14 comments/ 191725 views/ 48 favorites Curious with the Gay Kid By: taleteller I was one of the normal kids. I played football, dated one of the cheerleaders, had friends, went to parties, and picked on the gay kid, Rich. Like every school, ours had the one gay kid that everyone knew about. He had been caught freshmen year making out with another guy, who ended up moving. People took every opportunity to torture him, including myself. I considered myself to be straight, and had a good sex life with my girlfriend. But, as I was about half way through my senior year, I became curious about how it felt to be on the taking end of sex. I would often tease or even finger my ass while masturbating because I enjoyed the new sensations. I often looked at Rich, the gay kid, and wondered if he had ever been fucked in the ass, wanting to ask him what it was like. I caught myself staring at him in the classes we had together. Even more surprising to me was how often I caught myself looking at his crotch. It seemed like every time I looked at him, he had a hardon, and a big one at that. I always wondered just how big he was. He was not allowed to shower with the rest of the guys after gym, and walking up and asking just wasn't an option. One day however, everything took a turn for the best. One night I wandered into the movie store, I had just turned 18 and was planning on renting a porno. When I walked in, the first person I noticed was Rich, looking at some older movies. I was feeling daring and went out on a limb. I approached him, and he tried to avoid me. I finally caught him and said "Hi." I made some small chat, asked him what movie he was getting, just bullshittin' for a while. Then I dove in and asked him if he wanted to come over to my house and watch the movie, my parents were out of town and it was a perfect opportunity for me. After some convincing that it wasn't a plan to hurt him or anything, he agreed to come over. We went back to my house and straight to the basement. We watched the movie, "Oceans 11," very good by the way, then came the awkward silence after we turned off the TV. I went straight for the throat, "Rich, have you ever been fucked?" He immediately thought I was only poking fun at him, but he eventually loosened up. "No, I'm a gay top, I do the fucking," he answered. "Have you ever fucked a guy?" I asked. "No," he responded again "My boyfriend never let me." "Well how would you like to try it for once?" I asked him. He thought again it was some kind of trick and even tried to leave for a moment. I convinced him I wasn't joking, I told him how I had looked around online, and was kind of curious about being fucked. He shifted uncomfortably then asked exactly what I was thinking. "You want to fuck, you're gay, I want to try being fucked, I'm straight. I'm the one with the problem. And the solution is that you could fuck me. But, you can't tell anybody what we do, and as long as you keep quiet, and I like it, we can do it as long as we want." I watched him think for a minute, trying to figure out if I was telling the truth. "OK," he responded, "I'm up for it." I glanced instinctively at his crotch, the slender pole along his thigh told me he was indeed "up" for it. "Just remember," I said, "don't tell anybody, or I'll deny it, and nobody will believe you." "OK," he responded, looking somewhat excited for this opportunity. At this point I told him to go ahead and undress while I ran to get a few things. I came back downstairs with a towel, some lube, and a condom. I looked over and saw Rich standing there in only his underwear, he was a tighty-whity guy. He had a somewhat muscular build and was quite tan, especially for winter. Then there was his crotch; I could clearly see the outline of his boner forced into a bend to one side. I sized him to be about 8," just and inch more than me, and I had always felt like I was well sized. He saw me staring and I had to cover my gay moment, "I'm not giving you head or anything, I'm not gay." "OK" he answered. I walked over and put down the towels while Rich watched anxiously. I then stripped down myself, trying to flex a little to show off. Then we were both just standing in our underwear, I'm a boxer man. "OK, here we go," was all I could think to say, I yanked down my boxers and let my semi-erect cock hang between my legs. I could have sworn I saw his hardon jump a little at the view of me. It was his turn; I felt oddly excited and tried my best to conceal it. He leaned forward and yanked down the tighties. When he stood back up, my jaw dropped. I had been right-he had a full eight inches. But I had also been wrong, the eight inch cock in front of me was completely soft. I again covered myself "You should go ahead and get a boner" I said trying to keep my voice normal. I looked at the condom in my hand, which was bought for my size, and threw it aside. I watched as he stroked the big dick in front of me. As it grew I tried to size it up, about ten inches already, I thought. "OK that's good, let's get to work." I got to my hands and knees on the towels, the image of his big dick in my head, and spread the lube around my asshole. "Put some on your cock too," I told him. He did as he was told then stood frozen in place. I placed my hands firmly and told him to go ahead, but to take it easy at first. I clenched my fists and closed my eyes, which made me repeat the first view I had gotten of his massive dick. Then I felt it, the enormous head press against my asshole, I did my best to loosen my muscles, but the idea of being penetrated had them excited. The big head felt like it was three inches thick, with the shaft being about an inch slimmer, and rock hard. I felt the head press harder against my ass, with no luck. "Come on you pussy" I said to him, wishing I hadn't shortly after. He did press harder, too hard. The massive head popped in, and thanks to his thrust to gain entry, so did three inches of his cock. "HOLY SHIT," I yelled aloud, "Don't move." My ass was now on fire, I had never had anything that big in my ass. I felt myself adjusting slowly and told him to go ahead again. He pulled back to only the head was in me then thrusted again, repeating the