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Dylan's Lucky Day

Category:  FATHER-SON  |  PUBLIC 

Cowritten with: Tom R


    Setting the last of my boxes in the corner of the living room, I collapsed into my favorite chair and let out a long sigh. A couple of friends had helped me with the big stuff earlier in the day, but I'd spent the last two hours on my own, bringing boxes up two flights of stairs. Finally, I was done! 

    I looked out my living room window at a decent view of Golden Gate Park. Or at least the tops of the trees in the park, though any view counted for a lot in this city. After years of struggling to get by in San Francisco, working two (and at times three) jobs to pay rent while getting my bachelor's degree, I finally felt like I'd "made it" here. I'd applied for a master's program and a scholarship, and had been accepted for both. When school started next week, I would also begin working as a teaching assistant for the university, which meant my days as a takeout delivery driver might be numbered. And best of all, at 23, I'd managed to score what everyone under 35 in SF dreams of: an affordable one-bedroom apartment with off-street parking.

    Part of me idly wondered if I should try for the life-satisfaction trifecta and finally find a long-term boyfriend. "Slow down," I thought to myself. "Don't get too greedy with the good fortune." Even though I enjoyed being in a relationship, now that I was finally living without roommates I wanted to enjoy the freedom of having hookups over anytime I wanted. I knew that the first time I told a guy "I can host" without having to worry about sneaking them in or making too much noise would feel so pleasing! And why wait, come to think of it?

    I pulled out my phone and opened Grindr for the first time in a couple of weeks. Every free moment lately had been about packing, making moving arrangements, and getting things together for grad school, so it would be nice to get some fun back in the mix. I realized with no small amount of excitement that this would be the first time I'd be perusing the options in my new neighborhood.

    "Show me what you got, NoPa!" I thought to myself and smiled. This part of the city, North of the Panhandle, was a mix of nicer apartments, expensive homes, and hipster mini-enclaves. And it was fairly close to the Castro, so I expected there to be a ton of guys looking at any given time. And I was not disappointed. Scrolling through hundreds of faces and bare chests, I felt glad that I'd updated my own Grindr pictures during the summer. I'd done well with diet and fitness this past year and I was pleased I had something to show off.

    Since I was new to this part of the city, I was suddenly inundated with dozens of "hey"s and "looking?"s. Satisfied with my popularity, I started to peruse the new prospects. A few guys jumped out at me for various reasons. I noticed one in particular, a 20-year-old Latino less than a mile away. He had a captivating smile, and the nerdy T-shirts with comic book characters he wore in a couple of his photos made me think we had some common interests as well, on top of both feeling horny.

    "Hey," I texted him.

    "Hi 😉," he replied. "How you doing?"

    "Good. A bit tired. I just moved in this morning, so I'm just settling down."

    "Welcome! 🥳 Where did you move from?"

    I went on to tell him that I was from Sacramento, but been living in San Francisco for five years now. He was a local boy, born and raised, and we chatted about that for a while. I caught myself smiling several times during our exchange. His banter was witty and just the right amount of flirty. I wanted to see him as soon as possible, and since I didn't know if he could host or not, I decided to invite him over.

    "Drop me a pin. I'll be there in 20," he replied. "Btw, I'm Brody," came a message a few moments later.

    I realized we hadn't even exchanged names during our conversation. "I'm Dylan," I replied, and went to get ready.

    I took a shower, happy I didn't have to rush through anything. Brody's profile said he was a total bottom, and I already knew I wanted to top this cute boy, so it was perfect. I threw on some boxers and when he showed up I answered the door like that, near-naked.

    Brody was a little shorter than me, and a little skinnier, though I knew from the photos he'd sent that he was nicely toned under what he was wearing. He'd also sent me a photo of his bubble butt, that I couldn't wait to see in person!

    "Hi," the boy said and I let him into the apartment. The door was barely shut when he leaned forward and gave me a kiss.

    "Hey," I said. "Nice earring."

    On his right ear, Brody was wearing an earring with a little dangly cross. It caught my eye because it wasn't in any of his photos.

    "Thanks! I just got it pierced this morning."

    We didn't waste any more time talking about accessories. Brody stepped forward to kiss me again, even more passionately this time. We made out for a while and I pulled his shirt off. Both our tongues found their way to necks, nipples, and abs as we enjoyed each other's bodies. Sometimes younger guys liked to take things slow, but Brody seemed to have no such qualms. I led him to my bedroom, where he kicked off his shoes and slid down his jeans, revealing a black designer jock. The smile that had initially won me over appeared on his face, and seeing it in person was even better.

