"How I Became A Jerky Boy To My New Masturbatrix"
by
I'm a 50 year old single white male earning somewhere in the neighborhood of
$200,000.00 per year from a few good investments I made years ago. I live
alone in a very comfortable 4 bedroom rustic log cabin that is situated high
on a bluff overlooking one of the most beautiful rivers in this part of the
country. I own several classic cars, a stable full of racehorses and a
Cadillac Escalade that I drive on a daily basis. I also have a secret that
until recently I had taken great pains to conceal from the rest of the
world. That secret I have decided to reveal in this manner. I, a
successful businessman and a leading citizen (even if I do say so myself),
have been addicted to masturbation for the past 30 years. Not only
masturbation, but masturbation while wearing women's lingerie, stockings and
shoes and exhibiting myself publicly, yet discreetly, as I play nasty games
with my turned on body. A fact that I don't anticipate changing anytime
soon. Especially now that I have finally found the woman of my dreams. The
woman who has given me the courage to come out of the shadows and openly, if
not proudly, admit to the world that I am nothing more than her personal
Sissy Jerk-Off Boy and my sole purpose is to masturbate for her whenever and
however she wishes while dressed, or undressed, in whatever she directs. Be
it lingerie or leather. For she is my Queen, my Goddess, my Mistress. She
is my Masturbatrix.
It's still sometimes difficult for me to believe that only two short
weeks ago I was still living that bleak existence that I'd lived for such a
long, long time. Going about my day wearing my $800.00 suits with my nose in
the air and with that ridiculous snobbish attitude I was perhaps the world's
biggest hypocrite. After my day of acting as if I was somehow better than
everyone else I'd, at last, head to my favorite eatery to pick up something
for my supper. Then with bundles getting cold in the passenger's seat I'd
start for home.
Typically I'd only make it about six blocks to the mostly deserted
parking lot of an old bankrupt grocery. I'd discovered an excellent parking
spot there toward the back of the old building where neither me nor my
vehicle could be seen. Here I would shed the stresses of the day as I shed
my stiff business suit and put on the silky feminine attire I'd had hidden
in my auto's storage compartment all day. It's hard to describe the
combined feelings of relief, exuberance and arousal that washed over me the
instant I'd slide my feet into the leg holes of my pretty panties and
slowly pull them up my shaved legs. Or, while I meticulously rolled a pair
of expensive nylon stockings on and connected them to my sexy garter straps.
I loved it. I truly loved everything about it. The smooth, slick feeling
of the material hugging my body. The excitement of changing out of my
street clothes here in this open, somewhat hidden, but still public place.
Driving home in only my lingerie, nearly naked, and above all, playing with
my beautiful hard cock that would threaten to rip through the crotch panel
of my tiny panties as I'd slip my feet into the beautiful and sexy feminine
footwear I'd chosen for the day, and lay my man clothes on the back seat.
On the day that changed my life I was clad in a pink satin corset with
white trim at the boning, white lace garter belt, pink bikini panties, white
stockings and black high heeled sandals. No bra as I was afraid if I wore
a bra it could be too easily seen by the occupants of the other vehicles.
Besides, my nipples are extremely sensitive and I love teasing and toying
with them. They tingle so much when I'm aroused that they're nothing more
than hard little pebbles begging for my touch. Just rubbing them lightly
with my open palms never fails to cause a steady flow of pre-cum to begin
spilling from my cock and almost always is the catalyst for another one of
my multiple masturbations during the course of any given day, afternoon,
evening or night. As a matter of fact, it was just that very thing that
caused me to first meet and experience my now Masturbatrix.
I had just finished changing at my parking lot spot and was leaving,
backing my Escalade out of my perceived seclusion when in my rearview I saw
her standing directly behind me, blocking my only way out. She was dressed
in boots, black fish net stockings, short blue jean cut offs and a tight
halter, on the front of which was emblazoned "BITCH" in bold pink letters.
