The Chance Fantastic Pt. 05

I took a breath. This is it. The absolute point of no return. I gave the power to Greg, "I mean, I trust you, Greg. The fact that you haven't started laughing at me, or left because you are creeped out means I can trust you. But you have to know, I only wear the full outfit to like 'get into the mindset.' I'd go put it on for you, but you have to understand, it wouldn't be me that comes out of that room. It would be somebody else, and I don't want you to be freaked out by how I act when I'm in that outfit."

Greg considered for a moment, "Like, what do you mean, 'get into the mindset'? It's not just you in the outfit? I'm confused."

"Look, you know how when you're watching porn, you start to get really into something, and you find it really hot, and you might even start acting a little differently, and then you orgasm, and you look at what you were watching, and you're kind of disgusted by it?"

"Yeah, definitely."

"Well, that's kind of what it's like for me. I get dressed up to get more into the porn videos I watch. So when I'm wearing that outfit, I'm kind of in that mindset that I am one of the girls in the videos, and I start acting like it. I even call myself a different name in my head when I'm wearing my outfit. So, like, I'd totally go put it on for you, but I can't guarantee that it won't creep you out when I do."

Again, a momentary pause, "What do you call yourself when you're dressed up?"

"Riley." I had picked the name of one of the sluttiest porn stars I knew.

"So, like, if you went and got dressed up and came out for me, I should call you Riley and not expect you to be, like, you?"

"Yeah, pretty much. Do you still want me to go get dressed up? Cuz we can just forget about the whole thing too." I was kind of hoping he would choose the latter option. But as surreal as this night had been, I knew what he would say.

"Ok, yeah, I get it. I think I'd still like to see you in your outfit, if that's ok."

"Ok. It takes a while for me to get ready - it's a whole process. You don't mind waiting a bit? I know it's late." I think it was one more chance for me to give him an out. He didn't take it.

"I'm cool. I'll just wait out here on the couch."

I went into my room, and as soon as I shut the door, I had to shut my eyes and take a few deep, calming breaths. Tonight was insane. I was going to suck a real dick. And not just any dick. My friend's dick. Was I insane? How did I get here? Why did I want to do this? But I did. I could tell that my hands were not shaking solely because of nerves, but also because of excitement. Huge, rushing, heart-throbbing excitement. I quickly got undressed, even the panties. I wanted to do this right.

I first rubbed myself all over with lotion. Next, I carefully applied the breast forms, taking care to make sure they were even. Then came the corset. I didn't need the clips this time for my nylons, as I had bought a pair that was sort of a combined garter belt and nylon, with stretchy fabric running down the sides of my hips, framing my ass. Next came the purple panties. They really popped against the black of everything else.

For my outer outfit, I first pulled up a purple plaid miniskirt I had recently bought specifically to match the panties I was wearing. For the top, I chose a loose, half sleeve crop top. It covered the corset completely, except the straps, and to me, it came across as cute and demure, covering the sexy slut underneath. My face was the next project.

I did all the steps - foundation, contouring, lipstick, and gloss to give my lips an inviting wet looking sheen. I chose a pink as my color, but not too bright. I didn't have that many colors to choose from. Purple might have been better, but I hadn't invested in that. Lashes, eye shadow, and mascara came next. The person looking at me now looked like a girl, albeit with shorter hair. Which meant that the next step was the wig - dirty blonde, like the dirty whore I wanted to be, with wavy hair cascading down just past my shoulders.

The last step was stepping into my high heels. I turned, gave my skirt a twirl to show my pert ass. I thought I looked good. If I didn't, I don't think I could have made myself go out. But the whole product was a lot closer to the girls I had seen than I ever thought I could achieve. I had curves in the right places. My ass was nice and pronounced at this point. I was just slim enough to pass for a girl. My face, round and uninteresting as a guy, became softer and narrower with my makeup. I looked cute. The eyeshadow and lipstick pushed me into sexy territory.

Mentally, though, I still had to get into character. I wasn't myself. I was Riley. I wasn't an unassuming guy. I was a cock-hungry whore. Now was not the time for subtlety. I was going to go out there, flirt, tease, and seduce. I was going to make love to a cock. I was going to feel warm cum on my face and tongue. Now was not the time to think about long-term consequences. Riley was about living in the moment. Riley was going to see if she could make a guy pitch a tent in his pants in real-time.

