Then and Now - On The Road

Prologue

It's a Sunday evening in late June 1999. I'm on the road for work, staying in a cheap motel room in Memphis, TN. I arrived here late Friday Night, giving up my weekend to get here two and half days early. Saturday Morning I began surveying the site. My worst fears were confirmed.

This was supposed to be a one week job, commissioning a new, Y2K ready, server based system to replace an old mainframe system. Most of the prep work was supposed to be done already by the local contractors.

It wasn't and things are not good.

I'm on my phone with my boss. I'm telling him what I've found.

He doesn't see the problem. We actually have three weeks before we need to deliver the system. He tells me to stay the extra two weeks and finish the job.

I refuse. I tell him to send someone else.

There is no one else, he says.

Not my fault or my problem, I say. He is, after all, the one who over promised and then got cheap and created the mess we are now in.

He tries to appeal to my sense of duty, my sense of responsibility, my sense of camaraderie, my sense of pride, even my sense of humor. Nothing works. Then he actually tells me I need to "be a man" and "step up and take one for the team".

I actually laugh at that. Taking one for the team is what lead to my divorce, I tell him. Too many late nights at work. Too many working weekends. Too many unexpected trips halfway across the country to fix someone else's screw up. Just way too many for "the team". I am a man; a tired man.

He threatens to fire me if I don't agree.

I remind him of all the other Y2K jobs we have lined up that need to be delivered in the next six months and that he's already short staffed and behind.

Besides, On January 1, 2000, the Y2K boom will be over. He's going to lay me off on January 2nd anyway and we both know it.

There's silence on the phone for a few seconds and then he appeals to my sense of greed.

That works.

I realize I have him over a barrel.

I'm not sure the job can be done in three weeks, I tell him. I want a guaranteed three months salary bonus in addition to my regular salary if I stay, even if I can't complete the job on time. And another three months on top of that if I pull it off.

He curses. We're both quiet. He curses again. More silence. He says I have a deal. Then he calls me a name my soon to be ex also calls me and hangs up.

I lay on the bed and ponder what just happened. What I just did. I'm usually a more agreeable, almost passive, guy. I guess I've just had enough.

To my surprise I realize I am hard. Really hard. Rock hard. My dick, that is.

It's the first time in three months. I know that's not normal for a 32 year old guy, yet I refuse to see a doctor. It's too embarrassing and I figure it's probably just stress from work and the divorce and whatnot.

I look down at the lump in my pants. I rub my hand against it. Fuck, that feels good. It feels good to rub my hand against a hard dick and to have a hand rubbed against my hard dick. Even if they're both my own.

I consider jerking off.

Instead I get up and go out. It's Sunday night, after 11, in Bible-belt Tennessee. I don't know the area. I'm not sure what's out there, what's open or what I can find.

We're right off I-70. There's a gas station with a 24/7 coffee shop across the street. It's basically a cut rate Dunkin' Donuts knockoff. Maybe they can point me in the direction of a little action. Or maybe I can pickup a waitress. Or a busboy. Or both. Or Whatever.

Even though I'm not rock hard anymore by the time I get to the coffee shop, I still have a fairly solid chub. I adjust myself before I walk in, pushing my cock down the left leg of my pants so it isn't blatantly obvious. You can still see it, you just actually have to look.

I walked into the restaurant and looked around. There was a waitress, a white woman who looked to be in her mid-to-late forties, sitting behind the counter reading a novel. She wasn't bad looking. She had big tits straining against her uniform polo-shirt, dark black bra obvious under the white fabric of the shirt. The polo was unbuttoned to show cleavage. They had the weird, wide gap common to fake tits. Long danglely earrings. A dye job with reddish highlights. Brilliant red fingernails. Certainly a little trashy. A cougar, maybe. Definitely fuckable. Probably fun in the sack. She might appreciate some slightly younger dick in her. Some potential there, I thought.

I glanced at the book. The cover was a lithe brunette sitting at the feet of a muscular, blond haired, bare chested, man. He held a big sword. She was clinging to his thigh. He was looking intently at something off the cover of the book. She was looking intently at his crotch. Ah, the subtle art of a paperback romance novel. Soft-core porn for sexually frustrated, middle aged women. Oh yeah, some real potential there. I walked toward her with a smile and cleared my throat.

She didn't look up, she just she called out, "Customer!"

'Must be a good part,' I thought, 'probably something about the hero's throbbing manhood.'

