Chapter 1
They say prostitution is the world’s oldest profession but it is also one that
constantly reinvents it’s self to the changing times. With the growth of home computers,
video cameras and the Internet, a totally new form of prostitution has emerged, one that
allows both the prostitute and the John/Mary anonymous sex, free from most of the dangers
inherent on the street. Of course this form of prostitution does have its downsides.
Without any physical contact between the prostitute and the John or Mary, any actual sex
is limited to masturbation by either or both the prostitute and the viewing customer.
Still, for many who pay for the services of the online prostitute, this can be much better
than masturbating to photos in a magazine or while watching a pornographic video. At least
when turning to an online prostitute, two-way communication can be had via text messages
or sound.
I think it is clear why some (actually many) people, both men and women, will turn
their computers on to be turned on by an online prostitute. Being anonymous is a great
draw. No worry of being exposed (figuratively and literally). No need to travel to the
more dangerous areas of cities big enough to find a prostitute. The Internet is always
there, 24/7/365. For the John or Mary, no need to worry that the prostitute might turn you
down because you are too fat, too thin, too old or just plan ugly.
For the online prostitute, the advantages are also many. As it is with those who
patronize the online prostitute, there is no worry about the dangers of sexually
transmitted diseases. Except for the possibility of family, friends or neighbors coming
across their Web page, they like their clientele can remain anonymous. Though the money is
seldom as good as can be made in person to person encounters, it can provide a second
income without leaving the home. For some, perhaps for many, it is just the thrill of
having some exhibitionist fun.
For me, it was the last two that drew me to it - a little extra cash and having
some exhibitionist fun.
First, I should explain that because I am a guy, I recognized that as a guy I would
be somewhat limited in the amount of money I could make because if I were to satisfy my
customers I would be expected to satisfy myself. There is just no way a guy can fake an
orgasm as woman can. Once I came, my customer/customers would lose interest and it would
take some time before I could work up to another erection. I also realized that though I
consider myself straight, a majority of my customers would be gay men. This did not
trouble me because even though I do not consider myself gay, I have had a couple of
experiences with men and don’t have a problem with the idea of having sex with another
man.
I mean, think about it. Really think, I mean. Once you can get past the prudery of
the mind and let the body be your guide, sex is pretty much sex whether it be with the
opposite or same sex. What difference does it make to the body if the lips are those of
the opposite or same sex? What difference does it make if the lips and tongue of your
partner are the same or opposite sex when they touch your most private parts?
I know. I know. You are wondering about anal sex. But you must know there are a
number of heterosexual partners, including those who are married, who do indulge in some
anal sex. A few women like to be fucked in the ass and there is often some licking of each
others anus. I have no idea what the numbers might be but I do know some women will finger
fuck their male partner and even some who will use a dildo to do the job. The anus is very
sensitive and can provide a surprising amount of pleasure provided some care is exercised.
Check this out on your own if you doubt me. You might be pleasurably surprised enough to
ask your wife or girl friend to fuck you.
Now before I tell you about my experiences as a male, online prostitute, let me
tell you some of what led up to it.
I am not a kid. I won’t say just how old I am but let me just say I have been
married for a number of years and have fathered a couple of children. As I already told
you, when I was young and before I got married, I did have a few sexual experiences with
other young men. Back in those days, these experiences were often the result of being a
little drunk and sexually frustrated from not having a girl for awhile. As the expression
goes, I was horny and masturbation was not relieving the frustration. Sex with another guy
seemed like a good substitute when for a variety of reasons I wasn’t getting any from a
girl.
After I married, I was true blue with my wife and never cheated. I enjoyed a good
sex life with her for many years before her interest in sex waned while mine didn’t. I
regressed so to speak to my younger years in the sense that I returned to masturbating to
fill in the void. As masturbation became my prime source of sexual pleasure, I began to
remember the pleasures, few as they were, when having sex with other men. Gradually, the
sexual fantasies indulged in while masturbating moved from thinking about hot, young women
to men. This was easy and natural, I think, because the preferred form of masturbating was
to use my own saliva to give myself a blow job with my hand.
Pregnant pause here. There are very few men who would turn down a woman who wanted
to give them a blow job. Just the idea that a woman would be willing to do that can cause
most men to have an erection. There are some men who would swear up and down they are
straight but who wouldn’t prevent another man from blowing them so long as they weren’t
expected to return the favor.
So as I was saying, the hand job blow job became my favorite way to masturbate and
since this resulted in me remembering those few times I sixty-nined with another man, I
would usually suck my thumb while giving myself a hand job blow job. As my pleasure
increased, I would suck my thumb as deep into my mouth as I could, I would find myself
wishing there was something larger, warmer and more juicy in my mouth.
