[Gruntraq] My First Time

[Grunt]

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I got question through Formspring today asking about “my first time with a man”. We all have a first time, and we likely all remember it very well be it good or bad. What is really the “first time” though? Starting at about age 8, I began playing and experimenting with other boys my age with the aid of some of my dad’s porn magazines. We did the normal stuff including comparing dicks, mutual jacking, and even what we called “humping”. So innocent. We would duplicate some of the scenes we saw men and women engaged in the magazines. Luckily I had a couple neighborhood buddies that were also very into it back then before they all got old enough to know better. I never seemed to.

My “first time” in my mind is when I was old enough to cum, feel pleasure and pain, and get off on it with another person. The story is longwinded but hot - to me anyway. And best of all, it’s 100% true. So here it is:

I was 14 and mostly grown physically. I stood 5’-8” and weighed about 175lbs with a decent build from taking a elective weight training class in high school and riding my bike 10-15 miles a day back and forth to school and work. I had short cropped brown hair at the time and a soft peach fuzz mustache. I was not the most popular guy in school but not a complete social tragedy either. I shied away from sports, the “in-crowd” scene, tending to hang out with the geeks and brains - though I was a borderline “C” student.

I was a stoner though and that‘s how I came to lose my butt cherry one day after school at the hands of Derek. He was one year ahead of me, a sophomore. He and I had known each other since grade school, but were never really close pals. He was a jock in every sense of the word. He was on the football team, the basketball team, the softball team, had the Letter jacket. He was one of the most popular guys in the school and one of the biggest partiers.

Derek stood about my height but had a much more pronounced muscular build. At what I figured was about 190 lbs, he had long wavy shoulder length hair, a bushy mustache, and dressed like most of the rock stars popular in the 1980’s. He was a drop dead handsome stud. While he often wore red or black leather zippered pants and a pair of Nike high-tops, most of the time he wore 501’s with a rock band T-Shirt. He was a fighter too, an bully actually. Almost every week he was threatening people, getting in fights in the parking lot, and generally throwing his weight around. He hazed and embarrassed me more than once in front of his jock buds for fun. But when we would be alone he treated me like a friend. It was an odd relationship.

He was outwardly straight as an all American school hero-jock could be. He was well known to be a pussy hound and even at 14 was rumored to have gotten two chicks pregnant. High school rumors are funny like that. I look back in hindsight and just laugh at how things actually turned out. He was indeed was a pussy hound and still is to this day from what I hear. But he has another side.

The day it happened, I was trying so hard to score a bag of weed. I was desperate, asking everyone I knew at school if they knew where I could get some. Between classes I ran in the Derek who was visibly red-eye stoned and reeked of weed. I asked if he could help me score some. He surprised me by saying yes, and we agreed to meet at the bike racks after school. Once we met we rode our bikes to his house and went straight to his bedroom. His younger sister was watching cartoons in the living room and his parents weren’t home. His room was a shrine to the likes of Van Halen, Poison, Ronnie James Dio, and all the other heavy metal Gods of the era. The walls were plastered with posters, pictures, and magazine clips of long haired, muscular, red leather clad rockers from floor to ceiling.

It was a mess of dirty clothes, piles of magazines, sports equipment, and shoes. I had to sift my way through it to sit on his unmade bed. When I finally went to sit down I saw blood stains all over his sheets. Asking him what happened he just said, “I was fucking my girlfriend while she was on the rag”. I’d never seen such a sight before and was a bit put off at first. Derek put a cassette tape in his deck and hit play. Within seconds Van Halen’s 1984 hit “Jump” came over his speakers. “I’ll call my connection and see if he’s got any weed”, he said then left the room, shutting the door behind him.

He was gone for a few minutes giving me plenty of time to take in the masculine musky stench of his filth pit. Dirty underwear and socks laid in a pile against the wall next to his football uniform and pads. It turned me on a little, but at that point the prospect of sex had never even entered my mind. Getting stoned was the only thing I was after. He soon came back and sat on the other end of the bed and grabbed a porn magazine from his night stand. Leaning back against the wall he began flipping through the pages. Wondering about the weed I asked, “So what’s happening with your connection?” He just brushed it off like it was insignificant and said, “He’s not home yet. Let’s just kick back. I’ll try again in a little while.” He then grabbed another magazine and tossed it to me, “Check that out. It’s good shit”. So we sat together on his bed with the blood stained sheets between us flipping through fuck magazines with C and D grade chicks and dudes while Van Halen blasted on the stereo.

Every so often I noticed he was snaking a rub on his cock through his jeans and adjusting himself. He finally broke the ice and leaned over with his magazine and showed me a two page spread of this tattooed chick getting fucked in the asshole by this huge black guy. “Look! She’s getting fucked in the ass and it looks like she really likes it.” He must have had a 10“ dick, her asshole stretched tightly around his shaft with her mouth gaping open. Feeling a little bashful I just and said something to the effect of

“yes she does.” Then he leans in close to me in a slow deliberate voice, “You ever been fucked in the ass?” I was shocked and put on the spot. “No”, I said. “Have you?”. He just nodded. “Naw but I wonder what it would be like. It looks like she is enjoying it”, he said pointing at the two page spread again. I could not have been more shocked. In fact, I cant think of many things since that were that unexpected.

