Willing to do anything

Disclaimer: all characters appearing in this story are fictional and are 18 or older.

My name is Nate and this is my story.

You ever hear the phrase 'young and dumb'? Well, that has been me ever since I turned 18. I was the thin loner guy with a couple good friends in high school. I guess they would describe me as quiet, but there were a couple instances of some things I said being transphobic or homophobic, but nobody seemed to care at the time. They never really noticed me that much, and I was glad, since all I ever wanted was to leave that place.

When the time came, I bolted out of that place without the slightest of a goodbye. It has been about 10 years since that time and now, as corny as it is, I wish I could go back.

When I left my folks, I found a job at a casino as a blackjack dealer. It was long hours and I had to work weekends, but the tips were good. After a while, I picked up how some players were counting the cards. It never bothered me, I wanted them to win, since that's when I made the most money.

The dumbest decision of my life was driving fifty miles away to another casino to try it myself. I had a couple thousand on me that night, and let me tell you, I had never seen such hot hands like I did that night.

I walked out of there with FIFTY GRAND! Not only that, but I felt like I was the best player who had ever walked on this fucking earth. A really slutty girl at the place came by and let me know I could buy her some drinks with my winnings. I fucked her all night. It was what I thought every day of my life would be like from then on.

The next day I was hung over, but I thought I would cool it for a week and then hit another place hard and fast on the weekend. I lost ten thousand bucks that time.

I figured I just had to practice and watch more. I just kept gambling. Some weekends I would bounce up fifteen or twenty grand and others would crash me back down. I never felt more alive than when I was waiting to find out if I had won or not.

Eventually, this story turns out like all the others. I lost all of that fifty grand, all of my life savings, my car, and anything I could hock for a buck. That's when I made the next worst decision of my life. Double or nothing! I just needed someone to loan me some cash, and I knew that I would be able to get it all back.

I found this back ally guy that spotted all the pros when they required it. He lent me sixty grand, which I assured him that I would be able to pay back with interest: seventy grand in four weeks. Well, no surprise that I lost it all in three weeks.

I had one week to go, and he stops in to see me. I asked him if I could get an extension on the time. He looks me in the eye and says, 'If you don't have the money, I will sell your body parts one at a time until I make it back. No exceptions'.

I was scared shitless. I know he could maybe take a kidney and get some of it but fuck! Seventy grand! He would need a kidney and a heart to get that. This guy was bad news, I knew I was a dead man.

I looked through all my contacts and as it turned out Barry, my old friend I went to high school with, had actually made some sizable money. I guess he jumped on the crypto at the right time, and he cashed out in the millions. He started his own business and was really successful.

I called him, and he actually invited me over to his office to catch up. I was nervous, but just as much, I hoped and prayed he would be willing to pull me out of this shitty mess I made.

I took a deep breath outside his office. His staff had let me in and guided me to his office. Usually he would have a secretary do that, but she had just resigned recently. I pushed the door open and there he was, and he looked like the kind of guy that had money. He had the fancy clothes, the big office, cigars, and expensive furniture all over the place.

"Is that you, Nate?"

"Hi Barry. Long time no see. What's it been? 10 years already?"

"Fuck man. Don't tell me that. It feels just like yesterday. You know, I am surprised we lost touch after school. I hoped we would stay in touch. Anyway, you reached out to me. What's going on? How have you been?"

"Um. Well, it's been a bit of a roller coaster for me."

Barry jumped in. "Yeah. Life's a bitch sometimes, ain't it."

"Uh. Yeah. So anyway. I'm sorry that I let our friendship fall through the cracks. I am even more sorry for why I am here." I trailed off and looked down in embarrassment.

"Oh". Barry sounded upset, realizing this wasn't going to be the cheerful catch-up he thought it would be. "So you are just like everyone else, huh? You saw that I did something for myself and you want a piece? Is it a job? It is money? What do you want, Nate?"

I told him the story of how I got myself into a gambling addiction and how I have a loan shark up my ass for my borrowed debt. I told him how I was physically threatened, and now I feared that I could lose my life if I don't pay up.

"So I am really sorry, Barry, but I am grasping for a lifeline here. I'm truly willing to do anything, and I hope you can see I am genuinely just asking for help. I don't expect you to help me for nothing, but I just need a chance."

Barry sat down, and the room fell silent as he considered his options. My heart pounded in my chest, hoping that by spilling my guts here, he might have some compassion for me for old times sake.

"You know, Nate, you were once a really good friend."

I winced. That did not sound like a good way to start this.

"I took some chances that paid off and made me the man I am today. What you have done is taken chances as well, but clearly they have been misguided and led you into some trouble. I wish we could have just stayed friends. I would have given you advice and it would be so much better helping a friend. Look Nate, that didn't happen, and you are just a stranger to me that I used to know. I hope you can understand"

"I know Barry." I felt so defeated. No bank would lend me money with my piss credit, and everyone else I knew didn't have any kind of scratch to bail me out. This felt like the end of the line.

