Memoirs of a Haul Boy Pt. 05

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Collected memories of a transitioning femboy in the mid 90's.
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Part 5 of the 8 part series

Updated 06/11/2023
Created 04/03/2022
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Tommy was one of the two straight drivers that Alex hired. Tommy was loud and obnoxious. He wore a CAT hat with flames on the side. He wore Dale Earnhardt t-shirts, almost exclusively. He was just one of those guys that did not have a filter. The office staff hated him. The others drivers hated him. Tommy ignored me. Sometimes he would walk out of the room when I walked in. Alex was the only person that liked Tommy. Tommy got shit done.

Tommy's work performance merited that he received better jobs. Alex put him on the rotation for the more lucrative long hauls. Tommy didn't name a preferred assistant for the first long haul so he rode solo. Everyone was surprised when he requested an assistant for his second load. He requested me.

"Maybe he just wants company. I can't tell him that he can't have an assistant because he is straight. It's fine if you don't want to go with him, though." Alex told me.

It was a really long haul. I figured he wouldn't hurt me. Worst case is it would be very awkward. We would be going to just outside of Seattle, Washington. I packed for a week. I decided to bring a variety of clothes. I could dress conservatively as a girl. I could dress androgynously. I also packed a couple sexy items.

Tommy headed towards towards Nashville. He decided to take the northern route through North Dakota. Tommy hardly spoke the first day. It was work related when he did. His truck was immaculate on the inside. Even cleaner than Dan's truck. He also did everything by the book. Where most drivers would pencil whip the forms and logs, Tommy took it very seriously.

Tommy was also a gentleman, to my surprise. He helped me up to the truck. He helped me down from the truck. He wouldn't let me pay for my own snacks or meals. He treated me with absolute respect. I was shocked. He was clean shaven. He wore a Polo shirt. He spoke about going to the gym, and I could clearly see he had been working out. Tommy was way different than I thought.

He started to talk more at dinner. We were done for the day.

"So, what's the deal with you and Alex?" Tommy asked.

"Alex was my best friend growing up. We've been intimate for a couple years, but our relationship is strictly friends." I replied. I didn't want to talk about the boss too much.

"Is sex with the drivers just sort of..... business?" Tommy asked.

I looked at Tommy straight in the eyes and said, "Not at all. I've never had sex with Eddie. I've never seen him naked. He just likes the company, and I guess the eye candy. I only have sex with Dan and Mark because I enjoy having sex with them. I don't ride with Russell anymore. I enjoyed sex with him on the first trip, but the last trip was too strange. I'm not going to have sex with someone unless I want to have sex with them."

"What if you met someone that you liked?" Tommy asked.

"If I wanted to have a monogamous relationship with someone.... then I would." I answered.

"Tommy, why did you request an assistant?" I asked.

"I wanted to..... I wanted to um. It's a big deal around the shop and I just, you know, thought, why not?" Tommy said, staring at his meatloaf.

"Why did you come with me if you can ride with whomever you want to?" Tommy asked.

"I thought, you know, why not?" I said with a smile. Tommy laughed with me.

I then worked up the nerve to ask, "You seem really different Tommy, you're more reserved, and you aren't telling offensive jokes. Why the change?"

Tommy stared at me for a moment, shook his head and said, "I'm really socially awkward. I force myself to talk a lot. I say jokes that I don't really find funny but I think the other person will like. Everything comes off wrong. I didn't talk to you much today, because, I'm.... just getting to know you."

I smiled and said, "only tell the jokes you find funny, that's the ones I want to hear."

Tommy grinned.

Tommy paid for dinner after we finished. He got up to go to the bathroom and I followed. I had to pee really bad. The ladies room was full. I cracked the mens room door and looked in. Just Tommy. I locked the door behind me so nobody would come in and freak out. I walked up to the urinal next to Tommy, hiked up my skirt, pulled my little cock out, and I started to pee.

Tommy looked at me in complete shock. I smiled at him and then looked down at his cock. I broke the sacred rule of all mens rooms. I was definitely intrigued. He was circumcised, and he was a large boy.

Beet red and in shock, Tommy yelled, "Hey, you can't do that. You have to look forward. That's the unbreakable rule!"

I turned towards Tommy, and seductively whispered in his ear, "What are you going to do about it, Tommy? Give me a spanking when we get back to the truck? Teach me a lesson in bathroom etiquette?"

"I just might!" Tommy said.

