The Virgin Voyage
Note: This is a chapter from an as of now unnamed novel I’m working on.
June of 1991 was a big month in my life. Sure, I was only 19 then, but I still had finally earned the trust of my employer for an out-of-state haul, even if it wasn’t that much further than the in-state drives I’d been doing for 18 months. But still, this was big.
I’d graduated from high school at 16, a whiz kid learner, some would say genius, but I was bored with school. Spending all my time in gifted classes and events while other kids went to parties and were making out was frustrating, so I rebelled by not filling out any college applications. My mother, furious with my decision, declared that at 18 I had to be in college or get out.
October 17, 1989 came and went and by the end of that day, I was 18 years old and had to take a bag to my Cousin Lenny’s studio apartment around the corner from 8th and Pine and sleep in a corner that wasn’t occupied.
Lenny, 18 years my senior, was like the big brother I never had — annoying, loved to needle me, but helpful and there when I needed someone the most. So the Friday after I got kicked out, he took me to his job, a small, Black-owned shipping company over Northside called Williams Express. The owner, Donald Williams said “Sorry kid, we’re only looking for a couple of drivers right now. I doubt you even have your CDL.”
A light bulb went off over my head. A truck driver! I could always do that. I loved yelling for truck drivers to tug on their horns whenever they came bounding through Eastside and I figured learning how to drive those beasts and making decent money would be fun.
“What if I went and got my CDL, Mr. Williams? Would you consider me then,” I asked.
He chuckled at the quick gears turning in my head and replied, “Go for it.”
I took the savings from my previous job, cashier and all-around gopher boy at Ricky’s corner store and laundrymat and spent weekends catching the Amtrak back and forth to Philadelphia and a truck driving school that was pretty much 18-wheeler boot camp. Our instructor was a grizzled veteran of the highway, an old Czech immigrant named Stanislav Burkowski and “Scowlin’ Stan” as we came to call him had no patience for the smallest mistakes, even from an 18-year old nerd like me.
“GODDAMMIT Gilliam,” he’d growl, “You know you have to set the mirrors so you can see what the hell’s on the side of you. And sit up straight in the cabin. This isn’t a motherfuckin’ Cadillac.”
Safe to say I was relieved and happy to graduate near the top of Scowlin’ Stan’s class after getting a perfect score on the written exam and driving to Harrisburg and back to his satisfaction. By the summer of 1990, I was working for Williams Express, but I wasn’t driving big rigs just yet. I made smaller treks around Delaware — or should I say up and down, seeing as it’s really the only two directions you can go — in a cubed van, but I kept my eyes on the prize.
The prize finally came the first week of June when Mr. Williams pulled me aside and said “Shawn, I need you to make a run to Easton, Maryland this weekend. For that, you’ll need a big rig, so I need you to sign it out, sign it back in with the mileage and here’s all the info you need.”
I couldn’t believe it. My chance had come. I was looking forward to getting behind the wheel of one of the new Kenworth T600s Williams Express had just brought in. Sitting high with a sloping nose and a huge sleeper, the T600 was “The truck of tomorrow” favored by a lot of the old drivers I talked to. I imagined myself looking cool, wheeling that brand new technology down Route 13 to Easton.
Instead, Mr. Williams guided me towards Ol’ Betsy, a 1969 International Harvester Transtar II cabover. The truck of tomorrow Ol’ Betsy was not. The cabin was small and with me being 5’9 and 230 pounds, the sleeper was not fit for the husky type (read: me). At 22 years old, that truck had seen its better days with its black and gray paint faded in spots that made it look it like a cow. The original Williams Express logo struggled to hang onto the doors. And the engine, oh God — a noisy son of a bitch Cummins Detroit Diesel 6V-71 that made you hard of hearing before you even left the yard.
Like or not, Ol’ Betsy and I were about to be road dogs and after getting over my disappointment, I realized this was a big opportunity for me to prove that I was a reliable driver, ready for the road and anything that came with it.
And I would be tested in very short order by everything the road had to offer.
After making sure the trailer was nice and secure, the tank was full, my mirrors were set, and yes, sitting up straight, on Friday June 7, 1991, I pulled out of Williams Express and onto I-95 South, heading to drop off processed food to a grocery store in Easton, Maryland. A beautiful Friday afternoon was the perfect backdrop as I motored along, the Cummins engine hollering in my ears. Traffic wasn’t bad yet because all the beach folks didn’t take Route 13 until about Delaware City, so I prepared myself for that bullshit by singing old songs my grandma used to sing.
My Gramma was my best friend. She cussed my mom out when she kicked me out and offered to let me stay with her at her high-rise apartment. Instead, Cousin Lenny said it was cool if I crashed with him, but Gramma and I stayed close and she prayed for me before I hit the road that day. That would come in handy sooner rather than later.
