Allyson’s On-Line Dates

Allyson’s On-Line Dates

Author’s Note: This story is a side-story to the Kev and Kendra series, featuring the woman who was introduced as their bondage partner in “Kendra at the Beach,” and is set several weeks after that story. I’ve tried to make it possible to enjoy this story without having read the previous one, although you might want to go back to “Kendra at the Beach” first if you’re a stickler for doing things in order. There are quite a few back-references.

Content warning: The bondage and pain play in this story is mostly consensual, but it does take a short side-trip into non-con in the middle.

1. Allyson is Missing Something

I had been back in Ann Arbor, Michigan for three weeks or so after returning from the island vacation where I’d met and played with Kendra and Kev. As I contemplated Michigan’s February weather, I badly missed the warm sunny beaches of the island. I also missed the open, bondage-positive atmosphere of the resort, where nobody cared if you wanted to fuck in handcuffs stark naked on the beach. But mostly I missed Kendra and Kev. They didn’t share my enjoyment of pain play, but they were more than willing to go along with it by including some flogging (of me) in our three-way bondage sessions. They seemed so balanced and genuinely kind, unlike some of the people I’ve met in the BDSM world, and they were always willing to teach me new things like urethral sounding (not my cup of tea, it turned out) and electosex (very much my cup of tea — I was having trouble waiting for some of the new electro toys I’d ordered).

I had a standing invitation to visit them in Toronto, but being cursed with that necessary evil of modern life, a job, I couldn’t just pack up and go to Canada every time I felt horny, even though the pandemic border restrictions were starting to ease. Instead I spent a lot of time with my toy collection. One night I got comfortable naked on the bed and applied the nipple and labia clamps that Kendra and Kev had given me as a parting gift when we left the island. I had the adjustment screws tightened all the way, and shit, those things really hurt when I put them on my nipples. I felt the sweet tingle of incipient orgasm starting to run through my body already. The labia clamps didn’t hurt quite as much, but they certainly added to the total effect, especially when I tightened the central chain that held the two pairs of clamps together. The feeling of my tits and my pussy being pulled relentlessly toward each other was hugely erotic, and my pussy began to run with juices.

I had recently treated myself to a new high-tech vibrator. The body slid into my cunt like the usual vibrating dildo, but it also had an extension that came up through my pussy lips to my clit. It featured a bump about the size of the end of a little finger with a small hole in the middle. It fit perfectly over my clit, sealing nicely to my wet pussy-skin. When I turned it on, the extension began contracting and releasing in a very good imitation of a pair of lips sucking me right where I love to be sucked. I couldn’t move the body of the device in and out of my cunt to fuck myself with it, but I didn’t have to — the powerful vibrations, combined with the sucking action, were doing an excellent job of ramping up my orgasm.

I held the centre chain on the clamps and pulled it away from my body, intensifying the pain that was combining with the sensations in my pussy to set my nervous system on fire. I began to thrash involuntarily on the bed, thrusting up with my hips as if I had another human being on top of me to thrust against. I rhythmically yanked on the chain, matching the rhythm of my thrusting hips and trying not to pull so hard that the clamps popped off my wet, slippery pussy lips. I thumbed the vibrator to its highest setting and clutched the bedclothes in a death grip with the other hand as the spasm of orgasm swept over me. I made a long, guttural scream, then collapsed back on the bed in blessed release.

I turned off the vibrator and slid it out. I slowly released the clamps one by one, feeling the rush of intense pain as the blood flooded back into the places they had been. The pain was the perfect dessert for my play session.

Just one problem. The fancy vibrator reminded me too much of Kendra’s lips on my clit and Kev’s cock in my pussy. It wasn’t so much them specifically that I missed, although they had been my latest, and in many ways my best, sex partners. I mostly just missed all the things another human being could do to me that were hard to do to myself. It just didn’t work that well to hit myself with a flogger, a riding crop or a paddle. I had tried self-bondage a few times, but even with vibrators in my ass and pussy, it seemed fake compared to having someone actually tie me up and fuck me.

The message was obvious. It was time to see if I could pick up a BDSM playmate.

