Uncle Rocky

    The summer months after my memorable trip to Cape Cod flew by. I worked a summer job at a local quarry, dealing with shirtless landscapers and joining in typical guy talk with the rough and tumble men out in the yard. They shared plenty of stories of their conquests getting women in bed with them; I made up stories of girls I had been with during high school because I was still very much a virgin. The experience with Uncle Rocky opened a whole new world of curiosity and was often the content of many a masturbatory session. I took a liking to longer baths versus showers so I could explore my body, both figuratively and literally. Taking my Uncle’s advice, I explored my ass with my soapy fingers and found different areas of my body with enhanced sensation.

    I was crushingly shy and my anxiety prevented me from having many interactions with other men, falling mute when hit on by a local pizza delivery guy, and shaking uncontrollably when confronted by an older gentleman in the mall parking lot to jump in his car so he could blow me. I resorted to reading gay erotica on my phone or watching clips of older guys fucking younger ones, developing a handy ability to type with my only, non-lubed hand. My hormones ran rampant that summer so I jerked off with any chance I had, during lunch breaks or pretty much any time I took my dick out of my pants.

    It came time to decide between two schools I applied to. My top choice in Philadelphia reached out for a personalized tour to entice me to join their swim team (more on that later). They offered to pay for train tickets from Boston for me and a parent. It was an excuse to take a trip to another city and get wined and dined a bit. While I was packing my suit, some casual clothes, a couple of speedos, and toiletries, I heard my parents having a flustered conversation so I went downstairs. I could tell they were both agitated by the looks on their faces. My father told me that he got an urgent call from his job which required him to leave first thing in the morning and my mother wasn’t able to go because she had my brother to watch. They said I’d have to take the train to Philadelphia alone but much to my surprise, they said my Uncle Rocky was in New York and would meet me there. When I heard the news I tried so hard not to smile ear to ear or bust my nut in my shorts right then and there! I calmingly said it was ok and I was thankful they found a quick replacement.

    I took the train from Boston to Philadelphia, made my way to the hotel lobby and waited for my uncle to meet me there. I watched the door eagerly until he showed up about half an hour later dressed in a suit and apologizing for keeping me waiting. “Sorry bud, took me much longer than expected to get here. Let’s get checked in and figure out what we’re eating tonight”! How could I be mad at this hunk of a man? I just smiled and tried to keep my dick from getting hard in my pants in front of everyone in the lobby. My imagination was running rampant thinking of what trouble we’d get into later. We checked in and went up to the room to relax. It was a really nice room but disappointingly it had two queen size beds instead of a king.  I brushed it off knowing I could still figure some way to work around it. My uncle was preoccupied on the phone with his own job and impatiently said, “Let’s just order some pizza and hang in tonight, you have a big day tomorrow.” That was totally fine with me, thinking it would equate to more time spent with him.

    At around 8pm after dinner, he jumped on his laptop and said “You should shower tonight because we have an early day tomorrow.” I did what he said with a smirk because I knew what was going to happen next. I took a slightly longer than normal shower and kept the door open a bit keeping the invitation open. After about ten minutes of light stroking I heard him come into the bathroom, “C’mon kiddo, wrap it up, I have to shower too” he said as he hung our suits in the bathroom to avoid having to iron them later. I was so disappointed. I finished my shower, threw on some shorts and sat in bed. Rocky dropped down to his underwear, went into the bathroom, closed and locked the door behind him. I was so confused and hoped things would get more exciting once he was done.

    After what seemed like forever, Rocky came out only wearing a robe and sat back into bed and got right back on his laptop. I was waiting for some kind of acknowledgment but he was so engrossed in what he was doing it never came. I took out my phone to keep myself entertained, playing with my dick a little until he said we should sleep. He turned the lights off and I heard him throw his robe on the chair across the room. I didn’t remember him putting on underwear so he must have been in bed naked. I was lying down facing my uncle in his bed but he was turned away from me. I waited patiently for some sign welcoming me into his bed but it never came and my nerves were ramping up, paralyzing me from making a move. Before I knew it, I heard a slight snore from his bed and knew he was out cold for the night. My dick was sore from being so hard in anticipation but it slowly went down and I could feel the coolness from the precum under my foreskin pressing on the sheets as I fell asleep.