I reached a truck stop in Middletown, Delaware on Route 301 shortly before sunset because I had to piss like a racehorse and I was hungry. I was fat, of course I was hungry, but as I walked to the counter after using the bathroom, my stomach rumbling soon gave way to my underwear jumping.
One thing I came to learn was that truck stops had the most interesting and weird people hanging out there. Pretty girls were always the featured attraction and one of the few girls that wasn’t a blonde-haired White girl shot me a glance. Peanut butter complexion, cat eyes, jet black hair and a petite body poured into a black crop-top vest and blue jeans. She looked like she was about 22 or 23, a few years older than I was.
As soon as she spoke, it was clear she was Puerto Rican, Cuban, one of them shits. All I know is she hypnotized me within the first sentence she spoke.
“You must be new around here Babyface,” she said, full of spice. “Neva seen you around before.”
Not one to get nervous around women (at least on the outside), I pulled myself together and said “Yeah, I’m on my first run for my job. Just stoppin’ through to get some grub and get back on the road.”
“Where ya goin’? I could use a lift down to Easton. That is, if you won’t get in trouble,” she hinted.
The other drivers and women over at the bar were watching us closely. The hardened drivers were either envious or amused at this husky newcomer flirting with one of the fine young thangs of the stop. Meanwhile, the women were watching her intently, almost as if they were grading her pick-up skills.
I thought about Mr. Williams telling me that a stop was cool, but I still had to be at the Easton Market at 7 a.m. Saturday. It was 7 p.m. that Friday night. 12 hours. The possibilities shortened my breath, tightened my pants and almost dried my mouth until I took a sip of the can of Pepsi I’d got from the soda machine.
“Easton’s where I’m headed,” I said in the coolest voice I could come up with, thinking I sounded like Barry White but was probably closer to Keith Sweat. “You can ride with me.”
She smirked seductively and her accent got lower, huskier and sexier. “Great,” she said. “Let me just grab my bag and I’ll be ready to go.”
15 minutes later and the only noise coming from the cabin is the growl of the engine. I’m not sure how to approach any subject at this time. Remember, I was a high school nerd and didn’t talk to girls often. So yes, at this point, I’m still a virgin. I say at this point because it only gets wilder from here.
“You don’t say much,” she said. “You haven’t even asked me my name. That’s something you wanna know, right?”
I chuckled at my own shyness and said “You’re right. I’m Shawn and you are?”
She said it slowly so I could understand. “Ahn-hell-lee-kuh. People think my mami named me after that white actress lady from The Witches, but it’s spelled A-n-g-e-l-i-c-a. And I’m cuter.”
I laughed and said “Yeah, you’re fly. So what made you wanna get a ride with me?”
“Well none of those old gringos in there wanted to look my way and I really have to get to my cousin’s house for her baby shower tomorrow,” she explained. “And you’re a cute Black papi. I don’t see those very often.”
My coffee brown skin was as close to red as it could possibly get. “Well thank you, Angelica. Maybe I’ll run into you before I head back North tomorrow.”
She sighed and rolled her eyes. “You really ARE new to this, aren’t you? Pull over in about three miles.”
“Three miles,” I repeated curiously.
“Pull over in three miles,” she repeated. “Jesus, I hope I don’t have to do EVERYTHING tonight.”
My nerves were really frazzled and my heart was racing too fast for words as I pulled over to a very deserted part of 301 as Angelica had instructed.
“Cut your lights off and let’s get in the back,” she ordered. I did as I was told. Even though Angelica was about 4’11, there still wasn’t a lot of room in Ol’ Betsy’s sleeper, but told me to lay back and she slithered from my feet up to my face and started kissing me. I had kissed before, but Yvette Davis wasn’t trying to hear a damn thing about 2nd base, 3rd base or home on prom night. I took the liberty of running my hands up and down Angelica’s slim but sturdy body as we made out. I could hear a moan escape her lips as she lightly stomped her boot three times against the cabin. I thought she was getting excited and ready for action. BOY, was I wrong.
I heard some rustling, and then some dudes banging on the door with a handgun pointed square at my face.
“Out of the truck! NOW! Don’t get cute chubby,” a tall skinny white boy ordered and his two huskier redneck friends pulled me out of the truck and slammed me up against the side of it. I was scared to death. Was this really about to be the end of my life? I heard Angelica sneak out passenger side and hop down, but nothing else. I was breathing heavy, but refused to let them see me get weak. I just kept my hands up.
“I only got a few dollars guys,” I said calmly. “You’re welcome to it. I honestly don’t have anything else but this shipment of frozen food.”
“Boar, check his pockets,” Tall Skinny ordered one of his friends and Boar did, roughly, while my hands were still up.
“This nigger ain’t got nothin’ but 50 bucks,” Boar groaned. “Probably his gas money.”
