Allyson's On-Line Dates

"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.