I laughed a little to myself as I navigated the busy New York City streets. 'I am a pedi-cab driver!' i thought to myself. It still seemed a little surreal.
I come from a relatively wealthy family in New Jersey. I study accounting at school, and am likely to take over my dad's business one day, but for this summer off I had disappointed him by telling him I wanted to live in the city and had taken a 'job' riding a pedicab for tourists. He told me if that's what I wanted to do I'd need to pay my own way, that he wasn't going to pay one dollar. I didn't tell him I just wanted to get away, and of course, fuck as many girls as possible.
The inspiration came one night when my friends and I were bar hopping in the West Village and I had seen some drunk girls in the back of a pedicab. One of the girls flashed her tits at us as they rode past. At that moment I thought...what a cool job, the guy gets to ride around with pretty girls who are naive and drunk.
For some reason I couldn't get that idea out of my head. Why couldn't I be that guy, at least as a summer job? It turned out there was no reason at all, they were happy to have a 'responsible' kid on board. I found a shitty apartment to rent for a couple of months. My priority was that it was downtown and that I didn't have to share. I picked it specifically to take girls back to.
Overall, the job was a drag. I did need to make some money and most of my clients were older tourists, often overweight. They tipped well but it was hard work. Others were drunk people out on the town, often tourists who didn't tip well. The reason I took the job, my 'plan' actually did work a few times that summer...four to be exact.
On my first night riding I actually ended up fucking a woman who must have been 15 years older than me. She was in town for a convention and had stayed out drinking after her colleagues had gone home. She was pretty looped and said she didn't even remember where her hotel was, she said it was a 'big tall one near Times Square'. I looked her up and down. She was a little overweight and her hair was not well kept, but she was pretty and I actually liked big asses. I decided to just be direct and suggested she could stay at my place which wasn't far. She seemed surprised, but after a beat she laughed and said 'why not?' When we got in my little room I wasn't subtle. I pulled her close, kissed her, and she responded. I put my hands up her skirt and started feeling her big ass and she pushed herself against me. Soon I had her on all fours over my futon fucking her hard, almost angrily. She loved it and was impressed when I could go again shortly after. She seemed grateful to suck my cock, telling me how long it had been since she had done this. She stayed the night and the next morning realized she had the hotel address on her phone.
I thought I might get laid every night, but the next time my 'plan' worked, it was almost a month later and much more complicated. There was this young couple from Denmark, maybe 19 or 20. They had been drinking and asked where else they should go. I took them to a dive bar where I knew they wouldn't check id and let them buy me a drink. As we talked I found the girl, Anya, to be the more extroverted and even quite flirty. The guy didn't seem to love it, but he accepted it and I decided to see how far I could take it. When she put her hand on my leg while telling me a story, I did the same to her, and when neither of them protested I let it go up further, stroking her sensually. It was only at this point I thought I might actually get to fuck her. She was no beauty but she had long blonde hair and a tight young body. I knew they were staying at generic Hilton Garden and suggested they should come to my place and see what it was really like to live in NYC. He demurred but she liked the idea. I told them it was nearby, that I had some weed and soon Anya was pushing her boyfriend to go. It was pretty clear she usually got her way and soon I was pedaling them to my apartment.
When we got there I could see by the look on his face that he was extremely unimpressed, and I quickly rolled us a big joint to smoke. We all sat on my bed/futon and the vibe got more relaxed. Unfortunately he sat between Anya and I so it wasn't easy to make a move.
When Anya complained about how sore her feet were from walking all day I volunteered that I could offer an excellent foot rub. She laughed and told me to prove it and soon I had moved beside her. She faced me and proffered her feet. I tried not to make it obvious that I had a clear view of her panties as I rubbed one foot, anxious to make her moan which I did. When I went to change feet, she let the one I had been holding fall into my lap where it brushed against my hard cock. She did not move it, and by the way she looked me in the eyes it was almost like she was daring me to make a move. I pushed it further, starting to rub her calf, then her upper leg.
