And Then She Winked

It was just after 3:00AM, and I was jerking off in my car.

Why was I jerking off in my car? Well, it's a long story. I had recently gone through some big changes in my life and tonight it all got to be too much. I had recently left my job for a considerably more stressful position nearly a hundred miles from home. The pay was better, and it had a lot more opportunities than my previous job, but it was taking its toll, as was the relocation that I was forced to undergo.

When I figured out that I was moving, my girlfriend, Brittany, decided that she didn't want to do long distance. We fought about it for over a week, and then decided mutually that we should break up. At least, I thought that we had decided.

She called me earlier this week and asked if she could come see my on Friday because she wanted to try and work things out. It had been a few weeks since I'd seen her, and I thought that even if it went south, (which of course it did) I might at least get some action. So I told her to come.

When I left work on Friday, I was frustrated. I was just getting into the thick of work, and it was demanding. So when I got back to my apartment, I had a beer. Then another. And another. By the time Brittany rang the buzzer, I was feeling a little drunk. I buzzed her in, and she wasted no time jumping on top of me as soon as I opened the door. After a few clumsy kisses, she reached for my zipper. I sank into the couch while she went down on her knees, getting ready to blow me. She took off her top and was left in a very sexy pink bra. Right about then, things did in fact go south.

As she lowered my pants, I reached behind her back to try to undo her bra. Because I was sitting on the couch, this quickly turned into a very awkward position. Still feeling the buzz from my beer, I fumbled with the strap far longer than I should have. I was getting very frustrated very quickly with the whole situation, and then I let some of that frustration out and tore the damn thing open. The strap snapped against her skin as I pulled it apart, and she let out a little scream of pain. She looked up at me from the floor with anger in her eyes. She started screaming about the bra and how expensive it was. And then she started yelling about me drinking, asking me if I felt like I had to be drunk to be around her. And so on from there.

I would like to say I apologized and tried to make amends with her, put her worries at rest, and soothed her until she felt better. But I didn't. Everything was getting to be too much, so I yelled right back. After a few minutes she left, slamming the door behind her. I sat on the couch, angry at nearly everything in my life.

My pants were still around my ankles, and suddenly I found myself thinking about Brittany standing there topless, screaming at me. I don't know why, but I found it really arousing. I started stroking my cock right there on the couch, thinking that maybe I could just jerk off, go to sleep, and deal with everything in the morning. But first, I got up, downed another beer, then came back and started jerking again.

Now might be a good time to mention that I have a roommate- Jake. I hadn't mentioned him before, because he was supposed to be out of town for the weekend on a trip with his girlfriend, Paige. But he was about to make my night even worse.

As I was sitting on the couch, jacking off, I started to hear a key turn in the lock on the front door. I scrambled for my pants and barely managed to pull them up before the door opened. Jake entered, followed by Paige, both seeming to be very drunk. A man entered the apartment right after them, breezing past Jake and Paige into the kitchen.

"Jake, Paige, what the fuck? I thought you were going on a trip this weekend." Jake started to slur an answer to my question.

"We were. But then we got bumped from our flight. Went to a bar instead. Had a few drinks, met Tommy Boy here and said fuck it, we'll party at our place!"

"What are you talking about? Who the hell is Tommy?"

"Tommy! Tommy Boy! The guy that just walked into the kitchen!" Paige seemed even more drunk than Jake. "I think there are a few more people from the bar coming too."

"Are you kidding me? What the hell man, you can't just invite strangers over here without even telling me first!"

"Relax, man. They're cool. Hey, barn door, bud." Paige giggled as Jake pointed out that my zipper was down. Frustrated, I stood up, picked up my keys and walked out of the apartment. I opened up my car and got in, but didn't put the keys in the ignition. Instead, I simply lay back in the seat, fuming. I realized that my fly was still down, and reached down to fix it. As I pulled the zipper, I got it into my head that I was still pretty horny. I looked around the parking lot quickly and found no one, then unzipped again. I pulled out my dick and started stroking, just like before. By now however, I was feeling really drunk and couldn't get anywhere. Eventually I passed out, with my dick still in my hand.

I woke up in my car and looked around the parking lot again. It was still dark outside. I took my hand off my member and fumbled around for my keys. I stuck the key in the ignition and looked at the clock. It was just after 3:00AM. At this point, my balls were starting to ache from being interrupted all night. Looking back at my apartment, I saw the lights still on in the window and heard music reverberating from that direction. Thinking that my apartment was still full of strangers, I decided that this was probably my best option at this point for privacy. So for the third time that night, I started to masturbate. Which brings us back to the beginning of the story.