    I woke up the next morning to my uncle already half dressed pressuring me to get out of bed and get ready. “C’mon bud. Big day, let’s go” he said shortly. Where was the uncle from a few months ago I thought?! I brushed my teeth, got dressed and we were out the door. We got to the school and an overly enthusiastic student was showing us around despite my disinterest in what they were saying. Finally, we got a break from the student tour guide and I was meeting with the swim coaches who turned out to be brothers, Eric and Tim. Both alumni, Eric, the older of the two and slightly taller, steered the conversation. I could feel them sizing me up, almost beyond what a normal recruiter would but I was still thrown off by the night I had prior that I just shrugged it off. They admitted to watching videos of me dive and how they were both impressed enough to ask me to come to Drexel as soon as possible to start training. It was my top choice but decided to play the game a little saying I couldn’t make that decision until I got home.

    After a long and exhausting day we ate at a nearby restaurant, he stopped into a liquor store, then we went back to the room. We took our shoes off and changed into shorts and t-shirts. My uncle let out a long sigh and said “What a fucking week. Between work and your aunt and I arguing, I’m ready to relax!” It suddenly clicked why he was so distant and preoccupied. He opened the mini fridge and tossed me a beer while cracking open his own and putting away the rest. “Between you and I kid, I bet you’ve had beer already though.” I was trying to man up and lied about having had beer before but kept up with his pace despite adjusting to the flavor. 

    We chatted for a little and after a couple of beers my uncle got up, stripped down and said he was taking a shower before bed. His body was even sexier than I had remembered, having dissociated a little from the shock of our interaction a few months back. His thick dick flopped as walked to the bathroom and closed the door behind him. My dick was getting hard quickly and the two beers I had started to loosen me up. After a few minutes I decided to walk in on my uncle in the shower. 

    I opened the door as he was turning the shower off and he stepped out. “Are you going to hand your uncle a towel or just stand there and stare” he said jokingly. I paused to take in the view of his dick that was more pink and plumped from being soaped up in the shower. I tossed him a towel and he said, “Alright, your turn. Make sure you don’t miss anything.” as he laughed. I was tickled by his comment and stripped in front of him, I had to work my shorts over my boner which he pretended not to notice and passed him to get in the shower. He left the bathroom to get his robe on the chair leaving the bathroom door wide open behind him.

    I took extra care cleaning my rock hard dick and tried to prevent myself from cumming right there in the shower. Using a soapy finger, I played with my ass and eased it past my hole pressing my prostate making a large pearl of precum ooze from the slit of my cock. I was loving how relaxed these few beers made me feel, I didn’t have the usual initial discomfort of putting a finger in my ass. I rinsed off, dried myself quickly, and loosely tied a towel around my waist. I came out to a dimly lit room to see my uncle still in his robe on his phone with that same irritated look on his face as the day before. After sitting down on the edge of his bed, I asked if everything was ok. “Ha. Whatever, it’s fine now” he said and tossed his phone onto the nightstand. His eyes were slightly glazed over from the beers he had and just sat there looking at me for moment. 

“Lie down. Put your head over the foot of the bed” my uncle said. 

    Confused, I did as he told me and laid across the bed with my head just over the foot of the bed wondering what my uncle was thinking. He walked up behind me so he was now upside down in my view. He was swaying a little from his buzz and started to feel the sides of my face with his big hands. Despite being calloused, he held my face gently for a moment before reaching to untie his robe. The sides of his robe fell open to reveal his veiny, uncut, semi hard dick right by the top of my head. He returned both hands to the side of my face and drew in closer and I opened my mouth to take him. He slid the head of his dick into my mouth and I opened as wide as I could. He started to gently rock back and forth, working his cock deeper into mouth getting lubed up with my spit.

    It didn’t take long for him to swell at full mast and start pumping his dick toward the back of my throat. I was trying my best to impress him and not gag; this position was surprisingly easier to take his dick than it was on my knees the first time. My Uncle Rocky pushed past the back of my throat with his slicked dick until I felt the bristles of his hairy balls resting on my nose and forehead. I put my hands up onto his big, hairy thighs to slow him down but he was persistent with his rhythm. My uncle was now fully fucking my throat with his fat dick, I took every opportunity to swallow the extra spit and precum that collected in my mouth. As I adjusted to his face fucking, I used one hand to massage his balls and helped guide him down my throat.

    I would occasionally open my eyes to take in the view of my uncle’s heavy sack and his taint just above my face. His manly aroma was so intoxicating that I began to moan as he pumped my throat. “Good boy” he said with a deepened toned, “Take your uncle’s dick.” Rocky continued thrusting into my throat and after the occasional cough and moments to catch my breath, I used both hands to grab his beefy ass and really start to fuck my throat. Rocky suddenly pulled the length of dick out of my mouth and I gasped for a deep breath of air. I was starting to get dizzy from all the blood rushing to my head.

