The things we do for money

This is my first time writing this style, I am open to any criticism that could help me improve :) 

“Again? You promised you wouldn’t miss our anniversary this year” he said frustrated. “I know baby I’m sorry! I really can’t do anything about it” I told him, “The shareholders need me in this meeting. I will fly back home as soon as I can” “Fine, but I’m not spending another anniversary alone, I’m going out”.

We hung up and I head into the room, wondering what I could’ve changed to avoid being here today.

It all started 5 years ago, when I got the brilliant idea of starting my own company. Al was very supportive, he encouraged me to pursue my dreams and go for it. But a year later, and more than 100K invested, how could I tell him that my dream company was bankrupt? I couldn’t disappoint him. I had to do everything I could to make it work.

You might think it would’ve been better to accept defeat and walk away with a 100k loan, you would be right. But I am not that kind of person, so when an old friend, Jeff, offered to invest and pay off our loan, I accepted all his terms.

It started off with simple requests, attend dinners with him, explain the company strategy to other potential investors, and try to raise funds. Basic business requirements. Then these requests started escalating, attend business trips, travel to meet clients, be present in every single meeting, etc. That was when I started missing milestones in my personal life. I was away on business for Al’s 40th birthday, I was in Japan for our 10th anniversary, I had a very important meeting that made me miss his brother’s wedding, and so on.

One day, Jeff asked me to attend a dinner with him; he was meeting up with his ex and his new boyfriend and didn’t want to go alone. He said that if I did him that favor, he’d look into increasing his investments. I had nothing else to do, so I figured it was a smart decision. He kept asking for small favors, and I kept accepting.

But Jeff didn’t stop there, his requests became harder to satisfy until one day he asked me to sleep with him. I told him it was out of the question, and that I would never hurt Al like that. What made it even weirder was that Jeff and I were both tops; we had fooled around once, a long time ago, we helped each other jerkoff, but that was the end of it, because neither of us would bottom for the other.

That was the day everything changed. Instead of taking no as an answer, Jeff threatened to walk out. I couldn’t afford to lose him as an investor, he was the only thing keep my company afloat. I struggled to come up with a solution and ended up rejecting his request but offering to jerk him off. He accepted. That night, he called me into his hotel room.

I arrived and he was in his robe. He requested I strip naked, and I complied. He then asked me to remove his robe, revealing his naked chubby body. He had let himself go pretty bad. His hairy chest was kind of sagging, and his belly covered his flaccid dick. He instructed me to drop to my knees and start stroking him, “get me hard” were his exact words. I complied, dropping to my knees and reaching out to search for his dick, hiding within his belly fat. It wasn’t long before his dick made its appearance. If there was one thing nice about Jeff, it was his dick. He has a beautiful 9.5-inch dick, cut, with a perfect mushroom head. Any bottom would love to be taken by that dick; except I was a top. I found myself rubbing his cock with both hands while it stood straight ahead, looking at me, as if forcing itself into my mouth. My flaccid dick unchanged, I could feel the excitement run through Jeff. I felt as if I was being used, bought even. I continued to rub his dick, trying to imagine myself anywhere but in that place. I managed to escape, imagine myself with Al, rubbing his cock while he blows me. I felt at ease, I felt safe with my husband. The minute I start to get horny, I was pulled back into the nightmare that is my reality as Jeff’s dick blows all over my face. I opened my eyes to see my hard cock standing between my legs as Jeff’s cum drips from my face onto my muscular chest. The sight of Jeff again forces my dick back into its sleeping mode. I stood up and asked for a permission to leave, he accepted.

I headed back to my room, disgusted by what I just did, wondering how I will be able to look Al in the face again.

The next day, I met up with Jeff to tell him that I had changed my mind. That nothing he could say would let me do that again, and that if he wanted to leave, he should.

To my surprise, he tells me that he’s staying. We spent the day in meetings before we headed back to our hotel. Once there, he asks me to join him in his room. I respectfully decline, telling him that I would rather stay in my own room, but he insists, saying that he had something he wanted to show me.

When we get to his room, or should I say suite, I sit on an armchair in hopes of keeping as much distance between Jeff and me. He pours himself a glass of single malt, circles through the room for a few minutes, and then comes back and lays on his couch, legs spread. In one hand a cigar, the other the glass. I remain staring at the door the whole time.

“Suck my cock” he requests as he widens his legs even further.

“I told you I’m not doing that again, Jeff. If you want to leave, you can, but I’m never doing anything like that with you, ever, again.”

“I think you’ll change your mind” he says as he gestures to the TV in his room. I rotate to look behind me and see a clip playing on his TV. It takes me a minute before I realize it’s us. He had recorded me jerking him off and has a short clip playing on repeat. The video shows me with my eyes closed, smiling as I rub his dick. My dick standing between my legs. Horrified at what I just saw, I scream at him “You sick son of a bitch you recorded me?”

