Streetwalker Chronicles - weird true stuff that happened to me with hookers (MF)

[gdukr]

If you're reading this thread for the first time, be advised that the content is intended more for entertainment than arousal. The world of street prostitution is a strange, desperate place and this forum seems like one of the few appropriate places to tell these stories.

[gdukr]

In all the years I picked up hookers I only learned a few of their names and hardly remember any of them now. I feel like they should have names for these stories, though, so I'll use the names of the irritating women who are in my life now. Yes, it's childish, but that's how I roll.

Jill was a cute whore, short with long, curly, black hair and a nice body. She was jerking me off while I played with her tits and eventually I came all over her hand.

"Ew! Ew! Yuck!" she exclaimed with genuine disgust.

I was shocked. "Did they not tell you in hooker school that this was a hazard of the profession?" I laughed.

She shot daggers at me out of her eyes, but I was busy building on my "hooker school" concept and kept going.

"I bet the teacher wore white, plastic, go-go boots."

"That's fucked up, man" she said, pouting.

There were a few intelligent whores with good senses of humor, but Jill wasn't one of them.

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EPILOGUE:

The last time I saw Jill I had just picked her up and we got caught by the cops. I use the word "cops" loosely because they were transit police and while technically policemen they had a clear inferiority complex that manifested itsself in the big deal they made out of pulling me over.

They didn't arrest us but they dumped her purse full of dope paraphernalia into a storm drain and told her my real name. I laid low for a while after that and never saw her again.

[gdukr]

I'd heard that there were some guys going around beating up hookers and their johns but hadn't thought much about it...

I was sitting in my car with a whore who I don't remember, getting ready for a quick handjob. I was parked on a sidewalk in an industrial area late at night when a big pickup pulled up alongside of me and two guys got out. It happened so fast that I hadn't really made sense of the situation when I turned the key and pulled away. All I knew was that there was something wrong and I needed to get out of there.

The guys in the pickup thought they had me trapped but there was a space between their truck and a concrete staircase that I decided was worth a try. All they got for their effort was red paint from my little beater car on their shiny, black truck. Fuck them.

The girl and I found another spot to get the job done.

[gdukr]

Helen was a whore that I only picked up once. She wasn't much to look at, pudgy and not very bright. Still she was in her twenties and I wasn't contemplating marriage.

One of my favorite things to do with hookers was to get a simple hand job while I played with her tits and asked probing questions. How old were you the first time you got fucked, were you ever raped, molested, etc.

Helen had given strange and evasive answers before stating, unprompted, "You can kill me if you want to."

I should have kicked her out then and there but my morbid curiosity made me want to find out how nuts she really was.

"Should I choke you?" I asked.

"No, I've already seen that movie," she answered. Whatever the fuck that meant.

"So how should I do it?" I asked. At this point, not only did I not want to kill her, I didn't want to be in the same enclosed space with her. She was completely insane.

"Oh, I don't know," she said.

In the end I shot my load on her and booted her out. No rides back for wackos.

[cumlovr3014]

Several years ago while I trucked the 48 states, I had the pleasure of finding a hot streetwalker in one of the cities that I delivered.  She was about 19 maybe 20 and had little titties along with a decent hard-body.  No tattoos.  She told me she loved sex and never could get enough so she decided to be a hooker. I loved to eat her pussy.  She always had cum in her pussy for me to eat. She always sat on my face and pushed the cum into my mouth as I jacked off. I loved eating her and always looked forward to eating her.  I dated her for several years and she would always meet me in a motel parking lot that was big enough for my 18-wheeler to park. She was black and I am white. 

[gdukr]

The first time I saw Nancy I was kinda surprised. She was almost classy looking, nice clothes, a pretty young Italian girl with hair in dark, brown ringlets that came to her shoulders. I would find out later that she had a DARK SECRET. Oooooo.

I took her to the sleaziest imaginable hotel, really just a row home that had been broken up into rooms that were for rent but the hour. I had extra time and money and she had agreed to be tied up.

She got naked and when I started rubbing her tits, I noticed razor stubble between them. Like, a lot of it. My first thought was, oh christ, this is, or was, a guy. Everything else checked out, though. Real tits and pussy, and a very feminine, well-proportioned body. She was a girl, just a really hairy one. Fortunately, she was neatly trimmed all over so I soldiered on.

