One in a Thousand Ch. 06

[NOTE: A while back, the number of people following me on Literotica crossed the 1,000 threshold. (As I submit this chapter, it stands at 1073.) 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 sixth chapter. I'm submitting it at the same time as the previous two chapters so readers can continue the story into what some would consider the "good parts" right away if they want to. 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]

One in a Thousand

Chapter 6: My Weekend with Kiera—My First Date

Promptly at 2:00 pm, there was a knock on the door of the suite.

"That will be Greg," Kiera said. "You should answer the door and invite him in. Valerie has to go but the three of us can talk for a bit and then you need to invite Greg back to the bedroom so you two can get to know each other better."

Shit! Was I really going to do this? I thought.

Kiera noted my hesitation and prompted me with, "You said you trusted me and would do what I told you to do. Isn't that right?"

It was. And so I walked to the door with Valerie, who was leaving, and invited Greg in. Greg was decent looking, probably in his mid-thirties, with short brown hair, about 5'10" tall with a fairly slight build.

I motioned Greg to come into the living room, having decided to use my voice as little as possible. He sat down and Kiera started making small talk with him. I was sitting in the chair opposite Greg and feeling quite a bit of turmoil about what was in store for me.

He's a good enough looking guy, I thought and immediately silently chastised myself. I knew what I was going to be doing with Greg—roughly, anyway. I'd accepted that I was going to follow whatever Kiera had planned. But that didn't mean I should start sizing up the guy I was going to be having sex with this afternoon.

To be fair, though, Greg seemed to be sizing me up. He kept up his conversation with Kiera but his eyes kept wandering over to me. At one point, when our eyes met, he smiled, sort of nervously. Without thinking, I smiled back. He was obviously uncomfortable and I felt as if our mutual unease was a bond between us.

Kiera asked Greg what he wanted to drink and sent me to the kitchen to get him the beer he wanted. Kiera had me poor glasses of wine for the two of us. My practice walking in my heels this morning had been enough to make me reasonably proficient and I tried to move the way Kiera and Valerie had taught me to. Apparently I was doing okay. I could see the reflection of Greg and Kiera in the sliding glass doors and Greg's eyes followed me with interest.

Greg's apparent awkwardness made me suspect that this afternoon's plans were crossing a new line for him. Strangely, I guess, I found myself hoping that the obvious interest Greg had in my appearance was based on finding me attractive and not on finding me freakish. I'm not sure why I cared, but I did.

The conversation in the living room went on for perhaps 15 minutes, with barely a comment from me. At which point Kiera decided it was time to get things started.

"Erica," she said, "why don't you show Greg the bedroom? I think he'll find it ... inviting."

As Greg and I walked to the bedroom, I found that my heart was pounding in my chest, a motion that was exaggerated by the weight of my breast forms. My ears were hot and I was sure I was blushing.

How am I supposed to do this? I wondered. And then it hit me. I thought back to the way Kiera had handled my first visit. If this was Greg's first time with a crossdresser, and at this point I was pretty sure it was, I should play it the way she had. She had put me at ease and made the experience one to warmly remember.

"So, Greg," I said, trying to make my voice sound somewhat feminine but not cartoonish, "how do you want to play this?"

He seemed as confused as I had when Kiera had asked me that question so many months ago. "I don't know what you mean," he finally said.

"I mean, do you want this to be like a date or do you just want to get down to business right away." I didn't remember Kiera's exact words, but I thought this was close.

"Oh, I don't know ..." and he trailed off.

Greg's obvious awkwardness came off as shyness and was, to tell the truth, kind of endearing. In any case, it emboldened me to take the initiative. And I found that surprisingly comforting. This wasn't something that was going to be done to me; it was something I was going to do. I was now in the role that Kiera had been in our first meeting.

"Why don't you just sit on the bed for a minute and watch?" He seemed happy to do whatever meant that he didn't have to take the lead. When he sat down, I began slowly unbuttoning my blouse.

It turns out you don't need to be a woman, or even an experience gurl (if I was a gurl now, I sure wasn't an experienced gurl), to know how to undress suggestively for a man. We see it all the time in movies and Kiera was a master (mistress!) of this skill.