I had tried picking people up in fetish clubs before, but I really didn’t want to go there again. Most of the people in those clubs arrive in pairs, and the ones that arrive as singles tend to be kind of odd, if not downright scary. I had hooked up with needy people who simply wouldn’t leave me alone, with insecure people who couldn’t seem to get into the spirit of casual sex and bondage, and worst, with people who turned out to be borderline psychos. A couple of times I felt myself in genuine fear for my life. I always tried to start out by playing in the relatively safe public space of the fetish club before taking a partner home or going home with them, and then only after knowing them long enough to be fairly sure I could trust them — D/S is, after all, all about the element of trust that you have to have before putting yourself in another person’s power. But a few times I had slipped up. A prime example is Nick, the delightful man on the island who left me on the beach in the sun, naked, gagged and tied to a St. Andrew’s cross for hours until Kev and Kendra rescued me.

I decided to try a different tack — on-line dating services. Of course, people present a false identity on those all the time too, but I figured that the convention of texting back and forth for a while — perhaps quite a while — before meeting in person would give me a better chance of filtering out some of the less appealing ones.

I looked at myself carefully, naked, in a full-length mirror. For a woman in her late thirties, I honestly assessed myself as being still a pretty good catch physically. Somewhat petite at 5’4″, my body is well-muscled from regular workouts and at the time still sported the remains of the all-over tan I’d brought home from the Caribbean. My hair is long and lush, dark brown like my eyes, my breasts medium sized and firm, my hips slender and my shaved pussy fairly prominent but with small inner lips that don’t protrude. I propped my phone on the dresser and took a timed selfie to save for times when exchanging nude pictures would be appropriate. Then I dressed in a more safe-for-work but still sexy red dress and took another picture that would be appropriate for my profile. I tried to cultivate a facial expression that said “fuck me” without saying “I’m desperate.”

Some dating sites were pretty coy about what you were allowed to say about what you wanted to do. On one, I opened right up about my love of bondage, pain play and anal sex, and found my profile deleted by the next morning. I discovered that the most explicit I could be was “non-vanilla.” That got the attention of other non-vanilla people, and we could sort out exactly what each other meant by that in our back-and-forth textual foreplay.

Other sites let you check off exactly what you were into, which saved some time, although I found that it was still really important to unpack exactly what each other meant by terms. One person’s definition of “pain play” could be wildly different from another’s, as could their definition of “consent.” I see consent as a constantly evolving phenomenon in which the dom checks in with the sub every step of the way to make sure they’re still ok with what’s going on or about to go on. Some doms I’ve dated seemed to think that if I consented to bondage sex at the beginning, I was consenting to everything they wanted to do to me. For me, that’s a guarantee of a one-and-done date.

I started in. I was amazed at the flood of responses I got within hours. I guess women who broadcast that they’re interested in casual BDSM sex aren’t all that common on dating sites, and attract men like flies to honey. Women too, since I’d indicated an interest in either, although there didn’t seem to be nearly as many women as men looking for a sub on line. I’ll let people more versed in psychology than I am figure that out.

I found it just as hard as I expected to size up a man’s personality from a picture and a few paragraphs of self-description, but I found that I could eliminate some right away. I tried not to let looks drive my search too much. Of course it would be nice to start dating a beautifully muscled hunk who looked as though he could be a contender for the next James Bond, but I’ve found by experience that men like that have a bad habit of being over-aware of how good they look and don’t try very hard to cultivate other, more subtle traits — like treating a woman as a fully realized human being rather than as a cunt on legs. Also, I figured that they would be swarmed by other women on dating sites. I could also eliminate men whose profiles showed no real interest in BDSM (or “non-vanilla” sex), who seemed to be looking for a long-term committed relationship — not that I would turn up my nose at that, but I didn’t want to be pushed in that direction right away — or who seemed to be looking for a mother figure to look after them and keep them psychologically warm and cozy.

I also eliminated men who seemed to think that the first thing a woman wanted to look at was their junk. Now, I love the feel of a penis inside me, but listen, guys, it’s really not a very photogenic piece of apparatus. One guy displayed the hugest dick I’ve ever seen, obviously Photoshopped — or at least I hoped it was Photoshopped, for his sake. Otherwise he would be spending most of his life looking for a woman who would let a monster like that in any of her holes. Swipe left.

