Couple of friends and myself get off with a hooker, in a car, mid-afternoon
In the late 70s and early 80s, (I’m not absolutely remembering the dates here, but it’s pretty close), a few things happened that resulted in an explosion of public prostitution in Vancouver. First, the police shut down a notorious hook-up joint called the Penthouse which drove the hookers who worked there into other areas of the city (particularly the streets of the West End, an area cock-a-block with residential apartment buildings). Then the Supreme Court of Canada in its wisdom ruled that cars weren’t public places. Prostitution itself was not (and still isn’t) illegal in itself, but solicitation was. Anyway, this all led to prostitution coming out of the dark so to speak and, for a time, overwhelming the streets.
As mentioned, a lot of higher-class hookers worked the more or less residential West End. The heart of downtown Vancouver came to be dominated by quite aggressive prostitutes working there and it became quite a problem as “non-working” women on their way to and from office jobs were relentlessly harassed by guys who “thought” they must be pros. The Eastside near downtown had long been home to “lower-class” hookers supporting their habits although the degree was much less then than it came to be later. It was a pretty sad scene overall.
A couple of friends more or less dared me to “sample the wares”, so to speak, as they had been doing. Dean, my roommate, was going out with a very pretty, nice young woman but from time to time indulged himself anyways (I did an earlier story about jacking off in front of her at her request) - this story was somewhat later than that one. Tom, the other guy, didn’t have a partner but had a very nicely paying job and cruised the areas regularly. I didn’t really want to go with them (I kind of moralistically/judgmentally thought that horndogs such as us pursuing thrills made a bad situation worse. I also was afraid of contracting an STI and hated using condoms). But their stories piqued my curiosity and they assured me we’d go to relatively civilized West End.
Early one afternoon we jumped into Tom’s car and headed down to the West End. For some reason, though, pickings were slim and Tom said we were going to the Eastside “war zone.” Off we drove to a residential side street near the infamous Balmoral Hotel, where Dean and Tom had met with “success” before. We asked a bartender at the Balmoral beer parlour if any hookers were around and he asked us if he looked like a pimp. We sat down and noticed him drop off some draft beer for a disreputable-looking guy, who came over after a few minutes and asked what we were after. To reassure him that we weren’t cops, Dean flat-out said said he and Tom wanted fucks, and that I wanted a bareback blowjob, and that we wanted to do it in Tom’s parked car. The guy told us to wait a minute and shortly returned with a quite-nice looking young woman (early 20s, I’d say). She said she’d do us for $30 each (which was actually a bit pricey at the time), but that we’d have to finish quickly - she had work to do. We gave the guy our money and went with her to the car. The guy followed us a ways behind to make sure everything went down as it should.
As we walked, Tom said he wanted to watch us, so he’d go last. Dean and I flipped a coin, he won, and chose to go first. Tom and I stood a little off from the car and noted that guy from the beer parlour was not far down the street with some friends/associates. Dean got in the backseat with the prostitute, who opened the window a bit and took off her shorts, revealing a quite hairy, puffy-lipped cunt. When he pulled down his pants and uncovered his huge, hard cock, the hooker coolly told him, “No way you’re sticking that thing inside me.” Dean said, “That’s OK, you can just suck it.” The woman took a good part of his big dick in her mouth and started bobbing up and down on it. It was taking a longer time than she wanted, so she told him he’d have to settle for a hand job as she “didn’t have all day.” She jacked Dean’s meat with both hands and, after working it furiously for a bit, made him cum. Dean was famous for his small ejaculations and this was no different as he dribbled a small load over his pubes. The hooker grabbed some tissue from her shorts and wiped him off before he pulled up his jeans and got out, muttering, “What a ripoff.”
I got in with the woman and pulled my jeans down to my ankles. She said, “That’s more like it,” (I was a good couple of inches smaller than Dean, but still very thick). She licked down my shaft and tongued my balls a bit, while I enjoyed a good look at her pussy. She then swallowed maybe two-thirds of my cock and sucked me very nicely, even making some “appreciative” sounds as she pleasured me. She stopped for a minute and said, “I don’t swallow, so you have to warn me when you’re gonna cum, OK?” I agreed and asked her if I could play with her tits. She undid a couple of buttons of her top and resumed sucking me off. Her boobs were a nice, soft handful, and her nipples were really hard. She gently worked my balls with her hand while she blew me, and when she made a kind of tunnel with her tongue as she bobbed her head, I knew it was pretty much over. “I’m going to cum, baby! I have a really big load, so be careful!” I gasped.
She went down to the roots of my cock and I blasted spurt after spurt of my thick, warm cum into her mouth. She took every drop of jizz and sucked every pulsation of cummy pleasure out of me. The romantic motif was broken when she reached over, rolled the window down a bit more, and spat my huge load out on the sidewalk, perilously close to my friends. I pulled up my jeans and told her, “Thanks, that felt really good.” She gave me a quick smile and then I got out.
Tom got into the backseat, pulled down his pants, and unrolled a condom on his small, skinny cock. “Get on your hands and knees, you fucking slut,” he ordered and, when she did, rammed his dick home. He fucked the prostitute so rapidly that the car began bouncing a lot, much to the amusement of passersby. She looked back at him with utter contempt as he quickly shot his wad, and got herself dressed and left the car for her man down the street.
Nobody wanted to sit in the backseat, so the three of us sat on the front bench seat for the journey home. When Dean and I gave Tom shit for being so disrespectful to the woman, he told us, “You guys can take the bus if you don’t fucking like it!” Dean and Tom kept these trips up for a good time, but that time was enough for me.
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