Tommy and I walked back to the truck. Tommy sat on the rack. I dropped my skirt and laid across his lap in my little black thong.

"What are you doing?" Tommy said.

"Waiting for my lesson." I said.

"You want me to hit you?" Tommy asked.

I wiggled my ass and said, "I was bad, right?"

Tommy was quiet.

"Spank me. Spank me hard, Tommy." I said.

Tommy placed his large hand on my butt.

"Mmmmm. Show me who's in charge, Tommy. You don't want me to misbehave the next five or six days, do you?" I said.

Tommy spanked me hard on the left cheek. Then on the right cheek. I had never done anything crazy like this before. I had read about erotic spankings in Penthouse Forum before, but this was very new to me.

"I'm going to teach you something." Tommy said as he picked up the pace and spanked harder.

Tommy spanked me hard, swat after swat. Each slap reverberated in the small cab. My ass felt like it was on fire. Tommy just spanked harder and faster. Tommy's cock was as hard as my ass was red. His tool pressed into my girlie cock with with force. My ass hurt but I was turned on. This was hot.

Tommy spanked me hard and fast for what seemed like forever, but was probably only five minutes. He stopped and rubbed my sore ass. He let his fingers run up and down my thong string as he massaged my sore bottom.

"Did you learn your lesson?" Tommy asked.

"Yes sir. I'm going to definitely do that again." I said.

Tommy laughed.

Tommy continued to run his fingers up and down my crack. He would pause over my entry and then continue again. I started to push against his fingers when he paused. Tommy pushed his fingers down harder. His cock strained so hard against his pants, I could feel it tremble.

"Tommy, would you like for me to do something for you?" I asked as I reached between his legs and grabbed his hard cock through his trousers.

Tommy said nothing, but his cock sprang to attention. I got off his lap and kissed Tommy's cock through his trousers. I carefully unzipped his pants and helped him pull off his trousers and briefs. His cook stood straight up. I've never really seen a cock that was that hard in my life. It was the most beautiful penis that I had ever held in person. It was nine, maybe ten inches long. Big round mushroom head. Perfect thickness, around two inches in diameter. He had a slight bow upwards. It was a smooth creamy color. It was the type of cock you would think of when you masturbate. Tommy wasn't shaved, but he wasn't too hairy. I kissed his sweaty balls and planted small kisses all the way up his cock to its glorious head. I darted my tongue under and around the head. I swirled my tongue all over the head. I opened my mouth and took Tommy in slowly. Tommy tasted wonderful. He tasted like man with maybe a hint of Irish Spring.

I worked his tool towards the back of my mouth. I wanted to take my time and worship this beautiful cock.

"Oh my God!" Tommy gasped. "You are amazing."

I built up some spit and worked him to my throat. Tommy laid perfectly still as I throated him as deep as I could. I backed off of his cock and sucked on his balls. Tommy moaned loud. I went back to his cock. It was covered in precum which I licked and swallowed. I worked Tommy's cock, but not too hard. I didn't want him to cum yet. I wanted to feel this cock throbbing inside of me.

I stopped and grabbed my bag. I pulled out some lube and prepared my entry. I then lubed Tommy up. Tommy sat perfectly still. I hovered my entry slowly over his magnificent cock and lowered myself down in cowgirl.

Tommy felt amazing inside me. He looked at me as if he was in some sort of pleasurable coma. I rode Tommy's cock and fucked him with everything I had. He laid still and stared at me. I worked him as deep as I could. I pulled off my shirt and Tommy stared at my little boobs. I grabbed his face, pulled it towards mine, and kissed him. Tommy returned my kiss, grabbed my waist, and took charge. He stood up, held me with his strong arms, and fucked my whole body. Tommy was an animal. I wrapped my legs behind him and held on as best as I could as he pounded me.

Tommy threw me on the rack. He got on top and kissed me deeply. His monster cock slapped and rubbed against my little girl cock. Tommy kissed me down my neck and to my chest. He sucked on each nipple and licked me down to my cock. Tommy inhaled my cock as I laid in ecstasy. Tommy then worked his tongue all the way back to my lips and kissed me greedily. As he kissed me he worked his engorged tool between my cheeks and impaled me in missionary. I had been worried about Tommy lasting, but it was me who couldn't hold on. Tommy pumped me as my little cock pumped cum onto my belly. I came so hard I that I saw stars. I nearly lost control of my body functions. My orgasm set off Tommy. He flooded me with his seed. Tommy held and kissed me until I fell asleep.