Her face and figure appeared to be quite stunning from what I could see in
the mirror. On the ground beside her sat a black overnight type bag and in
her hand was an envelope of some sort that she kept slapping against her
thigh as she stood staring back at me in my mirror. She was obviously
waiting for me to stop my vehicle. I supposed so she could approach my
driver's side window because when I did, she did. My excitement at being
actually seen dressed as I was by this beautiful, strange, woman made my
cock swell to extreme proportions. In spite of my combined feeling of fear
at her reaction and the excitement of being seen, I was also decidedly
turned on and couldn't resist my urge to lightly brush my rock hard nipples
with my palms before she arrived at my window. The feeling was like no
other before it in intensity and stimulation and I was suddenly and
unexpectedly cumming. Hot white ropes of sticky sperm erupted from my hard
cock and soaked the crotch of my panties. An ever increasingly large circle
spread from the top of the tent my jerking erection was causing , soaking
the tiny garment more and more completely with each passing second. My
throbbing erection was also causing the panties' delicate waistband to be
pulled away from my body which left a clear and unobstructed view of my
cleanly shaven abdomen and the root of my thick, wet cock.
Glancing in my rearview mirror it was obvious there was no time to clean
up or even hide my mess. I was blushing bright red, out of breath,
mortified and strangely satisfied when she arrived at my driver's window and
stepped up close. I was too embarrassed to look at her as I imagined all
that she must be seeing right then. Her loud knock on the window glass
caused me to turn my eyes her way however, and when I did I saw that she
wasn't looking at me either. Well, I mean she was looking at me, but just
not at my face. Her intent stare was firmly locked on my crotch and
everything there was to see down there. My nylon encased legs, my tiny pink
panties with their load of fresh cum, my still jerking hard-on and my
meticulously clean shaven body. As if in some sort of hypnotic trance she
motioned for me to roll down my window with her thumb, never glancing away
from her focal point on my crotch for a second.
I hesitatingly complied to some extent and lowered the glass between us
about 6 inches. "Do you like it?" I boldly asked. Her eyes remained on my
hard on as she answered that she'd seen it all before. "I just never knew
you were so big," she added, finally raising her eyes to meet mine.
"You're a kinky little rich boy aren't you Darlin'." she said smiling as she
passed the envelope she was carrying in to me through my lowered window.
Cautiously I took it from her and opened it. Inside I found an
extensive photo documentation of none other than me in various stages of
dress and undress as I was changing from my business suits into my lingerie
here in my "secret and secluded" spot. There were photos from as far back
as six months and spanning what appeared to be each and every visit I'd made
here---which were numerous. So that's what she's up to, I thought.
Blackmail! "I think maybe you'd better get in," I said calmly. "Yes, so
do I," she smiled and promptly circled my vehicle to climb into my
passenger's seat. I barely had time to transfer my supper bags into the
back floorboard before she was sitting there staring at me.
We both just sat for a very long moment eyeing each other. She
obviously taking in my naked body clad in the feminine attire, and me
attempting to overcome my shock and embarrassment at her substantial beauty,
which I slowly admired from head to toe and back. "So," she said looking
me in the eyes. "You like the pictures?" Picking up the stack from my
console between us I slowly looked through them again before putting them
back in the envelope and tossing them in her lap. "How much?" I asked,
contempt dripping from my voice. Or, at least as much contempt as I could
manage considering my situation.
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"How much what?" she asked, her eyes open wide in mock surprise.
"Money!" I loudly responded. "How much money do you want to make you and
your pictures go away forever?" Removing the pictures from the envelope she
began slowly looking at them one at a time, a broad smile on her face that
she renewed with each consecutive print. "Money?" she finally asked. "I
don't want money. And, I'm insulted that you'd think a monetary value could
be put on all of my hard work." she concluded, laying the pictures in her
lap and raising her eyes to mine. "No," she continued "I've got something
else in mind entirely." Then added, "My, but you do love to play dress up.
Don't you?" She didn't wait for my answer. "Well, of course you do," she
quickly went on..... "Just look at how wet and sticky your little panties
are. You really should be punished for that you know?" Then again looked
into my eyes and smiled. "And I plan to be the one who administers that
punishment," she trailed off into a near whisper and I had to struggle to
hear what she'd said. 'What audacity', I thought.
