Let's Play Doctor

After my exam, I was thoroughly excited and completely unsatisfied. I knew Jeffrey was aroused as well, but true to his character, he wanted to go down his little checklist.

Next item was spanking. I'd been swatted during sex, I'd been pulled over someone's knee for a few hard hits until I managed to get away. But I had never just presented myself to be beaten. It was my stipulation that since this was the first meeting, there would be no restraint. I needed to know that if I had to get away, I could. I was apprehensive and slightly afraid. I didn't know how much this was going to hurt and I didn't know if I would be able to take it.

I had my clothes back on, as I'd previously been instructed to dress. I was now ordered to strip. There was no eroticism, no sensuality, just his cold eyes watching me. His tone of voice could have belonged to a prison guard, instructing an inmate to strip. He led me to an easy chair in the living room. I mounted it backwards, knees on the cushion, hands on the back of the chair. I pushed my ass out and assumed my position.

He hit me once with his hand. It was not hard, but it did sting. And again, an again. His blows were soft, but not gentle. He was considerate enough to spread then out so as to not damage or area too much. The hits were getting harder, I was starting to cry out with each one. I could tell this excited him as the blows became less methodical. They started raining down. The slap of his hand on my tender skin was growing louder and louder along with my screams. I was squirming, but holding my position. I closed my eyes and brought myself to a kind of tranquil state, where pain didn't exist. I'm honestly not sure how long the spanking lasted. I know by the time he ordered me to stand up, my ass was red and hot.

Jeffrey is many things, but merciful is not one of them. He had a stool set up. It was the kind with a round seat and four legs. He had me bend all the way over it so that my hands were grasping the front legs and my feet were at the back. I was spread just wide enough to expose my tender pussy. He made note of this and immediately began to target it with a riding crop. Now I can take a crop pretty well, it lacks the heavy impact of a hand or a paddle. But in the hands of someone who knows how to use it, it is pure agony on tender skin.

My ass was red and raw from the precious spanking. The sting of the crop was far worse than something heavier would have been. Jeffrey systematically chose the most sensitive spots and targeted them. The curve of my ass, the insides of my thighs, my asshole and my cunt were all favored targets. I lost any sense of modesty and began screaming, begging him to stop, squirming, but all the while, holding my position. He reached into the bag of toys I'd brought and selected my medium-sized glass plug. He put just enough lube on it and shoved it in my tight ass. This was enough to make me scream bloody murder in its own right. He asked me if it hurt and I said yes. He then told me he'd give me something to take my mind off the pain.

He grabbed a leather paddle and proceeded to hit me as hard as he could. I could feel tears running down my face as the blows came harder and harder. There was no rest. He would hit one place over and over until I squirmed out of the way. Then I would be punished even more. He pushed my legs further apart and started bringing the paddle up between my legs. At some point during my agony, he put his hand on my back to hold me down.

Finally after an eternity, he stopped the hail of blows, but he wasn't done hurting me. He started twisting the plug around in my ass. It's not a big plug, but the shape and rigidity of it makes it a bit unforgiving. He pulled it out quickly and forcefully evoking another scream from me. Then he put it back in. In and out over and over, he fucked my ass with this small glass demon. I could tell I was close to cumming and I asked his permission to finish. It was denied and I was then instructed to hold my ass open. He then grabbed the crop and swatted my open, sensitive hole until I begged for mercy. He then told me I would have my reward.

Fearfully, I stayed there, uncomfortably bent and completely exposed. He pushed the plug back in. I was quivering as I waited for more blows, or some new pain that he hasn't contrived yet. I closed my eyes, ready to take what he was going to dish out. Instead of impact, I soon heard the familiar buzzing of my wand. My legs widened greedily as he brought it close. Now a wand can definitely be used as an instrument of torment, but my anatomy allows very little direct contact to my clit, so it's always quite wonderful for me. He held the wand close to me and told me that if I wanted to cum, I was going to have to work for it. He spanked me a couple of times to encouragement. I started shamelessly grinding on that wand. He just held it, making me work for my own pleasure. But I needed it so badly that I didn't even care how humiliating this really was. It took me all of two minutes to cum harder than I'd previously thought possible. Throughout the spanking and anal violation, my pussy had remained wetter than any sane woman's should have been. After my release, I collapsed. I just sat there, probably a little bit in shock.

After that we took a little break, we walked outside naked, went down to the river, sat and chatted. I remember the chairs we sat on were metal with a diamond pattern that pressed into my skin. It was gorgeous outside and the sun felt amazing on my naked skin. After a bit we made our way back inside and he led me to the bedroom.

I got up on his bed on hands and knees and presented my holes for his use. He was instantly hard, he'd been waiting for his release all day. But unfortunately for him, a couple of minutes after he slid it an started thrusting, he lost his erection. After 10 minutes of trying to revive it, which consisted of me gagging a significant amount, he gave up and pushed me face down on the bed. He went and got the wand and positioned it between my legs. I suppose his rationale was that if I was receiving some pleasure, I'd be able to take more pain.

I started moaning as the wand went on, but I was unprepared for what came next. I didn't know what he hit me with when I screamed. I turned around to see a fairly narrow, fiberglass rod. It was similar to a cane and had the same effect. A caning is so much different from a spanking. A hit with enough force will break the skin. He wasn't hitting me that hard, but it was enough to leave my ass striped black and blue on top of the red. The intensity of the blows fed me and I came several times. Right before each one, I'd beg him to hit me harder. This was more intense but more relaxed. Sometimes I'd ask for a break and it was granted. About what was probably only about 15 minutes, I said I couldn't take anymore so we stopped.

The rest of the day was idle. He made me a sandwich while I dressed for work. I knew work was going to be hell. My ass was already bruising. He had taken at least 50 pictures throughout the afternoon. But the untimely death it an iPhone has rendered those unrecoverable so I guess I'll just need a repeat performance to acquire some more.