Sitting in my car on a cool March night, I was trembling. To the passerby, I was just a mid-20s guy in a hoodie with long black hair…but they weren’t the only thing I was wearing. Suddenly, there’s a knock on my passenger side window. I just about jumped out of my skin. “Hello?” asks the tall man, peering into my car inquisitively. My heart catches, my stomach drops. It’s him.
A year earlier, I met him online. I had made a post on a meetup website, bored and brave one afternoon, where I posted an ad: I wanted to dress up in something cute, something girly, something sexy, then have some fun with someone. I didn’t expect any replies, but I got a couple, although most of them were creepy and insensitive. Then, he messaged me. He was different, kind and understanding. I told him I didn’t actually own any cute girly clothing. A week later, a package arrived at my door. Inside was a peach dress, backless and armless that covered my entire chest up to my neck and fell down around my mid-thigh. Along with the dress, a pair of American Apparel white gym socks that ran up the entire length of my leg. Then, hidden at the bottom, a small sky blue thong. It all fit perfectly. I tried it on and took photos at his request. I posed and flaunted around my room. It felt amazing. The dress fluttered and I could feel my thong pulling tight up my butt. I felt girly.
Over the next few months, he sent more clothes. Swimwear, stockings, garters, nighties, panties. We flirted online, then I finally found the courage to talk over the phone. His voice was deep, while mine was restricted to a light whisper out of nerves and excitement. We talked about meeting up, but nothing came of it. We’d set dates, then my fear would get the most of me and I’d pull out. We dropped out of touch. Then reconnected. Back and forth we went for a year. Then, finally, we agreed on a day. Saturday night, I would simply drive to his, and we could finally meet. He wanted to get a hotel room, but I wasn’t ready for that. The car would be enough for now.
That day, I threw my outfit in a bag and wore baggy clothes. I went about my day, catching up with friends, with butterflies fluttering in my stomach. Finally, darkness fell. The drive only took 15 minutes, but it felt like forever. I parked a few streets away from his and got changed in my car. Off came my t-shirt, replaced by a dress. Off came my boy boxer shorts, replaced by the super feminine thong. Once changed, I put a wig of long black hair over my head, covering my regular short brown hair. Then, my hoodie and jeans went back over the top.
After knocking on the door, and scarring the hell out of me, he opened the door and climbed into the passenger seat. He was a good 4 or 5 inches taller than me, and was a bigger person too. He wore a large, black winter coat, covering a shirt and black jeans. I giggled nervously as I drove my car a few streets away to find somewhere more dark and private. We moved to the back seat, and he turned to stare into my eyes. Slowly, I undressed from my boy clothes, revealing the peach dress and long socks underneath that he had sent me so long ago.
He took a hold of my hand, running his fingers up my arm. “Is this okay?” he asked. I nodded, still highly strung and nervous. I grabbed his arm and softly moved his hand to my knee. Rubbing back and forth, slowly it crept higher. Pushing my dress up, he ran his hands over my thigh, reaching exposed skin. I gasped as I lay back in my seat. Slowly, his teasing fingers pushed my dress up completely, roaming a single finger over my light blue covered crotch. I gasped and jumped. He continued stroking me, eliciting small gasps and a couple of moans. Then, he leant in and kissed me. I went limp as his tongue probed my mouth, hungry. His hands began roaming all over my body. Kissing down my neck, he pushed my dress aside to expose my nipple, and sucked on it. All worked up, my head clouded by a lust-driven fog, I pushed him back and climbed over his lap. He lifted the back of my dress, exposing my thong clad ass and gasped. Suddenly I felt his strong hands groping me, exploring. A sudden smack stung my ass. Then another. Then another. In rapid succession, he spanked me. It didn’t feel like much at first, but then my butt grew warm. I began to squirm and moan, gasping before “Stop” escaped my lips in a struggled whisper. He chuckled. We both knew who was in control. Grabbing a hold of my thong, he pulled it up suddenly, forcing another gasp out of me. He pulled it up, tight, causing it to wedge deep into my butt, but also forcing my hips to buck against his. Then he did it again. And again. Forcing me to rub against his lap. Then the spanking began again. This all continued for a full minute before I asked him to stop. I almost came all over his lap.
Sitting up gasping at how intense things had gotten so quickly, we decided to stop there. I was in a bit of shock at how far I’d gone. I drove back to his and we said goodnight, but not goodbye. He knew I was addicted, and that I would have to come back for more.
Source: reddit.com/r/gonewildstories/comments/6cltyq/the_meet_up_a_car_in_the_dark_mm_cd