It had barely been a minute when I caught movement out of the corner of my eye. I stopped stroking for a moment and looked around. I couldn't see anything outside my car, so I thought I was safe and resumed.

After another minute, I saw it again. I stopped abruptly and turned my head to the right. Nothing. I waited for a few seconds, then cautiously began to stroke again, keeping alert for movement.

After a couple of minutes, I made up my mind that I was being paranoid and I just wanted to finish and go to sleep. I started stroking faster, and then I saw her.

In the driver's seat of the car on my right was a gorgeous redhead. From what I could see, she was petite, wearing a black dress, she had perky little boobs and the most adorable freckles that I have ever seen. And she was watching me. I turned my head fully to the side and stopped masturbating, wondering just what the hell this girl was thinking. I started worrying that she might call the police, and thinking just how badly that would end.

And then she winked.

She pursed her lips like she was giving me a kiss, and winked. Clueless, I sat frozen, not breaking eye contact with this beautiful stranger. She raised her eyebrows as if to ask me why I had stopped. Still, I didn't know what to make of the situation and remained still. Finally, she started to nod and used her hand to mimic my stroking.

Stunned but apparently encouraged, I slowly reached down and started to stroke my dick again. She smiled when I did, watching intently. I kept going slowly. This was the first and probably the last time something like this would ever happen to me and the fact is I had never been so turned on in my life. After a few minutes, the redhead started to look bored. I picked up the pace a little, but to no avail. She even turned her head away and looked out into the night. I feared that this was the end of our adventure.

Imagine my surprise when she turned back and pulled her black dress down to her waist. I became suddenly aware that she wasn't wearing a bra. She winked at me again then plunged her hand down and out of my sight, towards what I assumed to be a dripping, panty-covered pussy.

Minutes ticked by. The redhead came once, while I struggled not to do the same. As she came down from her orgasm, she seemed to be getting bored again. Looking down at the dashboard clock, I noticed it had been nearly half an hour of this. I was still very much aroused, but I couldn't blame her for not seeing any change from me for this long. I started to stroke faster. I looked over to see her looking around again. I was getting close to the point of no return in my own masturbation, so I closed my eyes and leaned back in the seat for a moment. Then, a tap on the window.

I jumped in my seat, hitting my head on the roof of the car. I panicked, thinking it could be my roommate, or a cop. Or worse: Brittany. The redhead was outside my door, giggling. I unlocked the door and she crawled in onto my lap. She sat facing me, her dress bunched around her waist and her bare slit resting on top of my cock.

I looked into her eyes for a moment, and she into mine. I kissed her. She kissed me back. I kissed her again and again, each time eagerly matched. As l leaned in for another, she shifted on my lap and guided my cock right into her inviting little snatch. And then we were fucking.

It was animalistic and loving at the same time. Here we were, two strangers, fucking like rabbits in a parked car. Primal like teenagers, but with the tenderness of lovers. I didn't last long, but luckily, neither did she. My cum filled her pussy as it clenched around my cock. We stared into each other's eyes for a long moment, until finally she leaned back and opened the car door.

She fixed her dress so that she was no longer exposed, and stepped out onto the pavement. I pulled my pants up and started to get up after her, but instead she leaned down and put a finger to my lips. She kissed me once more, pulled away, and winked at me again. The same wink that she had given me when I first saw her. She walked over to her car, got in, and drove off.

As her car disappeared from view, a flood of thoughts came into my mind. What the hell was that? What if anyone saw? What if she's got something? What if she's pregnant? What if I never see her again?

Somehow, in that moment, the last question was the only one I cared about. I waited for just a minute before I finally got out of the car and went back inside my apartment. I could see Jake and Paige passed out in Jake's bedroom through their open door. Tommy Boy was passed out on the couch. It didn't look like too much damage was done to the apartment. Feeling slightly numb, I went to my own bedroom, shut the door, and fell asleep on top of the covers.

The next morning, I awoke with the questions from last night still on my mind. I was seriously worried about diseases or pregnancy, but mostly I lamented the fact that I would never see her again. I took a shower, got dressed, and found Jake and Paige sitting at the kitchen table. No sign of Tommy Boy.

"Looks like you two had a rough night," I said as I entered. I got some gruff mumbles from both of them as a response. "You guys want to go grab some breakfast?" More mumbles. I gathered that they weren't in a mood to eat. "Well, I'm going out. Text me if you guys change your mind."

I stepped outside the apartment and took a breath of fresh air. As I turned around to lock the door behind me, I heard the door of the apartment behind me swing open. I turned back and there was the redhead from last night. We stared at each other in surprise for a long moment.

And then she winked.