Then he blows my mind for the second time. “Will you fuck me in the butt?” he asked in a craven tone. While I wanted to jump at the chance, it was way awkward for me because this guy was the top jock popular stud at school. I didn’t trust him all that much because he had hazed me in front of other people a few times and really I wasn’t sure if this was some kind of trap. “You want me to fuck you?” I asked. Pulling back a little he said, “I don’t know. I have always wanted to try it. It don’t mean we’re gay or anything. I promise I wont tell anyone”.

I wanted to without any question. This guy had been in my brain a couple times while jacking off. But I could not believe he was actually asking me to fuck him. “Are you sure about this?” I said. “Yeah” he answered. Feeling nervous and like I was really risking everything I said, “Ok.” He then got up off the bed and said he’d be right back. He opened the door and disappeared down the hall, returning with a big tan bottle of Jergens hand lotion. He shut the door and locked it behind him and turned Van Halen up a couple more notches. “Let me see your dick”, he said as he was pulling off his Nike high tops one by one. He then began unbuttoning his pants and sliding them down.

I hastily stood and pulled off my shoes and then pulled my pants and underwear off as he finished. He had a growing bulge in his white briefs that brushed my thigh as I stood close in front of him between his bed and his wall. His hands cupped and clasped my cock as he looked down at it, his quickening breaths puffing in my face. “You have a nice dick”, he said in a sexy voice. Looking down I saw his tenting briefs and grappled him too. I could tell he was big and wanted to see it so I reached into his underwear and grabbed at his meat. He pulled his underwear down as my hands got to it. Damn. He had a good 7” cock, seemingly huge compared to my 6” dick. But what really blew my mind was that it had a distinct curve to the left. He was bent sideways like a banana. Having never seen anything like it, I innocently thought it was because he must jack off with the same hand all the time.

He squirted some of the lotion on his hands and began squeezing and jacking my cock with it. It felt so good to have another guy’s hands around my dick. He then handed me the lotion and told me to do the same to his. The lotion in my palm I wrapped my hand around his thick bent shaft and began pumping it. He was so thick and so curved I was mystified. “Oh that feels so good”, he muttered softly. “Squeeze harder”. We stood there face to face jacking each other softly and slowly for a minute or two as our cocks hardened and slapped occasionally against each other. He wrapped one arm around me and pulled us together, humping his dick into mine.

Finally he said, ‘Can I fuck you up the butt?” While he had originally started this whole thing out by asking me to fuck him, I cautiously said. ‘Yeah. But take it slow. I’ve never done this before.” I was sort of telling the truth. I had played with objects before, but nothing like his monster cock. “Don’t worry, I wont hurt you. Then you can fuck me afterward”, he said. Feeling a wave of energy and anticipation through me I just stood there dumfounded for a minute before he pointed to the bed and said, . “Get on your hands and knees. “. I was creeped out by the blood stained sheets so I asked if could do it on the floor.

“Sure”, he said and grabbed me a pillow from his bed while his other hand jacked his lotioned up cock. Wedging myself in the narrow area between his bed and his wall among the piles of dirty clothes, I got into position. On my knees with his pillow in front of me, my virgin ass was pointed right at him. He got down on his knees behind me and began fingering my hole with lotion. “Spread your cheeks apart for me”, he asked. With my head in his stinky sweaty stained pillow I reached back and pulled my butt wide open for him. “Ummmm”, he grunted as he began finger fucking my hairy asshole. It felt good at first, as he had two slippery fingers gently sliding in and out of me.

He then asked if I was ready and I said yes, “But take it slow”. As he saddled up to me with his hand on my lower back he said, “You have to be quiet though so my sister won’t hear. Stick your face in the pillow if you need to. ” I should have taken that as a warning, but I didn’t really understand what he meant by “if you need to“. I had never been really, really fucked before and didn’t truly know what was coming. And while he had acted like this was his first time experimenting with another guy, I would later come to know he was a veteran butt-fucker who knew very well what he was doing.

As I felt the blunt head of his cock press against my hole I took a deep breath and tensed up in fear. I always knew this day would come. I wanted this day to come. But I was scared to death of it. He had a hard time at first getting his rubbery cock aimed into me, asking me again to spread my cheeks open for him so he could use both hands to guide his dick. My face buried in his rank musky pillow and my hands pulling my lobes wide open, his cock broke through my gate. The sharpest and most intense pain I had ever felt in my life tore through me like a crack of lightning, causing my body to buck away in response. “Uuuhhhhhhoooowww!” I cried into the pillow, my eyes welling instantly with tears. “Shut up!”, Derek growled under his breath. “My sister will hear you!”

“Stop. Stop. Take it out!”, I gritted at him. He pulled back slowly and out of my hole as my body went limp and I let out a breath of relief. While I was catching by breath he squirted more lotion on his hand and fingered my hole again. “Just relax”, he said as he saddled back up to my hole with his hard bent cock. “Take it easy….ohhhh….uhhh….easy!”, I pleaded again as he pushed against my fighting back door. He sunk in again with a single hard shove, sending my body into another shaking sweating tense up. “Uhhhhh Owww….easy man…..take it…..”, I groaned into the pillow again.

