Allyson's On-Line Dates

I came back to a huge backlog of potential matches, but I eliminated all but the ones that had come in over the past week. I figured the rest would have lost interest and gone elsewhere by now.

Eventually, one guy seemed to float to the surface: Jonathan. On paper, he seemed very much like Brandon had seemed. Experienced, well versed in consent and safety, concerned as much about my pleasure as his. His profile projected an all-round nice but fun guy, sexually adventuresome but not predatory. When we started exchanging texts, the same impression came across. But then, it had with Brandon too. I took a big risk and asked him for references from previous BDSM partners.

I got back a memoji rolling on the floor and laughing hysterically.

I figured that would signal the end of the trail with Jonathan, and that he would ghost me after that. But rather than start all over, I decided to give him a chance.

"No, seriously.

"The last guy sounded really nice. But when he got too rough and I told him to back off, he just gagged me so I couldn't complain and beat the shit out of me.

There was a long pause. Either he was thinking it over or he really had ghosted me. But then I got another text.

"The fucking bastard. I get why you're gun-shy.

"I'll need to contact some previous partners and get their permission. Hang on for a few days."

Hmmm. It sounded as though he had respect for people's privacy. That boded well. "OK, I'll wait."

I don't know why Jonathan turned me on so much. Looking back on it, Brandon had seemed kind of over-slick, although I hadn't noticed it at the time. He seemed to have every right answer, but now as I looked back on them, his answers seemed kind of rehearsed. Jonathan's didn't, somehow. I couldn't explain it, but I found my pussy getting wet just thinking about him. I had to recharge my favourite vibrator a couple of times as the days passed and the suspense built up.

Then out of the blue came a text from Jonathan with a name and a number. Then another, and a third. I texted all three of them, and got back pretty detailed replies. They all praised Jonathan's abilities with bondage and pain devices, but they also praised his respect for boundaries and the care with which he treated subs. Two of them also praised his cock, but not for its size. For what he did with it.

I guess they could all have been Jonathan's buddies posing as female subs. But when I asked where they'd met Jonathan, they gave me the contact information for dating sites. I went on the sites, matched the names, read their profiles, and then texted them directly through the site. They all checked out as women interested in men for bondage and pain play.

Well, there wasn't much more I could do unless I learned to read minds. We set up a date.

This time I decided to start with the more classic date repertoire so I would have more time to size him up in person: a table for two at a nice restaurant. We got a table in an out-of-the-way corner to make it easier to talk about things that we didn't necessarily want to subject other patrons to, and we sat three-quarters from each other rather than across so we could talk more quietly. I tried to engage him in chatty conversation rather than going on with the interview style I had established in our texts. But we still talked quite a bit about BDSM, since so far it was the one thing we knew we had in common.

"Ever have a long-term bondage partner?"

"Not for a while. They've mostly been one-night stands lately, with a few repeats. I guess I've never hit it off with anybody enough to form a real relationship, although I've had lots of good times. There was one a while back, though: Angelica. I met her at a party -- not even a BDSM party, just a get-together. She ended up chained to a wall in my basement. We didn't move in together, but we started seeing each other most weekends." He got a somewhat wistful expression on his face as he recounted his relationship with his ex-playmate.

"She could sure take a lot of pain, that one. She didn't even mind if I broke skin, although I was always careful to stay on the right side of leaving scars. I don't actually like hitting anyone that hard, but I did it because she liked it. It was hard for her to cum if she wasn't warmed up with at least a good spanking."

"What happened to her? Did you have a falling-out over something?"

"She just disappeared from my life one day, and I haven't heard from her since."

"My God, that's awful, not even knowing where someone is."

"Oh, I have a pretty good idea where she is, but you probably wouldn't believe me if I told you. Anyway, I really don't like to talk about it."

I could see it was a sore spot, so I turned the conversation away from his disappeared ex. I regaled him with some stories about my adventures with Kendra and Kev on the island. Then I turned to more personal subjects. I elaborated on some of the boundaries I had already discussed in my profile and our subsequent texts, including my pain tolerance (definitely more than mild, but not extreme, and definitely not Angelica-style). I told him that I loved being gagged, but that I'd rather not do it during our first scene. "I really want to be able to tell you what's working well for me and when I want you to knock it off," I explained.

