The Business of Being a Man Whore

"Ummm...I...help," Aubree said, looking around. I heard the sound of a slow clap coming from around the corner. Eventually, Principal Locke emerged, looking smug but disappointed.

"Well played, Darrell. It seems I underestimated you. You saw through this ruse I put together the second Aubree started talking, didn't you," she asked. I had no clue what was going on.

"I know you think you have been extremely subtle and clever in trying to keep your personal prostitution business hidden from me. Using code words, having runners pass on information to clients, and taking advantage of every tiny loophole in school policies. Any other principal in this country would have never realized you are using the school for your whoring business, but unfortunately, you have a principal with the greatest investigative skills. I saw through all your deceptions, redirects, and red herrings," the Principal said proudly.

I didn't understand what she was talking about. Instead, I admired the flier I put up on the wall behind her that read, 'Darrell will have sex with you for money,' and included a drawing of my penis with its actual proportions and size. I was able to fit the drawing on the piece of paper very easily.

The Principal continued her monologue. "I thought I had you trapped. I bet everything on this ruse with Aubree. All I needed to happen was for you to agree to take her money for sex, and I would have you. But you saw it coming. We were playing 4D chess, and you turned my check on you into a checkmate against me. Aubree, you can go," she said, waving her hand at the student.

Aubree's face was bright red. "I'm... sorry and confused, Darrell," she said before running off. I thought she wanted me to take her virginity. Oh well, I'll check with her later.

"So here we are, just the two of us. I appreciate the situation I am in. You just witnessed me force a student to proposition you for sex. If the school board were to get wind of this, my career would be over. You have 100% leverage over me, Darrell. How will you use it," she asked. Suddenly, I realized what was going on. The Principal wanted to purchase my services.

"It's 200 dollars for sex. That price is firm, just so you know," I explained. I thought about pointing her to my flier but figured this was easiest.

"You bastard. You would have me both pay you money and have sex with you for your silence," she asked shocked.

"I can be as quiet as you like. Usually, the girls are the ones who make the most noise," I added.

"In my five years as Principal of this school, I have no less than four dozen students try and blackmail me into sex. All unsuccessfully. Not counting that role play my boyfriend and I did. But I see now that streak is at an end. You win, Darrell. You will have your money and my body," she said, looking at the ground, defeated.

Suddenly, I realized I was being an idiot. I forgot to upsell the add-ons. "I also offer a variety of options like for another 20 dollars, we can have unprotected sex where I try and get you pregnant."

Principal Locke looked up in horror. "You dare raise the price? Right after, I agreed to your initial deal. And now you are insisting I let you cum inside me? I'm not on birth control, and despite what all the graffiti says in the girl's bathrooms, I can still get pregnant." It was interesting to hear about the graffiti in the girl's bathroom. The words 'Principal Locke gives bad head' are written everywhere in the boys' bathrooms.

"But I see I have no choice, and I agree to your terms. But this is it! No more changes to the deal. Now follow me. We can do this in my office. I have a strong desk that can hold up to four people on it, unlike my last one."

I followed the Principal to her office. Before heading in, she informed her secretary. "I'm not to be disturbed, understood? I have an important matter to discuss with Darrell. You might hear me yelling, but it's nothing to worry about," she instructed.

As we walked into the office, I could hear the secretary mutter, "New boyfriend, same old role play."

We entered the office, and she closed the door. From her purse, she handed me 220 dollars as agreed. She started to unbutton her shirt. "I hope you appreciate that seeing my naked body is a highly sought-after sight in this school district. Hundreds of parents, teachers, school board members, and students would pay a lot of money to see what you are about to," she said as she pulled her shirt off, revealing her fancy-looking bra.

She paused and gave me a distressed expression. "You fucking bastard. I can tell what you are thinking just by that look. You want to take pictures of me as I undress as part of our deal, don't you? I don't have a choice, do I? Fine. Take out your phone and snap all the pictures of me you want as I get naked. But so help me if any of these get leaked..."

