Dessert Day

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I was sleeping peacefully, having little to no dreams. There was a small warmth of a body beside me, it was seemingly perfect until I was woken by a pillow to the face. I groaned and held a hand over my face, only to be hit again.
"Gabrieeeeeeeel," I groaned and I heard him giggle.
"Your sleeping looked so peaceful and we have a whole day off so uppy uppy my cute puppy," Gabriel said and leaned down. I smiled and expected a kiss, instead I got wacked in the face with a pillow.
"Oh you ass," I laughed and sat up. I grabbed a pillow and smacked him with it hard, making a loud sound followed by a small 'oof' from Gabriel. He hit me back and we laughed, hitting each other over and over. Eventually we started moving to dodge each hit before hitting back, I'm not sure how long we were fighting but it was firmly interrupted by a harsh knock on the door.
"Some of us use our day off to catch some sleep shut up!" Dean yelled and I giggled, looking at Gabriel. I noticed he had put his clothes on for today but his hair was messy from our pillow fight, I'm sure mine was worse. I was wearing boxers and a thin t shirt that was rucked up from being smacked with a pillow.
"So you're gonna have to get dressed," Gabriel said and put his hands under my shirt.
"Can I try to squeeze into one of yours?" I asked and pouted, he laughed and raised an eyebrow.
"Try yes," Gabriel laughed and I picked one of his shirts up off the floor. I brought it to my nose and he laughed, I smiled and buried my face into the fabric.
"Smell so damn good," I mumbled and set it down in front of me. I pulled my shirt off and attempted to pull the red shirt on, I struggled a bit and I knew I had stretched it out.
"Oh shit," I laughed while I was halfway through putting it on. Gabriel laughed and helped me, guiding my arms through while stretching it out. I finally got it on and it definitely didn't fit, I had stretched it across the shoulders and chest. Gabriel smiled and adjusted the shirt, if I raised my arms it was going to come up almost all the way.
"I like it," Gabriel smiled and I laughed.
"What're we doing today?" I asked and Gabriel shrugged, he pulled the shirt down again.
"We should bake Sammy!" Gabriel beamed.
"Sure," I laughed, "we could run to the store and get some stuff."
"Let's make a pie, a cake, and brownies." Gabriel declared and I laughed, he grabbed my hand and kissed it before cuddling my hand.
"Anything to make you smile dear," I joked and he rolled his eyes, "let's start now it's almost noon."
"Right," Gabriel smiled. I stood up and pulled a pair of jeans on, walking to the kitchen with Gabriel.
"So I'm gonna run to the store and get a few more things okay?" I said and he smiled, nodding.
"I'll work with what's here for now," Gabriel said and I nodded. I walked over to him and pecked his lips gently, I tucked some of his hair behind his ear and kissed his cheek.
"Love you be right back," I waved and walked out.
"Love you too," Gabriel called after me as I left.
...
Shopping was easy, I found all the ingredients to make everything from scratch.
"Are you baking, oh my that's just beautiful people really don't bake much anymore." The cashier cooed at me and I smiled, nodding at her comment.
"Is it a family gathering?" She asked, just keeping pleasant conversation.
"Yeah me and my partner are baking for our brothers," I answered and she smiled.
"Partner?" She laughed, "don't worry about it if it's a male dear."
"Yeah?" I huffed a laugh and she smiled.
"Well if you have a boyfriend to get home to I won't keep him waiting," she smirked and I waved her off after grabbing my things.
...
I walked into the kitchen, Gabriel was on a step stool reaching for something and I couldn't control my laughter. I looked closer at his shirt riding up, oh my dear Chuck.
"Are you wearing a g-string Mr. Too-Short-To-Reach-The-Cabinet?" I laughed before whistling and wriggling my finger under one of the strings, pulling it back and letting it slap back against his skin.
"Ouch," Gabriel winced and swatted at me, "try to be sexy for you and you hurt me."
"I learned from the best," I said and set the bags down, "what're you reaching for exactly?"
"There's chocolate I made you hide up there for me," Gabriel whined and I laughed. I stepped over and reached up, half of my shirt coming up with me. I grabbed it and handed to him, he smiled and stepped off the stool.
"Pans are allll the way down here," Gabriel drew out and bent over dramatically so I could fully admire the underwear he was wearing.
"Mhm," I nodded and felt my dick jump slightly. Not now. Gabriel smirked and placed the pans on the counter, looking me up and down. He put his palm against my chest which was overly exposed by how tight the shirt was, he smirked lazily and moved his hand around.
"You look so nice today," he whispered, "you look so nice everyday but today..." Gabriel walked around me and I raised an eyebrow, he stopped behind me and wrapped his arms around my waist. He laid his head on my back and he sighed contently.
"I love you," Gabriel mumbled against my shirt.
"You're adorable," I laughed and he tightened his grip, "I love you too honey."
"What you wanna make first? I put pie crust in the fridge already," Gabriel said.
"Let's do pie first," I suggested, "them brownies, cake last."
