Streetwalker Reports

**Red1910** · 10-23-19 11:59

Originally Posted by KnightRider82 [View Original Post]

Hi Red, saw her on September 25 around 1:30 pm. At Kilpatrick and 5th. Looked healthy. Good memories. Sucks.

It hard and fast then wants to fuck you with that pussy and is available for anal. And will party too. I remember taking her to motel and she was open to filming porn for extra $. Never seen her though by grand Pulaski. She asked for my number but never calls me. If I see her again I'll get her number for you. If you like Polish another girl is Cindy by Belmont and Cicero. She's petite brunette and is open minded. By the way that picture you posted is her.

Thank you for the information, last night around 1 Am I pick up Cindy 40 $ and really she do her job very good and after dropped Her I saw Sylvia walking by the area Belmont and Cicero and when I was ready to go for He, she got in another car of course my bad luck, really I want a date with Sylvia because she love anal sex (For a little more money) and I love how she screams when we have sex wow I miss Her.

**KnightRider82** · 10-21-19 14:29

Originally Posted by Currymonster [View Original Post]

I picked her up Weds night, she was walking back to 5th from Cicero, fucked her ass and came on her boobs while she licked my balls. I rate her pretty good too, prefer women with some experience really (she's 43). Earlier in the evening I picked up a very skinny WSW called Gia, I believe. Young, 23 she said. Claimed to be an anal virgin, but was willing to let me lube her up and go for it. All covered. Had been basically expecting her to back out of the deal once she'd got the cash, but she was patient and did well. Also said it was OK, and she'd expected it to hurt a whole lot more than it actually did.

I went back for more Friday, slim pickings to begin with, then on another pass I saw Jennifer again, and also a dark haired tall girl who looked really good, so told Jennifer I wanted some variety. This one told me she was Kayeloi, had some baby damage but looked good naked. Blew me well with some BLS and rimming and shot in her mouth. I think I'd try to negotiate good GFE from her next time, she was playing with herself during, so good chance she might actually still be able to get off.

Pretty good success rate. Haven't been to Chicago for 5 years, look forward to returning. Doubtless all the numbers I got from them will have expired by then. As to whether I'll stay at the Shamrock again. Not sure about that.

How much did she charge you for anal? And can you describe her a bit more? It's slim pickings here on Chicago for WSW that do anal. Thanks fellow Monger.

**Currymonster** · 10-21-19 06:34

Originally Posted by Red1910 [View Original Post]

I find Jennifer a definite 8 or 9 in my book BBBJCIM for 30

I picked her up Weds night, she was walking back to 5th from Cicero, fucked her ass and came on her boobs while she licked my balls. I rate her pretty good too, prefer women with some experience really (she's 43). Earlier in the evening I picked up a very skinny WSW called Gia, I believe. Young, 23 she said. Claimed to be an anal virgin, but was willing to let me lube her up and go for it. All covered. Had been basically expecting her to back out of the deal once she'd got the cash, but she was patient and did well. Also said it was OK, and she'd expected it to hurt a whole lot more than it actually did.

I went back for more Friday, slim pickings to begin with, then on another pass I saw Jennifer again, and also a dark haired tall girl who looked really good, so told Jennifer I wanted some variety. This one told me she was Kayeloi, had some baby damage but looked good naked. Blew me well with some BLS and rimming and shot in her mouth. I think I'd try to negotiate good GFE from her next time, she was playing with herself during, so good chance she might actually still be able to get off.

Pretty good success rate. Haven't been to Chicago for 5 years, look forward to returning. Doubtless all the numbers I got from them will have expired by then. As to whether I'll stay at the Shamrock again. Not sure about that.

**Nookie88** · 10-20-19 10:59

Had a dream yesterday afternoon that I dropped a family member off at Midway and did a little stroll up and down Cicero up to McDonalds and turned back around just once. Saw 2 ladies standing near Popeye's and the one that I asked to get in was Kara. Gorgeous brunette (mid 30's) that offered BBBJCIM for 0.4. Went back to MW and parked in garage area ($2 for 30 minutes. LOL). Absolutely stunning lady with a great no rush personality and great hygiene. Gave me her digits and made future plans to bring her to a local Swingers club on Halloween weekend. Worth repeating no doubt.

**Kreezy03** · 10-19-19 21:37

Also Around 2 am this morning (10/19/2019) a sexy ass WSW (atleast her legs / body looked sexy I couldn't see her face) on Cicero and armitage in a coat and little shorts was in the middle of Cicero flagging LEO down (think she called them, they had their lights flashing when coming to her). She talked to them for a bit and was pointing down Cicero. Idk what was going on but when I was coming back down Cicero from division she was getting into a car on armitage. Guess she wasn't a decoy but it was strange. Maybe somebody assaulted her or something who knows. Cars were in the way so I couldn't get a pic.

It was funny tho, as the light turned green at armitage I seen Shorty was running from the area, but she runs so funny, and she was also still watching traffic as she was doing it lmfao.

**Kreezy03** · 10-19-19 21:25

I've gotten with a few SW's over the last couple weeks.