    He took a couple steps back from the bed and his robe dropped to the floor showing his dick pointing straight out. His forehead had a layer of sweat on it along with his hairy pits from wearing the heavy robe. He reached for the towel that was still wrapped around my waist and threw it to the floor, my dick slapped against my stomach making a splash of precum. He climbed into the bed with his head on a pillow and grabbed his glossy dick, pointing it straight up and said, “Keep going, but I want you to sit on my face.” With a huge smile I shimmied down to get into a 69 position with my uncle. I straddled his chest with my thighs and eagerly took hold of his dick back into my mouth, my fingers barely making it all the way around the girth. I jolted as I felt Rocky pull my hips toward his face only to land on his tongue. This feeling was brand new and felt fucking amazing. He used the broad part of his tongue massaging around my hole and pointing his tongue to press beyond my tight ring of muscle. I moaned and almost whimpered while sucking his dick, sending vibrations through his shaft and making him moan into my ass. We were making the perfect symphony of manly sounds until he pulled me off of his dick.

“Lie on your stomach” he said panting and sweating even more.

    I rearranged myself on the bed with my head on the pillow and my uncle moved quickly to spread my legs and cheeks diving back in to eat my ass. I instinctively arched my back to give him better access and he was going to town, moaning as he was before. I could feel a stream of his spit roll from my ass onto my balls catching the cool air between his heavy breaths. Soon after, he loosened his grip on my cheeks and straightened his body for a full breath before falling on top of me. I was pressed between the bed and my uncle’s sweaty body, both us breathing heavily from the action.

    He started to gently kiss the nape of my neck and explore my body with his big hands. There was a flash of cool air on my back as he peeled his sweaty body from mine only to lay directly on top of me. His hands were wrapped around my wrists pinning them to the bed and I couldn’t move or touch myself. My uncle had his entire weight pressed against me and he slowly started to grind against me. I could feel the head of his cock graze my hole before sliding up between my cheeks. He rocked himself up and down through my cheeks, with each pass pressing ever so slightly more against my ass hole teasing it open. It was torture having my aching cock pressed into the sheets while my uncle was teasing my hole with the head of his cock.

    The room was quiet except for his heavy breathing into my ear and wet noises from his slick dick now oozing precum and my recently eaten ass. With another grind, my uncle’s fat uncut dick found its way through the external boundary of my ass sliding in about half down his shaft making me moan loudly from being penetrated for the first time. I tensed up and tried to ease off of him but I was still stuck from underneath his weight. His sweaty body hair was matted against my back and he entered me another time going a little bit further in. 

“You’re not going anywhere” he said in my ear. “Time for your uncle to take that virgin ass of yours.”

    My heart accelerated partly from anticipation for this moment and from the pain I was experiencing taking my uncle’s hung dick for the first time. This felt nothing like any finger I managed to get into my ass and I felt like I was being split in two. He continued his slow but determined thrusts into my ass until he hit a spot that made me grip anything I could, which was only the sheets. “Relax” he said “You’re taking this dick to the hilt whether you’re ready for it or not”. His tone changed as if he were someone else and I begin to panic; this wasn’t the sensual type of sex I played out over and over in my head.

    My uncle pressed his forearm against my back and went in once more, applying pressure to the same spot that caused me so much discomfort. “You’re only making this harder on yourself, boy” he said. My grip on the sheets loosened and I blew out as much air as I could to relax past this excruciating threshold. I could feel him slip into me deeper, taking his last few inches completely inside me. “Thaaaaat’s it boy.. yeaaaahhh” he groaned.

    My uncle straightened his body taking me along by the waist pulling my ass in the air. There was a slight pause until I heard an audible spat from my uncle dropping a large glob of spit onto the head of his dick that was still partially inside me. He was less forgiving with his next thrust making me yelp, which to him was deserving of hand pressing onto the back of my neck pushing my head into the pillow.  My Uncle Rocky only took his hand off my neck to smack my ass before spreading my cheeks apart, giving him a better view of himself taking his nephew’s virginity.

“You’re going to remember your first time, boy. You hear me?” He said. “YOU HEAR ME?”

“Yes!" I replied loudly, repeating myself with another “yes” but more softly.