There was only one customer aside from me, a skinny, dark skinned, black woman, wearing a tight half-t that showed her toned belly, tight capri pants flip-flops and a bandana tied on her head. She was sitting at the counter talking on a flip phone. She was nodding emphatically as if the other person could hear her head move over the phone.

"Mmmm-hmmmm, yes, yes, oh yes" she went on, "That's what I said. Girl, I told him to take his cheap-ass-stinky-ass cologne and get out."

I realized the skinny black woman was a guy. A skinny, very femme guy. Okay. Interesting. Maybe. If all else fails.

I sat down at the counter, a few seats away, not too far, not too close.

He looked me over as I sat down, eyes hit my crotch and went a little wide. "Listen, Girl, I have got to go," he said into his phone, still staring at my crotch, "something has, ah-hem, come up." He snapped the flip phone shut with a dramatic flourish and looked at my face.

"Well hello there," he said with a smile.

I smiled back. "Hi"

Just then the another waitress walked out of the kitchen. A black girl with a creamy mocha complexion, maybe all of 21 years old. Cute. She had smaller tits than the white waitress (smaller but certainly not small) and they looked real by the bounce. Wide hips. Not fat - Curvy. What black guys in the warehouse at work called "thick". She had her polo buttoned all the way up to the collar. A plastic name tag hung on her left tit, probably right over the nipple. It read 'Hi My Name Is: Shanna'. Real talent there. Great potential.

"Elle," she said, "quit bugging the customers."

The guy next to me, apparently Elle, spoke up with fake indignation. "I ain't buggin' nobody, Cuz.," he protested, head bobbing back and forth, "I'm just sayin' hi 'cause apparently all-ya'-all are too busy to do yo' jobs."

The white waitress spoke without looking up from her book. "Keep it up, Elroy, and you'll get banned again." My opinion of her changed from "possible cougar" to "likely bitch". Much less potential. Still, I wouldn't have said no.

The black waitress, Shanna, looked at me. "What can I get you?" she asked with a smile. It was a practiced, generic, professional waitress smile. Perfectly pleasant yet vacant. Behind that smile she could have been thinking about her taxes or how to get grease stains out of her shirt. I knew that smile, I used the same one with clients everyday. I was actually using it ever since I walked into the coffee shop.

"Black coffee," I said, "chocolate glazed donut."

If she caught the double entendre, she ignored it. Elle/Elroy caught it.

"Choc-Oh-Lit Guh-Layzzz-D Dough-NUT," he repeated. We looked at each other. He slid over another seat closer to me. His smile looked genuine.

Shanna put down an empty mug and a plate with the donut in front of me. She apparently still didn't get it. "Anything else?" she asked with her professional waitress smile as she filled the mug with hot coffee.

What I wanted to say was, "Yeah, some squeezings from your pussy to sweeten my coffee." What I actually said was, "Now that's a loaded question."

She rolled her eyes at me and let her smile slip just a little. It was look of tired amusement mixed with mild exasperation and maybe slight annoyance. It too was a practiced, professional waitress expression. It was a skilled look, a true professional waitress look that said "back off" without being obnoxious to the customer.

I'd gotten that look before. I sighed inside.

"Sorry. Just tired and a little punchy, I guess. Seriously, nothing else, thanks. I'm good."

I wasn't getting any play from her. Obviously her defenses were up; she probably got hit on all day, everyday. Talent but no potential for me there.

Elle was leaning on the counter giving me a dreamy look. "So what's the best part?" he asked, "The Chocolate? The Guh-laze? Or maybe it's the hooooole?"

Shanna's eyes went wide. That was a genuine look. She got it now. She called out "ELLE!" in shock and maybe a little amusement. The other waitress, the whose name tag I hadn't seen, just said, "Last warning, Elroy." She still had her nose in the book. In my head I named her Fake Tits.

Elle put his hands up. "Alright, alright, I'll be good," he said. "A boy's just trying to have some fun, is all."

Shanna gave him look, shook her and and put down my bill before she went back into the kitchen. She actually seemed a little amused by him.

Fake Tits still had her nose in her book.

I laughed and looked at the guy. One seat separated us. I could have sworn it had been two seats a second before.

"Elle, right?" I said, "It's just a donut." I was such a liar back then.

"Mmmm-hmm," he said, "and sometimes a cigar is just a cigar. Or so they all try to tell me." He slid into the seat right next to me. "So you know my name, Sugar, what's yours?" he asked placing a hand lightly on my thigh.

"Fred," I answered without reacting to his hand.

