A gay story: Jason… My First Some of the events in this story are happening now. Some happened long ago. The latter are why I am doing this. I wish for you to join me in my erotic reminiscence of my first time with another man. His name is Jason, and Jason is the reason I am telling you this story from my hands and knees. Jason is the reason I need this ridiculously large plug locked firmly in my ass. Jason is the reason I am yearning.
You see, as long as I can remember, Jason and I were childhood friends. By the time we were seniors in high school, we had slept with more girls than a high school kid should. Since his parents were never home, we stayed at his place nearly every weekend. It was here we threw parties, took turns having sexual rendezvous, and even on one occasion shared this one notorious slut. It was during these occasions I had caught more than just a glimpse of Jason’s dick, just as I am sure he had mine. He was no slouch, and I used to envy the way he could fuck that little slut with his massiveness. I was always impressed that a girl her age could take it all. I soon found out maybe I wasn’t just impressed, but rather envious of her.
Just thinking about what happened next has me so hot right now. Unfortunately the countless sessions of self-pleasure such as this have never compared to that first night. Sure this butt plug is huge… far bigger than Jason’s dick in fact; but nothing compares. My stiff cock is beginning to ooze at the thought of him coming up behind me and replacing this piece of rubber with his heavy nine inches. I bet he could start fucking me as hard as he could right now as long as this thing has been inside me. The way that cock could hit all the right spots would just make my dick explode right now!
I remember the night everything changed. It was a slow night, snow was falling, and we were home alone. Jason began watching some porn on his laptop while we listened to music and had a few beers. What had started as an innocent try at humor would soon create a sexually charged environment. I moved next to Jason so I could see what he was watching. There was a girl getting her ass destroyed by a large black man. He would pound her and pull his cock out to leave her asshole gaping wide. It was hot as hell, and Jason was not hiding his massive erection. After noticing, I let my inhibitions down a bit too. The next words out of his mouth changed my entire life.
“Have you ever thought about fucking another man?” Jason said without hesitation. “I do, all the time,” he continued. The lump in my throat seemed impossible to swallow, but the truth was… I had! I always had! In fact, I had spent countless nights imagining what it would be like to be treated like that little slut Jason used to dominate.
“I’ve thought about us fucking… sure.” I tried to utter calmly. My nerves were shot, but the smile that came across his face immediately showed me that was the answer he was looking for. He leaned over, put the laptop aside, and kissed me passionately. I had never kissed a man, and I’m still not sure I like it, but at that time it helped me ease in to the situation.
These thoughts are so vivid to me now. My cock is beginning to swell even more now, and there is a distinct puddle on the ground below. I suspect it will only continue to grow, but for now I’m going to have to put it to good use while it’s still warm. I am leaning back on just my knees and forcing this obstruction loose. As the widest part struggles to free itself from my hole, it practically steals my breath. With the plug out, I use my hand to gather the fresh cum and crawl back to my knees and elbows. With no plug to fill me, my ass is open wide on its own. I am letting the cum pour down my open hole, meanwhile I am using four fingers to make sure it’s all in. I reinsert the tip of the huge plug and begin to put steady pressure. As it approaches the widest part again, I can feel the fresh juices inside my ass begin to help it along. SNAP! All the way in again, I continue.
As we kiss, I let my hands wander to Jason’s throbbing cock. I slide it in his shorts and am awe-struck at its size. It feels much larger than it looks. He assists me by sliding down his shorts. As it springs free, I waste no time pulling away from his face so I can get a good look. Almost instinctively, I lean down to take it in my mouth. I begin sucking to the best of my ability. There is spit everywhere as I try to take him deep in my throat. My inexperience limits me, so I simultaneously stroke his cock with my hand as I suck. I occasionally take his balls in my mouth one at a time to give myself a breather. At times he seems to be on the verge of cumming, but he stops me every time he gets close.
“I don’t want it in your mouth,” he said firmly. “Let’s get these pants off, I want to see that tight ass beg.”
At this point in the story, I need something in my mouth NOW! I lean back again to remove the plug from my ass. Again, it’s size makes me shiver as it pops free. I have a large dildo to lube up and to replace the plug. I stick it upright on the floor and hover over it. As I slowly jack my own dick, I lower myself onto the fake cock. Once it’s in, I begin to ride it nice and steady. It is in perfect position to nail my prostate with every thrust. I mustn’t get too worked up… there’s more to this story. So I pull all the way off the dildo, my asshole aching for something else, I replace it with the plug again. Meanwhile, I begin to suck the dildo that I just pulled from my ass. I can taste my cum from earlier and combined with the feeling of being filled from both sides, my cock is throbbing more and oozing twice as much.
Jason positioned me on my back on the couch. Placing my legs over his shoulders, he began licking my asshole without hesitation. Occasionally he would take my cock into his mouth and suck it like an old pro. The last time, I hardly noticed he had obtained a bottle of lube and was now coating my hole and beginning to work his fingers in.
“I need you to fuck me now!” I demanded. He smiled and rose to his knees. With my exposed hole warmed up, he applied the leftover lube to his big cock. He aligned himself and began to push his meat steadily in. It took several minutes, but once he was all the way in the pain turned into pure pleasure. Working up his speed, it wasn’t long before my asshole was taking his wide cock to the hilt. Eventually he was pounding me as he pressed my knees all the way to my head. I was stroking my own cock at this point, as I was completely overcome by primal instincts. He pulled his cock out to leave my asshole stretched as wide as he is. He paused for a moment to lick my gaping hole and then reinserted all 9 inches.
At this point I am so worked up, I have to roll to my back. I am stroking my cock at full speed now, and grinding my ass down hard on the plug. I can feel myself beginning to approach climax, so I roll over to the position Jason was fucking me so nicely in. I now have my legs over my head in the “pile-driver” position to give myself a great view of my cock. Meanwhile, the plug tries to bury itself deeper into my guts as I loosen up.
Jason’s cock is now pounding towards the end, and I cannot contain myself any longer. I begin stroking hard, and just as Jason thrusts one last time, I explode all over my chest and face. My orgasm is intensified by the feeling of his hot seed filling my deep hole.
As I remember the way those final moments felt, I begin firing hot streams of cum into my own mouth. As I simultaneously pull the plug from my ass, the thickness forces far more cum that I expect. I eagerly swallow my load as I dream of what it felt like as he pulled his softening cock from my hole.
As he pulled himself out, I began to lower my legs. I could feel his juices beginning to ooze from my effortlessly open hole. He didn’t waste the opportunity to put his mouth to my hole and eagerly take his cum into his mouth. He generously shared his deposit with me in one last passionate kiss. While I was left to enjoy his gift, he cleaned up the mess I had left on my chest with his tongue. We collapsed in a sweaty mess of sex and just held each other. He spooned me from behind so that I couldn’t forget the feeling of his manhood in my presence.
As I lay here exhausted, I can’t help but think it’s been far too long since we’ve been together. There were many more times with him, and many more times with other men. I can’t wait to share those stories with you soon!
THE END