Not your average night cruising for hookers!!

 

This evening I went to cruise the usual beat, just to see how many working girls were plying their trade.  I drove up and down, back and forth, over and around, and spied enough possibilities to keep my attention.  While I saw many interesting candidates, none were clear leaders in the way of being my top focus.  Instead there were numerous women whose company I could see myself enjoying, along with one or two emaciated types who were obviously very into drugs.  Intermittent police lights tended to slow me from taking interest, and the occasional law enforcement vehicle spied parking stealthfully in a vacant lot caught my eye as well.  (upon spotting a likely candidate for immediate pick-up, a cop will park within eyesight of her and then surprise unsuspecting johns as they pull over to invite a working girl into their cars).

I was overly cautious and thus hours went by, with almost none of the same girls at curbside later in the evening as were there when I first got to the strip.  Things were slowing down toward the end of my two-hour window and each "one last cruise before I give up and go home" was met with perhaps a lone figure in the dark shadows rating further investigation in the form of one more look.

Finally, I really did decide:  "OK, this is it, I’m heading back toward the highway, and on home", so I left the strip in favor of the familiar path away from there, but wouldn’t you know it, I rounded a bend when there, in the near distance, was a very buxom woman standing confidently under a street lamp and wearing a vivid pink pull-over which accentuated her feminine appeal.

So I drove around the block once, and by this time of the evening I’d convinced myself that I could indeed risk pulling over to let such a prospect into my vehicle.  Indeed she didn’t hesitate to enter, although a story about her ex boyfriend having just thrown ‘all of her stuff’ outside… and it having since been stolen, soon followed.  "Would I drive down some certain alley to see if her stuff was there??"  No, I didn’t think that would be wise.  So I pulled to the curb in a certain spot to let her dart across the street to check on said "stuff", only to have her explain that it was all gone, upon her return.

Well then we drove around a while, after she let me know that she could use a ride to another spot a few miles away upon conclusion of our date.  She was intermittently on the phone with a best friend, but when the call ceased this woman was quite friendly and sincere in her interactions.  Seems she’s age 25, been homeless for much of her life, though now she has recently been living with her mother, who is in the present charging her rent, but who won’t make her pay rent if she’s going to school.  So the plan is to begin taking classes at a small college next quarter, and to work toward something about which she seemed somewhat passionate.

We talked a bit about me, too, and about how I really admire women, and how much I appreciate that she and the others have availed themselves to the brief and intimate encounters we’ve shared.  I first alluded to, and then blatantly spoke of the social effects of her impressive breasts, and how they can attract a line-up of what are simply ‘the wrong guys’  (personality-wise, and in terms of her personal dating life).

That led me to admit that I’m not really a "breast man", and how I find considerable appeal to all sizes of breasts.  So often it is how well a woman ‘rocks’ what she’s got, and not a simple tape measure comparison, which deems her breasts to be especially appealing.  Yet there was still an interesting dynamic to sharing this conversation as I drove around with a woman whose surroundings obviously knew the allure of her giant-seeming tits.

We were by then looking for a dark area in which to blend-in with our surroundings and commence our date, and the woman was really warming up to me, and to our conversation.  We passed a suitable dark spot, just blended nicely with cars on a dark neighborhood street… so we circled around again to target the very same spot.

Soon we parked, turned the lights off, and I gave her the agreed upon $60.  Just after that we were touching gently and with seeming affection, me being ever so content for a slow build-up to more serious and direct interaction.  She very quickly doffed the heavy pink pull-over, leaving just a well-fortified bra on top of bare skin.  Yet while she definitely had my attention, I still slowly took my time, and exchanged gentle stroking of arms and shoulders.  This was all so comforting to me, and she even added a bit by kissing my shoulders a little. 

After a short while she tugged that bra downward to unveil the full of what could be called her heaving bosom.  These breasts were physically "heavy" to the touch, and yet they were an impressive degree of firm, and they generally stayed in place in impressive fashion sans support.  I kneaded those mesmerizing gems very gently and then fascinated myself with her nipples.  Upon my nuzzling up to her right nipple it became very clear that she was quite responsive to my interest, and she soon spoke of how wet I was making her.  We clutched one another impulsively as I heightened my interest and familiarity with her impressive form.

All the while we continued to talk, and I happened to say that I absolutely love licking pussy, and with that she asked if I wanted to do so right then and there.  She then muttered "I don’t mind getting naked just about anywhere" before struggling her way out of the pants she was wearing, to reveal a bare pussy which she couldn’t resist fingering herself to measure her own wetness.

Moments later I shifted my interest from her beckoning chest to the excitement between her legs, and in a flash I was going at her pussy in upside down fashion, yet with suitable proximity for affording the full effect for each of us.  I quickly came to learn that my companion was an excellent communicator, and I took great comfort in her letting me know when and where to draw the greatest sexual response from her loins.  I immersed

 myself fully in her building sexual excitement and heeded each instruction quickly and effectively.  It was great to feel and sense her rocking and building toward the height of what she wanted (I mean, other than the 60 bucks)…  and it wasn’t long at all before she was making the final ascent toward her climax as might a pole vaulter just prior to letting go of the pole and contorting his/her body up and over the goal.  I didn’t wait for a clear signal of orgasm, instead I just kept dishing it out for her until she finally made it clear that her ship had sailed.

Upon that indication I sat up, as a means of coming up for air, and moments later my prostitute companion happened to look across the street and see or sense somebody in the window there.  This was interesting indeed, but I didn’t see the person, so I wasn’t exactly alarmed, considering how late it was.

