The Chance Fantastic Pt. 05

Author's Note: This is the last part of this story I have written. I have ideas for subsequent chapters I could write, but I also feel comfortable leaving these characters here. if you want me to continue this story, please let me know via comments or messages. if you'd rather have me write something new, I'd also appreciate hearing that via comments or messages. Enjoy!

The Chance Fantastic Pt. 5 - Bearing Fruit

Brad Paisley, as it turns out, fancied himself as something of a comedian. I actually found the concert quite enjoyable, despite not knowing any of the songs and not being the world's biggest country fan. He used the video screen behind to great effect, and was a lively and entertaining performer, plus an admirable guitarist. If I wasn't so distracted the whole time, I might have been a true convert.

It was the first time I hung out with Greg since I sent him the first email. Or the second email. Or the third this morning. Each one had a flirty message and a video attached. For the second email, I sent him a video of a trans girl getting gangbanged. It was actually the same actress as the first video, wearing a lacy purple lingerie set. She got DP'd anally, and facefucked. It was incredibly enjoyable for me. The email itself focused on describing her a little more than the first email did:

"Hey Greg, I hope you're having a great holiday. If you have time, I'd love to watch this video with you. Just look at how soft and pert her butt looks in the lingerie. Could you imagine yourself sliding your meat up and down her, hearing her moan with pleasure? Girls like this just live for cock Greg - I know, I'm one of them ;) Don't you love it when a girl really goes to town on a nice hard cock? Look at her take it all. Her lashes look so much better when her mascara is running because she's choking on cock. Could you imagine her delicate hands lightly touching your shaft, as she parts her big, cock-sucking lips and puts you inside her warm mouth?

Just know that if you're brave enough, you might find a gurl near you who wants to worship your cock like that. Love,

Your local cock-loving slut."

The third video I sent, the one that morning, was my most daring yet. It was a hypno video, but not geared towards sissies. Rather, it was directed towards an audience of alphas, and it endeavored to teach them how to enslave their very own sissy slut. It came with its own set of rules. It started out with a wall of text, explaining that sissies really exist, and that you could really have one, but you needed to help them out of their cages.

As images of sissies started to flash on the screen, it would explain that most sissies develop their fetishes in isolation. Porn leads to crossdressing, which creates an addiction with a strong urge. However, in their normal lives, sissies still identify as straight and view their addiction as just a habit. The video then started to positively encourage the alpha that manipulating the sissy into sex would actually help the sissy, help them cross that line and be able to embrace who they really are.

The key, the video explained, was securing a real meeting with that sissy. If they met up in real life, they wouldn't be able to back out. The rest of the video focused on how to enslave, blackmail, and ensure the sissy would be your individual slave for the rest of your life, which I wasn't so concerned with. I just needed Greg to get the message that a meetup was the key.

My email was in that vein, "Have you ever wondered how to make reality fantasy? How to take that step from masturbating in your room to having your big, hard cock sucked on by a real gurl? Wouldn't that be something? Well, I think this video sums it up pretty nicely. I wonder how many sissies you have around you? How many of your coworkers and friends go home, get dressed up all slutty, and dream of having their tight assholes full of your cock and your cum? And did you ever think that maybe if you were a bit bolder, you might at least find me, a gurl desperate to get her hands on your cock? I can't wait to meet you Greg, and I can't wait to make you feel like the king you are. I've been practicing on my dildo. Believe me, you won't want to miss this tongue ;)

Love,

Your local cock-hungry whore"

Greg hadn't responded to any of these emails. I wasn't even sure he had seen them. But I was nervous as hell when I went down to his apartment Saturday night. I was even more nervous because I was wearing a set of purple panties suspiciously similar to the set worn by the actress in the gangbang video I had sent him. It was a bikini cut with a lace waistband. Both the bum and the panel covering my dick were see-through, though my cock was framed by more lace. There was a small semi-circle cut out at the top of my ass to put my crack more on display.

