A Discovery of Pleasure

This is a story about a man who identifies as straight, growing closer to a transgender woman.

If a man having sex with a transwoman isn't your cup of tea, try one of my other stories. There's also some mild peeing in the story, and one of the characters exhibits but doesn't act on a pee play kink.

I've written this story from the male character's point of view, and I want to thank my husband mark217mark for his invaluable help in my descriptions of male arousal and pleasure.

To my real-life friend Zoey: our hours spent talking, laughing, drinking coffee, and sharing intimate details about our lives and kinks and dreams have meant more to me than you'll ever know. Thank you for your help and suggestions with this story.

As usual for my writing this story takes place in a happy alternate reality where people don't worry about STD's or safe sex.

~~

I sat up, looking around in a brief state of confusion, before realizing where I was and what had happened last night.

"Fuck!" I said out loud, jumping up and moving towards the window.

The driveway was empty and I frantically pressed my face against the glass, trying to see as far down the driveway as I could, but not only was the van not in sight, the snow blowing over the tracks indicated it had been gone for a while.

"Those fuckers," I said, anger rising within me.

We'd all agreed to leave shortly after dawn this morning, and despite my brother teasing us all about being left behind if we didn't set our alarms, I'd had a bit too much to drink last night and had apparently stumbled up to my room without remembering to set mine.

I was at my uncle's remote cabin and had come up here with my brother Colin and a van full of his friends, for Colin's bachelor party. We'd spent the last three days drinking, eating, hiking, and cross-country skiing.

Colin and Ted had picked it as a bachelor party location with my uncle's blessing, and we'd all come up together in Ted's van.

I almost didn't come. I love my brother dearly, and his fiancé Ted is a great guy. But I was the only straight guy in the group and had wondered if that would create a weird dynamic.

"Hell no," Ted had told me, while Colin stood next to him nodding. "It's not like it's going to be three straight days of gay sex. We're just hanging out and getting away from it all for a few days. Food, booze, music, some skiing, some hiking, maybe a peeing for distance contest if we all get drunk enough."

I'd laughed and agreed to come.

I already knew most of the guys they were inviting and had been looking forward to a few days of winter quiet in the woods.

I quickly got dressed, shoving my clothes into my bag and grabbing my phone and charger before running down to the living room, saying a silent prayer that they hadn't really left yet.

However looking out every window downstairs confirmed two things for me.

The first was that the van was gone, and the second was that the weather was turning to shit.

I tried to call my brother, but as I expected there was still no cell signal.

We were a three-hour drive from the nearest town, and at least ninety minutes from a cell phone signal. For three days our phones hadn't been useful for anything but taking pictures and playing music we'd already downloaded.

I went into the kitchen and pulled the old-fashioned landline from its hook on the wall, and dialed Colin's number. It rang several times before it kicked over to his voicemail.

As it did, I suddenly remembered a hazy conversation with Colin about seeing him next weekend.

Had I agreed to stay here for the whole week? Alone?

I hung the phone up and turned back to the cabin's oversized living room.

To call this place a cabin was an understatement. My uncle had designed it himself, and it had every modern convenience, except for easy access to civilization.

In the summer there were always other people around in cabins scattered around the lake, but in the middle of winter it was pretty desolate and lonely.

As I looked around the room though I realized there were far worse places to be stuck.

My uncle had a fully stocked walk-in freezer in the basement, enough canned and dry goods to feed an army for a month, and enough reserve supplies of propane so that anyone here would have heat and hot water for the rest of the winter.

It was then that I noticed something taped to the screen of the giant television. I walked over and found a handwritten note addressed to me.

I tore it off and opened it.

"Dear Ed, we're leaving early to beat the storm. I want to thank you again for agreeing to stay an extra week with Carrie so she can work on her book. I appreciate you being so kind to her. I'll call in a few days and check in on you. Thanks for everything, Colin"

I sat down stupidly on the arm of the couch and tried to remember the details of Colin asking me to stay.

I knew that Carrie was a writer, and needed to do some editing on something she'd written, and I remembered Colin offering her the use of the cabin for an extra week or two.

