Road Trip 5 (Patreon)

After the debacle with her picture, Anna was silent, her attention firmly on the drawings, avoiding my attempts to initiate a discussion. I didn’t bother much, as it was clear that she had firmly defined her identity based on her strong academic credentials, and her lack of physical allure, and with one move, I had broken through the latter pillar of her outward personality. No wonder she was confused. 

Of course, I was familiar with female psychology enough to know that the effectiveness of such a move relied quite a bit on her existing attraction. If I was a skinny nerdy boy, she would have dismissed it as an attempt of trying to seduce another nerdy girl. It was weird just how several pounds of muscle and a symmetrical face could make a man more trustworthy. 

Since she was more interested in processing her shock rather than speaking with me, I asked her to go back to RV, to start driving. The current camping area was nice, but not enough to spend two nights in a row. While I drove, she sat on the couch, making a show of keeping her attention on her e-book reader, though I didn’t miss that she had put my drawings to the table, close enough that she could glance on them whenever she wanted, followed by a long look at her reflection on the mirror, as she desperately tried to compare the two. 

I wondered whether she was trying to convince herself that my drawing was true, or false… 

The drive until noon passed in silence, until I saw a large mall in the middle of nowhere, completely empty. It was one of the huge malls that were built in the middle of nowhere at the intersection of several cities, to allow bargain hunters to shop for a full day. Those places were always packed at the weekends, and saw a decent crowd in the evenings, but at midweek noon, they were more like a ghost town. 

Perfect time to buy a couple of things for my wayward passenger if I could convince them. 

“Are you up to eat something that wasn’t frozen or from a can?” I asked, but took the exit without waiting for an answer. 

“That would be nice,” she answered, which didn’t surprise me the slightest. She stayed subdued even as we parked the RV, found a nice but inexpensive restaurant with a lot of selection, and joined my idle talk only when it was necessary as we ate, clearly trying to gather the courage to breach the subject, but failing repeatedly. 

Only when we were waiting for the check, she managed to ask it. “Do you really think I’m actually beautiful,” she whispered hesitantly. 

I could have just laughed it off, or gave her a quick answer, but that wouldn’t work well for my intention. Instead of answering instantly, I met with her eyes, and she stayed hypnotized by the sudden sharpness of my gaze. “Do you want me to prove it?” 

The way her breathing quickened was beautiful, especially when it pushed her chest up, enough to give a hint of the treasure underneath even with the sack she was wearing that was disguising itself as a t-shirt. Even with my experience, I could have never guessed the true beauty of the treasure that lay underneath her ugly clothing if she hadn’t been ‘kind’ enough to give me an extended show the last night. Even then, it was hard to believe the last night wasn’t just a dream. 

For a moment, I was afraid that I had pushed too much, that she was about to reject my nebulous offer, but after a minute of tense silence, she whispered. “How?” 

“Let’s start with your posture,” I whispered as I slid my chair closer and put my hand on her shoulder, enjoying the way she trembled as my touch slid down along her spine. “Push your chest a bit more, and straighten your shoulders. The first step of being beautiful is to own it. If you lack the confidence in yourself, no one would truly think you’re pretty, no matter how cute you are.” Then, with a widening smirk, I added. “And believe me, you are cute.” 

“R-really,” she stammered, unable to handle the full strength of my crooked smirk. 

“Of course, why would I lie,” I said even as I continued to caress her back despite it being unnecessary. Normally, I would have been slower when flirting, but considering she had chosen to molest me while sleeping, she didn’t deserve such considerations. No, she was about to receive a full blast of my flirting. We fall silent, but I kept my hand on her back, trailing down to the small of her back, making her shiver. 

I only pulled my hand away when the check arrived. I paid the check and we left the restaurant, though only to put my hand back on the small of her back when she tried to turn toward the parking area. “Where are you going?” I asked her. 

“To the RV?” she questioned. 

