tagTransgender & CrossdressersBig Flipping Deal Ch. 07

Big Flipping Deal Ch. 07


[The story so far: Nick and Lindsey have inherited a house they must remodel together according to her aunt's will. As their DIY renovation proceeds, Nick falls hard for Lindsey even though he soon learns she's transgender and has a cock. Despite Nick's enthusiasm, Lindsey is dubious about getting involved with a guy who has previously been entirely straight, but she agrees to go bowling with him, and then to his cousin's wedding, and then on a date to the art museum. At each point, things go a little further, and the museum date ends in mind-blowing sex at her place.

Obligatory note: This chapter contains some brief references to the characters' teenage years, but at no point are any sexual activities described involving anyone under eighteen.]

A while later, even though things hadn't gotten as messy as they might have, we went in and cleaned up in the shower. Her bathroom surprised me by being ritzy but not amazing.

"Well, this is nice," I said as she ran the water in the glass-enclosed shower stall. "But after your sketches and the photos on your website, is it okay if I admit to being a little disappointed?"

She just laughed. "If you're going by the stuff on my site, you'll be disappointed with how Neena's turns out too. Those shots are from twenty- and thirty-grand bathrooms, Nick! I got the complex to let me recarpet the upstairs here - you should have seen the eye-stabbing shit they had in this place - but no way am I spending that kind of money on a bathroom someone else owns!"

Satisfied with the temperature, she got a scrunchie and put her hair up. "Come on, let's get sudsy."

The shower could have done with some more artistic tile than the polished brown granite they'd used on it, but it had plenty of room for us both. I barely even got splashed as Lindsey turned herself in the spray. But once she'd thoroughly and glisteningly soaked herself, she angled the showerhead at me and wetted me down with a grin. Then she glopped way more body wash across my chest than necessary, so that it ran and dripped down my abdomen and legs.

"Whoa, that's kind of a lot, isn't it?"

"No," she said, smearing the thick green gel around. "It's just the right amount for two."

Her soaped-up hands went around my back, and she flattened herself against me to rub us together in full-body contact. We kissed and slid chest-to-chest, belly-to-belly. Almost immediately, I felt her erection swell along my inner thigh and then bump into my own rapidly hardening prick. She got a hand between us and soaped me, tugging a moan from my throat and bringing me to full arousal. As my absolutely thrilled cock kept one hand busy, she used the other to glide body wash up from my chest around my shoulders, onto my back, down my ribs, under my arms. But she kept her hip against mine so that her dick tucked itself into my crotch by my balls, where I couldn't easily get a hand down to it. I took that to mean she had things where she wanted them, and I concentrated on kissing her and lathering her breasts and then shoulders and then ass with both hands. As we got well-soaped, she continued stroking my rod and also lightly fucked her cockhead down into my groin.

"Here," she said, swirling her hand to signal a change, "this is fun - watch."

She stepped back an inch or two, which let her cock spring up from between my legs, then lifted mine into a vertical position and caught them both in the same hand. Instead of her fingers, palm, and thumb completely sheathing me, I now had fingers around the top side of my shaft and the belly of her erection against the bottom.

Fascinated, I watched her jack her hand up and down us both, feeling the stroke with half my cock while her hot, hard flesh nestled almost motionless against the other half. Then she thrust with her hips, making the swollen pink tip of her dick rise up out of her grasp higher than mine, while the shaft worked itself slickly along the sensitive underside of my own.

"Wow," I said, my throat tight. The unexpected blend of sensations all around my manhood took me completely off-guard.

Lindsey grinned. "I know, right? This is why I love to shower with a guy who's the same height. Well, one reason."

She alternated fucking herself against me and masturbating us both with her slippery hand ... watching me as I stared, then watching our dicks slide together, then watching my face again.

"You can join in anytime you want," she prodded.

I looked up to find her smirking, which brought a rush of blood to my face. "Oh, right, sorry. I'm just kind of stunned by you, Lindsey."

The smirk turned to a smile. "Well, I won't hold that against you, then. I'll hold this against you instead."

Bobbing her hand up and down our trapped erections, she came in for a kiss, and the next time her grip went still, I tried a thrust up into it and was rewarded with a soft, "Mm-hmm," from her throat.