Others got eliminated after a few exchanges of text that clarified what they meant by “bondage” or “pain play.” Case in point:

“Hi Jason. Your profile says you’re interested in BDSM. Exactly what does that mean to you?”

“I love to put a woman in severe bondage and hit her with things.”

“Exactly what do you mean by ‘severe’?”

“Well, I tied my previous playmate face down on the bed and whipped her with a single-tail until her back was covered in red welts. Then I wrapped her completely from head to toe in microfoam tape.”

“And then?”

“Then I dumped her in a box, jacked off all over her, and then shoved her under the bed for the rest of the night.”

“And what did she think of that?”

“Dunno. Didn’t ask.

“Just felt great to know I was sleeping on top of her and that I could slide out the box and do whatever I wanted any time I wanted.”

I could see why she was a “previous” partner. He had made it onto my “no” list by the time he finished being so delighted in marking her up, but “didn’t ask” was the total deal-breaker. I ghosted him then and there.

2. Charles the Clueless

One guy intrigued me. He wasn’t exactly handsome in the James Bond sort of way, and he certainly couldn’t be called “rugged.” He looked quite slightly built, but in a healthy sort of way. His picture looked back at me with a sort of wistful expression that I found oddly charming — in most of the pictures, the men tried for a sort of commanding look that I thought just made them look too full of themselves. He gave his age as twenty-three, which seemed roughly to accord with the picture.

This guy, who said his name was Charles, hit all the right notes in his profile. He said he was interested in tying a woman up, hitting her with a riding crop and spanking her with his hand or with a paddle, and having sex with her in all three holes. That pretty much ticked all my boxes, although I thought the expression “interested in” seemed a bit odd.

Charles seemed close enough to the mark that I swiped right and started an exchange of text messages.

“Hi Charles. Tell me exactly what you think you’d like to do to me.”

“I’d love to tie you up doggy-style with your ass in the air and then spank your ass with a paddle.

“I’d love to gag you, too. That’s always been a fantasy of mine. But prob a bad idea until we know each other better.

“I need to be able to check in with you and make sure I’m doing it right.”

Hmm. I kind of liked the attitude he was projecting. But something still seemed a little off.

“What did you mean ‘a fantasy of mine’?”

“Well, actually, I’ve never really done this kind of thing before. But I’ve always wanted to. I was hoping for someone who could show me how it’s really done.

“I doubt porn gives a very accurate picture.” <smile emoji>

Well, that was refreshingly honest, at least. He was certainly right about the porn. Learning about any kind of sex from porn is kind of like learning to drive by watching Fast and Furious movies.

“What exactly have you done?”

“Well, I’m not a virgin, if that’s what you mean. I’ve just never had the chance to tie someone up before I fuck them.”

“You mentioned ‘all three holes.’ Do you like jacking off in a woman’s face after a blowjob?”

“Not really. Seems messy, and I can’t imagine anyone liking it.

“But I could do it to you if you liked it.”

This was getting better and better, in its weird way. He seemed to be giving what I wanted at least equal billing with what he wanted.

“What about fucking a woman in the ass. Ever done that?”

“Sure I have.”

Hmmm. Zero details. Might be an empty boast. But I was really intrigued by the sound of this guy. It might be fun to coach a newbie rather than deal with a hard-core dom. As Sean Connery said in The Untouchables, “If you don’t want a bad apple, don’t take it from the barrel. Pick it from the tree.”

I decided to skip the dating niceties and get down to business. I invited him to my place the following evening. In some ways I would have preferred not to let him know where I lived right away, but at my place at least I would have some control over the toy collection. I went through my toy drawer and took out the single-tail whip and the cane. Both of those could do a lot of damage in the wrong hands. But I left the multi-tail flogger, the riding crop, and two paddles, plus all my various restraints, vibrators and butt plugs. There wasn’t anything there that I wouldn’t enjoy as long as Charles was receptive to being told how to use them.

When he arrived, he seemed pretty much as advertised. Slightly built but not gangly. A bit shy, but also eager for some adventure. We made small talk over a drink so he could relax a bit — but just one. Safe BDSM requires a clear head.

Then I took him by the hand and walked him to the bedroom. I opened the toy drawer, and his face was priceless when he looked in. I doubted that he had ever seen such a collection close up before. His previous partners probably had a vibrator or two, maybe some handcuffs, and that was that. He picked things up one by one and examined them. When he came to my four-cuff spreader bar, he seemed to know exactly what it was. “I’d like to use this if it’s OK.”

