The First Time in a Long Time #1

Call me George. I'm your average guy: 6 foot, not fit, but not fat, average looking, worked the same, steady job for about six years, eat the same thing for lunch every day, boring type of guy.

I live in a pretty quiet city in the Western United States, population about 50,000. All the modern amenities without the hustle and bustle. The best place for me, honestly, because any more excitement than that would probably make my head explode.

I'm not an introvert, but I was content to just go in to work, put in my 8 hours, come home and surf the net, play video games, watch TV, and go to bed. Rinse and repeat. That's not to say I don't crave excitement, I just don't seek it out, really. That is, until I met Jack.

Jack was a new hire at my job. I wasn't a manager or anything, but they asked me to show him the ropes, get him comfortable enough and make sure he knew where anything was in case he had questions.

My job was pretty boring, just sales for a big computer company. It paid the bills, and I was fairly good at it, so I stuck around. Definitely the most interesting part was "training" Jack.

He was really cute, probably the cutest guy I'd ever met. He was a couple inches shorter than me (though plenty big where it counted, as I would come to discover) long, dark wavy hair, skin like porcelain, unblemished except for a dusting of freckles and a small scar on the side of his lip that gave him an eternal grin. He was thin, but not gaunt, and had a husky, yet angelic voice.

He greeted me with a warm smile, and when I reached for a handshake, his touch caused a warmth to bloom in my stomach. He actually gave me butterflies! I had never experienced that, before or since.

We made our way to his cubicle (unfortunately, he was on the other side of the office, so it wouldn't be easy to socialize) and I showed him all the various things he would need to be a success at Boring Computer Sales, Inc. I shadowed him on a couple of sales calls to make sure he had the hang of the script, which he quickly mastered, but I kept making excuses to stick around, wanting to really "make sure he was comfortable, because new jobs can be tough" or whatever bullshit line I fed him. He giggled, deferring to my judgement.

We talked non stop between calls, learning about each other, our backgrounds, likes and dislikes, anything and everything. I kept getting annoyed glances from his neighbors (I'm pretty sure this was the most I had ever spoken at work, and everyone seemed to think I was slacking off) but I just ignored them.

Once lunch rolled around, I did something I had never once done in my time there: I went out. I insisted on taking Jack to a local bistro to celebrate his first day. I didn't realize until later how strong I was coming on, but I'm glad I did, as he seemed to enjoy the attention I was giving him.

We walked the short distance from our office building, chatting away and joking around as we walked. After a short while, Jack spoke very candidly.

"George, I just wanted to thank you for today. I just moved here this week from out of state, and I don't really know anyone, so your kindness has meant the world to me. If there's anything I can do to repay the gesture, just let me know."

I thought for a moment. I had never felt so completely enamored with someone at first sight, and I knew I would kick myself for not asking him out. So, with a boldness I had never felt before, I said,

"Well, I would love to go out on a date with you sometime."

Jack looked at me in shock. Had I screwed up? Did I just assume he was gay? What gave me the right to ask him out after knowing him for all of a couple hours? Would he feel like he was being harassed? I hadn't considered any of these things, and my blood ran cold when he didn't respond at first.

"I, uh.. that is, I meant..." I couldn't form a coherent thought. I had messed up big time. Just as I was about to turn around and run, however...

"I would love that," he replied, blushing a bit. He bit his lip a little, avoiding direct eye contact.

"Truth be told, you're exactly my type."

His type? As if reading my mind, he continued.

"Tall, dark and handsome."

I had never been described that way, and I certainly didn't see it, but I wasn't in any position to argue. The cutest guy I had ever met told me I was his type. I knew when to shut my mouth.

"You know..." he went on, "I'm not really that hungry. I think I would rather find a nice, quiet place to... talk, if that's okay with you?"

I was nearly catatonic. To recap my day so far: I met a cute guy at work, was assigned to train him, we instantly connected, I invited him to lunch, which he eagerly accepted, he also accepted my invitation to a date later, told me he was attracted to me, and now I'm pretty sure he just propositioned me. What was up with today?

"Yeah, there's a park about a block away, there are plenty of trees to sit under," I finally replied.

"Sounds magical," he replied as he stepped closer to me, holding his hand out. "Lead the way."

We immediately made our way to the park. There was a somewhat secluded area I had seen before on a walk, and we headed straight there. As if waiting for us, there was a small clearing with enough tree cover to give us privacy.

We both sat in the middle of the clearing, gazing into each other's souls. He had piercing eyes bluer than the ocean. They stared into my being, stripping away all pretense, inhibitions and other nonsensical human constructs, peering directly into my spirit. I was completely under his spell.

