On the Road Adventure Ch. 02

I boosted Leslie up into my rig, and he explored. It was obvious that the expanse of the cab, and even moreso, the bed, surprised him. As I pulled out onto the interstate, he eased back into the seat, and watched from my motorized tower, the traffic, and the scenery. After a while, he drifted off to slept, as many do, on their first trip in a rig. The road lulls you. I let him rest. I had no idea how long he'd been on the road, or how long since he'd slept. I checked out his feminine appearance, deciding I'd made a good choice, in offering him a ride. After a couple of hours, his eyes blinked open, and it took him a few seconds to figure out where he was. A slow smile followed, and he looked over at me.

"Thanks for feeding me and giving me a ride. I still don't know where I'm going, but at least I'm going." I saw his eyes drift down to my crotch. After a couple of minutes he continued, "Um... I could...you know... if you want." Looking somewhat unsure of himself. I grinned, unzipped, and fished my dick out. It wasn't hard, but just the thought of those sweet lips was working.

"You can ... (pausing for effect) anytime you want, Honey." He took another look out the windshield, as if someone could actually see, then leaned over and timidly took my stiffening dick into his fingers. Even his hands looked girly. My mind was made up, I am making him my little bitch. As his lips slid over my head, I was thinking of places up the road to buy him, no, HER, some new clothes, and maybe a little makeup. She was clearly still experimenting, and taking her time, licking, kissing, sucking on me. A slow burn was fine with me, I liked the buildup. She would utter little moans when tasting my precum. She'd glance up, to see my reactions, eyes shining, as she'd realize how good she was making me feel. Even when I filled her mouth with hot cum, she slurped, and licked until there was nothing left. Little fingers kept sliding over me, keeping me from going completely soft.

Finally, she sat back up, grinning like a Cheshire cat, licking her lips. She was as pleased with herself, as I was. A couple of hours later, she didn't even ask, she just dropped back in my lap and started over. Oh, Hell, yeah, this was a smart move. A few more hours later, we rolled into a medium sized city, and I googled some clothing stores that would be easy to get in and out of, in this rig. When I mentioned shopping , She looked unsure, but bounced out of the truck, anyway. I had her trust. She DID looked surprised when we headed to young women's wear, searching my face, but saying nothing. I picked out a few outfits, led her to the dressing rooms, and handed them to her. She looked sheepish, but said nothing and went in. After each outfit, she would peek through the narrow opening, making sure no one was close, then open the door , for my approval.

"Perfect, baby! You look great." Then we headed to the shoe section, picked out some sexy heels, and one pair of girls sneakers, then to the makeup aisle. Here is where she looked more unsure, but did help me pick out what we thought she needed. Last stop was underwear and some Nair. She looked really unsure about that, but never said anything. We took our purchases, got back in the rig, where she sat there, deep in thought. "You're gonna be fine, Leslie, trust me. You're a natural." She just nodded, and dozed off again. She slept through me driving the rig back into the company lot. I woke her and gathered her backpack, and new clothes, and we transferred them to my boat of a sedan. When we got in, she asked where I was taking her. When I answered, "Home", she smiled, and looked out her door window, as if she'd recognize anything.

I unlocked the door, held it open for her, and let her look around. "You can stay as long as you like, ok? No pressure. If you don't want to stay, I can give you some cash, and a ride to the bus station, right?" She smiled, nodded, continuing to check out my small place.

"There's only one bed."

"That's right. If you don't want to share it, I think I have a sleeping bag somewhere. But, for now, why don't you get a shower, use the Nair, and, try on whichever outfit you'd like." She picked up the shopping bags, and closed the bathroom door behind her. It seemed like an hour after I heard the shower turn off, that she slowly opened the door, and stepped out. FUCK. I KNEW she'd be cute, but damn, NO ONE, not even her own mother, would have recognized her. She did the makeup like an expert, and had even styled her hair more feminine. Her legs looked amazing in the heels and short skirt. It was then I realized we forgot stockings, but they can wait. I whistled, and she blushed. But Smiled as big as possible.