A truck driving by woke me up the next morning. Tommy still held me tight in the small rack. His hard-on buried between my legs. It was time for us to get breakfast. I got up and crawled to his cock. I woke up Tommy with a blowjob.

Tommy moaned. "Oh my fucking God Jesse. You are amazing,". He said.

Tommy grabbed me and rolled me on top of his body in a sixty-nine position. He arched his back and took my little girl cock in his mouth. He sucked on my little cock while I worked his tool. It wasn't long before I had a mouthful of Tommy's cum.

We got dressed and ate breakfast. Tommy treated me as if I was the most important person in his world. He was an absolute gentleman, he was protective, and immensely sweet.

I looked at Tommy once back in the truck and asked, "Tommy, have you ever been with a girl like me before?"

Tommy looked at me and looked down and said, "You're the only person that I have ever been with."

I leaned over and picked up his chin to look him in the eyes, "we have almost a week to make up for lost time."

Tommy smiled and said, "We have a week for me to correct your bad behavior, too."

I looked at Tommy devilishly. We were going to have fun. A lot more fun than I had the night before we left on this trip.

The Reverend at my parent's church, Ocean Shore, was a man named Calvin Nash. He went by Cal. He was a little younger than my parents and had a strong bond with his flock. I've had a crush on Cal as long as I can remember. Baptist Priests can marry and have family, but Cal never even dated. He would always say that his commitment was to God.

I was shopping at the grocery store that evening when I felt a tap on my shoulder. I turned around to see Reverend Cal.

"Hey Jesse! How are you?" Reverend Cal asked while he stared with his blue eyes. I was hypnotized, almost. I was also surprised that he recognized me while dressed.

"I'm fine." I mumbled.

"I was hoping to run into you while I was in town. You look great! Is there somewhere we can speak privately?"

I've known him all my life and trusted him completely. He followed me to Alex's house. Alex was off in Columbia listening to ABBA and Gloria Gaynor.

I poured the Reverend a glass of sweet tea. I felt really underdressed. I wore shorts that didn't even cover my butt and a tight cut off shirt. Reverend Cal stared at me and smiled. We sat on the couch.

"It broke my heart how everything happened with you and your parents," Rev Cal started, "and I wish I could have intervened. Stuff like this happens in my flock, and I can help. You could have stayed with me."

"I didn't know." I muttered.

"Oh Jesse, we've spent a lot of time together," the Reverend said as he placed his arm around my shoulder, "you could have told me that you had these desires a long time ago. It could have been our secret."

I didn't understand what was happening. What was Reverend Cal saying to me?

Calvin held me tighter and said, "it is natural for people to have urges. It is even fine to act on those urges, as long as do it the right way with God."

He really lost me. This was the same guy that spent eight or nine Sunday Sermons in a row last year preaching about the evils of homosexuality and how it is unforgivable in the eyes of the lord.

The Reverend slowly inched his face towards my face. I couldn't believe this was happening, and then it did. He kissed me. Overcome with confusion and all of my old feelings for him, I kissed him back. It felt so wrong.

Reverend stuck his hand on my thigh and said in a tense tone, "I have chosen to give my life to the church. A marriage with a woman and children would be too much distraction. I wouldn't be able to devote my time to the church and to Jesus as I would need to. There are other options, though. You know from my teachings that Jesus spent time with prostitutes. This allowed him to be free from distraction with his teachings. You could be the same for me. You could help me keep focus on my flock."

I was speechless. i wondered to myself, "What in the fuck is he talking about? I know the verses well and that isnt what they meant."

Cal grabbed my face and kissed me. He pushed me down on to my back. He unsnapped my shorts and pulled them and my thong down to my knees. Cal pulled me back til my legs hung over the armrest of the sofa and then flipped me over. I heard his zipper. He spit on my crack and on his hand. His cock slipped between my cheeks and pushed on my entry. Reverend Cal pushed harder and his cock slid into my anus. Calvin softly bit the back of my neck and ears as he fucked my ass. His thrusts were deep and fast. Very rough. It hurt because I wasn't properly prepared and it also hurt because he fucked me like he hated me. He grunted as he thrust his cock into my ass, his body slapped my cheeks hard with every thrust. I began to hate him more with every thrust. I just wanted this over with so I could avoid him the rest of my life. He started to push deeper and quicker with shorter breathes. I squeezed on his cock and he came in my sore hole.

