Big Bobby and Sweet Sally

I pulled into the parking lot of the diner and parked in a spot close to the front door. As I looked up through my windshield at the glowing pink of the diner's neon sign, I was bathed in the light of its name, Dougie's. I sat there for a few minutes and considered the situation I now found myself in. Just last week I had been set up pretty well. I was still living at home with my mom, but I had a steady job at my uncle's landscaping business and had been making decent bank. Then things, as they do, took a turn for the unexpected.

My uncle had always been a little weird around me, ever since I hit puberty anyway. I shot up in height quicker than the other boys, but was lucky to avoid the dreaded curse of acne that had struck so many of my friends. My face remained smooth, and even though I devoured almost every scrap of food in sight, I barely gained a pound and continued to hold on to my skinny frame. I started working for my uncle a couple years after graduating high school and after I realized college was fading fast as an option.

My uncle had a couple of other young guys on his crew and he tasked me with just as much of the workload as them. He showed me no favoritism, and the work could often be grueling, but I didn't mind. I was enjoying the work and all the fresh air it afforded. In the hot summer days, we would sweat through our shirts before noon, and typically worked the rest of the day shirtless. That's when I noticed my uncle giving me some strange looks. He looked at the other workers the same way, so I didn't think much of it. It went on like that for about a year or so before it all came to a crumble.

One day, a day I was off work, I was sleeping in late when my mom came barging into my room with her voice hitting the highest pitch I'd ever heard it reach. She was yelling and ranting and making accusations a mile a minute. When she was finally able to make a coherent statement, that was when my mind started reeling and spinning as well. It turns out my aunt came home early one day and found my uncle jerking off into a pretty heavy sweat. This wouldn't mean much but it was what he was jerking off to that became the issue. It was me. He had countless shirtless pictures of me on his phone and was enjoying them so much he didn't notice his wife creeping up behind him with his pants literally down.

The only photos he could have possibly had of me shirtless were from work during the peak of the summer heat. I may have noticed his weird looks, but never his phone snapping picture after picture of my young slim body as it glistened in the searing sun. My uncle did the only thing my uncle could think at the moment, he lied. He lied from his teeth all the way down to his feet, and was somehow able to pin the whole thing on me. I was apparently the one that came on to him and had forced myself upon his body. Even going so far as to somehow make him let me blow him, however that's possible.

I had apparently turned my uncle gay was his reasoning. And now he was unable to get hard unless he looked at pictures of me, in various states of undress of course. I denied it and tried to explain the lunacy of the whole thing to my mother, but it was her brother. I guess in her eyes, her brother could never be gay, unless he was forced to. The only logical conclusion they could come up with was to be rid of me. So I was fired from my job, kicked out of my mother's house, and basically expelled from the family at large. And the craziest thing is, I'm not even gay, they didn't even consider that I wasn't.

My only option was to get out of dodge. The only thing I had left was my car, which got me out of there as fast as it possibly could. I would have stayed in town, but the thought that that juicy little bit of gossip wouldn't get around was next to nil. The last thing I needed was to worry what some asshole I was trying to get a job from thought he knew about me. I got what little money I had saved up, and I left. Now I was half a state away and looking for work, and Dougie's Diner had a help wanted sign in the window.

I looked in my mirror and made sure my hair looked good. I was keeping it short these days so at least there wasn't too much effort to be put into it. As I looked at myself, for some reason I thought of my uncle, and I pictured him getting hard and touching himself as he looked at my face. I was disgusted by this thought, but for some reason, it was a thought that kept creeping back to me over that past week. What was it about me that...NO, I needed to stay focused damnit. I sized myself up one last time in my mirror and then opened the door to step out into my hopeful new life.

I entered the diner and took a seat, not wanting to make my move just yet. There weren't too many people in the place and I planned it that way. I didn't want to come during the dinner rush or anything like that, as I was hoping to catch the manager in as good a mood as possible. A pretty girl with teeth almost as bright as her bleach blonde hair approached my table with a big smile already on deck. Her nametag said Mary and her uniform was slightly stained but snug in the spots it counted.

"What can I get you, babe?", she said with a purr.