With this mantra running through my head, I didn't hesitate any longer to open the door. Making sure to put each foot right in front of the other, to give myself a distinctive sway as I walked, I came into the open. Greg didn't see me at first. Our couch was facing the door to the apartment, with its back to the hallway. So, mustering up my best female voice, I said, "Hey, babe." I kept my voice quiet, not trusting a stronger female voice to sound like anything other than a guy pretending to be a girl. It came out breathy and tremulous. Not my best - I would have to keep my vocal demonstrations to a minimum.

I didn't bother to stop after I said that. I kept walking right into the room, so that he could stare at my ass. Once I got to the center, I jutted out one hip, and looked over my shoulder. I tried again, "What do you think?" this time, with a little more confidence. It was...passable. Clearly not a natural girl, but girly enough not to break the illusion.

Greg stared. It was hard to read his face. He managed, "I...oh, wow." I did a little spin for him, so he could get the three-sixty view. He was at a loss for more words. Maybe he was regretting his decision. Maybe he was just doubting the next step. Maybe I had really stunned him. All I knew is that I had to be bold.

Running my hand up my own thigh, lifting my skirt up just enough to give him a peek at my panties, I asked, "Is this what you wanted to see, stud, or were you hoping for...more?"

He was sitting, so I couldn't get a good look at whether he had an erection or not. However, he was sweating just a bit, and grunted, "More, I think."

Smiling coyly, I batted my eyelashes and flicked my skirt a bit. Biting my lower lip, I started to sway my hips, turning as I did so. Bending at the waist, I lifted my skirt so he could get a full view of my panties. I looked over my shoulder and asked, "Do you want to get a little closer?"

He didn't say anything, but he stood up. He was pitching a big tent in his jeans. Reaching out my hand, I grabbed his hand and pulled him closer. Feeling the tip of his dick press gently against my ass cheek, I lowered my ass down just a bit, and then I started rubbing it up and down the cock in his pants. Still holding his hand, I guided it to the round curves of my ass, "Would you like to touch me, Greg?"

Again, he didn't respond. He seemed to be a little mesmerized. But he did release my hand and place it on my ass cheek. "Go ahead," I said, "give it a little slap. Show me who's in charge. I'm just a naughty girl, after all." And he did. It didn't hurt at all - he didn't hit me near hard enough to do it, but I gave him an "ooh," anyway, along with a giggle and a jiggle of my butt against his cock. I stood up and turned to face him.

We were about face to face at this point. He didn't back away. I had grabbed power back, it seemed. I was in control, for now. Let's see if I could unlock the alpha in my friend. I took a tiny step closer, so I could feel his breath on my face, and I lowered my hand to start rubbing his cock through his pants, "Do you want me, babe? Do you want to feel my soft lips on your big, hard cock?" I practically whispered the words in his ear.

Without warning, he kissed me. Wrapping one arm around him, he gripped my ass, and his tongue broke through my mouth's defenses. I think I had done it. As he kissed and groped me, I guided his other hand to the base of my shirt. Once there, he got the message and started to pull it off me. At the same time, with my other hand, I started to pull my skirt down. About the same time that we had to break the kiss to get the shirt over my head, I kicked the skirt safely away.

Not wanting to lose momentum, I smiled, "Now that I'm stripped down, what do you say about showing me yours?" Not waiting for an answer, I kneeled on the ground and started on his belt. He didn't stop me. Soon, I had his jeans down around his ankles. I could already see a bead of pre-cum soaking through his underwear. Those were much quicker to pull down.

And there I was, kneeling on the floor, with a six-inch cock staring me in the face. I could see, even in the dim light, a slight glisten on the tip of pre-cum. What came as a nice surprise for me was that Greg was clean-shaven down there. While I had nothing against a hairy man, for my first time, I was glad I wouldn't have to deal with pubic hair. The lack of hair made the cock look so much larger than my own (currently straining hard against my panties). His cock curved slightly upward. It was an average thickness, with a few delectable veins running down the shaft, and a generous ballsack. All in all, it seemed like the perfect cock to lose my oral virginity to.