I tied her wrists to her ankles and he ankles to bedposts, so her ass was sticking up in the air and her face was in the mattress. I put on a condom, lubed it and stuck my cock in her pussy. I feel cked her until I got good and hard and then dropped another blib of lube on her asshole.

I shoved my cock up her ass in one go as she said, "No, um I uh, don't do that..."

"Looks like you do now," I said, grinning from ear to ear.

The panic and fear in her voice was too much for me and I emptied my balls into her rectum.

Later, on the way back I started to feel kinda guilty so I apologized for raping her in her ass. Surprisingly, her reaction was to throw her arms around me and say, "It's just that I was so scared..." So, Stockholm syndrome, or, wtf?

[gdukr]

She always had cum in her pussy for me to eat.

Um, not my thing, but hey, you do you!

[gdukr]

Karen, part 2

I had finally broken up with my horrible girlfriend and although I was glad to be rid of her it was weird being in a big, empty house. I decided to go look for a street whore, as much for female companionship as for sex.

I ran across Karen, one of my favorites and asked her to spend the night in a motel with me. The agreement we came to was $60.00 for the night and all the crack she wanted. I figured we'd stock up at her dealer, get a room, fuck a couple of times and chill with the TV. That wasn't exactly what happened...

I bought her a bunch of crack, as expected and we got a room. I fucked her in the cunt and ass, as agreed and then she started smoking. I wasn't really paying attention because I just blown my wad in her ass really hard. I loved ass fucking her because she did this cute thing where she wrinkled her nose when I penetrated her butt hole.

It was only half an hour later when she said, "We have to go".

"What, why?" I asked.

"I need some more," she said, matter of factly.

She had smoked what I thought would last all night in not even an hour, with time out in the middle for fucking. We got back into my car and went back to her dealer and loaded up again. Back to motel for more sex and crack, and again she ran out. It was starting to get rather expensive but I was fascinated to see how much a real crackhead really smokes.

In the end I lost count of the trips we made but it was at least four or five. After the last one it was almost sunrise so I dropped her at home and went to sleep for most of the next day. I didn't know it then but this was one of the last times I would see her.

[gdukr]

Lorraine, the sub-human cum receptacle.

For this one I'll have to qualify my definition of the word "Whore". Lorraine was a lazy, piece of shit, always whining about imaginary illnesses that kept her from getting a real job. I paid for EVERYTHING, and she did as little as possible.

I'm almost more ashamed of my relationship with her than I am of the sex I had with dirtbag hookers. She was a whore, in that she attached herself to me like a parasite for almost 10 years, effectively trading sex for shelter.

She was significantly older than me, had been married twice and was a social retard. The daughter she had pooped out at age 16 ran away to other side of the country as soon as she was able. She had big, ugly, saggy tits with nipples that pointed straight down, and the stretch marks around her navel made her belly look like a paper bag that had been wadded up and then flattened back out. Her ass and legs weren't bad but that was about it. My self-esteem was so low at the time that I thought I didn't deserve any better.

Among her good points were that she could take it in the ass like a champ. She hated it, which was awesome, because that's what she deserved. She also let me tie her up frequently, and even though she complained about it, she kept doing it.

The best sex I ever had with her went like this:
I made her strip completely naked, so that there was no hint whatsoever of romance. I cuffed her hands behind her back and put a dog collar on her. I jammed a ball gag in her mouth and after blindfolding her I led her by a leash down the basement steps. When we got there I had a plywood platform ready with steel loops for the rope I tied her legs with.

When she was on the platform her knees and ankles were tied off to the loops at each corner. This put her standing on her knees with legs spread and unable to move. I tied her wrists to a loop that was directly behind her so that she was leaning back uncomfortably.

Then I took the wooden handle from a toilet plunger and stuck it up her ass. I'm a gentleman so I put a condom over it which looked funny because it was was way too big. She thrust her pelvis forward to get away from the plunger handle which I of course stuck farther and farther up her ass. When I had it buried in her ass I screwed the bottom end of the plunger to the plywood so that it was permanently attached.

With her on her knees, pussy out, and tits sagging over into her armpits, I started fingering her pussy. This wasn't meant to stimulate her, it was more to let her know that I was taking my time and she wasn't going anywhere. I pulled on her big ugly nipples until they got hard and then clipped clothespins on them.
I ignored her attempts at speech through the gag as I faced her and rubbed my cock in sloppy mess she called a pussy. I couldn't quite penetrate her so I jerked off with the head of my cock in her slit until I was ready to cum.