    He took one of my arms by the wrist and pinned it behind me as he began driving into me harder. The room was filled with the noise of his hips slapping against the skin of my ass. He was fucking me so hard, I could feel his balls swing forward and hit my own. Despite the pain, my dick maintained it’s hardness, likely from the assault on my prostate. I felt the cool wetness from a string of precum that leaked from my cock slapping my stomach following each of his thrusts. My uncle used his knees to spread my legs even more, lowering his center of gravity and starting to lean back, throwing more force into each of his thrusts. He swore repeatedly and mumbled things I couldn’t understand.

    He pulled out of me quickly and the abrupt feeling of emptiness almost made me pass out. He pushed my hips to the side so I would end up on my back. Without a pause, my legs were up spread and my thighs up against his soaked chest. My Uncle Rocky threw his dick back in me all the way to the hilt. It took several of his pumps to adjust to the new position. He was so fixated on the view of his nephew’s gaping asshole that I think he forgot I was even attached to it. I tried stop him by pressing against his hips but his force overcame whatever strength I had.

    I was lost in all of these new sensations but came back to reality. My uncle came into view as he was wrecking my hole. His entire body was glistening with sweat, drops from his face fell onto my stomach and chest, mixing with my own. We caught eyes and the connection was like nothing I had experienced before. He looked at his dick as it was pumping in and out of me, then back to my eyes. He lifted my hips a little higher and pushed my balls toward my stomach to give me a full view of his dick disappear into my ass leaving only his mound of dark, coarse pubic hair. A devious grin appeared on his face as he continued to drive into me unforgivingly.

    I was overcome with pleasure and the sight of my uncle fucking me like a Neanderthal, my breath got heavier and my ass started to squeeze around my uncle’s beer can dick. I felt electricity through my spine and started to moan loudly, complimenting his thrusts with my own  opposing momentum to receive him. My moans got even louder and it felt like my uncle was so deep inside me that he occupied all of the space within. I started to cum violently from a place I had never cum before. Ropes of cum shot out, the first few hitting my face and the others making their way onto my chest and stomach. It felt like every last drop of semen had left my body.

“Good boy” he growled and only taking his dick out long enough to scoop the majority of the cum off my body and slapping it onto my hole. “What did I say about wasting cum?” He said with a breathy voice and continued fucking me using my cum as lube. “You’re going to take every last drop of your uncle’s cum” he said as his breathing started to pick up. 

    The combination of my now young cum-filled, gaping hole and my uncle’s thrusting made a more hollow slapping sound as he feverishly fucked me. I laid there limp from exhaustion but fixated on my uncle’s face as he started to cum. “FUUUUCK” he yelled in an almost panic-like voice. “FUUUUUUUUUCK” he squealed as forceful jets of my uncle’s cum painted my insides while he continued to fuck my ass as hard as he could. He was filling me up with his warmth and after several minutes, he finally started to slow down. He was panting so hard and wiped the sweat from his head but left his dick inside me, jolting a few times from the post-orgasm hypersensitivity of his cock.

    My ass was still dilated from my uncle’s dick even as he softened and finally pulled out. He looked down watching cum start to leak out, impressed with the mess he made then looked at my face. “Almost missed some” he said as he wiped my face to get my cum that landed there. He then used the same hand to catch the cum dripping from my ass, wiped it all on the head of his dick and aimed it back inside me.

    We both laid there speechless and exhausted, realizing he fucked me well into the night. We didn’t bother to go to our separate beds and fell asleep on the sweat-soaked bed. We eventually made our way under the covers, my uncle spooning me while we slept. I woke up a few hours later to him grinding against my throbbing hole in his sleep, he was fucking insatiable. I reached behind me to put his dick back inside me and went back to sleep.

    We woke up to the phone ringing for our wake-up call and sluggishly made our way out of bed. My uncle’s morning wood was impressive even in spite of the workout he had the night before. He jumped in the shower and within a few minutes called me for to get in. I limped my way to the bathroom and he was already in the other bath robe. “Hurry up kiddo, we got a train to catch” he said, barely acknowledging what we just did. We packed our things and got on the train ride back to Boston. I couldn’t find a comfortable position to sit the entire time but I took it as a badge of honor; taking a dick for the first, and a huge one at that. Uncle Rocky was on his phone most of the way back, not chatting with me much outside of small talk. We got to South Station in Boston where my dad picked us up. My uncle hopped in the front seat. My dad turned around and asked, “How was your big day” he said with a smirk. “Oh, he had a good day” my uncle replied. They both laughed and we drove home.