If it’s OK. This guy was utterly charming in his tentativeness. “If it’s in that drawer, it’s something I like.” He seemed to be having trouble figuring out the thumbscrew in the middle. “Undo it a little. Now pull.” The spreader telescoped from its half-metre storage position to its full get-down-to-business length of almost a metre. He got a delighted grin on his face as he tightened the screw back up again. I guessed that he had a thing for gadgets.

He stood there for a few beats, not seeming to know what to do next. We didn’t bother with kissing. Neither of us had known each other long enough to feel any affection, so it would have been a pretty empty gesture. I just helped him out by pulling off his shirt, unbuckling his pants, and pulling them and his underpants down to his ankles. I helped him get the legs over his feet as he stepped out of them. His cock was already hard in that magic way young men have of being able to pop an erection any time, any where.

I crossed my arms and pulled my shirt off over my head, then turned my back to present my bra clasp. He hesitated a moment, then caught on and unhooked me. As it slipped off onto the floor, he cradled both my breasts from behind in his cupped hands and felt my nipples gently. He didn’t seem unsure, but he didn’t seem overeager either. He savoured them instead of mauling them the way some guys do, as if they hadn’t seen tits in years.

I turned to face him again, and he pulled my elastic-waist pants down and followed them with my panties. He helped me step out of them the way I had done with him. When he straightened up, he stood back and unapologetically admired my body for a minute, then reached out and cupped my shaven pussy the way he’d done my breasts. He slipped a finger between my lips and just held it there. He didn’t act as if he’d never seen a naked woman before, but he was certainly enjoying the look and feel of one right now.

He didn’t seem very sure where to take this from there, so I made the next move by climbing on the bed. I got on my knees doubled up with my ankles obligingly spread about a metre apart and my wrists between them. He laid the spreader bar across the bed under them and began fastening it. He had a bit of trouble with the first quick-release fastener, but he figured it out quickly and had no trouble with the other three. I wiggled my hands and feet — just right, snug without any danger of cutting off circulation.

He rummaged in the drawer for another minute. He held up the ball gag with the leather mouth cover and looked at it longingly, but put it back. He selected a short-handled riding crop and stood behind me next to the bed. Again, he seemed unsure of what to do next.

“Imagine a fly just landed on my ass. Now swat it.” He did that, kind of lightly for my taste. “That’s the spirit. Try it a little harder.” This time the crop came down hard enough to really smart. Closer.

“Do it from the wrist rather than your whole arm. You’re swatting me, not walloping me.” He tried again. Just about perfect — a really good, sharp sting without the follow-through that would have driven me forward in the cuffs. I let out a little yelp of mixed pain and pleasure. “You’ve got it. Just keep doing that.”

He laid a dozen or so more on me. I could feel my ass start to burn. “Keep moving around. Don’t wear out one spot.” He did that, laying into me for at least twenty minutes. I was in heaven — I hadn’t had a good flogging since I’d left the island, and the way the pain mingled with pleasure was intoxicating.

Finally he stopped. Maybe he was running out of places to hit me, or maybe he just wanted to move on to his next fantasy. He got on his knees behind me on the bed and started massaging inside my very slick pussy. He moved up and down, rubbing rapidly and firmly, but never seemed to get as far as my clit. After a few minutes of this, I said, “Don’t forget to give my clit some attention.” He stopped, seeming puzzled. “You do know where my clitoris is, don’t you?”

“Umm — isn’t it up inside?”

I fought down the impulse to giggle. This guy hadn’t really done anything do deserve having his balls, and his self-esteem, broken by being laughed at. Still, I thought, what the fuck do they teach in sex ed these days? Anything beyond little sperm swimming up to little eggs? Even if they weren’t progressive enough to have a unit on “How to Give a Woman Pleasure in Bed,” they must have had those medical-looking line drawings of male and female sexual apparatus. That’s how I found out exactly how I was put together in the places I couldn’t see. Maybe he slept through that part.

