After watching Greg pull back onto the highway, I took the next fifteen minutes to reapply my makeup in the rearview mirror and gather my thoughts. I realized that the sun had gone down and the rest stop parking lot was not quite as inviting as it was when I pulled in. Two overhead street lights dimly lit the parking lot and the short sidewalk to the building in front of me. I decided that staying in the parking lot too long could certainly look suspicious and perhaps wasn't quite as safe.

I merged on the highway with no real plan. I spent the next two hours driving up and back on a stretch of highway that was populated by a fair number of truck stops. I figured it would take a bit of luck to connect with Tim, but I figured I had nothing else better to do, so I drove. I was about an hour south of my hotel and decided that I would drive another fifteen minutes before turning back and calling it a night. It was five minutes after that that my phone lit up with an "Unknown Caller" calling from Pennsylvania.

"Hello?" I answered in a much more feminine voice than was probably needed.

"I take it this is Jenni. It's Tim. Greg's buddy."

"I was beginning to think this just might be a lost cause. I am so happy to hear your voice. I'll be even happier if you're close enough that we might be able to meet tonight."

I calmly carried on a brief conversation with Tim. As it turned out, he was a little more than an hour from where I was at. He had pulled off for the night at a truck stop to get some sleep. I lied and told him I could probably be there in thirty to forty minutes, and he agreed that he'd wait up for me. The closer I got to my destination the more I could feel my heart beating in my chest. I took a deep breath to relax as I pulled off the highway. I quickly realized that this was an enormous truck stop with at least fifty trucks, likely more, lined up and parked for the evening. Between the gas station and the sea of trucks were a very well-sized restaurant and convenience store. The gas station itself was very well-lit and very busy. There would be nothing discrete about my walk to Tim's truck. As was agreed, I called Tim when I arrived.

"Are you here?" he asked.

"I just parked and am ready to meet you. Where is your truck at? Is it going to be a long walk?"

"Long enough that I'll be able to watch you as you approach. As we discussed, if you're my type, I will climb down to greet you."

"If you don't, I turn around and walk back.”

While perhaps a bit harsh, I told Tim I’d rather avoid the awkwardness that would exist if he wasn’t interested. I had my out as well. No strings attached, I could turn around and walk away the same. Tim told me he was in the fourth row of trucks and right on the end. His truck was red with noticeable white trim. As I started my walk back, I could see it right away. As I got closer, I saw Tim. By the way his face lit up, I was guessing I had passed his eye test. A second after we made eye contact, his door opened, and Tim climbed out to meet me.

Saying that Tim was fucking hot, would probably be an understatement. It was evident that he kept himself in very good shape. His well-groomed beard gave him a rough yet sexy exterior. There was no way I was turning around.

“Holy shit! Greg’s description didn’t do you justice. Fucking hot, babe! I can't believe you're really a dude. Damn.”

“Why thank you! Now that is a greeting that no girl would ever walk away from.”

We politely embraced as I met him. His arms were very strong, very masculine, and he knew exactly how much pressure to apply to make me feel safe and wanted all in one hug. As we separated, his hand slid to the small of my back and guided me to his truck. We were in his sleeper within minutes.

Tim’s truck was a little more spacious than Greg’s. Once we were seated, there was an unusual amount of small talk that included Tim asking a bunch of questions about my history dressing like a girl. He was especially interested in how I started dressing and was particularly fascinated with my story. We were sitting a body length apart until I decided it was time to move closer and see how interested he really was. Our eyes locked and the truck got really quiet. I leaned forward and kissed him softly on his lips. I left them there allowing him to reciprocate. His lips push back against mine. Seconds later, I felt his tongue press against my lips. I offered mine in return. After about five minutes of playful kissing, I pulled off so I could I slide my jacket off, tossing it across the sleeper onto a table. I went to re-engage and noticed his eyes wandering to my boobs.

"You can touch. There is a little boob and a little boost. They are quite cute."

