Holy Toledo

Author's Note: Okay everyone in the backseat, get ready for my slightly epic road trip. Lotsa sex, lotsa music, you know the usual. I just love a good ride, hope YOU like it too...

***

"I can't wait for you to get here, everyone wants to meet you."

"They do?"

"Of course they do."

"How many are coming to the party?"

"Um, around thirty."

"Thirty?"

"Don't be nervous, we have a big house I can hide you in the attic if you want."

"Okay. I will be fine in the attic."

***

'The trip, the best part, the part I like.'

I had the windows open. I was on a road trip to Nashville. I was going to the Johnny Cash Museum, hang out and drink the local beer, eat smoked BBQ, oh and go to a birthday party. My friend Anja was turning twenty-five on Saturday, September 28th. I haven't seen her in so long, four excruciating months, we used to be inseparable. I met her at NYU, she used to live in one of the tiny apartments scattered throughout downtown Manhattan, she lived under a bed.

"Are you wearing nail polish?"

We had so many classes together, we ate lunch together, and we loved the same music and colors.

"Um, no, I don't think so."

Anja was a pretty brunette and she was always in flannel. She was tall, dark eyes, she had a strong southern accent, she grabbed my hand, she pushed up my sleeve. She knocked over my water. "Y'all don't have any hair on your arm."

"Really? I'm, um, part Japanese." She was making me nervous, I wanted to go back to eating my wet chicken salad.

"Japanese." She was looking at me a little too suspiciously, I don't think she bought the Japanese explanation. I have known her for two and a half semesters, she asked a lot of questions, I was kind of used to it. "Let me see your toes."

My feet were under the table. The place we were eating, Eddies was quite busy for a Monday at two PM. I didn't want her to see my toes. "Sam, show me your toes!"

The three women sitting next to us, looked over, they were now paying attention, they wanted to see my toes too. I smiled, I shrugged, I was getting nervous. I didn't like people noticing me, it was no big deal. I shook my head at Anja. She grabbed my foot, unlaced my sneaker, and pulled off my sock, she was a pro at removing someone's clothes.

"Orange? You have red on your fingers, what the hell, don't you know how to match?"

***

It was Thursday afternoon and I was on Route 80, I was heading west. I had my old iPod playing through the speakers. It was attached by a long wire to the dashboard.

'It was the third of June, another sleepy, dusty Delta day

I was out choppin' cotton, and my brother was balin' hay'

It was really September, and none of those other things were happening. My phone buzzed, someone knew I was listening to this song.

"When you getting here?" Anja, was calling, she always called, she was officially my best friend and she lived at least sixteen hours away from me.

"I don't know, I guess Friday sometime. I'm heading to Toledo."

"Toledo?"

"Mmm, my mother's boyfriend gave me directions, he told me this was the best route." I was hoping. I didn't really like my mother's new boyfriend, I didn't like the old one either. I could take or leave my mother too.

"Well, okay. Did you bring that pink dress?"

"Mmm-mmm."

"And the yellow one for brunch on Sunday?"

"Mmm-mmm. They are right next to me." I patted the bag.

"Good."

Anja was one of the few who knew I was a crossdresser, well, back then. My mother had an idea, but she never asked, she barely talked to me. Her motto was 'don't ask don't tell.' When Anja found out about it she was mad at me for the rest of lunch. She couldn't believe I kept this secret from her. I told her I kept it from everyone since I was young. When we were done eating she started to get a little too interested, she wanted me to get dressed up, she took me to the little apartment she shared with four other people.

"Everyone, come listen to me for a second. Sam here is now going to be a girl. Understand, I want y'all to be nice."

She dressed me up in front of them, I wore one of her short denim dresses, she painted my toes and fingers the same color. She put me in a matching belt and tight heels. She spent an hour on my makeup. That day they all met 'Sabrina.' We had pizza, shots of Jack Daniel's and Jägermeister, and I made four extra friends for life.

Beep, Beep. "What are you wearing now?"

"Um," I was driving in the right lane on the highway, I was keeping out of the way of trucks, I was having trouble looking down to see what I was wearing. "My black sunglasses, a black top, my maroon skirt, stockings, and those black high-heeled sandals you gave me."

"Color?"

"Mmm, my nails are long and beige again, all of them."

