Friday night brought a very unexpected orgasm for me… especially as it had been less than two weeks since my last one – I can’t even remember the last time I had two full orgasms in less than a fortnight. And it was all the more unexpected because I don’t think Mistress had planned it at all. I say this because she edged me once and then after letting me cool down she started teasing my cock again and eventually edged me a second time, leaving me rock hard and aching for more.

I was surprised when she grabbed my cock for a third time and even more surprised when she subtly indicated that she wanted me inside her. I moved between her legs and pressed the tip of my cock against her pussy, something which is so rare these days I always feel rather ‘amateur’ at it. Unfortunately since Mistress had a small operation she seems to find penetrative sex quite uncomfortable. I thought it was just when she was on top, but now it seems like it’s when she’s lying down as well.. and as soon as I entered her it was clear it was hurting her.

Obviously I don’t want to see her in pain, so my instant reaction is to pull back and as you might expect it has a somewhat detrimental effect on my cock as well. But Mistress wasn’t giving up and she grabbed my cock to try and keep me hard and we eventually tried again. Having already been edged twice and finally feeling Mistress’s gorgeous pussy wrapped around my cock it was very quickly that I felt the third edge coming down the track.

I warned Mistress that I was getting close again and she told me to ‘Fuck me and cum….’, so that’s exactly what I did, though it felt like I was only about half way in. It felt wonderful to cum inside her pussy of course, but I hate thinking that it’s hurting her so it was difficult to enjoy it completely.

When I finished cumming I moved down between her legs and started to lick her pussy, it tasted gorgeous but there was no sign of my cum so Mistress had me lay down and she sat on my face. I could taste it a little more but there wasn’t the torrent I was expecting, maybe I was deeper inside than I thought? 

While it’s unfortunate that Mistress finds it painful to have ‘spur of the moment’ penetrative sex (I wonder if it might be easier once she has had her dildo inside her and cum on my tongue?) and I know it bothers her that she feels bad for me about it, personally speaking I’ve honestly never felt like I am missing out. Mistress’s mouth feels just as good to me (if not better) and the kissing and edging she gave me before this was absolutely amazing. I love kissing her so much and maybe one day she will let me cum in her mouth again….and then kiss me. :)

This was my sixth orgasm since our tenth chastity year began on April the 1st, which is as many as I had all last year! By contrast, last year I had eleven ruins and this year so far it’s been just one. Perhaps I am looking at a long period of ruins over the next six months to compensate?

Another Full Orgasm!

The Ultimate Male Chastity Key Holding Experience