"Damn, Leslie, you are beautiful! You know that, don't you? See? I was right, you look so damn good." She felt it. Even though she was a little awkward in the heels, she kept walking around, watching herself, and me. "I think we should celebrate. How 'bout I take you out for a nice lunch, let you get used to being stared at?"

"Oh! Um...a-are you sure? I mean... in front of PEOPLE?"

"Hell, yes! I'd be proud to take you anywhere. Let me change into something nicer. You can practice walking in heels while I get ready."

I walked her out to my car, opening the door for her, and watching her skirt ride up as she sat. I got in, and buckled up, she crossed her legs, and fidgeted with the hem of the skirt. Yeah, she was nervous, but clearly aware of how she looked. It was hard to keep my eyes off her legs. I never gave a thought that she wasn't all girl. We pulled into a nice restaurant, and I opened the car door for her, watched as she swung those legs out to stand up. She was going to turn some heads. We got a table, and she kept side glancing at other tables, whispering,"Are you sure this is ok? What if someone sees that I'm not... Not... real?" I laughed, and told her to take a look around. At least four men, some with wives or girlfriends, were openly checking her out.

"EVERY ONE of these guys is wishing they were me, Honey. Stop worrying." After that ,she relaxed some and we had a good time. I told her a bit about my life, and she shared some about hers. I particularly noticed that this time, she ate daintily, not stuffing herself like she did on that first meal I bought her. Amazing how smoothly she eased right into her new life. After we got back in my car, she leaned over, kissed my cheek, and thanked me for taking her out. I sat there a few minutes, Googling other stores, for things I'd overlooked on our first shopping trip. First, a women's shop, where we got her several pair of stockings, a couple of nighties, and a couple more bras, and nail polish. I made sure to get bigger than a training bra, as our next stop was an adult store, where I bought her, much to her embarrassment, silicone cups. Back in the car, I watched as she ran her fingers over them, feeling how real they felt.

When we got back to my place, she immediately headed to the bathroom. She emerged, pushing out her new breasts. It was plain to see that she loved the look and feel. She walked straight to me, tiptoed up, and pressed her lipstick lips to mine. When she didn't pull back, I wrapped my arms around her, and her arms went up around my neck. My big hands cupped her bottom, and pulled her into me. Her eyes flashed open, and I scooped her up, carried her to the bed. I eased her on it, She sat up, shook her head no, and pulled at my belt. She unbuckled me, unzipped me, and let my jeans fall to my knees. I was hard, and she dove for it, taking me in her mouth, like she was starved for it. After sucking and licking on me until I was almost ready to pop, she looked up at me, and whispered, "I think I'm ready" and she turned on the bed, on her hands and knees, and wiggled off her panties. I pulled out the bottle of lube we got at the store, and coated my dick, and her little bud. I crawled up to her, pressing my head against her.

"I'll go slow, I don't want to hurt you." She grasped as the head eased in, but she tightened up, and whimpered. I stayed there, letting her get use to me. Damn, what a firm ass she had. I rocked slowly back and forth, inching in a little at a time, until she grasped and backed into me. Her body shuddered as she took me in to the hilt.

"Ooooh my God!!. It's so big in me, but...I want it. MMM, yess, yess... Fuck me good. I-I never imagined it would feel like this!" I fucked her for over an hour. Getting so close, then stopping, rinse, repeat, until she begged me to cum in her. She was dripping on the bed, and I finally shot her full . She screamed out when I did, but not in pain. "Yessssss, Yes!! Feels so damn good!" We lay there a while, I nodded off, but woke up to feel her on top of me, riding my dick like a pro. Her face was radiant as she bucked on me. After 3 rounds, we slept through the night. The very next day, We visited a lawyer, to get her ID changed to Female, and applied for a marriage license. She now goes on the road with me, and even drives a little.... when her face is not in my lap.