I didn't have time, however, to get lost in admiration. I had a show to put on. At first, I just raised my hand, and generally stroked the underside of his cock. Given the cold weather, my hands provided a distinct contrast, even with the delicate touch. I then moved down and cupped his balls. I looked up and smiled at him, "You have a wonderful cock, Greg. Do you mind if I give it a little kiss?" I said demurely. He just nodded.

Not moving too fast, I put my head at the base of his cock, where his torso meets his leg. I could smell him. It wasn't a bad smell - Greg was fairly well-groomed. But it was a manly one. A human one. A real one. It was intoxicating. Gripping his cock delicately at the end with my left hand, I placed my right hand on his knee. I started to slowly knead the tip of his cock, and I leaned in and kissed the very base of it. It was just one kiss, but then I planted another one that lingered. I took my tongue, and I traced the outside of his balls, starting at the base and working back up to where I was before. I then took them in my mouth. I didn't really suck. I just smelled him, and let him feel the warmth of my mouth, and the gentle caresses of my tongue.

Skin, as it turned out, didn't taste too bad. It didn't really taste like anything at all. My dildo had a manufactured taste, something chemical-ly and false. Greg didn't taste like that at all. He just tasted warm and real. I could get used to this.

I gave his cock another kiss, looked up at him, and said, "I want you to use me, Greg. I want you to do whatever you want to make yourself feel good. I don't want you to ask for permission. If you want to put your cock somewhere, I just want you to do it." To show that I was serious, I laid his big cock across my face, with his balls under my chin and the shaft running along my nose. I stuck out my tongue, so I could tickle his balls with it.

For my next move, I grabbed his shaft, and rubbed his cock on my face, giving my cheek a couple of slaps, just as I had seen done to countless sluts beforehand. It was exhilarating. Greg was starting to get into it. He was loosening up and relaxing. The hotness of the situation was overcoming his instincts to think this was weird or unnatural, I thought to myself. Now it was time to ramp up the action.

I moved back and put my lips on the tip of his cock. I stuck out and swirled my tongue around it. Like his balls, it just tasted like him. I did catch a taste of precum though. That was a little more distinctive, mostly because it was actually liquid. But again, it wasn't bad - it was certainly better than cum. As I let the tip enter my mouth even more, I made sure to build up a lot of spit. I wanted this to be a sloppy blowjob. That's what I liked, and I was certain Greg would like it too.

I felt a hand on the back of my head. He didn't push. It was just like he wanted to hold it there to make sure I kept going. He had nothing to worry about. I was so into this - I had no desire to stop. Taking charge, I pushed him a little, back into the couch, so that he sat down. With a better angle, I could really get to work.

I started to move down his cock with gusto. I was no longer working delicately. Now that I had him in my mouth, I wanted him to feel my enthusiasm. I wanted him to cum, and I didn't care if it was fast. I made sure to keep my tongue under the shaft for a little extra lubed-up friction. It was difficult and took a conscious effort. That was something I didn't have to worry about with my dildo. But I figured the roughness of my tongue would be a little more stimulating than just the smoothness of the inside of my cheeks.

I couldn't keep up my pace forever. I paused for a bit without taking his cock out of my mouth. He was breathing pretty heavily now, and I knew that I could get him to cum pretty soon. I looked up at him, made sure to make eye contact, and moved his cock into the side of my mouth, letting him stretch out my cheek. I gave him a bit of a tongue bath while it was there, and then I smiled and took him out. I was pleased to see a string of saliva remain attached between my lip and the tip of his cock. So hot.

"Are you gonna cum for me, Greg? Do you want to cum in my pretty little mouth? I want you to cum on my tongue, Greg. I want to taste your cum so badly. Will you cum for me?" The end of my dirty liturgy practically came out in a moan.

"Y-yeah," was all he managed weakly.

Bracing myself on his legs, I went back to work on his cock, preparing for the deep throat. He was about the same thickness as my dildo, so my mouth was already fairly adjusted to his size. But he was harder, and less flexible that the silicone cock, and I didn't know how the upward curve would work going down my throat. But I was determined to try. I positioned myself a little higher, to get a better angle, and as I plunged down once more, I felt his cock start to hit the back of my throat.

As usual, I immediately started to gag a little bit. I knew by now how to keep anything disgusting from coming up, so this gag just produced more spit and coughing. The spit was starting to trickle down the sides of his cock, glistening at the base. He started to sit up, "Oh, are you ok?"