    "God damn, you are sexy!" I growled at him, sliding down my boxers to reveal a hard eight inches.

    "Let me get that ready for you," he responded, kneeling down at the side of my bed, facing me, but keeping his eyes on my cock. Brody reached down to stroke his own dick, clearly erect and filling out the pouch of the jock very nicely. I stepped forward and he opened his mouth, letting me slowly slide in. I let him set the pace, and he clearly enjoyed his work, giving me the perfect combination of hand, mouth, and tongue stimulation. I considered myself an outstanding cocksucker (plenty of guys had told me as much) and Brody was quickly proving to be at the same level, just a few minutes into this.

    I closed my eyes and enjoyed his talents, gently running my fingers through his thick dark hair. After a few minutes, the pleasure started to intensify even more! I slowly backed up, taking my cock out of Brody's mouth, but keeping one hand on his cheek and jaw, my thumb touching his lower lip. He still had my cock in his hand, slowly stroking it, as he looked up at my eyes.

    "If you keep doing that, I'm gonna cum inside your mouth," I said.

    "No," he let go of my cock. "I want you inside my ass."

    "Yeah?" I teased, wagging my boner in his face. "Think you can handle it?"

    "Fuck, yes. I've been taking loads since I was 16."

    He jumped up and turned around, poking his ass out in my face, winking at me with his smooth hole. I could already tell this was going to be a fantastic fuck.

    Seconds later, my prediction was proven to be true. Brody was on all fours on my bed with me behind him. We were in sync from the start and he knew just the right way to push back into me. I leaned forward, pressing my chest into his back, so that I could kiss the back of his neck as I continued to thrust inside him. Brody reached a hand up to grab the back of my head, turned his face toward mine and pulled me into a kiss. We enjoyed this position for quite a while, slowing down only to prevent ourselves from cumming just yet. 

    After some time, I reached around his hips and thrust my hand into the pouch of his jock. Very pleased to find that he was thicker than average, really filling up my hand, I started to stroke him. His cockhead had been wet with precum already, so he was quickly slicked up enough for me to tease him in all sorts of ways. Brody's nuts were pulled tight up against his body, and I started fucking him a little harder when I realized I could probably make him cum while I was inside him. Not every bottom liked to cum while getting fucked, but it was one of my favorite things as a top. I shifted us around a little so that I could press myself into his prostate as I thrust into him. He sensed what I was doing and leaned into it, and soon he started shouting obscenities in between gasps of air. I felt his cock throb in my hand and his ass tighten around my shaft.

    I kept jerking him as Brody shot his load into my hand and his jock, but I slowed my thrusting down as he finished, giving him a chance to relax. I wanted to keep pounding him and plant my load as far inside him as I could, but I decided to do something else first.

    "Turn around," I said.

    Slowly, Brody started to rotate his body around my cock. All the while, I stayed inside of him. Now that we were face-to-face, I started to pound him harder again. Brody moaned loudly, with an expression of utter pleasure on his face. I loved seeing him like this, and I leaned in and started kissing him. It was our hottest kiss yet! As our tongues wrestled, in this intimate moment, I started to shoot my cum inside his ass, just like he'd asked me to.

    "Mmm, yes, load me up. Breed me," he moaned as I kept him wrapped in my arms, depositing my spunk inside him. After a couple of minutes in that position, we finally fell back onto the mattress, catching our breath and even dozing off a little.

    We found ourselves cuddling and giggling as we awakened. I realized I was starving. It was past noon now, which meant it was lunch time. I didn't want Brody to leave just yet, so I asked "Are you hungry? I'm thinking of ordering a pizza from downstairs."

    "Hell yeah," he replied right away, "I'm starving! You had me working up an appetite." I grinned as he cuddled back up, and I reached for my phone.

    A short while later, we were sharing a huge pizza and a couple of sodas while watching cartoons naked in my living room. The place was a mess, but Brody didn't seem to mind. He was super easygoing. We talked about school; his major in design and my master's in art history. When I pulled out a joint, Brody seemed thrilled and happily accepted to share it with me. Before I knew it, a couple of hours had passed in a flash.

    "I gotta go, I'm working tonight," he said, putting his clothes on.

    "That's alright. I need to clean up around here anyway," I replied. 

    I smiled as I watched the cute boy hopping on one leg to put his sock on. For a first hookup in my new apartment, this had gone splendidly!

    "Hey, listen... Let's do this again soon," I said as I held the door open for him.

    Brody smiled and said "I'd love to." Then, he leaned in for a kiss, sending shivers down my spine.