"Just a, just a coffee."

"Sure thing."

She walked off and I couldn't help but scope out her backside and saw her uniform was pretty snug back there as well. I looked around to see if I could notice the manager. Mary returned with my coffee, and since the manager hadn't made his presence known, I decided to make a quick decision.

"Is the manager here?"

"Dissatisfied with the service already?"

"No, I, I'm looking for work."

"Oh, okay. I'll send him over to your table."

She walked off and disappeared into a backroom as I put some sugar in my coffee but otherwise kept it black. As I took some tentative sips, a big burly man with thinning hair took a seat across from me at my table.

"Are you, uh, Dougie?"

"I'm Doug. Call me Doug, alright?", he said with a grinless face.

"Sure, sure."

I looked down at my mug of coffee, now unsure of this whole thing.

"You looking for work?"

"Yes, sir."

"You work as a waiter before?"

"No, mostly landscaping, but I know a hard days work."

"Well you'll get it here. Alright, we'll give it a try."

"Really?! Thanks! I'm Sam."

"Doug. Call me Doug."

I started the very next day, and as I quickly found out, this was a truck stop diner. The close proximity to the interstate and the motel across the street should have been a dead giveaway I guess. I took to the job pretty quick, which I know Doug appreciated. Though I guess he had only ever planned on hiring girls as his servers because the only nametags he had were girl's names. I picked the one that was closest to my name, Sally, and begrudgingly pinned it to my shirt before my first shift started.

Like I said, our main source of business was from truck drivers. The motel across the street had a huge lot where the truckers could park and sleep for the night. They'd walk across the street for a quick bite before they hit their pillow or hit the road. They had fun with my nametag, making a quick joke which always made a few others chuckle. After awhile I got used to it, and soon I was confident enough to joke back with them, which definitely helped increase my tips.

But most of them were there for Mary, or as I soon found out she was nicknamed, Sweet Mary. She would flirt with every single one of them, and her tips increased exponentially because of it. They all loved her, but she definitely had her favorites, and she would flirt with them endlessly. I had to admit watching her turned me on, but after awhile it was hard to tell if it was because of her, or the lust I saw in each one of those men's eyes.

There were a few nights I'd hear quieter than usual whispers between her and one of her favorites, and then at the end of her shift I saw her sneak off with them to their truck, or if he was a particular favorite, to one of the motel rooms rented especially for her. There were a few nights I would lock myself in the restroom after seeing her arm and arm with her man and I would furiously masturbate as I thought of the thunderous night of passion I imagined them embarking on. If only I could see her in the throws of it, as she was taken, used, and penetrated by the heavy bulk and power of her favorites. Just once I would die to see her, to see them.

There was one trucker though that's name was legend among the men, his name was Big Bobby. Sweet Mary was his special girl and every man knew not to dare one word of flirtation to her whenever Big Bobby was in town. His rage was legend as well.

It was a particularly slow night one night at the diner. I thought it was because all the truckers knew that Mary was on vacation, but I soon found out the true reason. When he strode in with his full form and blood red trucker hat just slightly askew, I knew why they were all gone, because Big Bobby was in town that night.

He sat down at the counter of the diner directly in front of me. There wasn't another soul in the place. It was just him, me, and the cook who had stepped out thirty minutes ago for a prolonged smoke break. He took off his hat to reveal a thinning head of hair, but his curly and hefty brown beard made up for it.

He gruffly said, "Where's Mary?"

I stammered, "She's uh, uh, on vacation, sir."

I thought I saw a slight smirk before he finally looked up and took me in with his world weary eyes.

"That's a shame. A damn shame."

"Guess it's just you and me tonight, sir."

I don't know why I kept saying sir. Maybe I felt slightly intimidated by him and the fact that no one else was in the place. I felt his full attention pressing down upon me. His eyes looked away from mine and went to my name tag.

"Sally, is it?

"Sam, actually. It's the only one I could find that works."

"Works well.

"Thank you, sir."

Again another sir. I looked away sheepishly for a second, to see if the cook had returned. When I looked back to him, he was definitely grinning this time.

