Date: Thu, 12 Jan 2017 20:18:31 -0600
From: Your old friend Tappy <tappymcwidestance@gmail.com>
Subject: Decision Tree Chapter 04

Decision Tree Ð Chapter 04
By
Tappy McWidestance

I was on pins and needles wondering what my punishment would be. I had cum
without permission, although I had been setup to fail. I knew Sir had done
that just as an excuse to further my training with some negative
reinforcement. I wondered if it would really be that negative though. I had
read a lot about spanking and it seems like many women find it helps get
them into subspace where they can really let themselves go. I always felt
only playing with James on Fridays was punishment. If a spanking helped
arouse me that would hardly be a bad thing.

As I told you before, James had setup an Amazon wish list where he put toys
he wanted me to buy. The strange thing was we hadn't used any of them
yet. He had me buy four leather cuffs, a Hitachi Wand (I was dying to try
that one out) a better webcam, nipple clamps, a flogger and a riding
crop. I assumed he had my training planned well in advance and that I would
soon be ordered to cuff myself and then somehow hit myself with the flogger
or crop. I anticipated that he wanted to watch as well with a better
picture than the webcam on my laptop provided. I was surprised when I got
an email from him late in the day on Wednesday with different instructions.

I was to go to a specific adult bookstore on Washington Street just west of
the Loop where I worked. It wasn't far, but it screwed up my taking the
train home that night. I suppose I could grab an Uber, although I would
have to find someplace respectable nearby to give as my destination. At the
store I was to buy a paddle. It was to be leather covered, firm and have
some weight to it. The instructions said to pick up several paddles for
comparison and I would understand what he meant by having some weight. I
was also to buy an anal training kit and a collar. He told me not to spend
much on the collar, as it was not meant to show commitment but was more for
play at this point. He told me he would purchase a better collar himself if
and when he chose to collar me. He told me to take a picture of what I
bought and to send it to him. He also told me to be online at 9pm.

Walking into the store by myself was a little nerve wracking. The place
wasn't a seedy dump, but it wasn't an upscale boutique either. I didn't see
any other women. That made me nervous and more than a little
embarrassed. Of course the clerk asked if I needed help. I doubt he asked
the guys that. But I am sure he doesn't get many beautiful women in
tailored business suits walking through the door, so I should have expected
a bit of attention. I tried to sound calm as I politely told him I was just
browsing. I didn't want him to know I had a shopping list. He too was
polite and told me if I needed anything (yes he stressed the word anything)
to let him know. I just nodded and started looking for the paddles.

They didn't have a big selection, but I quickly understood what Sir meant
by picking one with some weight. They had long narrow paddles that were
very heavy, small round ones that looked like ping pong paddles and weight
about as much and kind of medium sized ones. I hit my hand with both the
small and medium paddles. The small paddle made a big noise, but didn't
really sting. The medium paddle had a less impressive thud sound, but hurt
much more. I couldn't really use the large paddle to hit my hand and I
didn't want to ask for a volunteer to use it to hit my butt, but looking at
the construction of it, I am sure the added weight would mean a much higher
pain factor. I decided Sir meant for me to buy the medium paddle. It was
big enough to sting, but not so big that I couldn't use it on myself if
that was what he had in mind. Looking up after I made my decision, I
discovered I had a small audience that had been watching. Again, I suppose
that was to be expected. I only hoped they would keep their distance. Or
did I.

The collars were in the same section. Again they didn't have much of a
selection. This store seemed to focus on videos. I did notice some guys
going into a back hallway so I deduced they also had video booths. My pussy
was wet from hitting my palm with the paddle and from touching the leather
collars and imagining them around my neck, but I didn't dare go into a
private area by myself. I quickly chose a one-inch thick collar with a
d-ring in front. It was faux leather and cheaply constructed, but
inexpensive and I figured it would do for now.

Surprisingly they had a better selection of vibrators, dildos and anal
plugs. It was almost a disappointment because I was a bit bewildered by the
selection. Since I didn't have a lot of choice on the paddle and collar, it
was easy to pick one. But unfortunately, as my husband always complains, I
need to do my research and it takes me a long time to choose something when
we are shopping. In this context, that meant picking up each plug package
and most of the vibrators too. Sir didn't say I couldn't get a special
treat for myself. I could feel the eyes of the men in the store watching
me. I don't know why I found that humiliating since they were obviously as
perverted as me. Well maybe not as perverted, but certainly they were no
better than me. I really wasn't sure what Sir wanted me to buy and I almost
convinced myself to ask for help (I was trying to avoid that at all cost)
but then I spotted a combo product in a clamshell plastic package on the
bottom shelf that was almost hidden. Before I picked it up I knew it was
what Sir and sent me to acquire.

