VERY long post, but real person, not spam!
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'street walkers', 'hookers', 'whores' or whatever other name you wish to
ascribe to those women who accept money in exchange for sex, I've certainly
had my share over the years. As you will see, paying for sexual services is
an extreme gamble: It can buy you one of the most intensely erotic
experiences of your life, OR it can buy you a situation that can be
embarassing, costly and even dangerous. This essay features both heights of
orgasmic ecstacy and depths of desperate mistakes. I present the following
factual account with neither pride nor shame; it is merely a record of a
memorable string of events in my life. Judge them (and me) as you wish.
My first actual experience with prostitution came in the form of a quick
blowjob from a Detroit street walker in either late 1987 or early 1988. Four
of us guys were riding around (it was a Winter night, as best as I can
recall) looking for action when one of the fellows spied a slightly chubby
woman who looked to be in the mood for action. I was asleep at the time in
the backseat, however I woke up quickly when the prospect of sex presented
itself. (I should also state that I was an unwilling 20 year old virgin at
that time, a prisoner of my own nerdy unattractiveness). From what I can
recall (I had had my share of alcohol that night, as with many of the other
nights described herein) 3 out of the 4 of us went up to her apartment, one
at a time, for head. One friend was up there a rather lengthy amount of
time, while the next friend's time was relatively short. I went last and,
due to the liquor, beer and sleepiness that prevailed over me, was unable to
climax. If it were not for the fact that this was my first ever blowjob, the
whole experience could be discounted as rather forgettable.
My next experience with prostitution came about within a few months of the
first incident. A friend (the man who was the first to go upstairs during
our previous adventure) and I went to Jumbo's bar in downtown Detroit. For
those who are not from this area (or who are not familiar with the oldest
profession as practiced here), Jumbo's was notorious for a number of years
as THE location to meet a prostitute in the area. I had smoked an entire
joint and downed a couple of rum and cokes that night, but this did not in
the least detract me from my goal of FINALLY unloading my burdensome
virginity. I noticed a long legged, young blonde woman with small breasts
for her size (just my type!) in the bar that night and made my (nervously
awkward) approach. After some meaningless chit chat, we talked pricing,
which, if I am correct, was negotiated to 60 dollars for the hour. After
reaching that agreement, the two of us made our way to my car, then to a
nearby 'no tell motel.' I paid something like $10 for an hour's time and we
went off to our seedy little no frills room. Everything that night was
strictly safe (she would not even let me eat her pussy), but the blowjob and
vaginal sex she gave me that night was outstanding. We fucked with her on
top (for the first 5 or 10 minutes), then missionary style for the duration
of the hour. I returned to the bar a happy (new) man, and my friend and I
departed soon thereafter.
The third encounter was one of the truly horrible experiences I had with the
oldest profession, so I won't linger while telling it. The same friend from
'experience number two' and I were once again cruising the streets of
Detroit when he insisted on stopping for a blatantly UGLY street whore whom
I would have been more than happy to pass by. As he was driving my car, he
accepted a b.j. from her in the front seat while I reluctantly awaited my
turn in back. Unbeknownst to him, the bitch had pickpocketed him. She had
also pickpocketed me while giving me some rather lame oral servicing and, on
the excuse that she had to urinate, climbed out of my car and took off. Once
we (two admittedly drunken chaps) finally figured out what was happening, we
attempted to locate her. This only resulted in my friend being pulled over
and arrested for impared driving. Luckily the police at least allowed me to
drive myself home. What can I say except that the bitch got the best of us.
The next episode encompasses a much more pleasant and successful experience.
