I came from a Youngstown OH, my family was really poor growing up and life wasn’t easy. My father 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 scholarship to Ohio State I found a way out. I got a degree in math 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 little money I had from my late night working at a bar I flew out to NYC and interviewed with some small hedge 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 nervous but confident at the same time about this move. I had a few rounds of interviews with HPQ Advisors and finally I got the job as an analyst. Starting salary was $65,000 with performance based bonus. My first week Reginold, went by Reggie told me the bonuses aren’t the only way of getting extra income, Ronnie the owner likes making little bets here or there with staff.
NYC was great 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 student loans of $800 per month. Long hours, eating out and socializing left me no 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 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 other business associates talk about various topics, most of which made my stomach 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 stock in particular boy?” “Well sir Valeantz looks like a decent buy right now it is trading at 228 but my calculations show based on its momentum it could easily go to 300.” “Is that right boy, how about we bet $20,000 on that he said?” I choked on my drink and everyone burst out laughing at the 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 start dressing like a woman in the office.” He had a sinister look on his face, the other 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 need a 50% plus pull back to hit his number. Come by my office when we get back and we will work out the specifics.
I had a little bit of a bad feeling but still confident I could get that $20k to pay off my student loans as I walked into his office. I sat down in front 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 much do you owe in student 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 much 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?” “Sounds 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 friends, you will look like a woman, make up, little surgery here or there, office slut type look, we lost 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 chances the stock drops to 100, in fact make it 90 and you have to hit 275? Think about how easily you can make your life great! Deal or no deal no thinking this one over end of story.” I took a deep 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 wrong 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 similar bet and make $100K on the deal. I felt much better, I closely tracked the stock for the few months 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 news about scandal going on etc. Next thing 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 office were a few women with 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 learn 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 women’s locker room in the gym downstairs.” My heart was racing, these three beautiful women walked me to the women’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, body wash and shampoo. I took the shower and shaved everything and just stood there, my god what have I done. The woman asked me to spread my cheeks, I did exposing my rosebud, “Make sure no hair is there, now shave it again.” They weren’t joking around this was for real.
When I stepped out they dried me off and started applying makeup and put a wig on. I had a robe on and they gave me a lacey thong 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 model different clothes off the rack settling on 1.5 inch heels, a black dress with a tight white button down. He had the women leave the office and he sat on the couch. “Time to start paying up boy, hope you like cock because you’re going to have a lot of dick in your life going forward. I will make sure 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 good looking guy, to a blond bimbo in one day. With that he unzipped his pants and pulled out his member. I protested as I cried, “Ryan, no one likes a blow job where the woman is crying before they even gag. Now you made this bet and could have become rich, it was worth the bet for you and this is worth it for me. Now if you don’t hold up your end, go back home and start working at the supermarket where your mom is because kiss any other career good bye. I can easily end you and your family from any normal existence. 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 inches 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 dick. “Relax girl, slow your breathing, my cock will grow inside your mouth but I will slowly bob your head up and down nicely.” I pushed my tongue forward toward the tip and licked it. To my surprise, it didn’t taste bad, it was rather salty. I did my best 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.
“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 cock slowly growing inside my mouth.
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 hand behind my head and I felt him push down harder, his dick must have been about 6 – 6.5 inches now and maybe 1.5 inches wide. I might have 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 hands behind my head held me tight. I continued to choke, tears streamed down and saliva flowed from his mouth. He buried my face 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 head as I dodged his cock, rubbed my spit all over my face.
“Isn’t life funny, one day you’re some popular college kid banging girls the next you’ve got your head buried in some older man’s crotch while you choke on his cock and the day after that two dude are using you like a Chinese finger trap! Now take that cock again and sallow my cum before I shove it in your ass!” With that I realigned my mouth over his cock and his thrusted it into my mouth. Gagging noises followed as I fought to survive this assault on my mouth. He furiously fucked my face for about 5 minutes before burying my face 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 feet.
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 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 next month on the 15th at 10 am. Here is his card. He has a little work to do on your nothing major just a few items 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 inches to 6 inches that will stretch your ass for anal sex, please work up to these” Ronnie stood up, “Now head home kid, it’s getting late, get a good night’s rest to let this settle in.”
For the next month, I came into work dressed as a woman, Reggie just nodded with a shit happens around here kind of look. 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 but I explained the deal and he said he would have taken the deal too. I was really moody and upset, but Ronnie didn’t do anything else that was sexual. I gained a bunch of weight probably from eating and being depressed. I noticed on my calendar the Doctor’s appointment was for tomorrow.
