Here you go Mitch44 my first adventure with a Street Walker named Dawn.
Dawn First Meeting On The Street
I had been working to set up the new computer system that my company needed and we were finally done. I was feeling pretty good. It had been three days of intense inputting. There were questions in my mind if I had made the right decision on installing this system. The more I worked on it the more I questioned what did I do? I was past the point of no returned. I just knew I needed to get my mind off it, now that it was set and running. My IT guys were now in charge and I needed to step back. How best to get my mind off it but to go and find a ‘’girlfriend for an hour or two. I was on my way to meet with the property developers in Toronto. Although one project was completed, another needed my attention. It was never ending. So, I head down to Toronto, to clear my head.
I drove around the high track, mindless and there on the corner was a hot raven-haired beauty with big tits and gorgeous full hair in a flower dress, black stockings, and black heals. As I got closer, she had smoky eyes and a very attractive face. Part of me said no, but another part of me said, just pull over and say hello. I drove around one more time and she knew I was scouting her out. I pulled over she walked to my passenger window. I used the power button to lower the window. She bent over so I could see her incredible blue eyes, big breasts under the black flower wrap dress that I would
swear was more like a silk house coat than full out dress. She appeared to be wearing a push up bra covering her 34DDs that she wanted the world to see and she was proud to presented the ‘girls’ to me. I could picture her saying “do you like my big tits?” However, her first words to me, “Are you looking for some company?” Her second words, “are you a cop?” I told her “yes” then “no,” she went on to asked me to show her my dick.
I liked her tone and her look, so I unzipped and presented my dick, who was very pleased to meet her as it stood at attention like a solder on parade.
She opened my passenger door, slid in and reached over to my side of the car. Then looking out the window, she touched my hard dick.
“Am I ok?” I asked.
“I can see that.” She replied. “You are more than ok with a dick like that.”
I didn’t move. Her hand fondled me a little, I just turned my head and looked at her, telling her she was beautiful. “I bet you tell all the girls that.” Was her reply in a nonchalant way.
Her boobs were clearly in reach, as I noticed her chest heave. She was gorgeous and they were even more gorgeous in the flash of lights on the street. I wanted to touch them.
I swiveled in my seat, with pictures of her dancing naked in my mind I looked at her boobs. I lifted my head to see if her dress had opened far enough for me to get a look at her chest. She saw that I was looking at her big tits as they nearly fell out of her wrap dress was pretty close to exposing her nipples for me. A closer look and I could see they were well covered in a dark silk bra.
“Well good looking, do you have $100?” I said yes, and she said, “then let’s go”. As I drove off, she asked if I had a hotel or if we could use her hotel room. She told me her place was not very good so we agreed to head over to my hotel.
As I drove off, she reached over to ask me again if I was a cop. I told her no and she reached between my legs then told me I was good looking and my cock felt huge. She told me I was so thick and hoped the condom would fit. As she spoke, she lifted the hem of her dress. I could see the dark silk panty in the shadow of the street light. There wasn’t much, I could see as she commented, that she had shaved not too long ago. Her silk panties glistened in the lights that covered her kitten. Yet the thought of her shaven pussy intrigued me.
I shifted a bit in my seat to giving her better access to fondling my dick. She stroked it. she unbuttoned my pants. She unzipped them. She reached into my pants and pulled my hard stick all the way out, freeing it. She hummed getting closer. “Mmmmm.” “Is that better.”
She went on to say. “Oh, I think I am going to enjoy you.” “Have you ever considered porn.” I laughed wondering if she told all her clients that. It really did not matter. I was enjoying her stroking me. “Fuck you are huge.” She exclaimed as we came to a light. She looked around and bent over to put her mouth to the head of my dick, licking me until the light turned green.
“Fuck I hope I can fit you in me?” She questioned.
I reached out and took one of her boobs in my hand. SHIT! They were real. By time she had my pants fully unzipped we were pulling into the hotel parking lot. I parked and her mouth enveloped my dick as I fondled her boobs. I parked in a dark spot at the back as far away from a street light as I could. I parted my legs while she swallowed my dick down to the base. She fondled my butt and tried to pull me out of my seat to get at my butt.
“Fuck lets go. I want to fuck you!” I told her I did not want to blow my load in the parking lot. I opened my door. I got out of the car pulled up my pants as she did up her dress and we got our selves together and raced into the hotel. We passed the registration desk right into the elevator. I handed her the $100 and she stashed it into her purse then kissed me. Then whispered for $200 she could stay for two hours. As we hit my floor and exited, I pulled out a second hundred giving it to her. She told me she normally does not kiss, but she like me. We found my suite. We got in and I turned on the lights. As I turned around, she had undone her dress and looked at me with a very seductive look on her face. She reached for my dick in my pants.