He pushed his hand forward and squeezed my semi-hard cock through my pants. "I think we should call you Mr. Big Stuff."

I still hadn't quite given up on either of the two women there. The further I let things go on with Elle, the less likely pussy was. I picked his hand up out of my lap and put it back in his. "No offense, but you're, ahhhh, not my type, Elle."

"You sure about that, Sugar? How do you know if you ain't never tried?" And then he lowered his gaze and his voice and asked, "Or have you?"

Fake Tits slammed her book down on the counter. "That's it, Elroy, time for you to go." She was glaring at him as she spoke. "And don't come back for a week."

"All right, all right, Bitch, I'm going. You ain't have to tell me twice." he said as he collected his stuff in a bag that was almost. but not quite, a pocketbook. And then under his breath he muttered, "Nobody likes your nasty-ass coffee and fake titties no-how."

Fake Tits was red in the face. "Make it a month, Sodomite!" she yelled, a little vein twitching in her forehead, as Elle strutted out.

Shanna had come back out of the kitchen and watched, silently, obvious distress on her face. Fake Tits wheeled around and, staring at Shanna, pointed to Elle's unpaid check on the counter. "That," she said, "is coming out of your pay. You're on this ice around here, too."

I reached over and picked up the check. $7.30. Mine was $1.95. I opened my wallet, pulled out a $20 and dropped it on the counter. Fake Tits was now glaring at me. I looked at Shanna, thought for a second, pulled out my last $17 and dropped that on the counter, too. I glared back at Fake Tits. "That's for her," I said, pointing at Shanna, "All of it."

I looked over at Shanna and said, "Sorry." It was all I could think to say before I left.

I started walking back across the lot. The night was a bust. And I was probably persona-non-grata at the coffee shop. Oh well, I figured, there would be other nights and there were other coffee shops. Plus, as Elle/Elroy had pointed out, the coffee was kind of nasty.

I was just about to cross the street when I heard Elle's voice, "Hey, Mr. Big Stuff." I turned and saw him. He was leaning against a car almost like he was waiting for me. I gave a little waive.

He sauntered over. He moved smoothly, like a cat. "I saw what you did in there," he said, "Ain't gonna' get you nothin' from Sha, tho. She's a good girl. She's my cousin, so I know. Still nice of you tho."

"I wasn't trying to get anywhere with anybody," I answered, "that just seemed wrong. She didn't do anything wrong. Nobody did."

Elle laughed. "Puh-leezzee... I saw the way you was looking at all those titties in there, eyes bouncing around like you was watchin' tennis. Oh, and 'black coffee and a chocolate glazed' and 'Golly, that's a loaded question'? Bitch, Puh-leezzee..." He didn't a pretty fair Gomer Pyle impression when he quoted me.

I laughed back. "Well, you can't blame a guy for trying."

"Mmmm, no, Sugar, you sure can't. No, you can not," he replied, eyes dropping to my crotch.

The offer was obvious. There was no need to flirt or sweet talk or try to read any signals. After what just happened I wasn't in the mood for games anyway.

I looked back through the coffee shop window. Fake Tits had her nose back in her book. Shanna was nowhere to be seen, probably back in the kitchen. Even if shit hadn't gone down the way it did, I wasn't going to get laid by either of them, anyway.

I kind of had the same feeling I did earlier on the phone with my boss.

I didn't even look back at Elle, I just turned and headed back toward the motel. All I said was, "Come on."

"Mmmm, you do know how to sweat talk a girl..." he answered. I could hear his flip-flops smacking his feet as he ran after me.

Like I said, I hadn't had a proper erection in months and I hadn't cum either. And I hadn't had dick in a few years. As I walked I realized I really wanted Elle's dick, maybe more than pussy right then, it wasn't just a "consolation prize". My own dick was rock hard when we got to the room.

As soon as the door was closed he was on me.

He grabbed me from behind and reached around to feel me up through my pants. He dry humped my ass, grinding against me hard. It felt good. He kept doing it and I just ground my ass back against him. I wondered if he was going to cum in his pants that way.

He backed off a little and turned me around to face him. He hugged me and held me tightly. I hugged him back. I was around six inches taller than him. His bulge pressed against my thigh, mine against his stomach. For just a minute we stood there like that with his head resting on my chest.

He lifted his head from my chest and tilted his face up to mine. He put a hand on the back of my head and pulled my face down to his.

Our lips pushed together. He forced his tongue into my mouth. I let him. I let him be in control, at least for the moment. I wondered what we were going to do and only got more aroused.

