Weekend Getaway With My Boyfriend and his Sister

“And how long until we reach the cabin?” I asked.

“Another hour or so,” Blair said.

His truck jostled against every stone one the rough weaving road. The forest was admittedly beautiful; trees changing color, a faint snowfall breaking over the distant pines. I bent over from the passenger seat and started to untie my boots.

“What are you doing?” Blair asked.

“I—am going to give you a footjob,” I said, pulling off one boot and working on the other.

“Right now?”

“Yup.”

“Why?”

“Because I am bored,” I said, “and I think it could be fun.” I pulled off my socks then unbuckled. I wiggled my freshly painted light blue toes, and how they matched my finger nails.

Blair looked in the rear view mirror as I leaned over and started to undo his jeans.

“Were still an hour away,” I reassured him. “Worried we will get caught?”

“Last thing I want is my family catching us. I don’t want that to be their first impression of you,” he said.

“Aw,” I swooned, and grabbed his cock. I sucked it once, just to get it wet, then sat back in my seat with my feet in his lap.

I gripped his cock with my toes. I wasn’t sure if the bumpy road was making it better or worse. I felt precum against my sole, so I hoped for the best.

“Do you like it?” I asked.

“It’s definitely—unique. Like a clumsy handjob.”

“But not cum worthy?”

“If I could watch instead of focusing on the road—I could see it happening.”

Even though I was enjoying it, it was rather clumsy, so I stopped. I started to tie up my hair.

“What are you doing now?” Blair asked.

“Blowjob,” I said. I laid on my stomach, my feet scrunched up by the window. Blair moaned faintly as I took him in my mouth. There was something about the shape of his tip that felt great against the inside of my cheek.

He put one hand on the steering wheel, and the other on the back of my head. I knew he liked it when I sucked fast and deep, so I took it slow. We have an hour, anyways, I thought. I used the time to try new techniques and see what he liked most. Which direction I swirled my tongue, how hard I sucked, which way I twisted my lips as I lowered on his shaft, each measured in the soft moans he let out between breaths.

I felt him flex slightly, then hold my head down. I kept my lips firm against his shaft so that none would spill. When the throbbing stopped, I pulled back. I let him see it in my mouth before I swallowed. He seemed to like that, as if it was some sort of accomplishment or sexual accolade.

“So, how much longer?” I asked, slipping on my socks.

“About forty minutes,” he said.

“I only blew you for twenty minutes?”

“That is a lot longer than I’ve ever been blown before,” he said, struggling to hold the wheel and button his pants back up.

“Oh? And how long did the others last?”

“There has only been one other,” he said, “and not that long.” The way he turned away when he said it suggested he didn’t want to talk about it.

I buckled, wiping a bit of stray cum from the corner of my lips. “So, who will be here for the weekend? Is it all your family?”

“No, just a few of them. I think my parents, a cousin possibly, and my sister.”

“The same sister I saw the other day outside your apartment?”

Blair nodded.

“Is she younger or older. I can’t tell.”

“The exact same age. We’re twins. Though she would say she is younger.”

It was strange to think about meeting his parents already. We had only just started dating. And he wasn’t sure how they would react to finding out his girlfriend was a transgirl. A weekend in the woods was worth the risk.

After awhile the trees gave way to a small glade where a handful of humble cabins. The sun had already fallen beneath the mountains, but there was still a faint hue to the sky that indicated it hadn’t set. Snowfall picked up.

Blair parked at the end of a line of cars. I my beanie in the visor mirror.

“You look fine, don’t be nervous,” he said.

“Thanks,” I said.

We were grabbing our bags when I heard the crunch of snow behind us. It was the girl I had seen outside Blair’s apartment. His sister.

“Blair!” she yelped, wrapping her arms around him, and kissing him on the lips.

Woah! I thought.

“Anna,” Blair said, pushing her away, “I know you are trying to embarrass me, stop that. Anna, this is Steph. Steph, Anna.”

“I hope you kiss me like that too,” I joked as she gave me a hug.

“A little later, roomie,” she said.