“We should string your ass up on a tree and let you burn,” the other husky redneck hissed.
Tall Skinny began gnawing on his bottom lip and said “Guys…I ain’t goin to jail for 50 freakin’ dollars.”
“Well let’s kill his ass,” Boar shouted. “We’ll park the truck somewhere else and then just dump his body off Kent Island.”
Tall Skinny didn’t move.
“Randy, what the fuck dude! Are you pussin’ out?! SERIOUSLY,” Boar grumbled.
My hands are still up. My young life is still flashing before my eyes. I’m in no position to do anything. I hope my mom and Gramma know I love them. I hope somebody fights for justice for me after these rednecks kill me.
Randy suddenly lowers the gun and BOOM!
I recoil, thinking I’ve been shot, but there’s no holes. No blood. No loss of consciousness. For me, anyway.
Randy’s on the ground knocked out. The gun helicopters over to me. Boar and the other guy check on Randy. Standing behind them is Angelica with a tree branch.
“Bitch! You sold us out,” Boar said and as he and his other friend rush her, I pick up the gun and let it click.
“Let her go or I’m going to be the one behind bars,” I said. I have no idea how I held that gun steady in that moment, but I can tell you, seeing the fear in those punk motherfuckers’ eyes was the most powerful feeling I’ve ever had in my life. “Back off her,” I say again and Boar and the other guy grab Randy and shuffle off towards a rusty 1961 Buick Electra.
“You got lucky this time, nigger! Bitch, you better hope we don’t see you again,” Boar threatened, shoving Randy into the backseat of the Buick and peeling off.
I threw the gun as far as I could. Angelica looked at me. Stunned. Nervous. Guilty.
“You were setting me up to get robbed,” I said, full of disappointment. Learned a lesson the hard way tonight Shawn, I thought to myself.
Angelica was instantly apologetic.
“You’re right, I did,” she said quickly, “But I felt bad for you. I think I actually saw you as a real person and not just somebody to steal some money from. I’m sorry. I don’t blame you if you left me here.”
By then it was dark and I couldn’t leave her on the side of the highway. I just need to make sure SHE didn’t have a gun on her. I felt her for any extra weapons and all that was there was warm, soft skin. My dick got hard again. Even after a near death experience, I was still on the hunt for sex. Typical male teenager.
“I don’t have anything,” she said. “If you take me to Easton, I promise you’ll never see me again. OhmyGod, I don’t know why I did this.”
“Okay,” I said solemnly. “Let’s go.”
Turning off the 301/50 split into Easton about 45 minutes later felt like relief. I still had to find somewhere to park, but I was going to drop Angelica off at her cousin’s house as promised, even though she nearly got me killed earlier in the evening.
“So where does your cousin live,” I asked curtly, ready to get this nightmare over with.
Suddenly, Angelica spoke up, smiled at me innocently and said “You don’t have to take me there yet. I want to, umm…finish what we started.”
I looked at her like she told me Santa Claus and the Easter Bunny were real.
“You sure about that, because you almost got me shot an hour ago,” I said, annoyed, aggravated and almost ready to fight.
“Yes, I’m sure Shawn,” she answered. Again she seemed remorseful. “I meant what I said earlier — you are cute and I like the way you kiss. You have nice lips.”
Sucker, thy name is Shawn Gilliam. She had me again.
So I pulled over into another truck stop parking lot, after hours and leery of cops but if I survived a robbery, I could survive 5–0 catching me. I looked around before we got back in the sleeper.
Not long after I cut the headlights off and turned the sleeper’s dome light on, we were lip-locking once again and I again, started rubbing Angelica’s body down. No tapping with her feet this time. Instead, she broke our kiss, pulled her crop-top over her head and unsnapped her plain white bra to reveal round, smooth C-cup breasts with silver dollar-sized areolas.
“See something you like,” she teased. I stuck my hand out to touch one and she said “Si papi, touch it.”
Felt so good to the touch, I just went straight ahead with my lips and tongue on her left nipple. I felt her hands digging into my shoulders and her moaning vibrating against my forehead in approval. After a few seconds, she pushed me back up to a sitting position, unsnapped my jeans, reached in and I guess got the shock of her life.
“Oh mierda…Oh mierda…la verga grande, muy grande…oh mierda,” she murmured.
“What? Huh,” I said.
“You have a BIG dick,” she said plainly. “Oh my Gosh, please be careful with that shit.”
I don’t know if the girl was blowin’ smoke up my ass, but I looked at my shaft and head swelling, spilling over and dwarfing her long and slim hands and thought maybe she was telling the truth for once.
Instead of going straight for it, I remembered what an older friend was saying when he was bragging about how many girls he was taking down. “They like to be teased, Shawn. They like foreplay. Before you fuck, you gotta finger them first if you’re not gonna eat it.”
