Straight Male / 55
Traded Pass For A Handjob
About 5 years ago I had driven into a large city and parked on the street near a light rail station, then bought a day pass for the system so I could take it downtown and get on and off it several times to get to multiple destinations. I got back around 6 and then loitered around the uncrowded stop for a few minutes to see if anyone passing through wanted to use my pass for a couple bucks. The first couple people coming by already had passes or tickets, but then I started to overhear a woman on a payphone who sounded totally freaked out and desperate, it sounded like she was short on money and didn't know how to get to whoever she was talking to. As I made one last pitch to a passing woman who again had a ticket, I was about to give up and toss it, but the lady on the phone apparently overheard me and looked at me with a plea. We were soon talking alone and she said she had no money but really needed it to get somewhere. She was a reasonably large black woman, with a couple of loose bags, and honestly looked like she was having some tough times even without hearing her speak.
I hesitated and said maybe we could work out a deal. She again said she couldn't give me anything, but then I said I've had a long day downtown, and wondered if she could help me relax with a handjob in my car, which was just a block away. She gave me a kind of sad look, and said she wasn't that kind of woman but this was a hard day and we could make it quick. So in a couple minutes we got into the front seats and I quickly unzipped my pants and brought out my penis. Fortunately I was parked next to an empty lot, there were houses or apartment buildings down the block but no one was likely to see if we didn't take long. I was a little nervous at first but I touched her large boob through her shirt and asked her to suck my finger, which she hesitated to do but let it in for a second, which was enough to make me rock hard. She then grabbed my dick and started jerking me extremely hard, gripping me tight as she stared at me. I kept my eyes mostly on the street and sidewalks around us, peeled for anyone coming by. Someone was down the sidewalk a ways, but long before they reached us I was huffing and spasming, and gripped her shoulder as I started ejaculating into the air, spewing cum all over her hand and my lap. I yelped loudly as she kept pulling on me, then slowed down and twisted her hand around my cum-soaked shaft for a few more seconds. I handed her a towel from the backseat to wipe off her hand, then the rail pass. I said "thank you, I needed that," but she just gave me a head-shaking look and got out the door, walking back to the rail station. I had cum all over my pants but the mess was worth it.
I hesitated and said maybe we could work out a deal. She again said she couldn't give me anything, but then I said I've had a long day downtown, and wondered if she could help me relax with a handjob in my car, which was just a block away. She gave me a kind of sad look, and said she wasn't that kind of woman but this was a hard day and we could make it quick. So in a couple minutes we got into the front seats and I quickly unzipped my pants and brought out my penis. Fortunately I was parked next to an empty lot, there were houses or apartment buildings down the block but no one was likely to see if we didn't take long. I was a little nervous at first but I touched her large boob through her shirt and asked her to suck my finger, which she hesitated to do but let it in for a second, which was enough to make me rock hard. She then grabbed my dick and started jerking me extremely hard, gripping me tight as she stared at me. I kept my eyes mostly on the street and sidewalks around us, peeled for anyone coming by. Someone was down the sidewalk a ways, but long before they reached us I was huffing and spasming, and gripped her shoulder as I started ejaculating into the air, spewing cum all over her hand and my lap. I yelped loudly as she kept pulling on me, then slowed down and twisted her hand around my cum-soaked shaft for a few more seconds. I handed her a towel from the backseat to wipe off her hand, then the rail pass. I said "thank you, I needed that," but she just gave me a head-shaking look and got out the door, walking back to the rail station. I had cum all over my pants but the mess was worth it.
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