I came from a Youngstown OH, my family was really piteous growing up and life sentence wasn't easy. My male parent 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 good at math and managed to get a erudition to OH State I found a way out. I got a level in math with a focus in statistic. I applied to jobs all over the res publica and got a few goodness interviews lined up in NYC. With the fiddling money I had from my previous night working at a bar I flew out to NYC and interviewed with some small hedge pecuniary resource. I left behind Regina, we hooked up and had a lot of great sex but never could really start dating with college and everything.

I was nervous but confident at the Lapplander time about this move. I had a few rounds of interview with HPQ Advisors and finally I got the job as an analyst. Starting salary was $ 65,000 with execution based incentive. My first off week Reginold, went by Reggie told me the incentive aren't the lonesome way of getting supererogatory income, Ronnie the owner likes making little wager here or there with staff.
NYC was great minus one thing, the price, I had found a two-bedroom apt that one bed room was for split but it was $ 1,300 per month and I had student loans of $ 800 per calendar month. Long hours, eating out and socializing left me no elbow room to spare from my cash flow.

I was in the bathroom one day and noticed Ronnie was in there washing his hands 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."“ Well why don't you meet me for luncheon 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 various subject, about of which made my breadbasket turn since it was all about how to easily select advantage of the pathetic in the res publica etc."So, you like healthcare right now, which blood line in particular boy ?"“ Well sir Valeantz looks like a adequate 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 mesa myself included.

"Boy let me paraphrase that, if it hits 300 per plowshare you get $ 20K, if it hits 100 per share you stop dressing as a man and come out dressing like a woman in the office."He had a sinister look on his side, the other two valet were quiesce 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 ask a 50 % plus deplumate back to hit his number. Come by my office when we get back and we will work out the specifics.
I had a niggling bit of a bad feel but still confident I could get that $ 20k to pay off my student loanword as I walked into his office. I sat down in front of his desk,"My boy, we need to bring out these particular, let me ask, I looked over your resume, where you are from etc, how much do you owe in student loans and how about that as the wager ?"“ I owe $ 80,000, you'd be uncoerced to bet that much on one stock ?"“ Absolutely boy, how a great deal do you want on top of that,"“ How about $ 100,000 plus the $ 80,000 if you want me to walk around like a cleaning woman ?"“ audio like a program, 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 friends, you will look like a woman, hit up, little surgery here or there, post slovenly woman case look, we lost Scots heather 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 case, you would be able to help your family back home and what are the chance the Malcolm stock drops to 100, in fact make it 90 and you have to hit 275 ? Think about how easily you can make your life-time great ! Deal or no deal no thinking this one over end of story."I took a deep breathing place,"tidy sum !"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 muster in up the sound paperwork and have you both signaling tomorrow average enough ?"We both nodded.

My heart was racing as I walked back to my desk, Reggie asked me what was wrong as I looked flushed. I explained to him the wager. He explained to me, that Ronnie loved to make those stake, he had won a similar bet and make $ 100K on the sight. I felt much better, I closely tracked the bloodline for the few months it hit 257 before quickly plummeting to 175, I thought I was going to cry, when it rallied back a fiddling but there was all this news about scandal going on etc. side by side affair I know my essence 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 situation.

I took my walk of shame, waiting inside Ronnies government agency were a few women with habiliment 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, proficient way to get a line is to get you balls kicked in. In your case, literally, now Renee make him look pretty,"she looked at me,"ejaculate with us to the women's locker room in the gym downstairs."My kernel was racing, these three beautiful charwoman walked me to the cleaning lady's locker."Strip down, let's see what we are working with."I turned pulsation red, I am 5'9"and weight 150 lbs with a lanky torso frame."footprint in the shower, and shave your all your hair but your head, make sure you get your son of a bitch too,"They handed me shaving emollient, dead body wash and shampoo. I took the shower and shaved everything and just stood there, my god what have I done. The cleaning woman asked me to open my impertinence, I did exposing my rosebud,"brand sure 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 makeup 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 back into Ronnie's office."Ahh there is my profits, let's get you into a prissy seize function attire."He made me sit different wearing apparel off the rack settling on 1.5 inch heels, a black garb with a crocked blanched clitoris down. He had the fair sex leave the office and he sat on the lounge."clip to pop out paying up boy, hope you like cock because you're going to have a lot of dick in your life going forward. I will ready sure you are well taken fear of, just get ready to chug a lot of cock"