    I spent the next few hours tidying up my new place. Thankfully, since I didn't have too much stuff, it seemed to be going by quickly. By that evening, I was almost done. I took another shower, and wondered what to do next. That's when I realized: I was horny, yet again. But this time, it was a little bit different.

    Fucking Brody and shooting a load in his ass made me crave cum inside my own hole. I needed to get fucked! I reached for my phone, and this time I decided to try out Scruff. I figured it might be easier to find a top on there; besides, when it came to being fucked, I preferred bottoming for older, daddy types.

    There were several guys I'd seen earlier on Grindr, some of them even using the same profile photo. But there were plenty of unfamiliar faces (and other body parts) to scroll through. Soon, I had an appointment with a 45-year-old stud who lived within walking distance. Feeling charged up, I picked out a pair of pants that made my ass look great and I was on my way.

    Delivering takeout for a few years had helped me spot the high-end apartment buildings quickly, even the ones that didn't look super fancy on the outside. The old, weathered San Francisco exteriors sometimes concealed quite a bit of splendor, and I could tell from the lobby that the building where this man lived was one of those places. Even the elevator seemed top-of-the-line.

    The daddy from Scruff looked just as handsome and steamy as the photos I'd seen, and he smiled warmly as he welcomed me into his apartment. He had fair skin and light brown hair cut in a flattering way. He introduced himself as Thorne, which was a name I'd never heard before. It made me think of the suave patriarch characters on the daytime soaps my mom loved to watch.

    The apartment was big and tastefully decorated. Thorne had said he worked "in tech" and I figured he was doing pretty well for himself. Judging by the number of doors in the hallway, I guessed that the place had at least two bedrooms. He hadn't mentioned anyone else living here, but that didn't mean anything. He could have a spouse and three kids for all I cared; I was here for one thing.

    Thorne offered me a glass of wine, which I accepted, and we didn't bother with too much chit-chat. I could tell he was horny, and before long he was lying on his bed and I had his cock in my mouth. He was both long and thick, and for the second time today I enjoyed the feeling of a solid piece of meat in my hand. We moved into a 69 position and he started to work on my hole while I deep-throated him. I was happy to have him open me up, given the size of his cock, and he knew just how to work my ass with his tongue and fingers. We got to the point where he had four fingers in me, the first two from each hand, and he had me so worked up that I was losing the ability to focus on his cock in my mouth. So I knew it was time for it to go into another orifice.

    Thorne sat up with his back against the headboard. I got on my knees and straddled his hips while facing him, and we kissed deeply as I lowered myself down onto him. I moaned loudly as his cock penetrated further than his fingers had just a few moments earlier. Finally feeling that fullness that I'd been craving, my brain switched into full fuck mode and I started riding his cock like there was no tomorrow.

    "Fuck me, Daddy," I heard myself moan. Not every older guy liked being called that, and I'd learned not to jump right into using that word. Still, sometimes my lust got the best of me and I couldn't hold it in. The whole dad-son thing was a longtime fixation for me, and verbalizing that when with an older guy was something I absolutely loved doing. I was very happy to hear and feel Thorne respond well to it.

    "Yeah, boy?" he said in a deep voice. "You like feeling that daddy cock up inside you?"

    "Uh-huh," I whimpered, closing my eyes and losing myself to all of it. "I need your daddy load deep in me. I need it so fucking bad!" I fell into him more, burying my face in his neck, and he wrapped his muscular arms around me and pulled me close in.  Sometimes I'd be fucking myself onto him as he pushed upward. And then other times, I relaxed everything and let him pound up into me. He played with my cock, and even when he wasn't, it was rubbing against his hairy midsection and keeping me right on the edge. The daddy talk continued, and though I noticed he didn't call me "son" like most other guys liked to, "boy" did it for me just as good. Before long, I was shooting my load onto his firm stomach.

    "I love making my boy cum," Thorne said as he eased up a bit, giving me a moment to recover. "Are you ready for your daddy's load now?"

    "Fuck, yes," I responded. When Thorne started shouting that he was going to cum, I grabbed his head and kissed him hard, just like Brody and I kissed when I came in his ass this morning. I felt Thorne's load filling my insides, and I squeezed my hole around his cock, draining every last drop of daddy cum.

    We were both covered in sweat, which mixed with my cum in between us, and by the time Thorne's orgasm subsided we were both wiped out, trying to catch our breath. It had been a more intense fuck that I had expected, and it was exactly what I needed.

    After a few minutes of sticky cuddling, Thorne rose and led me to his incredible shower. Water seemed to spray us from every angle and it felt amazing, just as it did afterward when the older man dried me off with an extremely soft towel. We didn't talk too much but it wasn't awkward, maybe because both of us felt so satisfied and it was an easy feeling to relax into. I was sitting on the couch and tying my shoes, when Throne emerged from his bedroom, also fully dressed.