Had I really offered to stay here?

Was Carrie here too?

Sitting still caused me to realize that my head was pounding, and I was suddenly very aware of the pressure in my bladder. In fact, I had to piss so badly that I suddenly doubted my ability to make it to the bathroom.

I ran up the stairs, pushing open the bathroom door, lifting the toilet seat, and getting my dick out without a second to spare. As I relieved myself, I sighed, trying to remember what I'd said to Colin last night.

"Showing off for me?" Carrie's voice came from the hallway, and I jumped, splashing pee all over the toilet and the floor and my foot as I jerked my head around towards the sound.

"Fuck!" I yelled, turning to correct my aim.

"I'm sorry," Carrie grinned. "I didn't mean to scare you. I thought you saw me standing here."

She was wearing a sweatshirt that was at least two sizes too large for her, and it made her tiny feminine body look even smaller than it really was.

I immediately felt better seeing her, even if she had just seen me piss all over my own foot.

We'd all met up at a hotel back in town the night before we headed up here, and Carrie had joined us early the next morning while we were loading the van. I'd been surprised to see a girl put her luggage into the pile to be loaded, and I was even more surprised by how stunningly attractive she was.

She had a short pixie haircut, with several piercings in each ear and a nose ring.

Her hair was so blonde it was almost white, and she had a few blue highlights threaded in. She was a small girl, and wearing an oversized jacket she looked like an anime character come to life, and her bluish green eyes were absolutely beautiful, and completely mesmerizing.

"Edward, this is Carrie," Colin told me, putting an arm around her shoulder. "Carrie is the one who encouraged me to come out all those years ago. And Carrie, you remember my brother of course."

"The infamous Edward," Carrie laughed. "I absolutely remember him. How have you been Ed?"

"I've been doing well," I answered, looking her up and down. "I'm sorry Carrie, I just can't seem to remember you. Where did we meet?"

"I was Kyle when we met, about eleven years ago," Carrie said. "I hadn't transitioned yet, and I was pretty unsure about who I really was."

"I remember!" I said with a burst of recognition. "You were telling me about a horror screenplay you were trying to write. I'm sorry I didn't know you had transitioned. You must think I'm a pretty big jackass."

"You were very kind then," Carrie said. "And you're fine now. I ran into Colin and Ted a few weeks ago and they invited me along. I haven't exactly kept in touch with everyone."

"Well, it's great to see you again," I said sounding lame in my own ears. "I hope I didn't offend you."

"Not at all," she smiled. "I'm just glad you're here and coming with us."

"Well it's good to be here," I said, throwing my bag into the back of the van. "Can I offer to help you with your bag or is that weird and offensive?"

She pickled her bag up and handed it to me with a grin.

"Help away," she teased. "But it'll take more than that to get me to put out."

"Good thing we have the rest of the weekend then," I laughed, stowing her bag.

I immediately felt like I'd been offensive in flirting with her, but her shy smile derailed that train of thought and I realized that knowing she hadn't been born as a biological female had somehow made her seem even sexier.

Before long the van was loaded, and we were on our way. Colin had driven and I sat in the very back with Carrie and a huge pile of luggage. Ted had offered to sit with her so I could sit up front, but I hadn't objected.

Something about Carrie had really captivated me.

Through my brother I'd met a few people who were in the process of transitioning, and I had long ago become completely comfortable hanging around with all sorts of people who identified in all sorts of ways.

I'd always been attracted to women, without really considering any of the transgender woman I knew in sexual terms. I was comfortable with them all but had never felt enough of a connection to think of them sexually.

Colin told me that his theory was that's what made me so comfortable around his friends and what made them so comfortable around me.

"You're not always acting macho to cover up an insecurity," he'd said. "You know what you're into sexually, and you're not always trying to convert or seduce or put down anyone who's different. Not only is there no sexual tension, but there's no social tension either. You get along with everyone."

I hadn't really given his theory much thought, but now in the backseat of the van with Carrie, I found myself drawn to her in a way that almost felt like a supernatural forcefield had captured me.