He leaned closer, his hot breath sending fire through my veins. I leaned in to meet him. Our lips gently brushed, not quite kissing just yet. We held this position for what felt like an eternity, then slowly moved into each other.

Our kisses were light, at first, exploring each other's lips, but soon our tongues began to join. I lightly brushed his hair aside, kissing him more firmly. His hands began to caress my chest. I felt a familiar tightness in my groin as the blood rushed to it.

I began to run my hand down his side, interlacing my fingers with his as he laid me in the grass, slowly unbuttoning my shirt with my teeth as he simultaneously unbuttoned his. I ran my fingers through his hair as he continued his journey south, eager to claim his prize. I leaned my head back, eyes closed as I felt him unbutton my pants and freed my straining cock. I heard a soft gasp as he wrapped his slender fingers around my shaft, and he slowly began to work magic on it.

He lightly kissed the tip as he gently stroked me, becoming more emboldened as I groaned in response. Soon, he was suckling the tip, eventually abandoning his hand altogether as he took me deeper into his mouth. Each inch he took me further elicited uncontrollable, deep moans from my throat. Soon, he had taken me in completely, and as I felt the back of his throat, I nearly lost control.

As if sensing this, he stopped, squeezing the base of my cock as he whispered, "Not quite yet, what about me?"

I opened my eyes and looked up at him as he sported a mock pouty face, hands comically placed on his hips. "Don't I get a turn?"

Wordlessly, I sat up, gently pushing him down as I went straight for his belt. I wasted no time in getting to work, I wanted, no, I NEEDED to taste him. His underwear was slick with precum, and as I pulled them down, the most beautiful cock I had ever seen sprang forth.

He was a little smaller than me lengthwise, but he was girthier. The skin was soft, and there was a string of precum dripping from the perfect, pink head. He was also completely hairless, save for a well manicured triangle at the top of his pelvis. I wouldn't have any trouble taking him in all the way, but it would definitely stretch my mouth. I didn't care though.

I lapped up his juices as he moaned softly. I began tonguing his frenulum as I lightly worked his shaft with one hand, and gently caressed his balls with the other. I continued like this for a bit before wrapping my lips around his head. I greedily licked his tip, sucking him loudly, as I had long stopped caring if we were caught. I just wanted to blow his mind (and his cock.) I kept taking him in further until I got to the base, his pubic hair tickling my nose. With him completely in my mouth, I worked my tongue along his length, wetting a finger with my drool and lightly began probing his anus. He slowly rocked his hips as he moaned, softly cursing under his breath.

After this, I was finally ready to take it to the next level. I removed my finger, propping his legs up over my shoulders, but I realized, however, that I didn't have a condom, and unfortunately neither did he. We both agreed that it wasn't a good idea to go any further without one.

A bit crestfallen, I got another idea. Our cocks both still slick with spit and precum, I wrapped my hand around both, and slowly began pumping my hand. I had always seen it done in porn, but had never tried it in real life. The feeling was exquisite. I felt his cock pulse against mine, slowly increasing my speed and bucking my hips as our heartbeats quickened. We both began moaning loudly, and before I knew it, we were cumming in tandem. I looked down as rope after rope shot from our cocks onto his bare chest, threatening to drown him in our combined orgasm.

After what felt like an eternity, I panicked and checked the time. Thankfully we had only been at it for about half an hour, and we still had plenty of time on our break. I wiped up a bit of our cum with my finger and tasted it, our combined flavor intoxicating.

"I'm sorry, I didn't think to bring anything for clean up," I said between gasps of air.

"Don't worry," he replied. "I hear it's great for the skin," he said as he began to rub it into his chest.

"Your skin is so soft, you must cum a lot on yourself," I joked.

He laughed, "Not normally, no, but I'm looking forward to this new skincare routine."

I laid next to him, gently caressing his face as I planted several small kisses on his lips, nose and cheeks. We then shared a final, passionate kiss as we began to redress.

"So, about that date..." I said as we began the walk back to the office. " You free this Saturday?"

"I'm free whenever you want, babe," Jack replied. "Oh, and next time, PLEASE be sure to bring a condom..." He leaned in and whispered in my ear: "I want you to destroy me."

My cock began to harden as the words left his lips. Looks like I was stocking up on rubbers.

-----

In preparation for our upcoming date, Jack and I exchanged numbers. He told me he couldn't wait, and clasped hands and leaned his head on my shoulder as we walked back. We made sure to separate a bit as we got back within view of the office, didn't want to take a chance at starting any office gossip on his first day.