When I came I shot my load on her face and tits. Before I untied her I took off her blindfold and for the first be time she could see what had happened to her. She was a fucking mess.
She was stupid enough to stay around after that and she deserved everything she got, and then some.

Because she's a whore.

[gdukr]

Billy, the assistant manager

This one takes place long before I ever went to a whore...

I was still in college and working nights a lot a corner sandwich shop in the inner city. There were two dykes who lived upstairs who I eventually found out were hookers. One was kind of brawny who, although she had a feminine hair style wore denim head to toe and walked like a longshoreman. Unfortunately, she was the hot one. The other girl was doughy and rather simple looking with coke bottle glasses and a lazy eye was pointing off into infinity.

The Korean owner of the place worked nights with me and I realized after a while that he spent a large amount of time upstairs banging these goofy lesbians. His usual thing was to leave me to close up and head upstairs the shoot his load. On his way out he'd say "If my wife calls, tell her I just left."

The sad, fucked up part was that he took them flowers and presents. Like a date. Like he was in love. Like they weren't whores. Like he wasn't married to his bitch wife.

Eventually he fired me, which was appropriate because I was a terrible cashier and a bad employee. I heard later that he had hung himself in the basement. Poor bastard. He hated the business and his life but couldn't face his family if he jumped ship.

--------

Another anecdote related to the same whores:

During my brief employment at the shop Billy, the day manager asked to be put on night shift with me, just for one night. I found out why when he approached me about "looking the other way" while he dealt drugs out of the shop. He promised me a cut but I politely declined. He was a black guy who had grown up in the neighborhood and I was a dorky white kid who had only seen such things in T.V.

Perhaps still trying to win me over, later as we closed up he said, "Yo man, let's go upstairs and bang them hookers."

Sensing my apprehension he said "It's okay, I'll take the cross-eyed-ed one."

Again, I declined but "cross-eyed-ed" makes me smirk to this day.

[gdukr]

Karen part 3

The last time I did anything sexual with Karen, she was heavily pregnant. I wanted to take her to a motel but she didn't want to, probably because she was really anxious to go smoke crack. I didn't care about her habit before but I have to say I was disappointed in her willingness to smoke while pregnant. Probably unrealistic to have expected otherwise.

Still, though I had very little sympathy for her situation, or for the fact that hormones were making her a complete emotional wreck.

We parked in an out-of-the-way area and I handcuffed her while I played with her tits and jerked off. Her formerly perky, medium sized tits were now huge, with dark areolas and enormous nipples. They must have been sensitive, too because her lip quivered and teared up when I pulled on them.

She became fearful to the point of being unable to speak when I got out a bag of clothespins. I started clipping them randomly to her bloated orbs and all she could do was look at her tits and then look at me, eyes bulging with fear. It was then that I realized the chance of a lifetime for a clothespin fetishist such as myself, her nipples were big enough to take TWO clothespins each.

As I let each of the four mash into her big, meaty nipples, her face screwed up with pain and tears began to flow. This was exactly what I needed and I squirted semen all over the taut skin of her pregnant belly.

I took off the handcuffs and she dabbed her weepy eyes with a tissue. More tissues wiped away the smears of cum from her belly. I found the whole thing exciting but the look on her face when she realized I was doubling up the clothespins on her nipples was hilarious.

[gdukr]

 I had probably picked Colleen up more than any of the other prostitutes I went to. I'm using the word "prostitute" rather than "whore" because I genuinely liked her. She was a confused (over 18)  kid who was hooked on dope and had very little chance of getting her shit together.

This time she had been through the wringer. She looked like she had fallen down a flight of stairs, but it was more likely that some asshole had beat the shit out of her instead of paying.

We agreed that it would be a quick one, I'd play with her tits and jerk off. This was toward the end of the days when I still did this and I wasn't about to risk catching aids now. She was half-naked, her shirt was up around her armpits and her jeans were around her ankles. I was close to finishing when she whispered "Tell me you love me".

Anyone who's been to a street prostitute knows that it's a no-frills experience. They don't pretend to like it which was fine with me because I hate being lied to. When it's over it's over and that's all there is.

But Colleen was in rough shape. Her boyfriend had ghosted her when he went to rehab and she was in jail. I had tried, in a fatherly way, to explain that he needed to break from his past if he was going to get clean. They'd had a "us two junkies against the world" which had been a genuine, if dysfunctional love.

