Allyson's On-Line Dates

Brandon rummaged in the drawer again and produced two lengths of soft cotton rope, each about four feet long. They were the ones Kev and Kendra had salvaged from my beach bondage session with Nick at the resort, and they had willed them to me since I didn't already have any rope in my collection. Brandon pointed to the bed and I laid on it face down. "Wrists to ankles," he ordered gruffly. Certainly no Charles-style tentativeness here. I wasn't entirely sure I liked his way of ordering me around, but it did add to my feeling of submissiveness, which brought a further tingle to my waiting pussy. I reached down and grabbed an ankle in each hand, shoving my ass in the air and my face into the bed as I doubled over.

Brandon expertly wrapped each wrist-ankle pair with turn after turn of rope, moving along with each turn so that the rope never crossed over itself. He checked each turn for tightness, getting each inescapably snug without cutting off circulation. I don't usually care for rope bondage -- that's one reason that I didn't originally have any in my collection. I've been tied up tightly enough to really hurt after a while. But Brandon's boasts about his expertise with rope bondage seemed to be well founded. The wraps of rope fit as comfortably as the leather cuffs I usually use. My position wasn't much different from the one the spreader bar had forced me into, but the novelty of being so securely attached to nothing but myself was thrilling in an odd sort of way, and my pussy began to juice more and more as Brandon finished his wrap and tied off. I wrestled experimentally with the bonds and I could barely move an inch.

There were two more pieces of rope in the drawer. Brandon wrapped the other two just below my elbows and knees, securely welding my forearms to my calves. I hadn't been able to move much before, but now I really couldn't do anything beyond wiggling my ass in the air. My total helplessness was intoxicating, and my pussy was really starting to cream.

He took the largest plug from the dresser. I didn't have to ask him to lube it -- he coated it thoroughly and put a dollop on my asshole, and pushed in the plug. His technique with the plug should have warned me that all was not quite as it seemed. He didn't exactly jam it in, but he wasn't delicate either. He pushed it firmly and steadily until everything was inside but the flange. Since he hadn't slowly stretched me out, it hurt quite a lot when it went past the widest part, but it stopped hurting when it came to the snapback and my sphincter closed on it, sealing it in. I savoured the familiar stretchy, filled-up feeling, and my pussy tingled with satisfaction. The first stages of an orgasm began to creep up from it.

He went to the dresser and came back with one of the more effective pain devices I kept there. I had two paddles, one of them fairly large and leather-covered and one a narrow rectangle made of plain wood. That was the more painful one because its narrower shape concentrated the impact, and it had no cushioning. Of course he picked that one.

My body jerked as he brought it down smartly on my ass with a resounding "smack." It was hard, but well within my pain tolerance. I left out an involuntary yelp. The pussy tingle that had started with the butt plug intensified as the pain ramped up the complex of sensations.

He kept at it, spacing out the strikes by about four or five seconds. He moved around my body, laying smacks on my back, the outsides of my legs, and the insides of my thighs, an especially sensitive area. I was happy to note that he avoided the area of my kidneys, a well-known no-go area for impact play. I could feel my arousal ramping up with the pain as he reddened my skin. It was terribly erotic, but I was beginning to wish he'd add something a little more directly sexual to the impact play.

Since I was face down, he had no access to my tits, but I've sure he would have whacked them a few good ones if he could have. He even laid one right on the protruding bit of the butt plug, driving it abruptly further into me for a second before the flange stopped it. That produced a starburst of pain in my asshole.

Was it my imagination, or was he getting harder? Maybe my skin was getting sore, or my nervous system was getting over-driven, or something. But then I decided that he really was getting harder. I looked over my shoulder and could see that instead of little swats from the wrist, he was pulling his arm all the way back and really doing a power-stroke. My little yelps were starting to turn into real shrieks of pain. Finally he turned the paddle sideways so it would go between my legs and hit my pussy where it showed between my ass cheeks. The narrow edge of the paddle concentrated the impact on my most sensitive spot, and it hurt like absolute bloody hell. I screamed.

"Yellow! Yellow! For fuck's sake, back off. That's way too hard."

"That's enough backtalk, cunt. You agreed to be my sub and I'll do it any way I want."