"First of all," I began, "my personal behavior is really none of your
business. And secondly, Just what will it take to get rid of you!" I
covered my now shrinking cock with both hands and gave her a hard stare
directly into her big brown eyes.
"Well," she started calmly, "It's like this,....... You can't! You
see I lost my job about six months ago and since then I've been struggling
to keep up with my rent and bills. To say nothing of my social life falling
into total ruin,..........Then one day when I was almost at my wits end I
happened to look out of my bedroom window and what did I see but you, one of
the upper crust of our little society, hiding behind this old building
acting real suspicious. Needless to say, you captured my attention. So I
started to seriously watch you then. I saw you look around to see if anyone
could see you. You didn't see me, but I saw you when you started to take
off all of your clothes. Now, a fire couldn't of kept me from watching,
and I even decided to go one better as I hurried and got my camera from my
dresser drawer getting back to my window just in time to see you putting on
women's lingerie. That's when I started taking pictures. I didn't know
what I would do with them yet, but I figured something would come to me
sooner or later. And, as you'll soon find out, it did. Also, I discovered
I got very turned on whenever I watched your little show and so I started
watching for you to come back. When you did, I took more pictures. Only
now I was taking my clothes off when you showed up as well, and taking my
pictures with one hand while I played with myself with the other. Your
little performances really made me hot and I could hardly wait each time to
get the film developed and the pictures back so I could masturbate looking
at them and fantasize about having a rich boy like you as my personal, sissy
slave. That's when I said to myself..."Why Not?" and worked out this idea
that would solve all of my problems. You wanna hear what it is?" she asked
looking at me with that same smile.
I was more than a little afraid to hear what her devious mind had
conjured up, but I had no choice. "Yes, of course I do," I said with as
much bravado as I had in me at that moment. "Tell me......What's your great
big idea?"
"OH! It's no longer an idea, you understand." she told me in earnest.
"Now it's a plan." She sat for a moment to let her statement soak in then
continued. "Now here's what's going to happen. You're going to take me
home to live with you in your house. Expense free." I started to protest
but she stopped me saying; "Before you tell me some lie like you're married
or something else as ridiculous you should know that I've done my homework
on you and probably know more about you than your mother does, ..........so
you just sit there quietly and listen. Okay?" She sounded so authoritative
and stern that I was mesmerized, and meekly shrank back into my seat and did
as I was told.
"As I was saying," she continued. "I'm coming to live with you at your
house at no cost to me. You will see to all my needs such as food and
clothing and you will provide me with any money I ask for. As for you,
You'll be expected to dress and behave as I instruct, to be at my disposal
whenever I call, (Night or day, morning, noon, evening or midnight) and to
serve me in all ways. In other words, you are to become my personal slave
in every possible way. Any indiscretion will be cause to suffer my
punishment. And, to avoid the personal embarrassment you'd have to endure
if these pictures ever got out, you WILL comply with everything. You are to
start immediately. Do you understand?" When I started to speak and respond
she quickly leaned across my console and delivered a stinging slap across my
face. "Did I give you permission to speak?" she questioned sternly. When I
again started to respond she slapped me again............harder. I meekly
lowered my eyes and, rubbing my stinging cheek, slowly shook my head to
indicate that NO, I hadn't received her permission to speak.
"That's more like it," she said, gloating. Then continuing she said;
"You will always refer to me as Mistress or Madam.......That is, of course,
when I allow you to speak. Otherwise you will only listen and obey. Just
like you're doing now. Do you understand, slave?" she asked with a smirk.
This time however I immediately nodded, but barely heard the question as my
mind was going at least a hundred miles an hour considering the
possibilities her proposal would offer me. I'd often thought and fantasized
about what it would be like to serve a dominant woman as her sissy slave.
Being ordered to perform every nasty notion that she conceived, being
forced to dress in lingerie when in her presence. Perhaps being commanded
to perform kinky masturbation demonstrations for her pleasure while using my
tongue to bring her to orgasm after orgasm. I needed to talk to her about
it, to reach a mutual understanding with her, to impress upon her the
importance of allowing me to fulfill my secret kinks and needs and implement
them into my service of her. I just knew that if I could express my side we
could come to a mutually satisfying solution in which both of us could have
our needs well met. I just needed the opportunity to speak to her. That's
all.