“No, it isn’t,” I said in what I hoped was a neutral and non-sarcastic tone. “Find my vagina.” He did, slipping a couple of fingers into it in ways that I didn’t object to at all. But I hadn’t finished my sex ed lesson. “Now slide your fingers up.” His fingers started moving in the direction of my asshole. “Sorry, I forgot I’m face down. I meant the other up.” He started back in the other direction, sliding over my nearly invisible peehole without seeming to notice it. Maybe someday I’d give him a lesson on how that works — he probably thought women pee through their vaginas — but I figured one body part at a time would be enough for him to take in.

“Right there. Feel that little nub? That’s my clit. It’s the most sensitive sex part I’ve got, and it loves to be rubbed, licked, sucked, or whatever you want to do. I won’t be able to cum if you don’t give it some love.” He obliged, rubbing and fondling with his fingers. He caught on quickly, and seemed to be able to read my body for signals to see when he was getting it right. I felt an orgasm coming on nicely.

“Now I see why most of my other partners didn’t seem to get off that well. Nobody ever told me about this.” I silently cursed those former partners who couldn’t be bothered to enlighten this eager student of the female body. He scootched closer and positioned the tip of his cock against my asshole, keeping his finger on my clit.

“Hold on, sailor. Haven’t you forgotten something?”

“Condom? But I thought we agreed…”

“Lube.”

“But everything’s so slick already. I didn’t think you’d need more.”

I closed my eyes so he wouldn’t see me roll them. “You fibbed to me when you said you’d done this before, didn’t you?”

He was silent for a minute, then stammered, “I didn’t want you to think I was a total amateur.”

“Listen, one of the secrets of good sex, especially kinky sex, is telling each other everything. That means absolutely everything. But don’t worry. I said I’d walk you through this, and I will. Here’s the thing. Pussies make their own lube. Assholes don’t. They’re not really designed to have things stuck up them, although it’s fun to repurpose them.

“There’s a bottle of lube in the drawer. While you’re in there, grab the long skinny vibrator. I like being fucked in the ass, but I can’t usually cum from it all by itself. My clit’s too far away from it. But add a bit of vibe, and I’m over the edge right now.”

He got the lube. “So, put a whole bunch of lube on your cock and a bunch more on my asshole. There’s no such thing as too much where assholes are concerned.” He did. “OK, now start working your cock in. But listen. If I say stop, that means stop, right now, and wait for me to tell you to go ahead some more. Otherwise I’ll have a spasm that’ll leave me in agony for at least five minutes. Remember that you’re using it for a purpose it wasn’t designed for. Go easy.”

Jeez, kids these days. An internet full of free porn, and even reliable self-help sex guides, and you still have to tell them everything. Come to think of it, though, I’ve hardly ever seen people use lube in porn flicks, aside from maybe a bit of spit. I guess they think it isn’t very sexy, although they obviously lube up off camera. It wouldn’t be hard to miss how essential lube is to anal sex.

He hesitated — I think I scared him. “Go ahead, don’t worry. As I said, I’ll talk you through it. If you listen to me, you won’t hurt me.”

He pressed the tip of his cock against my sphincter. As always, it resisted a bit. “That’s good. Keep pressing. It’ll slip in.” It did, and with only a little stop-and-go, he got it worked all the way in and started thrusting slowly and rhythmically. There was a little pain just at the point where his cock first pried my sphincter open, but my asshole quickly settled into its job of gripping him firmly as he slid inside it.

Between the pain play and now a cock filling up my ass, I was starting to feel really fine. I love having a cock in my ass. A toy feels good, but nothing compares to the warm sensation of a human body part responding to my body, stretching me out and massaging my G-spot from the inside.

“OK, now turn on the vibe and press it against my clit.” I resisted the urge to say, “You do remember where my clit is, don’t you?” If I’d wanted to humiliate him, I could have done it long ago, but I was having a good time and I didn’t want to end it by being a sarcastic bitch.

He got the vibe positioned and went back to thrusting, first slowly and then gradually accelerating. I could feel my tits rocking back and forth as he thrust my body rhythmically forward. The bondage, especially the spreader bar keeping my legs forced wide open, intensified the building pleasure, and rhythmic yelps of pre-orgasmic bliss started coming out of my mouth with each thrust. The sensation radiated from my clit back into my stretched-out rectum until my familiar guttural scream ripped out of my mouth and I felt my whole abdomen, from my uterus down through my cervix and vaginal walls, clench and convulse in the best orgasm I’d had since leaving the island.