"You fucking son of a b -- MMMPPHHH!" When I opened my mouth to protest, I suddenly felt the ball of the stuffer gag being shoved into it. He cinched the strap behind my head and the mouth cover settled in place to block any sound that made it around the ball. He cinched the strap unnecessarily hard, making the edges of the cover bite into my skin. I was totally pissed with him, since we had agreed to no gags until we got to know each other better and I could trust him not to overstep any boundaries. Now I just had to take whatever he dished out, which wasn't the deal. I tried to protest through the gag, but all he said was, "Sorry, cunt. I can't understand you."

I tried to control my outrage at his attitude and to relax and enjoy what he was doing to me, since I couldn't very well do much else. To my relief, he did back off some, continuing to hit me harder than I would have liked but not excruciatingly hard. He didn't repeat his side-paddle-on-pussy stunt, at least. I had to admit that the increased feeling of helplessness and restraint added by the gag, and by my knowledge that I couldn't resist anything he wanted to do, was driving my arousal higher and higher. As each smack jerked me forward in the ropes, I got closer and closer to what felt like it was going to be a really big orgasm.

He went on a while longer, then decided to change it up. I could feel his fingers gripping the end of the plug in my ass, and I prepared myself for anything. He didn't just yank it out, as I'd feared, but he didn't exactly ease it gently out either. It came out the way it had gone in, with a slow, steady pull that caused another burst of pain as the widest part forced itself past my sphincter. I yelped ineffectually behind the gag.

The way I was tied up with my face in the sheets, I couldn't see much of what he was doing behind me, so I just had to wait to see what he would do next. I felt a dollop of cold lube hit my asscrack -- a good sign, I thought. Then I felt something hard being pressed firmly against my asshole. It didn't feel like anything I recognized from my toy drawer -- not a butt plug, and not a vibrator. I don't have a butt dildo, though my vibrator has gone up my ass more than once. Whatever it was felt really big as it forced my sphincter open. Then I got it. He was ass-fucking me with the handle of the paddle.

That paddle has a really fat cylindrical handle to give the user a good grip. The end is rounded, thank God, but it doesn't have a smooth taper as you'd expect from anything designed to go up an anal canal, and it's somewhat bigger than the average butt dildo as well. I tried not to tense in apprehension of what something that size and shape would feel like forced up my ass. Fortunately, my ass is pretty used to being stretched out by big toys and big cocks, and he used a little more patience than he had with the butt plug. He spent quite a lot of time getting it in, inch by painful inch, until I could feel the flat of the paddle stop it as it connected with my taint. Then he started fucking me with it, sliding it slowly part way out and then all the way in again.

Once it was all the way in, it really didn't hurt all that much, and the feeling of being slow-fucked by such a weird object was sending new waves of pleasure through my body. My orgasm had been gathering in waves, rising as Brandon did something to me that my body could transmute from pain into pleasure, and then falling as he did something that made me angry or afraid. I could feel the current assfuck ramping me up again, and I began gasping rhythmically in time with his thrusts. I was getting desperate to cum and find some release from the swirling blur of sensations that were going through me, but I can't usually finish without something being done to my clit. I was dying to get a couple of fingers on it and bring myself off, but of course there was no hope of that. And with my mouth stuffed and blocked, I couldn't beg Brandon to help me either.

I think maybe Brandon had seen women in this predicament before. He let me stew at the edge of release for a while longer with just the stimulation in my ass to work with, then he reached his other hand under me and started flicking my clit with a fingertip. That was what I needed. A minute or two of that and I came in a sudden rush of explosive pleasure. My rectum clamped down hard on the paddle handle as if it was trying to force it out, but Brandon held it tightly all the way in. "MMMMMPPPHH!" I screamed into the gag.

I would have collapsed exhausted onto the bed if the ropes hadn't been holding me in my doubled-up position. Brandon let me lie there and pant through my nose while I came down, hands balled into tight fists from the intensity of the experience. Then he slid the handle out of my ass, for which I was glad. All of a sudden my ass was really tired of being assaulted by a cylinder of wood.