Soon after that I took further interest in her impressive bosom, and marveled at the physical weight of those delightful orbs, wondering momentarily about the physical burden involved in having to tote them around all her life, as well as the seeming responsibility to society for the caretaking of such centers of attention.

Not too long afterward, it was my turn for seeming pleasure – although I’d already known plenty there – and I pulled down my pants to reveal my own considerable arousal.  The woman took ages rummaging through her purse for the promised condom, and while that had an adverse effect on my biology, I quickly offset that by reaching for those firm breasts still again.

Before long the condom was on, and she was going down on me…  and it was at that moment when a random car drove down the street and past us.  I’d taken extra care to both find a dark spot, and then park so as to blend in very effectively with the other parked cars there, and we were both down below the sight lines provided by car windows.  So while we hesitated a moment, we went right back to what we were doing, and enjoying.

It was quite early in that part of our interaction and I likely had a while to go before eventually nearing my own climax and (probably) reaching with intent for her bountiful boobs to heighten the experience.  Alas, we heard the noise of another oncoming car, and this one was going at quite a rate of speed.  After it sped by, we each looked up, and she said:  "THAT was a cop!" …

So we quickly dropped what we were doing, and I somehow gathered myself and sat upright soon after the car had turned the corner not terribly far in front of us.  By some stroke of luck I quickly got the keys, and prioritized everything, and started the car and darted away without being spotted.  Now I don’t know at all whether there really was someone in the window across the street, who actually phoned the police to report us there, only to have their response delayed somewhat…   or whether it was just a random pass-by during an average evening…  come to think of it – I don’t even know whether that was a cop at all.

I do know that I was soon driving around with my pants unzipped, my underwear somewhere below my knees, and my own arousal potentially visible to anyone who might have cause to approach or see our front seat from above.   The prostitute was herself getting her clothes together, and tugging at her pants, but without the need to drive simultaneously.  I knew enough to vary my path of departure so as to reduce considerably our chances of being spotted by the could-be cop.

Finally we got a moment at a red light, and reasonable distance from any danger, and I was able to put my wardrobe in place.  Some would have insisted (er, "begged") that the date shouldn’t have been over until the task was completed, but I had already gained so very much from that encounter that I knew the mere $60 spent was nothing compared to the considerable value I’d known.

After our time together, this woman had anticipated spending time at a late night casino with her best friend, and I somehow volunteered myself to drive them there, before departing back home.  We rendezvoused at a 24-hour gas station, and the ‘best friend’ emerged from within for an awkward-seeming introduction.  It seems the friend knows what the woman does for a living, but they don’t share war stories about her now 7 years in the trade.  On the path toward the friend we had to roll down all of the windows as ‘the scent of a woman’ was clearly and undeniably permeating the vehicle by the time my tongue was done with her.

I was surely well out of the zone of normalcy as someone this girl would have encountered by mere social chance (in a non-working environment) so I suspect strongly that the ‘friend’ understood that we’d been trading sex for money, but nothing was ever spoken.

Well we get to the casino after needing to shuttle the friend home for a moment, so she could drop-off purchases made at the all-night store.  And while the friend is age 29, it seems she still didn’t possess her ID, so she would have been denied entrance to the casino for that reason.  So they enlisted much-older me to help them get her past the door guards in the way that perhaps the woman would seem even older if indeed she were in the company of an older-yet person.  The prostitute went into the casino by herself, as it was quite likely that she would be carded at the door no matter the case.

She spent lots of time primping in the make-up mirror, for this late night casino trip, and that despite a more casual and comfortably appealing look when she was at curbside earlier, having only just arrived for the night shift not long before I picked her up.

I didn’t stay long at the casino at all – just long enough to use the men’s room…    but it was quite the interesting experience and potentially the closest call I’ve ever had in the biz.

I’m quite content at the fact that I got the woman’s number, and that I can call her anytime for a replay of most of what was a fulfilling encounter, climax or not.</span

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It should be noted that this woman might have been 5′ 4" or 5′ 5", and that if one were to venture a guess as to her weight, 150 or 160 might be a good guess.  This was indeed a "real" woman, albeit one with improbable boobs.  She gets grand applause for her very earthy demeanor despite eye-catching bosom and seven years as a working prostitute – I don’t know how she could keep so well grounded.  Another exceptional attribute was her evolution toward being someone who comfortably instructed her sex partners on how best to administer her sexual pleasure.  What a bonus in a person – and something which shouldn’t be so very difficult to find in others.

I arrived home both tired and considerably intrigued over this woman who, with naked and sated pussy glistening in the darkness, at one point said to me:   "wanna fuck me?  for an extra $20 you can fuck me".   When the evening began, I was really anticipating a blowjob, if anything, well before I had any sense for just who might be administering same.  And while I have no cause for hesitating about fucking that woman next time, I for some reason didn’t have that in my thoughts tonight.

That even though I’m not especially a blowjob-hungry guy either.  In the business of prostitution, and especially for ‘car dates’, blowjobs tend to define the dates, because they are relatively easy to administer in the cramped confines of a vehicle.  Given nothing but pure choice, I would much rather have fucked the woman tonight than obtain a BJ.  Though it has been quite a long while since I last climaxed from a BJ…  not for reason of biological limitations, but simply because my last several encounters had been in settings where fucking was comfortable and easy.

This was such an odd-seeming and surprising encounter start to (almost-) finish that I had to jot it down A.S.A.P.

I hope to be seeing that woman again.

 

This has been the mindset of your John