I looked into the mirror and started to cry, I went from a pretty thoroughly 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 blow job where the char is crying before they even gag. Now you made this bet and could have become ample, it was worth the bet for you and this is worth it for me. Now if you don't book up your end, go back home and commence working at the supermarket where your mom is because kiss any other career just bye. I can easily end you and your house from any formula world. Now open up and clear you tears !"

I wiped away my tears and approached his crotch, I looked down at his flaccid member maybe about 5 inch slightly thick."That a missy, he said, now suck this like the loose woman you are."As he said this he grabbed the back of my head and lined it up with his dick."Relax missy, slow up your breathing, my cock will acquire inside your mouth but I will slowly bob your drumhead up and down nicely."I pushed my tongue forward toward the tip and licked it. To my surprise, it didn't taste bad, it was rather salty. I did my best impression on what I say from the pornos I've watched and took the head in fully. He moaned in acceptance and I just bobbed up and down slowly working in as many inches as I could.

"smell 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 skillful job."I stared up at him, snag still building, bobbing up and down as I felt his shaft slowly growing inside my mouthpiece.

I just wanted this to end, I bobbed furiously, my hands caressed his balls, loud slurping sounds came out of my mouth. He put his manus behind my headland and I felt him press down harder, his dick must consume been about 6 - 6.5 inches now and maybe 1.5 inches encompassing. I might have been down 4 inches when I felt his tip slam against the back of my pharynx causing me to gag. He had shoved my pass down and with both manpower behind my head held me tight. I continued to choke, bout streamed down and spit flowed from his oral cavity. He buried my face into his pubes and expiration quickly allowing me an opportunity to breath as I gasped for air. While trying to catch my breath he just kept pushing down my top dog as I dodged his cock, rubbed my expectoration all over my face.
"Isn't life story good story, one day you're some democratic college kid banging female child the succeeding you've got your head teacher buried in some onetime man's crotch while you choke on his cock and the day after that two dude are using you like a Chinese digit trap ! Now take that cock again and sallow my cum before I shove it in your ass !"With that I realigned my oral cavity over his putz and his thrusted it into my lip. Gagging noises followed as I fought to live this assault on my mouthpiece. He furiously fucked my nerve for about 5 minutes before burying my boldness back down and pumping loads of salty slimy cum into my belly. As he let go I choked and gasped for air. He pulled his pants up and sat back at his desk as I struggled to get to my metrical 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 people baby, well work on that gag reflex so you look like less of a whore when you're done. Here is your suitcase with you outfit for tomorrow. Please see Dr. Regario adjacent month on the 15th at 10 am. Here is his card. He has a little study to do on your nil major just a few token of work. In the meantime, you are to take these pills, they will make anal and other activities hurt less. Lastly here is a bag with sex toy's butt plugs from 2 in to 6 inches that will extend your ass for anal sex, please workplace up to these"Ronnie stood up,"Now head nursing home kid, it's getting late, get a good Nox's rest to let this go down in."

For the next month, I came into body of work dressed as a woman, Reggie just nodded with a shit happens around here kind of feel. No one seemed shocked at all. Reggie mentioned that same diddly happened to heather before she left. My roommate didn't say much, a bit put off at initiatory but I explained the lot and he said he would birth taken the deal too. I was really moody and upset, but Ronnie didn't do anything else that was sexual. I gained a crew of weighting probably from eating and being depressed. I noticed on my calendar the Doctor's naming was for tomorrow.

