Big Flipping Deal Ch. 03

I bristled a little at the idea of somebody treating her that way - especially at the idea of more than one somebody doing it. I wanted to say something sympathetic, or maybe something that would display my outrage and chivalry. But I suspected I'd only embarrass myself going that route, so I just answered her question.

"I have no self-confidence with women. Any halfway decent-looking girl who pays attention to me can use me as a doormat if she plays her cards right. I'm kind of a trusting schmuck."

One of my neighbors drove by, headlights on. I wondered if it puzzled them to see me walking down the street with this monumentally foxy woman.

"There's a lot worse things to be than trusting," Lindsey said. We reached the end of the block and turned. "I'm the world's biggest excuse-making machine when things start going bad. 'He's just under a lot of stress.' 'It'll get better - I'll just wait his mood out.' 'Nobody's perfect.' That last one's my big one. And it's the dumbest one. Sure, nobody's perfect. But lots of people aren't absolute dickwads."

"That's a good point," I said. "I get pretty cynical sometimes about the prevalence of dickwadism."

She laughed. "'The prevalence of dickwadism ...' I like that. But I try to tell myself it's not so bad. I mean, we're two for two right here in terms of people who aren't dickwads."

"You might not say that if you knew how many times I've checked out your ass and tits."

That brought an even louder laugh. "You think I don't know?"

More color flushed into my face. "Well ... I thought I was being pretty careful about it."

"And the fact that you tried to be careful means you're not a dickwad. Assholes don't hide it. When I see a guy trying not to look, it scores some points with me."

"Whew," I said. "I must have scored a lot of points today, then."

I kept walking two steps before I realized she'd stopped.

"Today?"

Oh, shit. She was talking about when I still didn't know she was ...

"Well, uh ..."

She started walking again, looking at me with one eyebrow raised. "I guess you managed to get a lot sneakier. Really? You're still checking me out, even now that you know?"

Up ahead, the stoplight at the neighborhood entrance did an imitation of my face.

"Okay, sure," I said, figuring it was best to just come clean. "It's not like you're any less hot, and it's not like I have to worry what's in your pants anyway."

"Huh. That's pretty broad-minded of you, Nick."

"I guess I'm just a broad-minded guy. At least, when it comes to staring at stacked chicks in smoking sexy outfits. That totally brings out my enlightened side."

She chuckled. We crossed another side-street, now just a block from the traffic light. Something on her face, the next time she looked my way, made me think she was about to ask me another question.

But she looked forward again, and we kept on toward the quick-mart.

* * *

At home that night, I needed something to get my brain clear of Lindsey's lips, moving nimbly as she bit into each slice of pizza while her body stood propped artlessly against her aunt's kitchen countertop. We'd talked over the plan for tomorrow - Saturday - but once we finished and I carried the half-empty pizza box back to my place, I realized that I remembered absolutely nothing except the look of those lips. Horny and fixated, I decided to surf the net for porn - and began a steady slide in entirely the wrong direction.

My starting point was a free site I sometimes have pretty good luck on, and I clicked through and into a bunch of videos looking for one I could sit back and let roll all the way through. The only criteria I meant to use was whether the scene had a hot chick getting screwed. I clicked indiscriminately at first, a brunette here, a redhead there, a blonde here, an asian girl there. Then a blonde here, a blonde there, a sandy-haired brunette here, a blonde there. Something about every video fell flat ... picture too grainy, angle all wrong, all the action shot from a medium distance with no closeups. This blonde's breasts too small, that one's too fake and inflated. This one too many tattoos, that one too many piercings.

Finally: a gorgeous woman with soft, pale skin and red lips, blue-eyed, golden-haired, vamped up with eyeshadow, starting off the scene in a tight white dress that I told myself wasn't part of why I picked her. Just like her overall similarity to Lindsey wasn't why I picked her. It was all because she was really hot and the picture quality looked good and the preview image showed her getting reamed with her legs up and an incredibly sexy expression on her face.

So I watched and whacked, made it through the warm-up blow-job without shooting my wad, and got ready for the good stuff as she settled onto her back and her partner crawled into place, lifting her legs, tapping her clit with his dick as she moaned and took in several deep, sultry gasps.

And then, when he shifted and positioned his cockhead and thrust forward to penetrate her, I thought, I wonder what that would look like if he was fucking her ass and she had a cock.

What ... the fuck.

Concentrate, Nick! Look at that smooth, luscious pussy getting filled up with cock. That could be your cock. She's taking it. She's taking your cock.