As soon as Jack and I got back from "lunch," the manager whisked him away for some last minute orientation bullshit, so I didn't get to see Jack for the rest of the day. I was sitting at my desk making sales calls when my phone vibrated. I glanced over at it and saw it was a text from Jack. I opened it and was greeted by a selfie of him rolling his eyes playfully as our boss was in the background, completely unaware.

He was giving his "Newbie Speech," which was little more than corpo terms like, "teamwork, synergy, responsibility," dumb shit like that. I had to sit through it when I first started, but I never had anyone to commiserate with. I stifled a laugh and texted back, "Welcome to the club, lol"

A few minutes later, I got another text. This time, it was a shot of Jacks crotch with a noticeable bulge. It read, "Just thinking about lunch. I wouldn't mind going back there some time ????"

My cock immediately swelled in my pants. After a cautionary glance around, I quickly pulled my pants tighter and snapped a pic. I responded, "I wish you were under my desk right now, I miss your hot, wet mouth"

I sent it just as someone walked by. I quickly put my phone away and got back to work. I got another text a few minutes later, but was too scared to look at it. We were playing a dangerous game, and I definitely didn't want to get fired. I decided to check it when I got off.

5pm finally rolled around, and Jack walked by my desk. "Hey there, just wanted to thank you for helping me out today, sir." He held his hand out. I noticed several people walking past, including our boss.

"Sure, no problem. Jack, was it?" I shook his hand.

"Yeah, Jack. And you were George?"

"Yeah, George."

"Okay, well I'll see you around, George," he called back as he walked out the door.

My boss walked up and thanked me for helping out this morning, but to "dial back the chatter next time." I gave him a fake military salute as I gathered the last of my stuff and walked out.

As soon as I got to my car, I frantically opened Jack's text, and was pleasantly surprised. He had gone to the bathroom at some point and took a selfie with his shirt pulled up by his mouth, and his pants pulled slightly down, just to the top of his pubes.

"I can't wait to get covered in your cum again ????"

It was all I could do not to whip my cock out right there in the parking lot. I put my phone on its mount with the picture still pulled up as I drove home. I nearly got in a couple wrecks because I was both speeding home and couldn't keep my eyes off his perfect body.

Thankfully I got home without being pulled over. I grabbed my phone, got out of the car and ran up the steps into my building, threw the door to my apartment open and ran inside. I threw my stuff down and got on my bed, pulled my dick out and snapped a picture. I had never sent a nude before, but I thought it wasn't half bad, and sent it back, saying, "Fuck you're so hot, I can't wait to be inside you." I slowly pumped my cock, eagerly waiting for the next message. Not even a minute later, I got video. This one was the hottest of all.

Jack was laying on his side, completely nude. He was spreading his ass teasingly, his cock tucked between his legs. "I can't wait for you to wreck me with that fat cock."

Before I had the chance to respond, I got a video message. He was in the same position, fingering his ass as he slowly bucked his hips. I could hear the wetness of his finger probing, and I could see a bead of precum as he worked it in and out. "You know..." he said in between heavy breaths, "some guys can cum just from getting fucked..." he continued, moaning softly, "but you'll have to wait until Saturday to find out." He winked, and the video ended.

"Ffffffuuuccckkkk..." I said loudly as I came all over my pants, shirt and hand. I sat there for a minute, totally spent, then took a final picture of the mess I made. "This, but inside you." I replied. He just sent back "????"

Saturday couldn't come soon enough.

-----

The rest of the week was a blur. I was hardly concentrated on work, my date with Jack on Saturday was all that filled my mind. My sales started to suffer, but thankfully I was able to scrape by unnoticed, as it seemed to be a slow week for everyone.

I had lunch with Jack every day, and every day all I could think about was what we were going to do to each other. I thought back to his last sext: "Some people can cum just from getting fucked, guess you're going to have to wait to find out." I couldn't wait any longer. I felt like I was a horny teen again, sitting behind the gym, feeling up some guy (or girl, publicly I was straight. I wasn't outwardly bisexual until college.)

I had to wait, though. Jack could sense my "frustration" and told me it would be so much sweeter if we waited. Of course, he was right. I had just broken a year long dry spell, and I was just being ravenous. I could wait.

Finally, Friday rolled around. I lingered, taking extra time to pack my things. My boss was never around on Fridays, so I knew no one else was going to stick around. That is, except Jack and I.

We waited until everyone else was gone, and walked out of the building, hand in hand. Our company was pretty strict on office dating and/or sex, so we had to be discreet. We agreed to keep our socializing to a minimum in the office, and we never left for lunch at the same time. Nobody really seemed to notice I had started going out every day, but then again nobody really talked to each other, so it was hardly noticed.