“Take that off,” I said to her.
She was obedient. She stood before me and let her silky dress slip from her shoulder down her legs to the floor. It floated to the floor like a feather. She stood before me in a blue bra and panty set with a black garter belt that did not go with the bra or panty but who was complaining.
She pulled my pants down. She came closer and I reached out and fondled her pussy under the blue G-string. Before I could get my face close to hers, she shoved me back on the couch. My pants did not allow me to catch my fall. She knelt before me and she went to work on my man meat.
She gobbled me up slurping and swallowing me whole. She sucked my head the licked and stroked me dick. She spat on me then using her hands she stroked me. She looked up to ask me what was my favorite color. I was confused and said blue. She pulled her purse over and pulled out a condom.
“Sorry no extra-large blue condoms. You will have to use clear.”
My head buried in her soft mounds. God those nipples were great to suck on and no matter how hard I sucked the more it turned her on. I bit them and bit them so hard I left red marks. She was coming to a climax and I put the nipples together and sucked on both of them at the same time.
Her hips bucked and rocked at me as she came. She oozed and fluid ran down her long legs absorbed by her stockings. I stood up and while taking off my shirt, and went into my bathroom and got a towel. I laid it on the carpet and she laid down on it then she started fingering herself.
Naked, I laid down with a knee in between her legs. I rubbed her clit with my hardening cock, she came again. I rubbed more, she came more. I played with her clit with my fingers while sucking on those tits and rubbing the boobs. She came more. Her back arched, my dick ached. The towel was getting wet. I stuck my finger up in her, then two. It didn’t faze her. Three, at four she was “oohing”. I pushed more and my thumb found her butt hole. She leaked so much it was so wet my thumb was covered. It went into her butt as easily as my finger in her pussy. I reached in further and further until my finger tickled her cervix. My thumb and finger rubbed between the walls and she began to buck in rolling climaxes.
I sucked on her nipples so hard they were turning purple.
Finally, she pulled me onto her, “fuck me,” she said. “Come on, put that dick in me.”
I moved into position and she final put on the clear rubber and I slipped into her right to the hilt. She was loose, but it was a good fuck. I rammed her with all I was worth. I rode up on her clit with my dick and she came more but I wasn’t getting a good tight fit. I pushed in and came out. Went in and came out, over and over, giving her the sensation of my dick pumping into her.
Then on one of the times I pulled out I dropped my body just a bit. It hit in between her cunt and butt hole. She squealed, with delight as it turned out she liked the sensation. I pumped the space in between, pushing on it and then on the fourth push my dick landed on her butt hole. I pushed, hard, harder, and in it went in her tight hole.
She squealed and I covered her mouth with the hand I had in her pussy. She bit my fingers and sucked them into her mouth. We switched it up and she flipped over as I pulled her legs up and out to the side giving me more access to her butt. Pounded her pushing harder and harder. My excitement grew as she came to more climaxes.
Finally, I blew my load into her butt slamming my dick up into her. Damn it was a great, far better than other street walkers I had seen. She was good and took anything I did to her.
After a few minutes I pulled out and walked into the bathroom and took a quick shower washing my dick off triple clean. Then washed it again to make sure. When I came out, she was still on the floor. She motioned to me to come over and stand over her. She took hold of my thighs and pulled herself up to a sitting position. She took my soft dick in her mouth and swallowed the entire thing.
It began to grow in her mouth. She held it and wouldn’t let it go. The harder it got the more she held onto it. I looked at her worshipping my dick. Her eyes were so striking and she was so beautiful in that moment. I will never for get it.
“Push” she said as my dick got fully hard. She took my hands and put them on the back of her head.
I pushed. “Fuck,” she said as best as she could with my dick in her mouth.
I pushed and fucked her face. It was getting better and better. I got harder, and the more I pushed the more she got excited. She wheezed gasping for breath as I shoved my dick into the lady’s mouth harder and harder.
“More” she mouthed. I pushed harder until I was about to cum, I paused.
“No, no, not yet,” she demanded. As I laid on my back totally l at her mercy she put on another condom and got on top of me. She rode me like a mad woman. Her tits bouncing frankly. Up down then up and down. I was in a trance. She stopped then moved her pussy back and forth with her hands on my thighs. Her gyrations on my love stick were replaced with the frantic up and down motion. My hips now joined in her pounding.