With the spray falling all around us, I let my hands wander behind her, feeling the slick muscles of her back, shoulders, and especially her ass. We found a rhythm together, a pattern of hip thrusts and hand strokes that swept our pleasure-engorged flesh through cycles of slide and stillness. Hot fog rose to fill the glass enclosure as water hissed from the showerhead and lapped its way down our bodies, bound together in gleaming wet passion. Periodically, the flow would wash too much of our foamy lubricant away and Lindsey would scrape more gel from the excess that still clung to my upper chest.

"Mmm," I groaned against her lips as the furnace in my deepest plumbing caught fire. "Mmm, Lindsey ..."

"Mm-hmm." Her tongue flickered into my mouth and she thrust faster against me. "Mmm! Mmmmm-hmm."

The steam around us seemed to thicken and rise almost to scalding heat . I found it harder and harder to keep a steady pace as something spastic and uncontrollable took hold of my spine.

"Hh-mm, Nick -" Lindsey's beat wavered too, groans and moans making her hand falter and then speed up. "Ah ... ah ..."

I came before she did - just barely. The rush fountained up out of me with no warning at all.

"Mmmnnnghhh -"

Her hand squeezed tight around my pulsating cock, and she thrust hard and fast as my cum spurted in throbs and blurts and dwindling splashes between us.

"Uh ... uh-uh ... Nick ... UH!"

And then I felt my orgasm joined by a seesawing gush, me then her then me then her.

"Fuck, Lindsey, ah -"

"Mm, Nnn ..." She hooked her chin over my shoulder and crushed against me, her gripping hand and both our ecstatic eruptions squashed between us. "Uhhhhh ..."

Panting and groaning, we held each other until the reflexive clutch of climax let us go and our bodies could relax.

"Whoo. Ah," she said, putting her forehead to mine.

"Best shower ever," I said, still out of breath.

She laughed and let go of us to free up her hand and loosely encircle me with her arms. Then she kissed me and sighed contentedly and said, "Best first date ever, too. For me, at least."



"Me too."

We watched each other's eyes as the water continued to fall around us.

"I don't want you to go. Can you stay the night?"

"Yes," I said without hesitation. "But you have to promise not to have any more sex with me, because I'll need to get up at the fucking crack of dawn to get back to my place, change, and pick up Sam so he can have his car back."

She looked away and up and to one side, a picture of innocent uncertainty. "Not sure I can promise that ..."

"Grr," I said, squeezing her.

"Oh, okay," she gave in. "But if this is how it works, you're never borrowing Sam's car again. Deal?"


We held each other then, finished washing up, dried off with big, fluffy white towels from Lindsey's linen closet, and ended the night snuggling to sleep in her bed.

* * *

Lindsey turned out to be a surprisingly heavy sleeper, considering how prompt she seemed to be about everything else. When the alarm on my phone went off the next morning, she mumbled and tossed a few times before settling into a restless, cute snore as I threw on my clothes. Once I got dressed, I leaned over her and whispered that I had to go, and she made little kissy movements with her lips until I touched mine to them. Then she said something incoherent that ended with "good day," so I called her a sleepyhead and told her to have a good day too and that I'd see her that night.

"Mmm-hm," she said without ever opening her eyes. "G'night ..."

By the time I picked up Sam at his house, I'd had almost an hour of driving, changing, shaving, cleaning Mister Whiskerdoodle's catbox, and driving again to wake me up. The catbox alone was pretty eye-opening.

So I arrived at Sam's fully alert and aware of where I was, what I was doing, where I'd been the night before - and how I felt.



Surreal, maybe a little high.

A fraction anxious that I'd had a mental break of some kind and everything would crash apart.

But mostly good.

I focused on that to prepare myself for however the conversation might go. We'd spoken very little when he handed the car over to me the day before - he apologized about being untalkative, but said he still had some baby steps to take to get his head around the situation.

This morning, though, it turned out he had more to say.

"So ..." He fastened his seatbelt and I reversed out of his driveway. "I guess I'd be a real jerk if I didn't ask how the date went."

"It went well." I kept my tone easygoing, not wanting to put too much enthusiasm into the statement and end up making him uncomfortable.