Maybe it was just her eyes that made her seem so exotic and erotic. Or maybe it was the fact that she seemed so happy and confident. And without even knowing what her sexual interests were, I realized that she and I were the only two passengers in the van who weren't gay males.

Carrie and I chatted about college, television, and books, and had just started talking about horror movies when Colin announced that we were pulling over for a few minutes.

"What for?" I called up to him.

"Everyone who overloaded on coffee needs to pee," Ted called back. "Including your brother."

Colin pulled over where the dirt road widened, and we all clambered out.

"Fucking cold," Colin said. "Everyone go quick."

There was no traffic and there didn't appear to be anyone around for miles. Most of the group stepped right off the road, but I crossed over behind the van to the other side.

Even though I'd spent lots of time with Colin and Ted and their friends, I'd never engaged in a group trip to the bathroom with them. I was the outsider to the group and didn't want to make anyone uncomfortable.

I unzipped and had just started to pee when to my shock I realized that Carrie was just a few feet away from me.

"I hope you don't mind," she said, lifting her hoodie up and pulling down the front of her pants. "I'm the only girl here, and I don't know some of them all that well. And I have to go too bad to find another spot."

"I don't mind at all," I said, trying to sound neutral.

I was suddenly overcome by a desire to look at her as she peed, but instead I just stared ahead, watching steam rise from my own piss stream. Out of my peripheral vision I noticed a similar steam trail wafting up as Carrie's hot piss hit the snowbank.

It didn't take too many more minutes before we were all squeezing back into the van, and as we started off toward the cabin again, I noticed that Carrie was pressed closer to me than she'd been before we stopped.

"Sorry," she said. "I guess the luggage shifted when we got out."

She tried pushing the stack of bags over, but the warmth coming off her thigh as it pressed against mine didn't bother me a bit.

"Don't worry about it," I said. "Another hour and we'll be there. It's not uncomfortable for me if you can stand it."

"Good," she grinned. "You're warm."

I grinned back and asked her about her favorite movie, trying to stop wondering about her ability to pee standing up. I hadn't been sure exactly how far she had transitioned, or what her plans were, and it didn't feel like we knew each other well enough for me to ask.

But now that I knew she could pee while standing I couldn't stop thinking about her body, and what it might look like naked. Before long I developed a raging hard-on and every time I looked into her eyes it made it worse.

The motion of the van on the dirt road certainly added to my erection, and my mind kept going back to the steam wafting away from her piss.

"What the fuck?" I wondered.

By the time we arrived at the cabin and got out of the van, a few seconds in the icy winter air killed my boner, and we got unloaded and then headed in to find our rooms.

A few of the guys had paired up and two of the single guys had volunteered to sleep on the couches in the living room.

"Ed why don't you take the third-floor room at the front of the house, and you can show Carrie the third-floor room at the back?" Colin suggested. "That way you'll each have some privacy. But you'll have to share a bathroom."

"No big deal," Carrie teased. "We're pee buddies now."

I'd laughed with her, but my mind again flashed to the memory of her peeing next to me, and I felt an almost lustful desire to see her naked.

"What the fuck?" I wondered again.

We got our stuff stowed and Ted's college friend made lunch while everyone explored the mansion-like cabin. We ate as a group, laughing and talking and that afternoon we all went skiing together.

That night we broke out the beer and wine and one way or another the next few days passed by.

I took every opportunity I could to talk to Carrie. When we all bundled up and went hiking through the woods, she and I hiked side by side and I took her hand and helped her over several ditches and downed trees.

Conversationally we were clicking on a level that I'd rarely experienced with anyone else, and even with gloves on each time she took my hand we made eye contact and it felt like sparks were going off.

I was afraid to say anything that make her uncomfortable, so I did my best to keep my sexual attraction to myself, not that I understand at all my desire to explore between her legs.

For three days though she had been constantly in my thoughts, and here I was, standing with my actual dick in my actual hand peeing in front of her.

"I'm sorry," Carrie said again. "I didn't mean to scare you."

"It's okay," I said. "I'm just hungover and didn't expect anyone to be here. I just realized that you and I are the only ones here."

"You mean you didn't know I was going to stay behind with you?" she asked, her eyes wide.