"Yes, they are. And they are real?" he asked like an innocent virgin.

"Listen, I’m not going to lie. My bra is certainly helping things. But they are very real. And I love when they are sucked. We'll get there but until we do, feel free to touch all you'd like."

Tim and I started making out again. His hands freely explored my body and pulled me against his body from time to time. I could feel he had a very muscular back and shoulders. His arms were very well defined. Not only was he a man who took care of his body, I could tell knew how to take care of a lady. It didn't take long for him to maneuver his hand under my dress and right on my ass. His fingers rubbed my ass cheeks over my black panties and then slowly under them. It wasn’t long before he was sliding them down my legs.

Tim was a great kisser. He was soft and passionate but also aggressive and manly. It was clear he didn’t need direction. With my panties off, Tim started rubbing my legs over the fashionable thigh hi stocking. From my legs, his hands slid up my waist, hips, and torso until reaching my breasts. Tim stops kissing me for a moment as both his hands cupped my boobs over my dress slowly rubbing each, looking me in the eye. I bit down softly on my lip in pleasure.

“As beautiful as you look, I think we need to get this dress off,” he said softly. I didn’t object.

He reached for the zipper and slowly moved it down my back. I could feel the dress loosen as he moved the zipper down my back and then slowly helped it fall off my shoulders to the floor. I turned and faced Tim standing in front of him wearing a pair of black ankle-high booties, black thigh highs, and a black and pink lace bra. My cock was fully erect, but it didn’t seem to bother him at all. As his eyes admired my body from head to toe, he kicked off his shoes and started to undo his belt. I reached forward to help him, casually brushing against the noticeable bulge that had formed between his legs. I slid his pants down to his ankles making sure I brought his briefs down as well.

As I bent down to help him step out of his pants, his cock was right in front of my face. He took it and rubbed it across my cheek and then gently slapped it against my face. I intentionally ignored this at first but once his pants were off, I turned my attention to what I really wanted. I moved his hand away and took his cock softly in one hand and his balls in the other. I moved my mouth toward his eight-inch rock-hard cock, licking down the shaft until I reached his balls. I took the first and then the second in my mouth. I let the moment develop before starting to run my tongue all over his nuts. He moaned as I pushed him down into the seat.

Kneeling in front of Tim, I spent the next ten minutes ravaging his dick with my mouth, lips and tongue. There was more than one moment where I thought he was ready to cum and pulled off to kiss him around waist and inner thighs. I heard him reaching for and opening a condom. As he rolled it down his cock, I sat back, spit on my hand and started to finger my tight hole. It had been forever since I had a cock in my ass and I was bound and determined to break that dry spell. I found my hole to be plenty wet and was quickly able to insert two fingers in to pleasure myself. I stood up and leaned over the table offering up my ass for him to take.

"Oh my god your little twat looks so tight," Tim said as he stood and moved toward me.

He slapped my ass twice before sliding his middle finger between my cheeks and inserting it into my hole.

"I bet that feels good, doesn't it? God damn, you're so wet already. Fuck, I'm going to put my dick inside you now. I don't want to hear a peep out of you. Do you understand?"

I nodded in approval. As Tim withdrew his finger, I quickly felt the head of his cock press against me. He slowly inserted it inside me. While I appreciated him taking the time to ease his massive head into my hole, he didn't spare the same courtesy when filling me up. His huge cock push deep inside of me leaving me in a great deal of pain. The heavily lubricated condom helped, but it had been a long time since I was filled up like that. I leaned against the table, my eyes tearing up from the pain, in total silence.

"Good girl. I know you want to say something. Pout or whatever. Stay quiet," he said as he thrust himself in a little further inside me. "I bet that hurts, don't it? Good girl," he said as he stroked my hair.

"I'm going to fuck you with this thing on my dick until you feel like you're nice and wet. At that point, I may just take it off and shoot my load inside you. What do you think about that?" he asked.