The Reverend quickly got up and dressed himself as I laid over the armrest, still trying to figure out exactly what had just happened. There was a loud knock at the door.

Cal and I fixed our clothes and I opened the door. I prayed it wasn't the Bible Salesman. I had already had enough religion in me that night. It was Alex's Uncle Charles, the State Senator.

"Hello Jesse. I heard you might be home." Charles said.

"Hi, Mr Rumghaud. This is Reverend Calvin Nash." I said as I gestured towards Cal.

"Hello Senator. I was actually on my way out the door. I was just visiting with a former member of my flock." Reverend Cal said as he shook both our hands and left.

Reverend Cal looked at me through the window and winked at me. He blew me a kiss and took off in his car. The curtains were open and I knew at that moment that the Senator had been able to see everything going on before he knocked on the door.

Charles closed the door and said, "I needed to speak to you Jesse. You are all that I have thought about since that fundraiser."

I looked at the Senator in shock and said, "you know Senator, I'm a little different than...."

The Senator cut me off, "I know Jesse. I know everything about you."

Charles grabbed me and kissed me. He ran his hands all over my body as he kissed me. I stood there in complete shock as he kissed me, with the Reverend's cum running down my legs.

"I can give you things that Reverend can't. I can give you a life that Alex can't," the Senator said, "jewelry, nice clothes, nice car, and a nice house. I can give you stability. I love Alex dearly, but you might be too much woman for him now."

I couldn't believe this was happening. I just froze. What could I say or do?

"Now show Daddy Charles how much you want this job." The Senator said as he pushed down on my shoulders until I was kneeled in front of him.

He pulled out his cock and pushed it against my lips. I opened my mouth on instinct and he pushed it all the way in with a grunt.

"Suck it, girl." He said.

The Senator pumped his cock in and out of my mouth as I held my mouth open. I looked over at the window and could see Reverend Cal on the side. He watched as the Senator pumped my face. The Senator's sweaty balls slapped my chin as he worked his tool in and out of my mouth.

The Senator moaned and said, "you are going to make one helluva intern, girl."

The Senator fucked my face. I didn't suck or do anything other than hold my mouth open. His motions pushed me back until I was pinned against the sofa and his legs. He picked up the pace even more. He moaned loudly as he fucked my face. He tasted like Baby Powder, sweat, and mothballs. He smelled like he didnt wipe his ass. He groaned loudly and filled my mouth with his warm cum. I drooled all the cum down my face and on to my shirt.

The Senator dressed and said, "Thank you dear. I needed that. It's been tough since Lindsey left and his heartless sister divorced me. I will be in touch dear. Don't worry about that crazy Minister. That Church is a Cult. They may get some investigations from the State soon. I'm going to take care of you, you hear?"

I looked back at the window. Cal was gone. The Senator had now left too. I took off my clothes and took a shower. I used an enema to help myself feel clean again. I had been a haul boy for a year and a half now, but this was the first time that I had ever felt like a whore. A whore paid with promises that she didn't even want in the first place. I got out of the shower and put on my pajamas. I had already packed and folded all my laundry. I took my soiled shorts, shirt, and thong and threw them into the back of my closet. I would deal with them later. For now I didn't want to see them.

Tommy and I had nearly made it to Seattle when traffic completely stopped at Snoqualmie Pass. It took several hours for the pass to be cleared. Tommy used that time to see if he could get me pregnant. He did a really good job, but no babies yet. Tommy had to pull off the road shortly after the pass in a rest area to prevent him from going over fourteen hours. We were now an entire day behind. We would not be able to make it to the dock during receiving hours on Friday. The customer couldn't unload the truck until Monday, so that meant we had to wait the weekend. They at least had a secured lot. Alex arranged for a rental car company to pick us up at the lot. The truck would be safe until Monday. Alex also arranged a hotel room for us at the Grand Hyatt, downtown.

This was three nights with a shower, comfortable bed, some of the best restaurants on the West Coast in walking distance, and a big cock to make love to me. Tommy brought me to the Space Needle and the Pacific Science Center. Tommy took me to the movies and the zoo. We hiked in Mt Rainier National Park on Sunday morning. We visited a horse farm on the way back in Enumclaw and took riding lessons in the afternoon. A nice man who was an Engineer for Boeing took lessons with us.

Tommy and I rode back to the hotel for our last night in Seattle.

I looked at Tommy, driving the country roads back towards I-5. "Tommy, remember when you asked me if I would be willing to be in a monogamous relationship?" I asked.

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