Part 1-
There is a lovely Lady who resides in the New York City area that I met a couple of years ago
through an internet chat room. Quite ordinary things were discussed including travel and even the weather. After
a while I asked Her not to be put off by my rather graphic profile which shows my true self - myself nude and my pronouncements
that I am a completely submissive male devoted to pleasing and entertaining Ladies. She replied that She was not offended
and rather enjoyed seeing me in various states of being tormented.
The pictures included my balls being tied and my very strong tendency to cross-dress and be
simply a plaything for whatever Lady may wish to amuse Herself. We finally met and She has developed into a wonderful
dominant Lady who seems to relish tormenting me. This report is about our most recent meeting.
Mistress C instructed me to proceed promptly to Her residence. I obeyed and felt a box
of chocolates might be an appropriate simple gift to show my appreciation for Her training. It had been a few months
since She had last seen me so we chatted a few minutes. She is quite a lovely Lady, a good conversationalist, and She
enjoys a marvelous sense of humor.
After a few minutes She said simply, "strip". I did so immediately. I know one thing
that would annoy a Lady is to leave one’s things in an untidy manner, so I did my best to neatly stack my things out
of the way. I now was wearing just my lovely panties which were quite small.
My little dicklette was constrained into a very small space under the smooth fabric, but it
would occasionally try to peek out and play "peek-a-boo". My testicles, too, were being quite naughty. They would
sometimes droop beneath the panties. My ample and plump ass was poorly covered.
Mistress noticed this and said "My, My, you must control your clittie better than that. We
will work on it."
I kneeled on the floor before Her. She commanded me to warm some coffee for Her so I immediately
complied with Her order. She relaxed on the sofa and told me to prepare myself. I was told to find my little bag
of frilly things, find the enema and go.
I cleansed and cleansed. I wanted to be pristine and pure for my training and to show my
devotion and respect. Mistress came in to the bathroom for a few minutes to gauge my progress and I was so happy She
approved. I was so nervous. I knew She may wish to test my slut training and I so wanted my male vagina to be ready
in case She did.
Finally, I entered the living room and kneeled before Her. She gave my ass a couple of
swats and I was told to put the dog collar on. She attached the chain. She then inspected Her property. I was
told to stand and make a circle. My clittie dangled before Her amusingly. I had made sure my balls were hair-free. Mistress
likes Her balls that way. She teasingly pulled them away from the shaft and inspected them. I was then told to warm
some more coffee for Her. She gave me another swat and said, "now, slave."
When I returned She had prepared the coffee table with Her favorite devices. First, Mistress
placed each ball within a noose and tied the sac and penis tightly. The sensation was a bit uncomfortable I must admit,
but it is my duty to perform for Mistress.
My clittie began to engorge itself. I was so pleased that it stood at attention in respect
for Her. It simultaneously showed respect and its ugly head for Her amusement. She tightly squeezed the two ping
pong balls and tested their elasticity. But I had displeased Her a bit. She did not like the undisciplined way the
penis was bobbing around. So She tied a black belt around my waist and then tied the penis to it.
Then I was told to get on my knees and elbows. I heard the sound of latex gloves smacking
as She donned them. Mistress C commanded me to spread very wide and accept my fate. This was it. Mistress expected
my vagina to be ready. So I tried my best to relax and accept my destiny. I felt Mistress run Her royal fingers
up and down my crack.
Finally, the inevitable happened. She inserted a finger slowly into my deep hole. She
was testing because I knew much more was to come. As She inserted a second finger and then a third She began to pump
me in and out. With Her other hand She massaged my perineum and the hidden prostate.
"You are such a slut, aren’t you, slave? You’re going to get it today. Beg
for it."
I replied, "oh yes, Ma’am, thank You. I am a slut. Thank You for fucking me. Please
prepare me so I can become a good whore for You, Ma’am."
She gave me several spanks. I felt my derriere warm. She removed Her fingers. Soon
a new object entered me. I felt it slide slowly past my little puckerhole and then meet a bit of resistance at my sphincter.
"Take it now, slave. Take it deep. Spread wider."
The dildo made me feel like I would be split in two. Her assault was relentless, but I
know it’s what I must have. How could I become a good slave, cocksucker, and whore if I couldn’t take Mistress
C’s butt plugs and dildos? If She had a party, how could I please Her friends? No, this training was for my
own benefit. If I am to be a party favor, I must be ready and well trained.
In utter devotion the plug entered me entirely. "Good boi. That’s my slut." Relief
and pride consumed me. I was pleasing the Mistress. "But you must be punished for that bit of resistance. You
shall have to be spanked. Now keep the plug in."
"I’m so sorry, Ma’am. I didn’t mean to be so naughty."
Mistress C then delivered several smacks to my upturned ass. "Ow Ow Ow... oh my oh my...
I’m sorry, Mistress. Ew Ew Ew " It was so excruciating,stinging and I could feel my butt warm and turn red. She
continued with Her spanking. I felt I could wail just like a little sissy- which is what I am, of course!
Then it happened. I lost control and the butt plug loosened and dangled out. I tried
so hard to hold it in. But it was no use. It plunked down onto Mistress C’s carpet. Just two words came
from Her: "stand up."
"Stand at attention." She then blindfolded me and led me to Her desk. "Now lean over
and place your chest on the desk. You shall receive punishment." She thrust the plug deeply into me and I screamed
a little scream while I was bent over at 90 degrees. SMACK!!
This was a new sensation. Mistress was using Her cat-o-nine tails I would later learn. Each
cheek received it’s penance. It was impossible to know where She would strike next. Even my balls were not
immune.
She swished the cruel device up and inevitably one or both balls would feel a sting. She
placed Her first finger and thumb around the little testes and pulled them back. WHACK. WHACK. SMACK.
Then I felt Her strap. My butt cheeks felt like they would blister. But they didn’t. Mistress
is an expert at delivering a punishment. Surely Her neighbors heard everything. I whimpered, cried, and truly regretted
my mistake. "Oh Mistress. I am so sorry. OW. OW!!" I breathed my heartfelt penance between blows. "Thank
You, Mistress. I know I need this."
"Yes you do"... Finally it ended. I was just a whimpering heap collapsed on the desk, my
eyes covered, my vagina exposed. I knew what would come next.
"Now spread and spread wide. Beg for your destiny." My red ass was being cooled by
something cold. She lightly massaged my ass cheeks and gently rubbed my perineum, the area under my balls. "You
know when you displease me what happens. You know you must accept what is to become a part of you- that you must hold
the dildo."
"I’m sorry, Mistress. I’ll do better. I promise." The blindfold was still
in place.
"Now prepare yourself." I felt the penis head slide in ever so slowly. It was exquisite. She
tested me. In and out, in and out, just a little. I began to coo and moan a little. I began a little rhythm
to meet Her gentle thrusts. "Now deeper." I froze. It was happening.
The penis slid deeper still into my womanhood, or should I say faghood? "Good slut, good
baby." My breaths were getting deep and then shallow. I could feel my male vagina being completely violated. She
would go deep and increase the tempo of Her thrusts. I met every one. Then She would tease my prostate. The
penis head tickled and I nearly shuddered with submissive bliss.
This was my destiny-to become a whore for Mistress. She was wearing Her strap on, the divine
device for taking me, and taking me all the way. "I will take you to a club and all the Ladies there will enjoy you. You
will assist each one. Every Woman should penetrate you."
"Yes Mistress, oh yes Mistress, oh yes Mistress."
To be continued.....