I did as she instructed and took pictures as she removed her skirt. This was yet another add-on I wasn't expecting women to want. I wouldn't charge Principal Locke for taking pictures of her stripping, but the next girl who wanted me to have nude pictures of them on my phone would need to pay the fee. She reached behind her back and found her bra's hook. "Believe it or not, but when I became an educator, I had made an oath to myself that I would never let a current student of mine take pictures of my naked tits. How naive I was," she said, letting her bra drop to the floor.

I continued to snap a lot of pictures. I was annoyed thinking about how much storage space this would take on my phone, and I wasn't even getting any additional money for doing so. The one upside, though, was I could see my hot Principal's naked body whenever I wanted though.

The topless Principal stood in front of me, looking nervously at her panties. "Do you really need to get photos of me fully naked, or is this good enough," she asked while getting red in the face. This confused me as she was the one who asked me to take pictures of her stripping.

"Principal, that's entirely up to you," I replied.

"You're right. And I made that choice when I sent a naive virgin to try and talk you into fucking her for money. I won't make that mistake again, but for now, I need to pay the price," she said and then pulled her panties down. I took a large variety of pictures of her naked body and various angles and zooms, hoping we were just about done. "I'm assuming you want me to pose for you as well," she said. I guess we aren't almost done, I complained in my head.

The Principal had me get shots of her rubbing her tits, bending over, licking various objects in the office, slapping her butt, leaning up against the wall, and many more. This was taking forever. Eventually, she got on her desk and spread her legs wide. "Enjoying this view, bastard? I'm sure this is giving you more ideas. You'd like to see me pleasure myself right here and now? And you probably want to record a video of this. Fine, just do it," she complained while starting to rub her pussy with her hand. Now we are recording videos, too? The Principal had a talent for creating add-ons I don't have prices for.

I started recording her and was impressed by her skills with her hands. She was fingering herself and rubbing her clit with the same hand while her other hand played with her nipples. It was then I realized I forgot to charge her for masturbating in front of me. Damn it, this sucks. Her tongue stuck out of her mouth as she was nearly drooling from the self-pleasure she was experiencing. Panting like a dog, she opened her eyes and looked at me. "You're going to share this video with all your friends, aren't you? I'll be the inspiration for a lot of teenage orgasms in the near future, won't I? You're such an asshole for turning me into a porn star to the school. So many hard cocks looking at my soaked pussy..." Her face then contorted, and she yelled out, "CUM WITH ME, MY STUDENTS!"

She then collapsed onto the desk. While catching her breath, she told me, "Only share that with students 18 and older, okay?" I was so confused as to who I was showing these pictures and videos to. Maybe I'd ask her for a mailing list later, or I could just put it on the school's server. Either way, this seems like a lot of annoying busy work.

She sat up and looked at me lustfully. "I need your cock in me, Darrell. I mean, I want you to blackmail me into sex. I mean, I don't know. Just fuck me already." I stopped recording and got undressed.

Looking at my exposed penis, the Principal seemed to get an idea in her mind. "How about I blow you first? Would you like that," she asked. She got away with masturbating in front of me for free. I wasn't going to let her blow me for free.

"Absolutely not, principal," I said firmly.

Her face dropped in disappointment. "Those rumors about me written in the boy's bathroom aren't true, you know...," she said, sounding defeated. Principal Locke laid down on her desk. Being much more experienced with this part of the job, I climbed on the desk and navigated my erect cock into my naked Principal's pussy. She immediately let out a moan. As I started to pump her, she lifted her head and made eye contact with me.

Frequently interrupted by her own moans, she started talking to me. "You're actually going to make me take your cum into my fertile pussy, aren't you?" I started to speak, but she put her finger over my mouth. "Don't say another word. Every time you speak, I end up deeper in blackmail. At this rate, you'll have me giving you anal sex in front of the school board. As hot as that sounds..." She let out a particularly loud moan. "...I need to keep this contained."

The Principal's hands found her ample breasts as she seemed to be immensely enjoying this experience. "I'm going to take your cum and bear your fruit, the child of one of my students. Every Principal's nightmare but secretly so hot... You didn't hear me say that," she said, a bit ashamed. That sounded like a lead I should pursue with some of the other school principals. Principal Locke's hands moved from her chest to tightly grab the edges of her desk.