I knew that she had continued to talk to me about how she felt I should
behave, but I really had no idea what she had said, exactly. I wasn't
particularly concerned about it either, since I knew without doubt that if I
wanted it I could easily have her disposed of without anybody being the
wiser. For the moment however I decided to let her believe she was getting
her way and she had me over a barrel. Perhaps she might prove to be an
entertaining distraction for awhile, I thought. It was surely worth a try
anyway. It was this logic that made me decide not to make any demands on
her as to what it would take to satisfy me and therefore make me happy to
continue in her perceived BDSM relationship. Let's just see what she comes
up with on her own, I thought. No need to give her any ideas. Maybe she'll
even make me happy on her own.
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"So are you ready to obey me now?" I heard her ask me when I again
tuned into her words. I nodded. "Wonderful," she exclaimed. "Show me your
cock, slave," was her first commanded. Immediately I stretched the
waistband of my panties down under my balls and quickly brought my hands
back up out of the way in order to present her with an unobstructed and
clear view of my, once again, hardening cock. Just as she had requested.
"Make it hard," was her next order, and I instantly began to jerk
myself like I'd done so many times before, soon coaxing my cock to another
full erection for her. "Nice," she complimented me. "Now take those
panties off," she told me next. "I want to watch you play with your
asshole too.............With this!" she added, and pulled a large cock
shaped vibrator from the bag she'd brought. As I followed her order and
pulled the tight, cum soaked panties down my hairless legs and over my feet
I watched her suck the entire vibe into her mouth and down her throat,
leaving a thick coating of saliva on it before handing it to me. Although I
did enjoy playing with my ass occasionally and had used butt plugs in the
past, I'd never tried anything as big or as long as the vibrating dildo she
was now holding. The uncertainty I felt must've shown on my face because,
( I didn't even know her name), took one look at me and said; "Oh don't
worry about it. It'll fit alright. Just relax and let your asshole stretch
around it...........Of course," she continued, "if you don't think you can
get it in,.......I can do it for you." That was all the encouragement I
needed and set my mind and asshole to doing it or bust, (not literally I
hoped).
Taking the oversized rubber cock from her I slid my ass to the very edge
of my seat to allow me to get to my asshole unobstructed and holding the
vibe in my right hand pushed it's head between my cheeks. I spread my legs
as far apart as I could as I massaged the rim of my asshole with the soft
tip of the dildo and lined it up for the grand entry. Gritting my teeth and
holding my breath I then began slowly pushing inward with both hands holding
the vibe by it's base, and to my relief felt the head open my rear hole and
pop past my sphincter and into my ass canal. It hurt a little, but nothing
I couldn't stand, so I consciously told myself to keep my asshole relaxed
and resumed pushing with my hands, causing the dildo to slip deeper and
deeper, an inch at a time. Finally, after allot of concentration on my part
to keep my asshole relaxed in spite of it being stretched beyond all
previous limits, I felt my hands come in contact with my spread asscheeks
and my fingers holding the dildo felt the stretched rim of my invaded hole.
Taking a few deep breaths and again concentrating on keeping my ass
relaxed, I began a slow but steady in and out motion, fucking myself in the
deepest realms of my anal canal and allowing myself to get accustomed to the
sensations. "He-He-He!" My future Masturbatrix squealed and clapped her
hands together. "I knew you could do it. See? I told you........Now turn
towards me so I can watch you fuck yourself with it!"
Struggling to hold the thing in my ass, I twisted my body around to
face her. Placing my right foot on top of her seat and pressing my toes
against her headrest, I leaned back against my door and rocked my hips
upward until she had a clear and unobstructed view straight at my asshole
and the monster dildo that was fucking it. By this time I'd gotten rather
used to the stretched state of my butt, either that or I'd become numb back
there as it was somewhat easier to saw the vibe's girth in and out. With
less resistance I could maneuver the thing with one hand, so taking a firm
grip of it's base with my left hand, I let go with my right so I could
return to stroking my amazingly hard and incredibly needful cock. My one
girl audience seemed pleased with my move and stopped massaging the wet spot
between the legs of her shorts to very quickly unfasten the buttons holding
them closed and shove them down her shapely, tanned thighs and past her
knees. Moaning encouragement to me she began a vicious assault on her
neatly trimmed and newly exposed pink pussy with both of her slender hands.