The next morning I took my time getting up, showered, got ready and put on my blonde wig for the day. I arrived at Dr. Regarios office at 10 am and filled out a bunch of paperwork and consent forms. I was called into his office. He reassured me everything is reversible, per Ronnie’s order there was a little work he wanted but nothing major. I didn’t even want to know what he had in mind. He laid me on the table and gave me some gas as I slowly fell asleep.
I awoke in an awful amount of pain, dazed and confused as to what just happened. “Ah our patient is finally coming too.” Dr. Regario exclaimed. I slowly tried to sit up, my face hurt, my chest hurt, my ass hurt. As I looked down there was something on my chest blocking some of my view. “Ohhh my god, what the fuck 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 orders paid for from Ronnie your boss, along with several 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 lifts, 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 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 hormones you were taking really helped in making your tits 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 call’s, a sissy clit left that can’t produce sperm. And all these documents here protect me, you should read more carefully when betting with Ronnie.”
Oh, my god, they cut off my balls, 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 lobby 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 nothing just sat there crying. “Ryan or Reann, take the next month off for recovery, Ronnie has deposited $50,000 into your account to console you. Take it easy, we will send food 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 word as I walked in with bandages and the obvious transformation.
About a month later I got ready for work, I really did look hot, huge tits, fat ass, big lips, small waist everything. My cock used to be around 6 inches now barely 5 and skinny when hard. The DVD was fully of sissy sex and hypno, I used my dildos and butt plugs. For some reason the dildos really made me cum and regular porn did nothing, probably the pills.
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 lips out.” He said as he undid his pants. I walked over and got on my knees, I took his cock in my mouth and bobbed up and down slurping this time taking it all no problem. “Someone has been practicing I see. God those lips make it so much better” because of those lips drool was sliding out around his cock and running down my face.
Right 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 stop honey! Hey you two stay a while, isn’t she pretty, this is Reann, remember the young guy that works here this is him after surgery.” He just keep pumping and a few moments later he pushed my head 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 accent they said, “Holy shit Ronnie, this was that young new guy, my god you gave him the hottest set of tits an ass I’ve ever seen on a chick, let alone a dude. I’m not gay, but fuck that ass looks juicy as hell and those lips were built for sucking cock.” Ronnie looked to them, “don’t worry it’s only gay when there is a cock in your ass, Reann is the only one in the room that will have one up her pussy!”
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 pants when two fat cocks plopped out. My mouth dropped and I looked at Ronnie, “But they are too big?” “Not for my little 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 bent 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 mouth, 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 cock!”
As I looked up I thought to myself how is it the short guy has the biggest cock. It was hard maybe 10 inches and as thick 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 pain and pleasure while trying to survive the cock in my mouth. 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 cock head at my ass, I tried to protest, 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 pain again silenced into the other man’s crotch as I tried to squirm. A wave of humiliation, pain and pleasure 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 white piece 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 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 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 sight, your cocks are impaling this little girl on both ends like an accordion! Why don’t you lift him up?” With that I tried to protest but nothing helped, they lifted me off the desk and flipped me upside down rotating me in midair, I tried to kick and push a little but they clamped my legs down under the man’s armpits and locked me in place, the short guy lined his cock 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 look at his little cock bob around, after all those hormones and removing those balls 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 spit ran down my cheeks 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 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 amazing ass, I going to fill you up!” He shouted as I felt shot after shot 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 yelp. “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 feel 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 again, I could hear Renee talking and I knew the other voice too. I glanced over and saw Regina talking to Renee, what the hell was she doing here in New York. Ronnie walked over to my limp body, “Reann, Ryan is a good analyst, but you, god can you take a cock, Regine, glad you could make 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 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 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 ready and Regina was stripping down.
“Reann, to really break 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 price, and we found hers to fuck 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 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 woman 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 but not like this. As she pressed harder breaking the barrier of my already loose hole she said, “Reann, remember when you wanted to try anal, well I’m about to split you in half my little sissy.” With that she pushed her 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 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 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 little sissy clit is dripping precum soft and flopping around while his huge tits just bounce 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 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 huge dildo ripping my ass up. “Oh gawd, oh gawd,” I yelped out as I felt like I was about to erupt when all of a sudden my cock started to let out a stream of cum like a faucet, it pooled all over my stomach.
“There is goes, he fucking came like the little sissy slut he is, only cumming from now on with a nice firm cock up his ass!” Renee exclaimed. Regina kept fucking me for a few more minutes as I bucked around in pure ecstasy. It was too 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 fuck 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 fuck you and an extra $50,000 if I really humiliated you. I didn’t blame her for taking the deal. She felt bad but a bets a bet and she missed the old me. She did want to fuck me again, she said it gave her a lot of 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!