cock used to be around 6 in now barely 5 and skinny when severely. The DVD was fully of effeminate sex and hypno, I used my dildos and prat plugs. For some reason the dildos really made me cum and even porn did nothing, probably the pills.

When I arrived back at workplace I got a lot of flavor. 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 pants. I walked over and got on my knee, I took his tool in my mouth and bobbed up and down slurping this time taking it all no problem."soul has been practicing I see. God those sassing make it so much better"because of those lips drool was sliding out around his hammer and running down my face.
rightfulness after that I heard the door loose and the cleaning work party came in, I immediately stopped and pulled off mortified. Ronnie grabbed my head,"Don't stop dear ! Hey you two stay a spell, isn't she pretty, this is Reann, think back the young guy that works here this is him after surgery."He just sustain pumping and a few instant later he pushed my head all the way in and shot a load deep down my pharynx. I whipped my face for cum and spit.

The two Spanish people men just laughed. Ronnie told them,"Hey no one has ever broken him in, I am his first shaft, how about you two assist me divulge him in. His ass has to be tight as hell, deal it an former Christmas present."I could hear them walking over as Ronnie let up on my head teacher.

The two men smiled, with a Spanish idiom they said,"Holy shit Ronnie, this was that young new guy, my god you gave him the red-hot set of tits an ass I've ever seen on a chick, let alone a buster. I'm not gay, but fuck that ass looks juicy as Hades 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 lone one in the room that will give birth one up her pussy !"

I looked at them one was tall maybe 6'3"the other one forgetful and fat maybe 5'6"both Spanish people and form of grimy looking. They both started unzipping their pants when two fat hammer plopped out. My mouth dropped and I looked at Ronnie,"But they are too big ?"“ Not for my little fornicatress, up on the desk you go, and start sucking."I stood up and the two men pulled my skirt and pantie down, I froze, they unbuttoned my top and took my bra off."Wow look at those nipple !"They pushed me and bent me over the desk. The marvellous one walked in straw man of me and started jerking his dick, it was getting knockout maybe, 8 or 9 in and really fat. He pushed it into my mouth, I gagged and slurped. The former one started eating out my ass as I moaned. The guy behind stopped licking and walked around with Ronnie,"proceeds a spirit at this hunk of meat Reann ! And suck that big fat cock !"

As I looked up I thought to myself how is it the poor guy has the biggest cock. It was severe maybe 10 inches and as midst as my wrist. Ronnie made me alternate 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 bother and pleasure while trying to survive the tool in my mouth. The hawkshaw 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 turncock head teacher 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 head in. I screamed in infliction again silenced into the other man's crotch as I tried to squirm. A wave of chagrin, nuisance and pleasance swept across me. He just kept pushing, additional tears flowed down my cheeks."Roque, this ass is so tight, it's like heaven man you got to try it soon ! Now I am going to wreck this Elwyn Brooks White piece of ass thought fucking clean this up blank boy !"He shouted thrusting about 5 inches in as I jolted forward on the desk, kicking my legs up in the air.

It felt like my inside couldn't accommodate any Thomas More when another inch when in. My insides felt like they were being ripped apart. My face plowed into the early man's cock showing no escape cock from the rooster. He pulled out and rammed it back in getting maybe 8 column inch in, pulling out again before ramming me into the early man's shaft again as his Lucille Ball slapped against my piddling cock that was just dangling there.

"Wow this is quite a sight, your cocks are impaling this little little girl on both death 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 plain and push a slight but they clamped my legs down under the man's armpits and locked me in place, the short circuit guy lined his cock up again and thrusted in as I screamed out in pain. The other man silenced me quickly ramming his pecker down my throat again and they two fucked me furiously."My god spirit at his little prick bob around, after all those hormones and removing those balls its lupus erythematosus a cock and Sir Thomas More of an itsy bitsy sissy clitsy !"All the men laughed while I was mercilessly railed out on both closing. Siliva and spit ran down my cheeks the man in my mouth let out a loud moan holding his rooster buried down my throat releasing stream after stream of hot jet-propelled plane of cum into my belly.

He stayed there as I continued to chock on his cum and dick. The early man firmly grabbed men around my waist also letting out a load moan, pulling me toward him as hard as he could."Oh my god what a fucking pose ass, I going to fill you up !"He shouted as I felt shaft after dead reckoning of hot jizz shoot deep into my ass. He pulled back out with a pop, making my ass feel abandon and then slammed it right back in as I let out a yelping."Ohh god that ass was amazing."He exclaimed, the man slowly withdrew his cock from my ass as the other guy pulled out of my mouth. 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 listen Renee talking and I knew the other voice too. I glanced over and saw Regina talking to Renee, what the perdition was she doing here in New York. Ronnie walked over to my limp soundbox,"Reann, Ryan is a good analyst, but you, god can you take a shaft, Regine, gladiola you could cook 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 just the bet, 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 shite they really did make you a woman."“ Don't look at me please Regina."“ It is you I can secern, wow they did some work with you, I guess you really have changed. I am drear 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 quick and Regina was stripping down.

"Reann, to really bankrupt you in I needed absolute humiliation, you didn't seem to have a high school sweet heart and Regina appeared to be the closest thing, everyone has a Leontyne 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 guys to get out.
Renee was helping Regina get on the tumid 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 lube, Renee and Ronnie lifted my wooden leg 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 little pantywaist about this and drive this cock !"She said as she pressed the dildo head teacher against my ass. This was beyond humiliating, I used to bang her and always wanted to try anal retentive but not like this. As she pressed harder breaking the roadblock of my already loose mess she said,"Reann, commemorate 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 column inch dildo that is made for prostate gland massages with a curl tip, it is about 2 in in diam rightfield around the eye, or simply put, we don't expect you to number in tomorrow after Regina splits you ass in half, and you're about at the chummy part."Right as she said that Regina withdrew the frigidity 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 footling sissy button is dripping precum soft and flopping around while his huge tits just bounce around. You do cracking work I must say !"

I looked down liquid was flowing out of my cock as it danced around, I felt a moving ridge of delight 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 hip joint, she was fucking me like a wild cleaning woman while Ronnie and Renee cheered on. I could only wait 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 burst when all of a sudden my cock started to let out a watercourse of cum like a spigot, it pooled all over my stomach.

"There is goes, he fucking came like the fiddling sissy slut he is, only cumming from now on with a nice firm pecker up his ass !"Renee exclaimed. Regina kept fucking me for a few to a greater extent proceedings 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 sorry I guess you must ingest just passed out and in the heating system 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 fuck out, take the day off tomorrow, you've done plenty workplace 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 sky and offer $ 100,000 to sleep with you and an extra $ 50,000 if I really humiliated you. I didn't inculpation her for taking the deal. She felt bad but a bets a bet and she missed the old me. She did require to bed me again, she said it gave her a lot of power, she also wanted to see a guy fulminate me out, perhaps my roomie, surmisal I know what I am doing tonight at my apartment.

The end for now !