The First Time in a Long Time #2

I woke up the next morning, Jack still lying on top of me. He was still asleep, his messy, beautiful hair splayed out across my chest. I had forgotten he wore a dress on our date, and it was still on, though one of the straps was off his shoulder, which was so sexy for some reason.

Not wanting to wake him, I laid still, only turning my head to get a look at his bedroom. It was decorated very differently from the rest of his place: he had framed posters of various artists and musicians, some of which I had never heard of, but the ones I recognized were of varying genres. We had talked about our music tastes, and his were definitely more eclectic than mine. He also had a decent collection of vinyl records, and what looked like a vintage player too. He was a bit of a hipster, but I was totally into it.

I continued scanning the room when I noticed an acoustic guitar in the corner. He hadn't told me that he played. I wondered why he neglected to mention that, but I could ask when he woke up.

Speaking of which, I had to piss really bad, so I gently tried rolling him off of me, but I ended up waking him anyways.

"Hey, sorry I just needed to use your bathroom," I apologized.

"Mmm... izz okay.." he replied, sleepily. He rolled over to look at me, slowly opening his eyes. We smiled as we made eye contact.

"You were amazing last night." I said as I leaned in for a kiss.

"Me? You were an animal, I haven't been fucked so good in a long time, I've definitely never cum twice so quickly before."

I walked the few feet to his bathroom and peed for a solid minute. "That was really hot, by the way. I don't think I've ever seen a guy come twice in one night either."

I finished up and got back into bed. I gazed at Jack for a moment, and reflexively said, "God, you're beautiful."

He blushed, playfully punching my shoulder. "You're just a big flatterer, eventually you'll get tired of me."

I made a mock surprised face. "Who, me? Never!"

"Yeah huh!" He retorted. "Pretty soon you're gonna notice how fat I am!"

"Nuh uh! There isn't an ounce of fat on you!"

"Oh yeah? Fine, I'll prove it!" He stood up defiantly, standing a bit away from the edge of the bed. He started pulling the other strap off of his dress when I interjected.

"Slowly..." I said, my mouth slightly open as I licked my suddenly dry lips.

He grinned knowingly, as he bit his lip in the insanely sexy way he did, and began a striptease. He lowered the shoulder strap, slowly pulling the top down as he swayed his hips, working it down until it fell completely off.

"See?" He said softly. "I'm disgusting, right?"

My eyes devoured his perfect figure. I started with his chiseled, yet feminine face, slowly working my way down his toned chest, his perfect pink nipples, his flat stomach, finally coming to rest on his member. He wasn't hard, but he was definitely a shower. If I had to guess, I'd say he was about 7 inches total, and VERY thick. My lips got even dryer as my mouth started to water.

As if sensing my growing arousal, he slowly walked back to the bed and climbed on top of me, straddling my waist. He leaned down and we shared a passionate kiss as our cocks began to harden in response. I reached down and began lightly teasing him, and he reciprocated. We stayed there for a while, just gazing into each other's eyes as we moaned softly, our hot breath on each other's lips.

I could feel myself getting close, so I gripped him a little firmer and pumped a little faster, wanting to get him there too. He did the same for me, and now it seemed we were in a race to finish the other first. Despite my efforts, he got the best of me as rope after rope erupted from my dick, covering his hand and my stomach. He came soon after.

He plopped down next to me on the bed, and in between heavy breaths, he declared: "I win."

I patted him on the thigh and gasped, "Good game."

"I'm starving!" He said after we rested a bit. "Know any good places around here?"

"Yeah, there's a nice little diner not too far from here, we can get a nice breakfast," I replied.

"Mmm, I love breakfast. Give me a stack of pancakes, eggs and bacon, and I'm good." Jack made an exaggerated drooling face.

"An excellent choice, I think I'll get some biscuits and gravy," I said.

"Oh man, I want that too! You better share!"

We got up and hopped in the shower. We started off innocently enough, but things escalated quickly. Before we went too far, we both agreed that if we went again, we wouldn't have the strength to leave the house and would probably die of starvation. So, we finished up, I put my clothes back on, and he dressed in a Joy Division tee and jeans, and we headed out.

At the diner, we ordered our respective meals from a waitress with a distinct Southern accent, and before long we were chowing down. His pancakes were really something, and he declared to the waitress that their biscuits were "the best biscuits this side of the Mississippi." She laughed, called him "darling" and went on to help another table.

