Just Like a Real Girl Pt. 03

Clint destroyed me that night. I felt him inside for me DAYS after our little "date," and I'd begun to think he'd had a change of heart until he messaged me about a week later. I'd more or less tried to forget about him and all the things I let him do, but the instant his message popped up on my screen my heart leapt.

"How's your hole, Krissy?" he wrote.

He knew... and his crassness made me blush a little. I deflected the question and asked one of my own, "How have you been?"

"Fine."

I waited for more, but after a few minutes I thought he'd gone. "Still there?"

He responded, "Yep."

I frowned at my computer screen; some men had a habit of doing this. They say whatever they had to in order to get their needs met, and then afterwards they sort of resented the person who met them. They liked it when you sucked their cocks, but then they judged you for it after they'd emptied their balls into you, almost as though they were saying, "What a disgusting pig you are," even though the whole thing had been their idea... their fantasy.

Though I was disappointed, I reminded myself that it meant he wasn't expecting me to follow through on our bet, which obliged me to surrender myself to a gang bang with four of his friends in a motel he described as a "shit hole."

I began writing my exit message: "Well, thanks for the night, it was interesting, I guess. Good luck to you and take care of..."

A message from Clint popped up on the screen before I could send mine, it read: "Sorry, baby-doll. I had to take a call, but I'm here now. I haven't been able to stop thinking about you, and how sweet it was to be inside you."

"WHOA," I said out loud, re-reading the remark three times before responding. "I've been thinking about you too, it was pretty amazing."

"Agreed. I think I've jerked off at least five times this week just thinking about all the little sounds I was able to get out of you. You were like some sort of hot little instrument that I was playing with my cock. It took me a while to figure out how to play you, but in the end... I made you sing, I made you scream."

He certainly had, and I'd been shunned by my neighbors several times since then as proof. I could only imagine what they heard, but between my moans and the headboard banging against the wall, I think they all deduced the same thing; there had been a man in my apartment in the middle of the night, fucking me up the ass, loudly.

"Yes," I agreed. "You didn't disappoint, three times in fact."

"I remember," he replied. "I was taking it easy on you."

I laughed out loud, "Oh, well I appreciate that."

"Don't worry, next time I'll go harder. But first you need to make good on our bet."

There it was... I'd been hoping that it was just 'fuck talk' (some erotic conversation to get their respective juices flowing before their first date,) but clearly he'd been serious.

When I didn't respond, he messaged: "Hellllllo?"

"Yes, I'm here. Just thinking."

"Okay, would you like to know more about my friends?"

I figured if it kept him talking, it'd give me time to think about how to proceed. The 'Block' button was starting to look like a plausible option, but it wasn't nearly as effective now that he knew where I lived.

"Cool," he began. "Now, I don't like to use their real names, just as they won't actually know yours other than, 'Krissy'. I call them Mike, Mark, Marshall and Matt.

They're good guys, clean, and hung like me. Well, everyone except Matt."

"Oh, what's different about Matt?"

"He's hung like a fucking horse."

I laughed to myself and felt my hole clench involuntarily.

He went on, "So like we discussed, when the time comes, you're going to drive to the motel, and we'll be waiting for you there."

"Umm," I wrote hesitantly, "I'm not sure about all that." I prepared myself for Clint to be angry, to tell me that a deal is a deal, and a bet is a bet; a contract of sorts. Instead, he was compassionate and understanding.

"I would never ask you to do anything that you didn't want to do, that wouldn't bring me any pleasure. But I'd like to tell you what I have in mind, and see if it's something that might appeal to you. How does that sound?"

"Yeah, okay. Go ahead."

"Great," he began. "Now, you and I both know that you want this, it's something you've been fantasizing about your entire life. but it's hard to find, and even harder to trust the men you meet. Am I right so far?"

"Yes," I admitted.

But you know you can trust me now, right? Not only did I not hurt you, I gave you the best fuck you've ever had, didn't I?"

After a moment, I answered begrudgingly, "Yes."

"And you want me to fuck you again, eventually. Right?"

"Yes."

"Good. I want you to do this for me first, I want to watch you get fucked by my friends. If I'm pleased by what I see, then I'll book us a weekend at a nice hotel, just like I would have if I'd lost the bet."

