For as long as I can remember I have been printing this list out for my Mistress to fill in before each of our Femdom sessions. I'm not sure if she's ever ticked the 'Surprise Me' box before, I think she maybe has but it was an awfully long time ago. So I was pretty surprised to see this this morning...
I guess because this box never really gets ticked I've never really thought about what I would do if it did, and I didn't have an awful lot of time to think about it. I guess there's a number of more adventurous things I could have done, but what I elected to do in the end was wear the Oxballs Cock Sling and insert our older (4 ball style) glass butt plug. The thinking being that I was hopeful that Mistress would take the hint and use her strap-on on me, like I've been hoping for for ages!
When Mistress came into the room she noticed that I had the Oxballs on and said 'So you chose the Oxballs to surprise me then...'. I said 'yes' but didn't give away that that wasn't the only surprise. She found out shortly afterwards when she had me bend over on all fours on the floor and saw the glass ring sticking out of my ass, and was seemingly very surprised indeed!
Actually I did have another idea, ages ago I bought this ball stretcher thing, which is just like an inch wide strip of leather with press-studs to join it together. But I can't get the damn thing on, my balls are just too damn tight!
Anyway, Mistress gave me a short and mild whipping, not really punishment, just a little reminder, before having me worship her feet while she played with her glass dildo. I had to push the butt plug back in a few times as it started to slip out, but it wasn't too bad because I didn't go overboard with the lube.
When she was satisfied with my foot worship, Mistress tied me down on the bed, blindfolded me and started stroking my cock, once I was nice and hard she straddled my face and my cock a few times before teasing me with her ass. All the time she left the butt plug in and sometimes she grabbed it and played with it while she was stroking my cock. As the session progressed she abused my cock more and more, using a hairbrush and the cock-whip and stroking it hard and fast even though it was held tight in the Oxballs (no lube either!).
Eventually she clipped pegs on my nipples and left me alone for a short while, and when she came back she took the blindfold off, straddled my face and pushed her 'cock' into my mouth. She looked so hot in those awesome RodeoH strap-on pants, they were such a good buy, I just wish we used them more often.
Mistress removed my butt plug, untied me and told me take off the Cocksling (which was starting to sting a little by now) and then told me to turn over and get up on my hands and knees. Then she positioned herself on the bed behind me. I felt her spray a good quantity of lube on my asshole and felt her feed the head of her strap-on into me. I pushed back, eager to feel it inside me at last. As I did so Mistress reached down and grabbed my cock and stroked me as she fucked me. It was so fucking hot and it felt absolutely amazing. I think if anyone wanted to try anal sex for the first time I would really recommend using a butt plug for half an hour or so beforehand, it made such a difference. I have never enjoyed it as much, or been so comfortable being fucked before...and the stroking just topped it off perfectly. It was awesome! I would have loved to have cum like that, I really would, but sadly after a few minutes Mistress pulled out. Afterwards she said to me that she felt like she could have continued for a lot longer (whereas in the past it's often been hard for me to take, even though I've wanted to do it) and I really wished it had gone on much longer, but still. Hopefully Mistress will fuck my ass again soon!
After that Mistress had me lick her to orgasm, which was unusually quick and quite intense. She tasted so good, and it had been six long days since I'd been able to enjoy her with my tongue. Afterwards she had me lick all her juices off her skin and the sheet before tying me to the bed again and stroking my cock hard and fast again. She allowed me to tongue her ass a couple of times (very briefly) and then knelt beside me, giving me a good view of her pussy and ass. She kept looking back at me, smiling as she pumped my cock. I kinda thought she was going to ruin me, but when I told her I was close she told me she was going to allow me to cum.
It hit really hard, and each spurt had me bouncing on the bed. Not only that but each time Mistress stroked me it felt so intense I was bucking so hard... and I could feel my cum spraying everywhere and landing on different parts of my skin. When I stopped cumming Mistress gathered what cum she could find and fed it to me from her fingers. Finally she lowered her dripping wet pussy onto my face one last time, she tasted incredible!
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