Sheryl (Cheryl?) on 5th a couple weeks ago. 20 for BJ (ALL BJs I get are covered). Head was great. It was late and dark but Idk, her teeth looked surprisingly good LOL that stuck out to me. Wish I got a # on her. She almost left her bag in my car rushing to go get her fix after though.

Shorty on Cicero and grand week before last (Wednesday or Thursday, I forget). 40 for head and sex. Head was unbelievably trash. Idk WTF she was doing but her head sucked. She wasn't rushing or anything and is a cool little chick and funny but damn her head sucks. Went to fuck, cause that ass is amazing, but—and maybe it was just the lighting—but it LOOKED like some red stuff was coming out her pussy. Period? She seems older so I doubt that. Idk. Decided not to fuck. But her ass is big and soft. She sucked and gave me a handjob to completion for the next 15 or so minutes. I'm going to try her again one day. I got her # and see her all the damn time anyway.

T (Tee?) on Cicero before diversey by one of the car lots last Sunday. She's about 5'5-5'6, slim, blonde. Pretty cute. 30 for BJ, gave her 25 cause a 5 is the smallest Bill I had. I had yet to be with a blonde SW and wanted one (that's why I got with Sheryl, but I think her hair is brown or black). She was with a way taller Blonde SW whose pretty cute to, but I chose Tee because the taller one just blew me off one of the last hot nights of the summer a few weeks ago when she was with a HSW (who she's usually with) so fuck her and the HSW LOL. Tee's head was good but I just couldn't keep it up smh (been getting a good amount of free pussy aside from paying for it lately and where I work keeps me dehydrated LOL). But I finally came. She seemed disappointed and thought it was a problem with her skills which was funny to me. Next I'll probably get the taller blonde next and fuck the hell out of her for blowing me off. She still eagerly watches me the last couple times I drive past her. I got tints so maybe she don't even know it's me but we'll find out.

**Red1910** · 10-18-19 22:25

Last night went for a stroll on fifth and kostner, I bumped into Amanda great CBJ 20 then I saw to Sylvia Polish but uncle was around so I had to leave the area and come back today early on the morning about 7 and again I saw Sylvia THE Polish woman but she was out of her mind and looked pretty bad on her face (DRUGS) but someone else got Her in his car before me few minutes later I find Jennifer a definite 8 or 9 in my book BBBJCIM for 30 and no uncle early on the morning.

**Ump1969** · 10-17-19 23:21

Picked up Ashley on Pulaski near Grand. 5-2, brown hair, thin, mostly clean. Guys, it was a beautiful experience. Asked for GFE. She went way above. Kissing, touching, hugging. It could have been a wedding night. I only regret it was in the car. No digits. Looks would be 8. Service would be 12. Dropped her off near 6 points. Damage was $60. Random thoughts on a few recent comments. Sorry to hear threat to a monger. Newbies are always advised to read comments and the rules of the road before taking to the street. George, have been out here for 35 years. Did nit stress it; most readers don't give a damn about the reminiscing of old farts and times change. Otherwise agree with you.

**KnightRider82** · 10-15-19 00:29

Originally Posted by Onit2018 [View Original Post]

So I'm a couple years deep into this so I've learned my lessons. Don't leave anything valuable in arms reach, don't let SW go use the bathroom with money in tow, etc. So the other night I go to grab cash with a date in my car, I take all my valuables with me. Wallet, phone, car key. I think I'm all good. I come back to see her rummaging through my shit under the guise of having dropped something. Whatever, I just want to get one off and what could she have possibly gotten to, I kept everything worth anything with me. We do the deed, I go home and take my stuff up stairs only to see I was short half a bag of green grapes. Jesus Christ.

Has anyone had anything stranger taken off of them?

Been picking them up since early 90's. They will go through your glove compartment under your car seat. They will suck your dick and find that wallet. Then they get a call from pimp and get coached. They are after your cash or anything they can pawn or sell immediately. They will go after your phone. I learned through the years they are very well coached. LEO has been calm for 2 days around 5th / Kostner. Grand Pulaski was dead around 8 pm last night.

**StanleyStankas** · 10-14-19 10:28

Originally Posted by Onit2018 [View Original Post]

So I'm a couple years deep into this so I've learned my lessons. Don't leave anything valuable in arms reach, don't let SW go use the bathroom with money in tow, etc. So the other night I go to grab cash with a date in my car, I take all my valuables with me. Wallet, phone, car key. I think I'm all good. I come back to see her rummaging through my shit under the guise of having dropped something. Whatever, I just want to get one off and what could she have possibly gotten to, I kept everything worth anything with me. We do the deed, I go home and take my stuff up stairs only to see I was short half a bag of green grapes. Jesus Christ.

Has anyone had anything stranger taken off of them?

Nothing strange in my story except the reason she wanted me to turn off the ignition. Gave her some cash and she saw that stupidly I put the remainder of my money in my right coat pocket (I know I probably made more of my share of huge SW mistakes prior to this site, the internet and all kinds of new fan-geld inventions!) Anyway she was giving mouth resuscitation to the little guy and during the deed said "turn off the ignition". When I asked why, as it was winter and my heater was blasting, she said and I remember this statement 40 plus years after the fact "because it's more romantic". Of course being my dumb a** self I obliged and yep when I got back to my crib I was 40 or so short! Oh well. The funny thing about your story is if she said she was hungry you may have even bought her a take along burger after the deed, however no they will always default to wh*res!