"I'm Big Bobby."

"Nice to finally meet you, Big Bobby."

"Have you heard of me?" he asked curiously.

"Just bits and pieces, here and there."

There was an extended silence, and then I finally gathered myself and realized my place.

"Oh, uh, coffee?"

"Would be delightful."

I went to the hot pot that had been sitting there half the night and poured him a heavy cup of the black stuff. I brought it back over to him and he took a long and strong swig. I was glad in a way to see him go right for it, not needing sugar or cream to mask its strong flavor and bite. He took it like a true man.

"Get you anything else?"

"A steak would be dandy. Scrambled eggs and baked potato on the side."

"You got it."

I gave him almost the same smile that Mary had given me that first day I'd come into Dougie's. After I wrote his order down I placed it where the cook could see it and then went back over and refilled his already emptied mug. And then, then we talked.

I found out we actually had a lot in common. He had also left home at a young age and was forced to find himself in the world. He found he loved driving, and could stand to do it for long stretches and loved to see every inch this country could offer. Hearing his descriptions made me yearn to see that much more of the open road myself. To take in all of the true beauty of nature and our native land.

I didn't understand why so many people were afraid of Big Bobby. He was one of the kindest people that I had run into yet. We talked all throughout his meal and all the way until the end of my shift. When I said it was time for me to go he just smiled an even bigger smile and left me the biggest tip I had received yet. Such a sweet, sweet, man.

After I closed out and said my goodbyes to the cook, I went out the back of the diner and was surprised to see Big Bobby leaned up against the back of the building. He was smoking a cigarette and had his eyes glued upwards and to the stars above. I decided to walk over to him to wish him a goodnight again before I headed out. After that larger than life tip I felt it only necessary to stay in his good graces as long as I possibly could.

"Uh hey, Big Bobby."

He took his attention from the vastness of space and trained his eyes straight on me. He took a tall puff off his cigarette and then tossed the remainder on the ground.

"Hello there."

"Thanks again, for the generous tip."

"And the conversation."

"And that, too. Really nice meeting you."

"You too, Sally."

I let out a little laugh. Not sure why, or why I didn't correct him.

"Heading home?"

"Yeah. You?"

"Just back to my motel room."

"Oh, you got a room?"

His ears perked up a bit as he turned his body a bit closer to mine.

"I had expected Mary is all. But guess it wasn't in the cards."

"Sorry about that."

"No need to apologize, but uh..."

"Yeah?"

"I was gonna go back to my room and have a drink. And I hate to drink alone. You maybe wanna come have a quick one with me, before you head home?"

I was thoroughly engrossed by our conversation earlier, and after hearing he really had his hopes up for meeting up with Mary, I would feel bad if I said no. Plus what could hurt from having one quick drink with the poor guy.

"Sure. I'd love to."

"Well then right this way my Sally."

Again, just a little laugh, no correction.

He unlocked the door to his motel room and opened it and ushered me in ahead of him. As I walked in, I surveyed every inch of the room before me. It wasn't much, a queen bed in less than impressive bedding, a TV a few years too old that sat on a dresser that was peeling paint, and a bathroom that currently had its light off but couldn't have been much of a sight anyway. It wasn't much, but it was still something I had been dying to see for some time now. It still excited me to finally have it revealed and be in its full presence.

Big Bobby shut the door and locked and latched it, for our safety he assured me. The motel wasn't in the greatest part of town so I didn't think much of it.

"Take a seat on the bed. I'll get us a drink."

I tentatively took a seat as he turned on the TV and put on one of those 80s action movies where the guys have bulging muscles and glisten with sweat for more than half the movie. I thought we would have a quick beer and then I'd take off, but then he pulled out a full bottle of bourbon from one of his bags and grabbed two plastic cups off the decrepit dresser.

"On the rocks?"

"Sorry?"

"Ice? Or no ice?

"Um, ice, would be nice."

"Some nice ice coming right up."

