One in a Thousand Ch. 02

[NOTE: A while back, the number of people following me on Literotica crossed the 1,000 threshold. (As I submit this, it stands at 1,034.) That amazes me and I'm happy that so many people derive some pleasure from my writing. To mark this milestone, I decided to publish a multi-part story that's been percolating in my mind, "One in a Thousand". This is the second chapter. The significance of the title might not be entirely clear yet, but it will become apparent in the next chapter. As always, remember that this is a work of fantasy; it portrays unsafe sexual practices. There's no need for people to point this out in comments. I think we can trust readers to know that fantasies are not blueprints for behavior. --Cyanlot]

Chapter 2: Matt and I Drift Apart and I Cross More Lines

In the months following our visit to Cross the Line, Matt and I drifted apart. It wasn't like we had a falling out. It was just that one of the other of us always seemed to be busy when the other tried to arrange a get together. I wasn't sure what was occupying Matt's time but I was spending time--and money--going back to Cross the Line, always to see Kiera. There were lots of other gurls there who were attractive, even hot. I knew that some of these gurls would be considered hotter than Kiera by lots of guys. But, for me, Kiera was always the choice.

Kiera and I developed a relationship. Over a matter of a few months, with almost weekly visits, I gradually became more than a client to her and she became more than a sex worker for me. She led me to cross a lot of lines that I'd never even seen on the horizon.

In the beginning, we just replayed our first encounter, but with some significant variations. Anyone watching the action would have thought Kiera the customer and me the sex worker. Kiera always called the shots. She directed, I followed. But she was ever faithful to my needs even if sometimes I didn't recognize those needs myself.

Under Kiera's tutelage, I was a living exemplar of the name of the brothel. I was pressed to cross lines I never knew existed and, had I known, I would have never thought I'd be willing to cross. But Kiera was a masterful guide. Each encounter built on our previous ones but also took me further into foreign territory.

Kiera's mastery over me was demonstrated in many ways. She not only called all the shots but the shots she called were designed to emphasize and reinforce her control over me. For example, while there were never any of our sessions when Kiera didn't shoot her load into my mouth or my ass, there were a number of times when she would edge me mercilessly and then deny me for the entire session.

On several occasions, Kiera instructed me to refrain from masturbating between our sessions. (She didn't need to tell me to refrain from sex with others. She knew she was my only "other" at this point.) For reasons I don't fully understand, I mostly complied with this. The one time I didn't, I confessed my transgression to Kiera in our next session. That ensured not only that I would get no relief in that session but it prompted her to put me in a steel chastity cage until our next meeting to ensure my compliance.

"There," Kiera said as she locked my cock in its cage. "That will ensure that you are a good boy this time. And it has a real benefit for you."

I didn't see how that was possible, so Kiera explained: "Now you can masturbate all you want."

"What do you mean? I can't even touch my cock and it will just hurt if I get hard."

"Oh, silly boy! How limited your vision is."

"What do you mean?"

"Here, I'll show you." Kiera pushed me back on the bed and went to the chest of drawers across from the bed. She came back with a very realistic, and very large, dildo. As she walked to the bed, she was stroking it with her hand, as if to excite it to its full size. Looking more closely, I saw that she was lathering it with lube.

Pushing my legs up and apart, she said, "Now let me show you how you can masturbate."

I felt the cold, blunt tip of the fake cock press against my butt hole. While my ass was hardly virginal any more--Kiera had seen to that--this dildo was much larger than anything that had penetrated me before.

Kiera took her time. I'm not sure whether that was motivated by compassion or a desire to draw this out as long as possible. But, whatever the motivation, I was thankful for it. As the dildo pressed more and more insistently into my ass--forcing my sphincter to open--Kiera stared at me with eyes that seemed to penetrate my soul.

I closed my eyes to avoid her gaze but she wouldn't have that. "Open your eyes, bitch! I want you to watch me as I fuck you with this huge cock. And I want to watch the expression in your eyes shift from discomfort to delight."

The discomfort came immediately. My asshole (which Kiera was calling my "pussy") yielded, but not easily. And the dildo was long enough that it sort of rearranged my rectum. But the pain did pass. Soon, Kiera was moving the dildo in and out of my ass and cooing to me about how good it felt to have my "boipussy" filled with a big hard cock. I didn't say anything in response, but she could see in my eyes that I liked what I was feeling.

"See, now," she said. "You can do this as much as you want. Here, you take over." And she guided my hand to the base of the dildo, keeping her hand over mine for several thrusts before leaving it entirely to me.

With Kiera ceding control of the dildo to me, you might think that I could stop thrusting it in and out of my ass. But she would have none of that. When I even slowed the pace, Kiera would command me to "keep fucking my boipussy". I could have defied her, of course, but that's not how my relationship with Kiera was working. She'd taken charge of our sessions.

And, I confess: the dildo thrusting in and out of my ass felt really good. I was embarrassed to be enjoying impaling myself with the fake cock while Kiera dispassionately monitored my actions. But the pleasure swamped the embarrassment.

When Kiera was content that I would continue without her constant supervision, she began engaging with me again as a participant. She ran her fingers over my body, focusing the inside of my thighs and my nipples. Her erotic touch intensified my pleasure and I found myself surprised by how much pleasure I could feel with my cock firmly encased in a chastity device.

Kiera climbed up next to me on the bed and pressed her stiff cock into my mouth. It felt like this was exactly what I needed at the moment. I sucked her shaft eagerly and surprised myself with an audible moan of pleasure.

I realized that, without thinking about it, I had synchronized my thrusting of the dildo in my ass with Kiera's thrusting in my mouth. As her tempo increased, signaling her impending orgasm, I was fucking my ass furiously with the phallus.