“Roomie?” I asked, confused.

“No—they aren’t really doing this, are they?” said Blair.

“They are,” Anna said.

“Who?” I asked.

Blair sighed. “My parents had a rule when we were younger. Boys in one cabin, girls in another. I had thought that they were past that—I’ll talk to them.”

“I’m guessing that me being trans wouldn’t help the situation?” I guessed.

“Probably not,” Blair whispered.

“I don’t mind staying with Anna,” I said. She smiled. “It is just for the night, anyways, and it will give me time to get to know her.”

“That is what I am afraid of,” Blair whispered. Anna punched his arm.

“Don’t listen to him. He thinks just because he is older, he is somehow wiser,” Anna said. “You two are just in time for dessert.”

“I already had mine,” I whispered to Blair. He blushed and shook his head.

Blair introduced me to the few that had made it to the cabins. His parents were kind enough, if not curious, his dad going so far to ask if I was pre or post op. But it was pleasant. We had some pie, played some games, and shared conversations until all light faded from the windows and piles of snow crept at the edges.

There had been an attempt by Blair to convince his parents to let us stay together, but they had denied it. I simply smiled and shrugged, it wasn’t that big of a deal.

“Follow me, Steph,” Anna said, treading carefully down the snow covered steps. “Our cabin is over here.” She shot a knowing glance at Blair.

The cabin was a lot smaller than I had expected. And I mean, a lot smaller. It was basically just a room with a single queen sized bed, a wood stove, and a bathroom set off to a corner.

“Do you prefer left or right side of the bed?” Anna asked.

“We’re sleeping together?” I asked, setting down my bag.

“If you pour me some wine and call me cute,” Anna joked. “Is that alright? If not, I don’t mind sleeping on the floor.”

“Oh no! It’s alright.”

“You sure? If you change your mind, don’t hesitate to tell me,” Anna said. She started to undress. She had long blonde hair, and the same lanky build that Blair had. “I was going to take a quick shower before what little hot water is taken by Blair.”

“Alright,” I said. I looked at the wood stove. “Hot water but no heater?”

“There is a hot water heater in my parent’s cabin that is shared with the others,” Anna said. “Terrible design. Makes for great arguments though. You want to go first?”

“You don’t mind?” I asked.

“Nah, go for it. I’ll get the stove going.”

“I’ll be quick, I promise,” I said. I stepped into the bathroom, stripped, and started the shower. I wouldn’t exactly call the water warm, but it wasn’t cold. Something about it felt crisp and abrasive against my skin. By the time I turned the water off and opened the curtain, it dawned on me.

“Hey, Anna,” I said, “you don’t happen to have a towel, do you?”

“Oh, shit,” Anna laughed. There was a pause. “Can I come in?”

“Yeah,” I said, hiding behind the curtain.

Anna walked in wearing nothing but her bra and panties. “I would go get some, but I already undressed. We can always—air dry? In front of the stove?”

I laughed.

“Yeah, that will work! Here, switch me,” she said, “I’ll close my eyes. Go stand in front of the fire, you should be dry by the time I’m done, and then I’ll do the same.”

I was so nervous I didn’t stop to think about it, stepping out of the shower and walking naked into the main room while Anna closed the door behind her. I stood there, shivering in front of the fire, and not getting much dryer.

The shower shut off. “Are you dry, yet?” Anna asked.

Water droplets were still clinging to my boobs and ass. “Not really.”

“Damn. Hmm. Oh, open my bag. You should see a pair of flannel pajamas. You can use the top to dry yourself if you could bring me the bottom.”

“But don’t you want to wear those?”

“Nah, I’ll just sleep in my underwear.”

I dried myself off best I could, then brought the bottom to the door for her. When she opened the door she glanced at my naked body.

“Woah!” Anna said, then closed the door.

I grabbed a fresh bra and thong from my bad and put them on, then slipped into the oversized shirt I slept in.

“You know,” Anna said, “we probably could have just texted Blair to bring us towels. But then again, I wouldn’t have been able to see each other naked.”

