The story below is based on my actual first time. It happened about five years ago, and to this day I look back on it with fond memories.
All standard disclaimers apply. All characters in the following story (and its subsequent chapters) are entirely fictional. Any resemblance to real people is entirely coincidental. The author does not condone the actions in the following story. There is a strict line between fantasy and reality, and, under no circumstances, should adults and minors have sexual activity in real life. In real life, no one under the age of eighteen (in fact, very few people under the age of twenty-one, in the author's opinion), should be having sex, because they are not mature enough.
The following story (and its subsequent chapters) contain gay sex, sex between adults and minors, oral sex, anal sex, anal-oral contact (rimming), urination (watersports), interracial sex, group sex, and others. if any of this offends you, please press the back button on your browser now.
Under no circumstances should this story (or its subsequent chapters) be published on any websites without the author's explicit consent. If you wish to contact me, please do so at MrPerfect @ gmail.com (just remove the spaces). I'd be happy to hear from you.
Copyright 2012 Mr Perfect. All Rights Reserved.
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So, without further ado, let the sex BEGIN!
Often, I look back on this moment in my life and think to myself, "Wow. This is what started it all. All of my sexual conquests began with this one boy. A dumb football jock." At the time, I was 15, and he was 17. He was tall, darkened by the sun, but his green eyes were bright.
His name was Richie. Richie had been dating a girl for about 2 years. She wasn't very pretty. She was rather short, and, in fact, had braces that hindered her ability to adequately give a blowjob. We had spoken about this from time to time, and spoken about his sexual behaviors with her. Apparently, they were, "really in love." Well that would explain why he cheated on her, right? Actually, that's not fair. He did love her. But like so many movies and books have taught us, everyone has their price.
Richie was poor. His family was in trouble financially, barely able to feed all of his siblings. I didn't particularly care because my feelings for him stopped at his crotch. For months I had begged him to have sex with me. I begged him for, "just a little bit." One would think that a heterosexual man, like he was, would be instantly turned off and run away... But he didn't. So really, was it wrong of me to slowly push the envelope? I don't think so. He was the one who kept bringing her' up, and her inadequacies.'
For fifty dollars and a hot meal, Richie agreed to have sex with me. Since he did not have a car, and his parents could never find out, I paid for his taxi over to my house (at that time my mom was working almost constantly and my house was empty).
I informed him to arrive a block or two away so that none of my nosy neighbors would notice. The cab pulled up, I tossed down five dollars, and we set off walking. I walked ten feet or so ahead of him out of pure shame. I felt so ugly around him. My skin itself felt like it deserved to be ripped off and fed to a pack of rats. The whole time I could feel him watching my ass I walked. Not the watching that happens when a guy sees a girl with a nice ass, the kind that happens when you're waiting to see if someone will pull a gun on you.
The kind that happens out of fear.
He sat down on my couch, glad to be out of the hot sun. Oh no, I don't mind if you T.V. first, go right ahead. You're right; it would help to calm your nerves. To be honest, my nerves needed to calm down too. So for a half of an hour we watched Max Keebler's Big Move. When the credits started to roll, my hand was on his lap. He nodded.
I dropped to my knees and pulled down his shorts... He still wore briefs. I was surprised at how large his penis had become. Apparently he was at least a little excited. It tasted funny.
For five minutes I did my best to please him: licking, sucking, nuzzling, going deeper and deeper. After asking if it was feeling good, I was told I talk too much. Then my jaw started to hurt, and I just really was getting bored. Let's be honest, a sore jaw isn't worth fifty bucks. He was ready. Oh no, I've got lube, I'll go get it. He said to hurry as he watched me rush up the steps to my parents stash.
At this point, time seemed to freeze for a second. I had seen him naked, but he had not seen me. And I like it that way. So I pulled down my shorts, but left them on for a quick escape. HE told me to bend over, and I did... "Further," he said pushing my back down, putting my face in the seat of the couch. I felt his hand glide along my ass; it was cool to the touch.
What happened next has brought me tears during the late night hours. Without any hesitation, he rammed his penis inside of my fat ass. In my head, I picture a wolf piercing a lick slab of meat that has no hole. And he kept it in there, leaning down on me, enjoying my squirms.
"No, no get up! Get up! Shit!" I say finally pushing him off me. I sat there taking deep breaths, feeling sick to my stomach. He was like a dog excited to go on a walk, wagging his tail and panting. "Ok, I'm ready. But go slow this time!"
"I promise," was his only response.
For ten minutes he ruthlessly pounded on top of me. I felt completely disconnected from the experience. The only thing that kept me in the moment was his smell. He smelt of an old cologne that my uncle use to use. My uncle was a godly man, always going to church, read his bible, and had all of his children baptized. It's ironic that the man now fucking me smelled exactly like my first crush: Uncle Dovel.
Then I smelled something odd... Oh no. It's me.