He smiled and went over to an ice bucket that sat on a side table next to the bed. If there was ice in there it must have been sitting for hours. He pulled out a few half melted and slippery wet cubes, put them into each cup, and then topped them off with a heavy pour of bourbon. One of the cups was placed in my hand as he sat next to me on the bed. I took a few sips as Big Bobby nearly guzzled down the whole damn cup of brown bourbon. He encouraged me to drink more and more over the next few minutes and even went as far as giving me a refill before I had even asked for one.

We talked just a little bit more, but things went quickly quiet after that. His eyes went either to the bulky and beefy men of 80s movie fame, or on to me. I felt his eyes looking me up and down as the effects of the bourbon started to wash over me. It was definitely causing me to feel a bit light headed and out of sorts, but I didn't want to admit it to the strong man beside me. It was Big Bobby after all, a man you would try to impress more than anything.

He gave my cup another heavy pour and pushed me to take a few more reluctant sips and gulps as the movie started to wind towards its end. I thought that would also mean the end of our evening as well, but I soon found out that Big Bobby had other plans. He leaned forward and turned the TV off and then leaned back right next to me. He felt closer than he had originally been but it might have been my imagination. As I sipped a bit more of the now warm bourbon he finally broke the silence in the air.

"It's a shame Mary wasn't in town."

"I guess. I mean I guess you had plans for her."

"Indeed I did. I bought her a new dress and everything."

"Did you?"

"Sure did. You like to see it?"

"Uh, sure."

He got up and grabbed one of his other bags and placed it on the bed. From it he pulled a black dress, what looked to be a tube top dress. I didn't know much about women's clothing but it didn't have any straps or anything and looked to be of a fine and soft material. I reached out and touched it and confirmed yes, it was extremely soft.

"You know, I just had a crazy thought."

"What's that?"

"Well it would be a shame to let the dress go to waste and all. And I was really hoping to see how it would look on her..."

"Yeah?"

"Now I'm no queer mind you. But would you maybe want to try it on and model it for me?"

"What?!"

"I'd pay you, of course. A hundred dollars?"

"Seriously?"

"It just looks like you and her have about the same frame is all. I was just curious."

"I don't know, Big Bobby. This is getting kind of strange."

"How about two hundred then?"

"Two hundred?"

"For just a minute or two. Hell, you can't turn down a quick two hundred like that can you?"

He reached into his pocket and pulled out two slightly crumpled one hundred dollar bills and placed them on the bed in front of me. It was a good little sum of money. For me it was a good little sum anyway. I didn't quite know what Big Bobby was up to, but if it really was only going to be a few minutes, then I'd be a fool to turn his offer down.

"Okay. Sure."

"Really? That's great. That's so darn great of you."

I took the two hundred off the bed and he was quick to put the dress in my hands. I'm not sure why I had agreed so readily, the bourbon was certainly a help, as well as the decent little sum of money. But the real reason I think was not only did I want to see the inside of this motel room, I wanted to feel in some way what Mary felt when she was in this room. If I could wear this little dress for even a few minutes it would certainly help in enhancing that particular feeling. I wasn't going to do anything further, I wasn't gay or anything, but if I modeled the dress for him and then saw a look in his eyes, a look he would give Mary, then I would know even more of her experience.

I took the dress and went into the tiny bathroom of the motel room. I turned on the light and revealed that yes, it wasn't much to look at at all. Before I closed the door, Big Bobby reached his hand in and held out a pair of black stockings for me to take. I paused and didn't know what to do.

"Just to help the effect." He said, and then added, "If your legs are hairy, that is."

I reached out with reluctance and took them, but I said, "That better be it."

He agreed. And I should have known better.

I placed his items on the sink and started to strip my clothes off. I didn't know if I should leave my boxers on or if they would fit under the dress. I decided to leave them on as I surely wasn't going to go commando. Once the boxers were the only thing I had on, I looked at the stockings and thought it would probably be best to slip those on before trying anything with the dress. I sat on the toilet and started to slide one up my leg. I did have leg hair, which was apparent but a light color, but I guess it made more sense to wear them for the overall feminine effect.

After I slid the second black stocking on I heard a knock on the door. I went and opened it a crack and I could hear Big Bobby's heavy breath.

"Sorry to bother you again. But I want you put these on as well."