The package contained three different butt plus from pretty tiny (that's no
big deal) to medium (that's going to hurt) to large (what the fuck? That's
not going in my ass) sizes. It looked like they were rubber or some kind of
extruded plastic. I had been looking at glass ones. They looked prettier
and I figured would clean easier, but the words "anal training kit" on a
piece of paper inside the plastic tipped me off that this was the product
for me. I thought about buying one of the pretty glass ones too, but I
decided to wait for another day. If the training kit was a disaster, I
didn't want to have wasted money on a high quality plug too. My face was
beet red by the time I took my collection to the counter to pay. I wanted
nothing more than to get out of there in a hurry and get home. The clerk
asked for my ID since I paid with my debit card. I was worried about him
seeing my address, but I handed him my driver's license anyway so I could
get moving.

Fortunately it didn't take long for an Uber driver to pick me up. My new
toys were in a non-descript bag and I had the driver pick me up from a
restaurant across the street. My ruse fooled him, although all the way back
to the apartment I wanted to pull out my collar and the paddle and feel
their texture. I wanted to know what the collar felt like around my neck
and I wanted to know what the paddle felt like against my soft skin. But I
couldn't indulge myself. I just let the package sit next to me on the back
seat. I kept calling to me to open it, but all I could do was slowly and
quietly rub my thighs together. As we got closer and closer to my place, I
got more and more excited. I couldn't wait for John to leave for work so I
could get online.

At 9pm sharp I logged into the chat room. I was dressed, as I had learned
to be, ready in case Sir wanted me to turn on my camera. I was wearing a
garter belt, stockings and stiletto heels. I wasn't wearing anything else
and my nipples, as usual, were rock hard and aching to be touched. I hoped
he would let me. Oh, and yes I was wet. I hoped he would let me touch my
pussy too.

I could tell as soon as we connected by cam that although he told me I
needed to be punished for cumming without permission, he was really pleased
with how it happened. I wished he would stop using the voice manipulation
so I could hear his real voice and his tone, but I sensed a level of
playfulness this time that I had not detected in our previous chats. Maybe
he figured out from my trip to the mall that I really would follow his
instructions no matter what. Whether that was true or I was just wishing it
were true didn't matter. I was soon kneeling on my chair with my ass facing
the camera. I was leaning over the back of the chair trying not to spin
around. My arms were reached behind me with my hands spreading my ass
cheeks apart. Given that I had bought the anal kit, I assumed he was
training me to be comfortable showing my secret hole.

He had me hold that position for several minutes. He told me his other sub
was kneeling in front of him doing the same thing. He told me he was going
to spank her while I paddled myself. I was jealous, of course, that he was
playing with another woman. It was worse that he was doing it while he was
playing with me. But subs don't get the luxury of worrying about those
details. I just tried to stay still until he was ready for me to do
something else. In a way I felt blessed that I was getting any of his time
on a Wednesday instead of having to wait until Friday. After a few minutes
of agonizing anticipation, he was ready to begin.

"I want you to lightly spank both your ass cheeks," he commanded me. "Start
softly, move around covering your entire ass and gradually hit yourself
harder."

I heard him begin to slap his real life slave. His voice distorter messed
with the sound, I could tell from how hard he wanted me to spank myself and
I did my best to mimic what I heard. His slave wasn't making any sound
yet. I understood, as I wasn't experiencing any real pain. Sir explained
that a light spanking served not to punish, but to increase the blood flow
to my backside. He said warming up a sub first prevented bruising and
allowed for a higher pain tolerance in the long run. I didn't know if that
was true. I only knew my girl juice was running down the inside of my thigh
because I was so aroused exposing myself to him. And to her, for that
matter, if she was being allowed to see my broadcast.

After he told me her ass was pink, he instructed me to go to a mirror and
check my own. I knew he could already tell from the webcam if I was
prepared to move to the next phase of my punishment, but I guess he wanted
me to see for myself. As I stood in front of the bathroom mirror I kept
twirling around to view my ass from different angles. I must admit I though
my slightly red bottom looked sexy framed by my black fishnet stockings. I
hurried back to the computer and retook my position.

Sir had me spank myself harder now, but I don't think I matched his assault
on his sub. That isn't to say I didn't try, but I don't think you can hit
yourself that forcefully. I always slowed down just a bit before
impact. After a few minutes I began to feel warmth spread through my butt
and to my clit. I'd read that a spanking could have a very arousing effect
and now I was starting to experience it. It was at this point that he
ordered me to switch to the paddle. He also told me his sub was going to
watch.