process a few times. I gritted my teeth through the pain, feeling some pleasure start to rise deep in me. After a couple of minutes my ass had loosened to the thickness, and I was now enjoying it. Being fucked felt better than I had imagined it would. "How much is in?" I asked, thinking it should be almost fully in. He paused for a moment when in deep thrust and measured with his eyes. "About eight inches," he answered from behind me. I knew at this point that his cock had still been growing while he fucked me, I could feel the extra length being added. "How much more?" I asked. "About four inches to go," he answered. "Wow," I thought to myself. I had never imagined I would experience a real foot long cock, something some considered a myth. I again gritted my teeth as his fucking started to speed up, and it started to hurt slightly from the added girth towards the base, but I didn't mind. I could feel his massive pole pushing some of my insides around, which felt good, and painful at the same time. Then I felt it, his balls slapped mine. He now started to pull back and drive in about eight inches of his cock, being somewhat rough and enjoying being in control for once. He seemed to be using this chance to get back for years of torture, and relieve built up stress. His more powerful thrusts meant more pleasure for me. I had gotten a boner that was now throbbing, wanting to cum. I let go and came all over the towel and let my dick get soft again as Rich fucked on. Then he pulled his cock almost all out of my ass, only letting the head pull back against my hole, only to slam it fully back in, causing me to moan loudly and arch my back, making me feel like a slut. He held still with his cock balls deep inside, then I felt it, his cock started to swell. I looked a couple feet to my left and saw the condom I had brought down with me and forgotten about. Then with a moan, he burst. I was being filled with what felt like gallons of hot cum. I had not planned on him cumming in me, but was enjoying it anyway. Each gushing shot felt like a full load from me, I counted about five strong shots then. I felt the spurts come to an end and he pulled his cock out, causing a slight pain as the thick head popped back out. I reached back and felt my ass, I had a gaping hole, something I hadn't thought about. I got to my feet with shaky knees and felt the cum rush out of my ass and down my legs. I looked at Rich, his cock now soft but retaining most of is size, down to about 11 inches and covered in his cum. I couldn't believe I had just taken that monster all the way inside me. I offered him a towel and he cleaned himself up and got dressed. Not taking time to properly put himself away, he left his now ten-inch cock hanging out the left of his underwear. "Well, I guess you better leave now. I'll talk to you at school on Monday." He said goodbye, and left. I went up to the bathroom to take a shower, where I easily slid three fingers into my gaping ass, and came harder than ever. Curious with the Gay Kid Ch. 02 It had been a couple months since Rich and I had first started meeting. By now we had our ritualistic Saturday nights down to art. We would meet up just before the movie store would close and pick out a movie to watch, and continue back to my house. We would watch the movie and proceed to have sex. As time went on, I found that I needed less and less lube and the initial entry no longer hurt as bad. I also noticed that Rich was starting to cum more than before, which he explained was the result of him jacking off little or not at all anymore. Sadly, I also discovered that I had not conquered a foot-long mythical cock, but a simple eleven and a half incher. After our first couple of encounters, Rich started to just spend the night at my house to ensure we were able to take as much time as we wanted. I had promised myself that I wouldn't get to be friends with Rich, but I had failed. We began to talk when he was over, and I learned a lot about him. He told me how he lived with his father and stepmother; both of whom he loved, and had never lived with his real mother. I learned that he had lived a quite sheltered life with his fairly wealthy parents. He also explained to me that he was not in fact gay, but bisexual. Of course, nobody would believe him when he explained because he happened to be caught with a guy first. This revelation stuck in my mind for quite some time. The good news was that nobody noticed anything different about me, almost. My girlfriend, Courtney, had mentioned one night that I didn't seem to be as horny and wanting to have sex as often, but when we did sleep together, it seemed better. The two seemed to balance out and explain each other. The truth was that lately I had been imagining what it would be like if Rich were to join in with me and Courtney, and it seemed to make sex even hotter, not that I needed to imagine anything when I was with Courtney. We had met during our sophomore year, when she had been somewhat nerdy. She had been a bony little thing, but I always thought she was cute. We started dating that year and had been together since then. It was not until our senior year that we started sleeping together, and that was because I couldn't help it any longer. Over the last couple years, Courtney had filled out very nicely. Her cute face and become fuller and less bony. She had gotten beautiful curves around her still thin belly and slightly wider hips. Her small B cups and filled out to good sized D's, and she had a round, firm ass that no amount of surgery our working out could ever create. She had gone from being the nerdy little girl to the object of every guy's lust, and I had her. I occasionally had brought up the idea of a threesome with her, and she seemed kind of interested. Courtney had always been willing to experiment with different things, just another thing I loved about her. I decided that Christmas break would be the perfect time to put my plan into action. I knew that over the weekend my parents would be visiting family across the country, something I was not fond of and was allowed to stay home for. I talked to Rich and he agreed without hesitating. I figured it might take a