After leaving the same friend's home (tanked to the gills, I might add...),
I spied a cute, petite blonde walking rather briskly on Fenkell Avenue (in
Detroit). I don't recall what all we said to each other, but within about 5
minutes time we were back at my friend's house, he granted us the living
room couch and we got naked. There was no actual intercourse during this
encounter, only mutual oral sex. At age 22, I am sorry to admit that this
was my first time tasting pussy (Trust me when I say that had it not been
for my nerdy looks and overprotective parents as a child, this experience
would have taken place at LEAST 10 years sooner!), and as such this remains
my favorite type of sex act. I also ate out her widened bunghole and she
sucked my dick in several positions. She was remarkable clean (both front
and back) and made no attempt to rip me off or rush the process. She later
asked me to drop her off at (what she admitted was) a crack house. I felt
genuinely sorry to see that she was caught up in that destructive culture
and wished I could have somehow 'saved' her. The sex was awesome and, beyond
the apparent drug addiction, she seemed like a truly nice person worth
salvaging. Sadly, I never saw her again after that night.
As best as I can recall, there were no further experiences with the oldest
profession in my life until 1995, and that one was negative. In short, I
picked up a blonde, reasonably attractive street walker on Michigan Avenue
and, after assuring myself that she was not a police decoy, I asked her how
much she would charge me for a golden shower. She seemed a bit taken back
(although not at all offended) by this request and agreed to perform this
act for $50.00 (or somewhere around that amount). My (at that time) trusting
nature again betrayed me when I handed her a $20.00 'deposit' before she
headed off into a darkened house. The end result is so predictable (in
hindsight) that it hardly needs to be given, but....suffice to say, this
street hustler (undoubtedly) got high while I waited in the car for awhile
before finally deciding to forego any attempts to get it back. I headed home
poorer although infinetly wiser that night.
The next experience (from the Summer of 1997) also involved a loss of money,
although not my own. I had gone cruising around the 6 mile/John R road area
of Detroit with another long time acquaintance of mine. We picked up a
rather attractive/reasonably healthy looking braless woman and drove around
to a backstreet where not much besides burned out and/or abandoned houses
stood. After some haggling, she agreed to blow us both for $40 (my
acquaintance provided all of the money). We drove around the block again,
because she needed to 'pick up something' (I'm sure you readers can see this
one coming already...). She jacked me off while I drove, and once we reached
the area where she wanted to be let out, we let her out and, well...you know
the rest... At least the handjob I received made this venture somewhat
worthwhile.
Incidentally, for those of you who may be inclined at this point to say,
"Shit, this guy's a moron to keep losing money to these whores!", I can only
say that, before you pass such judgement, consider: The women involved
demanded money up front (they wanted a 'deposit' before sex could even be
discussed), and since refusing to let them leave my car at any point would
constitute a serious crime in itself (unlawful imprisonment against one's
will, to say nothing of possible kidnapping charges), what choice did I/we
have ? Another quick point I would like to make regarding double standards
in our society is this: Why is it when a woman gets bilked by a man who she
thought 'loved' her, often to the tune of tens of thousands of dollars, the
general refrain is, "Poor thing!", yet when a man loses money over sex, he's
"Stupid!" ? It would appear to me that either we are BOTH victims or we are
BOTH fools. In any case, I'll get off the soapbox and return to our
storyline now.
The next experience did not come until 1998, when I was on my way to work
around 7:30 am in the morning. A blonde, 38 year old (so she told me later)
chunky gal named Sherry was standing on the side of Dequindre road just
North of 8 Mile Road (on the Warren side of the border) , austensibly
hitchhiking. At first she was a bit reluctant to get in my car (my license
plate at that time contained an 'X', which is a common letter on police
license plates), but before long we were parked behind a nearby party store
and her mouth was wrapped around my hard on. I certainly got my $20 worth
out of this experience, and while Sherry was admittedly not much to look at,
her skills as a pro were well developed and appreciated. The bruises on her
arms resembled those found on many 'junkies', and, as I did not have a
condom with me at the time, I decided to forego any chances at intercourse
in case she was a 'sharer' when it came to needles.