Her legs spread even wider as she beckoned me to thrust into her deeper and harder. As I did so, my Principal sounded like she was hyperventilating. But she managed to ask, "Are you close?" I nodded my head yes. Her face showed a vast mix of emotions, including lust, worry, and dread. But my face showed one emotion. Professionalism. I prepared to give my client what she wanted. Reaching my limit, I unloaded my cum into her pussy which seemed to prompt the Principal to achieve her own very loud orgasm. This was my favorite part of the job. Completing the customer's order precisely as they wanted. I also like this part because I get to cum inside a hot woman.

Keeping my composure, after I was sure all of my semen had been deposited, I withdrew from her and got off of the desk. She stayed lying on the desk with her hands covering her face as she seemed to maybe regret paying a student to impregnate her. I never appreciated that buyer's remorse was a thing in the sex worker industry until now. I got dressed and left the office, almost forgetting to close the door behind me.

Outside the office, a large group of teachers, parents, and students had gathered. One of the students asked me, "What the hell was going on in there? It sounded like you and the Principal were having loud sex." I realized this could be embarrassing for Principal Locke, and I had to choose my words carefully.

"As a professional prostitute, I am obligated to keep my client's information, which includes Principal Locke, confidential." I took a step before realizing I should say one more thing. "If you are interested in the photos and video, you should ask the principal to include you on the mailing list." The room exploded with questions, sounds of shock, and high-fives. I eventually was able to sneak out and get away from the crowd.

Before too long, Aubree found me. "I'm sorry about that. The Principal made me do those things to try and get you in trouble. I'm sure you just spent the past hour in hell because of what I did," Aubree admitted. Taking all of those pictures was annoying, I thought.

I took her hands and tried to reassure her. "It's okay. Everything turned out good. Even the Principal got what she wanted in the end through some very confusing ways. But I want you to know I meant everything I said to you. I would be honored to take your virginity at no cost."

"Oh, that was a total lie. I've fucked a lot of dudes. Like, a lot. Mostly older men because they last longer and aren't as squeamish about butt stuff. But I still wouldn't mind fucking you. As a man whore you probably are packing quite a huge package," she said, giving me a seductive look. After explaining that my penis was a bit shorter than three paper clips lined up end to end, we both agreed not to pursue sex with each other.

The following Monday, after a peaceful weekend at home, I was eager to get back to school and sell my body. The opportunity came when two gentlemen approached me. "Darrell, you are a prostitute for hire, right," one of them asked me.

"I am! You must have heard me on the morning announcements today." It took so long for me to finally convince them to let me make that announcement. I had to agree to change the line, 'I promise I will inseminate you as you cum on my cock' to 'I promise fun times.' The line about me watching you masturbate they were fine with.

"Yeah, so can we pay you to have sex with someone else," the guy asked, giggling.

"Provided the other person is willing, yes. No money back though if they don't want to fuck though," I instructed.

The two guys laughed together for a while before they could explain what they wanted. "We want to pay you to go to the girl's varsity volleyball team and say you were paid to take all of their virginities and impregnate them. They are all 18 years old, so it's all above board. It's going to be so funny," they explained. The team consisted of ten girls. Each girl would cost 220 dollars, including impregnating them. In total, that would be 2,200 dollars. I figured I'd give them a group discount and round that down.

"I can do that for 2000 dollars," I quoted them.

The two guys looked shocked. "All we want you to do is to tell them you were paid to fuck them," they explained.

"Yes, I charge 200 dollars per girl. I'm giving you a discount here," I explained.

"They aren't going to actually want you to fuck them. You know that, right?"

"In the world of male prostitution, I don't deal in maybes. You pay me for this, I'm going in with the assumption these girls will happily accept the free sex. They would be fools not to."

They stared at me for a bit before one of them finally caved. "You know what, fine. This is going to be so funny. I'll gladly pay 1000 dollars for it. Frank, give him your 1000 dollar half," one guy said, handing me a large stack of 20 dollar bills. They say that people don't carry cash anymore. I have found that people seem to carry crazy amounts of money.

"Dude. I'm not paying 1000 dollars for this. Maybe 10, not 100 times that much," the other guy complained.

"But think how funny this is going to be," his friend countered.