"Good," he said. "Glad to hear it."

Heading out of his subdivision, I said, "The exhibit was pretty cool, and we both had a great time talking about it. I did have to rescue her from this vegetable lasagna she ordered, but it was worth the sacrifice."

"Hmm. Bad sign she ordered vegetable lasagna, but I guess a better sign that she didn't want to finish it."

Traffic started to pick up around us. Sam broke a brief silence by saying, "All right, so when you said it went well, do you mean it went well? Or do you mean it went ... you know, well?"

I glanced over and saw a sincere attempt at looking interested in a buddy's masculine conquests.

"Let's just say it went really, really well, and leave it at that," I said. "I know it kind of freaks you out, so I won't give any details except that she's a great kisser."

"Well, uh, that's definitely a mark in her favor." He went quiet again, like he had to work his way up to something. A couple of blocks went by, and then he launched into it. "Look," he said, "I remember playing over at Elise's when we were kids, choking down that terrible lemonade she used to make and running around her yard. And I remember it hit you pretty hard when she died."

I nodded, but didn't say anything.

"I mean, it hit me too," he added quickly. "But my folks had spilled the beans about her to me way before, so I was ... a little weirded out by her even though she'd moved to Maryland by then. And they badmouthed her a lot, especially after she killed herself. On and on about how she always did these selfish things that were against God."

Now I really didn't say anything, because I'd heard my share of those conversations at family gatherings over the years, and I'd always had to bite my tongue against saying anything to one of the grey-haired elders I'd been raised to be respectful of. Being reminded of incidents like that steamed me seriously up.

Sam's voice took on a tone of regret. "I bought into it some too - they were my folks, after all. But the subject always made me uneasy. I couldn't help remembering how much more fun she was to visit than all the churchy aunts and uncles, how she never had anything bad or critical to say to anybody."

"Even when you broke her window with that terrible pass."

"It was an okay pass, you just didn't go up high enough to catch it." We'd had the same argument twenty years earlier as we waited for Elise to come out and yell at us for smashing the glass. But she just brought us the football back, gave us some tips on throwing it, and went back in to sweep her kitchen up. "I think I felt about ten times worse about breaking that window because she didn't yell at us than I would have if she'd wigged out."

"Me too," I said.

He took a deep breath and pushed on. "Anyway, after that call where you said I should broaden my mind, I got a little pissy. I didn't think I'd been nasty to you or to your, uh, date, and I thought it was awfully nervy of you to be lecturing me. And I wanted to bitch to somebody about it. But the first three people I thought of calling all happened to be from the Bible-thumper side of the family. It didn't take more than a second to realize that if I said anything, they'd circle back to Elise and shake their heads over her. And the more I thought about it, the more I picked through the list of people I might tell, the more I realized that the people who were going to take my side were all the people I didn't want to be like. And about then, I realized you were right, and I needed to broaden my mind."

"That's pretty big of you, Sam," I said, meaning it and giving him a glance of respect.

"She was a great person, you know?" He sounded a little choked up.

"Yeah," I agreed. "I remember."

* * *

Thursday night, the appliances came.

And the pre-industrial age AC unit broke.

Lindsey oversaw the installation of the new stove, fridge, and dishwasher while I tore up carpet in the guest bedroom. By the time I finished, the job had turned me into a sweaty mess, while Lindsey just looked a little glowy. My fantasy from the first day I'd met her came back to me - the house without air-conditioning, both of us damp with sweat, the blow-job leading to sex in the same room I'd just denuded of carpeting. But even if I hadn't been wiped out from the heat and exertion, her reaction when she saw me would have kept me from suggesting we give the fantasy a try.

"Whew!" she said, waving a hand. "You need a shower!"

"Yeah," I admitted. "If I was slightly less exhausted, I'd ask if you want to join me for one."

"Ohh," she said. "That sounds nice, and I've been watching muscular delivery men working with tools all evening. But I thought you said last night that you've got a lot of freelance assignments to do."

Crap. Not only had I said that, but tomorrow was Friday, so if I didn't finish my allotment of work, it would be a whole week before I could invoice the client for it.

"You're a lot less fun tonight than you were last night," I grumbled, crossing my arms.

