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Rest Stop Romance Ch. 02

By: Dark_Rose90



~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.

Rest Stop Romance Ch. 03



~The following is entirely fictional and just a fantasy of mine. Any likeness to actual persons or events is unintentional and coincidental. Sorry for the disappearance, writer's block, but since Ch. 02 is still my highest rated story and was my first to get that little red H, here's Ch. 03! The saga continues!~

*****

Dave and I had been on the road for five days now. Thankfully, the sleeper in his cab was comfortable enough that we spent almost every minute we could on it. After the first couple of times, we were both sore and I could barely walk. But now, we could go at it like bunnies and be fine, as I had gotten used to it. I spent the last five days sucking Dave's cock and getting fucked in just about every position we could possibly get into. My only problem was, with nothing new, I was starting to get bored. 

Dave could sense this, or maybe he was getting bored too, but whatever it was, he came up with an idea. He said we would be stopping at a rest stop tomorrow evening. He had to meet up with one of his friends. For the first night in over seven days, we didn't have sex. Instead, we just cuddled and went to sleep and I was still just as happy as when we were fucking.

Day six of the trip started like any other. I woke up and fixed one of my wigs on my head. I chose a breast-length black one today. I applied my make-up the best that I could. When I was finished, I slipped into my outfit for today. I had never worn this one before. All of my clothes up until this point had been my mother's, but this was actually Tiffany's. I remember buying this for her once so she had something to wear over at my house. However, after wearing it once, she never did again, and it just sat at my house, calling my name. It was a black dress that buttoned up in the front, adorned with white polka-dots. It also had a white belt around the waist, which made it hug my figure closely. I accessorized with a white bow in my hair, a white plastic bracelet on my wrist, and finished the look with a pair of black and white pumps with bows on the straps.

Wearing this outfit, and with the black wig on, I actually kind of resembled Tiffany, in a way. I couldn't help but wonder what she'd think when she found out what had become of me while she was gone. I knew, in this moment, that I could never go back to the life I lived before meeting Dave. Unfortunately, that meant Tiffany and I couldn't stay together. I didn't want to hurt her, but maybe she would understand. I hoped we could still be girl-friends. I didn't have any of those yet.

I slid out of the cab of the truck, and walked over to meet Dave, heels clacking on the pavement. We were outside of a rest stop, not unlike the one where I had my first fucking and lost not only my anal virginity, but just my general virginity, to Dave. I still remember the mix of emotions running through my mind when Dave first walked up to me, me kissing the head of his cock for the first time, or him lifting me onto his lap, and then sitting on his cock for the first time. It was on a picnic bench, just like the one I saw out of the corner of my eye as I walked towards the rest stop, where Dave was talking to his friend, Travis, another trucker whom I was to be introduced to.

"Wow. You weren't kidding when you said she was a hot little piece, Dave." Travis spoke, he was about Dave's height, black, and as I was about to find out, just as huge downstairs. I could already tell that he was not as gentlemanly as Dave had been, but that didn't matter. What I assumed was about to become a threesome with 'little old me' sandwiched in between two hot, toned truckers may have been just the spice Dave and I needed to re-invigorate our cross-country sex trip. 

"Easy, buddy. She is my girlfriend after all." Yay! He called me his girlfriend! He had said it before, but hearing him tell another man that I was his, made me very happy.

"Yeah, yeah. So we doin' this, or what? I haven't blown a load in over a week. I'm pent up, man."

"As long as Rose is sure she is okay with this. Babe?" Babe... Yay! I think I'm in love with this man.

"Yes. I'm ready. Where are we doing this?" I muttered in my femme voice. Looking so chic, femme, and submissive was eating these guys alive. I couldn't wait for what came next.

Dave and Travis led me over to the latter's truck. The sleeper was different than Dave's. It was bigger. I assumed that was why we chose his truck. Travis had his pants off almost immediately.

Due to the lack of underwear, I could see his cock clearly. It was already hard, standing about 8 inches long, but it had to be almost 4.5 inches thick. Dave told Travis his only ground rule was that Travis got head only, and he surprised me a little by saying my ass, and pussy, were his alone. Did Travis not know about my secret? He agreed to the terms however, and positioned himself sitting on the mattress his cock pointed up, waiting for my mouth. 

I got on all fours, and climbed across the mattress bringing my head straight in front of Travis' member. I lowered my head towards, it kissing the head as I normally did to Dave's. This seemed to set him off, as he quickly grabbed my head and pulled my nose to his groin. As I was deep-throating him, I felt the familiar, and welcome, sensation of Dave's cock poking my vulnerable ass. This may have been the exact spark we needed to spice things back up, because my ass literally lunged to meet the knocker at the back door. As my head came away from Travis' crotch, I felt Dave's cock push farther into me. It wasn't long until the two found a perfect rhythm and I was in heaven. As one cock moved out of me, the other moved in. This kept up, getting faster and faster until my head was bobbing so fast I could almost feel the friction on my lips and in my throat, as well as Dave's groin slapping against my ass at a pace unlike any other. The rhythmic throat and ass fucking continued for nearly thirty minutes, until I felt a familiar spasm in my mouth. Instead of letting himself cum in my mouth, Travis quickly pulled his cock out of my mouth, leaving me disappointed at least until I felt a new sensation. The warm, sticky jets I usually felt come from Dave's cock into my waiting ass, and once mouth, splayed all over my face.

