Brockton Nights Pt. 01

This story happened in the early 2000s. Sadly I don't recall the specific year, but I was in grad school at the time and living in Brockton, MA so it had to be pre-2006. Brockton has, for most of its existence and even into the modern day, had a fairly active street prostitution scene. While I availed myself of it a fair number of times over the time I lived there, on this particular evening, I was not actively looking for a hooker but found one anyway.

I'd been driving home from running to an all night drugstore for something or other and had accidentally dropped a CD on the floor of my car as I'd tried to change it. Rather the fumble for it driving I pulled into a tiny parking lot right off of Main St so I could stop the car and see what I was doing. As I retrieved the eloping CD I saw a small, middle aged woman standing right near my driver's side window. She gave me the universal "roll down your window" hand gesture which I did.

"Hey, baby. You know this is resident only parking right?"

I began to explain that I was looking for my lost CD but I only got as far as looking before she, mistakenly thinking she'd taken my meaning, smiled and interjected.

"Oh, you were looking for a date? A date I can absolutely do." Had she not been leaning forward so strategically I might have corrected her. She looked to be in her forties but she still had a great figure, wavy dirty-blonde hair and a rack that still looked spectacular in a low cut, well worn tank top. It was mid autumn so it was chilly but the real Massachusetts cold hadn't set in yet so she was only wearing a dingy black hoodie but she had obligingly left it unzipped enough of the way to put her assets clearly on display. I unlocked my passenger side door and asked her to hop in.

A few minutes later we were pulling back onto the main strip and she began directing me to "her spot". We did the obligatory "you're not a cop are you" dance (though to her credit she began massaging me through my pants while we did it which was quite nice) and she eventually had me pull off onto a side road behind some recently built chain stores and asked me to shut off the car.

"So what were you wanting tonight, baby?"

"Just a blowjob would be fine."

"You got it, hon. That'll be forty okay?"

I fished out my wallet and handed over the cash which she promptly folded up and discreetly stuffed into her bra and then began tying her hair back into a pony tail.

"You are not gonna regret this at all. Trust me. I'm good." she added with a little wink as I put my seat back and began unfastening my pants. She gave a quick, furtive look around and then, once satisfied we were alone, asked me to keep an eye out for cops, just in case citing "my head's gonna be a little bit too low for that" as the reason and then lowered her head down to my lap.

I felt her warm, soft lips wrap around my cock. At the time I'd only had one or two other experiences with professional car dates so they still felt a little awkward to me. I may have still been soft when she got her mouth on it but it took only a few seconds of her gently pressing the head of my cock against the roof of her mouth and rolling it back and forth with her tongue to change that. As I began to stiffen she began to bob her head and I couldn't help but watch my rapidly hardening dick vanish in and out as it passed between those creased-yet-highly-experienced lips.

As she sucked me I slid my hand down from where it had been resting on the small of her back and I slipped just the fingertips beneath the gray tank top (which, decades earlier had probably had the Aerosmith logo on it from the looks of it) and asked;

"May I?"

She pulled her head off of my now achingly engorged cock with a wet popping noise and said,

"Aren't you a fuckin' gentleman for asking?" before taking my hand and guiding it up and finally under her bra. "Mmmm...they don't feel like 43 year old tits do they?" I would have agreed with her that they most certainly did not, however, at that moment she resumed blowing me with even more enthusiasm than she had been a moment ago and my grasp of the English language seemed to leave me for some reason.

As I fondled her breasts she began sucking more forcefully. She was taking me all the way down her throat with every downward bob of her head and making it seem effortless. Her cheeks hollowed with every increasingly vigorous suck and her tongue was in a perpetual hurricane motion around my shaft and head. For the next few moments the windows fogged as the car became filled with the sounds of hungry slurps and moans.

She reached her hand into my pants and began to tease my balls with her fingertips as she started in on her endgame. She pulled her head back off just long enough to breathlessly ask if I was "gonna give (her) that fucking cum, baby?" While I was in no mental condition to time it, I don't think I lasted another full two minutes in her mouth once she resumed sucking.

My orgasm hit hard and suddenly. One second I was panting and tensing up with anticipation and then I was melting back into the driver's seat and flooding her mouth with semen. She gave a very pleased with herself moan as that first warm, salty gush splattered across her tongue but she didn't stop and, unlike many streetwalkers I would later discover, she kept sucking me for the duration of my orgasm. She took my entire load without missing a beat and when she finally pulled her spit and cum slicked lips off of my spent cock she gave me an adorable wink before opening her door and leaning just far enough out to dispose of what I'd left in her mouth on the chilly Brockton side street.

She asked me to drive her back onto the main strip to a convenient store that was still open and I happily obliged. As she got out she informed me that she could usually be found around this area most nights.

"Seriously, pick me up whenever, sugar. You're a straight up gentleman not to mention a nice stiff cock." The latter she gave a friendly squeeze through my pants again before slipping out of my car.

I looked for her a few other times but never managed to spot her again. It was disappointing but the experience did give me a great fondness for periodically cruising up the Brockton stroll which resulted in me having many more encounters over the next few years which I will write about another time.