We parted ways once we got to our cars, bidding each other goodnight. Stealing these little moments was what I lived for these days. I told him I would pick him up at 7pm the next day, and we would go someplace nice for our first official date. He told me he couldn't wait, and we got in our cars and left. I hardly slept that night.

Finally, it was Saturday. I did something else I hadn't done in years: went clothes shopping. I wasn't a fashionista by any means, but I had watched enough Queer Eye to know what a drab dresser such as myself could upgrade to. I got a nice button down, a pair of chinos, and some nice shoes. Nothing too flashy, but more colorful than what I usually wore.

I lived about 15 minutes away from Jack, and my shopping was done before noon, so I had seven hours to kill. I sat down to play some Baldur's Gate 3, which kept me busy for a while. I stopped at about 530 to get ready.

After a shower, shave and light manicure, I was ready. I headed Jack's way and texted when I was outside his building, and he responded that he would be right out. It was a nice enough area, and I was a little jealous that he lived closer to work than I did. First world problems, right?

I saw a woman exit the front, and she began approaching my car. I wasn't sure what her deal was, but as she approached my car she started to look familiar. Then it dawned on me: it was Jack.

He had his hair done up in a 20s Flapper girl style, and was wearing a stunning blue dress. He had also put on some makeup. Subtle, but tasteful. He was gorgeous

He got into the passenger seat, and laughed at my vacant expression.

"What's the matter? Were you expecting someone else?"

I snapped out of it. "No, I just..."

He giggled, "I like to dress up when I go on dates. Sue me."

I sat there, stunned. After a moment, I gathered my composure. "You look amazing."

Jack smiled, the small scar amplifying it. "You mean it? I'm sorry, I should have told you I was going to dress a little... fancier. You said we were going somewhere nice, and... Well, sometimes I feel a little girlier and so I dress accordingly. This isn't weird, is it?"

"No, not at all, I admire your bravery and authenticity. Plus, you really are beautiful, no matter what you're wearing."

It sounded so corny coming out, but Jack blushed and did his cute lip bite.

"Thanks, babe. So, where are we going?"

I smiled and put the car in gear.

He paired his phone to my car and cranked up his Spotify playlist. The first thing that came on was Lady Gaga, and I had to laugh.

"I was obsessed with her in middle school! I was such a little monster!" I shouted.

"ME TOO!" Jack replied.

We both sang our hearts out to Gaga, Beyonce, Nicki Minaj, and even a little Queen.

Finally, we arrived at the restaurant. It wasn't a Michelin star rated place or anything, but it was fairly upscale. I handed my keys to the valet and we walked inside.

We got a table near a fish tank with a great view of the downtown skyline. It was on the tenth floor of this nice building, had an attached bar with a dance floor, and had the best waiters I'd ever seen.

Our waiter, right on cue, came for our drink orders.

"I'll have a glass of the Merlot," I ordered.

"And, for the lady?" The waiter asked.

Jack grinned at me. "I'll have a Cosmo."

"Wonderful choices. I'll be back momentarily."

As soon as the waiter was out of earshot, Jack giggled. "Guess I pass pretty good?"

"Jack, you make Jennifer Lawrence look like a bull dog."

Jack laughed. "Don't talk shit about my girl J Law!" He tossed his hair back in fake outrage. "That woman CARRIED the Hunger Games movies!"

We both laughed, continuing to talk movies, music and celebrities until our drinks came. We both went ahead and ordered food. Neither of us had eaten that day, probably out of nervous anticipation of our date.

The food took a while, which gave us plenty of time to chat. I thought we would run out of things to say, considering how much we had already learned about each other this week, but the only time we stopped talking was when the food arrived. It was divine, as expected.

Once dinner wound down, I paid (I insisted, like a gentleman) and we headed to the elevator.

"I'd love to come back to the bar another time, it looks like they have a killer dance floor." Jack said.

"Oh, I'm not much of a dancer..." I admitted.

"Well, if you wanna be my lover, you gotta get over that and learn." He said as he did some exaggerated moves.

I laughed, "Guess so."

The valet got my car, and we headed back to Jack's place. He let me through the gate into the parking lot, and before the car had so much as stopped, we were all over each other.

We were kissing each other fiercely, tongues intertwined as I began to run my hand up his thigh towards his perfect package. As I touched it, I noticed a distinct lack of layers between the dress and his dick.

"Are you...?" I asked between kisses.

"Oh yeah..." He replied.