I didn't have much of a plan for how to get Greg into bed for real. I wasn't even sure if that was what I really wanted. All I knew is that I never felt hotter than when I was composing my emails to him, and thinking about kneeling on the floor in front of him. The whole panties gambit this night was a vague notion that if I ever bent over, he might see them and start to get some ideas. But at the same time, I couldn't bring myself to believe that a gambit ripped straight from porn would work. Plus, I didn't want to come on too strong. Him realizing I was his mysterious emailer in that manner might come across as creepy, rather than sexy. If he somehow made the next move, that would put me in a position to be a little bit bolder with my seduction.

But, despite my nerves, the whole night proceeded rather normally. I was fidgety and weird, I think, when I first went down to his apartment so that we could carpool to the concert. But he seemed just like normal. There were times when I was utterly convinced that he hadn't even seen the emails. But then a "but what if he did," thought would cross my mind, and I would get excited and anxious all over again.

Greg paid me no mind. He was having too much fun. In addition to this being one of his favorite artists, we happened to be sitting next to a cute girl who seemed pretty keen on flirting with us. This type of thing never happened when it was just me, but I wasn't surprised that it happened when I was with Greg. Even with my nerves, I still ended up having a blast. The last song of the night was a tribute to Brad's wife. A fun fact about both Brad Paisley and Greg: Brad was married to the titular Bride in the Father of the Bride movie (with Steve Martin), and she was one of Greg's first crushes. So of course Greg couldn't help leaning over to me and telling me how beautiful she was during the song.

That was Greg's way. Greg didn't talk about girls in terms of "hotness." To Greg, girls were beautiful. Even though Greg was a bit of a serial dater, and he would make out with almost any girl at the drop of a hat, he still respected them, and thought of them as people he had to be worthy of. As I thought of this, a small part of me had a twinge of regret. I wasn't interested in that romantic aspect of Greg. If I could, I'd kill that aspect of him. I wanted the dirty and wild part of him, the part that jumped on our hookup website and regularly watched porn.

It was easy enough to console myself, though. I likely wouldn't succeed at either enlivening the hedonistic part of Greg's mind or killing the beautiful romantic. I probably would never get to cross that bridge with Greg. And I think I was okay with that. It was just fun to pursue it for a while.

We spent the first part of the car ride home just talking about the concert. Greg wanted to know what I thought, this being my first Brad Paisley concert.

"Yeah, I had a ton of fun. It was definitely more of a show than a concert, which is better for people who are not strictly fans or familiar with his music."

"I know! Plus, he's hilarious."

"Yeah, it's cool when an artist interacts with the crowd that way. To me, that's the main appeal of a concert. Almost all artists sound better in a recording, but if they use their concert platform to interact with the audience, or to augment or change up their music, it's a more enriching experience."

"Dude, you're such a nerd, 'enriching experience.'"

"You know that's why you love me. Besides, you already knew that I'm a nerd. We have hard evidence of that. That girl ignored me all night, but couldn't take her eyes off of you."

"That's just because you were a seat away. I'm sure if you had been next to her, you would have gotten her number."

"You got her number?"

Greg looked sheepish. "Actually, I didn't. I could tell she wanted me to ask her, but I just wasn't feeling it."

"Really? Why not? She was cute."

"I don't know man, I just haven't been that interested in dating recently."

"I bet you would be interested if she had been Kimberly Paisley."

"Of course. But seriously, I've just been having more fun being single for a little bit."

"I haven't heard you say being single was fun for a long time. What's different this time?"

Greg didn't answer for a beat, "I don't know, I think I'm just not trying as hard to live the way everyone tells me to live. I think I'm just, I don't know, happier's not the right word. But I'm happier just living the life I have right now. You know?"

I felt a jolt of excitement down my spine. Maybe somebody had taken a message from a local sissy a little to heart, "Well, that's good man. You should be happy with where you're at. You have a good job, good friends, and you're a good guy. There's no reason to wish something was drastically different."

Greg shook his head a little, "You know there's one thing, at least, that should be different."

"Oh," I said, feigning being uncomfortable even though my insides were on fire, "so that's still going on?"

"Yeah, worse than before, I think. But I'm trying not to be so down about it each time. My therapist says that if I treat every slip-up like a failure, I'll end up giving up."

"He's right. Quitting anything cold turkey is really hard because one relapse and you have to start all over again. You kind of have to treat it like a cool down from a run, where you still do it, just maybe at a slower pace than normal."