The following morning I took my time getting up, showered, got ready and put on my blond wig for the day. I arrived at Dr. Regarios office at 10 am and filled out a lot of paperwork and consent forms. I was called into his office staff. He reassured me everything is reversible, per Ronnie's order of magnitude there was a little work he wanted but nothing John R. Major. I didn't even want to get it on what he had in head. He laid me on the table and gave me some gas as I slowly fell asleep.
I awoke in an awe-inspiring sum of pain, dazed and confused as to what just happened."Ah our affected role is finally coming too."Dr. Regario exclaimed. I slowly tried to sit up, my face injury, my thorax hurt, my ass distress. As I looked down there was something on my pectus blocking some of my purview."Ohhh my god, what the piece of ass did you do !"I yelled out. They gave me knocker implants ! What the ass !"I'm going to fucking kill you !"I screamed out, quickly certificate came into the room and held me down. Dr. Regario walked forward."Ryan, listen here, I have orders paid for from Ronnie your Bos, along with several written document signed by you as component of a bet you two made, he does this shit all the clip. He ordered, tail implants, lip injections, brow rhytidoplasty, hair implants, lazer haircloth removal, ass bleaching and cleansing, calf implants, breast implants, castration and suction lipectomy, most of the fat from your mid-section and arms in now in your ass. I do suffer to say you came out pretty all-fired hot though !"

My core 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 knocker threefold 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."Doctor 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 God is, was, not, am, you were a man, after we cut off your balls you just have what Ronnie call's, a sissy clitoris left that can't produce sperm cell. And all these text file here protect me, you should read more carefully when betting with Ronnie."

Oh, my god, they cut off my balls, I couldn't cognitive operation this right now, strangely it didn't hurt. My will for getting upset was gone, I had no look.
Renee was waiting in the lobby for me as she helped me gather my property and escorted me to her car. She drove me home,"So is some activated to see how their beautiful new body looks."I said zilch just sat there crying."Ryan or Reann, take the adjacent month off for recovery, Ronnie has deposited $ 50,000 into your account to console you. Take it gentle, we will ship food over and everything to ease your recovery. These DVD's are for you to observe and train that ass by the way."My roommate was shocked, and just didn't say a word as I walked in with bandage and the obvious translation.
About a month later I got ready for workplace, I really did look hot, huge titty, fat ass, big mouth, small shank everything. My shaft used to be around 6 inches now barely 5 and skinny when laborious. The DVD was fully of sissy sex and hypno, I used my dildos and stern jade. For some reason the dildos really made me cum and fixture porn did nothing, probably the tablet.

When I arrived back at work I got a lot of feeling. 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 hand as everyone was leaving for the day I walked into Ronnie's office."My god you look beautiful ! Let's test those mouth out."He said as he undid his pant. I walked over and got on my knee, I took his cock in my oral fissure and bobbed up and down slurping this time taking it all no trouble."Someone has been practicing I see. God those brim make it so much dear"because of those lips drool was sliding out around his dick and running down my face.
right wing after that I heard the door open and the cleaning crew came in, I immediately stopped and pulled off mortified. Ronnie grabbed my head,"Don't period love ! Hey you two stay a piece, isn't she pretty, this is Reann, remember the unseasoned guy that works here this is him after surgery."He just keep pumping and a few moments later he pushed my head all the way in and pip a load deep down my throat. I whipped my face for cum and spittle.

The two Spanish people men just laughed. Ronnie told them,"Hey no one has ever broken him in, I am his first base prick, how about you two help me break him in. His ass has to be tight as hell, consider it an former Christmas present."I could learn them walking over as Ronnie let up on my foreland.

The two men smiled, with a Spanish people emphasis they said,"holy place 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 chick, let alone a dude. I'm not gay, but fuck that ass looks juicy as the pits 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 solely one in the elbow room that will have one up her pussy !"

I looked at them one was grandiloquent maybe 6'3"the other one scant and fat maybe 5'6"both Spanish and kind of grimy looking. They both started unzipping their pants when two fat dick plopped out. My mouth dropped and I looked at Ronnie,"But they are too big ?"“ Not for my minuscule hussy, up on the desk you go, and start sucking."I stood up and the two men pulled my skirt and panty down, I froze, they unbuttoned my top and took my bra off."Wow look at those tits !"They pushed me and twist me over the desk. The tall one walked in front line of me and started jerking his dick, it was getting harder maybe, 8 or 9 inch and really fat. He pushed it into my mouthpiece, I gagged and slurped. The early 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 meat Reann ! And suck that big fat dick !"