“I think you only saw me,” I said.

Anna walked out completely nude. I jumped.

“Think again,” she said, digging through her bag and putting on underwear. She sat back on the bed and stretched.

I sat next to her with a bottle of lotion, rubbing some on my legs. I offered it in her direction, and she did the same. Anna was clearly a joker and revelled on a good tease. I liked her.

“So, you are in love with my brother?” she asked.

“Madly,” I said dramatically, “I even got a tattoo of his name across my lower back.”

“Really?” Anna asked.

“No,” I said. “I like him, though, yeah.”

“Wine?” she asked, pulling a bottle from her bag.

“Oh, you were serious about the wine,” I said.

She popped the cork and took a swig, then handed it to me. “I never joke about wine.”

I swallowed a gulp. It wasn’t bad, a little acidic but strong. I handed it back to her, then reached for a pair of socks.

“You wear socks when you sleep?” Anna asked.

“Always. The only time I don’t wear sock is when I shower and when—” I paused.

“And when you, what? Fuck?” Anna guessed, swigging at the wine.

I grabbed the bottle and did the same. “Yup.”

“And have you fucked my brother?” she asked.

I almost spit out the wine.

“You have! Steph! How was it?”

“I am not going to share that with you,” I blushed.

“Why not? He is my twin. I should know.”

I said nothing and took another drink.

“At least tell me this. When you were making out, did he bite and pull on your lower lip?”

I nodded.

Anna grinned. “I taught him that. I knew you’d like it.”

“Wait? What?” I asked. “You mean, like you told him to do that.”

Anna took a long swig of the wine before responding. “No—I, look we have a complicated relationship.”

“A relationship beyond being twins?” I asked. “I mean, don’t get me wrong, I love a good game of thrones romance.”

“It isn’t romance,” Anna said, “just—sex.”

I squinted at her. She must be lying, right?

“I don’t believe you,” I said, drinking. “Blair told me you like a good joke. Well ha! You got me! I almost believed you for a second.”

“Kiss me,” Anna said.

“What?”

“I’ll prove it. I’ll show you how Blair kisses,” Anna said. She sat forward on the bed.

“I think you’ve had a little too much wine,” I said.

Anna smiled a devious smile. “I guess you’ll never know then.”

“Okay, okay,” I said as I set down the bottle on the side table. “I’ll bite. Well, you will be the one biting—to show you really know what Blair does.”

“Here, lay back against the bed,” Anna said. She kissed me. Gentle, then firm. And then she did it. The same biting move that I’ve only ever known Blair to do.

“What, the fuck,” I said as she pulled away.

“Awesome, right,” Anna said.

“No, I mean you have kissed him! Your own twin?”

“Look, its weird. You got me. But its like I said, its just sex. We aren’t looking to get married or anything. Every so often we just like to—fool around is all.”

I blinked a few times, blankly. “So, that time you were at his apartment before our second date? I thought I heard a kiss from the hallway?”

“Yup!” Anna said. “I was prepping him for you. You’re welcome, by the way.”

“I don’t know what to say,” I said. “Honestly, I am a little confused now.”

“Yeah, it is a lot to take in.”

“No, that’s not it,” I said. “I think—I think you and I need to fuck.”

“What? Steph, you’re the one drinking too much. That’s crazy! But, walk me through it first.”

“You fucked Blair without me, I say we fuck each other without Blair,” I said. My thinking wasn’t quite the straightest at this point, but the logic seemed to flow at the time. I kissed her before she could say anything, and she kissed back.

Before I knew it, Anna had taken off my shirt and was unbuttoning my bra. I did the same to her, pushing our boobs together as we kissed. It was different than what I was used to, but not bad. Anna pushed off and put her head toward the end of the bed.

She pulled off my socks. I could feel her hot breath on the soles of my feet. Then she started to lick. I grabbed her ankle and started to suck on her toes at the same time. She found it ticklish, laughing and then working her way up my leg.