I looked at Travis' cock as it continued to spray semen all over my face. When it finally stopped, I wished it hadn't for some reason. I'm sure this was humiliating to most girls, but I liked it for some unknown reason. Travis quickly threw me a towel from behind the bed. I put my face down into it as Dave gave his final thrust into my ass, causing me to moan louder than I ever have before as his own streams began filling the inside of my ass. His condom must've broken. He actually wore one this time, for appearances' sake. From the excitement of having Travis splatter his cum all over my face and Dave's cock spurting more of it into my ass, I came right into the skirt of my dress.

After Dave pulled himself out of my ass, I wiped my face clean with the towel. When I looked up, Dave and Travis were talking.

"Sorry for painting your girlfriend white, man. It was just reflex to pull out. Besides, it looked like she enjoyed it." Travis said.

"Whatever, man. If she's okay with it, then whatever."

"Look how wet we made her. There's gonna be a stain on that pretty little dress of yours, girl." 

"Well," I said in the sexiest tone I could muster, "it's a good thing I borrowed this from a friend, then."

"Any friend of yours is one I'd like to meet. Now you be a good girl and go back over to Davey-boy's truck. I gotta have a word with him."

I spent what felt like an hour in Dave's truck, waiting for him to come back. I could only imagine what they could've been talking about. I changed out of my dress, and slipped into another one I had bought on the road. Oddly enough, it was almost the same one I had gotten for Tiffany. In fact, I hadn't realized I bought the exact same dress, only it was white with black polka-dots and a black belt. I kept the white bow in my wig, and the same shoes on. I also took off the white bracelet, and replaced it with the same black one I had worn the day we went to pick up my car.

What seemed like another hour passed, and I saw Travis' truck pull out of the rest stop and head back to the highway... The same highway I drove down the night that I met Dave. I then noticed why that picnic table looked like the one Dave fucked me on. It was that exact table. We were back at the rest stop just barely an hour from my hometown. I sat and thought about why he would bring be back here, and it slowly sank in that he wasn't coming back to this truck. I thought I had seen another person in Travis' cab, but I wasn't sure. Until now. I had been ditched. It made no sense to me. I was so hurt and confused by what had happened, and how suddenly it had happened. I had no idea what to do. I started packing all my clothes I had brought/bought on the road, my wigs, and everything else into a duffle bag I found in the back. Not even thinking about how I was dressed, or the new way I talked, tears welled up in my eyes as I called my next door neighbor, Tom. 

"Tom?: I barely managed to get out through the tears, "It's Ro- Tommy from next door. I'm stuck at a rest stop outside of town. Could you come pick me up?"

-Tom's Perspective-

Six Days ago:

I woke up this morning and looked out the window to a new sight. There was a tractor trailer parked in the driveway of my neighbor, Tommy's, house. We weren't particularly close, but we had a small friendship blooming due to having the same name. Sheer coincidence that he went by Tommy and I by Tom. We could have our own sitcom, I'd often chuckle to myself. 

Anyway, back to the window. I was looking at the tractor trailer again. It was strange that Tommy's car wasn't there. I remember him driving out last night, but I don't remember him coming home. I looked again as a tall, tan-skinned man walked out to the truck. I assumed he was the driver. Following right behind him was a beautiful girl I had never seen before. She had long, brown hair and was wearing a pink t-shirt with blue skinny jeans. I couldn't help but notice every detail. From the top of her head, to the bottom of her black flats. She couldn't have stood fore than 5'5 or 5'6. Though I had never seen this girl before, I only knew one thing about her. She was gorgeous. As the driver lifted her into the truck, I couldn't help but feel a bit envious of him. I pictured myself holding that pretty brunette by the waist as he was, but I was pulling her closer to me. Although, my lust was soon replaced by worry. I hadn't seen Tommy's car come back in the driveway. I got nervous, so I called Tiffany. I had gotten her number when she came over to my house drunk one night. She was complaining about the fact that Tommy would never make a move and wouldn't try to have sex with her. She tried to get me to do her, but I wouldn't. Like I said, Tommy and I weren't all that close, but I couldn't do that to him.

"Hello?" The female voice came through.

"Hi. Tiffany? It's Tom, Tommy's next door neighbor. Have you heard from him since last night? I saw his car leave, and it's still not there. Did he go to a friend's place? Or is he with you?"

"No. I'll try to get a hold of him though and give you a ring back. I'm on vacation with my parents."

"Oh okay. Sorry to bother you. It's probably nothing. It's just unusual to see him gone all night. Thanks." I still couldn't shake this bad feeling I had in the pit of my stomach. I didn't know if something bad had happened to him, but I still felt uneasy. I should've mentioned the girl and the trucker to her, but something told me not to. I didn't want to upset her more than I had to, I guess.

Present Day:

Things were getting stranger. I went to work after I called Tiffany six days ago and when I came home Tommy's car was there. I thought about going to say hi and check on him. Maybe even ask him about the brunette girl I saw. Maybe they were friends and he could introduce me. I decided against it though, as all the lights were off. It was pretty late. But I haven't seen the lights come on for six days now. The car hadn't moved for six days. I was really worried now, so I called Tiffany again. I told her about the car, and the lights in the house. I told her I still hadn't heard from Tommy in the six days either. She got really worried too and told me she was going to fly back early. It would take her a few hours to get to the airport, get a ticket and get back home. Five, maybe six perhaps. I told her I would go knock on the door and call her back. If he was fine, she should stay and enjoy her vacation. 

I walked outside and went next door. Just as I walked up to the door and was about to knock, my phone rang. It was Tommy. I picked it up:

"Tom? It's Ro- Tommy from next door. I- I'm stuck at a rest stop outside of town. Could you come pick me up?"

*To be continued*