We now come to the worst prostitution-related experience of my life. During
the early Summer of 1998, I was arrested for soliciting a police decoy at
the corner of 8 Mile Road and Schoenherr. The long and short of it is, I was
cuffed and 'booked' then and there in the back of the police cruiser. As per
Michigan law, my car was also seized on the spot. Subsequent proceedings
only confirmed what I had strongly suspected all along: The 'justice' system
in the U.S. is as corrupt (if not MORE so) than those in any
'totalitarian'/'rogue state'/'Axis of evil' nations in the world. At my
pre-trial hearing, the house council attempted to scare me (as well as the
other 40 or so men caught up in the same sting operation) with tales of
mandatory jail time in the Wayne County Jail in Detroit. Supposedly, for the
'modest' fee of $500.00, he would represent me and most likely get the
charges dropped. I would have none of this and said that I would go with the
legally mandated free legal services offered to all those who face trial.
Likewise, I also flatly
refused to pay the outrageous sum of $750.00 to reclaim my car, as this car
was literally a month or so away from dying on me. The long and short of it
was I got a relatively light sentence ($150.00 fine with no criminal record
as long as I stayed out of trouble for the next 6 months, which I did). The
police department in turn received a car that had literally become a danger
to drive and was not worth the costs of towing/impounding. The society that
opposes prostitution and pornography further gained a lifelong foe (myself),
and Detroit itself gained at least 2 class action lawsuits against such
on-the-spot vehicle seizures. Given these circumstances, I would have to
admit that I feel more like a 'winner' in this regard than a 'loser.'
During Labor Day weekend of that same year, I happened upon a 23 year old
mini skirt and blouse wearing cutie just blocks from my home.
The 'once bitten, twice shy' rule being in full effect here, I circled
around the block once, checking for any sign of unmarked police vehicles and
found none. I then doubled back and picked up Susan Kimberly. In all
honesty, while she was a bit 'cracked out' and showed some signs of wear and
tear (two missing side teeth, premature lines under her eyes and a bit of a
vacant stare), by hooker standards she was actually reasonably cute and
maintained a nice slim build. We drove to a semi-deserted section of Detroit
and had satisfactory sex in the back of my car. After the act was
consummated, she simply pulled her panties back on, rolled her little skirt
down, said "Nice meeting you!", and took off walking down the street. I then
wound up driving home, drunk and nude from the waist down.
After not seeing her for almost a year to the date, Susan Kimberly again
entered my life when I recognized her on the street 2 blocks away from my
home. She had on a white t-shirt and tight white short-shorts, but after a
few minutes of talking and a short walk to my home, she was wearing nothing
but I blissful smile as I rammed in and out of her on my living room floor.
This was a much better fuck than the one we shared the year before, and I
could tell that even Susan the 'pro' was enjoying the experience. I banged
her missionary style, enjoying the reasonably tight feeling of her hot,
naturally lubricated hole. Afterward, I paid her an additional $40.00 for an
extremely satisfying golden shower (over my cock/balls/pubic area)which took
place in my bathtub. Immediately thereafter, Susan dressed in record speed,
said "Love ya!", and took off literally running out of my house with the
$80.00 ($40 for the fuck, $40 for the golden shower) hastily tucked into her
pocket. Would anyone care to venture a guess as to where she was going
and/or how the money was spent ?
At this point, my adventures in prostitution shift mainly to areas outside
of Michigan. In 1999, I took both my second trip to New York City and my
first trip to Europe. At a bar in New York (the name of which I cannot
recall), I picked up an average looking 20-something blonde who possessed a
charismatically quirky personality. After failing to get a room at the first
motel we tried, we eventually settled on a second choice nearby. This gal
had breasts that were perhaps in the smaller end of the 'b' cup size and a
shaved pussy, both of which complemented her overall appearance perfectly.
She gave my condom-covered cock head, and afterward we enjoyed intense sex
(missionary position) while I sucked her beautifully small tits. As with
some of the other ladies of the evening that I've met, my enjoyment with
this woman did not soley depend on the sex; her personality also helped to
enhance the experience.
My next two experiences took place in 1999 in the grand city of Amsterdam.
In all honesty, I have had the best sex of my life while in that city, and
even the act of WRITING about these actions makes me horny and, truth be
told, downright giddy.