With out care for my wanting him to take it easy he began pulling back and shoving in hard and rough repeatedly. It hurt bluntly, a tight pounding, a sharp tearing, and a burning friction. But I took it and didn’t want him to stop. I wanted his fuck. In the initial pain and tenseness, I wondered how long it would take. I wondered if he would cum in my ass. I wondered what would happen if he did. All the while, his painful shocking thrusts pushed my knees across the carpet until my head was against the foot of his nightstand and I was clutching his filthy pillow for dear life.

He was getting dry and I finally asked him to put more lotion on his dick. He pulled out and quickly slathered himself up and pushed back into me. Slippery now more than ever he began a deep and rhythmic bitch fuck that started a loud slapping sound against my ass cheeks. “So this is real fucking”, kept circling in my brain. “I’m really getting fucked”. I wondered if anyone could hear it but as Van Halen continued blasting at volume level 8, I doubted it. He was man fucking me. I was being fucked in the ass by a man. And fuck….it was starting to actually feel good. My dick was asking for my hand. In the rough raw inhumanity of this football jock jack hammering my hole with his dick, I reached under my stomach and began tugging on my cock.

As he pumped my hole raw in burning stretching bleeding and pounding sex I jacked myself to a boil pretty quickly. By now I was softly moaning into the pillow, “Uhhh, ohh, uhhhh”. As I felt ready to fire I squeezed my cock tight and I blew off on the dirty clothes below me. “ I unintentionally moaned out loud, “Ohhh, you get me off. You get me. Oh fuck!” He slapped me on the back of my head and growled, “Shut the fuck up! My sister’l hear you!”. After I came, my body relaxed and seemed to sink to the floor as he continued his anal assault, crawling up on top of my back and grinding in deeper.

He taught me that day what the word “stamina” meant because he seemed to take forever to cum. A few more minutes of his dull sliding pounding tearing pain after I blew off I asked him, “Are you almost done yet?” What can I say, I was young and inexperienced. “Yeah, almost”, he said as he varied his rhythm from fast to slow, then fast again. He would pull out all the way, then slam me hard then follow up with a few fast blasts. I was about to call it quits from the pain and the sore energy of my body trying to resist his fuck. I was sweating and panting. I know now I was in pure ecstasy but didn’t know it then.

Finally he slowed up and grinded deep a few times as I felt his fuck slicken up. He let out a deep sigh as his pump stick stopped pulling and shoving, parking idle in my chute. Derek ‘s body fell limp on my back and he wrapped his arms under me. He squeezed me in tight while his spent cock began to soften inside me. It was the first time I basked in what was the pleasure and intimacy of another sweaty man’s body laying against mine. It was the first time a man came inside me and his seed swam around in my chute. We laid there for a moment and breathed down from the rush before he finally got up off me and began wiping his cock off with a dirty T-shirt.

I sat my leaking ass down on his bed and watched him cleaning the blood, cum and lotion off his dick. He then handed me the soiled shirt and said, “Here you can clean up with this”. It was then I realized I was bleeding and I freaked for a moment. I stood up and wiped my ass with the shirt and looked at it and then to him. It was a little red but not too bad. “Don’t worry it‘s normal the first time. It‘ll heal up fast”. I wasn’t so sure at first but what could I do. Unfazed by it, he began getting dressed again so I did the same. “That was hot. I’ll let you fuck me next time”, he said with a patronizing tone. “Yeah it was. You really got me off man”, was all I could say as well. After we got dressed he said, “Come you gotta go before my dad gets home.”

He walked me out the front door through the living room where his little sister was planted on the couch watching cartoons and talking on the phone. When we got out to the front yard I asked, “What about getting the weed”. It seemed like had been forgotten. “We’ll have to do that some other time. I have to get to football practice now,” he said bluntly without a care. “See you around. And thanks again”, he said and headed back into his house. Feeling a little used at this point I grabbed my bike and felt wave of sharp pain as I set my torn open hole on the bike seat.

While I felt used and maybe even a little made, I wanted to do it again. I wanted to fuck him and have him fuck me again. My hole was so pounded open it still felt like he was in me as I rode my bike. On the five mile ride home l felt like a new person, like I had transcended some kind of level in life. I was no longer a virgin and next time I would get to do the same thing to him. Totally tubular! (1980’s slang)

We got together many times over the next few years and yes, I fucked his hole plenty too and we did even more. Every time we had sex it was a story to tell and I will share some of them here as time goes on. We lost touch for a lot of good reasons. And while I know where he is today, and he knows where I am today neither one of us has chosen to chase the other down. That actually might be best, but part of me would not mind hooking up with my first man one more time some day just for fun.

One thing I can leave you with is the fact that the smell of that Jergens lotion to this day flashes me back to that day, getting bull-fucked on the floor of my football jock’s filthy bedroom. WoOF.

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[MAIKOL20]

Pretty good and hot experience man! Thanks for sharing.