A Long List of Firsts

We had a long drive ahead with traffic and all so I asked Dawn why Ricky did this? Her answer kind of surprised me. Apparently Ricky really liked Earl until he found out Earl was cheating on his mother Jane. It went on for several months then Jane passed away from a heart attack. She was buried in Monterey where she met Earl many years earlier but Ricky found out some disturbing news. Earl used her casket to transport money to be laundered and that set Ricky off. In his mind that was beyond disrespectful. He decided he would use his position in the 'business' to screw Earl out of some of his ill gotten gains. Out of curiosity, I asked how they transported the money. She said it was wrapped in black plastic. There were three blocks in the car with Ricky. The blocks were roughly a foot or so square and about eight to ten inches thick.

"Are you sure it was money and not drugs?"

"Ya...Ricky cut open each block on one corner to see what was inside," she replied, "There was wrapped stacks of used bills."

"Were they all the same?"

"I don't know. I only got a close look at one of the blocks he opened and it had twenties in it. Can we not talk about this anymore?"

I could tell it was bothering her so I didn't ask any more questions about the caper. Dawn was very quiet after that. I was running through all that she'd told me as I drove. I found myself stealing glances at her nylon clad legs and that was making me very hard. I know I shouldn't have been checking her out but I couldn't help it. I made a subtle adjustment in my pants then tried to ignore her sexy legs.

I pulled into a gas station just south of Santa Barbara to fill up before turning inland. I needed to stretch my legs as did Dawn. I was just putting the pump nozzle back when she got out to go use the restroom.

"I'll park over there and wait for you," pointing at some empty spaces by a low wall separating the gas station from a strip mall. There was a small electronics store that was still open and I decided I needed to make a purchase.

Dawn was standing beside the Jeep with a concerned look on her face when she saw me coming. Her arms were wrapped around her torso and legs were clamped tightly together. She looked hot in that outfit but clearly she was chilled by the wind blowing off the ocean. Although it was early June, the breeze was cold.

"Where were you? I was worried," her voice high and full of anxiety.

"Relax, I just needed a few things," I replied calmly holding up a bag, "Maybe you should change before we go."

"I'll be fine," she huffed but looked relieved I hadn't abandoned her.

"Suit yourself."

We climbed into the Jeep and I pulled out one of the prepaid cell phones I bought and plugged it into my charger then tossed it in the center console. As I closed the lid, I glanced at Dawn's legs as clandestinely as possible.

"If I had changed, you wouldn't get to perve on my legs the rest of the way to your cabin," she said with a sly smile.

I must've changed a wide range of red at that because she giggled while running her hand up her thigh. I was so busted but I couldn't help it. She has great legs in those sexy nylons. Dawn sensed my discomfort because she gave me a nudge.

"Don't worry about it, I'm just teasing you," she giggled again and gave me a wink, "Besides, I like it when you perve on my legs." She looked at the bag I had in hand, "Did you forget your phone?"

"No...I'm just being careful." I didn't elaborate and she didn't question me further.

It took nearly an hour and a half to get to the cabin once we left the gas station. Negotiating a narrow rutted dirt road in the dark isn't done at freeway speeds. Dawn had a white knuckled grip on the door handle right up until we arrived. I think that's when she started breathing again too. I parked under the car port I'd built last summer for times when I visit and it's raining (or snowing) so I don't have to get wet while unpacking or packing the Jeep. It was chilly here too, now that we were at some altitude. I opened the cabin door for Dawn and set a match to the pre-built fire in the fireplace then started my generator so we didn't need to use candles for light.

I unloaded the two soft side ice chests containing meat and other perishables first and got the contents into the refrigerator. I brought in the rest of the food and my bag with all my clothing. By the time I was done, the 1100 square foot, one bedroom, one bath cabin was toasty warm and Dawn was curled up on the couch.

"If you want to take a shower, the water heater should be up to temp by now," I told her.

She gave me a groggy smile and said, "Thanks...I think I will."

"I'll turn down the covers in the bedroom for you so you can hop right in."

"Where are you gonna sleep?" she asked with a concerned look.

I pointed at the couch, "It folds out into a bed."

"I don't wanna kick you out of your own bed."

"It's no problem for..."

