I met Giant again, yesterday, and for the first time I spent the night. I had a lot of ideas for things I wanted to try out (like verbal humiliation and "impossible" tasks), but didn't get to do them all. Not a bad thing, this just means I've got more in store for him at some later date. The only really, really new thing we tried was cock bondage. But we didn't do it much. I'm going to do more of that at some later date, maybe combined with some light CBT.
I wanted to put my mark on him, so I made a bite mark on his chest. I also made long, red scratches on his arms and rope marks on his back and across his shoulders. I tried marking his ass, by spanking him, but only managed to make some very faint bruises. Guess I'll have to try harder next time...
He used a safe word for the first time, adorably saying "orange" in stead of "yellow"/"pink", because he was flustered and didn't remember. (Still, I got the meaning behind the word!) I'm glad he did. I need to train him to use the safe words more confidently, and not feel bad about it.
After spanking him really hard, and him using the safe word, I was nice to him for a while. I gave him compliments, stroked his hair, told him I was proud of him, and that I thought he was sexy. I'm not sure if it was the spanking or just being comforted and held (probably a mix of the two), but he broke down and started to cry. He's cried in front of me before, but that's just been a tear or two. This was proper crying. I think it helped him get rid of other negative emotions as well, unrelated to the two of us. Afterwards, he was spent. Empty. Tired. But he felt good. As if the weight on his shoulder had been lightened.
After a break and some more food, we continued. It was time to fuck his ass again. I fingered him first, to make him open up to me. He's getting really good at relaxing and enjoying himself. Then I fucked him face-to-face, with his legs on my shoulders. It worked fairly well, but is tiring for the both of us. We switched so I was on my back and he was straddling me. While I've fucked him before, we haven't made that position work before.
He worked his way onto the strap-on dildo and rode it like a cowboy. Like a girl would do, when she's riding someone's real cock. I was stroking his dick, he had control over the depth and angle of the penetration, and soon climaxed from it.
I just lay on my back, watching him pleasure himself. His eyes half closed, his head arched back, a mad grin on his face. That was sooo sexy! I totally get why guys enjoy it when a woman rides them!
That was last night. This morning, I fucked his ass again. But this time I only used my fingers. He ALMOST managed four fingers, but was a bit too sore. Two fingers arching and pressing on his prostate, while I was stroking his dick, soon made him come again. I also masturbated this morning, which was nice.
We cuddled and played and fondled each other both in his bedroom, and later (once his house mate had left) in the kitchen and on the couch in the living room. Just as we were headed out the door, fully dressed and in the hallway, I also sucked his dick a bit. I love sucking dick.
Then we left. I hope he's still trembling, remembering what I've done to him.