"Is it that funny? Also, we won't even be there to see it. We will just have to imagine it, and we can do that for free."

"Dude, remember when you said my idea to leave love notes in John and Todd's lockers wouldn't be funny? How did that turn out?"

"Not very funny at all, but I'm happy that they found love with each other," the friend replied, confused about what his friend's point was.

"Exactly! This is no different!" The friend shook his head, trying to get that stupid point out of his mind.

"How about we just pretend to be the prostitutes? That way, it doesn't cost us two grand, and we get to be there to witness their reactions."

"It won't work, dude. Everybody knows we aren't male whores. That's kind of what we are known around school for. It's got to be Darrell, or it won't be funny. Just give him the money already." The friend finally handed me the other half of the money but didn't look happy about it.

"Thank you both. I'll approach them after practice this afternoon in the locker room."

"Just... don't tell them we sent you. Okay," the friend asked, and I nodded. Our business was concluded, and we parted ways.

That afternoon, I went and watched the girl's volleyball team practice. They were amazing. Their athleticism, teamwork, and dedication to the game were incredible. I also learned that they were highly expected to win the state tournament in a bit over a month. I felt so proud to have a team like this represent our school. But then practice ended, and I headed off to the locker room to announce I was available to fuck them all at no cost to them.

I entered the girl's locker room. Normally, I would not be allowed to do so, but I felt that as a male prostitute, I should have an exception. The ten girls were all sitting around discussing an upcoming match. I made my presence and intentions known to the team. "Good afternoon, girls. Fantastic practice today. Anyway, I have been hired as a male whore that any and all of you are free to use to lose your virginities and get pregnant." I braced for the chaos of the girls trying to secure the first spot to have sex with me, but that didn't happen, surprisingly.

"I'm sorry, who paid you to fuck us," one of the girls asked.

"I promised not to say," I replied.

"Either this is a very dumb joke thought of by two of the stupidest guys in our school or..." one girl started to say before another finished her sentence. "...this is the reward coach promised us for hustling during practice." The girl's eyes lit up hearing that.

One of the girls stood up, not looking convinced. "You seriously think, as a reward for doing an acceptable job in practice, that our couch hired us a male prostitute to take our virginities and impregnate us? All the previous rewards we got for hustling were either letting us leave practice 10 minutes early or a Blow-Pop. I'm thinking this might be a joke."

"I know this guy. He's Darrell and is a real male whore. You can check the school's Yelp reviews. He's legit," another teammate pointed out.

"Remember last time we didn't appreciate something the coach got us? She brought in that grape sports drink, and when we told her we didn't like grape flavor, she made us run five laps around the gym. If we disappoint her again like that, it could be seven laps," a girl said fearfully.

The skeptical girl spoke up again. "Ladies, please just think this logically. On the extremely small chance this is actually the reward our coach got us, if we don't let him fuck us coach gets mad at us and we run some laps, which we do all the time anyway. On the very likely chance this is just a joke, we could lose our virginities for no reason and get knocked up, which would change our lives forever."

"But we would be positive that coach wouldn't be mad at us," a girl in the corner commented.

"Then it's decided, " a teammate said confidently. "The only logical choice is we all have unprotected sex with this guy." All of the team nodded in agreement except the skeptical girl, who looked at her teammates with horror.

The confident teammate looked at me. "Darrell, is it? How should we do this?" I thought hard about the situation. I estimated I could probably produce enough cum to cream pie five of them. It was embarrassing to admit, but I probably wasn't going to be able to impregnate the whole volleyball team. If word got out about that failure, it could ruin me. But that was a problem for later.

"I've fucked a lot of high-school senior teams," I lied for the purpose of gaining their trust. "The best bet would be for me to fuck two of you at a time. I got back and forth between your pussies every minute until I cum in one of you. Whoever it happens to be in will be random. For the girl who doesn't receive my cum and fails to become a teenage mother, my apologies for the disappointment. Let's start with you two," I said, pointing at two random girls. As the girls undressed and exposed their naked bodies to a man for the first time in their adult lives, they introduced themselves at my request. It would be weird to have sex not knowing someone's name, and I wanted today to be as normal as possible.