She stepped close and took my hands in hers, "Please...Stay with me. I'd feel better with you close."

How can I refuse a request like that? She picked up her duffle bag and went into the bathroom without waiting for me to answer. I went back out to the Jeep and retrieved the phone that was charging in the center console. I plugged the other phone I purchased into a wall socket then entered the bedroom to get into bed before Dawn got done with her shower. I guess at 51 and not being in the best of shape, I was a bit self conscious about my appearance around a twenty something hottie. I climbed in under the covers in my boxers and a t-shirt and waited for Dawn.

I was staring at the ceiling, pondering the situation she was in. It concerned me that she let herself get dragged into a spot like this over a guy who promised a lot. Figuring the next move was going to be tough. Another difficult situation was sharing a bed with her and not embarrassing myself or being creepy. Just the thought of her in bed with me had my dick standing tall.

"You look cozy," Dawn said, startling me.

She had on a long, pink night shirt with 'Hello Kitty' on it and fuzzy ankle socks. Her raven hair was still damp and hung down straight. Her makeup was gone but she was still beautiful in a 'girl-next-door' kind of way. My mind instantly wondered if she was wearing panties and I felt my cock throb. I quickly scooted to the far side of the bed before she got in. I tried not to look but I got a glimpse of red underwear then I tried not to stare. I had to take my mind off her body or I'd be a wreck the rest of the night. I rolled over and got the recently charged phone from the night stand and handed it to her along with the slip of paper I wrote the emergency number on. Fortunately I have cell service at the cabin.

"You might want to text your boyfriend about what's happening with you and his step dad." She looked apprehensive but quickly started typing away. "I wouldn't mention being in bed with a guy old enough to be your father though," I added, trying to alleviate the tension I was feeling. I could see a mischievous smile spread across her lips but she didn't answer.

It took a couple minutes for Ricky to reply but Dawn seemed excited and guarded at the same time. They texted back and forth for a while then she turned to me and showed me a picture he sent. I took the phone so I could enlarge the image to see it better. Ricky was a handsome young man with his shirt off, on a bed flashing a cocky roguish smile. He was lean and toned but not too bulky. I hated him even more. Then I saw something in the background that I'm sure Dawn hadn't noticed or she would have said something, I have no doubt. It looked like a foot, a woman's foot. How could I tell? The subdued blue nail polish on the toes. When I shrank the picture back down to normal size, the foot blended into the comforter he was lying on. Ricky was in bed with a woman or he was a gifted contortionist with a thing for painting his toenails. I handed the phone back to Dawn then I heard the phone chime again. She read the message and turned to me.

"He wants to know where I am," she stated.

"Just tell him you're safe and with a friend you can trust," I replied.

She held my gaze for a moment as if judging the validity of my answer then typed away. The next time he sent a message she frowned, "He wants to know if I can come to him."

"Where's he at?"

She bit her lip then timidly answered, "Taholah, Washington." I guess the surprised look on my face wasn't what she was hoping for. "He'll pay for everything if you bring me up there...And pay you for your time too. I know he will." She seemed sure but I wasn't, given the circumstances.

"I don't know where in Washington Tallhow is but Washington is at least a two day drive from here."

"It's Taholah," she corrected.

"What ever...It's a long way there and back again," I replied, "I'm on vacation..."

"So take a road trip with me to Washington," she leaned in close, "He'll make it worth your while, I promise."

I'm such an easy mark for a pretty face. I nodded without even thinking about it. Sucker! I bet I just get a hand shake and a 'thanks dude' from that little prick; or worse, a bullet to the head since I know his secret. He's not actually dead.

"What's the address of where he's staying?"

Dawn excitedly typed my question. When the phone chimed again she had a puzzled look on her face, "He says to text him once we get to Aberdeen then he'll give us directions where to meet."

'I'm not liking this,' I said to myself. I agreed but I was going to do some planning before we walked into something unexpected. Dawn responded then put the phone on the nightstand. I guess they were done chatting. She kissed me on the cheek, turned out the light then snuggled down into the covers with her back to me. Thoughts of sexual exploration with this young lady was the last thing on my mind as I stared at the ceiling once more. There was something that just wasn't right about this whole thing. I didn't think Dawn posed a threat but I didn't know much about her. For all I knew she was setting me up. My mind worked on all sorts of scenarios and most weren't healthy for me or Dawn.