"That suits me, too. Safe kink depends on clear lines of communication."

Once we were both clear on what they were, we wandered off the subject of boundaries. I asked, "What got you into bondage sex?"

"I don't know. I wasn't particularly aware of any sadistic urges or even bondage fantasies. I never really liked porn videos that featured floggers and such. But some time in my early twenties, I guess, a date presented me with a crop and a pair of handcuffs and asked me to use them on her. It seemed really weird at first, and I almost said no, but when I started in, it seemed way more natural than I'd expected it to. When we got around to actually fucking, I came harder than I ever had in my life. I've never really looked back."

"For me, it came later. I'd never really noticed those urges. But a date spanked me one time, and to my surprise, I really liked it. The next time, he tied me up and spanked me, and I liked it even more. It just grew from there."

After we'd taken care of dessert and the cheque, we decided to go back to his place. It was somewhat against my better judgement, but I'd vetted him so thoroughly that I thought I could trust him. I doubted that very many men would have put up with all that fencing about, not when there seemed to be a lot of other fish in the sea. Anyway, he got my attention when he said, "I have some really neat new devices I'd like to show you." Just as if he was inviting me over to look at his stamp collection. Since Kendra and Kev introduced me to the vast range of possibilities, I've been a sucker for neat devices.

Jonathan had a cute little two-story house with a small garden in front of it. I walked in the front door, kicked off my shoes with relief -- I don't care much for heels, frankly -- and Jonathan showed me around. The entire house was much tidier than a lot of bachelor pads I've seen. No beer bottles on the counter, no wet towels on the hall floor. I was getting to like this man already.

Jonathan opened the door to the basement and we went downstairs. Through another door was one of the best-equipped dungeons I've seen, with the possible exception of the one we rented for a night on the island. Four-poster bed, St. Andrew's cross, pullies hanging from the ceiling, what appeared to be an old-fashioned whipping post. Jonathan pointed to one piece of furniture. "That's brand new. I just got it out of the box and assembled it yesterday. Want to help me break it in?"

The new toy was obviously a bondage bench. The basic bench part was short, no longer than the average human torso. Four long padded rests extended from it, two at the top and two at the bottom, just about the right length for an entire forearm or lower leg. It even had a face rest with a hole in it like a massage table. The rests had two straps each, and so did the body of the bench. There was even one dangling from the face rest. I could see that once you were snugly strapped into that thing, you would be totally immobile but also completely exposed.

"The rests are almost infinitely adjustable. It's set up for face down right now, but you can move them all around for face up, legs wide apart or close together, arms over your head, straight out or down by your sides. It's limited only by your imagination. And look at the quality."

I unfastened a thumbscrew on one of the rests and moved it. It moved easily without any wobble, suggesting robust bearings. I tightened it back up, and put all my strength into trying to move it. It didn't budge. "That set me back quite a chunk of change, but I think it's going to be worth it."

"Oooh. I'm getting wet just looking at it. I'd love to try it out." I took off my clothes and hung them on a conveniently placed coatrack in the corner. There were even wooden hangers to keep my blouse and skirt from getting wrinkled, and smaller hooks for bra and panties. Jonathan was obviously a very thoughtful dungeon-master.

Jonathan took his clothes off as well, and hung them up neatly. I was pleased to see a well-muscled chest and arms, not body-builder muscled but obviously the body of a man who was no stranger to a gym. His ass was compact, and his cock, already partly at the ready, looked satisfactorily pussy-filling but not painfully huge. For my personal taste in male bodies, he couldn't have been better.

I climbed onto the bondage bench and settled my arms and legs on the rests. Jonathan adjusted them a bit so they fit my body size perfectly, with the leg rests a foot or so below the level of the bench so I was bent over on all fours. He fastened the straps around my arms, legs and body, pulling them good and snug but not cutting into my flesh. He didn't fasten the strap that would have gone behind my head, so I could still lift my head and look around if I wanted to, but I tried putting my face on the rest experimentally and it was certainly comfortable. I felt like I was about to get a massage. He adjusted the leg rests one more time so that my legs were held, not radically far apart but just far enough to allow easy access to all my fuckable bits. I was in love with this bench already.