I helped Angelica wiggle out of her jeans as she kicked off her boots and pulled off her dark purple panties and tossed them to the front of the cabin, landing neatly on the gearshift.
Angelica leaned back on the bed and I positioned myself to her right, draping my upper torso against hers and resuming breast play with my mouth. I slowly inched my right hand down her flat stomach, spread her wiry thighs wide and eased my index and middle finger inside of her.
Her breathless gasp and loud sigh let me know I was getting warmer. Deeper my fingers went until I found a spot that felt just a little bit different than the rest of her. I started rubbing, motioning, pulling, back and forth, back and forth, back and forth.
Angelica’s hips swirled like a tornado and I kept probing, increasing speed along the way. I felt my fingers getting wetter, stickier, warmer until she dug her nails into my right hand, howled, shivered and shook for a few seconds. I took my fingers out and they were soaked and sticky, as if I stuck just those two fingers in a box full of freshly baked glazed doughnuts.
I was scared to ask, so I didn’t. I figured my fingers and her shuddering were evidence enough. I stepped out of my weather-beaten black classic Reeboks, took my jeans off and laid Angelica back on the narrow sleeper bed. Almost instantly, she slammed her hand against my stomach. “You’re gonna pull out when you bus’ a nut, right?”
“I am,” I answered quickly, only then remembering that neither of us had condoms.
“Okay, ease it in. Slowly. Slow — ah — wait a minute, waitwaitwaitwait…let me…okay, now…oh waitwaitwait…let me…okay, now…oh my Gawwwwd…”
As Angelica was getting used to my size, I was getting used to something I had never experienced before. It felt melted butter warm, maple syrup sticky and tighter than a blood pressure test. I realized I couldn’t just hover over top and inside of her like that, so I remembered from the endless supply of porno flicks I watched at Lenny’s house that dudes did a lot of thrusting. I tried to use as much of my back and hips as possible and once I figured it out, Angelica liked what I was doing.
“That’s it baby,” she whispered. “Just like that. Don’t stop.” The truck began to rock back and forth just as I was doing inside of Angelica and I started worrying about being caught. It was too good to stop. I ended picking up speed and her moans only increased volume and frequency.
Just as I felt myself getting into the groove, I also felt a familiar feeling rising up through my balls. I pulled it out and my own orgasm splattered against her left thigh in thick spurts and in short order. I thought I was fucking the hell out of her forever. It was actually 4 ½ minutes.
Angelica giggled as she took napkins from her purse and cleaned off her thigh. “Sooooo…I was your first, huh,” she asked as she continued chuckling.
Feeling too good to be embarrassed, but seriously out of breath, I panted “Yeah. First time for everything, I guess. Sorry I didn’t last that long.”
Angelica looked down at her small black watch. “Well we’ve got time to do it again. It’s only 11:38.”
I looked down and noticed that I hadn’t gone soft yet. It was one of the few things all those years of masturbation had given me — a short, if barely noticeable refractory period.
“I’m ready if you are,” I said. She looked down and mocked a dramatic faint and we both laughed.
The morning came and we were both sleeping our lives away in an awkward position. Angelica had fallen asleep on top of me and my right leg was entirely off the bed. I was surprised we hadn’t fallen over. I checked her watch and saw 6:15. Time to go.
“Here we are,” I announced as a pulled up to a nicely kept house in a not-so nice neighborhood in Easton. Silence.
“Shawn, thank you for last night,” Angelica finally said. “We got off to a rough start, but I think it turned out okay.”
“I’d say so,” I said. “I don’t know if I’m gonna see you again, but thank you for last night’s lessons. I learned a LOT.”
Angelica leaned over and kissed me on the cheek. “I hope you did. I learned something too.”
“What’s that,” I asked as she got out and hustled around my side of Ol’ Betsy.
“I’ll keep that to myself. Just take care of yourself, sweetheart.” She blew me a kiss and winked.
I had a smile a mile wide. “You too,” I could only manage to say as I started the truck up and headed for the grocery store.
I got back to Wilmington just in time for Lenny’s Saturday shift to end and we rode home in his Datsun B210 coupe.
“So how’d the trip go? No problems or anything,” Lenny asked me.
“Yeah man, A-OK,” I smiled as we pulled out of Williams and onto Lea Boulevard.
Lenny looked over at me and said “You got some on the road?! Was she bad? Did you use a condom?”
I got hype, ready to tell the story, then I remembered. “No man, I didn’t have any and she didn’t either.”
Lenny shook his head. “Boy, I’m gonna give you a stack for next time. You better hope you don’t start pissin’ fire or she comes up this way with a baby that looks like your puppy-dog eye havin’ ass.”
We both laughed and I settled back into the passenger’s seat and remembered thinking that a baby or an STD was the least of what could’ve happened to me on my virgin voyage. One thing was for sure, I was going to be better prepared for the next time around.