As I looked up I thought to myself how is it the unretentive guy has the biggest peter. It was arduous maybe 10 in and as thick as my carpus. Ronnie made me tack 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 pain and pleasure while trying to survive the cock in my sass. The dick 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 tool headway at my ass, I tried to protest, screaming but it was silenced into the cock in my backtalk as I gasped for air. It pushed against a lot of electrical resistance on my ass but popped past my anal anchor ring letting the head in. I screamed in pain again silenced into the other man's crotch as I tried to squirm. A wafture of humiliation, pain and pleasure swept across me. He just kept pushing, extra split flowed down my buttock."Roque, this ass is so taut, it's like Heaven man you got to try it soon ! Now I am going to wreck this Edward D. White while of ass thought fucking clean this up white 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 More when another inch when in. My insides felt like they were being ripped apart. My aspect plowed into the early 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 footling pecker that was just dangling there.

"Wow this is quite a sight, your hammer are impaling this fiddling girl on both ends like an accordion ! Why don't you lift him up ?"With that I tried to protest but zippo helped, they lifted me off the desk and flipped me upside down rotating me in midair, I tried to kick and promote a little but they clamped my ramification down under the man's armpit and locked me in place, the shortstop guy lined his shaft up again and thrusted in as I screamed out in pain. The former man silenced me quickly ramming his cock down my throat again and they two fucked me furiously."My god look at his little cock bob around, after all those internal secretion and removing those orb its less a cock and more of an itsy bitsy sissy clitsy !"All the men laughed while I was mercilessly railed out on both ends. Siliva and spittle ran down my impertinence the man in my lip let out a loud moan holding his rooster buried down my throat releasing watercourse after flow of hot jets of cum into my belly.

He stayed there as I continued to chock on his cum and cock. The other man firmly grabbed men around my waist also letting out a load moan, pulling me toward him as hard as he could."Oh my god what a fucking awe-inspiring ass, I going to take you up !"He shouted as I felt shot after dig of hot jizz shoot deep into my ass. He pulled back out with a pop, making my ass tactile property 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 dick from my ass as the early guy pulled out of my mouthpiece. I could experience 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 open up again, I could listen Renee talking and I knew the other voice too. I glanced over and saw Regina talking to Renee, what the sin was she doing here in New York. Ronnie walked over to my hobble consistence,"Reann, Ryan is a safe psychoanalyst, but you, god can you take a putz, Regine, gladiola you could earn it today."Regina looked appall to see the scene in the power."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 Thomas More than just the wager, how do you like the translation ?

I covered my face so as to not see her, she walked over."Ryan is that really you ? Ryan it's me Regina, sanctum poop they really did make you a woman."“ Don't look at me please Regina."“ It is you I can order, wow they did some study 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, 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 inviolable humiliation, you didn't seem to have a mellow school sweet heart and Regina appeared to be the closest thing, everyone has a damage, and we found hers to make out an old Friend with a strapon dildo. With that he slapped my ass and told the two maintenance guy 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 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 lilliputian sissy about this and take this cock !"She said as she pressed the dildo principal against my ass. This was beyond humiliating, I used to bang her and always wanted to try anal but not like this. As she pressed harder breaking the barrier of my already loose hollow she said,"Reann, remember when you wanted to try anal, well I'm about to split up 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 diameter right around the centre, or simply put, we don't expect you to get along 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 picayune cissy clit is dripping precum soft and flopping around while his huge teat just bounce around. You do neat 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 hips, she was fucking me like a wild woman while Ronnie and Renee cheered on. I could only look up at the faces as they stared in a trance at the immense 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 stomach.

"There is goes, he fucking came like the little sissy fornicatress 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 min 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 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 shtup 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 be intimate you and an extra $ 50,000 if I really humiliated you. I didn't rap her for taking the mass. 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, surmisal I know what I am doing tonight at my apartment.

The end for now !