"And perfume?"

"Marc Jacobs Decadence."

"Perfect, I want to know you are here as soon as you drive down the block. I'll call later, bye-ee."

***

It was a busy week, I quit my job. I worked for Sony Records, I made no money in music publishing. I told my mother I was moving out. She gave me seventy-four dollars to help with next month's rent. She hated my long nails, and my short skirt.

I have been in and out of my mother's house since school ended in May. I still had boxes and my backpack just waiting to be filled again. I packed for my big trip. Anja wanted me to visit, she wanted me to move, she had been begging me for the last four months. She had been warning me since we met. She went back to Tennessee, she lived with her parents in a big house not too far from the Ryman Auditorium, close to Music Row, and lived in a touristy neighborhood. She told me I was going to love it once I was able to say 'y'all like her.'

This morning, I got up early and dressed in my mother's bathroom while she slept. I had been living here very discreetly and very seldom the last couple of weeks, I couldn't wait to get out. The night before I had my body waxed again, I loved that feeling. I loved slipping on stockings after a wax, it made me excited, it made me shake a little. I told Anja about the experience and she laughed at me, now she calls herself a pantyhose girl. It's the second thing she tells a man when she meets them, the first thing of course is what she would like to drink. It was always Tennessee Bourbon, on ice, neat, in shots, it didn't matter, the men did nothing but think of Anja's legs anyway.

She would tell all the men we met that I preferred stockings.

"Sabrina here, likes a little air on her thighs, a little breeze on her tiny panties."

The men's eyes would go right to my mid section, then move down my legs, they would linger at my heels. Anja always shook her head, she told me men were so easy.

She would ask me later that night, "So how long 'til you showed him." She was referring to my thick thighs, she thought she knew me and men so well.

"Right after that first drink, when he walked me to the ladies' room."

I also had my hair done for my drive to Nashville. I had been growing it for almost three years, my mother hated it. My hair was so long and blonde. I had it dyed a lighter blonde with lo-lights. The guys at the salon parted my hair in the middle, made it a little wavy at the bottom, and then fluffed it up. They added extensions and it came down to my back. I loved swirling it around my face and flicking it over my shoulders. It cost so much more than seventy-four dollars. My pocketbook was running on empty, but my confidence was high.

Anja took me to this salon while we were still in college, it had no name and a rainbow flag outside and she told me to relax. I was wearing low heels, a pair of her skintight jeans, and a white top that said 'Nashville Babe.' She thought it was so funny.

"You're not even from Nashville, ha."

I had been going to the salon ever since. There was always someone new working there. They still gave me the student discount and I always brought in Italian cookies. My mother's house was in Bay Ridge Brooklyn, fourteen stops away by subway. I was surrounded by pizza places and bakeries. I made so many friends at the salon and sometimes I stayed and went out for drinks with them, I always called Anja, always told her I was having fun, but not as much as I had with her.

"I bet no one ever brings up your thighs, am I right?" She would tease me.

"Your right, we are talking about Vietnamese food."

"Same thing."

The guys and gurls at the salon usually took me to a bar called 'Courage' it was right around the corner from the salon. It was bright and there were mostly gay men who came in. I felt like a novelty until one of the local drag queens sat down. I always felt more comfortable with the queens even though I was so unlike them. Anja knew I liked straight men, I considered myself a straight 'woman' when dressed. She didn't understand it either, but she made me break up with a woman I was dating from one of our music classes anyway. She made me buy her flowers and tell her 'I'm finding myself.' Then she made me sit behind her for the rest of the Semester, so at least SHE could always find ME.

"Sabrina, you have to focus on what you really want, really like, y'all have to stop messin' about." She would give me these pep talks while the other four students in her room were on their phones, or highlighting, or eating ramen. She would be tweezing my eyebrows or making cleavage. I would get glances from the guys, they always tried not to stare.