"Exactly...is what I'd say if I actually slowing down."

"Well, that's not a big deal. You go through cycles. Eventually, you'll want to stop."

"Have you? Stopped, I mean?"

It was my turn to pause. I thought a little bit of truth in this situation couldn't hurt, "No, not exactly."

Greg seemed to brighten at the admission, "Do you mind if I ask you a few questions about it? It's ok if you don't want to answer."

"Of course man. Honesty's the best policy with this sort of thing."

"Why do you think you watch it?"

"Well, that's easy. For me, it isn't even really about sex all that much. It's more about chasing an adrenaline high. Because I've been told my whole life that porn is evil, and it's one of the few 'bad' things I can do without lasting visible consequences to my life, it's been my way to be a rebel since I was 14."

"Really, it's not about sex for you? I had never thought of it that way before."

"Yeah, no. I mean, I'm sure my sex drive is a complicating factor in the whole thing, but if it were really about sex, I would probably have more problems with actual girls than I do. I'm just chasing a high."

"So, like, what do you watch when you watch it?" Greg seemed to realize that this question may have already gone too far. I carefully considered how I wanted to answer. Again, I didn't want to play my hand too far.

"I mean, it started out with pretty standard stuff. Just naked pictures. But I've always had to escalate at some point. Without going into too many details, I've seen stuff that I know I should be embarrassed about."

Greg didn't answer. Pressing my luck, I asked him, "What about you, if I can ask? What sort of stuff have you been watching?"

"I don't know, man. I don't really want to say."

Pretending to consider a moment, I offered, "Look, if you tell me what you've been watching, I'll tell you the worst of what I've seen. I guarantee mine is worse."

Greg didn't immediately respond. "Alright, I trust you. You won't judge me...I think. Have you ever heard of...chicks with dicks?"

I laughed out loud. Greg looked mortified, so I quickly said, "Dude, sorry, that's just what I was going to say was my worst thing."

He looked so relieved, "Oh, I was worried for a second you were going to think I was a freak or something. I don't really know how I feel about it. It's a pretty recent thing."

Feeling confident, I said, "Well, I've got you beat there. I've been watching it for a little while now."

"Yeah? What got you into it?"

"I just sort of stumbled on it. I mean, you spend enough time searching the deepest darkest corners of the internet for your next porn fix, and eventually you end up watching chicks with dicks. And you?"

"Kind of the same. Watching it doesn't mean I'm, you know, gay?"

Both Greg and I were fairly open about not being prejudicial toward gay people. We both had gay friends. But that didn't mean Greg wanted to be gay, "Nah, I don't think so. I mean, you still find girls attractive, right?"

"Yeah. I mean, like I said, if Kimberly Paisley were here, I wouldn't be able to think of anything else."

"You mean, you'd try to make out with her?"

"Yeah, pretty much," Greg said with a smile.

"You're not gay, dude. It's just, I don't know, for me, at least, there's something attractive about trans girls. I mean, if they are with another girl, or another transgirl, that's like, closer to a lesbian scene than normal porn.

"

"That sounds like some heavy justification to me," Greg said with a sly smile to let me know he was joking. Nevertheless, I felt flustered.

"No, I mean, I'll admit it, I find trans girls super attractive. I think for me, with the whole taboo thing, it's the fact that these were once guys who decided to make themselves into sex symbols. That kind of turns me on."

We both sat there for a moment. I think we both realized the conversation was weirder than we thought. But it was too late to turn back at this point. I plowed on, "I mean, why do you think you watch it, if not because the girls turn you on?"

Greg looked at me, before answering slowly, "I don't know, I'm still trying to figure that out. I guess if I had to guess, it would be, like, the power dynamic? I mean, I never watched any of that BDSM stuff like you, so I don't really get that. But I think I just like how they seem to like, want to have that stuff done to them."

Perfect. Much to my delight, it appears my emails had worked exactly as intended. Greg was turned on by sissies, and as an alpha, not as a sissy himself. But I didn't want to break too many barriers in one. Slow and steady wins the race, I had to remind myself, "Well, that's cool I guess. Nothing wrong with that. So promise you won't judge me for watching trans porn, and I won't judge you for doing the same thing."