He stopped, waited for me to come down a little, then made several final rapid thrusts and filled my ass with warm cum. He pulled out slowly, the sensation of his cock-head sliding back through my rectum and past my sphincter feeling almost as good as having it in there. I felt a little river of cum drip down onto the towel I’d spread on the bed. I relaxed in my cuffs, breathing gently and savouring my post-coital bliss. He laid down and rolled onto his side to face me, and I turned my head in his direction. “Well, how’d I do?”

It gave him a warm smile. “Considering you’re a first timer at this, you did great. That was one hell of a mind-blowing orgasm you gave me. You listened to me and did exactly what I asked you to. That’s not nearly as common as it should be.”

“That was fantastic for me too. God, that was tight! I’ve never felt anything quite like it.” He thought for a minute. “Do you want me to let you go now?”

I smiled. “Fuck, no. We’re just getting started. If you’re not tired of this, of course.”

He smiled back. “Fuck, no.”

“OK, then. Let me show you some stuff. First, hit the bathroom and clean up, then get back here.” As he started to head off, I added, “And bring a wet cloth for me, too.”

He came back a couple of minutes later with a wet, soapy cloth and cleaned his cum, my juices, and a trace of shit off my pussy and asscrack. “Now help me turn over.” He held the ends of the spreader and twisted them in opposite directions. I flipped over and ended up on my back, my feet pulled up in the air by my arms that were still attached to the cuffs in the middle of the spreader, my pussy still spread but now facing up in an even more obscene display. “Now, scootch around so your knees are straddling my head. Look down. See what your mouth is pointed at? I told you all the things my clit likes. Why not try some more of them?”

This young man may have been inexperienced, but he caught on quickly. He brought his mouth down and started licking and sucking my clit vigorously. I leaned back with a grin on my face, enjoying the feel of his tongue as it explored places I figured it had never been before. I started breathing more and more deeply as the orgasmic tingle began to rebuild in my body. Yes, real lips, even inexperienced ones, are better than my sucking vibrator.

“The clit’s the best part, but don’t neglect the rest of it. It’s all good.” He ran his tongue down and played with the entrance to my vagina. Then he noticed the tiny hole almost hidden just above it, and explored it with his tongue.

“That’s my peehole. It’s not quite as erogenous as some of the rest of it, but it really likes attention too.” I really should have been getting an honourarium from the Board of Education for filling in all the missing bits of Sex Ed. But I really didn’t care — his eager tongue and lips were honourarium enough right then. He went all over every part of my pussy, exploring like he had just set foot on an undiscovered continent. He was amazing in his exploratory enthusiasm. Now that I’d introduced him to it, he played with my peehole with his tongue, sending little waves of pleasure up my body. Kendra had tried to turn me on to urethral sounding, and I had quickly decided that, unlike hers, my peehole does not like things up it. But that doesn’t mean that, now that I’m aware of it as another erogenous part, I don’t love having it stimulated from the outside.

My body built to another orgasm, not quite as mind-shattering as the first one, but intense and satisfying nonetheless. As I came down and my breathing slowed, I noticed that, as you’d expect, his cock was dangling in front of my face. It was getting hard again already, so I said, “Your turn. Bring that thing down to my mouth so I can give it a good time too.” I took the tip in my mouth and started running my tongue over it. He stiffened and his breath caught, and he began rocking his hips back and forth, pushing his cock in a little farther with each stroke. At that point he started neglecting my pussy completely, but I didn’t mind. I don’t multi-task well myself, and now that he’d pushed me over the top a second time, I was content to have us both concentrate on his pleasure for a while.

We both started gasping rhythmically, and his semi-hard cock quickly turned into a crowbar. I lunged my head upwards and took him all the way down my throat, which produced a quiver of mingled shock and delight — I couldn’t really see his face from that angle, but I didn’t have to in order to know what he was feeling. I’m sure he’d had his cock sucked before, but likely not this deep, and almost certainly not by a woman securely restrained in a spreader bar.