Some nights she would put long nails on me, that was my absolute favorite. She would paint my nails and then make me paint hers. Sometimes she would even fix my hair, then once she surprisingly pierced my ears. I looked way too feminine to go to my mother's house, too feminine to even take the train back and forth in NYC. So I would stay over those nights, in this crowded apartment, I slept on the recliner. Sometimes one of the guys would lay with me, Anja said it was good practice. I would slip my hand with my long brightly colored nails into his pants. Sometimes we would still be talking to the others. I would play with their cock, I would lay on their chest, I liked doing this, it was fun. I would slowly rub them in my hand, my other arm usually underneath them, the recliner was tight. I would rub and tickle, I would push my palm down on their hard cock. I loved the feeling of it, but I had never seen them, the cocks were always hidden, I didn't want them showing themselves to the others, I wanted them to stay modest while they moaned. Everyone had on earbuds anyway. The guys would play with my hair, I liked that. They would kiss my cheeks, rub my breasts, play with the fabric of my skirt or dress. It didn't take long before they came all inside their briefs, all over my palm. Anj said she heard through the grapevine that I had good technique and soft hands.

The guys were always so appreciative, afterward, I showed them my thighs. I felt obligated. The next morning I always made them all breakfast.

Anja told me they talked about me constantly when I was gone, I was very popular in that tiny crowded apartment. They would ask each other what my nicest outfits were, they would talk about my heels and how sexily I crossed my legs, the scent of my perfume. I think Anja was a little jealous, but it was good for me, good for my confidence, it made me feel like I was reaching some sort of goal. It made me feel like a girl.

***

"Thank god!"

I finally saw the signs for Toledo, I felt like I was in Ohio for so long. I had been on the road for over eight hours. The car was making a weird noise, it was old, it was left in front of my mother's house by an older boyfriend. I sort of stole it, inherited it, whatever. It was powder blue, it was ugly, but it was great on gas.

'And mama said to me, child, what's happened to your appetite?

I've been cookin' all morning, and you haven't touched a single bite'

I was starving, I was still listening to music, the phone buzzed.

"Sabrina, where are you now?"

"Mmm, right outside Toledo."

"I wish you flew, you would be drinking with me right now." I heard her gulp.

There was no way I was flying in a skirt, especially alone. I could barely make it to the salon a couple of stops by train by myself. Anja wanted me to make this trip as a female, bring only female clothes, and have only a female outlook. She sent me money to take a flight but it now sits in an envelope in my backpack, ready to give back to her.

"I know, I'm sorry, but what's another day?"

"Okay then, don't get your panties in a bunch, where are you staying tonight?"

I started thinking, I didn't know, I didn't have money for a hotel. "I guess I will stay in the car."

"The car, what are you crazy, what are we back in college?"

***

Our last year in college, we were out of control, we thought we were so hot, so funny, too sexy for the bridge and tunnel crowd. This of course was after a couple of Tennessee Bourbons. I preferred beer or wine but Anja needed something that reminded her of home. We met with so many boys, so many guys she knew from college. I don't know how many men she caught me making out with, hidden in the darkness of the bar. I would have my hand on their faces and another on their shoulders, their tongue halfway down my throat. Our bodies would be close, I would smell their toothpaste, and I would suddenly feel a tap on my bare shoulder.

"Sabrina, last call." She would laugh and call me a slut late that night. I would be banished to the recliner, I would ask one of the roommates to join me.

It was less than a week before Anja was to fly back to Music City, with her two suitcases and collection of New York City-themed shot glasses. She wanted to go someplace exclusive, someplace to meet older men with money, with big arms and broad shoulders. No more students and no more hand jobs.

We went to a place called The Brandy Library, downtown from us, two subway stops away. It was full of men in suits, full of older men drinking expensive drinks. We were so dressed for it.

First, we went to the salon, hung with everyone, had a blowout and they plumped up our lips. They gave us false lashes and long fashion-length nails, in beige of course. I love beige, and now Anja loves it too. She used to wear only black before she met me, black fingers and toes. She told me I was so girlie, so much girlier than her.

Then we went to get dressed at her apartment, we were finally alone, we could just dress, no distractions from the guys, no pleas for some time on the recliner. Anj was happy, but I was slightly disappointed. I didn't mind that type of audience.

Anja had on a strapless white dress, short with beige pantyhose, and three-inch sandals. I wore a white button-up blouse and a short salmon-colored skater skirt. I had on nude thigh highs and five-inch platform pumps, they were white with a flowered pattern on them, they matched the little clutch I was holding. I even had a wide watch band that matched too, the watch itself, of course, didn't work, it was my grandmother's, I found it in her basement, and someone wanted $160 to fix it. It was just decorative now. I still looked at it all the time, I imagined I was always late.