Just then, a Johnny Cash song came on the diners jukebox, and Jack began to sing along. He mimed the guitar part, which reminded me of the one I saw in his room. I figured I would ask.

"Hey, I saw a guitar in your room. You never told me you played!"

He stopped singing and looked away in embarrassment. "Oh, yeah that... I play a little I guess..."

"Oh, I'm sorry I didn't mean to embarrass you. I think it's really cool! I played some piano in school, but I doubt I can read sheet music anymore. I might remember a couple classic rock tunes, but I'm pretty rusty."

"Oh yeah? That's awesome!" He replied. "Sorry, I'm just really self conscious about it. It was sort of a dream when I was younger, but it didn't really pan out. I kinda get stage fright."

"I get it, I hated recitals. I didn't stick with it too long, I had more fun just playing on my keyboard in my room. Maybe when we get back to your place you could play me something?"

"Oh, back to my place?" He asked suggestively.

"I just meant maybe we could hang out, or something... Unless you have another date tonight?"

"Oh yeah, my husband is coming back tonight, so you'll have to clear out," he said in a faux serious tone.

"Guess so. Well, it was nice seeing you. You got the bill?" I asked as I started to get up.

"Jerk!" He exclaimed as he laughed. I grinned as I sat back down.

"Maybe I'll play something for you, after you do something for me."

"Oh yeah? What's that?" I asked, intrigued.

"I want to see the city. I've only been here a couple weeks, but it was all spent moving and figuring out work. You seem to know all the good places, so..."

"It would be my pleasure." I responded.

The waitress came back with our check, Jack treated this time. We decided the best place to start was the heart of downtown, and set off on our adventure.

I showed him the historical section of town, full of beautiful, old buildings. We visited a small art museum, a music store (Jack picked up a couple new records) grabbed some lunch, and finally ended up at the movie theater. They were playing some trashy old horror flick that we had never seen. We had a good time making fun of the terrible acting and special effects, plus the theater was empty, so no one was there to complain.

After the film, we decided it was time to head back. We ordered some takeout and got back to his apartment. He put on one of his new records while he ate. My music taste is pretty basic, so naturally, I had never heard of the artist, but the music was great. He spent dinner explaining the history of the band, the individual musician's backgrounds, and other bands that were related. I was only half listening, more impressed at his extensive knowledge, and enamored by his passion.

After dinner, he told me to sit on the couch while he went to get something. After a minute, he came back with his guitar.

"A promise is a promise." He said.

I sat in eager anticipation for him to start. I could tell he was a little nervous.

"It's okay, you don't have to if you don't want to," I reassured him.

"No, it's okay. Just been a while." He took a couple deep breaths, closed his eyes, and started lightly strumming the strings.

I didn't recognize the song at first, but once he started singing I recognized the tune. He serenaded me with an acoustic rendition of Chappell Roan's "Pink Pony Club." I was in awe of his beautiful voice, the skill and passion he played with.

When he finished, he opened one eye and looked over at me. "So...?"

"That was amazing," I replied. "I've heard it on the radio a hundred times, but I had no idea it could sound like that. You're amazing, Jack."

"Really?" He opened both eyes, beaming at me. "I was afraid I was going to forget all the chords, or my voice was going to crack!"

"No, it was wonderful. You're..." He stopped me with a kiss.

"Thank you, George. I never thought I would play in front of someone ever again, but you.."

I kissed him back, this time more deeply. He gently set his guitar to the side and slid up next to me on the couch.

Before I knew it, we were both naked again, our erections brushing up against each other as he straddled my waist, grinding his hips against mine.

"I want you now..." He whispered in my ear.

"I'll get a condom," I said as I began to sit up.

"No... not this time." He pushed me back down. "I want to feel you. All of you."

He began kissing my neck, down my chest, stomach, and finally planted a kiss on the tip of my penis. He slowly took the head between his lips, working his tongue around as he slid his mouth lower. He began loudly sucking me, slathering my aching cock with his saliva. I was about to blow when he stopped. He gripped the base of my dick firmly as he lined me up with his ass, and began to slowly sink down.

The feeling was incredible. The warmth and tightness of his insides made my legs go numb. Once I was fully inside, he began slowly rocking his hips, grinding against my pelvis. The feeling was exquisite. I grabbed onto his hips and began to grind back. No thrusting, just relishing our joining. His cock pointed directly at me, a steady stream of precum flowing from the tip. I reached out, using my thumb to slather it around, lubing it as I worked his shaft. He moaned in appreciation, starting to move up and down as I gave him what he wanted.

