It was Sunday afternoon, I was waiting for word from Kennedy, her flight had been due to land a little while before. Then, she called. That was unusual, a text was more her style. "Hey, Matt." She sounded unusually cheerful; I wasn't sure if it was Kennedy or Kiki calling. "Hey." She got straight to the point, telling me, "I want to give you as many blowjobs as you want this afternoon." That was a rare treat, I might wonder what bought that on, but I wasn't going to argue.
"OK." "So I want you to be naked, on my bed, and hard when I get there, OK?" Not unusual, I had a spare key to her place, I quite often waited for her on her bed. "OK." "Unless, …" There was another part coming. "Unless what?" "Unless you want me to spank you and fuck you in the ass, before the blowjobs. In that case, you should be kneeling on the floor.
OK?" She was offering the chance for me to get tortured and humiliated. Unusually, it was my choice, I usually left that sort of decision to Kennedy. "OK." "OK. Bye." I gathered a few things together and made haste to Kennedy's apartment. It took her about half an hour to get home from the airport, so I didn't have too long. The last thing I wanted was to annoy Kennedy by not following her instructions. I got to her place, let myself in and stripped off.
Then, I lay on the bed. I was already hard, that part wasn't a problem. So now I was set. Maybe I should have wondered about what caused this unusual generosity, or maybe I just didn't want to look the gift horse in the mouth. She was sometimes nice to me, well really she was always nice to me; she did things I wanted her to do to me.
Though some of those things I didn't like admitting I wanted. The ass fucking and the spanking in particular. I hated those, but they turned me on so much, I loved them as well. And "being nice" to me may just be a way so I never know what to expect, it certainly kept me wondering. So I'm lying there, hard as per instructions, daydreaming of the blowjobs I'm going to get, I've decided blowjobs and no pain and humiliation are my choice. Then, I hear the key in the lock.
I sit bolt upright, and jump off the bed to take up a kneeling position, before I realized what happened. That wasn't my plan, but now Kennedy was walking into the room and saw me kneeling there naked. Her reaction was a bit unexpected, but Kennedy was acting a little strange overall today. She walked over to me, and hugged me, with my face in her belly, saying, "Aww, thanks, I'm so looking forward to torturing you.
I would have gone straight to the blowjobs if you'd wanted, but you've made your choice, too late now." I'd dropped myself in it, and I'm not even sure why. She hadn't said she preferred this option, she'd left it entirely to me.
If she'd said she wanted to, I'd have had difficulty refusing, but I'd be able to blame my humiliation on her. Now I had no one to blame, I as good as admitted I wanted this. That in itself was humiliating. Then, she patted me on top of the head, and said, "Stay there." She disappeared into her closet. This was usually a good thing, what emerged was usually good for me, in some way. What emerged was Kennedy in her dominatrix outfit.
Kennedy didn't go for the traditional corset and lingerie, that wasn't her at all. She would have been happy just wearing her normal clothes, that was what she was comfortable in. But, she did find a look that agreed with her, she was wearing a leather jacket, just the jacket, nothing else. It came down just to pussy level, so gave you hints of what was under it. It was unzipped so you could see her cleavage, and she had a swagger.
If you can imagine the Fonz as a mostly naked porn star, that's Kennedy. In one hand she held her totem of power, a leather horse riding whip, with a red leather tab on the end. I'd found that on Amazon under BDSM gear and gave it to Kennedy as a birthday present.
Then, I had to use several safewords to convince her I really, as in really, really I'm not kidding, hated her using it on me, and it should be a ceremonial item only. That thing stung like a motherfucker. I could just about stand being spanked by the leather paddle I'd given her, that was wide and flat, it didn't sting, but the whip was too much.
In the other hand she jauntily slung her special shoes. They were for use only in scenes indoors, and only after a ceremonial foot washing, so they were kept clean inside and out. Unlike her usual shoes, they had heels and straps.
They were gold colored, and reminded me of Roman sandals for some reason. They had a wide pleated strap which fastened over the arch, with Velcro. (Obviously, the Romans never had Velcro.) That left her toes accessible.
It looked like she was going to go through the full gamut of ritual humiliations for me. She sat down on the bed, which was behind me, then ran the whip over my butt and up between my legs. It tapped my balls lightly, I started to panic, my breathing went ragged, I'm sure my heart rate soared, and I got ready to shout the safeword. I didn't want her hitting me with that, on the balls is the worst idea possible. It was a rush and a turn on though, and my dick twitched. Then, she gave me a playful swat on the butt with the whip.
At least I hoped it was supposed to be playful, it still stung. She coughed like she was trying to get my attention, so I looked back and she was making turning motions with the whip, indicating I should turn round to face her.
I turned, so I was kneeling facing her, my hard on pointing stiffly at her. She trailed the whip along the urethra on the underside of my dick; a drop of pre-cum emerged. God she was turning me on as well as scaring me shitless.
I was in full flight or fight mode, but I didn't move. Satisfied with my reactions, she launched one last barb before ordering me to work, "I'll use that on you later." She usually didn't use it on me, I had persuaded her I really did hate it, but if she didn't occasionally I wouldn't get scared. I earned my use of a safeword when she did. You guessed it, the thought of that also turned me on. I'm a mess, aren't I. Finally the order, she waved the shoes, and asked, "Well?" That was my cue to get the ritual foot washing gear together.
I did, and I performed the ritual washing and anointing of her feet, then placed them in the shoes. She stood up, towering above me in the heels, and pointed to her feet with the whip. So I prostrated myself before her, then she lightly tapped me on the shoulder with the whip, my cue. I crawled forward and started licking and sucking on her toes. I'd been surprised by how much I liked that the first time I did it, and so it seemed was Kennedy.
It should be a really humiliating thing to do, but I got turned on by how sensual it was, not by the humiliation. All too soon, Kennedy signaled me to stop, another painful swat on the butt.
I looked up at her, she was as sexy as any Greek Goddess, and from that angle her sheer presence cowed me. She was smiling, and breathing heavily. She breathlessly commanded me, "Get things set up, and don't forget the paddle and the linear accelerator." I had to go fetch the objects of my torture and humiliation, as a prelude. For reasons which I won't go into here, the strap on dildo was now called the "linear accelerator." I'm not entirely sure that was a good choice of name as our doctoral experiments involved the use of a linear accelerator for real, you could get confused and/or turned on talking about the wrong thing if you weren't careful.
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 …