Anja showed me the joys of making an entrance, making one with breasts in the supermarket or the coffee shop was my favorite.

We made our entrance into The Brandy Library, I felt like everyone was watching us, we were young, we were showing off our legs, our hair was so long. Anja smiled at the patrons as we made our way to the even longer bar. She scanned the bottles in the back as a tall bartender came over.

"Card's ladies."

"Here you go," Anja showed hers, I swallowed hard.

The bartender looked at me, he glanced down at my breasts. "How old are you Miss?"

"Twenty-four, We just graduated NYU, I'm from Bay Ridge..."

Anja stopped me from rambling. "Can you make us two Old Fashioned's with George Dickel please?"

He smiled, he shook his head, he came back with the drinks, "These are from the two gentlemen." He turned his head, and so did we. They grinned, they were easily in their forties, tall, quite handsome, probably had money. We sat, raised our glasses to the men, and drank. I licked my lips and smiled at them after.

We slipped onto the stools, I crossed my legs. I played with my hair, I tried to look at the various men sitting at the bar, tried to avoid the gaze of the few women. I almost always passed in a straight club or bar. As long as I kept my voice in check, paid attention to it, I was always fine. When I went to Courage, they saw through my gravelly voice, my long hair, lashes, and nails right away. They always called me honey, or girl, they always told me I was stunning. They always touched my clothes, my hair, even my breasts. I loved them for that. But now I was surrounded by older New Yorkers, ones that didn't know what gender fluid meant, what Vietnamese places were in the neighborhood, even what subway stop we were near.

We looked around, it was crowded. It was a nice bar, a nice vibe, people were even talking to us. I finally felt like an adult, even maybe an adult 'woman.' I had my long beige nails trailing on my stockings, it looked and felt so good, I was distracted by it, I could have done this all day. Soon we were surrounded by the two men that bought us drinks. They were good-looking, they were being friendly, respectful, they were smelling even better. One of the men complimented my watch.

I got close, I flirtingly whispered to him, I used my sexiest voice. "It's so broken." I made a face and bit my lip.

He smiled as my hair went into his face. He took my arm. He removed the band from my wrist, as we watched, he took off the watch and put the band back on me. "I will be right back." And he left with my grandmother's antique watch. I watched his ass as he left through the glass doors.

We were on our second Old Fashioned, we were talking to the two women next to us. One was a beautiful black woman, older than us, she had the most incredible nails. I asked if I could hold her hand, and look at her nails closer, they were so ornate, so pointy, they were just a little longer than ours. I loved them immediately. I was thinking she probably had the greatest life, she was a young beautiful female in the City. I was instantly happy for her, for her life. I wanted to tell her that but she spoke to us, waking me out of my imagination.

"I'm having a roof party Friday night if you two lovelies want to come."

We did, Anja put the address on her phone, we bought the two ladies drinks.

"Us too?"

We turned around it was the same men from before. I tried to introduce them to Lana, the woman with the nails. "Lana, this is the man that stole my watch." I smiled, I moved the hair out of my eyes. "I don't even know his name." I think I was flirting again.

"Well, my name is Jenson and I am the man who fixed your watch." And he handed it to me, I held it to my ear. I smiled at him, he was looking at my lips and I kissed him, I couldn't believe it, I felt so forward, so girlie. I didn't even mean to, it was so spontaneous. "Thank you, that was so nice, you are SO wonderful."

He laughed. "Am I?"

We forgot about Lana, who seemed annoyed at the attentive bartender for some reason, and concentrated on the two men. Anja was talking to Philip his friend, I kept on tapping my long nails on Jenson's chest and playing with his buttons. I loved being close to a man, I wished I had the nerve to do this when I was younger when I was thinner and cuter. Once we started on water, we got ready to go and they invited us to dinner. We left and Jenson's arm was around me. We said goodbye to the bar, we kissed Lana, I even kissed the bartender.

"When I get an ID with my real name, I will come back and show you."

"Okay, but you can come back before that if you want. It's nice having a beautiful woman to make drinks for." I paused when he said that, it did something to my heart, my hands shook.