Streetwalker Reports

[Ron M]

This was a new one. I was driving around over the weekend running some errands when I got off the highway at Diversey. As I was exiting I saw a girl holding a sign asking for money. I looked a little closer and she was unusually pretty for a seemingly homeless girl. Probably about 5'6", mid 20's, maybe like 130, white, brown hair. She definitely wasn't dressed like a SW, and wasn't wearing makeup, but she wasn't in rags either. She looked like the kind of girl who would be at your average dive bar in Logan Square.

I stopped at the light, rolled down the window and make some small talk. I debated what I should give her because I don't really give money to beggars. She sounded more like a hard luck case who hit a tough patch during the pandemic than a "bum".

Now I've never been someone to do the SW thing, but I couldn't understand why a girl that good looking was asking for pocket change. I thought I would give it a shot and see what happens, so I offered instead of just giving her money to get her a room instead. She agreed and hopped in the car. I was worried she would smell terrible but she was fine.

Long story short, I got her a room, gave her $20 for any meals she would need for the day and after feeling things out for a while in the room with her I ended up fucking her. She's definitely not a pro, or at least she didn't act or fuck like that. Mainly she took a shower, came out, sat on the bed with me, then we started making out while I undressed, then she started rubbing my cock while I fingered her and then she pulled my cock into her pussy and I fucked her mish. No oral or porn star stuff. It was like a regular random hookup from Tinder or whatever.

Between the hotel and the money, I probably spent about $100 and stayed for a good hour and a half and fucked her twice (probably should have asked about birth control at some point but we were in the heat of things). Maybe it was more than some of what you guys pay for a SW, but for a nice leisurely GFE with a girl in her 20's it was a pretty good deal.

Is this a known thing you guys run into sometimes? Or did I really luck out?

To me it looks like she was really working. She probably knew as good looking as she is she knew some guys were going proposition her. She was just using a sign saying she was homeless needing help to throw off the police and neighborhood people.

[Jinurso]

Just curious, where did you get the room?

Also, did you let her stay in the room after you left? I wouldn't do that if the room was in my name. She sounds ok, but who really knows?

Random hotel on Lincoln where some girls who work in Chicago like to frequent. Figured they would be cheap.

And quick with no questions asked. I got it in her name and I paid for it in cash.

[George Stark]

Long story short, I got her a room,

Just curious, where did you get the room?

Also, did you let her stay in the room after you left? I wouldn't do that if the room was in my name. She sounds ok, but who really knows?

[OnlyDreams]

This was a new one. I was driving around over the weekend running some errands when I got off the highway at Diversey. As I was exiting I saw a girl holding a sign asking for money. I looked a little closer and she was unusually pretty for a seemingly homeless girl. Probably about 5'6", mid 20's, maybe like 130, white, brown hair. She definitely wasn't dressed like a SW, and wasn't wearing makeup, but she wasn't in rags either. She looked like the kind of girl who would be at your average dive bar in Logan Square.

I stopped at the light, rolled down the window and make some small talk. I debated what I should give her because I don't really give money to beggars. She sounded more like a hard luck case who hit a tough patch during the pandemic than a "bum".

Now I've never been someone to do the SW thing, but I couldn't understand why a girl that good looking was asking for pocket change. I thought I would give it a shot and see what happens, so I offered instead of just giving her money to get her a room instead. She agreed and hopped in the car. I was worried she would smell terrible but she was fine.

I'm glad you had fun with her! I think you were lucky to find a decent looking girl and she accepted your offer. I don't think this type of situation happens frequently. Sometimes they come out with their homeless friends and each pick a corner. Anyway, I've wanted to do something similar. I've also spotted an average looking girl begging for money with at the Addison exit on i90/94 express way several times. But she looks kind of dirty and her hair is a little mess. She doesn't move much from there and if you want to make a small talk with her I'm sure there will be dozens of cars behind honking at you LOL! Long time ago (smart phones didn't exist yet) I met a girl at a Walgreens parking lot, she was carrying a bag and told me she needed a ride home. She was young and didn't look like a homeless girl. She was wearing leggings and I was horny LOL, So thinking with my lower head I gave her a ride home and half way she touched my private parts and told me she can give me head for $40. She didn't want to do FS, but I accepted her deal, I parked by a Home Depot LOL and let her do the deed. At this point I was worried about not getting caught by construction workers and shoppers LOL, I had to finish kind of quickly, She let me unload it in her mouth. I asked for her number but she told me she didn't have a one. Then she asked me to drop her off at some busy intersection. I'm not sure if she was a hooker or just a regular girl, but I had some fun. That was the only time I did something with a random girl I had just met on the street. But your story is way more fascinating. I hope you asked for some kind of contact info to be in touch with her. I would have even purchased her a cheat prepaid phone LOL.