He replies with the smoothest tone ever “Come on now, be cool, I’m not going to show it to anyone.” He pauses for a few seconds before he adds, “Well, I won’t show it to anyone if you blow me. If you don’t, I’ll have it mailed to Al” “You’re blackmailing me into sucking you, you sick bastard?” “Well, I would put it more as I’m incentivizing you to do it. Afterall, I saved your life with my investment, you should return the favor”

Appalled by Jeff’s statement, I start heading to the door saying “I’d rather you send it to Al than suck your dick”

Just as I reached the door, he says “What if I gave you 3k, and cleared your schedule for two weeks? You’d be able to spend time with Al and finally go on one of the trips you promised him you two would have once the company was afloat”

The thought of finally being able to treat Al the way he deserves travels though my body as I think of the places we could visit with 3k. “No thanks, I’m still not interested” I answer him, re-evaluating what I’d have to do earn that trip.

“10k” he says

Disgusting, I think to myself as I decide to leave. But I feel my body circling back to face Jeff, defeat showing on my face as I drop to my knees.

I unzip his pants and slide his flaccid cock out. His belly still tucked in his shirt, I start to jerk him off. Within seconds, his dick hardens in my hand and reaches its full size. “Suck it” he says. I abide I bend forwards. My lips reach the tip of his dick. I hate every second of it as I start to suck the tip of his cock. His gaze focused on me, I continue to suck him. He instructs me to unbutton my shirt while sucking his cock. I obey, realizing I can fit more of his dick in my mouth than what I had imagined. Once topless, he sets his whiskey glass aside and starts playing with my chest. I’m extremely fit, I’ve been working out since I was 20 and I never missed a day, be it business trips or other. He circles my nipple with his hand, and I feel myself hating every moment of it. My lips still glued to his thick cut dick, my nipples start to harden. I feel ashamed as I think about Al and what he would do if he knew I was giving Jeff a blowjob. Jeff continues to play with my chest as I take my pants off, at his request. I am surprised to see my hard dick fighting with my boxers as my mind focuses on the level of hatred I pile up towards Jeff. Jeff looks at my boxers, instructs me to take it off, and then plan with my dick. I obey, hating him even more as I stroke my hard dick.

As per his usual, Jeff blows his load in my mouth without notice. I feel a warm gush of his cum fill my mouth before dripping out on his pumping dick as I continue to stroke my dick. He takes his hand away from my chest and holds my head from the back, forcing his dick into my throat as he continues to blow the rest of his loads. I feel myself punished, choking on his thick cum as my hard dick blows on Jeff’s ugly legs. Once he finished, Jeff releases my head and I cough, trying to breathe while fighting with his cum in my mouth.

He doesn’t mention it, but I could see his eyes lighting up with questions, wanting to ask if I enjoyed it, wondering why and how I came. Instead, he stands up and heads to his shower. I pick up my clothes and start walking to the door as I dress myself, swallowing some of Jeff’s cum and wiping the rest off my chin. I drop my head to the floor as I walk back to my room, feeling ashamed I was able to cum.

I get to my room and sit on my bed; not wanting to talk to Al after what I had done. I stay there with the lights off, afraid to catch myself in the mirror, afraid of the horror I might feel if I did. I did not want anything to validate what I had just done. I contemplate my life and how I ended up here, wondering if I should’ve seen the signs all along. I drift into a spiral journey of thoughts and possibilities and end up crying myself to sleep.

But things didn’t end there.

Jeff’s requests that I blow him multiple times again, each time offering another 10k. I thought that if I do it enough times, I’d pile up a 100k and be able to pay him back all his loan, and never speak to him again.

And there I was, talking to Al.

“Again? You promised you wouldn’t miss our anniversary this year” he said frustrated – As he should be, if only you knew what I was doing during our anniversary you’d leave me.

“I know baby I’m sorry! I really can’t do anything about it” I lied to him,

“The shareholders need me in this meeting. I will fly back home as soon as I can”, and by shareholders I mean Jeff, and by meeting I mean blowjob, and by soon I mean 5 more blowjobs, once I have earned the full 100k and I can forget this nightmare ever started.

“Fine, but I’m not spending another anniversary alone, I’m going out”. As you should my love, at least one of us should be enjoying this.

But my luck was about to change. For the better or worse? Depends on how you look at it. I reach Jeff’s suite for his 6th blowjob, my 6th 10k, wearing the underwear he had gotten me. I was shocked when I opened it. He got me a black jockstrap with a very wide waistband. Very tight on my dick and almost nothing from the back. With that, a leather harness with a buckle from the front and two from the back.