"Wait," I interjected, "you're not going to fuck me at the crappy motel with your friends?"

"Nope. Which brings me to the next thing I want."

He waited for me to respond, which I eventually did. "Yes?"

"I want to film it on my phone."

I sat back in my chair and sighed; the 'block' button was beginning to look more and more appealing. I was hovering the cursor over it when he went on, "I'll give you the sd-card the moment we're done so you can take the only copy of the footage with you. BUT... if you enjoy yourself and like what you see, I ask that you share it with me and my friends."

That sounded reasonable; after all I'd posted about a dozen videos online of me performing felatio on a dozen different men, and if I had the option of deleting it from existence without anyone else ever seeing it, it might not be that big of a deal.

"I'm not saying that I'll do this thing, not yet. But if I DO, you can film it, as long as I get the sd card."

"Good," he said. "So I guess the only thing left to discuss is what's holding you back, Krissy. What is it? What are you afraid of?"

"I don't know exactly," I confessed. "I guess the idea of being tied to a bed in some trashy motel and fucked by four men I just met?"

"I see. What's the most men you've been with at once?"

That was an easy thing to answer, "Two."

"Kay, so what did they do, take turns or take you from both ends?"

"Both."

"So you got fucked in the ass twice, am I correct in that?"

"Yes."

"Perfect. Well you're going to be bound and gagged, and my friends are going to take turns with your ass, one after the other. All you have to do is lie there and take it. Let me ask, when those two guys were done with you, were you totally destroyed or could you have taken more?"

Thinking back to that threesome, and two others I'd neglected to mention, I had no recollection of being 'destroyed,' or being so used up that I couldn't have taken another round. And, if I could have taken one more, then it's conceivable that I could have handled two.

"I see your point," I wrote. "So that leaves the seedy motel. I'm a little uncomfortable going to a place like that, especially dressed as Krissy. I've never gone out dressed as a girl before."

"Yes you have," Clint counteracted, "when you took those late night walks in your step-sister's panties. What you did back then was pretty risky, dangerous even. This will be much safer."

"How so?"

"Glad you asked. The whole point of doing this thing at a sleazy motel is that nobody is even going to notice you. This place has hookers and crossdressers coming and going every night of the week, and it's not like you're going to have to check in or anything. All the rooms face the parking lot, I'll give you the room number and all you'll have to do is walk from your car to the door."

I sat back in my chair and re-read what he'd said several times. Sitting there, I realized that he'd sufficiently addressed every one of my concerns, and that I was fresh out of excuses to NOT hold up my end of the bet. There was only one thing left to say.

"I'd be putting a lot of trust in you to keep me safe," I told him. "I'd be taking your word that these guys are all disease free and that they'd stop if I wanted them to. I want you to know that if these guys turn out to be total jerks or if it's anything other than you say, I won't think twice to press charges, no matter how humiliating it might be."

He immediately replied, "On the lives of everyone I hold dear, nobody is going to hurt you, this is going to be the best night of your life. And after you've done this for me, and I've made you into my whore for the night, I'm going to top it a week or two from now by showing you the other side, and making you my princess for the night."

What else could I say, what else WAS there to say except, "Okay, Clint. You're on."

* * *

I must have backed out and back in a thousand times waiting for Friday night to arrive; I flip-flopped so many times that I lost track. Just when I'd decided to stand him up (something I've never done) I'd change my mind and decide to go. Fifteen minutes later the reality of it would come crashing down on me and I'd back out again. It went on and on like that until Friday night arrived, and I was forced to make a choice.

I was still thinking about all the ways I could get out of it when I found myself rifling through my drawers looking for something to wear... just in case I decided to go. Before I knew it, I was pulling on a pair of fishnet stockings, my back satin panties and a short latex skirt. I put on a black bra, stuffed it with a pair of silicone tits, and topped it off with a crop top. Once I saw myself in the mirror, it was all over; I knew I was going.

I painted dark rings around my eyes, and made my lips bright red before pulling on my blonde wig and tying it into pigtails, shoved my feet into my stilettos and put on my black motorcycle jacket. I don't think I've ever looked so hot, or so passable. Though I'd never considered walking out of my apartment dressed that way, I knew I'd be cheating myself if I didn't. Likewise if I decided to bring along a change of boys' clothes. I slipped a tube of lipstick into one pocket, grabbed my keys and walked out before I could talk myself out of it.