“Not yet. Did you forget that I need to prove something to you?” She looked at me questioningly, and I smirked. “We’re going shopping.” 

“No!” she gasped, panicked. “I hate shopping! Please.” 

“Sweetie, you don’t hate shopping. You’re bad at shopping,” I said, then paused. “Or, your mother is bad at shopping.” Her blush suggested that it was the second option. She still looked resistant, but I kept my hand on the small of her back as I led her toward a large department store, acting unaware of her blush as we passed a high-end lingerie store. As much as I would have liked to get her there and try some lingerie, I didn’t want her brain to melt in shock. 

"Don’t forget to stand straight even as you walk," I reminded her, giving a few detailed requests. She immediately did as she was told, lifting her head up, straightening her back, and without realizing it, pushing out her plump tits out enough to get the attention of the passersby, both male and female, though she was luckily unaware of the last part, too distracted by my touch. “Now, let’s move onto the next part, try to move your hips a bit more.” 

“But-” she tried to say, but I wasn’t above cutting her off by pressing my fingers to her lips, which silenced her perfectly in exchange for another thick blush. 

“No, you definitely have the hips for it despite the best effort of those abominable sweatpants. Shake your hips more,” I ordered, followed by several practical commands to best achieve the effect. One good advantage of being a painter who moonlighted as a bouncer was to have a very good relationship with several models, who spent most of their time in the club so relied on our protection, but also fascinated by the idea of a classical painter —mostly from the narcissistic angle of immortalizing their beauty in a different form. I had been commissioned a great number of naked portraits, and I was rarely get paid with money. But since most of them weren’t the sharpest tool in the shed in terms of interesting conversations, I had often defaulted to asking about their modeling experiences and techniques, the only thing their expertise that could be helpful for my own painting career.

Luckily, the outlet mall was huge, so we had quite a bit of distance to practice. Five minutes later, at the entrance of the huge department store, Anna’s walk had transformed from the boring lumbering of a nerdy girl to the beginnings of a sexy strut. She obviously had a lot to improve, of course, but luckily, we also had quite a bit of time.   

I couldn’t help but chuckle as she stood in the middle of the department store, no different than a quarterback who was asked to solve a complicated physics problem on the whiteboard. I chuckled as I led her toward the female side. There were only a few customers, and since most of them were over sixty and killing time in their retirement, I had no problem focusing on Anna. “Let’s start with something simple,” I said as I quickly picked several t-shirts, all of them tight enough to reveal her beautiful figure without being too sexy. They weren’t my ultimate aim, of course. I just wanted her to get used to wearing something a bit more form-fitting while I searched for something more impressive. 

She blushed, but didn’t resist when I grabbed her hand and dragged her toward the dressing rooms. After she disappeared behind a thick curtain, I went back to the store, quickly picking several more items, including some really tight jeans, skirts to put her deliciously-thick thighs on display, as well as tank tops and spaghetti-straps to finally pay her top the respect it deserved. 

When I arrived, she was still behind the curtain. “How are you doing?” I asked, faking concern. “Everything alright?” 

“Y-yeah, perfect,” she stammered even as the curtain moved with a sudden wind, suggesting that she had jumped in shock at my words. “I have just put on the t-shirt.” 

“Excellent,” I said as I pulled the curtain without a warning, making her gasp in shock. “What,” I shrugged carelessly. “You told me that you’re ready.” 

Even when she had already told that she was dressed, pulling the curtain open without her permission was still an overreach, but Anna was far too shy to defend her in such a nuanced topic, and let it slide. Instead, she stood in front of me, fidgeting, her arms crossed around her chest. “How do I look?” she whispered. I shook my head disapprovingly. She blanched, with the beginnings of tears appearing on the edges of her eyes. “You think it’s ugly.”

“No, I’m disappointed because you already forget your lesson. Keep your shoulders up, your back straight, and maintain eye contact. You are beautiful, own it!” 

