Straight Male / 55
Tomcatting
When I was young like maybe 26 or 27 I had a job working in a industrial park in the north end of my town. It was small factories and auto body shops and high rise housing project buildings.
I worked the evening shift from 4 to midnight and driving home I passed through a area bordering a park. This was a known street walker's stroll. Guys would drive through and pick a girl they fancied, stop and have a quick chat through the open car window. If the two agreed on a price the girl would get in and they'd drive either to the small parking lot or just park on a quiet side street. Mostly the girls were giving blowjobs for $20. They would fuck too, some in your car or van and some who would say they got a room but they need like $35 to help pay the rent. Or they'd have a room at a seedy hotel up the block, and again, you had to pay for the room by the hour.
I never went with any of these whores but was very, very tempted a few times.
Some slow nights when I'd stop at a red light by the side of the park, two or three or more girls would come over to my driver's side window and flash me their bare tits or their hips and ass. Some were just wearing nighties and some dressed slutty in tiny miniskirts or shorts.
Anyway, there was sometimes when I would stop and flirt and a couple of times I picked up girls and offered them money to just sniff their panties or to feel them and finger them.
There was this one latina girl, very petite and pretty and she smelled so sweet, I gave her ten or twenty dollars and she gave me her panties after she dug them deep into her pussy and got them soaked. When she was sitting next to me in my car with her panties in my hand, I used my other hand to stroke and finger her pussy real gentle. She had the softest, slickest, finest pussy I have ever touched before or since. That's like 30 years and three wives ago.
This girl was freaking HOT!
Reluctantly I let her go and did take her phone number but never called her or saw her again.
Another time I picked up a girl who was a Black trannie. I got her to give me her panties for around ten dollars and another twenty five to suck my dick.
Before getting the blowjob, we parked up this street that she pointed out. She was reaching over to open my pants when I changed my mind. I made her get up on the seat facing away from me and lifted her dress. She had already took her panties off cause I bought them so her bare ass was right there in front of me.
I rubbed her cheeks and she jiggled her ass and said she liked it in her "pussy". I was very turned on and wanted to kiss her dark brown hole but was too afraid of STDs and settled for a little fingering. It was making my dick throb having my finger deep in this hot fucking nasty asshole.
Suddenly there was flashes in the rearview mirror. A unmarked police car had either pulled up behind me or was there at the curb all along and I never noticed.
Now I was shitting my pants.
I had a new job and a nice conservative wife at home with my two little kids and I figured I was busted in a police sting or something. I didn't know what to do or say but knew I was in deep shit.
So the detectives got out and approached from behind on both sides. The one on my side says some shit like good evening sir can I see your license and registration and insurance card please.
The cop on the other side of the car is just looking around and the whore is smiling at him and telling the cop with my papers how I was just dropping her off and she lives up the block.
He looks at me, hands back my stuff and tells her she can leave then. She gets out and he tells me to go home and stop driving around the park checking out the whores.
I was so relieved I don't even remember the ride home.
I got home and vowed not to cruise the park on my way home again. I did have those panties under the bucket seat of my car and I used them to stroke off when I put the car in the garage.
I worked the evening shift from 4 to midnight and driving home I passed through a area bordering a park. This was a known street walker's stroll. Guys would drive through and pick a girl they fancied, stop and have a quick chat through the open car window. If the two agreed on a price the girl would get in and they'd drive either to the small parking lot or just park on a quiet side street. Mostly the girls were giving blowjobs for $20. They would fuck too, some in your car or van and some who would say they got a room but they need like $35 to help pay the rent. Or they'd have a room at a seedy hotel up the block, and again, you had to pay for the room by the hour.
I never went with any of these whores but was very, very tempted a few times.
Some slow nights when I'd stop at a red light by the side of the park, two or three or more girls would come over to my driver's side window and flash me their bare tits or their hips and ass. Some were just wearing nighties and some dressed slutty in tiny miniskirts or shorts.
Anyway, there was sometimes when I would stop and flirt and a couple of times I picked up girls and offered them money to just sniff their panties or to feel them and finger them.
There was this one latina girl, very petite and pretty and she smelled so sweet, I gave her ten or twenty dollars and she gave me her panties after she dug them deep into her pussy and got them soaked. When she was sitting next to me in my car with her panties in my hand, I used my other hand to stroke and finger her pussy real gentle. She had the softest, slickest, finest pussy I have ever touched before or since. That's like 30 years and three wives ago.
This girl was freaking HOT!
Reluctantly I let her go and did take her phone number but never called her or saw her again.
Another time I picked up a girl who was a Black trannie. I got her to give me her panties for around ten dollars and another twenty five to suck my dick.
Before getting the blowjob, we parked up this street that she pointed out. She was reaching over to open my pants when I changed my mind. I made her get up on the seat facing away from me and lifted her dress. She had already took her panties off cause I bought them so her bare ass was right there in front of me.
I rubbed her cheeks and she jiggled her ass and said she liked it in her "pussy". I was very turned on and wanted to kiss her dark brown hole but was too afraid of STDs and settled for a little fingering. It was making my dick throb having my finger deep in this hot fucking nasty asshole.
Suddenly there was flashes in the rearview mirror. A unmarked police car had either pulled up behind me or was there at the curb all along and I never noticed.
Now I was shitting my pants.
I had a new job and a nice conservative wife at home with my two little kids and I figured I was busted in a police sting or something. I didn't know what to do or say but knew I was in deep shit.
So the detectives got out and approached from behind on both sides. The one on my side says some shit like good evening sir can I see your license and registration and insurance card please.
The cop on the other side of the car is just looking around and the whore is smiling at him and telling the cop with my papers how I was just dropping her off and she lives up the block.
He looks at me, hands back my stuff and tells her she can leave then. She gets out and he tells me to go home and stop driving around the park checking out the whores.
I was so relieved I don't even remember the ride home.
I got home and vowed not to cruise the park on my way home again. I did have those panties under the bucket seat of my car and I used them to stroke off when I put the car in the garage.
- That's Juicy! 11
- Remove It! 4
