Memoirs of a Haul Boy Pt. 03

Alex's family was known for three things in South Carolina: Real Estate Development, Politics, and Freight. Several State Politicians were members of Alex's family with a couple judges and some real estate tycoons. The freight company of Alex's Uncle Richard was very successful in its own right. Richard was closeted gay his whole life. He started driving trucks after real estate disputes with his brothers. It was a way to stay away from their drama and there was a big need for drivers in the 1950's. He knew too many gay truck drivers that had disappeared or had been murdered on the job. This is why Richard started his own fleet which employed all gay drivers. He could try and protect them if they were banded together. Over time, he noticed his guys had less incidents when his drivers were together. At first he thought they were just watching out for each other, but then he realized they didn't have to look far when the truck next to them was on the same team.

He couldn't just keep sending two drivers and trucks on every trip together. He combed the gay clubs for some straight laced guys that could keep his drivers satisfied and out of trouble when on the road. It was difficult to find the right person. Someone who was clean, didn't drink heavy or use drugs, and had no issues with a work environment that involved lots of sex. They also had to be compatible with the drivers.

An added bonus was less incidents meant his drivers weren't in the news. Any news of a gay driver for his company could have political repercussions for his family. Haul Boys had become a vital way of doing business for Richard. He figured it wasn't really immoral as long as everything was consensual. It helped save lives. He started to screen his employees for STDs during the AIDS pandemic. This further protected all of his employees.

I had been living with Alex for almost a year. I gave up on contact with my family. I was in exile. My last phone conversation with my mom ended with her saying "you're nothing to me, faggot, now stop calling."

Alex was aware of my desire to transition and supported me. He even pulled some strings to get me on his company's insurance and help me with the cost of my hormone treatments. The only issue was he wasn't attracted to women. I had no plans to fully transition. My desire was to be able to express myself as a girl, as a boy, and somewhere in-between. I favored being a girl, but I had also just spent eighteen years as a boy full time. Even so, I was too feminine for him and that affected our ability to be in a relationship. We still had playtime, but we agreed we were not in a monogamous relationship. I was stuck at the house without a job, so I wasn't meeting new people.

Alex and I had moved into the house he purchased by this time. It was more private and on quite a bit of land. It was midday when the door bell rang. It was a salesman. He was selling Bibles. I was bored out of my mind so I talked to him for awhile. I was fully dressed and in makeup. He didn't seem to suspect a thing, or he didn't care if he did. I couldn't tell.

"You know, this is a rare treat for me. I usually don't get to spend so much time with someone as knowledgeable about the Bible as you are, or as pretty as you are." He said.

"Well, I've been through a lifetime of Bible Study, and thank you." I said, with a big cheesy smile.

"You are cute, you have an exotic quality to you, I think." He said while he eye fucked me.

I blushed, I like older men, but this guy was a mess and not what I was into. He was balding, which is fine, but his hair was messy and grown out. He was overweight, which is fine, but he wore a suit that was comically too small. He wore a clip on tie that was falling off and didn't even go down past his navel. His nails were long and bitten off. He just looked messy and unkept, and maybe a little odd.

His flirtation became very direct. He started to touch me in innocent ways. I smiled. At this point, an experienced girl would have already sensed the direction this was headed. I knew what he was after, I just didn't think he would be so brazen.

"I've only been with my wife. She had an affair about seven years ago with the Branch Manager at the Bank. He made it up to us with a really good refinance on our mortgage. He's a good guy. I'm allowed to do this. My wife gave me a get out of jail free card" The salesman said as he grabbed my face and kissed me.

I thought, "Fuck it. He's better than the dildo."

I kissed him back. He grabbed a handful of my ass and started to rip off my clothes. He had my skirt and panties down before I could stop him. That's when he had a full mental breakdown.

"You have a penis!" He screamed.

I shook my head. I felt bad, I should have warned him. Things just happened so quick.

"I'm happily married! I'm not a faggot! I'm out here spreading the word of The Lord, and you're spreading AIDS for the devil!" He screamed.

"I don't have AIDS, sir, and I'm sorry." I said, right before the first Bible hit me in the face. The next Bible went through the window behind me. He kept throwing Bibles at me. I was naked from the waist down, afraid, and had a Bible Salesman hurling expletives and Bibles at me. I tried to run past him, but he grabbed me. He slapped me on the face hard with the King James Version. I kicked him in the nuts with everything I had. He hit the ground screaming and crying. I threatened to kick him again. He gathered some of his Bibles and ran out the door to his car.

Alex found the story both hilarious and scary. He could have pulled a gun on me or easily beat me. It was definitely a lesson for me.

"I mean, Jesus, Jesse. The Bible Salesman? You must be pretty desperate to let that one have a go." Alex laughed.

I shrugged. "I'm stuck here all the time, and someone is always giving their dick to college boys who listen to way too much Abba." I said.

Alex didn't say anything.

"Didn't you say you just fired a driver's assistant the other day? Is that something I could do." I asked.

Alex spit out his water. "I mean yeah, you could do it. You could actually do it really well, now that I think about it, but..... I don't know if you would....." Alex replied.

"What do I have to do?" I asked.

"Well, all of the truckers are gay or bi except for two guys I just hired. The South isn't friendly to gay people, and it's usually much worse than throwing Bibles at you. My Uncle started pairing assistants up with the drivers to keep the drivers from looking for company when on the road. Three of his drivers were lynched and murdered at Truck Stops before he started doing that. We haven't had an incident since and it's been forty years. He was desperate for a solution, and this is what we have." Alex said.

"So....I would sleep with the drivers?" I said.

