I’m an older man who has been through divorce, after a very long term marriage. During the time between separation, divorce, and entering another LTR, I drove rideshare for extra money and human interaction. Most of my time doing this was in a smaller but popular college town, but I also did my share of road trip funding in larger cities as well. To be clear, my main goal for driving the late night hours was responsibilty; kids, bills, survival. But I’m also very social, and it provided a way for me to interact with other humans and also get paid to do so. I believe these days for rideshare drivers are long gone. Here is my story of my first rideshare sex experience…
It was around 1:15am on a Thursday night. Thirsty Thursday was the theme at the local downtown bars. A typical night of rideshare driving was doing loops around the college residential neighborhoods, packing your ride with amped up college kids and dropping them off 2 blocks away. I found it both annoying and fun. I myself would have done this back in the day, if it were an option. As the night goes on, the rides get longer. People start migrating downtown to the bars around 10pm. So there’s this kind of odd time where you have to speed back to the residential neighborhood as soon as you drop off at the bars. Occasionally though, you pick up adults who are ready to dip out before the takeover. That however, is another story ;)
Fast forward past the yadda yadda. It’s around 1:15am and I get a ping to a Taco Bell, the hot spot for after bar munchies. As I pull up, there’s a young couple saying good bye to a tall girl, pixie type hairstyle and sports bra type top.. big tits, athletic body. They kind of push her into my ride, front seat. “Text us when you get home”. She’s like ” yeah, whatever” , and flips them off. She turns to me and asks if she can eat along the ride. No problem. She devours 2 burrito supreme’s in less than 3 blocks and burps. “s’cuse me”, she says, then looks over.. “you’re cute”. Then she grabs my phone and starts scrolling through apps until she finds snap. She leans in to me and kisses me on the cheek while taking the photo. She adds herself to my friends and sends the snap. By this time, we’re at her house. She instructs me where to park, and as soon as I’m parked she starts kissing me. Second hand Taco Bell is not as tasty as the original, but she has great tits, so OK. She grabs my hand and slams it on her tit. I go to work on it, while we tango our tongues. She’s breathing , moaning, grabbing my cock through my pants. I snap out when the next ride pings, and shut off my apps. She reaches for my zipper, undoes my pants and belt, and pops my hard cock into her mouth. My hand goes to the back of her neck, she moans and starts gulping until I explode. She swallows every drop, looks up at me and giggles, “come inside with me”.
Now I’m already spent and trying to come to terms with what just went down. It’s too late to catch anymore rides, so I go in and wait in the entryway for her to go to the bathroom. She comes out and takes off my hat. She giggles at my curly hair and hugs me tight. “come on”, she takes my hand and leads the way through the house. There are girls sleeping everywhere. A couch on every side of the room with a body on each. Her room has 2 twin beds, one on each side. We get into one and start kissing again. As I’m fingering her, someone else comes into the room and gets in the other bed. She climbs on me and I have to slow her down to ask for a condom. She pulls one out of a dresser next to her bed, and we get back to it. As she starts to ease onto me, I hear noise from the other bed.. squish squish, squish, gasp.. That’s when I knew her roommate was jilling to the sound of us fucking. It didn’t take much to make her cum, and myself as well. I don’t know what the roommate ended up finishing to. I stayed there until they were both asleep, and slipped out past all the other sleeping housemates.
Source: reddit.com/r/gonewildstories/comments/wvzdjn/mf_the_rideshare_years_my_first_story