"Gotcha," Gabriel smiled, "I'll see what I can do."
...
"Sam it's a mess," Gabriel whined as I swiped more chocolate frosting across his face only to lick it off.
"But it tastes so much better off you," I smirked and took his hand. His fingers were covered in chocolate and crumbs, I took one into my mouth and sucked it clean. I did all his other fingers the same way, one at a time pulling off with a pop each time.
"Quite a show," Gabriel breathed out and I chuckled. I pushed him toward a counter and put my arms on either side of him to trap him, I met his lips but kissed him teasingly. Rubbing our lips together and swiping my tongue across his lower lip but not opening my mouth.
"Sweetheart pie's gonna burn," Gabriel pulled away and put a hand in my hair. He tugged me back down and kissed me hard, I moaned in surprise before he let me go.
"Let me get it out and we'll play with the whipped cream, yes?" Gabriel waggled his eyebrows and I smirked.
"And the chocolate?" I asked and he nodded, walking to the oven with a sway of his hips. There were footsteps toward the room as Gabriel pulled out a pie, brownies, and a cake of the oven.
"Woah that's a pie," Dean smiled eagerly.
"Just give it a minute to cool off," Gabriel smiled and bent down far to reach something in the bottom. I rushed behind him so Dean didn't get a great view of Gabriel's whale tail.
"Who's shirt?" Dean pointed and laughed, I crossed my arms and bitchfaced him.
"Guess," I rolled my eyes and Dean laughed.
"Definitely not your size," Dean commented, "I can see everything I really wasn't too interested in seeing."
"Shut up," I laughed and tucked some hair behind my ear.
"How about you get all the whipped and ice creams out of the fridge handsome?" Gabriel called and I walked to the fridge, pulling them both out and setting them on the table with an ice cream scoop I bought today. Dean and Gabriel walked out, setting everything on the table. I smiled and Castiel walked into the room, his walking was a little off.
"How'd your guy's day go? Been gone all day," I asked and Dean looked up at Castiel like they could communicate through glares. Castiel blushed and sat down, being rather slow about it.
"Fun," Castiel smiled, "we had a lot of fun today. Tried some new things."
"We definitely got our entertainment for the day," Dean coughed and I raised a suspicious eyebrow.
"I'm totally reading Cas' mind and uh- you want healed? I've been there too buddy," Gabriel snorted laughter and Castiel turned red.
"Usually it's Sam though in case you were curious," Gabriel winked at me. I looked at him confused before it clicked, I laughed and held my stomach as I did.
"Oh don't be mean to them," I said and both Castiel and Dean remaining silent.
"Everyone has their first time just don't hurt the ex-angel," Gabriel smiled.
"Alright enough," Dean muttered.
"We've all been there except for Dean," I asked more than stated.
"Sam," Dean banged the table, "no Cas hasn't put his dick in my ass."
"Relax," I said and raised my hand in surrender, "me and Gabriel are very experienced you could've asked us and we could've helped avoid hurting Cas as much."
"Enough," Dean said.
"Dean their advice could be constructive," Castiel said and Dean paled.
"No way I'm getting sex advice from my younger brother and his boyfriend," Dean yelled.
"We could talk about it while eating," Gabriel suggested.
"Fine sure because my life couldn't get any fucking weirder," Dean smacked the tsble in defeat. We all sat down, getting our choice desserts knowing we hadn't eaten any real dinner food.
"So what are the issues," Gabriel asked politely.
"The pain," Castiel said, "and I'm not sure I like laying there and letting it happen. I want to do something."
"What kind of lube are you using? What's your position? Are you using a condom?" I asked and Dean shook his head.
"Water based," Dean grumbled.
"Not thick enough," Gabriel shook his head, "dries up too fast that could be the cause of your pain."
"We began on my back but that hurt so I laid on my stomach," Castiel said.
"Good," I praised, "but if you're feeling it try letting Dean lay on his back while you 'do the work'. Once you're comfortable obviously."
"You should be using a condom and just remember it hurts more in the beginning since the head is the widest part," Gabriel said and I nodded.
"After so long it gets easier," I said, "plus you get better at stretching and not clenching which helps. Eventually you'll be in every position all the damn time." I glared at Gabriel who smirked slightly.
"You'll also figure out top and bottom if youh haven't already," Gabriel said, "or you'll be versatile like yours truly." Gabriel motioned to me and Dean gagged.
"No advice and YOUR sex life is two different things," Dean covered his ears.
"All advice is based on experience," Gabriel said.
"Of course it is but what you guys do is not for me," Dean said.
"Fine but it's so much fun to discuss at the table," Gabriel groaned sarcastically, "we've definitely discussed it at the table before."
"ON the table dear," I smirked and Gabriel laughed. Dean made a sick face before I turned to Castiel, who seemed to be absorbed into his food.
"I'm finished thanks Gabe," Dean said and abruptly left the table.
"He's worried," Castiel mumbled, "about hurting me it's... overly upset him."