OK, I thought to myself as I recuperated. He hasn't gotten his own rocks off yet. Where's he going to decide to put that cock? I doubted that he would want to take the gag off and listen to me ream him out for not keeping his word on boundaries. That left my ass and my pussy. Please, not my ass, I begged in my mind. Not after what you just put it through.

I would need to wait a bit longer to get my answer. He wasn't through hitting me with things yet. He put the paddle aside -- maybe he was tired of it, or maybe he just didn't want to grip the handle after he'd shoved it all the way up my ass -- and he started looking through the drawer for inspiration. Thank God I hid the single-tail and the cane, I thought. This is exactly why I always do that with a new dom.

I was relieved when he came back with my riding crop. You can really make someone hurt with one of those if you put your mind to it, but it's pretty hard to do lasting damage.

His smacks with the crop were like his smacks with the paddle -- harder than I would have liked, but nothing I couldn't push through and find some pleasure in if I really worked at it. As he worked over my ass, thighs and back again, I could feel orgasm number two starting to stir. I bit down hard on the ball in my mouth and concentrated on those sensations, nurturing that transformation of pain into pleasure. My pussy started juicing again, and I could smell the scent of my arousal beginning to intensify.

Then it got worse. He took me by one ankle and turned me over so I was lying with my feet in the air and my breasts and pussy in full target range. He knelt with his knees between my ankles to make sure that my legs stayed apart, and then started systematically using the crop on one nipple, then the other, then my pussy lips. He was indeed an experienced dom -- he obviously knew exactly how sensitive those areas are, and he was flicking rather than smacking. Still, he was setting off big rockets of pain that I had to work really hard to transmute into pleasure.

Fortunately, this stage didn't go on very long. Now that I was on my back, I could see the bulge his cock was making as it strained against his pants. Giving pain obviously turned him on as much as receiving it -- usually -- did me. He seemed to agree with me that it was time to move this scene along, so he got off the bed and shucked his pants and underwear down with one motion. As soon as his penis was free, it sprang into an erection so hard that it was almost vibrating. And, just as I feared, it was really, really big. Now, I like big cocks as much as the next gal, but they need to be deployed very delicately if they are going to do their job without really destroying the hole they're in. I very much doubted that Brandon would be delicate.

With me in this position, he could have picked either hole, so I was relieved when he parted my labia with his fingers and started to press his cock against the opening of my vagina. Then he stopped, thought a minute, and returned to the drawer. Oh God, I thought. What the fuck is he up to now?

He came back with a small clamp designed for nipples, labia, and other sensitive parts. He also had a small cordless vibrator and a roll of tape -- not skin-friendly bondage tape, I noted, but plain old-fashioned duct tape. (Why the hell had I even left that in the drawer now that I've discovered bondage tape, I asked myself.) He put the clamp on my engorged clit, causing another rocket of pain/pleasure to shoot through me. He turned on the vibrator, touched the end to the clamp so the entire clamp was vibrating, and secured the whole affair with several strips of tape across my abdomen.

The effect was electrifying. My clit, already aching for some stimulation, went off like a bomb from the vibrations. My arousal soared another notch when he pressed his cock against my vaginal entrance again and started to push it in. As my cunt was stretched out more and more by his thick cock, I started making pre-orgasmic grunts through the gag. He began pounding relentlessly, pivoting on his knees and being careful not to rub against the top part of my pussy and dislodge his makeshift vibrator system.

Finally I let out another muffled orgasmic scream and came violently. The scream, and maybe also my vagina clamping down tightly on his cock as I came, seemed to set off his orgasm as well. He blew what felt like a huge load of cum way into the depths of my body.

He pulled his cock out and laid beside me on the bed, obviously as exhausted as I was. Then he stood up, wiped himself off with a tissue, and pulled his pants back on. He didn't bother to do anything about the stream of cum that was leaking out of my pussy and pooling on the bed, which for some reason enraged me even more than his other contraventions of the dom/sub ethics of conduct. It just seemed so -- so -- I don't know, crass and thoughtless.

He gave me a quick kiss on my gagged mouth, said. "That was great, babe. Thanks for the wonderful visit," and turned to leave. I went rigid with fear. Fuck! Was he really going to leave me tied up and totally helpless like this? I hadn't prepared a backup plan the way I usually do, setting up a friend to check on me if I didn't get back to her within four hours. I could be trapped here for days. Shit, I could die here!

