Big Flipping Deal Ch. 02

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I followed her logic, along with the rest of the scheduling stuff she filled me in on: a friend of hers who did inspections - Bret - would be coming tomorrow to make sure we weren't looking at any disastrous hidden defects, then we'd move the current appliances to the garage and do all the demo work in the kitchen, paint it, resurface the cabinets, get the flooring and countertops in, and be ready for the appliances. After that, pull the toilet and sink from the master bathroom, yank the existing tile, repaint, retile, and install the new fixtures. Rinse and repeat for the guest bathroom. After that would be the paint and floors for the bedrooms, hallways, living room, and laundry room.

We went over all this at dinner after shopping - Lindsey didn't ask if I was hungry, just said she was and picked a steak place with a steep enough menu I was just going to get an appetizer until she said she was paying and would be writing it off as a business expense. "That's legitimate, by the way. This is a money-making venture, if you remember."

On the one hand, I didn't like being reminded that our relationship was really just an expedient partnership. But on the other, I appreciated her sense of ethics about write-offs and that she found it important enough to make a point of telling me.

She dropped me off around dusk and asked if I wanted Friday night off. I told her it was totally her call, and she said she'd pick me up from work at four-thirty again. I walked inside, took my shoes off in the foyer without turning on the light, and immediately stepped in the cold sog of a hairball.

"Thanks, Mister Whiskerdoodle," I grumbled. But as I hit the light switch and took off the now-wet sock to avoid tracking cat yark everywhere, I found myself curiously unirritated. I'd just spent most of the evening watching Lindsey ping-pong between enthusiasm and mind-blowing competence at the subject in front of us, and I'd gotten in a couple of jokes that she genuinely laughed at, and I felt like the next few months held a lot of promise for uncomplicated, enjoyable interactions with her.

If anything, having romance and sex off the table took away a huge pressure I'd have felt if I still thought she was a normal girl. The more I thought about it, even while cleaning up cat puke, the better my mood got.

When my head hit the pillow at bedtime, I found myself looking forward to a better Friday night than I'd had in months.

* * *

"Hi, Nick! Nick, this is Max! Max, this is Nick!"

"Wait," I said, gobsmacked to find the two of them in the bar together, and fucking no less, "I thought - didn't you break up with -"

Lindsey rolled her eyes. She had her ass on a barstool and her elbows back on the bar, legs up and skirt raised so Max could plunge freely and deeply between her butt-cheeks. "Yeah, I know. But we just keep fucking for some reason."

"Pleased to meet you, Nick," Max said, taking a hand from beneath one of her knees to offer to shake mine. I ignored it, stupefied.

"But he hit you," I said, stepping closer to the bar to get away from Max's hand. He shrugged and returned it to its grip on the back of her knee, pushing both her legs farther up and plowing into her harder than ever.

"I know," she said, shaking her head. "I'm a mess. I suck at the whole relationship thing. He's not even that good a fuck. Look, my cock's just lying there. He's not even touching it while he screws me."

Max looked surprised, as if he had a perfectly good excuse. "My hands are full of these awesome legs! Why would I let go of them to feel a dick instead?"

"Because it's just common courtesy!" I said, offended... but also distracted by the sight of his large and rigid cock sodomizing her with abandon, every thrust making her lonely, flaccid penis quiver unattended above her ball-sack. "Lindsey, why in the world are you taking this? Tell the bastard to pull out and get lost."

"Jeez, Nick, I told you you didn't want to get involved in this part of my life. I'm completely incompetent at it. But don't worry, Max is hung, but he's a lousy lover. It won't take him much longer to be done."

"UH, God! You said that right!" groaned Max, powering relentlessly in and out of her. "Oh, shit, this ass feels good! Nnf! Uh! Yeahhh... "

Incensed, I absolutely knew I ought to storm out. But the sight of Lindsey's long, pale legs raised and perfectly poised for sex kept me rooted to my spot, staring, mindlessly entranced by the way both her prick and her tits surged and jiggled at every thrust from Max's lunging tool. Her head lolled back wearily.

"God, I'm such a wreck," she said. "He's getting to fuck me up the ass, and I'm not even getting jacked off."

I couldn't believe it. This selfish son of a bitch kept burying himself to the root in the ass of the most beautiful woman I'd ever met, without bothering to even lift a finger to return the pleasure she was giving him.

"Damnit, Max," I said. "Just let go of her leg for a couple minutes and jerk on her a little. It's the least a decent human being could do."

"Ooohh - uh, uh, guhuhh. What? Oh, crap, that's some good anal sex right there. Uh-huh, uh-huh, yeah, baby... " He kept slapping it into her and ignoring me, pistoning forward balls-deep, pulling way out, veins standing out in his neck as he gasped and pumped.

"Max!"

"Fuck, man, if it's so important to you, why don't you do it? Looks to me like you've got both hands free... ooh yeah, ooh yeah... UH!"

Embarrassed, I turned to see whether Lindsey had been paying attention. Her lips looked pouty, and her blue eyes were oceans of need, but she said, "Don't worry about it, Nick. I know it's not your thing."

"No, it's not," I said, grinding my teeth. "... but Jesus Christ, it's not like I don't know how to jack a cock off."

My hand found her limp, warm length and took hold of it. With a twitch and a surge, the slack flesh fattened itself up and engorged.

"Oh!" Lindsey said, wide-eyed. "Really, you don't have to, Nick. But... oh!"