"As per usual?" I said sarcastically and Gabriel nodded in agreement.
"Anytime you get hurt Dean over reacts," Gabriel said, "was it so painful that you couldn't enjoy it Cas?"
"No it was actually quite enjoyable and bonding," Castiel said quietly, "gentle and loving. I tried to explain that to him because he felt bad, I still... finished and stuff."
"Yeah he's just very overly caring when it comes to you," I explained.
"Can I ask about... your first time?" Castiel was nervous, a little awkward with his questioning.
"Um," Gabriel hummed, "we did it with all precautions beforehand."
"I laid on my stomach, we used the thicker lube, Gabriel bottomed out very slowly being sure to stop when it hurt, he let me adjust to the size, and then you move slow. It's like having your guts turned inside out but it feels good going right back in."
"That is similar to me and Dean's time," Castiel said, "besides using the wrong lube and not using a condom."
"Well you guys can try again as long as you're quiet about it," I grimaced and Gabriel laughed.
"Yeah I'm gonna go try to talk to Dean," Castiel said and walked off. Gabriel sighed and turned to me, smirking a bit.
"So we could totally play with the rest of this dessert," I suggested and ran my finger over the cake. I licked the frosting off my finger and Gabriel growled quietly, I chuckled and he walked over to me.
"So we're going to remove the shirt before we start because it'll be impossible to remove gracefully," Gabriel said and ripped the shirt down the middle. He tossed it to the side casually, smiling up at me.
"You're underwear can't be comfortable," I mumbled and he shrugged.
"Not terrible," Gabriel smiled, "I've enjoyed having them on."
"I'm sure you have," I laughed and kissed him lustfully. I took off his shirt that was covered in chocolate and flour, I unbuttoned his pants and pulled them down a little bit. I reached around him to grab the can that was sitting much too innocently on the table, I removed my mouth from his dragging his lip out with me. He hummed and smiled lazily, I took the can and held it to his lips. I put some in his mouth before putting it all over his chest, I bent down to lick it all off his skin. It melted slightly so I tried to catch it all with my tongue, I pushed Gabriel further onto the table so he was laying down on the table.
"I'm going to cover you in cake and eat it off you okay?" I whispered and leaned down to nibble at his ear, he moaned through closed lips and arched his back a little. I pulled his pants all the way off, I grabbed a messy handful of cake and smeared if across his hips and lower stomach. I started to lick and eat it off of him, licking around the small underwear that were not concealing his excitement whatsoever. After I finished, Gabriel was left a groaning and wriggling mess.
"Hand me that can dear," I said and he handed me the can of whipped cream. I carefully pulled his g-string off and put whipped cream down his dick in a stripe, he gasped as I licked it off slowly.
"Sam please," Gabriel whined and bucked his hips. I chuckled again before taking his length in my mouth, sucking hard as I slid to the bottom and felt him hit the back of my throat. Gabriel hissed and arched his back, his hand tangling in my hair. There was a few crumbs of cake that were caught in his hair that I gladly let cling to my lips.
"Sam you sure you- fuck," Gabriel moaned and I hummed on his at the praise. This was enough to make him cum, surprising me as I choked pulling off of him. It went down my chin and face as I attempted to swallow it, he smirked and wiped the excess off my chin and lower lip. He placed his finger against my lower lip so I could suck the cum from his fingers, he nodded and smiled sleepily at the sight.
"So," Gabriel said and flipped us over making me yelp, "my turn." I laid back relaxed and Gabriel muttered 'good boy'. He pulled my pants off, which was the most amazing feeling of relief in the world. Gabriel pulled my boxers off and licked a stripe up my dick, making me shudder.
"Sh," Gabriel shushed and looked around, "shit I'll be right back hang in there." Gabriel pulled his pants on, no underwear which seemed horrific. Leaving me there felt like forever, my dick twitching in anticipation and jumping when I heard Gabriel's footsteps. He entered and pulled his pants back off, huffing at the efforts he just exerted. He lubed up his fingers, pushing one into me teasingly.
"Seriously," I groaned and he laughed.
"You can have more if you just shush," Gabriel warned and I huffed shakily. He pushed another finger into me and moved them, thrusting and crooking them until he hit a bundle of nerves causing me to cry out.
"Fffffffffuck Gabe," I moaned. Gabriel pushed a third finger in, making me gasp at the sudden change. He wrapped another hand around my dick, pumping in time with the thrusting of his fingers.
"Shit," I arched as he hit my prostate again, "I'm almost-" And with that came the hot white ribbons of cum, shooting out onto my stomach as Gabriel watched hungrily. He smiled and licked it up as I caught my breath, I blinked at him and he kissed me more gentle now. I gripped the golden curls on his head and when he pulled away I grinned, he laughed a little in response.
"I love you," I chuckled.
"I love you too," Gabriel responded, "we need a shower because there's chocolate it very uncomfortable places."
"Agreed," I smiled and he pecked my nose.

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