I open the door to see Jeff waiting for me. I lose my robe, revealing his twisted gift around my body, and head up to him saying “let’s start” as I drop to my knees. He catches me by the harness and pulls me back up.

“Not this time” he said as he gestured me to stop. “Today I’m fucking you”.

I feel a shockwave travel through me as I start to sweat. “Don’t worry, I know this is not what you had in mind, so I’m willing to give you more. I’d give you 50k. I’m not a fool you know, I know you’re saving to pay me back, so I’ll make it easier. I fuck you once, and you’re free.”

I feel a spark of joy lighten through me as I see the light at the end of this horrible tunnel. I imagine what it would be like to finally be free, to not have to be Jeff’s slave anymore. One thing I need to do and I’m free for good. I suffer once as that man violates my ass, and I get to walk away.

“Ok” I say as I move to the couch, looking at him for instructions of what I should do.

“Come on, you really think I’d take you here on the couch?”. He guides me to the bedroom and lays me on the bed. He walks to my side and take my hand in his. “I need to make sure you won’t change your mind” he explains as he handcuffs me to the bedframe. He squeezes the cuffs tight on both hands, leaving my legs unchained.

Jeff strips naked before climbing on the bed and lifting my legs up in the air. I start to panic as I realize he’s going to fuck me raw. “Don’t worry, you’ll get used to it” he says as he lubes his dick and starts inserting it into me.
My hole burns as his thick dick penetrates it. I fight with my cuffs to push him away but only manage to feel the pain on my wrists. Anxiety takes over me as I realize I was getting raped. I pull harder on my cuffs without any results.

Jeff’s dick destroys me, the cuffs making their mark on my wrists, the harness tattoos me with a print of its shape. I feel used.

That’s when my dick starts hardening. I feel confused as pain rushes through my body. I can’t grasp which area hurts more, my wrists, my ass or my torso. But for some reason, it gets me hard. I feel a fourth pain area arise as my hard dick discovers the chains it is in. The jockstrap has my cock in a locked position, tightening more and more as my dick rises. I lose common sense as I feel myself enjoying the pain. Jeff continues into me, spreading my tight hole more and more, hurting me, destroying me, and my dick’s reaction is to grow harder.

Once fully in, Jeff grabs my hidden dick with his hand and uses my crotch as a stabilizer as fucks me. My ass still in pain, I feel Jeff’s huge cock plowing it. I fight to get free and my chains resist, amplifying my pain. I feel the urge to play with my cock as my whole body aches. Failing to understand what was happening, I start begging Jeff to fuck me harder, to destroy me even more.

But he stops. Jeff pulls out and uncuffs my hand from the bedframe, only to cuff it again on the other side of my other hand, forcing me to rotate on the bed. Lying face down, I crawl into an upright position only to feel Jeff’s hand forcing my face down, locking me into a dog’s position, on all fours. With one move, Jeff inserts his dick back into me smacking my head on the board in front of it. To avoid giving me a concussion, he holds me by the harness as he continues to ruin my internals organs with his dick. I feel his every plow as my body is forced forwards, but held back by his tight grip. I feel a new pain in my shoulders as the harness is pulled harder. My swollen dick still fighting with the fabric, I beg Jeff to take it out. He refuses, telling me I don’t deserve to have my cock freed.

The pain in my ass subsides as I start to enjoy the fucking. Suddenly, I feel a jolt of electricity travelling through my body as my dick shoots its load in its fabric prison. I moan as I cum. I feel my ass needing to close, as if it was done for the day. Instead of stopping, Jeff continues to pound me. The pain in my asshole rises again as I beg Jeff to stop, telling him I came and that I was done. He refuses to answer to me and continues raping me, stating that he won’t stop before he fills me with his juice.

I feel the hate rising again in me and my dick mirrors my feelings. For some reason, I feel my dick hardening as it blends the cum it was surrounded with. Jeff’s hand still on the harness, I feel his other one grabbing my crotch so tight that cum oozes out of my jockstrap. Happy with what he found, he blows his load deep inside me as he continues to bounce in and out of me. The warm feeling in me entices my dick to replicate and I feel myself blowing another load into Jeff’s hand, forcing more cum to drip out my underwear.

Jeff continues to fuck me as he drains his cock into me before he takes it out and shoves a few fingers in my hole. He takes his fingers out and forces them down my throat, forcing me to taste my own ass mixed with his fluid. I feel myself relax as I enjoy his torture.

Jeff gets up and walks to his shower without untying me. It takes him about 15 minutes to shower as I stay in the same position I am in, unable to move. After he’s done, he comes back out and releases me from my chains, ordering me to leave.

I exit Jeff’s suite and head back to my own room to clean myself. Instead of disgust, I feel aroused and confused; wondering the whole time what had just happened.