I lifted the dress up, and there he was in all his nude glory.

"I can't believe you weren't wearing anything that entire time..." I said, breathlessly.

"I just made sure to avoid air vents, didn't want a Marilyn Monroe situation."

Finally, I had to break away. "I think we'd be more comfortable inside, my car isn't very big."

"Yeah, good point. This isn't high school, I can have boys in my room whenever I want now!" Jack said.

He led me into his apartment. It was nicely decorated, very modern. He took me by the hand and led me to his room. He had a nice king sized bed, which he flopped onto.

"Well, this has been nice. See you Monday?" He joked.

I didn't respond, just wordlessly began unbuttoning my shirt.

"So it's gonna be like that, huh?" He said as he began to undress.

"Wait," I said.

He nodded as I continued undressing down to my underwear. I approached the edge of the bed, carefully removing his high heels. I started at his feet, kissing my way up his perfectly toned legs. He sighed softly as I continued upward.

Finally, I stopped at his crotch. He was pitching quite the tent under his dress, which somehow made it so much sexier. I reached out and grasped his cock, brushing my thumb along the tip, which elicited a sharp gasp from Jack. I looked up at him, his eyes were closed and his mouth slightly agape. I lightly stroked him for a bit, his dress becoming damp with his precum. I then lifted the dress and planted a gentle kiss on the head, then devoured it.

I was so pent up, I moved like I had never moved before. I worked my tongue along the shaft as I vigorously sucked, massaging his balls and reaching up to play with his nipple. He began to groan louder, rocking his hips to meet my mouth.

I reached down and grabbed my own cock, now soaking through my own underwear. I began pumping as I took him all the way to the base. I was determined to make him cum.

Finally, I received my reward. He moaned loudly as he pumped his hot load into my mouth. It was sweet, I savored every drop, though a small amount dribbled down my chin.

He took my face in his hands and kissed me deeply, sharing his cum. God, that was hot.

"I need you, NOW," he demanded.

He reached into his bedside table and pulled out a condom and some lube. He tore my underwear off, opened the condom and expertly rolled it over my aching dick.

"How do you want me, babe?" He asked.

"On your back," I asked. "I want to look into your eyes."

Without another word, he laid back, and I ran my eyes along his perfect body. His skin was smooth as silk, and a faint sheen of sweat made him glow. I lubed up a finger and slowly inserted it, being careful not to hurt him. It slid in with some resistance, but not too much.

"Don't worry about being gentle, babe. I've been playing with myself all week to get ready for that fat cock. Just put it in me..."

I didn't want to disappoint Jack. I liberally applied the KY to his perfect, pink hole and lined myself up. We made eye contact as I gently pushed, and before long I was fully inside him.

I stayed there for a moment, his walls clamping down on my dick, before slowly withdrawing my swollen manhood until just the tip was in, and I slid right back in up to the hilt. We moaned in unison as I continued my motion, grinding my pelvis against his ass at each thrust. The noises he made only further empowered me as I threw caution to the wind.

I had had sex before. Hell, I had fucked before. But this was different. We MATED. I was a wild animal, I slammed every inch I had into him, no mercy.

"Oh yes... YES... fuck me!" He cried out. He didn't give a shit if his neighbors heard, and neither did I.

"Fuck, you're so tight! I'm not gonna last long!" I shouted in response.

"Yes, fill me up, baby! Fill me all the way!"

In one swift motion, I went balls deep, then rolled him over so he was on top.

Surprised, he got the idea and started riding me. The slap of his cock onto my stomach made me even harder. I reached up to pull his face down as I shoved my tongue into his mouth. I grabbed his hips, helping him bounce on top of me.

"Oh fuck, I'm close baby..." He said as I continued ravaging him.

"Me too..." I barely got the words out as I felt a familiar tightening in my scrotum. I couldn't hold back as I began pumping my seed into him.

"Oh... fuck!" I shouted as I came. I felt like I was on a rollercoaster at the last dip, every part of my body tingled as my cock spasmed.

His orgasm came shortly after. Though not as big a load as last time, he still came a fair amount. I ended up with a small puddle on my stomach as we both came down from our mutual high. He collapsed onto me, our chests heaving as we fought for breath.

After we came back to our senses, I gingerly pulled out of him, checking to make sure the condom was intact. I didn't see how a condom could hold so much cum, but thankfully it did the job. I removed it, tied it off and set it on his bedside table, them planted a kiss on his forehead as he laid his face on my chest.

"That... was amazing..." he said as his eyes fluttered, fighting his exhaustion. I grabbed a nearby blanket and draped it over us as we both drifted off.