I must have finally fallen asleep because faint sunlight peeked through the window and shown on my face, waking me. I then noticed a warm body spooned against mine. I'd forgotten about Dawn being in my bed. Her arm was over my hip and I could feel her soft breasts pressed into my back. It was a wonderful feeling having a beautiful woman in bed with me again, at least one that wanted to be in bed with me, unlike my ex-wife. I was getting hard then she shifted her hips and I felt something out of place. Something warm and stiff, lodged in the cleft of my ass cheeks. I knew what I was feeling but my mind wasn't accepting the conclusion. I was frozen while trying to wake from the dream I must be having.

She made a soft moan and her hand pulled at my hip as hers began to rock ever so slightly. My mind was screaming 'GET OUTTA THERE!' but my body wouldn't move. It couldn't be true. Dawn couldn't have a cock; it wasn't possible. It dug deeper into my ass crack with only my boxers (and her thin panties) as a barrier; I bolted out of bed, waking her in the process. She wasn't fully conscious when I threw back the covers. What I saw just wasn't possible. 'She was a beautiful woman not a man dressed as a woman,' I kept telling myself. Her long nightshirt had ridden up above her waist displaying a prominent bulge in those sexy red panties I saw last night.

"What the fuck!" I stammered in disbelief.

Dawn was now awake and realized she was on display. Although not naked, there was no mistaking what was hidden in her underwear; a fully erect cock that must have been about five inches long. She yanked the sheets back down and hid her face with her hands. Once she'd covered herself from the waist down it was as if she was once again a woman and not a man in woman's clothing. I could see her nipples were hard in the cool morning air and my mind tried to erase the thing I saw between her legs. There was a long awkward silence between us when I heard Dawn begin to cry.

"I'm so sorry," she sobbed, "I didn't want you too...I mean...I was afraid to tell you..." she broke down tears.

I'd read about transgendered people, I'd seen pictures of them; mostly of men that were trying very hard not to be men and failing. But Dawn is beautiful. There was no way she'd be mistaken for a guy. She's petite and curvy and has a very soft feminine voice...I was in conflict. I didn't know what to do, what to say. I'd never had any kind of attraction to guys; I was a man's man. I wasn't gay. I didn't want to have sex with a man or a man in drag but Dawn was a dilemma for me. Even now, knowing what I did, my cock was hard as a rock. Until that very moment I saw that she had a penis, I'd have fucked her the minute she asked. It made me mad that she had a penis but what could I do about it?

"Why didn't you tell me you had a..." I couldn't say it.

"A cock! A penis...a pecker...Why? Because of how you're reacting right now," she fired back.

"But you could've told me."

"Would it have kept you from staring at my legs? Are you embarrassed you have a hard-on right now? I bet you've jerked off a hundred times thinking about fucking me...about me sucking your cock," she glared at me with a frightening fierceness as tears streamed down her cheeks, "I'm a WOMAN! I may not have a vagina but I'm every bit a woman! If you hadn't found out about my...You'd still be having those sexual thoughts. Don't worry; it doesn't make you gay to be attracted to a transgender woman."

I felt like a total idiot. She was right. What difference would it have made? Had I not found out about her plumbing, I'd still be fantasizing about her. My reaction to finding out she wasn't born a woman is based on social stigmatisms and prejudice. As far as my mind and body were concerned, she is a woman. I had fantasized about fucking her while jerking off, probably more than a hundred times. I didn't want to admit it but I was embarrassed about being turned on by her. Standing there, watching her cry tore me up. I wanted to hold her and comfort her, tell her everything would be alright.

"I'm sorry," I said in a repentant voice. I didn't expect her to believe me or even accept my apology but I had to let her know how I felt.

I'm sure I surprised her with that. I could tell she's had some negative reactions before from other people but probably few that regretted it after the fact and were willing to say they were sorry. Tears continued to flow and I felt terrible. I wasn't sure what I could say or do to make her feel better so I tried the only thing I knew when in an uncomfortable situation.

"Are you still going to like it if I perve on your legs?"