[Jinurso]

Did you not have a rubber on you or could stop at a nearby store to grab one? Did you attempt to make any plans to see her again in the future? Around what time of day was this?

$100 is not bad for everything you did.

I wasn't SURE we were going to have sex and I didn't want to presume and potentially scare her off by buying one before we got the hotel. She wasn't a prostitute so I was careful to avoid treating her like one. And by the time she was out the shower and she was rubbing my dick there was no stopping that train.

This was around 1 pm Saturday. She said she lost her phone and I couldn't take her number. I thought about giving her mine, but was worried about getting random distress calls from now on. Also I had mixed feelings about it all. I never fucked a non-prostitute homeless girl before. She was a really sweet girl and I didn't want to make a habit out of something like that.

[Fdottt]

This was a new one. I was driving around over the weekend running some errands when I got off the highway at Diversey. As I was exiting I saw a girl holding a sign asking for money. I looked a little closer and she was unusually pretty for a seemingly homeless girl. Probably about 5'6", mid 20's, maybe like 130, white, brown hair. She definitely wasn't dressed like a SW, and wasn't wearing makeup, but she wasn't in rags either. She looked like the kind of girl who would be at your average dive bar in Logan Square.

I stopped at the light, rolled down the window and make some small talk. I debated what I should give her because I don't really give money to beggars. She sounded more like a hard luck case who hit a tough patch during the pandemic than a "bum".

Now I've never been someone to do the SW thing, but I couldn't understand why a girl that good looking was asking for pocket change. I thought I would give it a shot and see what happens, so I offered instead of just giving her money to get her a room instead. She agreed and hopped in the car. I was worried she would smell terrible but she was fine.

Long story short, I got her a room, gave her $20 for any meals she would need for the day and after feeling things out for a while in the room with her I ended up fucking her. She's definitely not a pro, or at least she didn't act or fuck like that. Mainly she took a shower, came out, sat on the bed with me, then we started making out while I undressed, then she started rubbing my cock while I fingered her and then she pulled my cock into her pussy and I fucked her mish. No oral or porn star stuff. It was like a regular random hookup from Tinder or whatever.

Between the hotel and the money, I probably spent about $100 and stayed for a good hour and a half and fucked her twice (probably should have asked about birth control at some point but we were in the heat of things). Maybe it was more than some of what you guys pay for a SW, but for a nice leisurely GFE with a girl in her 20's it was a pretty good deal.

Is this a known thing you guys run into sometimes? Or did I really luck out?

Did you not have a rubber on you or could stop at a nearby store to grab one? Did you attempt to make any plans to see her again in the future? Around what time of day was this?

$100 is not bad for everything you did.

[Chiguy007]

This was a new one. I was driving around over the weekend running some errands when I got off the highway at Diversey. As I was exiting I saw a girl holding a sign asking for money. I looked a little closer and she was unusually pretty for a seemingly homeless girl. Probably about 5'6", mid 20's, maybe like 130, white, brown hair. She definitely wasn't dressed like a SW, and wasn't wearing makeup, but she wasn't in rags either. She looked like the kind of girl who would be at your average dive bar in Logan Square.

I stopped at the light, rolled down the window and make some small talk. I debated what I should give her because I don't really give money to beggars. She sounded more like a hard luck case who hit a tough patch during the pandemic than a "bum".

Now I've never been someone to do the SW thing, but I couldn't understand why a girl that good looking was asking for pocket change. I thought I would give it a shot and see what happens, so I offered instead of just giving her money to get her a room instead. She agreed and hopped in the car. I was worried she would smell terrible but she was fine.

Long story short, I got her a room, gave her $20 for any meals she would need for the day and after feeling things out for a while in the room with her I ended up fucking her. She's definitely not a pro, or at least she didn't act or fuck like that. Mainly she took a shower, came out, sat on the bed with me, then we started making out while I undressed, then she started rubbing my cock while I fingered her and then she pulled my cock into her pussy and I fucked her mish. No oral or porn star stuff. It was like a regular random hookup from Tinder or whatever.