Tears were flowing down my face, and I could feel my mascara dribbling down my cheeks. I wasn't sure if I should answer or just nod. I sat there in silence. Part of me was in pain. Part of me was loving the pleasure of being fucked by a complete stranger. The reality of the situation was completely scrambled in my brain.

"Go ahead, you can answer," Tim said as his dick started sliding in and out of me.

"I just want to satisfy my man however I can."

"Mmmm. What a good girl slut you are. Greg was right. You are a fine piece of ass and VERY obedient one as well."

Tim's hands firmly grasped my hips as he started sliding his cock in and out of my asshole. I could feel his cock swelling inside me as he did. Occasionally, he would pause to reposition himself, always leaving himself inside of me when he did. I think it was his way of holding off shooting his load a little longer. I quietly moaned and got approval from Tim for more. With each thrust, I let out a little more and it was very evident the pleasure was far exceeding any pain I may have been experiencing. I could feel my own cock, pressed against a leg of the table fighting to reach an erect position. I finally moved my body slightly enough to feel my cock pulsating between my legs.

Having sex with Tim brought back memories of being fucked by strangers in dirty hotel rooms. I would never have allowed any of those men to take off their condom, yet here I was thinking it would be ok. Just this one time, I kept telling myself. I knew the moment was coming, and I wasn't sure how to react. Part of me wanted every drop of Tim's cum inside me. The other part was hoping he would be caught off guard, shoot his load in the condom, and it wouldn't be a question. Apparently, I had already given him my answer.

Tim withdrew his cock quite suddenly, removed the condom just as quickly, and re-inserted his cock inside me without a moment of hesitation.

"If I gave you any time to think about it, it would have ruined the moment," he explained as he slowly began thrusting his cock in and out of me again.

"You drove two hours to get this, you slut. And I know you're loving every second of this. At the end of the day, you're just another slut. That's all you are. I don't need that good girl in your head telling you otherwise."

I didn't respond. He was right. It was the early morning hours. I was dressed like a whore. Acting like a whore. Now, I was being fucked like a whore. As conflicted as I thought I would be, it was quite easy to forget my safe rational thoughts as Tim's hands tightened around my hips and pulled my ass harder onto his cock. His hands would slide up under my bra and grab my breasts. It was moments later I felt the first stream of cum inside me, followed by stream after stream filling me up to the point where it started leaking out my hole and down my balls. He pulled his dick out, turned me around, and quite forcefully pushed my head down on him. My tongue and lips went to work on his still pulsating cock licking it clean of all his cum. Instinctually, I opened my mouth to show him I had indeed swallowed every drop of cum that wasn't inside me already.

I started to rub his thigh, thinking he would be ready for another round. Tim had other plans.

"That was great, and I'll need to fuck you again soon. Not tonight though. Get dressed and get the fuck out. I'm fucking exhausted and I want to sleep."

"Well fuck you too," was the first response I could muster as I grabbed my dress off the floor of his sleeper and started to dress.

"What do you want from me?" was his reply. "You came to me. I came in you. Good night. Goodbye. Sorry."

"Yeah, all good. Whatever."

There was no passionate kissing. There was no round two. There was just me putting myself back together hoping that I was grabbing everything I brought with me. I caught a glimpse of myself in a mirror. I was a hot mess.

"OK. That's everything. See you around, I guess," was all I could manage as I climbed out of the sleeper, into his cab, and out this passenger side door. I'm not sure he even muttered a goodbye.

I made sure I had my phone and my keys as I made the walk of shame back to my car. The walk seemed twice as long as it was when I got there. At that point, I don’t even care how I looked. I got in my car and drove back to my hotel in silence. My ass was burning in pain. My face was a mess. There was dried cum in my wig. None of this was how I envisioned this would go.

The first hour of the drive back, I swore this would never happen again. I was done.

By the time I got back to my hotel, I was planning my next night out and was certain I could, and would, recapture what I had previously held dear to my heart. My story would not end at the truck stop. In fact, I was convinced there was plenty of my story still to be told.