Miss H and I frequently engage in anal play, both giving and recieving, in many forms, tongues, fingers, toys, and cock (although that's rare now with me being locked up). I've written in the past about how since we've really started engaging in chastity and tease & denial, I've been able to orgasm from anal stimulation alone. It's not nearly as powerful as by penile stimulation, but I do ejaculate and have a sort of "mini orgasm" in the process. It doesn't happen every time but it's been happening more often recently, I'd say probably four of the last five times Miss H has used the strap-on on me. When I sit on top of her and arch my back in a certain way I can usually cum every time. It's not something I've been actively striving to achieve, more of a pleasent surprise when it does happen.
Last night I was in my usual hyper sexed up state of mind. Dressed, horny, and attached to Miss H's hip like a conjoined twin. She had been hinting all day about fucking my ass with our big, 9" black dildo, and I was anxious to feel its huge girth and length spread me open. When the time mercifully came to be fucked she first ordered me to put my CB-6000 back on, which I had mixed feelings about. On the one hand the idea of being locked up and only able to receive pleasure by having my little ass fucked was a huge turn on, but at the same time I knew I would miss the feel of Miss H's hand as she stroked me. There wasn't much I could do either way so I quickly went out to retrieve it and put it on.
When I came back I was surprised to see Miss H just standing there without the strap-on harness on. I had been expecting to see her with a large rubber cock sticking out from her but instead I was met with a half smile and a hand pointing to the dildo on the night stand. "If you want to cum tonight, the only way that's going to happen is with you fucking your ass with that", she said. Not wanting to upset her I moved over to the bed, took a condom from the nightstand and rolled it down the length of that veiny cock. To get an idea of just how big the dildo is, here's a picture of it next to a medium sized butt plug for comparison.
Once I had finished lubing up both myself and the dildo I laid down on my back, spread my legs and placed the giant mushroom head of the fat cock against my hole. Slowly I worked it in, breathing slowly and steadily as I pushed inch after inch of it inside me. When I felt the rubbery balls against my ass I knew my ass was now totally full of dick. Miss H moved over and gently grabbed my ankles, pulling them up in the air and further apart so she could get a birds eye view of the show I was putting on in front of her. "That's it sissy, fuck your little pussy. Bet you wish it was the real thing, huh?", she said with a laugh. I was barely able to get out a meek "Yes, Mistress", as I furiously fucked myself, pulling the dildo out before slamming it back in again as fast as I possibly could.
It didn't take long before I could feel the familiar tingle near the base of my penis, the feeling I get when I'm going to cum from Miss H's strap-on fucking. I thought I was going to cum so I tried going even faster which only intensified the feelings. I was right there but never quite got over the edge to cumming. I stopped for a second to catch my breath and give my hand a break before picking up again. Once more it wasn't long before I thought I was going to cum again. I was so close and was sure this time I would cum only to be right at the tipping point but never able to go past. I was starting to get frustrated, yes it felt really good, but a milking would feel even better and I was so tantalizingly close to having one yet it just wasn't happening. If a ten was cumming, I was at a 9.99 and it was driving me crazy.
Miss H must have noticed how sexually frustrated and desperate I was because she took pity on me by unlocking my cage and softly stroking me as I continued to pound myself with that big cock. I don't think it took more then a few strokes of her hand before I obediently told her I was about to cum. She instantly pulled her hand off and I was treated to a miserably inadequate ruined orgasm. No real pleasure and just a stomach full of cum that just seemed to fall out of me. I was grateful for the ruined orgasm but really wanted to cum with just the dildo. I wanted to feel the buildup and release due to that cock in my ass, and that wasn't happening. To be so close and not being able to finish was just maddening and ended up leaving me hornier then I had been before.
Maybe I couldn't cum because I didn't have the right angle, or because I was for some weird reason self conscious in front of Miss H. Maybe I was just putting to much pressure on myself to cum instead of just sitting back and enjoying the experience. All those reasons that women deal with all the time. Maybe if I just relaxed more, maybe this or maybe that. Maybe.
In the past, Miss H has made me do things in order to gain a perspective what real females go through on a daily basis, wearing a tampon to get a glimpse of what having a period is like, worrying that I was to fat because a dress was to tight, etc but this experience with not being able to orgasm was a real eye opener. The frustration so many women go through, the feelings of "what's wrong with me", the inability to enjoy sex as much as they could, are taken for granted by a lot of people. It's a lesson I'll definitely keep in mind for the future, for as much as I love to cum, I love to make Miss H happy just as much or more.