She leaned in and kissed me. "I'll make up for it by being even more fun tomorrow night."

And she did: after Friday's task of reflooring the guest bedroom, we cleaned up in the considerably less spacious shower at my place, had more dick-to-dick whack-off sex before rinsing off, and then went out to this Korean restaurant where a whole section of the menu didn't even have English translations. I'm not a big fan of kim-chee, but whatever we ordered came with about a dozen other tiny appetizers that were amazing - seaweed salad, several different pancake dishes made of unidentifiable vegetables, a highly spiced heap of what tasted like dried anchovies, and some other stuff I wasn't sure I wanted to figure out. Then an amazing seafood soup in a dangerously hot tureen, followed by three smallish entrees that we shared between us. Lindsey went on a couple of times about how much she liked all of colors in Korean food, and she knew what she was talking about - the dishes had the look and presentation of fine art.

"Although art doesn't make me feel like I'm about to explode," I said when I'd reached the absolute maximum capacity of my stomach.

"Yeah, I can never get out of this place before I'm waddling and groaning."

"So do you want to waddle to my place and do your groaning there?"

"Oh god, no." She quickly put a hand over her mouth and another gingerly across her belly. "I would rupture something if we went to bed right now. Plus, they're delivering the rolloff first thing tomorrow morning, so we wouldn't even be able to sleep in."

"I was mostly kidding," I said, puffing my cheeks out to show how bloated I felt.

With the arrival of the rolloff (I would have called it a dumpster) the next morning, we could clear some of the accumulated trash out of the garage - the old cabinet doors, the original kitchen countertops, the sliced up carpet from the front half of the house. A hell of a lot had piled up in three weeks, actually, and we worked like dogs the whole weekend shifting it to the rolloff, stripping the fixtures and tile from the master bathroom, and starting the replacement tile work. The new AC unit wasn't scheduled to come until Monday, so all of this had to get done in sweltering heat. I don't think I drank enough water Saturday, because I ended up with an icepick-through-the-eyes headache by the end of the day.

"Why didn't you say something?" she asked. "I could have kept prying the tile loose while you took a break and got some ibuprofen from home."

"I kept telling myself I would after the next row of tile," I said. Also, we'd been working together on our hands and knees, sometimes shoulder-to-shoulder, sometimes on different sides of the room, and I'd enjoyed being close to her in the first case and checking out her ass and legs in the second case. "It snuck up on me and got really bad before I realized it."

"Well, let's get you home and I'll give you one of my headache-slaying massages."

At my place, I went for the pain reliever in my medicine cabinet while she petted Mister Whiskerdoodle.

"And bring some lotion when you come back," she called to me from the bedroom. I did, and she made me lie down with my shirt off while she worked the hell out of my neck and back with those long, strong fingers of hers, squirting cold lotion down my spine before she got started and then rubbing it in with magnificent pressure.

"Uhhh, where did you learn to do this?" I asked.

"I had a friend in high school with terrible posture. He'd get these tension headaches all the time, and I figured this out as an excuse to get my hands on him."

"Devious," I mumbled into the pillow I had my head leaned against.

"You don't know the half of it," she said. "After a while, I could get him practically comatose face-down on my bed, and then I'd go to massaging him one-handed with the other one stuck down my pants. Closest thing I got to sex until college."

My brain somehow created a picture of beautiful, feminine Lindsey kneeling beside her friend with one hand smearing lotion across his back and the other jammed in her panties. But of course, that wasn't what it would have looked like at all.

"And he never figured out what was up?"

Her hands stopped for a second, then started again. "No, because my dad came in and caught me at it one day and proceeded to beat the crap out of James, who had no clue at all what was going on. No more massages after that - it was weeks before I could even get James to talk to me."

"Wow. That sucks."

I felt her shrug in the movement of her hands.

"Did he ever ... beat you up too?"

"No, but he got into fights with people all the time. I knew what he was capable of from a really young age and made sure I kept out of his way."

"That's good," I said. "I guess something about the way you said you knew he could hit ... I thought you meant you'd been on the receiving end of one of those punches."

"Nope," she said. "He managed to save the physical stuff for people outside the family."

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