Watching her as she publicly played with her wet cunt combined with the
incredible sensations I was experiencing through the simultaneous
stimulation of both my ass and my cock was seriously speeding me toward a
very powerful orgasm and one I knew I couldn't keep from happening - even if
I wanted to. I did, however, want to hold out at least until my
masturbation mate had achieved her own orgasm, perhaps even cumming together
in a mutual explosion of ecstasy. That wasn't going to be an easy task
though. Not unless I either backed off of my own play or found a way to
speed her up---So....I decided to try to do both.
Taking notice of how totally she was being consumed by her lust I
decided to take my chances and try to get away with some hot, verbal
encouragement of her, in an attempt to build her excitement to the boiling
point, hopefully propelling her past her orgasm's point of no return. As
for myself I had eased back on my cock stroking considerably and was now
doing more imitation stroking to keep up appearances than the real thing.
By gripping my cock at it's base with my pinkie finger and the heel of my
hand I'd managed to turn my own orgasm fires down for the moment, which gave
me be just enough time to turn her up...........I hoped!
Beginning with a lustful groan and a softly moaned compliment to my
lovely companion acknowledging her ingenious plan to survive on my money and
telling her how incredibly stretched and stuffed my ass felt I rolled my
hips a little higher so I'd capture her attention for the upcoming visual
portion of my quest. I had pulled the thing about 3 quarters of the way out
of me when I saw her eyes lock on the action. I didn't waste a split second
before adding my narrative to it.
"My Mistress loves to see how her huge cock stretches her bitch's man
cunt. Doesn't she?" I moaned through gritted teeth. "OOooooooo!" was her
only response, but it was enough to encourage me into continuing. "Oh God!"
I cried as I started shoving it back in. "It's so fucking big and thick."
I was giving an Oscar winning performance as I tightened the muscles in my
arm and gave her the impression that it was taking everything I had just to
be able to force the monster sized rubber cock back into my asshole when in
reality it was taking all I had just to be able to keep my asshole from
sucking it back in of it's own accord.
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Suddenly, with about two thirds of her dildo wedged up my ass it
stopped with a jerk, my rectal muscles refusing to let it proceed any
further in any direction. "Umphhhhhhhhh!" I groaned as I used all the force
of my left arm to push it in another inch. Letting go of my, once again,
very excited cock I leaned forward so I was able to reach between my legs
with both hands. Gripping the dildo's base with my fingers interlaced I
groaned, "Nooooooooo!.............I wanted to take it all for my Mistress!
Umphhhhhhhhh," I grunted again as I managed to push a little more rubber
into my ass. Her eyes were nearly glazed over as she stared hypnotized at
me feeding inch after agonizing inch of the ball bat sized phallus into my
aching anal canal. I took immediate advantage of it.
"Oh yes! Look at it Mistress," I groaned "Look how your slave bitch
hurts her ass for you.............Watch me push it all the way in for you my
Beautiful Mistress!..............Watch how far it stretches my poor asshole,
Mistress!" I groaned a little louder, but this time it was for a different
reason. In my determination to achieve success with implanting the dildo in
my ass I kept leaning my upper body closer and closer to my crotch for more
and more leverage. However, on my last lean my very excited, turgid cock
had come in contact with the slick satin of my corset causing my cock to
jerk and jump for joy and me to raise the volume of my voice suddenly. A
few quick practice humps with my hips and I knew I was onto something.
My actions became almost animated as I began furiously humping my hips
up and down while pulling myself up with my hands on the dildo and thusly
putting greater and greater pressure against my cock as it frantically
fucked up against the folds in my satin corset and simultaneously pushing
the dildo steadily inward toward total insertion.
Mistress's orgasm was progressing right on schedule as was evidenced by
what began as a low moan deep in her toes and was now to a much louder level
straight from her pussy and also by the way she was now assaulting her clit
with such force I was afraid she might tear it off. With her other hand she
was literally pounding four fingers into her gaping cunt hole and doing it
so forcefully each down stroke that she made caused a loud slapping sound
when the heel of her hand made contact with her saturated cunt lips.
