5 comments/ 84169 views/ 11 favorites First Gay Sex By: JJCavan My first experience with gay sex was back during the summer after my freshman year of college. There was a group of friends who hung out together -- a fairly even mix of guys and girls. But I was closest friends with two; Becky and Rob. It was something of an odd relationship. We were all the same age, 19 at the time. I can't really say Rob was my "best friend", though I hung out with him more than with any of the other guys in the group. Nor can I say I was really "dating" Becky, regardless of the fact that we went out together on a regular basis. I knew that Rob was just as interested in her as I, but it didn't really matter; we were all just good friends. The three of us spent a lot of time together. Rob's parents were pretty well off and had a big house in the nicer part of the small town in which we lived. So it was no surprise we most often ended up loafing around in their basement game room, shooting pool, listening to music and wasting time as teenagers are wont to do. One evening, during summer break, Rob's parents weren't home, so he, Becky and I had the place to ourselves. After a few games of three player 8-ball, we sat down on the big sofa in the game room, with Becky between Rob and me. I'm not sure which of us started it, but soon we were sort of passing a kiss back and forth. I'd kiss her, she'd turn to Rob and kiss him, then back to me and so it went. Of course, the hormones started to flow, and soon Rob reached over and unbuttoned the top fastener on her blouse. She laughed and said it wasn't fair, since he was wearing a t-shirt. So, I unfastened the next button. She turned back to me and gave me a hard, deep kiss while unbuttoning the top two of my shirt. And so it went until her blouse was unbuttoned to the waist, and we could see her white lace bra and the swell of her breasts. I had an erection fit to tear through my jeans as I slipped my hand into her shirt to caress her chest, while Rob unfastened the top button of her jeans. At that point, Becky let out a half chuckle and said, "I'm not sure the two of you can handle me," while she reached out to play with our denim covered erections. "I'm not sure the two of you could handle me," was Rob's reply. After another few strokes of our engorged members, Becky laughed again, and got up suddenly saying "That's all for tonight, guys." She slowly buttoned her jeans and blouse, and then leaned in to kiss first me, then Rob. A little while later, we left. As I walked her home, she held my hand but playfully refused to talk about what had just happened. It wasn't until later that what Rob said struck me... "I'm not sure the two of you could handle me." I knew what Becky meant. Joking or not, she was implying that she was so enthusiastic a lover that Rob and I together would have a difficult time keeping up with her had thing progressed as they were going. But Rob; had he meant the same; that Becky and I together would not be able to satisfy him sexually? A few days later, Rob and I were taking a bike trip along an abandoned railway spur. Back then the "rails to trails" program was just getting underway, so that section of track was pretty empty, except for the two of us. As we rode, we came to a gap in the trees which lined the right-of-way. Rob turned off the rail bed and through the gap into a grassy field. "Aw, man," he muttered. "What?" "Those people," he pointed to what we took to be a father and his kids flying kites at the far end of the field. "I was hoping to sunbathe nude up here today." For the second time in a week, Rob caught me by surprise. He shrugged, swung his bike back through the gap in the trees and headed back down the tracks toward home. When we got to his place, both of his parents were at work, so again we had the run of the house. After taking a few minutes to clean up after our sweaty bike ride, we ended up in the basement game room. It took me a little while to get my courage up, but I finally had to say something. "Rob, I don't want to make you mad, or anything, but can I ask you something?" "Sure," he said with a slightly confused look on his face. "The other night, you said Becky and I couldn't handle you. Did you mean...?" "Yes," he interrupted me with a slight grin. "You mean..." "Yes," the grin got wider. "With guys?" "Uh-huh." "So you've sucked cock?" "Yes." "Wow." I was all but speechless, but I felt a stirring below my beltline. I gathered my nerve for the next question. "So what's it like?" He smiled even wider. "I could show you, if you want." I gulped, pushed my nervousness aside, and said, "Okay." Without saying another word, Rob peeled off his t-shirt. He put his hands on my biceps and leaned in to kiss me. I felt his tongue touch my lips, so I opened my mouth to receive my first