Next, I walked the short distance from my door to my car, sure that one of my neighbors would spot me and call out to me, but no one did. I started my car and drove off, careful to obey all the rules of the road throughout the 45 minute drive to my final destination, terrified by the possibility of being pulled over. Terrified, and also strangely excited. After all, in this day and age, people like me were pretty common and cops were used to dealing with all sorts of weirdos. They probably wouldn't even bat an eye at a boy dressed like a girl on his/her way somewhere.

When I arrived at the motel, I was sickened to see the parking lot was nearly full. The motel was a two-storey affair with a small office and a neon 'No Vacancy' sign flashing in the window. The lot was teeming with men and women ranging from their 30's to their 50's, all whooping and hollering as they prepared for a weekend of debauchery and heavy indulgences of all kinds. The motel was shaped like an L with three sets of crumbling concrete steps leading up to the second tier. I parked my car in the only spot I could find and immediately folded down my sun visors to block peoples' view of me as I frantically searched my phone. Finding it, I logged onto the app where I'd met Clint and sent him a message.

"No way!!! There's WAY too many people here."

His profile changed to green as he logged on and he responded. "Yeah, a twenty-year high-school reunion, or some damned thing. I'm on the second floor beside the ice machine, can you see me?"

Peering out from under my rear-view mirror, I scanned the second tier until I spotted him, waving down at me from the far end of the motel.

"It's too far," I wrote. "I can't do this."

Clint began to type something, but then he changed his mind and my phone buzzed in my hand as he called me. I answered the call and immediately blurted into the phone, "I can't do this, Clint. I'm sorry but I can't!"

"Yes you can, Krissy," he said without a hint of doubt. "Get out of the car and just walk. That's all you have to do. I'm standing right here, you can see me. Just walk to me, nothing bad is going to happen to you, I PROMISE."

I hung up the phone and broke into nervous tears, ruining my eyeliner within seconds. I started my car.

I looked over at Clint watching me from a hundred yards worth of cars and adults taking a vacation from humanity; he was so close yet he might as well have been on another continent. "Fuck!" I cried.

I took a dozen deep breaths and smeared the tears from my eyes. To have come so far and risked so much only to fail within sight of the goal line, it was devastating. Clint was no longer waving, he was leaning his elbows on the faded blue railing atop the white wrought-iron which kept the occupants of the upper floor from falling into the parking lot. He watched and waited, but I was sure he wouldn't wait forever.

"FUCK!" I screamed, smashing my palms off of the steering wheel and inadvertently beeping my horn, drawing the glares of a few drunkards. I reached for the shifter and was about to put the car into 'drive' when I saw four men join Clint at the railing, and all five of them began whistling and cat-calling my name.

"Come on, Krissy! Get that sexy ass up here! We're waiting for you! Come on!!!"

"Fuck," I said.

I closed my eyes.

I'd been dreaming of this moment for decades... but now that the moment had arrived, I resisted it with every fiber of my being; I was too old, too tall, too broad, and too male to convince anyone with eyes or ears that I was the vixen I'd been pretending to be. I'd already noticed a sizeable decline in the amount of offers I was getting from men, and the reality that some day there'd be no offers at all was weighing on me. But right now, that night, there were four rather tall and strapping looking men waiting for me to come to them.

In one swift movement, before I could talk myself out of it any further than I already had, I switched off the engine, took the keys out of the ignition, opened the door and got out, locking the door and pushing it shut. Looking around, nobody seemed to notice me, so far.

I put my head down and began making the long walk to the far end of the motel, where Clint and his friends were waiting. A drunken party-goer bumped into me (or maybe I walked into him) and he said, "Sorry, sweet cheeks," and staggered off.

I was about fifty yards from my destination when I noticed a group of a dozen men walking towards me. They were clearly lit and on their way somewhere to get even more lit. I put my head down and tried to walk through them, but one grabbed me by the arm and spun me around. "Hey gorgeous, where are you going, I'm right here!"

We looked at each other for a second, and I saw the realization cause his expression to change. I yanked my arm free and continued walking, and heard someone say, "Dude... I think that was a DUDE!"