At first I managed the face-fuck, bobbing my head up to push his cock down my throat until his balls bumped my nose. Then he gradually took over the rhythm, rocking his hips to drive his cock down my throat while I laid back on the bed. I gripped his cock with my throat muscles to give him some extra simulation while he pumped. The feel of his cock sliding in and out of my throat was exhilarating, almost as good as having it in my pussy or my ass, and our 69 position put it at just the right angle. I have never had a very strong gag reflex, and a few years ago I spent weeks practicing with gradually longer and fatter dildoes until I had learned to relax my throat enough to take almost anything down it. Comes in handy, considering the style of recreation I’ve taken up.

Then I ran into a problem. He was having such a good time throat-fucking me that he started forgetting to pull back enough for me to take a breath. I kept waiting, sure he’d pull back any second, but he was oblivious. I had to work hard not to panic. I made loud gagging noises and started to struggle wildly, and all of a sudden he caught on. He yanked his cock out and looked at me with alarm as I coughed and sputtered.

When I’d gotten my breath back, I said, “Look. I love having a cock in my throat. But it’s not like a cunt that you can leave your cock in for as long as you want. Get a rhythm going — stroke, breathe, stroke, breathe. And when you cum, feel free to cum in my mouth, but make sure you pull back out of my throat or you’ll really drown me. Now let’s give that another try.”

He was a quick study. Sometimes he’d pause at the bottom of a stroke to savour the tight grip of my throat, but never for more than a few seconds before he pulled right back so I could snatch a couple of breaths. I rewarded him by doing nice things to his cock-head with my tongue whenever he pulled out of my throat.

His orgasm built more slowly than the first one had, but I felt his breathing deepening and becoming ragged. He held my hips tightly for support as he rocked his body more and more forcefully, until he finally let loose a drawn-out throaty noise and shot warm cum into my mouth. I swallowed and licked the end of his cock as clean as I could with my tongue before he rolled over beside me, exhausted.

“That was positively, absolutely wonderful. I’ve never been throat-fucked like that in my life. Thank you. And I’m sorry I tried to smother you.”

I smiled. “Well, you caught on before I had to bite down on your cock. That’s what matters.” He didn’t look very pleased at that suggestion, but I didn’t mean it as a joke. It would have been my next move if he hadn’t pulled back when he did.

“Well, this has been a wonderful, and educational, evening. Thanks for being so patient with me. But I think I’m done. That was a hell of a workout. I hope we can do it again some day. I retain lessons well, and I’ll bet you have some more up your sleeve for next time.”

“Maybe next time I’ll show you how to use a six-tail braided flogger.”

He flicked the quick-release snaps open so I could take my wrists and ankles out of the spreader, and I straightened my cramped knees gratefully. Then I put my arms around him and gave him a long, tongue-y kiss. It wasn’t love, but I felt genuine affection for this naive guy who was so eager to learn how to please me. It brought out a sort of perverse mother instinct in me. I certainly could have done lots worse.

As I would soon find out.

3. Brandon the Asshole

A few days later, my scene with Charles had worn off and I was starting to feel horny again. I could have texted Charles to see if he was up for a repeat, and I likely would do so eventually. After all, I’d promised him a flogger lesson. But, despite the attractiveness of his thoughtful attitude and his willingness to learn, he was a bit exhausting to deal with. I wondered if I could find a dom whom I didn’t have to lead by the hand through every step. I started swiping again.

I had deliberately avoided going into my apps for a few days, and I was astonished at how many matches had built up. I flipped through them quickly, eliminating the dick-pics and obvious non-starters, but I still had a job ahead of me.

Finally I got down to four or five who looked promising. One, Brandon, described himself as an “experienced dom.” He put a lot more detail into his profile than most people did, and the kinds of detail he used suggested that he was, indeed, experienced. He listed the various impact devices he was allegedly expert with, including single-tail and double-tail whips, multi-tail floggers, flicker whips, tawse, violet wands, and even cattle prods for more extreme masochists. He listed his talents with rope bondage and other types of restraint, and said he was especially fond of spreader bars and suspension. He didn’t much care for the more painful sorts of restraint like armbinders and reverse prayer — nor do I. I like my pain to come from impact, not stress positions.

He explained his views on consent in some detail, and they accorded perfectly with mine. He even mentioned the importance of after-care to help a sub down from subspace if that’s where they ended up, or just to decompress from an intense experience. I hadn’t seen that in any other profile. It’s definitely not something you would pick up from porn. I was reading a very professional-sounding profile here.