"For all intents and purposes, yes." Alex said.

"And I would get paid for this?" I asked.

"They average about sixty hours a week at fourteen dollars per hour." Alex said.

"And I get dick?" I replied.

"Yes, Jesse. Lots of it." Alex said annoyed.

"Are they hot? I asked.

"Well, it's a variety. Some are." Alex said, annoyed again.

"Why did you fire the last guy?" I asked.

"He failed a drug test. Crack Cocaine. We can't have that in our business. Everyone gets regularly STD checked and drug tested. Even the girls in accounting." Alex said.

"I don't do drugs. I don't even drink. I'm already a fake employee for my health insurance. Why don't we just make me a real employee. It solves all my problems. Money, boredom, and the lack of dick in my life." I said, loudly.

"Let's think about it Jesse." He said in an annoyed tone.

"I could be having a good life in Seminary right now, planning to marry that Vanessa chick at church, but no.... someone wanted to put their penis in my butt while my parents ran a quick errand, and then we got busted. No more Jesus and no more all you can eat crusty seafood buffet for me. You owe me!" I said.

Alex laughed hysterically. "Gross, Jesse!" He managed to say between laughs.

"Laugh it up. I got kicked out of my family because of your libido!" I shot back.

"It's not like you weren't involved. I also seem to remember how miserable you were your entire life, so let's not go there, Jesse," Alex said with a smile and continued in a more serious tone "I need someone to ride with Dan on Thursday to Austin. You should get back on Sunday. Dan will go easy on you. Want to try a test run?"

"Yes! I'm going to fuck Dan's brains out, and get paid." I said.

"Sounds great, Jesse." Alex said.

"Does he have a big dick?" I asked.

"I don't know Jesse. Get your ass in the car. I feel like Mexican tonight and I'm done with talking about dicks." Alex said sarcastically.

Dan was overweight, balding, and totally hot. His hair was trimmed short, his beard was trimmed neat and short, he wore a nice Polo shirt that fit him well, and a white pair of New Balance sneakers. He was married and had two kids. He had a touch of grey and was fifty-two years old.

I sat anxiously in the passenger seat. Alex picked out my wardrobe for the trip. I wore a pair of super low rise jeans that my panties poked out of and a tight fitting top that exposed my belly. I looked hot, but still conservative. It matched well with Dan.

I was nervous because Dan may not like me. I was nervous because Dan may like me. I had only had sex with Alex. I was worried about intimacy with another man. What if Dan had some freakishly large cock? What if he had a tiny cock? What if Dan wanted me to top? What if Dan didn't like girlie-boys like me?

"I love my wife, Jesse." Dan said with a pause, "it's not her fault that she doesn't have a cock. I thought I could grow to like sex with her if we got married, but she doesn't do much for me. We are absolute best friends and in love, I just don't have sexual desires for her. It might be a little different if she would do anal, but she refuses to try. I was really surprised to see you when you got in the truck. You look more like my wife than the last Haul-Boy."

"I mostly dress as a girl around the house. I dress as both a boy and a girl in public, depending on what I'm up to." I told Dan.

"You still have your penis, right?" Dan asked.

"Yes, I don't ever want any surgery down there." I said.

"Really, I figured with you being so passable, you would want to do the complete transition."

Dan said.

"I like being in the middle. I do hormone treatments, but I can still pull of being a guy when I want to." I said.

"That's interesting. Do you have sex with females or other trans? Do you top with guys?" Dan asked.

"I'm only attracted to guys, and I only bottom. Sticking my dick in someone just seems ridiculous and phony to me, I don't know why." I said.

"I like to masturbate and touch guys on the breaks. I've never done anything beyond touch with anyone other than my wife. You have to understand, kissing and sex is for my wife." Dan said.

Our first break came at the Texas Border. It had been a long day of riding with a stranger. Dan went into the sleeper first and I joined him. He sat on a rack and undressed himself. He motioned for me to walk over to him. I did so and he gently undressed me. He rubbed his big muscular hands over me and gently caressed my body. It went from awkward to hot, pretty quick. I looked down at the massive torpedo between his legs. It looked like the most suckable and fuckable dick in the world, and my best hope was to only get to stroke it.

Dan picked me up and sat me on his lap, facing him. He spit on his his right hand and slowly inserted two fingers into my rectum. He then started to lick and suck on my nipples, which surprised me. I scooted forward. The torpedo pointed straight up and was the only thing that separated us. I reached down and grabbed Dan's manhood. I gently stroked it. I brought my hands and smelled them. I spit on my hands and went back to gently stroking his cock with a swirl motion.

Dan moaned loudly. He continue to probe me with his fingers and suck on my nipples while I stroked him. Dan began to kiss my small breasts and follow them up to my neck. I stroked his cock harder. Dan leaked precum. I scooped it in my hands and liked the precum off them. Dan kissed all the way up my neck and made it to my lips. He kissed me deeply. He pulled his fingers from my anus and spit on his hand again. I quickly turned around in his lap and straddled him with his cock between my thighs. I lubricated his cock with my spit and started to hump the torpedo with my thighs.

Dan moaned loudly. He kissed the back of my neck and sucked on my ears. I turned around and he kissed me again passionately. Dan reinserted his fingers in me while I humped on the torpedo.

Dan moaned loudly, picked me up, turned me around, and placed me down on the rack. He spread my legs and took me in missionary. Dan let me adjust to his size before he laid the pipe in me. I came between our bellies twice and he came deep inside of me. He kissed my body down to the puddle on my belly and licked all of my cum up. He then returned back up and kissed me some more.

BEST. JOB. EVER.