"No, no," I said, flushing the toilet and standing there awkwardly. "I volunteered to stay with you, but I was so hungover I didn't remember that until I was downstairs wondering where everyone was. And then I realized I had to pee, and that's where you came in."

"Let me get something to clean that up," she said.

"Bullshit," I said. "It's my fault and my mess. I'll get a shower and then I'll clean it up."

"You should have just pissed in the shower," she grinned. "It's the best place for a pissy mess because it's so easy to clean up."

I glanced over at the shower, and she suddenly got a weird look on her face.

"I haven't been doing that!" she said in a panicked voice. "I mean I do, at my own place. Not in that shower that you and I have been sharing."

"I'd almost feel better about this mess if you had pissed in there," I laughed. "It would make up for seeing me pee on my own foot."

"Seeing your cock was payment enough," she grinned. "I'm going to make coffee. Do you want some?"

"Fuck yes," I said seriously. "I want coffee. I need coffee. I'd fucking kill for some coffee."

"Get your shower and I'll bring you some," she said.

I turned the water on and wiped and sanitized the floor and toilet, and then stripped and jumped into the hot water. The water hitting my back made me feel better, and I realized that I was actually looking forward to spending the next several days with Carrie.

We had plenty of food and we had wood for the fireplace and propane for the furnace, and a stack of DVDs to watch while I got to know her better.

What more could I ask for?

I turned off the water and pulled the shower curtain back just as Carrie came into the bathroom holding a mug of coffee.

"You take it black right?" she asked with a smile.

"I do," I said, trying to turn my body.

"You don't have to hide from me," she giggled. "I've not only seen everything you could possibly have, but I even have some of it, even if yours is far more attractive."

I immediately thought of her peeing next to me, and I felt myself start to get hard.

"Not now," I thought, trying to think of something else.

But it was no use, my cock was getting erect and there was no way to hide it. She'd see it if I pulled the transparent shower curtain around myself, and she'd see it if I reached for a towel.

"I know," I said lamely. "I just don't want to offend you."

"What could possibly offend me?" she asked.

I turned to face her, my embarrassment making my cock even harder as it stuck out away from my body. Her eyes drifted down and locked in on it, and I felt myself start to blush with shame.

"Sorry," I said softly, reaching for a towel.

"Don't be," she said with a smile. "It happens, and it's hardly an insult. Even if you're thinking of someone else it's still nice to look at."

She handed me the mug of coffee and I took a sip, feeling completely awkward as I stood there rubbing my chest with the towel while she stared at my cock poking through the towel.

"I appreciate that," I said. "I guess now is a good time to confess that the clothes I need to change into are all downstairs by the front door. I packed in a hungover stupor this morning without remembering that I wasn't supposed to leave with everyone else."

"I wondered who left their bag behind," she laughed. "I feel better knowing it's yours. Come on down and get another cup of coffee while you get dressed. Leave your dirty clothes right there and we'll figure out laundry later."

She turned and headed for the stairs, and I paused just a moment. Did she want to see me walking around naked? Or was she really just that comfortable with me?

I finished drying and followed her down the stairs, feeling weird walking around someone else's house naked, but realizing that there wasn't another soul around for miles and miles.

At the bottom of the stairs I set my coffee cup on a shelf and unzipped my bag.

"Here," said Carrie, coming around the corner with the coffeepot and refilling my mug. "If you have any dirty clothes in your bag, I'm going to wash a load. If you're comfortable putting them all in together we can do that."

"That would be great," I said. "I won't have to make these jeans last another day that way."

I pulled out a pair of shorts and stepped into them. Carrie had taken her coffee over by the back window, and I went over and joined her.

"Weather's getting bad," she said. "Makes it kind of nice to be inside."

"When you're right you're right," I said. "I'm trying to remember, you're staying to work on some writing?"

"Yes," she said. "I have some editing to do on a book I've written. And your brother said this place would be perfect if I didn't mind a week of isolation. I wasn't sure about being here alone and he suggested that you'd be open to staying."

"He was right," I said. "I love the winter quiet up here. However long we're here is okay with me."