My Day Of Anal Play

I had to drive the child to the bus stop in the morning, so I wasn't expecting what happened when I returned. It was still a little dark outside, the sun had not yet risen over the treetops. I found the back door, the one I normally used and had gone out of that morning, to be locked. Since I don't carry a key, I only hoped the front door was unlocked.

As I walked around the house I wondered how the door had gotten locked since I didn't think Mistress was up yet. But as I reached the front door, I realized I was wrong. Mistress stood at the door peering out the window. She smiled at me and said, “If you want in, you will have to strip naked.” That was, needless to say, a shock. I looked around to see if anyone might be watching. Seeing no one, and realizing the sun was getting higher, I quickly stripped completely, and asked her to open the door. Mistress just smiled back at me through the window and said, “Now make yourself hard.”

I don't know about the rest of you, but I get embarrassed when Mistress tells me to masturbate. I don't like doing that in front of anyone, even her. But as I seemed to have no choice, and I didn't want to spend any more time on the porch than necessary, I began playing with “Charlie” (the name I've given to my cock). Because of the situation, it didn't take me long to get Charlie erect. Mistress opened the door and let me enter.

Once inside, Mistress ordered me to stand behind one of the comfy chairs in the living room. Then she pulled a blindfold over my eyes. All was dark. She bound my ankles to the feet of the chair. Then she bound my wrists and fastened the ropes to the front feet of the chair, bending me at the waist. I felt pretty much stretched to the limit with my ass exposed to her every whim. I felt very vulnerable!

Mistress stood between my legs with her body pressed against me exposed bottom. She ran her fingernails up and down along my back for a few seconds. Then she pulled up a kitchen chair and sat down, her bag of toys beside her. She ran her fingernails up and down my inner thighs and across my buttocks. Chills ran up and down my entire body. I felt exposed, open to her every whim. I wondered what would happen next. Charlie, and my balls, were hanging between my legs on her side of the couch. That made me nervous.

Mistress tied a string around the end of my cock, just behind the head. I later learned that she had a small medicine cup suspended just below my cock. I could only guess what it was for. Then I felt her applying lubrication to my anus and the surrounding area. Then her finger pushed it's way into my ass and swirled around for a moment. Next came an icy-cold, glass dildo. She had frozen it just to add to my discomfort. It worked!

Mistress worked the ribbed dildo in and out of my ass for several minutes while fondling my cock and balls with her other hand. Mind you, during all of this, Mistress was telling me about all the things she “could” do to me while I was in this position. That not only made me more nervous, but it added to my humiliation at the same time.

After a few minutes of this, Mistress removed the dildo and replaced it with a cold, glass butt-plug. It was a bit larger than the dildo and filled me a bit more. It wasn't totally uncomfortable, but it was obviously bit bigger. For the next few minutes, Mistress ran her fingernails from my knees to my crotch repeatedly, teasing my balls at the end of each trip.

Next, Mistress began teasing my cock. She ran her fingers from the base of my cock, down and off the end. She only went in this one direction. She did it so very lightly. It was driving me crazy! There was not enough pressure (or stimulation) to allow me to reach orgasm, but made me want it more and more with every stroke. Before long, I found myself begging her to make me cum. But she only laughed and teased me with her words as well as with her fingers.

I could feel my pre-cum working it's way down the length of my cock. I instinctively knew it was dripping into the medicine cup Mistress had suspended below it. I assumed there must be quite a bit by that time. But I will never really know.

After what seemed like an eternity, Mistress stopped stroking my cock and informed me that she was now going to milk me. Then she, rather abruptly, plucked the butt-plug from my ass. It took me by surprise, but didn't really hurt. Then it was quickly replaced by a gloved finger. I could feel her massaging my prostate. I knew it wouldn't take her long to produce exactly what she wanted. I could feel that her finger was in the exact right place. And I was right. In a matter of minutes I felt the flow of semen pushing through my cock and dripping from it's end into the waiting cup.

But that was not the end. Oh no. Mistress allowed me to rest for a few minutes as she explained that she was going milk every single drop of cum from my balls before she would quit. She re-inserted her finger and milked another fairly good amount of cum from my balls. She repeated the process several times until she could get no more. I was exhausted. But I knew my torment was not over.

Once Mistress was sure she had drained the last few drops of cum from my balls, she removed the cup and the string that held it in place. She told me that she was saving that for later. I didn't know what she meant, but I had a pretty good idea. I'm also pretty sure you know as well. Mistress replaced the previous glass butt-plug into my ass. It was not as cold this time, thank heavens. But it was still cold enough to get my attention.

Mistress took the time to attach a small rope, with some kind of weight attached, to my balls. It was uncomfortable, but not overwhelming. I could hear her doing something behind me, but I couldn't tell exactly what it was. Then I felt her favorite strap-on pressing into my ass and I knew what she was doing.

At first, Mistress pushed the dildo slowly into my rear. Once it was all the way in, she began to push it it in and out in a slow, rhythmic pace. She was stretching my anus to it limits, or so I thought. Let's just say it felt like it. Her pace began to pick up. Before long, she was fucking my ass rather firmly and fast. It was all I could do to keep from crying out. But I managed to take all she could dish out. When she thought I had had enough, she pulled the strap-on dildo out of me and re-inserted the glass plug.

Finally, Mistress released the rope that held the weights which dangled from my balls. Even though it had not been painful, it was a relief to be rid of them. I could feel her fingers lightly fondling my balls and cock again. Her voice was reassuring, but her words were humiliating. She talked about the many things she could make me do, as her slave, that involved many other people. I won't go into details about those fantasies, just imagine your most exciting, yet humiliating, fantasies and that will do it.

After about another 15-20 minutes of teasing my cock, she released me. The first thing she did was make me drink the cup of cum she had collected during my ordeal. By that time I was exhausted and she allowed me to take a nap. It was almost noon and all this started a little after 7:am. All I can say is, I have a truly wonderful Mistress. I suspected that I would soon be returning the favor... Giving her all the orgasms she can handle.

nemo