As I unbuttoned my blouse and let it fall open in the front, my eyes were riveted on Greg's which, in turn, were riveted on my chest. For the first time I felt the feminine power over the male libido. I looked down to his crotch. I couldn't really see a bulge there yet, but I was pretty certain he was feeling his cock rise.

I realized that my feelings about this afternoon's activities had gone from trepidation, to acceptance, to (finally) enthusiasm. This was going to be fun, I realized. I was Kiera and Greg was me, on that first time together.

I unzipped my skirt and slid it off my hips, watching Greg's eyes follow the action. I was sure he could see my chastity device through my lace panties, especially because it was now protruding more than it had been. But I hoped his attention was focused on those panties, my garter belt, and my stockings. They were, after all, chosen precisely to get that reaction from a man.

Stepping out of my skirt, I shrugged my blouse off and let it fall to the ground. As I took a step toward Greg, I said, "Let's get you a bit more comfortable." And I knelt down by the bed, between his knees.

There was no question now about the bulge in Greg's pants. It was painfully obvious to me and, I'm betting, a bit painful to him. I put my hands on the insides of his thighs and ran them up slowly toward his crotch. I felt him through his pants and was a little surprised at how exciting the feeling was. There was a sense of power in being able by my image and touch to provoke such a response in a man.

While he was still sitting, I could unbuckle his belt, unsnap and unzip his pants. But I had to get him to stand up in order to pull down his pants and boxers enough to free his cock. I pushed them down to his ankles and he stepped out of them, forcing his shoes off in the same motion. Greg started to sit back down on the bed but I stopped him.

I was on my knees and his hard cock was just inches from my face. As I watched it, fascinated by the way it bounced with anticipation, I realized that I could do this. I mean ... I knew I would do it. It's what Kiera had planned and I had committed myself to following her plan. What I realized is that I didn't need to force myself to do it.

I'd sucked Kiera's cock many times. And I'd found that I loved doing that. It was partly the sense of power I felt when I sucked on her hard cock and tamed it by making it spew its load in my mouth. It was partly the fact that I liked being able to make Kiera feel so much pleasure. But, over time at least, it was also about the fact that I'd just come to love the sensation of her hard cock in my mouth and, then, the taste and texture of her cum when she finally shot her load down my throat.

Greg's cock was beckoning to me and I wasn't going to ignore it. I'd always loved it when a girl would suck me off on her knees when I was standing up. And it was even better when it was Kiera, beautiful and talented as she was, doing that. It gave me a feeling of power, like the person doing this was submitting in some way. I'd come to learn that the one on their knees sucking the cock had power, too.

Since I liked it when a girl was down on her knees sucking my cock, I figured Greg might like me doing that, too. I put my hands on the back of his thighs and pulled him toward me. His cock was hard and pointing straight out; I didn't have to use my hands to guide it into my mouth.

Despite my experience with Kiera, I still qualified as a neophyte in the cocksucking business. Still, I was sensitive to the differences between Kiera's and Greg's cocks. Greg's was larger than Kiera's and more heavily veined. It felt heavier in my mouth. I found myself savoring the uniqueness of the experience.

I could have kept doing this for some time. My jaw hurt and sometimes Greg's thrusting made me gag a bit. But the feeling of his hard cock pistoning in and out of my mouth was incredible. I couldn't quite take him completely in my mouth. But I was engrossed in the challenge of trying to do so.

While I would have enjoyed this going on for some time, I could tell that Greg wasn't going to last long. His hips were thrusting at an ever-increasing pace and I felt his hands on the back of my head as he tried to bury his cock completely in my mouth.

And then, with great intensity, he was shooting his load deep in my mouth. He roared as his cock spewed jet after jet of cum. I struggled to keep up swallowing his seed. Finally, I felt his whole body shudder with the ferocity of his orgasm.

"WOW!" he said, breathlessly as he released my head from his grip and pulled his softening cock out of my mouth. "Wow! That was incredible!" Greg fell back on the bed and I got up and lay down next to him.