"Agreed," he said quickly.

"Alright, let's talk about something else. I don't need an excuse to think about porn more." For the rest of the car ride, we talked about our usual subjects: basketball, world politics, economic theory, star wars. Yeah, we ran the gambit on all sorts of subjects. Soon, we were climbing out of the car. It was, like it almost always is after a good concert, near midnight. With most people still out for the holidays, our apartment complex was a bit of a ghost town.

As we approached his door, I felt that squirmy feeling I always got before making a decision on whether to do something stupid. I still had the panties on. The conversation had gone perfectly, but it was still a long way from making it a reality. I could take a gamble now. Did I want to? I had my keys in my hands as I wrestled with this decision in my head.

Before I realized that I had even made a decision, with my heart beating faster than it ever had, I dropped my keys on the ground. I bent down to pick them up, bending, not as a guy would, but how I did in my cam show: at the waist. I knew it would cause my shirt to ride up, my jeans to ride down, and my panties to be exposed, right in front of Greg's face. I didn't make a show of it - I still didn't want to be too obvious. I wanted to play it like it was late, and I just didn't think and slipped up by doing something girly in front of it. So I bent down quickly and stood up quickly, and then continued walking as if nothing had happened.

Greg, to his credit, took it in stride. It was dark, and by his reaction, I wasn't even sure he could see the panties. We quickly reached his door, and, as I was about to disappointedly leave, he said, "Can I ask you one more question?"

"Um, sure, shoot," I responded, almost twisting where I stood with anxiety burning inside of me.

"So when you said that the, you know, um, trans girls turn you on, did you mean that you like imagined yourself with one, or more like you imagined yourself as one?"

Even though this was exactly what I wanted, my cheeks started burning red because of embarrassment. I shifted my feet and looked down, "Look, it's kind of embarrassing for me to say."

"No, dude, I understand. You do you, right? And we don't have to talk about this if you don't want to. But if you're ok with it, I do have one more question."

Again, I paused. How far did I want to push this? Was I really going to try to suck my friend's dick tonight? While I had hoped, when the night began, that some progress would be made, I hadn't anticipated everything moving so quickly. Was it too late to back out? Nervously, almost breathlessly, I said, "Hey, why don't we go talk about this upstairs instead of standing out here in the cold?"

"Sure man." We were both oddly silent as we traipsed up the stairs. I shed my jacket as soon as we got inside, and he did the same. After unloading my wallet and keys to their usual places, there was nothing left to do to stall the moment.

"So, what did you want to ask me?"

"Are you sure you're ok with this? Cuz I can just go back downstairs."

"Yeah man, I'm sure. I said I'd be honest with you, and you haven't given me a reason yet to not be honest. So go ahead, shoot."

"So, like, have you done anything to be like the girls in the videos?"

The question was so direct, if not unanticipated, that my cheeks again flared red, probably giving him the answer without me opening my mouth. But I also added, for good measure, "I mean, I've experimented a little."

"Dude, don't worry, that's totally cool. I'm just curious, that's all. Like, what sort of experiments have you done?"

Greg was disarming. Despite this being my seduction plan, I think the power dynamic had shifted somewhere. I was being seduced by him, now. As it should be, I couldn't help but think. I started to relax and open up a bit more. After all, this was my role, "I mean, I've dressed up a little. Like, I've tried to see how close I could get to looking like a girl in one of those videos."

"Really? That's cool. So, I mean, are you wearing panties right now?"

Again, I flooded with embarrassment despite the fact that flashing him my panties was exactly my intention, "Um, yeah. Yes, I am. I just kind of like the feel."

"Dude, you don't need to justify anything to me. I figured you were - I mean, you had to know that I saw them. So, like, do you have a full get-up?"

"Yeah, I do."

The conversation petered for a bit right there. I think Greg was having one of those same fights in his head that I had frequently had in my head during this whole ordeal about whether we should push it further. As the silence stretched on, I opened my mouth to say something, but Greg beat me to it, "Can I, like, see it? I think what you're doing is cool, and I, I don't know, I kind of want to see it."