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I pulled the desk over to the breakfast bar, and retrieved the paddle and dildo and laid them on the desk. Then, I got the toybox out and laid the rest of the things she might need on the counter. I looked to her and she indicated I should take my position. That was the position we'd found most conducive to my torture, bent over the breakfast bar. She took a few Velcro cuffs and the spreader bar, and soon I was immobilized and helpless, and so fucking turned on it was unreal.
She sat on the side of the desk in front of me, and idly fondled the dildo and the paddle. Then, she sat fully on the desk facing me, her knees apart and the jacket parted so I could see everything and she inserted the dildo into her. She was already turned on; her pussy lips were pouting and wet. The dildo slipped in easily. She gave a little moan, then took it out, stood up and strapped it on. Then she stood to the side, so the dildo was pointing directly at my mouth. The heels put her at just the right height for that, and using it on my ass as well. She didn't need a command; I knew what I was supposed to do and opened my mouth. The dildo was forced in and I did my best to clean off the pussy juices. That bit's not bad, I like the pussy juice.
Satisfied with that, she squatted down, so she was face to face with me, "Remember, I'm going to blow you anyway, so you have no need to use those pesky safewords." Our deal was if she forced me to use a safeword, I got blowjobs. The thought of that was, annoyingly, enough for me to not need to use the safewords most of the time. This time I'd get it anyway, so maybe I could bear more than usual; I do want to please Kennedy.
Then she kissed me, stood up and went to my rear. Before I noticed the paddle was still on the desk, there were a couple of sharp stinging whacks on my behind. I hadn't managed to summon up the safeword before she was back at my head, saying, "Thank you. I do so enjoy that." Well, at least I'd pleased Kennedy, letting her get away with that, but I didn't want any more, so I got the safeword ready for use. Then she asked, "Please will you let me do that again, please, please. Just twice." She sounded so enthusiastic, I really didn't want to go through that again, but I wanted to please Kennedy, I couldn't assent, but I didn't say no.
She took that as permission, and stepped behind me again. I got the safeword ready, but didn't use it as two sharp whacks landed on my butt. These were even worse than the previous ones; I think she was putting all the power she could muster in them. She came back to my head, tears were welling up in my eyes, she saw that and smiled. She was breathing hard, again she said, "Thank you." And squatted down to kiss me. "Don't worry that's all for now. I'm just going to fuck you now." Being fucked was not painful, I never used my safeword because of it, it was just utterly humiliating, and such a turn on.
It’s still horrible, I want to draw a veil over the actual proceedings, but to complete my humiliation, I'll tell you about it. She walked back towards my rear, she still had the totem in her hand, I got the safeword ready, just in case she used it as a whip instead. There was a pause, she was lubing up the dildo I guess, then I felt it, cold and wet on my asshole. Then pressure, inexorable pressure, and its sliding in. I'm glad she used enough lube, or this bit can get very painful.
I'm lying over the breakfast bar, utterly helpless, Kennedy is invading my rear, my dick is twitching. I'm turned on beyond belief, but I don't want to be. Each push seems to pump up my dick some more. If I was ever in two minds about something, this was it. With each thrust, my dick got harder, and tears were shed. I was so turned on, I felt I might come from this abuse. I desperately didn't want to come, that would be the final humiliation, to get obvious sexual gratification from this.
The feelings themselves are just mildly unpleasant, everyone's felt it in some form. Kennedy is into it, I can hear her breathing. It's really ragged. Maybe she'll come from the act and spare me further humiliation. It goes on, for how long, I don't know. I'm trying not to think, not to come.
Once she was done, I was in a full flood of tears. I sometimes think she's a dacryphiliac, someone who gets turned on by tears, so I don't hold back with the crying. Another thing to feel humiliated about, crying isn't something a man should do. Even a Gen-Xer like me thinks that. She examined her handy work and seemed pleased. She was certainly turned on, which she demonstrated by lying on the desk and rubbing her pussy in my face. She was again using my face as a sex toy, rather than me doing anything active. I'm happy to help in whatever way I can. It didn't take long for Kennedy to come that way. And she relaxed back onto the desk, giving me a perfect view of her pussy.
It wasn't long before she wanted more. She again pushed her pussy in my face, I couldn't move to reach it. This time her hand only lightly rested on the back of my head as a guide, and I got to actively lick her. That I like, that I can do about forever. I doubt I could do it forever really, but I like to think so, and that's the sort of fantasy that runs around my brain as I do it. I started slow, I wanted to prolong the pleasure, for both of us, but soon enough, Kennedy got impatient. There was a sharp stinging whack on my shoulder, she still had the whip. Just as you whip a horse to extra effort, she was spurring me on. I stepped up the pace, and she started arching her back and pressing harder on the back of my head, before finally I got jammed against her pussy as she came, then she relaxed onto the desk.
There was a contented sigh, and Kennedy twisted around so we were now face to face. She was smiling, she looked happier than she had for a while, I was buoyed up by that, I'd pleased Kennedy, my life's ambition. She said simply, "Thank You." Then, she continued in a contemplative manner, "I bet you're wondering what brought all this on." While not totally unusual, she was acting in a slightly strange manner, for Kennedy that is. So I nodded, and she continued. "I'm just stressed out by my orals." She was due to do her oral defense of her thesis later in the week. I could imagine that would stress anyone, but I was sure she'd do fine; she is one of the brightest people I know. Don't forget, I work with Ph.D.s and doctoral candidates, so that's saying something. Still, the most able are always the ones who underestimate their ability.
I tried to lighten the mood. "You could practice your oral on me." It was a deliberate double entendre, it could mean either practice the oral defense, or indeed, oral sex on me. I'm sure I wouldn't mind, and that would take her mind off things. She had promised me blowjobs anyway, and I'd be quite happy if she started on them.
She cracked up laughing at that point, she was doubled up and rolling around on the desk, I was half-afraid she'd injure herself, or fall off the desk, but she did neither. She calmed down, and again took up the position face to face. She said, "Thank you, I needed that." Then, she totally surprised me by asking, "Do you want to marry me?"
To be continued …
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