As I became more comfortable and accustomed to fantasizing gay sex, I began to
wonder if I might actually be willing to do it, should the opportunity arise. This caused
me to ask myself if the guy I might meet wanted to fuck me, would I let him? Blow jobs?
Probably yes. Anal sex? I couldn’t answer because I had never done that. In fact, I had
turned one guy down who did want to fuck me.
Another pregnant pause. I think one of the strangest things about sex is how we all
know we can hurt someone who asks to have sex with us but when we turn them down, it’s
personal. The person who does the asking has opened themselves up and feels rejection when
they are turned down. They wonder, “What’s wrong with me?” I know how I felt when my
advances toward my wife were rejected so many times that I stopped asking. It hurts.
With my experiences of being rejected and knowing what I felt, I decided I didn’t
want to find myself in a position where I might find a guy who wanted to have sex with me
and then rejected him because he wanted to fuck me. I wasn’t giving any thought to how I
might react if he wanted me to fuck him. I simply thought I would cross that bridge when
it came. But to be fucked, that was another thing altogether. This, naturally led me to do
more experiments.
The simplest way to experiment with getting fucked is to get some lubricant, use
the index finger and coat the entrance to the anus. I recommend you keep your nails cut
short and when preparing to push in, keep the pad of your finger up. In this fashion, you
can use your index finger as a tongue substitute while you draw it across the anus
opening. Then when you start to push in and explore, the pad of your finger tip can be
used to massage the prostrate gland, the most likely source for pleasure during anal sex.
The main recommendation I would make is to relax. You don’t want to just jab at
yourself. You want to take your time, feel around, explore a place you never explored
before. Your first surprise should be discovering that your sphincter muscle (round
muscles at the anus that normally keeps it closed) isn’t all that difficult to push past
and once past will actually act to pull you finger in. Once in the rectum, you’ll likely
be surprised by the sensations.
What sensations? The main sensation one usually experience is one of relaxation.
Having my finger in me puts me in a dreamy state. This is usually followed by me massaging
the upper inside of the rectum to include the prostrate gland. Some call this gland a
man’s G-spot.
Don’t expect to get an erection. If you had one before pushing your finger in, it
will probably be gone shortly after you enter. But here is the odd thing. There is a
sexual pleasure and you might find your penis will dribble some pre cum, especially if you
find yourself wanting to be fucked and this desire causes you to starting fucking yourself
with your finger.
I guess you could say this is where you have crossed the taboo bridge and say,
“What the hell” or “What the fuck. I might as well do something.”
When I’m finger fucking myself, I heighten the pleasure in two different ways. One
way is to let my placid penis rest on my abdomen and stroke/massage with my wrist as it
moves up and down by the action of my finger fucking me. The other way, and to me this is
the better way, is to have the head of the penis rest on my balls. In this fashion, me
banging me result in the head of the penis getting hit every time I push in. Believe it or
not, this can be maddingly pleasurable and sometime result in an orgasm even though the
penis is placid. The hot cum squirts out and bathes my anus and hand with its warmth.
When I don’t cum as a result of the finger fuck and my arm is too tired to continue
the action, I will usually be so desirous of coming that I’ll switch to masturbating in
the tried and true way.
If you do try finger fucking and are comfortable with it, and want to experiment
further, the next step is to try out a dildo on yourself. If you do, here you enter the
world of choice. Like Goldilocks, who want something not too big, not too small but just
right. You might buy one, look at it and wonder, “Will this really go into me? Will it
hurt?”
Lubrication is the key, along with taking it slow. As its tip presses against your
anus, you might think this will never go in. But a gentle pressure will succeed and just
as happened with your finger, your sphincter muscle will switch gears and pull it in. Take
your time. Don’t hurt yourself. Don’t push it in any further than you feel comfortable.
After a period of time of becoming familiar with the dildo and if the dildo you purchased
comes equipped with artificial testicles, you might surprise yourself one day when you
realize those artificial balls are touching your ass! What you first thought was too big
to enter, has now found its way all the way in!
Which is better? The finger or the dildo? I guess it’s a personal choice and might
depend on your mood. I find the finger works well enough and I think this is because I
prefer something human in me, as opposed to something artificial. This human versus
artificial situation could lead you, as it did me, to want to find a man who would put the
real thing in me. But before I was up to that, I decided to see what my reaction might be
when looking at naked men on the Internet. Would they turn me on?
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