Anniversary Weekend Session Part 1

This did not all fit in one blog, this is the first half:

Disclaimer: Deschut and I have been playing for a year now. Most of the things in this session are things that we have been working on for the entire time we have been playing together. This was by far the hardest session yet.

Why I am writing this:
This weekend is our one year anniversary, and this session was incredible, Deschut has never pushed me this hard, and I feel very proud of a few things in it, and that I was so able to completely obey through some really hard stuff! I wanted to commemorate it and remember it, so I am posting a report here.

Note about the webcam:
I wanted to start by saying that Deschut never actually asked me for pictures or webcam, I get a huge wave of anxiety if I feel like someone is pushy about that. I told him that in the beginning. The webcam happened at my pace, first I just offered to show him my face, then my face and boobs. Once he brought it up that he would really like to see me spank my ass, and to get over it I sent him a video message of me doing it on skype. After that, the butt spanks on webcam have been part of our play, but there was one more thing he had asked me about months ago that I had never done...

The story:
Our play usually starts with Deschut telling me what toys to pull out of the dresser by my bed, usually it is just a few things, one spanking tool, my big vibrating dildo and bullet (always), and maybe some clips sometimes. Sometimes the butt plug, but I already wore that for about 5 hours today.

Every day it starts with him asking me, "Can I torture you?" and me getting a huge smile on my face and saying, "Yes! I really want that!"

But today, when Deschut told me to get the following list: nipple clamps, dildo, bullet, bathbrush, hairbrush, cane, clothespins, and the dishbrush, I knew it was going to be rough.
First, as I always do, I asked him if we could please do something instead of the nipple clamps.

Some time ago I had them on, and accidentally kneeled on the chain and kind of sat up. The nipple clamps are already right at the edge of my pain tolerance, and the extra pull really sent it over the edge. The really horrible part was when he asked me to take them off, and I knew that taking them off was going to hurt even worse. I couldn’t very well leave them on, but I felt like I couldn’t take them off either, and it filled me with panic, because I felt so trapped. He has been awesome about them since then, but I always get so scared now just thinking about putting them on!

He told me that I would get the nipple clamps (with a winky face, damn that winky face!) I showed him each toy from the list on the cam, one by one, and he told me to get the nipple clamps on first. The fear always makes me hesitate, and look over at the screen to see if he has changed his mind a few times. But he didn’t (he never does) and I got them on. The searing pain was immediate, and it took me a little while to catch my breath. I turned on my side to show him, and could see in the cam the red spreading from my nipples out to my breasts around the areola.

Next he asked me to get on my knees and bounce up and down on the dildo until I had 2 edges. This was a huge deal because of 2 things:

1. Moving around like that with the nipple clamps hurts.
2. I have never bounced on my knees on the webcam for him. Sometime, a very very long time ago, he asked if I would sometime and I told him I probably would, but to be honest, the very thought has always terrified me!

So, I asked him if I had to show him on cam, and he said no. But as I moved down to the floor, I brought the laptop with me anyway. It was awkward to bring the dildo and laptop with me, because I hold up the chain from the nipple clamps with my hand (to support the weight of it, and make sure it doesn't catch on anything), so I only had one hand! I did get down on the floor, and without even thinking pointed the cam at myself. I didn’t look at it long enough to see how I looked, only to make sure I was in the frame. I turned the dildo on high, slid it in, rested it on the bottoms of my feet, and started bouncing up and down. I felt so embarrassed knowing he could see me, but not terrified, in fact, just embarrassed enough to make me more aroused. I reached the first edge, and pulled the dildo out quickly, because I was really about to cum. As soon as I had calmed down a little bit I slid it back in, and started bouncing again, and came to an edge so fast. I think both edges took less than a minute, and I quickly stood up and moved the cam back again.

All of the moving around had left my nipples very very sore, but I was still doing okay with everything at this point. Then he told me to get the hairbrush and spank my clit 50 times. My pussy was so wet at this point that it wasn’t only the deep pain of spanking my clit, but also the slapping feeling against my tender wet inner labia. It was really really painful. I think I only took a few really short breaks though during the 50 spanks.

After I was done with the spanks, he told me to get the nipple clamps off. Once again, I hesitated, because I know that taking them off is the worst part. And it definitely was, but I did it! Then he told me to insert the dish brush in my pussy, which I have gotten better at over the past several months. It still hurts like something fierce though, once it is in. The inside of my pussy was already sore, from a task earlier in the day (I wore my big dildo inserted for like an hour and a half while I cleaned, which was a lot for the size of it), and it was so tender and painful to get it in.

Then he told me to get on my hands and knees and spank my ass for him: 50 with the bathbrush (evil) and 50 with the cane (eviler). Moving with the kitchen brush sticking out of my pussy is so awkward and difficult, and every time it touches something it pushes against the inside of my pussy and gives me a shock of pain. But I made it up, grabbed the bathbrush and did the first 50 on my right cheek. I could see a bright red circle appearing, and my breath started to get heavier and faster from the pain. Then I did the left cheek and did the same. I could see the kitchen brush awkwardly sticking out of my pussy in the cam, and it felt so humiliating, but I made sure he could see it too while I did the spanks. When I did the first whack with the cane on my right cheek, I was shocked at how much it hurt, the cane on top of my tender spot from the bathbrush was intense! I finished the 50 with the cane, with a few breaks for breathing, after I finished each cheek I laid with my ass toward the cam and my face buried in the bed, just catching my breath and my courage to continue.

The next order was to edge twice with the kitchen brush. I have done this a few times before, it really hurts quite a lot! But lucky for me, I was incredibly wet and horny, so the edges didn’t take long, and moving the brush in and out didn’t hurt as bad as it could have. The only time it hurt a lot was right at the edge, when my pussy clamped down on it in anticipation of an orgasm. The second edge almost went over into a ruined orgasm, but with a feat of will I stopped the orgasm from coming without removing the brush. After that was over he said I could take the brush out (ouch ouch ouch).

Then he told me to get 3 clothespegs on each side of my pussy, and one on my clit. I got the three on the sides of my pussy (ouch!) and told him I really didn’t want to put one on my clit. Pain-wise this is as close to the nipple clamps as I get at this point. He told me “You’ll do it. For me.” And he was right, I knew I would do anything for him, so I did it. I yelped out loud in pain when I finally got the guts up to let go of the pin. It took a few minutes with my eyes closed and breathing to get myself together enough to look for the next order from him, which was to spank my boobs with the bathbrush 50 times each side. After each was done, I turned my body to show him full-on, the bright red circles on my boobs, while I laid there keeping my legs spread to avoid touching any of the pegs. During these 50 is when I finally got a pain high (it takes longer and longer to hit me all the time!) Then he asked for 5 on each nipple. I laid there with the bath brush gently on my nipple for what felt like eternity before finally taking the first swing. My nipples were already so tender from the clamps, that first swing really made me catch my breath. Somewhere on the second nipple I lost my count after 3 spanks. Yes, I was in so much pain and so subby that I lost count counting to FIVE. I asked Deschut to tell me how many I had done!

Too long for one blog post, continued in #2...