"I'm glad you liked it."

"I loved it," Greg went on. "The only problem is ... " And then he stalled.

"What's the problem?" I said in an upbeat tone.

"Well, the only problem is that I really didn't want to shoot my wad so quickly. I was looking forward to a little more action."

"You could have stopped me," I replied.

"Yeah ... Well, no I don't think I could have." Greg paused for a minute. "That felt so terrific I'm not sure I could have stopped you."

"Well, in any case, we have lots of time. There's no need for the fun to be over. What else did you want to do?"

With that, Greg reached over and put his hand on the front of my panties, feeling my caged cock.

"Do you have to have this on?" he asked.

"No. Kiera thought it was a good idea but I can get the key from her. Is that what you want?"

Greg hesitated and I realized that I'd made him uncomfortable by asking him to verbalize this. I rescued him. "I'd like to take it off. I'll get the key."

Kiera wasn't surprised by my request.

"I thought that is how this would go. Most of the guys who want to hook up with a gurl—whether it's with a crossdresser or a transexual—think, or at least say, that they just want to fuck them. But, they can fuck a CIS woman—they can fuck her in the ass if that's what they want. But what they really want is a shecock. I'm not surprised that Greg wants yours. You're very desirable."

"Have fun," she said, tossing me the key. Walking back to the room, I realized that I was flattered by Kiera's saying I was very desirable.

I decided not to take the cock cage off myself but to let Greg do it—kind of like allowing him to unwrap his present. I thought that might be more exciting for him, but I knew it would be more exciting for me.

Greg was sitting on the side of the bed and I was standing in front of him as I handed him the key. I brought his hands to the sides of my lace panties and, taking my motion for the signal it was, he slid my panties down and off completely.

Greg's hands trembled a little as he brought the key to the tiny lock on my chastity device. He removed the sheath encasing my cock, which was already slightly engorged, and left the ring around my cock and balls. For a moment, he just looked at my cock, which was filling more in anticipation of what might be to come (cum?!). It occurred to me that this was likely the first time he'd ever had the opportunity to examine another person's cock closely.

And examine it he did. I don't know whether this was motivated by fascination or trepidation about what might happen next but, for what seemed to me like several minutes, Greg just took in the sight of my hardening shaft. It probably wasn't that long, I was eager and not at all ambivalent, so my sense of time might have been skewed. But it was longer than I wanted. I reached down and grabbed both his hands and brought them to my cock, cupping it in his hands.

I could tell, not only by Greg's hesitation but by the look on his face, that he was conflicted. But I could also tell how that conflict was going to be resolved. Greg continued to cup by cock and balls in his hands, massaging gently as my cock rose to full staff. Then, as if he'd crossed a line in his own mind, he cupped my balls with one hand and began stroking my cock with his other.

Within just a minute, he leaned forward and took my cock into his mouth in one, swift motion—no licking or teasing, just rapid engulfing in what he now admitted to himself was his eager mouth.

While I think he'd never even looked closely at another person's cock, much less sucked on it, it turns out that enthusiasm can compensate for a lack of experience. Once Greg had crossed that line he'd previously drawn for himself, he went at my cock with wild abandon. It seemed to me as if he was suddenly slaking a thirst he'd had for a long time but never acknowledged.

Whatever was driving him, it was certainly good for me. Greg wanted my cock; he wanted my cum. And I was happy to satisfy those wants.

As I felt my orgasm coming on, I asked, "Do you want me to cum in your mouth?" I already knew the answer. If he'd said he didn't, he would have been lying, not only to me but to himself. I'd asked, not to learn the truth, but to make Greg admit it. That's why I didn't settle for a nod and a mumbled affirmation.

"No," I said, pulling my cock from Greg's mouth and tipping his head up to look at me. "You have to tell me. Do you want me to cum in your mouth?"

With some difficulty, Greg finally said, "Yes ... cum in my mouth." And, with that, his mouth was back on my cock and urging me to comply with his request. Something I was going to do very quickly at this rate.