“R-right,” she stammered panickedly, but her sadness evaporated, which was a win. She followed my command, the motion straining her t-shirt even more, proving that it was tight around the chest. “It’s a bit difficult,” she admitted, her social anxiety rearing its head. 

“Don’t worry, you look beautiful, but that t-shirt is not you, try the others,” I stated, and after a nod, she pulled the curtain close. I didn’t pass the other items I had picked for her, not wanting to scare her before she got used to modeling for me. Luckily, they had a couple of seats in the changing area, allowing me rest while she tried about six different t-shirts, none of them particularly impressive. More importantly, however, by the second one, she started remembering to stand without slouching like she tried to hide her body, and by the fifth one, her arms stopped flinching while she suppressed the desire to cover her chest behind her crossed arms. She was beautiful. Too bad that her bra was ruining the impact of her clothing. 

“That’s the last of them,” she said, her blush continuing to spread. “Shall we go?” 

I couldn’t help but chuckle as I pointed at the small pile next to me. “What are you talking about, we’re just starting,” I said even as I grabbed three jeans I had picked for her, and passed them on, despite my desire to see her in a miniskirt and low-cut spaghetti strap combo, especially if I could convince her to get rid of that ugly monstrosity that ruined the reputation of bras all around the world.

Maybe I should start working on that particular detail immediately, I decided as I walked to the underwear section, and started browsing, looking for a sexy set that was also cheap. Luckily, we were in an outlet, which meant I had a wide range of selections, especially since Anna’s sizes were not exactly flying off the shelf. She was somewhere between DD and E, and considering her relatively thin body meant that she was competing with a very small subsection of the population for clothes. 

After some browsing, I found a cute baby-blue lacy set, strong enough to contain her assets without sacrificing much from sexiness. They were not the best options, of course, as that honor went to a transparent red set that wouldn’t look remiss on a stripper as she strutted to a private dance. Too bad that Anna would probably faint if I asked her to wear them. 

However, I still put them in my shopping bag, as just because she didn’t wear them today didn’t mean that I couldn’t convince her to wear them later on. 

A wide smile adorned my face as I walked back to the dressing section, the baby blue set lacy set in my hand, anticipating an amusing reaction. She didn’t surprise me when I arrived at the screened section that held the dressing rooms. Anna was waiting for my arrival, while also twirling in front of a mirror, examining the reflection of her hips under the tight wrap of her jeans. It looked exemplar. “How do I-” she started asking, only to freeze when she noticed what I had in hand. “That’s too much,” she gasped. 

“That’s another lesson, wearing sexy underwear adds to your confidence,” I explained, and when she looked panicked enough to abort, I quickly continued to recover the situation. “Only you’ll know what you’re wearing underneath, but still, it will help a lot,” I added before moving to the final blow, sounding just vulnerable and disappointed enough. “Don’t you trust me?” 

“Of course, I do!” she answered immediately before she could even think, inadvertently locking herself into the situation, and I had no intention of allowing her to extract herself. 

“Excellent,” I said as I pulled off its price tag. Unlike the other items, shoppers were not allowed to try out underwear without actually buying, but I trusted my sense of measurement enough, especially after receiving such an extended show the night before. Her naked figure was still firm in my mind. 

“But-” she tried to interject, only to be cut once again. 

“Don’t worry, they are in deep discount, just a couple of dollars,” I explained. “I can gift them to you if you want,” I added without prompting, and making her blush enough to retreat behind the curtain. 

I was about to pass the underwear to her by pushing the curtain, when I was struck with a fancy and added one of the tank tops to the package. It was a black one, and the most conservative among the items I had picked with almost no cleavage, but still, it was miles better than the t-shirts earlier, thanks to their elastic nature if nothing else. “Thanks,” came a muffled sound from the other side of the curtain, followed by a subdued shuffling, suggesting that she was trying out my gifts. 

I couldn’t wait to see her new style…