"Wait," I said, bringing my head up from the couch, "I have to go pee." I climbed upstairs to the bathroom and washed off myself. I'd like to not go into full details about what exactly I was washing off.
As I came back down stairs, he was pacing, apparently excited about what was going on. He told me I was to lay down on my back with my legs in the air. His eyes were serious and cold. I obliged, happy to be pleasing him.
I lie there with my arms to my side, hoping to just please him, that's all I wanted at this point. He was close to me, and his breath was warm against my neck. I think he could tell I was uncomfortable, because he took my hand and put it on his back. I felt his muscles tensing and releasing as he pumped into me. Then I put another hand on his back. Wow, this started to feel really good. I stopped feeling self-conscious about myself and started to enjoy myself.
I felt him hit my prostat and I instantly started moaning his name. I wrapped my legs around his body and gave into him completely. He was going deeper and deepr into my asshole. Occasionally he would slip out, but would then grab his shaft, and ram it in even harder the next time.
I was in heaven.
Then he started to grunt, and breath heavier; I knew he was close to cumming. I was worried that I might not cum, so I started bucking myself against his dick, holding onto hope.
"I'm gonna cum," he said not looking at me. No! I started scratching his back, hoping to slow him down. He thrust three more times, and then he was lodged deep inside me. With a deep sigh, he let loose his load inside me. He pulled out of me, stood up, and wiped of his glasses. I was laying there on my back with a rock hard dick wanting to be relieved he wiped the sweat off his brow and made his way upstairs to the bathroom.
Instead of acknowledging what had happened, I just lay there, counting the tiles. He came back down, and I rolled over on my side, now facing the back of the couch. He slapped my exposed ass, laughing as he did. I looked over at him.
"Enjoy it?" I asked.
"Yeah," he said, "yeah I did actually." He sat down be side me, and put a finger in my ass. It felt nice to have something in there again. I felt very empty at this point. "You didn't cum."
"Well," I replied, "there's still time until you have to go to practice?" By the way, he plays football. Linebacker.
"Okay... What now?"
"Do you trust me?" I asked
"Yes."
I told him to bend over with his ass in the air. He told me that he didn't want to be penetrated, as if I was trying to fuck him. No, but what I did do I knew would drive him crazy. I closed his legs and pulled his cock through his hairy thighs, giving it a lick. He smiled. I pulled apart his ass cheeks and stared at the pink hole. It was perfect. There was a few hairs around it, but his cheeks felt like warm melons in my hands.
I leaned my face forward and looked right in his eyes as I took the first lick. He looked like a scared dog. But after feeling my tongue on him, his cock instantly twitched. So I licked again.
"Well?" I asked, hoping he'd like it.
"Don't stop now," he said turning away from me, pushing his ass in my face.
I dove into his ass, licking and sucking away at his hole. I could tell he liked it, because as I was licking, I was jerking off his hard cock. I had no more insecurities, and in fact, I felt confident. So without asking, I stuck licked my index finger, and inserted it into his hole.
"Whoa," he said. I slapped his ass with my other hand, making sure he new I was taking control now. "Uhh... Just go slow." So I took out my finger and put it up to his face. He tried to turn away from me, but I smacked his ass again. He looked at me, afraid.
"Open your mouth."
From then on, I was in charge. Slowly putting two, then three fingers in his ass. He came two more times. The first time, he was afraid to enjoy it, barely whimpering. The second time though, he was ramming his ass back on my fingers. He was actually spreading his cheeks for me too!
Then his cell phone rang, it was his coach.
"Yeah, I know," he said trying to sound normal. But how can you sound normal with a tongue up your ass? "I know, I'm just, uhhh," he looked back at me, "A little busy right now... Yes, I know... Okay, I'll hurry... No, I don't wanna be kicked off the team... Yea coach I know..." Seeing this as an opportunity, I took out my cock, put hoping his ass was lubed up enough, I pierced him. "Yeah coach... FUCK!"
"Quiet now, you don't want coach to hear you," I said smiling.
"... No, I just... Just... Stubbed my toe coach. Sorry."
"Good boy," I said pounding his tight ass.
"Ok, I'm leaving now coach... Yeah, bye."
"You're not leaving yet, not until I'm down." He gripped onto the couch and started to tear up. I didn't last long because the sight in front of me was too hot to handle. Here was this linebacker who had fucked me and bred my asshole like a dirty whore, and I was in turn pound his virgin hole.
I pushed one last time inside of him, and I felt my cum release. I slapped him on the ass just like he had me, and I walked away. I walked into the kitchen, getting a glass off water.
"Okay, I'm gonna head out," he said, holding up his clothes in his muscled arms.
"You're money is on the table," I replied. I didn't look at him, only washed out my glass. I heard him walk away and out of my house. I heard the door close, and then the house was silent. I walked back into the living room to watch him leave, but as I passed the dining room table, I saw all the money still there.
He'd be back.