My first Amsterdam lay was a blonde 20-something woman who was reasonably
attractive but not at all personable. The sex which consisted of her giving
me head (by Netherlands government policy, this is ALWAYS done with a
condom) followed by a missionary fuck was rather rushed and I got the
impression that this gal flat out did not like me. The encounter that I had
literally minutes later, however, forever bonded my erotic emotions to this
beautiful city and her population.
I don't recall her name and never got her age (although I'm guessing she was
between 19-21 years old), however I will never forget our brief meeting.
This angel in human form had platinum blonde hair that nearly reached her
waist. From the start, she came across as a friendly person who genuinely
enjoyed her occupation. Her face, which was highlighted by her large, soft
eyes was fresh, young, Nordic and almost 'innocent.' Her boobs (perhaps 'b'
cup size and quite firm) were topped by perfect pink nipples and sat atop a
perfectly flat belly. Her legs, which were long in proportion to her overall
body (she was perhaps 5'3" tall), led up to one of the nicest, roundest,
smallest, sweetest asses I have ever laid eyes on. Her skin also had a nice
sun tan tone to it, a perfect complement to her hair color. As I had just
had intercourse minutes before, I didn't think I could shoot my load again
(I was wrong), so I contented myself with going down on this goddess' sweet
smelling/tasting pussy and extra-tight bunghole. The sensation of my tongue
sliding deeply into this Netherland gal's netherholes stands out as one of
the best sexual experiences in my entire life. She laid on her back and
spread her legs like a seasoned cheerleader, allowing me ample access to her
pink treat. In order to gain the maximum entry into her lovely back door, I
had her get on all fours while I (orally) penetrated her from behind. While
my tongue was deep inside her rectum and my left hand massaged her moist
cunt, my right hand jacked my dick off to an intensely powerful orgasm. For
the equivalent of around $40 U.S. (the average price for a lady in
Amsterdam), I obtained my favorite sexual activity with a girl who would
never even BREATH in my direction in the 'real world.'
After this quick, unexciting paragraph, we shall return to more erotic
adventures overseas: In January of 2000, I picked up a blonde street walker
near Mt. Elliot road on 8 mile (in Detroit). Once I saw her extremely
weathered/unhealthy looking face up close, I acted as though I was turning
chicken and let her out of my car about 1 block down the road. She must have
gotten this treatment quite a bit, as she did not seem at all surprised or
angry.
Arriving back in Amsterdam in 2000, I was lucky enough to find a shapely,
(approximately) 20 year old babe looking for a customer. This particular
woman had larger breasts (as well as a slight 'bubble butt') than I
generally prefer, but her overall figure was 'symmetrical' so this was not a
problem. She spoke almost no English (the only language that I know), so
communications were kept to a bare minimum. She would not allow me to
perform oral sex on her, and her oral skills were at best adequate. The
intercourse itself, however was exceptional. We started out in the
missionary position and shifted soon thereafter into a doggie style posture.
This chick's butt cheeks jiggled and shook nicely with each thrust. It
wasn't long after that when I shot my load like a sex starved animal,
grunting and moaning loudly the whole time. Once again, this was $40 well
spent.
My next experience with sex for a fee did not come until exactly one year
later (once again, I was in Amsterdam), however the sheer intensity of the
following three experiences made the wait seem worthwhile.
'Gal #1' was similar in build and looks (generally speaking) to the woman
cited in the previous entry. This one, however allowed me to vigorously
tongue both her pussy and asshole before we commenced some heavy duty
fucking. Again, we started out in missionary, then shifted around to doggy
style sex. Aside from the oral foreplay, this was essentially a repeat of
the last experience, which is to say that it was quite enjoyable.