"That being said, I still feel like there may be an opportunity here if you really meant what you said when you claimed to be willing to do anything. I would never offer this proposition to a friend, but if you are willing, I may have a solution.

Tears welled in my eyes as I realized he would offer me a lifeline. "Yes man! I am willing to do anything. This is life or death, and right now anything is better than death."

"That is a relief to hear Nate. Let me cut to the chase, as there is something about me that I have never shared to anyone other than a few lovers in confidence. You may be aware that I am publicly bisexual, but that is really a mask to disguise what my true fetish is. What absolutely turns me on is when I make someone agree to do something completely out of character. For instance, I would cream my pants if I sat down with a vegan and for let's say ten thousand dollars they agree to eat an entire cooked chicken. Do you understand?"

I had a bad feeling in the pit of my stomach. "Um. Yeah, I think so. Does this have to do with your proposal?"

"Yes. Very good Nate. Most of my lovers leave me because I push them to do things they don't want because of my desires. Even the most nasty gold diggers eventually leave me after I push them too far. That's why with your situation I think you are perfect to stand in because you need this so much."

"Well... That's true" I agreed. "But what did you want me to do?" I was nervous about his answer.

"When we were in school, I remember you making deeply hurtful comments that made the school label you as transphobic and homophobic. You can see now, since I have announced my sexuality, that these comments actually hurt me. I buried my feelings for the sake of our friendship."

"Barry. I didn't know. I never would have said those things if I did."

"I know that, Nate. I don't mean to suggest that this is revenge, but only to say that you are very uncomfortable with trans and gay people. My proposal would be that I will pay your bookie in full tomorrow before your deadline, in exchange you sign a contract with my legal team."

"What's in the contract?"

"You will agree to live as a trans woman for the length of 1 year. You will work as my personal secretary and attendant. You will on occasion be expected to be my lover and tend to my sexual needs. I will house you in your own quarters and will additionally pay you a living wage plus a stipend to spend on all items and clothes to live as a woman. You will be under no circumstances be allowed to revert to appearing as a man during the 1 year. If you fail to honor the terms of the contract you will be penalized a debt to me of $70,000 which a court of law will enforce."

"Fuck Barry! You want me to be your Bitch?"

"Well, that's one way to put it. Yes. I think you will grow to have a new-found respect for the LGBTQ+ when this is over. Additionally, you will be granted an option to continually serve the terms of your contract indefinitely at the conclusion of 1 year with an increased wage equal to the initial debt annually."

"Fuck dude. I don't have any other options! I am going to have to do it. Fuck! You want me to... ugggh" I almost vomited on the floor. "...to Have sex with you as a woman?"

"Nate, you will be required to pleasure me with your hands, your mouth, and your ass. I need you to know that this is required. You will be paraded around like a little fairy princess cocksucker. On the bright side, no one will be after your body but me." He winked after that last bit.

"Ok. I guess this is what it takes." I sighed and was ready to cry in my car.

"Nate. I am glad you agree this is the better alternative, but I need you to prove to me, you are willing to follow through."

He walked over to a wardrobe in his office and pulled out some clothes.

"These clothes were left by one of my gold digging slut exes. There is a pink thong, a matching push-up bra, a mini skirt, and a see through white sleeveless top that will expose your midriff. I also have a pair of black heels that match the skirt and some red lipstick. I want you to take off all your clothes and put this and the lipstick on. Furthermore, I want to introduce you to my staff."

"I don't want to do that. All those people saw me come in. You said I would sign tomorrow."

"Nate, all my lovers were not willing to commit to it. I need you to prove to me, you are worth this investment. Today is a trial run. Think of it like an interview. I just can't agree to this unless you give me some reason to."

"Fuck!" I shouted. "Fine, I will wear the fucking slut clothes."

"That's a good girl" He said as he smiled.

"Do you have a bathroom, or somewhere I can change?"

"I want you to change in front of me. I am excited to see you wear panties for the first time. You are going to be such a pretty little cocksucker."

His words stung as they were spoken. "Oh my God, Barry. This is fucking weird." I started taking off my shirt, shoes, socks, and pants until I was just in my boxers. I stopped and hesitated. I really did not want to be naked in front of this rich creep.

"Well go on" he urged.

I just bit my tongue and pulled down my boxers, fully exposing myself to him.

"Oh my" he whispered to himself. "I didn't think it was going to be so small"

"Fuck you!" I shouted.

"Nate, if you are going to be a lady around here, you need to watch your language, or you might violate your future contract. OK?"

Barry was really getting on my nerves. I didn't want to compromise the deal, so I just frowned and then nodded. I pulled out the pink thing and held the delicate feminine panties in my hand. I gulped, I couldn't believe I was about to put this on and become the thing I used to openly mock.

Barry stepped out in front of his desk. It was now evident he had a huge erection and that this was his pleasure. He really wanted to get up close and savor the moment when I caved to his demands.

