I swear, this is a true story.
A few years ago, I was supplementing my income driving for Uber, and also giving my friends massages (I trained, but never finished the classes. I have a story about that for another day.). I’d only drive on Friday and Saturday nights, because that’s when you can make good money in KC. Most weekends, in fact, all but two weekends, were pretty normal. Pick up a rider, drop them off, over and over again. If you’re lucky, sometimes your rider is a good conversationalist.
One Saturday night, I picked up a woman fairly early in the evening, probably around 9:00 or so. At first look, I thought she was girl-next-door pretty, and had a nice little athletic-looking body. As it was summer, she was fairly skimpily dressed. Shorts, tank top, button-up shirt hanging open, and cowboy boots. She looked like someone I’d ask out if I weren’t her driver. I try to not overstep my role.
During the ride, we chatted about whatever normal topics came up; job, weather, whatever. But then I asked if she was going to party late tonight. She surprised me by telling me that she and one of her girlfriends were going to “try to get laid”! Man, I was SO CLOSE to overstepping the line, but I maintained my role, and simply said “Shouldn’t be a problem, the way you look”. She laughed it off, and we just kept chatting. (I will admit that I am definitely an idiot.)
Since she opened the door, the conversation evolved into sexual topics. And my plans for late that night changed drastically when she admitted to me that her biggest turn-on is being watched. Before that, due to the sex talk, I already had a semi-stiffy. As soon as she said that, rock hard. She didn’t know, but I love watching a woman pleasure herself. “We’re a match made in Heaven”, I replied. “I LOVE to watch. I think a girl is sexiest during the throes of passion.” She looked at me with a smirk.
All good things must pass, and the ride came to an end. I will give out my personal cell phone number to certain people, so they can call me directly for a return trip. I only do it if I know I’m gonna be out all night, and if I really like the person. (I know I’m not supposed to, but I’m not the only one, so don’t judge me.) I had her put my number in her phone, and told her she could call me when she’s done for the night. That was a GREAT decision.
When she called, around 1:30 or so, I had nobody in my car, so I drove to Westport (a party area in KC) to pick her up. I was pretty surprised that she wasn’t drunk, and she was alone. With a laugh, I asked if she’d been successful. “Lots of boys out tonight, but no men.”, she replied. “Anyways, I’m tired and ready for bed.” To me, that was a signal that she didn’t consider me one of the men she was looking for. Oh well, I was getting paid, and she was fun to talk to.
Just before we reached her apartment, she threw me a hint that I would have been an idiot to ignore. “Have a good night, and if you’re in the neighborhood, I sometimes leave my blinds open. My room is on the back side, overlooking the river.” For the first time that night, I was absolutely speechless. She was literally inviting me to peep on her. I need to take this opportunity to say that I am not now, nor have I ever been a Peeping Tom. But when a girl like that gives you a hint like that, you’d be a fool to ignore it, right?
I played her game, and I drove off. All I really did was go park the car. At nearly 2am, I expected to see very few rooms lit on the back side of her complex, and I was right. There was only one. (Not sure what I’d have done if there were several.) I approached cautiously, clinging to the shadows. When I got to what I assumed was her apartment, I was not let down. Though the blinds weren’t completely open, they were turned allowing easy vision. She stood facing away from me, but it was definitely her. She had removed the button up, but was still wearing everything else. I watched as she sat on the far side of the bed and removed her boots and socks. Then she stood, and peeled off the tank top, her b-cups covered only by a lacy white bra. Next came the shorts, and I was rubbing myself through my jeans as I watched her slide them down her beautifully tanned legs, and she was left in a matching undergarment set, no doubt a reward for the man she was hoping to meet.
She sat on her bed, her back propped against a few pillows at the headboard. I watched as she picked up her phone and started thumbing through pages. I was hoping the show wasn’t over. I shifted my weight slightly, and inadvertently rattled some of the rocks I was standing on. She heard the noise and glanced my direction. Because of the lights being on, she couldn’t see me in the dark, but she knew I was there. She smiled coyly, and went back to her phone. Soon, though, she paused on what I’m guessing was a porn video. I could hear no sound, but she stopped turning pages. After a minute or so, her right started caressing herself, first a thigh, then up to her tight stomach. She moved them to her breasts, and I was treated to her caressing her nipples through her bra, and I could see them harden at her touch. One after another, she slid the straps off, and soon bared them both for me. Her breasts were nearly perfect, with quarter size aureoles topped by stiff eraser head nipples. She pulled on them with one hand, and put her phone down. Her other hand crept between her thighs, and started rubbing the lucky fabric. It didn’t take long before she pulled them off, too. Her fingers found her clit, and she alternated between rubbing herself and sliding first one, then two fingers in her pussy. I had my hand down my pants rubbing myself, afraid to pull it out. When she came, her back arched almost lifting her ass off the bed. Her eyes were closed and she was biting her lower lip so hard, I was afraid she was going to bite through. I came in my pants just a few seconds later, and nearly fell to the ground.
She looked toward the window, gave me a wink, and turned off the light. My night was over, for sure.
I’d love to go see her again, but without an invitation, I’d become a Peeping Tom, and that’s not me. I do hope to hear from her again one day. If you’re reading this, I hope you still have my number.