"Take it, baby, take it ..." I murmured to the screen. The porn chick strummed her clit and sucked her lower lip between her teeth as the guy kept pumping her and I kept stroking off. But what if, instead of strumming her clit, she was ... "God damn it! What is wrong with me?"

I wasn't getting anywhere. I stopped the video.

Okay, so ... what? What are you going to do now?

I'd already banged off while imagining myself in Lindsey's ass. I'd already dreamed of sucking a giant load out of her dick. What the hell, why not just satisfy my curiosity and go to the she-male category and see what it looked like?

I moved my cursor over to the sidebar and scrolled down. The hyperlink to "She-male" highlighted itself. One of several categories I never expected to check out. Would I click it?

"Dude, it's a total win-win, right?" Either I'd be grossed out and have my heterosexuality confidently reaffirmed, or I'd find it hot and be able to get off.

I pushed the mouse button.

And there I found myself, in front of a screen full of preview stills that featured long, glossy-haired figures with all different sizes of breasts - and all different sizes of penises, usually flopped toward their bellybuttons while a slick erection had itself jammed up their asses. For some reason, there were surprisingly few blondes, and as long as I was in for a penny, I might as well go in for a pound and find someone as close to Lindsey as I could get.

Click. No. Click. No. Click ... ehhhhh ... no.

Some had faces way too manly for me to take. Others started right off talking in flouncy gay accents that would never come out of Lindsey's mouth. Breasts too fake, shoulders too broad ... ass too flat.

Then I found one who looked close. I crossed my fingers and clicked through. Watched her unzip a guy's pants, fish out his tool and start licking, lapping, enfolding, bobbing. So far, it could almost be any hetero porn, except that the corner of the girl's jaw had a little too square an angle. And sometimes when her head tilted a certain way, the curves of her forehead and brow came off a little too strong. She could damn sure suck, though, and that let me put myself back in Lindsey's convertible, sycamore leaves waving overhead as she went down on me. I worked my cock experimentally. It felt pretty good.

On and off and on and off the guy's pole, she slurped, leaving him gleaming with her spit when her face retreated. He moaned and encouraged her, speaking in the low porno poetry of Iamdick prickjamminher. But I didn't need it to be Shakespeare. I just needed it to be ...

"Lindsey. Yeah, suck it, Linds. God, you're so good at that ..."

I don't think I ever had a surreal porn experience before, but that word exactly covers it: surreal. I felt disembodied, almost like I was watching myself watching the screen. This is so fucked up. I should not be enjoying this. My dick mostly disagreed, though. By this time, it was leaking silky beads of precum from the fully expanded, swollen head. I fingered the slick fluid and rubbed it around, pretending my newly slippery fingers were the she-male's tongue licking at the underside of my shaft.

"Lindsey ..."

Onscreen, the transgender starlet popped her mouth free of her co-star's engorged prong, a strand of saliva bridging the fresh gap between her lips and his cockhead. She stared up at him a moment, then licked, and the strand fell free. "You ready to fuck me, baby?" she asked. "Yeah," he said suavely.

Standing, she turned and moved to the bed, slithering out of her dress as she went. The guy followed her in that awkward way you see in cheap porn where the shot isn't framed up right and the couple for some reason goes in single file even though in real life the guy would just find his own path across the room. But in porn, you can't have him blocking the camera's line of sight to her, so single-file it is.

With her panties and lacey bra left on, she still looked very feminine, curved in the right places and showing soft spots of body fat where guys don't usually get them. The camera followed the two of them as she crawled backward, rubbing her crotch provocatively, and he got onto the mattress on his knees, his clothes peeled off along the way. The teasing caress of her hand alternately concealed and emphasized the way her panties mounded downward more fully than a regular girl's would. I had my hand going strong on my dick now, with that burn of forbidden temptation hovering between the top of my heart and the base of my throat. In a second, I would be masturbating to a view of someone else's cock, no vaginas in sight, and right after that I'd be whacking off to anal sex between two sexually male individuals.

Really fucked up.

The blonde got on her back and clutched and kneaded her breasts, tongue extending to run slowly around her parted lips. The guy took hold of her panties. She lifted her hips, and he gradually brought the frilly lingerie down - until a cock came out of it.

"Geez. Well, that's kind of small," I said, my hand slowing and loosening slightly but not stopping.

She lifted her legs, to make it easier to get the panties all the way off them, and the movement made her smallish, pale prick loll up to point at her bellybutton. The scrotum beneath it looked almost miniaturized.

My eyebrows furrowed. Is that what you look like, Lindsey?