    "I'm starving," he said, giving me a warm look. "The bistro up the street has tables on the roof. Want to go get dinner?"

    I had to admit, I was taken aback by the offer. This encounter had already exceeded my expectations, and now I was being offered a meal on top of it.

    "Sure," I replied. "I'd really like that."

    The bistro ended up being a really high-end place, so I was glad we sat outside, since my casual attire might have felt inadequate in the main part of the restaurant. Thorne wasn't wearing anything especially dressy, but he was the kind of man that could make jeans and a polo shirt look formal just by how he carried himself. He ordered us a bottle of wine and some appetizers, and once again that day, I found myself deep in unexpectedly pleasurable conversation, getting to know someone new.

    Since the experience with Brody was still so fresh, I couldn't help but compare how different it was from taking with Thorne. Brody and I had connected the way that people do when they're in the same place in life. We smoked weed and ate junk food and thoroughly enjoyed being silly and messy together. With Thorne, there was the older/younger power dynamic to some degree, but he wasn't someone who pressed that to any advantage conversationally. He was open to hearing my point of view on whatever we discussed, and didn't try to follow every statement of mine with an "older and wiser" take on the same matter. I had noticed certain older men doing that when they talked to guys my age, but Thorne really treated me like an intellectual equal, which I appreciated.

    By the end of dinner, I found that I'd actually forgotten we'd fucked a short time before. This felt like a proper date, something I hadn't been on since... well, a very long time. Besides, this was by far the most elegant date in my life. We were some of the last people to leave the restaurant, and as we walked back to Thorne's building, before I could bring up the subject of getting together again, he beat me to it.

    "I'd love to invite you up for another glass of wine or maybe... to stay the night, even," he said, faltering a little at the last part, as if he'd confessed something he hadn't meant to. I felt my heart flutter a bit, realizing he might be a little smitten with me. "But, um... my son Rickie is probably home by now and... well, frankly, I'm still worn out from earlier."

    I laughed in response, letting him know it was fine and thanking him again for dinner. I wasn't too surprised to find out Thorne was a "daddy" outside the bedroom as well. I'd hooked up with several guys with kids in the past, and if anything, it only made me want to get to know him more.

    We stood in front of Thorne's building for several minutes, neither of us wanting to say goodbye. Finally, we ran out of smalltalk. "Go tuck lil' Rickie in," I said. "I'll see you soon... Daddy."

    When he heard that, Thorne smirked and came in to give me another kiss. He put his left hand on the back of my head and pushed me closer. Meanwhile, his right hand reached for my ass, grabbing it and squeezing it for the whole street to see. We made out like this for a couple of minutes, during which several people passed us by. Thorne ignored everyone else, kneading my ass obscenely while several couples, singles, and families walked past us. I lifted my right leg and rubbed my thigh against his bulge, massaging it in circles discreetly in the street while the tip of his middle finger dug between my asscheeks and pressed my asshole through my thin pants. It was a turn-on for me, being taken like this, and I felt shivers go down my spine for the second time today.

    "New apartment and two successful dates," I thought to myself on my walk home. "Must be my lucky day."



    The "quick hookup" I had planned for tonight actually turned into a very enjoyable dinner date. I was pleasantly surprised with how things had gone with Dylan. Being a dad, my dating life always had to come second. Now that my son was older... maybe it was time I put myself out there more? And maybe Dylan was the guy I should try it out with.

    I walked back into the apartment, and the sound of the TV from the living room let me know that Rickie was indeed back home from work. By the door, I noticed the mail from this morning, which still hadn't been sorted. I flipped through the letters; a bunch of bills for "Thorne Hall" and a letter from the university for "Broderick Hall."

    "There you go, honey," I walked to the couch to give my son his letter. "Did you have a nice day?"

    "Yeah, better than expected, to be honest," he smiled. "I hung with someone this afternoon and then I went to work. You?"

    I noticed that "hung with someone" was a pretty vague answer, but I always preferred to have my kid come to me with information rather than press for it myself, so I let it slide.

    "Yeah, my day was fine," I said. "Kinda tired now, so I'm gonna go to bed." Just then, I noticed something shiny on my son's ear. "Rickie, what's that?"

    "Oh, I also got my ear pierced this morning? D'you like it?"
    He showed off an earring with a small dangly cross on his right ear. 

    "Yeah, it's nice. Okay, I'm off. Good night, honey."

    "Night, Dad!" my son gave me a kiss on the cheek and reached for his phone, probably texting the "someone" he hung out with this afternoon.

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