Then I got a grip. I could eventually squirm to a phone and speed-dial Shelly's number. Even if I couldn't talk to her, she'd see my number and hear my gag-talk in the distance, and would know it was time to let herself into my apartment and check on me. But I really didn't want to put my theory to a test. I screamed desperately through the gag and waved my bound legs in the air.

Brandon turned and laughed, then came back over to me. Bastard! He'd never really planned to leave me tied up and gagged; he was just messing with my head.

He undid the knot on the rope holding my right wrist to my ankle. He didn't unwind the many turns of rope or undo anything else. Then he really did walk out. As he closed the door behind him, he said, "See you around, Babe. Have a nice rest of your day." So much for after-care.

What an absolute fucking asshole. But there wasn't a lot of point in lying there raging. I had a job ahead of me. Normally, once the main knot was undone, I would have been able to slide my hand out of the loosening coils of rope. But the second set of ropes pinning my forearms to my legs prevented that maneuver. I was sure that the asshole had planned this too. I wiggled at the ropes for quite a while before I gave up and tried another approach. There wasn't anything holding my legs apart, so I could bring them together and use my still-bound left hand to pick at the ropes holding the right one. Once my wrist was finally free, the upper set of ropes still made it really awkward to do anything with my right hand, but I was able to pick apart the knot on my left wrist and get it free the same way. I had to fold myself into even more of a pretzel to get my hands high enough to get at the upper set of ropes, but I eventually managed it. All in all, it took me over an hour to work myself free.

I unbuckled the gag and pulled the saliva-covered ball out of my mouth, noticing that it had bite marks in it from the intensity of the orgasms. I inspected the helical pressure marks the rope had left. Another flashback to my good friend Nick, who had left me in a similar state on the beach at the resort. Then I got off the bed shakily and inspected my back in a full-length mirror. Apart from some bright red areas and a few minor bruises, I didn't seem to be in too bad a shape, considering.

I peeled off the vibrator, removed the clamp from my clit (OWWWW!) and wiped the worst of the cum off my legs and pussy, then sat down (carefully) on the bed to take stock. Brandon had taught me that my pain threshold is higher than I had thought, and so is my ability to transmute pain into pleasure. I had had two crashing orgasms brought on partly by my helplessness and the degree of indignity he was able to dish out. I also realized that in some really strange way, the total helplessness of non-consensual sex was exhilarating at the same time as it was enraging and frightening.

On the other hand, even though I now knew that I hadn't been in any real danger, I certainly could have been. Brandon could have really harmed me in any way he chose, even killed me. Even worse in some ways, he had violated the bond of trust between dom and sub that makes BDSM work. If you're going to put yourself in someone's power, you absolutely have to trust that the boundaries you have set will be respected, that your safewords will work, that the dom won't take any more advantage of you than you are willing to submit to. Without that trust, the whole arrangement collapses. I would never, ever forgive Brandon for that, mind-blowing orgasms or not.

I considered my options. I could just write it off as the cost of doing business as a sub. I'd had some bad dates before, although none quite as bad as this one. But I really didn't want him to repeat his performance with other women. I could probably get him banned from every dating site on the entire internet -- those folks are careful about their reputation, and if it got around that they were letting guys like Brandon abuse their customers' trust this badly, their "at your own risk" fine print might save them from legal action but it wouldn't save them from losing customers. I resolved that, by the end of the week, he'd be totally out of the internet BDSM dating community. I would also post warnings, with his name and picture, on popular BDSM blogs. He's going to have to work a lot harder to find victims after that.

And for myself, I resolved to improve my vetting procedure. The most sinister aspect of Brandon the Asshole had been how perfectly convincing his good-guy act had been. That, I told myself, was not going to happen again.

4. One More Try

I swore off internet dating for a while, consoling myself with my various toys. But eventually the itch started to come back. You'd think Brandon would have turned me off forever, but I guess I was addicted to the sense of adventure. I got some kind of perverse thrill out of setting up scenes with total strangers, even though I knew the dangers.