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."