In a close shot of her face, the she-male gave her partner a look of hungry enticement. Then the camera backed off again to show him rubbing his tip at her asshole, right below that dainty little ball-sack of hers. I noticed he had a condom on now - they must have taken a break for that and maybe some lubing up before cutting to her face?

My whole chest felt like steam.

Is that how things went with you and that Max asshole when you fucked him?

The guy pushed in. The t-girl groan-squeal-grunted as the condom-covered dick moved steadily forward, gliding, filling her up, plowing its thickness deep into her rectal recesses. "Uhh, yeah, put that in me - put that in me!"

With a ramping acceleration, he began humping her - barely moving out and back in, then easing slowly in each direction, then faster, then faster. Both of them grunted and moaned.

I squinted a little to keep my focus on her and on the cock lunging into her ass. My own dick filled my hand with rigid pleasure as pumped it. In a whisper, I said, "Yes, Lindsey, you like it, right? Take me in."

They were really going at it now, her legs up over his shoulders, his hips pounding and jamming, the power of their sex rocking her breasts and still-slack penis as she gritted her teeth and made staccato fuck-sounds through them. On and on they screwed, changing positions after a few minutes to let him doggy-style her, hands grabbing her waist as he pummeled her butthole. Her bra had been pulled free of her tits by this point, and they dangled and swung with every thrust. Periodically, the angle showed her little cock making a pendulum of itself to the same rhythm.

I was getting close. But ...

You're just so much prettier than she is, Lindsey. And that wasn't any insult to the porn actress, who had it going pretty well herself. So much prettier, Lindsey ...

The scene made one of those random cuts then, and she was on her back again, legs up all the way to her shoulders, his prong slamming repeatedly into her as she whacked herself off with rapid-fire jerks. Finally, her cock looked at least semi-erect, and big enough for the head to poke out between her thumb and forefinger while the base sat at the bottom of her fist.

Holy shit, yes! Come on your own tits, baby!

My dick swelled in my hand. I slowed my pace a little, wanting to squirt at the same time she did.

"Come on, Linds ..." But it was getting harder and harder to see her as my house flipping partner. "Damn, I wish she was as pretty as you ..."

The she-male jacked away with a vengeance. I did the same. The guy lunged and pushed and stuffed himself into her like a piston.

I bet your cock is bigger than hers, too, Linds.

Really? Why in hell did I go there?

"Come on, come on ..."

But the longer the shot went on, the more obvious it was she wouldn't get there. Her whacking was desperately fast but mechanical. Her groans of pleasure had taken on that forced, over-the-top quality that tells you porn stars are faking it. Then the scene cut to her kneeling in front of him as he worked toward masturbating his load onto her face.

I grabbed the mouse and backed the scene up a couple of minutes.

"Come on, Lindsey, we're going to make you come. Let's do it, let's make you come. God, your ass feels so good - I'm going to shoot my load in it ... come with me, come on, baby, let's get you there ... here, damn it, let me take over!"

And I shut my eyes with the image of his dick penetrating her asshole, made it into my dick within my head, gently brushed Lindsey's hand away from stroking her cock and replaced it with my own.

"Yes, so much bigger than that porn chick ..."

Then I was jacking myself and jacking my house-flipping partner at the same time, while porn groans came out of my speakers and I fucked her in the ass and felt her tensing up and saw the uncontrollable tension of ecstasy twisting her beautiful face.

"Yesss, Lindsey, cummmm!"

The orgasm hit me, and in my mind it hit her too, and we both groaned and spurted, me deep inside of her, her in great, arcing jets that drenched her tits and belly in the white milk of desire.

When I opened my eyes, the she-male in the video had just gotten her wide-mouthed face jizzed all over by the guy, which somehow seemed lame and sordid even though I'd just totally gotten off on the idea of Lindsey with semen spewed all over her front. I wiped my hand and X-ed out of the browser window before it made me feel any cheaper.

Well, I was imagining her coming on herself, not me coming on her.

That wasn't really exploitive, was it? I mean, I just came all over myself, right?

Yeah, but I agreed to be in my masturbation fantasy, and Lindsey didn't.

Why in the world I would bother with an internal debate about this, I had no idea. I mean, I must have used hundreds of different women for my masturbation fantasies without worrying about whether it was rude or opportunistic. And then, just as quickly, I did have an idea. In fact, I knew exactly why: to avoid thinking about the fact that I'd just whacked off to what most people would think of as gay porn - and the fact that I was dangerously close to getting a crush on a woman who had a cock and no vagina.

Close to? I asked myself.

Yeah, it was pretty clearly worse than "close to."