After being aroused most of the morning as Kiera and Valerie feminized me and, then, being locked in the chastity device for so long, I was primed and ready for release—like a cocked gun with a hair trigger. Soon my cock was erupting into Greg's hungry mouth.

Greg gagged. Here the enthusiasm didn't compensate for experience. But he was intent on completing the task he'd set for himself and, to his credit, managed to swallow all the seed I'd deposited in his mouth.

I backed away from Greg and sat next to him. "How was that?" I asked.

"It was ... " Greg struggled for words. "It was okay, I guess."

"Hey, Greg," I reassured, "it's okay to say you liked it. Really, it's okay."

"I guess I,i>did like it," he finally admitted.

"Well, I already knew that," I said as I patted his somewhat swollen cock. "This guy gave you away. I just wanted to hear you say it."

The two of us flopped back on the bed, side by side, Greg naked and me still in all of my feminine lingerie, except for the panties of course. I kept my hand on Greg's cock, gently massaging it. As I did, I felt it continue to swell.

"Wow, it looks like you're getting up for some more action," I said. "And so soon!"

Greg didn't reply so I prompted him. "Do you want to cum in my mouth again? Or do you want to try something different?"

"Like?" he asked. I'm sure he knew what I was suggesting but I guess now he was the one what wanted it verbalized.

"You can fuck me if you want." I surprised myself saying this, even thinking it. But there you have it. For the first time in my life, I was inviting a guy to fuck me in the ass. Anal sex wasn't new to me. Kiera had seen to that. And I'd learned that I enjoyed it when she fucked me. But this seemed different. This wasn't Kiera; it wasn't a gurl at all. It was a CIS guy and I'd just invited him to take my ass.

Greg responded positively to my invitation. The first response was a nonverbal one from his cock, which hardened completely at the thought. Then Greg said, "Can I?"

"Oh, Greg," I replied. "We might not be at the brothel but this is still all about crossing lines, isn't it. For both of us it seems."

Greg wanted to take me from behind, with me on my hands and knees on the side of the bed. Maybe missionary would have been too intimate for him. Or maybe he would have been uncomfortable with the constant visual reminder of my maleness, if not masculinity, though he didn't seem to mind looking at my cock earlier. But it didn't matter to me. I got on my hands and knees and presented myself for him to take.

He slathered on some lubricant and I felt him guide his cock to my ass. Maybe I should have been thinking of it as my boipussy or something like that but I wasn't quite there in my mind.

Greg was larger than Kiera, but not enormous. My ass accommodated his hard cock without complaint and, as he began stroking in and out of my ass, I felt the now familiar tingling of the nerves in my sphincter. I moved to his rhythm with pleasure and found myself enjoying the mental image of him shooting millions of tiny swimmers into my bowels.

As he approached his orgasm, Greg grabbed my hips forcefully and thrust deeply into me. I could tell by his motions and his grunting that he was shooting jet after jet of cum into me. I knew what he was feeling and it felt good to me to be the cause of those feelings.

Then he collapsed on top of me and I flopped down flat onto the mattress. I felt Greg's cock soften in my ass and, finally, pull out completely. And then he rolled off of me, still breathing heavily.

"It felt like you liked that," I said understating things by a country mile.

"Oh, God!" Greg panted. "That was terrific!"

We rested for a while and then I told Greg it was time for him to get going. He pulled on his clothes and, stopping at the door of the room for a moment, looked back at me awkwardly. He clearly didn't know how to end our session.

"It's fine," I reassured him. "It was great. Take off."

After Greg had gone, I cleaned up a little and then went to the living room area to talk with Kiera. It was like a debriefing session. She wanted all of the details, and I provided them. She didn't give me details but she made clear that Greg was extremely happy with our session. Kiera was clearly pleased with how the afternoon had gone.

"I hope your evening date is just as exciting," she said, reminding me that Greg was only the first of two dates I had today.

"I don't know. I'm pretty tired," I said.

Kiera was having none of that talk. "Nonsense! A nice long shower—which you need anyway, by the way—and a fresh change of clothes will re-energize you." She paused. "And, trust me, tonight is something completely different.