'Gal #2' was a lovely, petite, dark haired babe with an especially friendly
disposition. I did not go down on her and was a bit 'limp' from the
beginning due to my hectic travel schedule and lack of sleep. Her above
average oral skills quickly remedied that, and before long she was riding my
rock hard member as I caressed her legs and (bra covered) tits. We shifted
to a missionary position after a few minutes and it was in this posture
that, while tightly gripping her smooth ass, I attained an orgasm similar in
intensity to the one reached with the Amsterdam gal in 2000. After we both
go re-dressed this 20 year old woman was kind enough to assist me with some
needed directions. It is positive occasions like this that more than make up
for the negative fiascos that I've endured with other ladies of the
evening/prostitutes.
'Gal #3' was a slightly chubby, blonde, cheerful, stereotypical Dutch girl
with uncharacteristically small (for her overall build) boobs. We engaged in
some hot '69' action during which I tongued both her pussy and butthole
deeply. Our sex was limited to missionary style, and no orgasm was attained,
however the overall experience was still a fond one.
Amsterdam has a persistant reputation as being a hotbed for prostitution,
and while their red light/porn districts are as exciting for me as
Disneyland would be for a small child, I must point out that the 'lewd'
areas encompass only a few city blocks of the entire city. Furthermore, the
ladies of the evenings in Amsterdam, while still technically prostitutes,
are extremely different from their (for the most part) heavily drugged up,
old before their time American street walking counterparts. Most of the gals
in Amsterdam are (at least in my opinion) first rate for looks, and, in at
least some cases, they have charismatic personalities to match. I say this
so as to assure anyone NOT inclined to illicit activity that there are
plenty of other activities and positive things to do in Amsterdam. Even
without the 'red light action', Amsterdam (like most regions across Europe)
would be a beautiful city populated by attractive and friendly people.
Back in the ol' U.S.A., during the Fall of 2001, I was returning home from a
bar night with some workmates when, lo and behold, after a 2 year absense
from the area, 'my' hooker (Susan Kimberly) and I again crossed paths. She
was walking in her old turf when I happily picked her up. We pulled off to a
darkened side street where she provided me with a satisfying blow job while
I stuffed my hand down her pants and fingered her (wet) pussy. This
certainly wasn't "Amsterdam quality" sex, however it was well worth my money
and time.
My next experience with prostitution again involved Susan Kimberly and took
place only a couple weeks later. On my way home from visiting a friend (the
same friend who lost $40 to the street walker in 1997), I spotted her on her
usual street and picked her up once more. We returned to my friend's home
where, after some price negotiations, she agreed to take us both on at the
same time for $50.00. After we entered his bedroom and stripped, she took
his (condom covered) dick in her mouth and bent over so I could enter her
pussy from behind. Unfortunately, I was unable to attain a full erection due
to my friend's presense in the room (I am used to 1 on 1 sex), even after
she later attempted to 'revive' me with her expert head skills. Susan
Kimberly has never allowed me to eat her pussy or ass to this day, but
overall my experiences with her have always been positive.
July 13, 2002 was the date of my best experiences with prostitutes to this
day. I made my way to the Red Light District during a 14 hour layover in the
lovely city of Amsterdam to partake in the joys it offers visitors 24/7. My
first gal was blonde, 20-ish in age, slightly chubby but reasonably
attractive, however her manner was too rushed for my tastes. The quickie
fuck we shared was more or less forgettable, especially when compared to the
experiences which were to follow.
Gal #2 was another babe in her early 20's, slightly built with full lips and
small breasts. She and I '69-ed' vigorously for several minutes. I sunk my
tongue deep into her pussy and bitter/sweet bunghole before unloading a
sizeable portion of spunk into my condom.
Gal #3 (I believe her name was Gabby or Gaby) was arguably the best of the
lot in terms of looks. Claiming to be 18 years old, this babe was blonde,
small chested, pale skinned, VERY long legged for her size and slim. The 69
session and subsequent fuck we shared was extremely intense. While I could
not ejaculate again in so short a space of time, the experience was
thoroughly enjoyable nonetheless. As was the case with gal #2, her smell and
taste were both awesome. Also, I could grasp and completely cover an entire
tiny butt cheek with the palm of my hand! :)
Gal #4 had blonde hair, a NICE round little butt, a suntanned complexion, a
BIT of a facial mustache (neither a turn on or turn off for me in and of
itself) and LONG pink nipples. We fucked for a bit, although I was not able
to attain climax with this woman until I jacked myself off while sucking on
her pointy nip tips.