Jonathan went to a shelf and picked up a flogger with a solid handle and what looked like about six tails in braided leather, very similar to the one in my own toy drawer. He held it in front of my face for approval, and I nodded. The more tails, the less force each one would exert. Six was about right, I thought. Enough to make sure they didn't cut into my skin but not so many that it would feel more like a tickler than a flogger. And I liked the look of the braided leather. This was a genuine pain toy, not a wimpy bunny flogger.

He brought it down on my ass with a deliberately glancing blow so it stung like a swarm of bees without a lot of direct impact. Ah, this guy was as expert with the toys as he said he was. I gave an involuntary gasp and a slight yelp, but my pussy started to juice even more at the sensation. "You can go a bit harder." He ramped it up a bit, then a bit more, until I finally said, "That's it. Just like... OW... that."

Once he'd gotten me good and warmed up with fifteen minutes or so of flogging, he put down the flogger and came around in front of me. "Don't worry, I'm not finished the pain play yet. I just wanted a little variety." He undid a thumbscrew and the face rest swung down out of the way so he could offer his cock to my waiting mouth. I took it eagerly and gave him a thorough licking around the head and up and down his slit. He gradually fed more and more into my mouth until it was right at the entrance to my throat. He looked at me a bit quizzically, and when I didn't gag or pull away, he pressed firmly and it slid an inch or two down my throat. He pulled back, let me take a quick breath, and pushed it a little further down. He was obviously experimenting to see how much I could take. Eventually he had it all the way down so I could kiss his balls at the end of his stroke. I loved the feel of it rhythmically sliding in and out of my throat, and I could hear his breathing deepening as his pleasure built.

He kept that up for a few minutes, but finally pulled away, panting gently. "That's just an hors d'oeuvre," he said. "I don't want to use up my load too early." He put the face rest back in position, then went around to the other end of me and put his head between my spread legs, taking my pussy lips between his lips and stretching them, then sucking my clit into his mouth, stretching it gently and oh, so excitingly. He seemed to know exactly how much suction to use, making me squeal in pleasure without overstimulating me and making me want to slap his head away.

Two fingers went into my vagina. First he curled them slightly forward, massaging my G-spot. Then he turned his hand around so the curve of his fingers was facing my rectum. He massaged for a minute or two, then pulled his fingers out for a few seconds. When they went back in, I felt his thumb exploring the entrance to my asshole. It felt slick, and I knew he had used those few seconds for a quick shot of lube. I could feel that his nails were closely trimmed and smooth. This guy knew exactly what he was doing with every part of a woman's body.

Once he had his thumb well seated in my ass, he curled his fingers toward it so he was firmly pinching my taint between the thumb in my asshole and the fingers in my pussy. No-one had ever done that to me before, and Jesus merciful Christ, did it ever feel good. It felt even better when he brought his other hand around and began spanking me firmly on the ass-cheeks at the same time as he was massaging my taint. Little rockets of pleasure were surging up through my body from all the combined sensations. I struggled involuntarily against the straps holding me against the bench, and the resistance that told me I was totally helpless only magnified my arousal. My entire body clenched and I screamed with what would be the first of several mind-blowing orgasms.

He pulled out his fingers and thumb. In a few seconds, I smelled hand sanitizer. Good, I thought. I didn't know where that thumb was going next, but he obviously knew that rectal microbes don't belong anywhere else. Then I heard a prolonged gloop of a lube pump. The fingers went back in my pussy, this time accompanied by the thumb, pressed together in a conical shape like a bird's beak. He rotated his hand back and forth gently and gradually forced more of his fist into me.

I'd been fisted before, and liked it, but it had always been by a woman. I wondered what a man's larger hand would be like. A recent news report popped into my mind. A couple had been having consensual sex, and the man suddenly shoved his whole hand into her. She screamed, "No! That hurts! Take it out!" He didn't, and she had to put her feet on his chest to push him off. The judge agreed that the sex became non-consensual the minute she told him to stop and he didn't stop. The guy went to jail for sexual assault. I didn't expect Jonathan to do anything of the sort, but it made me stop and think. There was certainly no way I could get my feet on his chest if I wanted him to stop and he didn't.