If it is a challenge to spank yourself hard enough with your hand, that
issue goes away with the paddle. Maybe it is because it is an indirect
contact. Maybe because I was so turned on and wanted to please James. Maybe
it was the thought of another sub watching me punish myself as part of her
training. No matter the reason, I was perfectly fine walloping myself. The
first stroke stung like I'd never felt before. But it also made my pussy
twitch. The second impact was much like the first. And I liked it.

Sir's sub reminded me to count out loud even though I had not her doing the
same. I wasn't about to argue. I assumed he had a target number in mind,
but I didn't ask what it might be. I was going to prove to myself and to
them, that I was a good girl and could follow instructions. I was skeptical
that warming my backside up slowly would prevent bruising. I was hitting
myself too hard, I told myself. I wasn't sure how I would explain to John
how my butt became injured. I guess would have to have to go back to
blowjobs and missionary for a while.

The warmth from my butt had now spread throughout my body and my chest felt
flush. I would have given most anything to play with my nipples right
then. I had to fight to stay focused and not pleasure myself, even as
James' sub taunted me for my lascivious display and obvious arousal. "Look
at her cunt leaking," she exclaimed. "What a nasty slut."

Of course that just aroused me more. Sir was laughing at me as well
commenting how easy it was to manipulate me into a compliant piece of fuck
meat. At a count of 20 strokes I began to moan before I could vocalize the
count. By 30 my whole body was quivering. By 40 I had enough and needed to
cum. As I paused and turned my face toward the camera. I'm sure I had an
expression of pure lust as I began to beg for permission to cum. I knew it
would only take a couple strokes of my clit and a pinch of a nipple to get
me off. I was confident my plea would fall on deaf ears. Perhaps Sir would
stop my paddling, but I would have bet anything he would have another
torture prepared to takes its place. Surprisingly that isn't what happened.

Well, maybe Sir had plans like that, but his sub interceded. I heard her
tell him that I'd been good and that I should be allowed to climax. As a
sub, I am sure she had been in my position before and knew exactly what I
was feeling. Although I had never met her, I felt a kindred spirit, a
sisterhood if you will, in her. I had been jealous that she was
experiencing what I could not with James' hand on her ass and no doubt his
cock in her holes. But in that moment, I only felt peace that she was
looking out for my needs. Whether it was her intercession or his plan all
along, Sir told me to sit back down in my chair, spread my legs and put my
feet on the top of my desk.

That is how I found myself spread wide, dripping and broadcasting my most
intimate needs to at least two people. James took control again giving me
his usual instructions about how to play with myself for his visual
benefit. He didn't let me come straight away, but he didn't make me wait
too long either. Mostly he wanted to be sure I felt the pain and pleasure
of sitting on a freshly and properly spanked butt. I have a padded chair,
but it still hurt. But I didn't care. Thankfully he only made me tease
myself for a couple minutes before he asked his sub for confirmation that
it was OK to let me cum. She was agreeable so he told me to rub myself
hard. I didn't need to be told that twice. I arched my back as the first
waves of climax flowed like water through my body. It didn't matter that
they were not broadcasting their own camera because my eyes were shut
tightly. As my back relaxed I thrust my hips forward pressing my needy
pussy toward the webcam.

"Oh God, I want to fuck you both," I yelled. I was lost in my fantasy world
as my climax overtook me. I thrashed about in the chair and my legs fell
off the desk. I almost slid down to the floor, but I managed to keep it
together enough to avoid than inequity. When I finally did calm down I
heard the unmistakable sounds of two people fucking.  Distorted by his
infernal box, but clear enough to know James was drilling his sub like a
stallion. Now I was starting to get jealous because she was getting what I
craved. I had to listen to them for about ten minutes. Well, I suppose I
could have ended the chat, but I really wanted to hear her get pummeled. It
also made me want to meet James as he was obviously as skilled in real life
as he was online.

He made her beg in much the same what he makes me beg for my orgasm. To my
ears she sounded a little better at it than I imagine I do. She does have
an experience advantage over me. When he did finally grant her permission
to orgasm, it was well worth the wait from my perspective. She clearly had
a major league climax. I wondered if it was just from the fucking or if he
had done other things to her as well. I could only imagine what else
happened at their house that night. But I knew every detail about what I
had done that day. It went into my journal and as I finally crawled into
bed, exhausted but satisfied, my hand went between my legs thinking about
her. Of course, if I accidently came, I would have to be paddled again. I
smiled to myself.