“How hard do you like to hit a sub?”

“Exactly as hard as she likes. Some like it light, some like it heavy. The sub calls the shots.”

“Do you like fucking a woman once you’ve tied her up and given her some pain?”

“Nothing better. The impact play gets me super horny, and usually her too. If it doesn’t, I’m doing something wrong.”

“Breath play?”

“No. Way too easy to kill someone by accident.”

“Gags?”

“Love them. A woman isn’t properly tied up if she doesn’t have something in her mouth. But only if we’ve worked out a good set of signals. Gotta know how she’s doing, if I should ease up or go harder.”

“Have you ever left marks on a sub?”

“Exactly once, back when I didn’t know what I was doing. Took a week or two to fade. Now, the worst I leave behind is maybe a red ass.”

I liked where this was going. He seemed to have all the angles on safe, consensual BDSM. I was even more inclined to believe what he said about being an experienced dom — he knew all the rules, written and unwritten, and sounded as though he prided himself on following them. And he didn’t seem to mind being grilled by a potential sub. That was appropriate, I thought, since I was the one who would be surrendering power to him, not the reverse. We had a date.

When he arrived at my door, he was everything Charles wasn’t — tall, imposing, with a neatly trimmed dark beard and a manner that was self-assured but not domineering. He was wearing jeans and a denim shirt with a leather vest — just enough dungeon ambience to look the part without looking silly walking down the street. I felt like my gruelling vetting sessions were paying off.

After our ritual get-to-know-you drink and chat, I didn’t detect anything that contradicted my first impression. I showed him into the bedroom and opened my toy drawer. I had hidden the single-tail and the cane again, even though he claimed to be expert with them. Unfortunately, I hadn’t hidden the gags.

He seemed impressed, but not astonished the way Charles had been. He took out every toy one by one, inspected them, and laid them out neatly on the top of the dresser. He paused with a handful of bondage straps in his hand.

“Do you have any suspension points in here?”

“Sorry, no. I’ve done suspension in fetish dungeons and enjoyed it” — here I thought of the dungeon I had shared with Kev and Kendra on the island — “but I don’t have that sort of equipment here.”

“Pity. If we do this again, I can bring over a stud finder and some sturdy hooks for you if you want.”

“I’ll let you know. I’m not sure I want holes in my ceiling, but it sounds like fun.”

“So, if we can’t do suspension, what are your favourite restraint positions? I see you have a nice spreader bar — is that your favourite?”

“That’s certainly one of them. I like the helpless feeling of having my legs forced apart and being doubled up. But I also like spreadeagle, either on the bed or standing at the foot of it” — I have a four-poster canopy bed that has a lot of potential for being tied to it — “just as long as my legs are apart. What’s the sense of tying them together and making my pussy hard to get at?”

He picked up a couple of large butt plugs that he’d laid out on the dresser. “I’d guess that you like things up your ass, if I didn’t already know from your profile.”

“Love it. Cocks, plugs, vibes, whatever.”

“OK, let’s get to it. Get your clothes off.” His manner continued to be commanding without going over the line to condescending or cocky. I guess it’s appropriate for a dom to be domineering, I thought.

He watched me as I stripped and hung my clothes over a chair. I did a long, slow strip-tease, undoing my blouse a button at a time and then rocking my shoulders back so it slipped gracefully off my body and dropped to the floor behind me. I slid my pants slowly down to my ankles and stepped out of them, and paused a moment to let him admire me in just bra and panties. I slid my bra straps off my shoulders, then reached behind my back and undid the clasp, holding it in place with my hands before releasing it and letting it fall. I ran my hands seductively over my breasts and belly, noting that my nipples were already rock hard with anticipation. Finally I slid my panties past my hips and let them fall to the floor. I stepped out of them and stood with my legs slightly apart, letting Brandon admire my naked, prominent pussy. I ran a finger up my slit and toyed with my clit for a few seconds. I could see by the bulge in his pants that my strip-tease was having the desired effect on my audience.

Brandon kept his clothes on. I guess he found that being clothed when I wasn’t heightened the sense of power imbalance between dom and sub. That was certainly the effect it was having on me as I stood naked in front of my fully clothed dom-for-the-day.

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.