Gal #5 (Jessica, if I recall her name correctly) was the FRIENDLIEST
prostitute I've ever met. As with many of the other gals described herein,
she was very slender/small breasted/long legged. Her strawberry blonde hair
cascaded past a fresh, freckled face that always seemed to be smiling. At
the conclusion of our fuckfest, she even notified me that I had some time
left if I wanted to do 'something else.' I opted for sucking her nipples
during those remaining minutes.
As I was leaving, I asked Jessica if there was any place that I could find
trannie girl hookers. Without missing a beat, she gave me directions to the
streets that cater to trannies and their admirers.
Upon reaching that section of the district, I made the mistake of
contracting the services of a REAL (chunky) woman believing she was a
trannie (her face appeared somewhat masculine....) After I explained the
situation to her, she called down the street to her friend, a true
transexual. I don't recall her name, however she appeared to be about 24
years old and sported long black hair, a suntanned complexion, fairly
long/smooth legs, realistic looking/feeling breasts, a girlish ass and a
hormonally-altered womanly voice.
While the original gal sucked my dick, I felt the tits/smacked the
ass/licked the balls/sucked the (comdom covered) dick of the trannie,
managing to get all 7" down my throat. (For those keeping track, the chunky
gal was #6 whereas the trannie was 'gal' #7)
At 19 years of age, Gal #8 looked almost 'innocent.' A real 'girl next door'
type, this talkative and cheerful lass had platinum blonde hair, a somewhat
cherubic (but without being at all fat) face, a small yet filled out frame
overall and the obligatory nice little butt that I so crave in a woman. She
sucked me before we fucked and my eventual orgasm was achieved via self
satisfaction as a rubbed her smooth ass with my free hand.
I only had 2 hours to spare in Amsterdam on my way home (July 27), so gal #9
was something of a 'last resort.' As it turns out, she was also a complete
waste of money and time. An older, semi-attractive blonde, this woman was
extremely rushed and impatient. Also, she would ONLY suck my dick and did
not even remove her thong during our session! :( Needless to say, I would
NOT return to her.
While in Maryland (July 30, 2002), I looked up area massage parlors in the
Yellow Pages and was pleasantly surprised to find a generous selection
within reasonable driving distance of my motel. I won't name the parlor (as
the activities that we indulged in were no doubt contrary to state and/or
city 'public decency' laws), however the gist of the situation is as
follows:
The gal in question was about 25 years old, perhaps 4'10" tall, petite, and
sported shoulder length black hair.
After urging me to get into an all fours position on the padded table, my
magic-fingered partner rubbed my genitals/anus with warm oil for several
minutes. At that point, I turned over onto my back and she asked if I wanted
to 69 with her. Of course I agreed and she subsequently climbed atop me,
pushing her pussy/butt firmly into my face. It didn't take long from that
point; after perhaps 2 minutes of tonguing her clean, tight vagina, I shot
several strong loads of semen into her hands (I should state here that I
could not SEE whether she was actually sucking me or jacking me off with
well oiled hands. In all honesty, the orgasm I experienced was so satisfying
that I hardly gave it any thought at the time).
(During 2003 and 2004, spent paid time with several other ladies of the
evening and enjoyed intercourse, felatio, cunnilingus and analingus. For the
sake of space, I won't bother with details herein except to say that it was
all good ?)
In 2005, I again returned to Amsterdam for some illicit fun. Highlights
included a golden shower episode with a very attractive, small built, 18
year old gothic chick, a scat/mutual oral sex session with a tall/thin 26
year old woman named 'Gloria', a suck/fuck session with a very thin 23 year
old woman and a brief felatio/"touchy-feely" session with a rather
attractive young Asian woman.
I would be happy to hear your own stories in this regard! ?