I think Dawn was stunned by the audacity of my question after what had just happened. It took a moment then she began to laugh. When she got control of herself, she looked at me with an appreciative smile and said, "I'll still like having you perve on my legs." We both laughed. I think that broke the tension.

"I'll go make us some breakfast," I finally said and started getting dressed. Dawn just smiled. She looked relieved.

I rekindled the fire then whipped up some bacon and eggs and waited for Dawn to join me at the table. She came out of the room in a loose fitting t-shirt, tight fitting yoga pants and those same fuzzy socks she wore to bed. The shirt was long enough to hide any bulge that might be present. Walking meekly to the table and sitting down, she inhaled deeply, taking in the wonderful aromas. Dawn looked at me then down at her plate.

"I'm sorry I yelled at you," she said quietly.

"You had every right to yell at me...I was an asshole."

She took a long look at me then picked up her fork and sampled the eggs, "Mmmmm...These are good!"

"Thank you," I replied, digging into my meal.

"Are you still okay with taking me to meet Ricky?" Dawn asked apprehensively.

"Yes...I'll take you but let's not have anymore surprises, okay?" She blushed, not wanting to look at me then nodded.

There wasn't too much to prep for this trip. I was going to throw some clothes back in my bag, grab my laptop and toss in those extra phones I picked up. We'd stay in a motel or two depending how good we did on the road. When we got there...That's where the easy part ended. I wasn't sure how this was going to unfold. Part of me wanted to tell Dawn about my apprehension but the other part still wasn't sure about her part in all of this. I didn't want to tip my hand too soon.

We finished breakfast; got things cleaned up and put our bags in the Jeep. Dawn put on some low heeled boots for the trip and we were off. Once we were on pavement, Dawn eased her seat back and kicked off her boots. I glanced at her legs out of habit and she smiled when she saw me do it.

"I guess I should have put my hose back on for the trip," she teased. I focused my attention on the road, trying not to show my embarrassment at being caught.

I drove hard all the rest of that day and into the night before calling it quits in Yreka, California. Dawn and I discussed many things during our ride; her job at Athena's, her desires for a career in management and her relationship with Ricky. The latter got very involved. The more she told me about him, the more I didn't trust him. I also picked up some inconsistencies in the story Dawn told me about this heist. We found a motel and rested for the night. The room we got had two twin beds. Part of me was relieved that I wouldn't wake up with a cock prodding me in the ass but not sharing a bed with a beautiful woman was a disappointment.

We woke up late the next morning and while Dawn was showering, I used my laptop to find a motel outside Aberdeen so I could have some time before we met Dick (that's how I was now referring to Ricky) to get a lay of the land. I had a good mapping program that would let me see every trail and road in the area.

We took our time eating breakfast in Yreka then drove just beyond Vancouver, Washington before stopping again for a late lunch. I made sure to take my time eating because I didn't want to get to Aberdeen until the following day. I could tell Dawn was anxious but I wasn't going to let Dick set us up if I could help it. We were a little over two hours from Aberdeen at that point. It wasn't terribly late so I was going to have to come up with some excuse to stop. Dawn had told me in our many conversations that she couldn't drive a stick shift so if I couldn't continue, she couldn't offer to take over. I wanted to spend the night in Olympia then contact Dick and find out where he wanted to meet so it could be done in the day light. Hopefully I could figure out a possible escape route (or two) if things went bad like I was expecting. I truly hoped I was wrong about Dick but my gut was telling me 'Beware'. The worst part was I could tell Dawn really loved him and I hadn't told her about what I saw in that picture or the feelings I was having toward her 'boyfriend'.

While filling up just outside Olympia, I was talking to a local lady about places to stay in and around Olympia. She mentioned a couple motels then told me about a vintage hotel in a town just west of Olympia called the Old McCleary Hotel. It sounded interesting so I looked it up. It was in the town of McCleary about forty-five minutes from Aberdeen. It would be perfect. I had already been setting the stage for calling it a day in Olympia do to 'My back giving me trouble.' So when I finally said I couldn't continue just outside of Olympia Dawn was frustrated being so close yet so far from the goal. I managed to get us a room (one king size bed) for the night. She wanted to contact Dick but I was reluctant, not knowing what he had in mind yet. Dawn was getting very upset as we were preparing to settle in for the night.