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.