Rest Stop Romance Ch. 02

~The following is entirely fictional and just a fantasy of mine. Any likeness to actual persons or events is unintentional and coincidental. Due to the Pilot receiving a high rating and getting so many views in just a few days, here's chapter 2!~

I woke up early this morning. I wanted to make a nice breakfast for the devilishly handsome trucker that was still fast asleep in my mom's old bedroom. Last night I had been subjected to the most pleasurable experience of my life as Dave had been the man to take my virginity. I had been living life as Tommy for the past 20 years, but after last night, my "alter-ego", Rose, had truly been brought to life. In fact, I woke up and decided to surprise Dave even more by wearing nothing but a new pink pair of panties and matching bra, covered up only by Dave's shirt which fell over me like a small dress. I straightened up my long, brown wig and kept it firmly attached to my head with fresh make-up on my face. I even decided since I was staying barefoot to paint my toenails with my cutest purple nail polish. I even decided to put matching coats on my girly little fingernails.

To an outside observer, I was your typical 20 year old woman, waiting for her boyfriend to wake up. Dave would be the only one to know I had a little extra downstairs. Thankfully, it didn't bother him in the slightest. In fact, it had only made him want to fuck me even more. Speaking of which, even though I was still wobbly on my feet from the near two hours of fucking I had received last night, I was eager to get right back to it today. Rose's mind was far stronger now than Tommy's had ever been. She knew what she wanted, how she wanted it, and when she was going to get it. Just as I was finishing making breakfast, I heard Dave coming downstairs.

I was still mesmerized by the hotness of this man. His sculpted, tan chest was in full view since I had hijacked his shirt. All he was wearing was the pants he had slept in the previous night, holding me the whole time. He looked me over from head to toe and the first thing out of his mouth were three words I had always wanted to hear a man say to me, especially after last night.

"Good morning, beautiful." He started smiling, "I guess the mystery of my missing shirt is now solved."

"Hehe. It's comfy," I answered back to him. "Do you want some coffee or orange juice or maybe milk with your breakfast?"

"Coffee is fine, dearest." Awww. He called me dearest! We sat and ate the bacon, eggs, and mini-pancakes I had prepared for us and talked for what had to be almost two hours. I learned that Dave was 27, had a steady home-life and was looking to settle down after finding a new job with less travelling. Lucky me, I thought. I couldn't do without this man, or at least without the activities we performed last night, for very long. Activities that I was still wanting to get back to. We talked for ages as I explained to him how my mom had passed away and left everything to me. I could tell he felt bad for me, being here all alone, except for the stints my girlfriend, Tiffany, stayed here with me. She, who was on vacation with her parents for another thirteen days, had no clue about me being transgender whatsoever. I was still deciding how to handle telling her what had become of me while she was gone, and how to tell her I didn't want to hurt her but I just couldn't date her anymore.

AS if reading my thoughts, Dave asked me to unbutton his shirt so he could see my sexy little underwear. He obviously liked what he saw. I decided it was time. Totally ignoring the dishes on the table, I grabbed Dave's hand and led him upstairs to my mom's bedroom. I dropped his shirt to the floor and pushed him down on the bed as he undid his pants and slid his boxers down to join the rest of his clothes. I grabbed a condom and some AstroGlide from the bedside drawer. I stroked his hardening cock as I pulled the condom down over it. I squirted a little of the lubricant onto the head and rubbed it all over his smooth, poly-urethane covered shaft. When it was nice and slick, I pulled my panties to the side, straddled my trucker and eased my ass onto his massive tool. He was as eager as I was to get going and grabbed my hips, helping me down to his groin. It was then I got to repeat my performance from the night before and began to bounce up and down on his cock. My long, brown wig still attached firmly to my head was bouncing along with my breast forms in rhythm to Dave's thrusts and my ass slapping onto his groin. I continued to cowgirl him for almost 35 minute before he rolled me over onto my back. However, instead of fucking me silly in this position like he had before, he took it slow and then pulled all the way out.