**Onit2018** · 10-14-19 07:42

So I'm a couple years deep into this so I've learned my lessons. Don't leave anything valuable in arms reach, don't let SW go use the bathroom with money in tow, etc. So the other night I go to grab cash with a date in my car, I take all my valuables with me. Wallet, phone, car key. I think I'm all good. I come back to see her rummaging through my shit under the guise of having dropped something. Whatever, I just want to get one off and what could she have possibly gotten to, I kept everything worth anything with me. We do the deed, I go home and take my stuff up stairs only to see I was short half a bag of green grapes. Jesus Christ.

Has anyone had anything stranger taken off of them?

**KnightRider82** · 10-14-19 04:59

Hi Red, saw her on September 25 around 1:30 pm. At Kilpatrick and 5th. Looked healthy. Good memories. Sucks.

It hard and fast then wants to fuck you with that pussy and is available for anal. And will party too. I remember taking her to motel and she was open to filming porn for extra $. Never seen her though by grand Pulaski. She asked for my number but never calls me. If I see her again I'll get her number for you. If you like Polish another girl is Cindy by Belmont and Cicero. She's petite brunette and is open minded. By the way that picture you posted is her.

**George Stark** · 10-13-19 23:47

Originally Posted by Ump1969 [View Original Post]

Years ago, LEO didn't care as much as there were many crimes more serious and cops didn't want to be wasting time on prostitution paperwork when there was more serious crime on the streets. Now it seems like prostitution is more serious than murder.

THIS! They ought to just subtly hint to the girls to use deserted stretches of road, where there's no citizens to complain, and then the cops could get back to real work. Because God knows in this city there is plenty of it.

I agree with you on the quality of the girls decreasing from when I mongered, but that was way farther back than 10 years ago. I could have been street-mongering 10 years ago, oh well.

I just shake my head at some of the pics posted here. I won't say I've never picked up an unattractive girl, but it was so much better a verrrry looong time ago. I'm sure people are tired of my old-man reminiscing about it by now.

**Red1910** · 10-13-19 12:40

Originally Posted by KnightRider82 [View Original Post]

Drove 5th yesterday dead. Only saw a couple BSW. Saw 1 looked good from a distance just asked how much said $20 for sloppy head. I said I'm OK. She was salivating from mouth. Look like the Walking dead shit. Drove to Kostner picked up Julie good girl. Drove down kilpatrick detectives on scene by Jackson looked like a murder. Then drove to Pulaski saw BSW pregnant decided to skip not my thing. By grand and Pulaski saw Hispanic street walker reading while hooking on corner. Hopefully pics from adventure will post. Also Bumped into Sylvia Polish on 5th she's looking good one of the best head. Sucked me off and was willing for anal. Police is everywhere. Be careful fellow mongers.

Knight rider.

I have 3 weeks looking for Sylvia last time I saw Her was by pulaski anda grand ave (this is the girl that you saw by 5th ave?) If is the same girl around at what time I could find Her.

Or you know If she has number phone!

Thank you.

**Ump1969** · 10-13-19 00:27

Originally Posted by GeorgeStark [View Original Post]

Why are the pickings so slim here? It's not the Internet. That's everywhere, other cities have jumping street scenes. It can't be the weather, entirely, it's good weather here some of the year.

I have heard people talking about much smaller cities being livelier.

I know it didn't used to be this way.

I understand what happened to all the great clubs, the Feds shut those down when they went after organized crime, who was paying off the towns those clubs were in.

But there's nothing organized about streetwalkers, so just WTF?

I was talking with a fellow monger about how it would be cool to have a cargo van fitted out for street-mongering. But after some discussion, I decided that it's not even worth it here.

Is it Dart? I didn't think he did that much on the Chicago streets, except the occasional sting of johns. Maybe.

So: WTF?.

Hi, George. Read many of your comments. There is no one answer. I don't go as often as I used to because the quality of girls and the quality of service is way down. Back ten years or more, I knew girls that were pretty good looking and often made you feel like proposing to them. Now many look years older than they really are, are missing teeth, and just want to get out of the car ASAP to find their next hit. Years ago, LEO didn't care as much as there were many crimes more serious and cops didn't want to be wasting time on prostitution paperwork when there was more serious crime on the streets. Now it seems like prostitution is more serious than murder. When areas, get shut down, the girls are crowded into less areas and it becomes easier for LEO to patrol. Girls use to have a steady stream of customers and made a lot of money. Now many are on public assistance and use street money for drugs. One customer per night and they are off to get high and crash. Or just enough to pay rent for a spot on someone's floor for the night. The laws are tougher fir getting caught. Girls end up doing time downstate. I probably forgot a few. The atmosphere is just different. Of, I forgot the Internet. Girls that used to get $20 for a BJ now think they are worth $100 or more because they list online and might actually have an indoor spot.