I closed my eyes and stepped each of my legs into the small openings. The fabric rubbed against my leg hair as I pulled them upward. They were stretchy and very tight as they reached closer to my waist. I pulled my balls and penis forward, so I could get the thong all the way up. They were nestled into a bulge in the front, while the back of the thong split my cheeks and sunk into my ass.

I wanted to cover my face. I must have turned bright red, and I could only look down. I really did not want to see how much Barry was enjoying the little show.

"Nate, can you do a little twirl, so I can see all of it?"

I turned myself in a circle. With nowhere to hide, he had full view of the emasculating scene unfolding in front of him. When I had fully turned around, he had his hand on his protruding bulge and he was biting his lip. I wanted to hurl all over his expensive clothes. I questioned if this was better than the gruesome death I was promised.

Barry continued to prompt me further, all the while savoring every moment. He would stroke his penis while never averting his lustful gaze.

I struggled to get the bra on. I thought he would offer to help, but the more I struggled with the clasps, the more he seemed to enjoy himself, occasionally letting out a little moan. I did eventually get it on and felt awkward wearing a device for body parts I was clearly lacking.

I got the skirt on and was glad to have some covering, but quickly realized that any bending over would flash anyone a glimpse of the panties I was wearing. There would be no safety in the skirt. The top felt so small. It made me feel more naked than when I was just in the panties. It barely covered the bra and put my stomach and arms on display. Since it was see through, everyone would see my bra.

Barry was heavily moaning by this time. "That's such a good look for you, Nate. Mmmm. I knew you would be my naughty little girl. Go ahead and get your shoes and lipstick on."

Again I struggled to get my mannish feet inside the small and strap covered heels. Once I did manage, I felt wobbly. I feared that I was going to fall and expose myself about every moment I wore these clothes. I grabbed the lipstick and clumsily applied it. It probably looked like a clown job, but Barry didn't seem to care. He loved every second. What a pervert.

"That was perfect, Nate. I think you have proven that you are willing to play ball. Before I can run you around the office, I have a little problem that needs taking care of. That dress up was hot and well I don't really want to walk around the office with this hard on. So I will tell you what. I want you to give me a blow job and when we sign the contract tomorrow, I will consider today as a day credited towards your year, instead of a test. You are going to have to do it anyway, so you might as well benefit from it now."

"Uugghh" I gagged. I had no time to prepare myself for this nonsense. I was going to have to commit to this year deal, and he was right. If I was going to do it, I might as well have it count. "OK" I managed to squeak out.

"I want you to tell me that you want to suck my cock. I want you to lick your lips and pretend that this is your horny girl treat. Tell me how much you want me and how bad you need it. Then I want you to lick it and kiss it before you suck it. Look me in the eye and swallow every drop like it was your favorite meal."

"Mmmmph." I wanted to fucking scream at him. He wants a bimbo cocksucker, and I guess that's me.

"Barry... I want to... Uh... Suck your... Um... cock." I tried to force it out, and tears began to form as I braced for the oral sex I was about to endure. I licked my lips and tasted the lipstick, reminding myself how fucking idiotic I must look.

I got on my knees since I was afraid to walk in the heels and started to crawl towards him. "I want your... cock, Barry. I am such a horny... Uh... Slut. I need to get some dick. I want you so bad. Please let me taste your cock."

He was about bursting out of his pants by the time I was close enough to smell his musk. I unzipped his pants and guided his dick through his boxers until it sprung in front of my face. He was huge. It was the biggest I had ever seen in person. Probably seven or eight inches, and it just looked massive compared to mine.

I felt so dirty and slimy touching his penis, and my mouth felt dry thinking about touching it with my lips. I began to have my tears roll down my face when I puckered my lips and kissed it.

I repeatedly kissed his penis from top to bottom as his pubes poked my nose. I stuck out my tongue and ran it the entire length. Barry moaned, "Yes, Nate. MmMm" I opened my mouth and slowly inserted his dick.

He tasted salty and I instantly gagged with only his head in my mouth. "Don't stop" he urged me. Barry pressed his penis forward until he reached the back of my mouth. I looked up at his face and he was making faces of such pleasure while I continued to cry.

I rocked his penis back and forth in my mouth. He was so turned on that it did not take very much time until his moaning turned into shouting. "Yes! Oh, Nate! Mmm. You are such a cocksucker. Slut! Oh yes. I'm going to cum!"

I braced as his penis began to throb inside my mouth. Then came his cum. It was thick and hot. I had never wanted to spit so much in my entire life. This was wrong, and now he had made me a cocksucker. I finally forced myself to swallow the putrid cream and muster a weak "Thank you".

He zipped up his pants and regained his composure. "You know, Nate, I think this is the beginning of a great year."

I was not lying when I said I was willing to do anything to get myself out of my debt. Now my life would be filled of embarrassment, a horrific new lifestyle, and a man that would push me into my deepest nightmares. I questioned if this was the right choice, but I was desperate, and now I had to pay the price for my stupidity.