I started thrusting up to meet him, then I rolled him over, putting his legs on my shoulders as I plowed into him.

"Oh.. fuck yeah, pound me," he demanded. I complied, thrusting harder and deeper as my orgasm quickly approached. I leaned down, kissing him deeply, and asked,

"Where do you want me to cum? On your face?"

"No, I want it inside.." he begged.

"Are you sure?" I asked, my pace quickening.

"Yes... breed me, daddy.."

It was all I needed to hear. I grunted loudly as I thrust all the way to the hilt. I came for all I was worth, each spasm draining me more and more. He wrapped his legs tightly around me, crying out as he came with me. I collapsed on top of him, breathlessly. He continued grinding his hips, the sensation almost too much for me as his orgasm continued, coating us both in his juices.

After we both came down, I carefully pulled out of him, my own seed leaking from his gaping hole. The scene of him laying back with my load leaking out onto his couch was the hottest thing I had ever seen. I cuddled up with him on the couch, gently tracing the outline of his figure with my finger as we both drifted off again.

-----

I woke up the next morning on Jack's couch, the gentle light of morning spilled through his front window. Thank goodness for Labor Day, we would both be sitting at the office, far apart from each other otherwise.

I heard soft rustling coming from the kitchen, and could smell a light aroma of breakfast foods. I lazily rolled over, fished my underwear out of the pile of clothes and followed the heavenly scent. I hardly suspected what I was about to walk into.

There was Jack, expertly working various pans on his small stove. Eggs, bacon, sliced fruits and croissants were already laid out on the table, with sausage and pancakes on deck. I had no idea he was such an expert chef, but the most surprising part was what he was wearing.

He had on a red apron with lace on the edges, the type of thing you'd see a typical 50s housewife wearing, and... that was it. The muscles in his toned back flexed and his perfect butt jiggled slightly as he moved about his tasks. Strangely sexy, I stood there and watched him put Gordon Ramsay to shame.

He had yet to notice me, so I waited until a lull in the action before walking up behind him, gingerly placing my hands on his hips and kissing his neck.

"I love a man who knows his way around the kitchen," I said softly in his ear.

He tensed up for a moment, then turned to face me. "Morning, lover," he replied as we kissed deeply. "I thought we would stay in today, if that's okay with you?"

"Well, I don't really feel like going back home anyways. Besides, I wouldn't have this amazing breakfast waiting for me there, or this hot guy either, so..."

"Flatterer!" He playfully smacked my butt as he turned back to put the finishing touches on this feast. "Grab a seat, be done in a sec."

I took my place at the table, enjoying the sight of the wonderful meal on the table, and the snack at the stove. He turned around and placed the last of the food on the table.

"Please, help yourself," he gestured towards the various dishes.

I dropped all pretense of modesty and piled my plate high. Turns out, an entire weekend of amazing sex requires a bit of fuel, and I was on empty. Apparently, the same was true of Jack as he followed suit. We ate, and ate and ate until there was barely a scrap fit for a mouse. We both sighed, perfectly sated.

"Where did you learn to cook like that? That was amazing," I barely managed, my stomach about to pop.

"I worked at this restaurant in college, they mostly served brunch, so I learned a few tricks about how to make really good breakfast food," he replied. "I can make other stuff too, but this is where I really shine, if I do say so myself."

"Well, I think you killed us both with this meal. I don't think I can budge."

"Do you think we can make it back over to the couch for a little TV time?" Jack asked.

"I think I can manage that. I'll take care of the dishes first and I'll meet you there."

"Oh, you don't have to do that." Jack responded.

"Please," I said. "It's the least I can do. Plus, that's how I was raised. Whoever doesn't cook, cleans."

"You're a good man, Charlie Brown." Jack laughed as he walked away, giving me one last look at his perfect ass. I swear he wiggled it as he walked away. I hurriedly rinsed and placed the dishes in the dishwasher, turned it on, and returned to the living room.

Jack was there, lying on the couch under a nice comforter. He smiled, excitedly patting the spot next to him. "Come on over, The Price is Right is on!"

I walked over and pulled the comforter over and cuddled with him. I could tell he was still mostly nude, though he was wearing underwear. My mind raced with possibilities, but my overfilled stomach stopped it in its tracks. Besides, we had the whole day, and Drew Carey was about to be on.