At first his fist felt good. Even though it hurt, it was a good kind of hurt, sending more rockets of pleasure through my body. But as he got up to his knuckles, the pain crossed the line, telling me that the fist was on the edge of doing damage. "That's enough," I gasped. "My pussy just hit its red line." He instantly stopped pushing.

"Out?"

I thought for a minute. Until it hit that red line, his fist had been feeling genuinely good, balling pleasure and pain together in ways I'd never experienced quite that way before. What if he just left it right there? But once my pussy's alarm button had been pushed, the klaxon just kept on sounding, and I didn't think I could get back to that magic mixture.

"Yes," I finally conceded. The fist slowly withdrew, leaving me with a totally different bundle of pleasurable sensations as it slid out and my pussy gradually returned to its usual shape and size.

He cradled my pussy in a soothing gesture. He didn't apologize for hurting me -- that was the deal. He had licence to hurt me until I said "Enough," and then he was to back off, which he did. Instead of apologizing, he made amends by smacking me a few times good and hard with a riding crop.

He put the crop down and I heard another gloop of lube being pumped out. A finger worked some into and around my asshole, and I felt a cock-head press against it, gently at first, then more firmly. "Wait a minute," I said. The cock withdrew. "Before we go any further, I want you to gag me."

He walked around in front so I could see him and said, "You sure? You told me you didn't want to on the first date."

"Yes, I said that. But now I know I can trust you. I just love the feeling of being tied up with something shoved in my mouth, so it's worth it to me to take this farther" I waved a finger in a circular motion. "That means, 'Harder. Faster. More.'" I held my hand flat, palm down, fingers together. "That means, 'Just right. No harder.'" I flipped my hand sideways, still palm down. "That means, 'Too much. Back off.'" Finally I flipped my hand sideways again, this time with the fingers splayed wide in an urgent-looking gesture. "That means, 'Red. Scene over. Get me out.'"

"That all works for me." He went to his toy shelf, his erect cock wiggling erotically, contemplated a minute -- it seemed as though he had lots to choose from -- and came back with one. It was a simple but effective-looking leather stuff gag with a flattish stuffer built into a panel gag so wide it had a cut-out under the nose to make sure the wearer could breathe. "How about this? My subs often tell me that the flat stuffer makes it comfortable enough to wear for a whole scene."

I didn't say anything. I just tipped my head back and opened my mouth wide. He settled the stuffer behind my teeth and buckled the gag snugly behind my head. I experimentally tried to say something, and nothing came out but a faint "Mmmpphh" through my nose. Perfect. My pussy gushed with pleasure at the final touch to my restraints. And he was right -- no gag is exactly comfortable, but I've been gagged with things that felt like they were going to break my jaw. This was none of that. The connection between the stuffer and the panel was narrow enough that I could almost close my teeth, but the stuffer held my tongue down firmly and the panel took care of any sound that escaped around it.

Jonathan walked back to the other end of me and picked up where he left off. He renewed the lube and pressed against my sphincter again, and with just a momentary hint of pain as it pried me open, his cock started to slide in. He took it nice and slow, stopping for a minute if he heard me gasp through my nose before pressing in some more. It didn't take long until he had his entire cock inside me. He left it there, not moving it, while my rectum adjusted to having this foreign object intruding into it. Then he started making long, slow, gentle thrusts.

To tell you the honest truth, if I had to pick one form of sex to use for the rest of my life, I'd pick vaginal. An anus has lots of nerve ends, but a vagina has a lot more, and it's in better proximity to the clitoris and the G-spot. It's designed by nature to give a woman pleasure, presumably to encourage her to be fruitful and replenish the earth. But fortunately I don't have to pick one over another. Having a toy, or even better, a cock up my ass feels so naughty, so slutty, that it more than makes up for the slightly indifferent physical sensation. And a creative dom can usually find ways to stimulate both parts of me at the same time, which is the absolute pinnacle of bliss.