I pushed for all I was worth as I came for a second time. She moved around as I tried to gain some sense of reality then in a reverse cowgirl, she went at it again pouncing on my dick. She started to scream, “fuck me, fuck me with your monster cock, fill me up.” Her ass moving up and down over my thickness it was a sight to see her working my dick with her ass cheeks. I was going fucking crazy. I grabbed her ass and squeezed it. My thumb now embedded in her asshole. This caused her to scream louder as she kept bouncing until she erupted again. She fell forward in after catching her breath she pulled her pussy off my now softening cock leaving the condom still in her pussy leaking profusely. My seed flowed freely from the condom in her pussy. She pulled it out placing it on the night stand.
She went to work sucking and cleaning my cock. I don’t think a drop got in her mouth as it went straight down her throat. She sucked on my dick for all I was worth. It hurt so damn bad I thought she was going to eat and swallow the fucking thing.
Soft, I was finally able to get it away from her. She laid back down on the towel and fingered herself to a half dozen more climaxes in front of me.
“Do that again sometime, maybe tomorrow?” she asked and I agreed as I came out of the bathroom washing my sore dick thinking about her offer. I might just have to try this again.
Dawn First Meeting On The Street
I had been working to set up the new computer system that my company needed and we were finally done. I was feeling pretty good. It had been three days of intense inputting. There were questions in my mind if I had made the right decision on installing this system. The more I worked on it the more I questioned what did I do? I was past the point of no returned. I just knew I needed to get my mind off it, now that it was set and running. My IT guys were now in charge and I needed to step back. How best to get my mind off it but to go and find a ‘’girlfriend for an hour or two. I was on my way to meet with the property developers in Toronto. Although one project was completed, another needed my attention. It was never ending. So, I head down to Toronto, to clear my head.
I drove around the high track, mindless and there on the corner was a hot raven-haired beauty with big tits and gorgeous full hair in a flower dress, black stockings, and black heals. As I got closer, she had smoky eyes and a very attractive face. Part of me said no, but another part of me said, just pull over and say hello. I drove around one more time and she knew I was scouting her out. I pulled over she walked to my passenger window. I used the power button to lower the window. She bent over so I could see her incredible blue eyes, big breasts under the black flower wrap dress that I would

I liked her tone and her look, so I unzipped and presented my dick, who was very pleased to meet her as it stood at attention like a solder on parade.
She opened my passenger door, slid in and reached over to my side of the car. Then looking out the window, she touched my hard dick.
“Am I ok?” I asked.
“I can see that.” She replied. “You are more than ok with a dick like that.”
I didn’t move. Her hand fondled me a little, I just turned my head and looked at her, telling her she was beautiful. “I bet you tell all the girls that.” Was her reply in a nonchalant way.
Her boobs were clearly in reach, as I noticed her chest heave. She was gorgeous and they were even more gorgeous in the flash of lights on the street. I wanted to touch them.
I swiveled in my seat, with pictures of her dancing naked in my mind I looked at her boobs. I lifted my head to see if her dress had opened far enough for me to get a look at her chest. She saw that I was looking at her big tits as they nearly fell out of her wrap dress was pretty close to exposing her nipples for me. A closer look and I could see they were well covered in a dark silk bra.
“Well good looking, do you have $100?” I said yes, and she said, “then let’s go”. As I drove off, she asked if I had a hotel or if we could use her hotel room. She told me her place was not very good so we agreed to head over to my hotel.
As I drove off, she reached over to ask me again if I was a cop. I told her no and she reached between my legs then told me I was good looking and my cock felt huge. She told me I was so thick and hoped the condom would fit. As she spoke, she lifted the hem of her dress. I could see the dark silk panty in the shadow of the street light. There wasn’t much, I could see as she commented, that she had shaved not too long ago. Her silk panties glistened in the lights that covered her kitten. Yet the thought of her shaven pussy intrigued me.
I shifted a bit in my seat to giving her better access to fondling my dick. She stroked it. she unbuttoned my pants. She unzipped them. She reached into my pants and pulled my hard stick all the way out, freeing it. She hummed getting closer. “Mmmmm.” “Is that better.”
She went on to say. “Oh, I think I am going to enjoy you.” “Have you ever considered porn.” I laughed wondering if she told all her clients that. It really did not matter. I was enjoying her stroking me. “Fuck you are huge.” She exclaimed as we came to a light. She looked around and bent over to put her mouth to the head of my dick, licking me until the light turned green.
“Fuck I hope I can fit you in me?” She questioned.
I reached out and took one of her boobs in my hand. SHIT! They were real. By time she had my pants fully unzipped we were pulling into the hotel parking lot. I parked and her mouth enveloped my dick as I fondled her boobs. I parked in a dark spot at the back as far away from a street light as I could. I parted my legs while she swallowed my dick down to the base. She fondled my butt and tried to pull me out of my seat to get at my butt.