My own cock burgeoned within my pants as I began stroking her. I looked around the bar to see if any of the other patrons noticed that I was getting an erection from rubbing someone else's dick. They all seemed to be busy with their drinks and conversations.

Max sped up as I jerked Lindsey's dick with hesitant, shame-filled tugs. "Yeah, whack that thing! Dude, that's so hot! MMm, fuck! So good... "

"Nick... " gasped Lindsey, "I don't want you to... be... oh, that feels nice. But if it's bothering you... ooohhooohoo... oh, please, I don't want you to stop, but... "

I glanced from her ecstatic, sympathetic face to the swollen knob of her cock, peeking up between my thumb and encircling fingers. The stiff heat of it in my grasp felt uncomfortably familiar, not quite like the feel of my own erections, but close.

"That's it... that's it... " she whispered. "Oh, yes, keep doing that... "

Standing there in awkward silence, I kept my hand in motion as Max huffed and humped and Lindsey lay moaning in pleasure.

"Ah!" she said, her body suddenly tensing. I wondered if she was coming, then remembered that she wouldn't come the way a natural-born woman would - she'd spurt all over me. This was something else. "Nick, I know - close your eyes and pretend you're just masturbating. I'll grab hold of you while you're taking care of me."

"Uh... " I tried to think of a polite way to ask if maybe she could just take over whacking herself, but before one occurred to me, I felt the teasing trace of her finger run from the base of my crotch all the way up my fly, where she dug for the zipper pull. Instead of making my own suggestion, I closed my eyes and said, "Okay."

One-handed, she fished out my erection and surrounded it in her tender but confident grasp.

"Yes!" said Max. "Jerk each other off, both of you! Uh - fuck!"

Lindsey growled at him as she began milking my hard on. "Shut up, Max."

She matched my pace exactly, matched my pressure, did everything just right to make her hand feel just like it was mine, like I was masturbating myself and not her.

But the inescapable difference was, I could hear her whimper with pleasure every time I pulled at the rigid column of flesh in my grip, and the involuntary surges of her cock couldn't be timed to duplicate mine. So I opened my eyes again and ignored Max squeaking and thrusting between her legs and watched her face, that wonderful, sculpted face, trembling between peace and passion, eyes closed, bottom lip sucked between her teeth, brows tensing and relaxing, tensing and relaxing as we pulled at one another...

"Oh," she murmured, "oh... "

"Yes, Lindsey," I whispered. "Come... "

"Oh... "

Max's voice tried to intrude, but I barely registered what it said. "Fuck - yeah - gonna cum -"

Her sweet, lovely face held my gaze completely. Somewhere far away, my dick felt incredible as she pumped it, but all I could think about was that face, and how much I wanted to see it glowing with pleasure and joy.

"Oh... "

And there was an easy way to do it.

"Oh... "

Heart pounding, I bent and slipped my hand out of the way and took her in my mouth.

"OH!!"

She exploded the very instant I sealed my lips. Thick white ejaculate filled my mouth so quickly I gargled and almost choked and couldn't keep it all in. Max was shouting and coming so hard I could practically hear his throbs as Lindsey's spew crashed against the back of my throat and blurted from my lips to run down her shaft and onto my hand.

"Nick, Nick!" she cried, giving my cock a final, prefect twist that unexpectedly pulled me over the edge into orgasm along with her and Max. I swelled in her hand and unloaded, spouting, spurting, moaning around her pulsing rod...

And then I woke up, and Mister Whiskerdoodle was purring on my chest.

"Agh." I looked around and saw that the clock said 2:18 a.m. My head flopped back into the pillow, still fuzzy with dream-stuff but also awake enough to have at least one coherent thought. "Fuck, Mr. W... I think I may be in real trouble here."

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
22 Comments
IanSaulWhitcombIanSaulWhitcombover 3 years agoAuthor
@Raquels_Panties

I'm glad you found it too, and even gladder that you liked it!

Raquels_PantiesRaquels_Pantiesover 3 years ago

Great story. I’m glad I just found it. I like the characters and the fantasy sex is hot.

IanSaulWhitcombIanSaulWhitcombabout 4 years agoAuthor
@Anonymous (Overall, it’s a good story)

Glad you at least like it overall! Sorry not all of it worked for you... but then, if the same things worked for everybody, there probably wouldn’t need to be near as many stories on this site!

AnonymousAnonymousabout 4 years ago
Overall, it's a good story.

The imaginary sex does absolutely nothing for me, whether it was between man and woman, or man and trans-woman. I just skip over most of it.

IanSaulWhitcombIanSaulWhitcombover 4 years agoAuthor
@erythrina

Sorry if I should have put a trigger warning in front of this one, but I really meant to imply that this was the first physical violence that had ever happened between Max and Lindsey, and that it really was more of a drunken escalation than an abusive situation. The instant it happens, both characters immediately know that they’re done forever, whereas abusive relationships are all about gaining and keeping control, not losing it. Your comment does make me feel like it does some disservice to the issue of domestic violence, though, which I’ll make sure I’m more mindful of in the future.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Shemale Intern Lawyer Rob falls in love with the transwoman at his firm.in Transgender & Crossdressers
"What Does She See in Him?" A high school boy finds the girl of his dreams is a bit more.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
My Adorably Hung Summer Roommate Darren meets Danielle, a petite redhead w/ something extra.in Transgender & Crossdressers
My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
More Stories