By this point, my panties were getting annoying so I slid them off and threw them off to the side. Dave then picked me up and put me back down on the bed on all fours, my ass pointing right up to him.

"Oh, Dave. Please fuck me doggy-style. I want it nice and deep. Please fuck my ass some more." He happily obliged and got behind me. He re-penetrated my asshole slowly but steadily. He then picked up the pace once more, slapping his groin into my ass cheeks. He pounded away at my ass, going faster and harder with each stroke. At this point, pain was all but gone. This was full-on pleasure. I pushed with him in rhythm, getting full enjoyment out of every second. After 20 minutes, Dave had pulled out again so I could lay down on my back. It was time for the thorough fucking I was waiting for. I instantly spread my legs, and lifted them into the air, exposing my stretched hole to him. He quickly filled it back up. My long,brown wig splayed all over the bed behind me and my breast forms were bouncing from the force of his stroking. He went from stroking back to pumping me. I wrapped my legs around him, the painted toes of my bare feet touching together. I threw my arms around the back of his neck and pulled him into kiss me. His tongue once again began exploring my mouth while his cock was still pushing its way through my rectum. Whenever my mouth wasn't full of his tongue, I was moaning and screaming like the little woman I was, feeling more and more pleasure with each thrust.

After what was almost an hour, he told me he was ready to cum. I decided I wanted him to pull out. He did as I asked. I ripped the condom from his cock, and kissed the head of it as I had the night before. I took all of it into my mouth, bobbing my brown hair covered head up and down the length of his shaft, massaging it with my tongue. After ten minutes of my tongue working and my mouth being filled with his member, it expanded and he came full force into the back of my throat. Jet after jet hit the back of my throat but instead of gagging, I swallowed it all down. The taste was far better than anything I had expected.

After deep-throating him and swallowing what felt like a gallon of Dave's cum, he stood up and went to grab his clothes.

"Hey Rose, we should go get your car from the rest stop. Besides, I want to talk to you about something on the way there."

"Okay Dave. Let me get dressed." I found my panties and pulled them back up over my legs. I ended up getting a pair of blue skinny jeans out of my mom's closet, and a plain pink t-shirt. I fixed my wig and grabbed a pair of black flats. I got a black bracelet from my mom's jewelry box and off-set the look with black earrings and a black necklace. I went downstairs and out the door, where Dave lifted me up into his truck.

"So like I told you before, I leave later tonight. But I got to thinking last night. You said your girlfriend was going to be gone for thirteen days yet, right?"

"Yep. It'll be a while before she gets back."

"Well then, how would you like to leave with me tonight? We'll be going cross-country for deliveries but I can get you home in about 10-12 days. You can stay all girlie'd up the whole time, and be my official girlfriend as far as anyone else is concerned." I almost didn't know what to say. I wanted Dave so badly I could feel it deep inside, no pun intended. But was I ready to stay Rose for such a long amount of time. I quickly had my answer.

"Yes!! I would love to go with you, Dave. Let me pack when we get back to my house."

***

I was back at home, getting ready to leave for my cross-country excursion with my new trucker boyfriend. I never would of thought even two days ago that I would be spending almost two whole weeks as a woman. It made me happier than I had ever felt. I called work and told them my grandmother was sick, and used my two weeks of personal time to cover the pay. Before I left, I went up to my mom's room, unlocked the door and sat on the bed all dressed up, this time back in my white blouse and denim skirt. I opened my laptop and turned on the webcam. I told the camera how I was all dressed up, extremely happy, and about to go on a cross-country adventure with my new boyfriend. I also recounted how he had fucked me raw the past two days and how much I enjoyed every second. When I finished, I smiled and waved at the camera, stopping the recording. I saved the file as, "Rose Pre Trip". I closed my laptop, and set it under the bed in it's usual hiding spot. I walked out, locked the door, and headed downstairs.

***

After driving for a few hours, Dave and I had stopped three states over at a rest stop. He pulled me over onto his lap. I had my panties off two states ago so he sat me down on his already exposed cock and let me do what I did best. This was only the beginning of the ten best days of my life.