Between the hotel and the money, I probably spent about $100 and stayed for a good hour and a half and fucked her twice (probably should have asked about birth control at some point but we were in the heat of things). Maybe it was more than some of what you guys pay for a SW, but for a nice leisurely GFE with a girl in her 20's it was a pretty good deal.

Is this a known thing you guys run into sometimes? Or did I really luck out?

Sounds like you got really lucky.

[Chiguy007]

Lord Dart was doing a dunk shower today in Mount Greenwood for charity. Two thoughts. Wish I had known. I would have been glad to to be charitable. Two, is there any chance of pneumonia?

Pm me what you really mean?

[Jinurso]

This was a new one. I was driving around over the weekend running some errands when I got off the highway at Diversey. As I was exiting I saw a girl holding a sign asking for money. I looked a little closer and she was unusually pretty for a seemingly homeless girl. Probably about 5'6", mid 20's, maybe like 130, white, brown hair. She definitely wasn't dressed like a SW, and wasn't wearing makeup, but she wasn't in rags either. She looked like the kind of girl who would be at your average dive bar in Logan Square.

I stopped at the light, rolled down the window and make some small talk. I debated what I should give her because I don't really give money to beggars. She sounded more like a hard luck case who hit a tough patch during the pandemic than a "bum".

Now I've never been someone to do the SW thing, but I couldn't understand why a girl that good looking was asking for pocket change. I thought I would give it a shot and see what happens, so I offered instead of just giving her money to get her a room instead. She agreed and hopped in the car. I was worried she would smell terrible but she was fine.

Long story short, I got her a room, gave her $20 for any meals she would need for the day and after feeling things out for a while in the room with her I ended up fucking her. She's definitely not a pro, or at least she didn't act or fuck like that. Mainly she took a shower, came out, sat on the bed with me, then we started making out while I undressed, then she started rubbing my cock while I fingered her and then she pulled my cock into her pussy and I fucked her mish. No oral or porn star stuff. It was like a regular random hookup from Tinder or whatever.

Between the hotel and the money, I probably spent about $100 and stayed for a good hour and a half and fucked her twice (probably should have asked about birth control at some point but we were in the heat of things). Maybe it was more than some of what you guys pay for a SW, but for a nice leisurely GFE with a girl in her 20's it was a pretty good deal.

Is this a known thing you guys run into sometimes? Or did I really luck out?

[Davidonecall]

Was driving by Cermak and Washtenaw. Have not been active in the SW but decided to pick up. Gave me the name as Maria and she said. $ for BJ. I said that I only had the 3&5. It was more HJ but for a quick fun. Drop her off and someone else was waiting. Fake blond.

[Ump1969]

Lord Dart was doing a dunk shower today in Mount Greenwood for charity. Two thoughts. Wish I had known. I would have been glad to to be charitable. Two, is there any chance of pneumonia?

[KnightRider82]

Saw this red head WSW today around 3 pm at Congress and Kostner. She had several guys honking at her, decided to pass her up to head to 5th. Saw 2 other HSW never seen before on my way back to Congress saw this red head again. Took a couple pics for the guys. Maybe someone recognizes her? Regarding my last post with the pic, her name is Lala, any one partake with her? Added note, Didn't see much LEO by 5th.

[ManTooth]

I was out in the early afternoon recently on Mannheim just south of the bridge at Lake driving NB. I saw an absolutely delicious looking BSW walking NB on the east side of the street. She was constantly looking back making eye contact with passing drivers. She was wearing an unbelievable pair of purple pants, if I only had more time.

[Ron M]

I sometimes think that one of the best investments a serious hobbyist could make would be to pick up an old conversion van. It would likely pay for itself in a year or two in savings over no-tell room fees.

How about an old RV? Like the old Toyota Chinnok pickup truck with an RV attachment in the pickup bed.

[George Stark]

I sometimes think that one of the best investments a serious hobbyist could make would be to pick up an old conversion van. It would likely pay for itself in a year or two in savings over no-tell room fees.

I actually considered this. Decided it's just not worth it in Chicago, it seems like the SW scene sucks so bad here. I'd love to be proven wrong.

Now in the 70s and 80s that would have been brilliant. I'd have been hunting on North avenue between the river and the Kennedy all day everyday. I wish I'd thought of it then.

Sorry for the senior moment there.