So when she asked me to say "I love you", I did it. It was around then I noticed she was masturbating. I hadn't asked her to, she just did it, and brought herself to a gentle, quiet, orgasm. Not long after I came on her leg. I cleaned her up with some tissues and gave her a hug.

It was a really strange, sad, experience. I really hope she got clean and got her life back.

[gdukr]

There was one ugly whore I picked up on my motorcycle. The whole thing was really fucking weird. She was standing around my with a bunch of other trashy dipshits  and I had to negotiate in front of them. I told her I wanted to fuck her in the ass and she hesitated, saying that some other guy had stuck a knife up her ass.

She turned to one of her fellow morons and said "Remember when that happened?" The moron nodded in agreement.

We finally worked out that I could take her to a motel and fuck her asshole as long as I let her buy crack first. Against my better judgement I parked my bike and we walked through a post-apocalyptic urban landscape to find her dealer. When we found him he was standing with a bunch of other ghetto zombies. Of course she started smoking the crack I had paid for right away and I ended up making awkward conversation with her dealer.

Somehow my motorcycle came up and he started right away with "Where is it? Where's the bike?"

I knew right away he wanted to steal it and told the whore she could keep the money. I walked away and thankfully her dealer didn't follow me.

[gdukr]

Unwisely I tried to get away with a quick one in broad daylight. I met this girl on the street and we agreed to go somewhere secluded. We were behind an abandoned warehouse and she was laying down with her pants around her ankles.

Her shirt was up with her tits hanging out and I was jerking off over them when I heard a car. I thought we were completely hidden from view but when I looked up there were two cops in a van rolling right up to us. I jumped up and ran in the opposite direction as I pulled my pants up. I didn't look back and kept running even though I now had no idea where I was. I jumped off a retaining wall that was four or five feet high and sprained my ankle. I was scared because now I was limping but they didn't catch me. They probably didn't try. I walked like a gimp for a week.

I'm sure they got her, though because they were getting out of the van before she knew what was happening.

[gdukr]

There was a hooker, I forget her name, but let's say Karen. Thin, decent face, nice tits, I was mildly infatuated with her. I picked her up under the El, but since the weather was nice and there were a lot of cops we drove to some woods and did it outside of the car.

She was laying there, half-naked, and it was going to be real quick. I was going play with her tits, jerk off, and cum all over her. I had just gotten going when she had a strange look on her face. She started twitching and making weird noises. I then realized she was having an epileptic seizure. I thought about just leaving her there, but there was a broken tree root sticking out of the ground and it was gouging her face while she flailed around. At about the same time an old guy walked by and saw us. Chivalry won out and I dragged her back to my car.

On the way back she regained the ability to stagger, not walk, so I was steering rather than carrying her. At one point we had to hop off of a short retaining wall, about three feet, so I grabbed her by the armpits and lowered her down. As I did this Karen's shirt came up around her neck so her tits were hanging out. A guy driving by saw it and beeped his horn a bunch of times on the way by. It was an excellent demonstration of the Doppler effect.

After what seemed like forever I got her back to the car and drove her to a safe spot to drop her off. She was still loopy when I pushed her out, walking but unable to speak. I saw her again a few weeks later and she asked me what happened and why her face was cut up. I told her the story and she seemed genuinely touched. She let me fuck her in the ass for free.

[gdukr]

X

[kevb1uk]

I've used prostitutes for around 34yrs, one  maybe every 2 - 3 weeks. I like them better than the Mrs lol

[BrorMyra]

I've used prostitutes for around 34yrs, one  maybe every 2 - 3 weeks. I like them better than the Mrs lol

  I have had sex regularly with prostitutes around the Globe now for 33 years - as a researcher I travel much in my work and the best way of spending the night in a hotel room away from home is to have sex with a young, beautiful, and sexy escort  The only thing I regret is that I was a chicken and did not dare to take the step much earlier! Some of my best sex, paid and unpaid, have been with prostitutes.

However, I have not yet had sex with a streetwalker as I have been the client of more high class prostitutes or have had students as sugar babies. But, I have to admit that I feel tempted to be really "filthy" one day and buy sex from a street whore before I get too old.

[MintJulie]

I don't recall every coming across this topic.  Interesting.

I don't see anything wrong with hiring prostitutes, as long as you're not married or with someone.
I also don't see anything wrong with being a prostitute. I don't look down on them. People need to do what they must to get by.