I ran my hands down his back and squeezed his ass. It was a nice, firm bubble butt. My soon to be ex-wife would have killed for an ass like that. Lots of women would.

He pulled off my shirt and I pulled off his. He was thin with tight muscles that weren't big but were well defined and toned. He stood in front of me and I caressed his chest. He was almost hairless. His skin was dark brown. Smooth. Tight. Soft.

I bent my head and licked and sucked his nipples. He made little sounds of pleasure.

He left his hand on my head and with the other rubbed himself through his pants. I swore I could almost see the tip of his cock-head peaking out of the waistband. The poor guy, it must have been so uncomfortable.

I dropped to my knees. He rested both hands on my head. I unbuttoned and unzipped his pants and pulled them to his ankles. I wasn't really surprised to see he was wearing women's red lace panties that failed to contain his lovely dick. His balls spilled out either side and the top half of his shaft was exposed.

I gently kissed each ball and licked the tip.

"Oh, so is that the way it's gonna' be?" he asked.

I didn't answer. I pulled the panties down to expose him fully. Once free of the panties, his dick pointed almost straight at me. He stepped out of his pants and kicked them away while I admired him.

His was a little longer than mine. While I was about 7.5", he looked just about 8". Yet his was also thinner than mine. The shaft was thinner at the base with a slight twist to the left and got thicker toward the head. It made his cock head seem huge, although it really wasn't that big.

I inhaled deeply through my nose. The smell of his sweaty black balls was perfume.

"You want it, Baby? You know you do," he said, "all the white boys do."

"Yes," I replied, my eyes fixed on the lovely black shaft in front of me, "we all do."

"So say it, Baby, tell me you want it."

"I want it," I said. And then I looked up at him.

"Ask for it."

"May I? Please?" I asked.

All he said was, "Mmmm-hmmmm, open your mouth, Bitch" as he put his hands on the sides of my head and guided me toward his crotch. I opened my mouth and stuck my tongue out to accept him like an alter boy accepting communion. To me it was every bit as divine as any other blessing.

Just like that I had gone from "Baby" to "Bitch".

I kept my mouth open wide so the bottom of his shaft slid along my tongue was all that touched me until the head of his cock just barely touched the back of my throat. "Close your mouth, Bitch" he said.

I was Elle's bitch.

I closed my mouth as instructed, my lips pressed firmly to cock.

"MMMMMM. That's it," he said, "now you hold still and suck that like a greedy puppy suckin' on his momma's teat. Got it, Bitch?"

With his dick in my mouth all I could do was nod a little and mumble "umph-hum" around it.

He held my head firmly as he began to sway his hips back and forth, fucking my mouth. I kept my hands at my sides, passively accepting him.

He said nothing, just an occasional "Ohhh", "Ahhhh" or "Mmmmmm".

He was careful never to go too deep. He would just reach the back of my throat, almost make me gag and then pull back. I don't think he ever got much more than half, maybe 3/4's of his dick into my mouth.

'God,' I thought, 'he's good at this. I hope he likes it. I hope I'm doing good. I wonder if he's going to cum this way.'

It went on for a few minutes like that and suddenly he pulled back and stopped, just the head in my mouth. I could taste salty precum. I started to move my head forward and back, I wanted his 'glaze'.

He pushed me away and stepped back. "No," he said, holding my chin in his hand and looking down at me, "not that way."

He composed himself. "Bitch, not I know that ain't your first time with no dick in your mouth. Is it, faggot?" he asked, still looking down at me.

"No," I said, looking into his eyes, "You're better than any I've had before though."

"What do you need, Ma'am?" I asked. It was obvious he liked it when I called him "Ma'am"

He guided me to my feet and told me to get naked, so I did.

I stood still while Elle walked around me, inspecting my naked body. He felt my arms, my legs, my chest, my ass, my balls. He had me bend forward and I leaned against the desk while he ran a hand up and down the crack of my ass, pressing a finger tip against my asshole and letting it linger. I didn't react. "She's tight, Bitch," he said and asked, "are you a virgin, White Boy?"

I was honest when I answered, "No, just not often and not in a long time. A very long time. Years."

The fact that he referred to my asshole as "she" wasn't lost on me. Neither was the fact that he asked if I was a virgin and was now calling me "Bitch" and "White Boy". I realized I was going to get fucked if I didn't take control soon. I wasn't sure how I felt about that. I could have let it go either way.