little more effort to get Courtney in on the plan, so I decided to wait until that night and put her on the spot. I just told her she could come over and spend the weekend with me. She agreed. The weekend finally arrived and we spent a nice relaxing afternoon together. That evening we had dinner and proceeded to the basement for a movie. As we watched the movie, all I could think about was what I knew would happen tonight. We began to make out and were all over each other, and stripped each other down to our underwear. Just as I pulled off Courtney's bra and began to rub those amazing tits, I heard the door open to the basement. I looked at the clock, ten o'clock, right on time. Courtney quickly covered herself with a blanket when she saw Rich, then looked at me. I spent the next few minutes explaining the events of the past few months. She put her face in her hands for a minute, I looked at Rich and he looked as anxious as I felt. As Courtney looked up from her hands, Rich and I held our breath. "I guess I'm willing to try anything once," she finally said, as Rich and I both sighed out of relief. I told Rich to go ahead and undress as Courtney and I resumed our making out. She seemed to be more aggressive and turned on now than she had been earlier. I glanced out the corner of my eye to see Rich stripping down, I hadn't mentioned Rich's endowment and couldn't wait to see her face. She felt me getting a hard on and used one of her hands to pull my shorts down and give it some attention. I noticed that Rich had now stripped down to his boxers and was looking uncomfortable. "Don't forget to take care of our guest," I reminded her. She got off of me and dropped the blanket she had been holding, her perfect tits hanging right in front of my face. She turned to Rich and gasped a little. He was standing there with his ten-inch semi-erect cock hanging out the bottom of his boxers. She turned to me looking confused, scared, and turned on. "Go ahead, you'll love it," I encouraged her. She turned back and walked over to Rich, while I stared at her amazing ass bounce away, barely covered at all by a hot pink thong. I had been telling the truth when I told her that she would like it. Rich was not too much thicker than me, so I knew it wouldn't hurt her and she would be able to enjoy deeper penetration, and I nice big load blown in her. I would have worried about condoms but I knew that she had been on the pill for a couple weeks. I pulled off my boxers as I watched Courtney do the same with Rich's. I watched her play with the huge cock like some strange toy, and then slowly pulled it to her mouth. The big cock filled her mouth easily and she began to lick and suck on it, something I knew she did very well. I sat on the sofa and stroked my own throbbing cock as I watched my girlfriend suck that huge dick until I couldn't wait any longer. I walked over to them and knelt down behind Courtney. I reached down and easily tore thong and tossed it aside. I got right up behind her and spread her firm ass cheeks apart and pressed my pre-cum covered head between them. I head her moan through Rich's big cock as I slipped my cock head into her ass. I only had enough leverage to slide a couple inches inside of her, so I rocked us backwards together. As Rich's throbbing purple cock head slide out of Courtney's mouth I realized his dick seemed much bigger at eye level. We hit the floor with Courtney laying on me, and causing my dick to almost fully penetrate her tight ass, she moaned loudly, turning me on so much. I grabbed her legs and pulled them to just about a foot above her shoulders and spreading them slightly, years of gymnastics and cheerleading made this possible. I saw Rich's cock twitch a little at the sight of Courtney's tight wet pussy, probably the first he had seen in person. He stepped forward and got down to his knees and guided his massive purple head to her waiting slit. He pressed hard enough to push the head in at the same time I thrust forward, the result was a half moan, half yell, and entirely pleasured noise. Rich and I started a quick rhythm, thrusting in and out in turn. I could feel the added pressure of his dick moving in and out along with mine, and it was amazing. Courtney lay there doing her best to keep her breath between moans and orgasms. I could feel myself coming close to cumming as I watched her amazing tits dance around on her chest. Then I felt Rich thrust in hard and hold, I knew what was about to happen. Rich and Courtney both moaned as he released the biggest load he had ever blown, according to him. Two minutes later he pulled his still hard cock out of Courtney and stepped back. "My turn," I said as I lifted her to her feet and I joined her. I bent her over the back of the sofa and got my position behind her. I lifted my throbbing cock to her wet pussy, which had already started to close back up. I applied a little pressure and my cock slipped in, instantly being covered by the gallons of Rich's cum in her. I began a strong rhythmic thrust making her moan with the same rhythm. I felt a cum covered cock head press against my ass and I held still for a moment. A quick thrust dug his lubed cock a couple inches into me. I let out a moan, out of pleasure more than pain. Rich began his thrusts, pushing me fully into Courtney on each one. I simply stood there as Rich did the fucking for both of us, and felt myself so close to cumming. Then I felt Courtney go into a strong orgasm, setting me over the edge as I blew a big load deep inside her. The tensing of my muscles set Rich off behind me, blowing his second massive load of the night deep in me this time. Rich pulled out behind me and grabbed a towel from our stash behind the sofa and began to clean himself up. I pulled my own dick out of Courtney to allow a small river of cum flow down her leg. I turned her around as she panted and kissed her deeply. "I told you that you would enjoy it," I whispered. I gently laid her down on the floor and covered her with the blanket up to her chest, I loved watching her tits jiggle slightly as she slept, and she was out quickly. Rich and I finished getting cleaned up and redressed, sat down, and finished the movie.