I was breathing hard by the time she fingered at my thong and tossed it to the side of the bed. She grabbed my transcock. “I’ll show you something Blair likes,” Anna said. She gripped my small sack, hard, and forced my transcock down. Then she licked from the bottom of my shaft, across the tip, and over the top. She did it repeatedly.

Her ears were cold against the inside of my thighs as she sucked me. I liked the feel of my bare feet against her skin. She took me deep in her mouth until my transcock completely disappeared down her throat and I moaned.

I grabbed her shoulders and lifted her up. I pushed her face down, lifting her ass into the air and stripping of her panties. I spread her cheeks and licked at the pink button that was her tight asshole. She quaked with a moan as I pushed my tongue inside.

Anna held tightly to the pillow as I ate her ass. I would have preferred to suck a dick, but this was still satisfying.

“Fuck me,” Anna said, “fuck my ass.”

I got on my knees behind her, softly pushing my transcock into her ass. I had been the one getting fucked so often that I forgot just how good it felt to fuck someone. I pushed in as much as I could, my transcock not as hard as I wanted it to be.

Anna held her cheeks as I slid in and out of her ass. Then I fell back on the bed.

“Did you cum?” she asked.

“No,” I said panting, “it is—harder for me to cum. I usually need a cock in my ass.”

“I understand that,” she said and grinned. “Text Blair, tell him to join us.”

Blair, I thought. Fuck, I just fucked his sister. But, then again, he is also fucking his sister. This is complicated. “I don’t know,” I said.

“Too late,” Anna said leaning over the bed, “already texted him.”

I panicked. “What did you say?”

“I told him that I couldn’t get you to cum,” she said.

“You didn’t.”

“And that we would both take what he has to offer,” Anna continued. “Why are you blushing so bright?”

“Oh, I don’t know,” I said, “it could have to do with my boyfriend is fucking with his twin. Or that I fucked his twin.”

A knock echoed from the door.

“Come in!” Anna said.

“Anna,” Blair said, “you said that, um, Steph needed something?”

Anna pressed our naked bodies together on the bed. “That’s right,” she said.

“Anna! Steph? What the fuck!”

“What the fuck is right!” I said. “Why didn’t you tell me that you were having sex with Anna?”

“Well, it never really came up naturally,” he started, “but what are you two doing?”

“Waiting for you,” Anna said. She got up and got on her knees in front of him. He laughed nervously as she moved for his zipper. He looked at me.

“You heard her,” I said.

Blair relaxed, a little, letting Anna unzip his pants and let them fall to the ground. I watched as she started to suck his cock. I felt a little bit confused. A bit jealous. Anna spun him and pushed him to lay on the bed. I stripped the rest of his cloths off and kissed him.

Out of the corner of my eye I could see Anna blowing him from the end of the bed. I could do better, I thought. I spun around and straddled my legs over Blair so that I was face to face with his cock. I could feel him reach up and grip my cheeks, leaning forward to eat my ass.

Anna and I shared his cock. I would suck it, then she would take it out of my mouth and put it in hers. She would grip his balls, and then I would gag as I deepthroated him. Blair put my transcock in his mouth and started sucking.

Anna climbed up the bed and took my spot, straddling Blair herself. I claimed his cock for myself, sitting so that I was facing Anna. Blair shoved his cock into my ass. I spread my cheeks and sat back, pushing him deep inside me.

I started to ride Blair while he ate out Anna. Anna and I kissed between moans. And then, between the heavy breaths, I heard Blair’s breathing starting to still. Knowing what was about to happen, I pulled his cock out of my ass and pushed it into my mouth.

I held the cum in my mouth as Blair sat up. I looked at Anna, and then started to kiss her. I pushed his cum into her mouth with my tongue, and then she let it drip back into mine. We kept exchanging the cum back and forth until it had all been swallowed.

I slid to one side of Blair, resting my hand on his chest. Anna fell to the other side, also resting a hand over his chest. Anna closed her eyes and sighed pleasantly. There were so many questions I had for Blair, but be it the wine or the fucking, I was beat.

The last thing I heard was the soft snoring of Anna, resting her head on his shoulder, just before I fell asleep.