"Don't worry, baby, your cumslut just can't get enough of your cock. You lay back and get comfortable,and just let me work my magic." I could feel my eyes still watering from the first attempt, and I knew it was causing my mascara to start to run in the sluttiest way. I started again, and this time, when the choking started, I paused, letting the tip of his cock just dangle at the back of my throat, mentally forcing myself to get through the gag reflex.

I felt hands again, forcing me down further. Luckily, I was ready. His cock made my throat bulge ever so slightly. I couldn't breathe through my mouth, so I took deep breaths through my nose. I buried my face in his public area. After a second, his grip loosed, and I could start bobbing up and down, never letting his cock quite escape my throat area. It didn't take long before he started engaging again, thrusting up ever so slightly. It made me cough, and spit spilled out of the bottom of my mouth, but I kept going. I could feel him start to tense up. I didn't want him to lose his orgasm, but I also didn't want him to just cum straight down my throat.

I extracted him from my throat, but I never let him leave my mouth. I used my right hand to start to stroke the base of his cock while I bobbed up and down on the top half, using my tongue to massage the bottom of his cock-head. Greg had been a pretty silent performer up to this point, but he couldn't help but groan as he grabbed my head and kept it there. Cum shot into my mouth. Instinct made me try to get off of him, but his hands kept my head still. Wave after wave battered the back of my throat, and filled the inside of my mouth. I could feel some of it escape, dripping down the sides of his cock.

Soon, he was done. I could feel him relax, ever so slightly. I pulled myself off of him, swallowed, and showed him my clean tongue, "Did you like that baby? You just relax. It takes a big man to cum like that." Just like the girls in the videos, I put his cock back in his mouth even as it softened, to pick up the residual cum.

Greg did relax. I could feel him slump down even further into the couch. Both physically and mentally, Greg was likely exhausted. Me, I had climbed up onto the couch with him, my head still in his lap, cleaning his cock. I was still on fire. I had just had the most erotic experience of my life, and I hadn't even come close to cumming. Honestly, I loved it. I had no regrets about embracing the role of a sissy.

After a while, I wasn't sure if Greg had fallen asleep or not. His breathing had become slow and rhythmic. I was still face to face with his cock, which was completely flaccid at this point. It didn't look all that different from mine when it wasn't engorged. I knew he could feel my breath on his penis.

Almost absentmindedly, I started tracing the outline of his cock with my finger. I started to think about how hot I felt with my face pressed up against his groin, his cock down my throat. I almost couldn't wait until next time.

And then I realized that I didn't really have to. Here I was, with a cock right in front of my face. I didn't need to wait for permission. As a sissy, it was almost my duty to stay cock-hungry until someone told me no. Besides, wouldn't it feel great just to see if I could get him hard again?

I moved ever so closer to the cock, and put it in my mouth. It felt different, when it wasn't hard, much more like what his balls felt like. I couldn't really bob up and down on it, but I started to swirl his cock around in my mouth with my tongue. I started to move my body so I could get a better position. I took in my and more of his cock, with half a mind to try and get the whole thing, balls and all in my mouth. However, just as I started to lift his ballsack to get it over my chin and into my mouth, I started to feel him twitch and grow hard.

I looked up and saw that he was awake. There was a moment. Our eyes met and he realized I wasn't done. I was sitting there, his previously soft cock in my mouth, and he realized this wasn't a one-time thing. I was still dressed up like a slut, and he realized that I was a cock-hungry bimbo that he could do anything to.

He sat up and grabbed me by my shoulders. He practically threw me onto the couch. I could feel him roughly pull my panties down. As excited as I was, I was aware that anal sex with no lube wouldn't be fun, but I couldn't bring myself to break the illusion. Whatever was going to happen was going to happen. I was just along for the ride.

Greg positioned himself above me, and I felt his warm meat slide between my ass cheeks. I had to encourage him just a little, "Ooooh," I moaned, "your cock feels so good on my sissy ass." Greg continued rocking back and forth, not penetrating me, but rather using my ass cheeks to get him hard. To me, it felt great. Not necessarily physically - it was just a little friction that neither hurt nor pleasured - but rather mentally. He was using me like the sex object I wanted to be.