As her moans continued to crescendo and her smell of arousal permeated
the air in my Escalade with it's heady thickness, I felt as if I was about
to lose my mind to the extremities of my arousal. I could feel my own
saliva slowly cascading down my chest as it flowed from my drooling mouth.
I was hunching my cock against my corset now in short, rapid jerks as I hung
sexually suspended on the verge of a climax that was already taking my
breath away. All I needed was one final push. To catch my cock on the
right fold. To tweak my stone hard nipples with the right twist or pinch
or pull. I was desperate for any one of the vast array of stimulation it
would take to send me over the edge of ecstasy, when Mistress suddenly
provided it for me.
"OH GOD!.......OH GOD!.......OH GODAMN!" she shouted at the top of her
lungs when the first waves of her own orgasm washed over her. As she began
to convulse wildly in my passenger's seat I gave a Herculean effort to pull
myself up one last time and when I did the added pressure exerted by my
hands on the base of the dildo caused it to slip and it's final few inches
buried firmly and flush into my stretched asshole. That was the final
straw, and I was suddenly cumming. Long ropes of my white, hot semen flew
randomly through the cab of my Caddy sticking to everything it came in
contact with, yet still it showed no signs of slowing. I came for what I'm
positive was at least a full minute, my cock pumping out gob upon heavy gob
of thick white cum that both soaked and exhausted me.
Sweat rolled down my flushed face in rivers as every muscle in my
spent body quivered and spasm. My cock still swelled and jerked as if still
ejaculating cum, although my balls had given up the last of their supply and
now hung loosely atop the dildo that was still in my ass. Through foggy eyes
I at last focused on my new Mistress, still gasping for breath in the
passenger's seat. "Thank you, Mistress," I said in between breaths. "That
was the most incredibly amazing orgasm I've ever experienced. She smiled
and wagged the index finger of her right hand at me until she could speak.
"I thought I told you not to speak," she admonished, a good natured
tone in her voice. "Now pull that cock out of your ass and get busy
cleaning up this mess ............with your tongue," she commanded. "Me
first!" she said while lifting my console up into it's place in my seatback
and indicating by a sweep of her hand exactly where she wanted me.
Moving as quickly as I could I eased the monstrous cock from my sore
asshole with a final pop and turned to lay my head in her lap and began
tonguing up her abundant overflow of love juices smeared over her thighs
before concentrating my attentions on thoroughly cleaning her succulent
cunt. When I had licked her to a renewed state of arousal she took a
handful of my hair and pulled my face from between her legs.
"That'll do for now, slave," she said in earnest. "Now lick up your
mess and drive us home............quickly," she added scooping up a finger
full of my cum from the seat and feeding it to me. This time I happily did
exactly as I was told.
Since then She has completely redone my wardrobe with a vast array of
beautiful lingerie that I am required to wear at all times. When in the
house it is the only thing I wear and when outside at my business I wear it
under my suits. I'm also required to always wear one of the many cock and
ball harnesses She has given me, no matter when or where I am or what I am
doing. She has proved incredibly ingenious at inventing new and different
ways for me to masturbate for her as well as unique and exciting ways to
feed my need for exhibitionism. We often host parties for other couples of
like minded persuasion where us jerky boys take turns either serving the
Mistresses or we are stationed at various locations around the house to
stand and masturbate for everyone's entertainment. Of course we are also
required to be of sexual service to whoever has received permission from our
individual Mistresses for us to do so.
All in all, I am the happiest I have ever been and with any luck
Mistress Natalie (I found out what her name is) will remain with me forever.
..............Oh yes! As for those pictures. They are now each beautifully
custom framed and hang proudly on the walls of our plushy furnished play
room for all to see. And, I am extremely proud of each and every one of
them. "Thank you Mistress Natalie! From the bottom of my wonderfully sore
cock! You are truly my all time best fantasy come to life."
- The End -
[Note: this story is protected by international copyright law,
all rights not expressly waived are reserved by its author.]
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