I wanted to turn back, drive out of there and forget the entire thing, but with each step my destination seemed more achievable while my car seemed far away.

I could swear that everyone there was looking right at me, and whatever conversation they were having was about me. I reached the stairs closest to the men and stopped with one foot on the bottom step. Clint called down to me, his voice clear and soothing over the din of the hordes.

"Come on, Krissy, just a few more steps!"

I looked up at the men smiling down at me, and they began to clap and cheer me on, "Kri-ssy, Kri-ssy, Kri-ssy!"

I took a deep breath and charged up the stairs, and I didn't exhale until I was safely inside. When I did, I sobbed into my hands uncontrollably, and the men quickly tried to console me. I felt a hand on my back and I heard Clint's voice, "Don't cry, Krissy... you DID it! You're here!"

I shook my head and continued to cry.

He beckoned the men to come closer and began introducing them to me. I wiped my eyes and did my best to acknowledge each of them as he gave me their made-up names. "This is Mike," he said of the first man; a lean man in his 40's with greying hair and a broad smile.

"A pleasure to meet you, Krissy," he said, first taking my hand as though to shake it, instead kissing it. "I'm very excited to be here, thanks for coming, I'm sure it wasn't easy."

He stepped aside as the second man approached and Clint introduced him. "This is Mark."

Mark followed suit and kissed my hand and tried to set me at ease with a bad joke, "Should I kneel?" he teased. "Oh wait, no that's you. I get confused. Hi. Nice to meet you."

The next man was a stout young man with dirty-blonde hair and a thin mustache named Marshall. He gave my hand a quick peck and said only, "Hi," before backing away.

The fourth man was Matt. He appeared to be the youngest of the group (I placed his age at around 24, give or take) and he looked as though he must live at the gym. His hair was cut close and dyed black, and his muscles bulged under his t-shirt. "Sup, Krissy?" He said, giving my hand one quick pump and stepping back, as though he was on a schedule, and anxious to start.

Clint nudged me with his elbow to get my attention and said, "Don't worry about Matt, we're still teaching him manners but he's good people."

The next thing I thought about was; what I must have looked like at that moment. My makeup was surely a disaster and I suddenly felt ashamed and self-conscious. "I need to freshen up, or something..."

"Sure," Clint said, directing me to the bathroom.

Once inside with the door closed and locked, I looked in the mirror and found I looked even worse than I'd imagined. Laughing at my own expense, I soaked a motel towel in hot water from the sink and began wiping my face until it was clean. Once I was a clean slate, I fished the eyeliner and lipstick out of my pocket and redrew the dark circles around my eyes, and painted my lips red.

This is it, I thought to myself. Once I walked out that door, things were going to happen that would change me forever, and my whole life since those walks in my step-sister's panties and everything that followed was all building up to this moment... this night... these men who were waiting on the other side of the door.

I took off the motorcycle jacket; I wasn't leaving, not just yet.

When I opened the bathroom door and stepped back into the room, I saw that the lights had changed; each of the half dozen bulbs were now tinted with color, each lamp and fixture was scrolling through the entire spectrum on a loop, casting a kaleidoscope on the walls. It was darker than it had been when I arrived, and I liked it that way.

The four men were standing outside the door waiting for me with lust in their hearts, and I knew there wasn't a chance in hell I was getting out of that room with my holes intact. And I liked that, too. I was beginning to feel the same way I'd felt the night I met Clint: like I was prey, meat to be consumed. And I liked that, too.

"Hello, boys," I said, breathing a little sigh of resignation. "Well, I dragged you all out here, I guess we should do this thing."

With that said, Marshall stepped forward, producing his cock in one hand and guiding me down to my knees with the other. My eyes scanned the room and I saw Clint sitting in the corner chair, holding up a digital camera as he filmed the event. Our eyes met and he gave me a little wave as if to say, 'Go ahead, I'm right here.'

I looked up at Marshall and let him do the work of taking my head in one hand and pushing his cock against my lips until I accepted him into my mouth. That was all the invitation the other three men needed before they began shedding their clothes in anticipation of their turn and within seconds their cocks were pointed at my face from all four sides. Mike and Mark stood to my left and right, and I instinctively took their cocks in my hands and began jerking them off while I blew Marshall.