We spent the next couple hours shouting out prices, neither of us were any good, but it was fun watching other people win. Eventually, we both began fading into our respective food comas and took a nice nap on the couch.

At around noon, I woke up to Jack softly snoring next to me. I sat and watched him for a bit, admiring his breathtaking beauty. The only thing that broke the spell was the urgent need to piss. I quietly got up, took care of business and came right back. Jack was beginning to stir as I returned to the living room.

"Mmm.. nothing like a nice midday snooze." He said dreamily as he stretched.

"Especially after an amazing meal." I replied as I sat next to him.

"You're so sweet," he said as he leaned in to kiss me.

I kissed him gently at first, running my fingers through his silky hair. I looked him up and down as I went back in to kiss him deeper, tracing my fingers down his neck, chest and towards his stomach. He stopped me before I went any further.

"Hold on a sec, tiger," he said breathlessly.

"Oh, sorry I got a little carried away..." I sheepishly responded.

"No, it's not that. I just... I thought we could try something a little different."

"Oh yeah?" My mind raced with the possibilities. "What were you thinking?"

"Well... I thought maybe..." Jack covered his face, his cheeks turning bright red. "I've always wanted to..." He said something under his breath.

"Wanted to...?" I inquired.

"Be dominated..." He responded, his whole face flushing.

"You mean, like BDSM? Getting tied up and stuff?"

"No! I mean, yes but... I thought we could start slow. If you aren't into that, I totally get it. Maybe I shouldn't have said anything..." He trailed off.

"No, it's okay. I've never done that before, so I might need help understanding what you want, but I'd be willing to try. I just don't want to accidentally injure you or anything." I can't lie, it sounded exciting, but hurting Jack was the last thing I wanted to do.

"Are you sure?" His eyes brightened. "Don't worry, I'll tell you exactly what I want, and I know my limits, I promise." Jack assured me.

I nodded. "Okay, just tell me what to do."

Jack stood up and led me by the hand to his bedroom. "Okay, so first thing's first. I don't want you to think of me as Jack." He explained. "Think of me as your living sex toy. I want you to use me to get off, but also to deny me. Don't worry about making me cum, do the opposite. Don't let me touch myself, tease me but don't finish me until I beg you. I'll do whatever you want me to do to you, within reason. Also, safe word is pineapple. Okay, let's get started." He kissed me on the lips, then sat on the bed.

"Umm, okay let's see here..." My mind blanked. 'Whatever I want, huh?' I thought to myself.

"Uhh, sit on the floor." I said.

Jack immediately hopped off the bed and sat on his knees, hands on his thighs.

"Okay, look up at me, open your mouth."

He obeyed, his mouth opened sensually. I was imagining his tongue wrapped around my cock, but I wanted to savor this.

I leaned forward and rested my palm on his face, brushing my thumb against his full lips. His breathing quickened, but he continued sitting obediently. Emboldened, I put my thumb in his mouth. His tongue started to encircle it as he sucked softly. I worked it in and out, slowly, his saliva dribbling out the side of his mouth and onto his chin. My dick engorged with the sensation of his tongue and watching his obedient, hungry look. I knew he wished it was my cock, but I wasn't going to do that quite yet.

I replaced my thumb with my index and middle finger, beginning to fuck his face a little harder. He began moaning as I noticed his own bulge straining against his underwear, a wet spot starting to form. He was really getting off on this! I looked down and noticed my own growing wet spot.

With my free hand, I wrapped my thumb around the waistband of my underwear and pulled them off, slowly. His gaze shifted from my eyes to my dick.

"Ah ah ah, eyes up here." I gently commanded.

He looked back up at me, his demure expression only fueling my lust. I kicked my underwear away as I lightly stroked myself at the sight before me. I had another idea.

"Hands behind your back." I demanded. He quickly complied. I looked around the room and spotted his closet. "Sit right there, don't move." I went over and looked inside. As luck would have it, I spotted a scarf. I pulled it out and returned to him. I gave him a look, and as if reading my mind, he nodded hurriedly. I walked behind him and tied his hands together, then returned to face him. I used one hand to pull his chin down, opening his mouth wider as I guided my tip, brushing it along his lips. My heart pounded as he looked up at me, lust burning in his eyes. I pushed into his mouth as his lips wrapped around my shaft.