Suddenly, Kiera cock exploded, filling my mouth with her salty semen. I gulped her goo down hungrily as I buried the dildo deep in my rectum, pretending (I guess) that it was shooting a load deep in my bowels.

When Kiera had completely spewed her load, she collapsed back on the bed and I stopped fucking myself with the fake cock. We were both spent. Only one of us had had a proper orgasm but, strangely, I felt the kind of relief I'd always thought happened only after an orgasm.

"There," Kiera said after a few minutes of recovery. "Now you're learned something important. Your pleasure from sex doesn't come only from your cock. And, you don't need to ejaculate to have a climax."

I didn't respond so she prodded me: "Am I right?"

"I guess so," I said reluctantly. She was right that I'd learned something. I wasn't sure I really liked what I'd learned.

Our next meeting turned out to be special--not just a line-crossing but one that I didn't control. I mean, Kiera was always my guide across new lines, but this time she didn't lure or command me to cross a line; she pushed me over the line, much to my surprise.

My cock had been trapped in its steel cage for a full week. I'd tried the Kiera-permitted form of masturbation a few times, never with as much pleasure as I'd gotten with her that first time. And the effect of this was that I was horny as hell and I'm sure my prostate was full to the brim.

As we began, I was hoping fervently that Kiera would begin by unlocking the chastity device and allowing me to, finally, shoot my load. My hope, though, wasn't Kiera's plan. Instead, she kept my cock locked and did everything in her power to ensure that my cock was straining against its constraint. She undressed me, ran her fingers over my body--everywhere except where I most wanted to feel her touch, of course.

Kiera backed away from me and began to undress herself. This was doing nothing to lessen my sexual tension. I loved her body. The sight of her perky, perfectly formed breasts, her flat stomach, and her tight, round ass was causing me as much stimulation as her fingers running over my body had.

When she stood naked before me, she began touching herself--running her fingers over her breasts and, ultimately, began slowly caressing her cock. It about drove me wild when she brought her hand, filled with the scent of her crotch, to her nose and inhaled deeply. I felt as if nothing could bring me to a higher level of sexual tension.

I was wrong. Kiera fondled her cock and balls again and, then, walked over to me slowly, extending her finger for me to smell, and then suck. I did this eagerly, hungrily.

"Horny?" she asked playfully, knowing the quite obvious answer. I grunted an affirmative.

"Well ... we should do something about that, shouldn't we?"

I nodded eagerly. And Kiera proceeded, but not at all in the way I'd hoped or expected.

She pushed me onto my back on the bed and spread my legs. She approached me slowly with her rigid rod aimed at my asshole--or boipussy, as she described it these days.

While this wasn't the release and relief I'd hoped for, I was nevertheless eager to feel her cock inside of me. I didn't have to wait; I think Kiera was almost as horny as I was.

As I felt Kiera's hard cock slide easily into my ass, I felt only pleasure. And it was more intense pleasure than I would have thought possible just from anal stimulation. Her cock felt fabulous. She began slowly, and I relished every inch of penetration. I let out a moan of pleasure.

Before long, her pace had picked up. She was holding my thighs and pumping hard into my ass. I could sense her rising excitement and that fed my own.

And then it happened! I was so focused on Kiera's thrusting, squeezing her cock tightly with my ass muscles--trying to will her cock to fill me with her cum--that I wasn't paying much attention to the effect it was having on me.

Suddenly, though, and quite to my surprise, I found myself shooting my own seed--right through the open slit in my cock cage. It was the strangest orgasm I'd ever felt. Instead of a slow climb to a crashing climax, I experienced wave after wave of pleasure coursing through my shuddering body as my caged cock oozed its creamy slime.

I was writhing in pleasure, surprised by the intensity and the novel nature of my orgasm. Even in my ecstasy, I managed to catch a glance of Kiera looking down on me with pleasure. I saw her silently mouth, "good girl!"

I didn't have time to think about that before Kiera began spewing her load in my ass. As she thrust hard, pumping her cum into my "boipussy", Kiera never lost eye contact with me. It felt as if her eyes were penetrating my psyche as deeply as her cock was penetrating my body.

When she'd finished, she pulled out of me very slowly, almost reluctantly. Her softening cock finally slid from my ass and she stood before me, looking down at me and, I think, admiring what she'd accomplished.

I began to feel uncomfortable. Of course, I'd seen plenty of videos of guys and gurls having prostate orgasms, sissygasms, or whatever. And I'd seen guys and gurls spewing their load from anal stimulation while confined to cock cages. But the thought that I would ever do that, or even be able to do that, had never crossed my mind.

I felt embarrassed and emotionally vulnerable. That was the nature of my discomfort. But I'd also just experience a completely novel and very intense kind of orgasm. It was all very confusing.

Kiera took steps to put me at ease. She unlocked my chastity device, which slipped off from my now limp cock especially easily because of the copious quantity of cum I'd shot all over it. And, then, Kiera lay down next to me and very gently, lovingly massaged and fondled my cock and balls.

"How was that?" she asked.

It took me a while to respond and, when I did, all I could manage to say by way of description was, "weird!"

"Yeah," she said, "weird... but good, right?"

I just nodded.

"This was a big step for you, Erica. I wasn't sure you could do it. But I'm really proud of you."

I was so lost in the sensuality of Kiera's hand massaging my soft cock and spent balls that I didn't really hear what she was saying. I just knew that I really loved the many ways Kiera could make me feel.

As our relationship developed, though, I would become very clear about where Kiera's ability to make me feel wonderful things I'd never felt would take me.