“Fuck lets go. I want to fuck you!” I told her I did not want to blow my load in the parking lot. I opened my door. I got out of the car pulled up my pants as she did up her dress and we got our selves together and raced into the hotel. We passed the registration desk right into the elevator. I handed her the $100 and she stashed it into her purse then kissed me. Then whispered for $200 she could stay for two hours. As we hit my floor and exited, I pulled out a second hundred giving it to her. She told me she normally does not kiss, but she like me. We found my suite. We got in and I turned on the lights. As I turned around, she had undone her dress and looked at me with a very seductive look on her face. She reached for my dick in my pants.
“Take that off,” I said to her.

She was obedient. She stood before me and let her silky dress slip from her shoulder down her legs to the floor. It floated to the floor like a feather. She stood before me in a blue bra and panty set with a black garter belt that did not go with the bra or panty but who was complaining.
She pulled my pants down. She came closer and I reached out and fondled her pussy under the blue G-string. Before I could get my face close to hers, she shoved me back on the couch. My pants did not allow me to catch my fall. She knelt before me and she went to work on my man meat.

“Sorry no extra-large blue condoms. You will have to use clear.”
My head buried in her soft mounds. God those nipples were great to suck on and no matter how hard I sucked the more it turned her on. I bit them and bit them so hard I left red marks. She was coming to a climax and I put the nipples together and sucked on both of them at the same time.
Her hips bucked and rocked at me as she came. She oozed and fluid ran down her long legs absorbed by her stockings. I stood up and while taking off my shirt, and went into my bathroom and got a towel. I laid it on the carpet and she laid down on it then she started fingering herself.
Naked, I laid down with a knee in between her legs. I rubbed her clit with my hardening cock, she came again. I rubbed more, she came more. I played with her clit with my fingers while sucking on those tits and rubbing the boobs. She came more. Her back arched, my dick ached. The towel was getting wet. I stuck my finger up in her, then two. It didn’t faze her. Three, at four she was “oohing”. I pushed more and my thumb found her butt hole. She leaked so much it was so wet my thumb was covered. It went into her butt as easily as my finger in her pussy. I reached in further and further until my finger tickled her cervix. My thumb and finger rubbed between the walls and she began to buck in rolling climaxes.
I sucked on her nipples so hard they were turning purple.

I moved into position and she final put on the clear rubber and I slipped into her right to the hilt. She was loose, but it was a good fuck. I rammed her with all I was worth. I rode up on her clit with my dick and she came more but I wasn’t getting a good tight fit. I pushed in and came out. Went in and came out, over and over, giving her the sensation of my dick pumping into her.
Then on one of the times I pulled out I dropped my body just a bit. It hit in between her cunt and butt hole. She squealed, with delight as it turned out she liked the sensation. I pumped the space in between, pushing on it and then on the fourth push my dick landed on her butt hole. I pushed, hard, harder, and in it went in her tight hole.
She squealed and I covered her mouth with the hand I had in her pussy. She bit my fingers and sucked them into her mouth. We switched it up and she flipped over as I pulled her legs up and out to the side giving me more access to her butt. Pounded her pushing harder and harder. My excitement grew as she came to more climaxes.
Finally, I blew my load into her butt slamming my dick up into her. Damn it was a great, far better than other street walkers I had seen. She was good and took anything I did to her.
After a few minutes I pulled out and walked into the bathroom and took a quick shower washing my dick off triple clean. Then washed it again to make sure. When I came out, she was still on the floor. She motioned to me to come over and stand over her. She took hold of my thighs and pulled herself up to a sitting position. She took my soft dick in her mouth and swallowed the entire thing.

“Push” she said as my dick got fully hard. She took my hands and put them on the back of her head.
I pushed. “Fuck,” she said as best as she could with my dick in her mouth.
I pushed and fucked her face. It was getting better and better. I got harder, and the more I pushed the more she got excited. She wheezed gasping for breath as I shoved my dick into the lady’s mouth harder and harder.
“More” she mouthed. I pushed harder until I was about to cum, I paused.


She went to work sucking and cleaning my cock. I don’t think a drop got in her mouth as it went straight down her throat. She sucked on my dick for all I was worth. It hurt so damn bad I thought she was going to eat and swallow the fucking thing.
Soft, I was finally able to get it away from her. She laid back down on the towel and fingered herself to a half dozen more climaxes in front of me.
“Do that again sometime, maybe tomorrow?” she asked and I agreed as I came out of the bathroom washing my sore dick thinking about her offer. I might just have to try this again.