man-to-man kiss. Rob's hands drifted across my chest before pulling my t-shirt free of my cutoffs, and then up to my neck so he could lean in and lick and suck and nibble my nipples. It was like an electric shock which ran straight to my cock. As Rob got to his knees and began working on the button of my cutoffs, I pulled the shirt over my head and threw it on the couch. As I turned back to face him, Rob slid the denim shorts down to my ankles. I wore no underwear, and we were already barefoot, his being a "shoes-off house". I kicked my feet free of the shorts and stood there, naked with my friend kneeling in front of me, his face just a few inches from my erect member. "That's nice," Rob murmured. He took me by the hips and told me to sit back on the couch. As I did, he stood and pulled off his own pants, freeing his stiff cock. It was the first one I'd ever seen in person -- not in pictures or movies. His dick was a bit smaller than mine; about five inches long and slim, but his balls were somewhat larger and hung lower. I expected him to sit next to me, but he got between my legs, and in a long, slow suck, took me into his mouth. I can still feel the smooth warm wetness of his tongue sliding across the sensitive tip and the touch of his fingers as one hand grasped the base of my cock and the other cupped and toyed with my balls. The sensation was incredible as he sucked and licked and took me all the way down. It didn't take long before I felt the orgasm starting to build. "I'm going to cum soon." I told him. He withdrew his mouth briefly. "Do you want me to stop?" Without waiting for me to reply, he dropped back down to my dick and sucked me hard and fast until I exploded in his mouth. He kept gently On impulse, I caught him by his shoulders and drew him up onto me as I leaned back. His hard prick rode up between my legs, and across my balls. I pulled him close and kissed him. I could taste my cum on his tongue. I marveled at the flavor, sweet and pungent at the same time. That gave me courage to take the next step. "When I asked what it's like, I didn't mean to get a blowjob; I meant to give one." I whispered. "Oh, in that case," he smiled and rolled off me. He laid on his back with his legs apart, one up on the back of the couch and the other bent toward the floor. I slithered on top of him. My cock, still twitching from the treatment he had just given it dragged across his as I leaned to kiss him again. He grabbed my ass, wrapped his legs around my hips pulling me in close as he humped against me. Reluctantly, I broke the kiss and slid down a bit and began to lick and suck and bite his nipples. Then, moving down even further, I took his prick in my hand and his sack in the other. I began to jack him. A single pearl of pre-cum formed at the tip. Without hesitating, I flicked out my tongue and caught the drop before it fell. I continued to lick my way around the engorged head of his cock, working my way down the shaft to his balls. Gently, as he had done, I licked and sucked each hairy orb while continuing the long slow strokes of my hand on his cock. Then in one swift motion, I took him into my mouth. Doing my best to imitate what he had just done, I pumped his dick between my lips. I ran my tongue across the smooth head. I sucked him all the way into my throat, fighting the gag reflex until my nose was buried in his pubic hair. "Oh, man, I'm gonna shoot," he gasped. "You'd better stop." He hadn't stopped. Neither was I going to. I felt the first pulsing of his cock and a thick stream of jizz squirted into my mouth. It had a slightly different taste than mine, but I swallowed his load and kept sucking and stroking until his orgasm subsided. Rob sat up, gasping, and drew me up to kiss me again. "Wow. For a first effort, that was really good." "I'm glad you enjoyed yourself." "If you want," he offered, "I can teach you to be better." I thought for a moment. "I'm not sure. I mean I had fun, but I really prefer girls." "I understand. Just don't limit yourself. Guys can be just as much fun." "I noticed," I laughed. "We'll see. Maybe we can do this all over again sometime." We both knew we would. First Gay Sex Experience The first time I had gay sex I was 21 years old and a senior in college. I am a straight male that always wanted to try hooking up with a guy but I was in a long relationship, so I abstained. After we broke up, nothing was holding me back but I continued to resist me curiosity. One morning, I decided to go for it. I was familiar with anal play which I always liked, but besides playing with myself, I never came close to hooking up with another guy. I liked anal play so much, I wanted to try bottoming. I went on Craigslist and looked through some ads of random guys. I emailed a few and one seemed very interested and interesting at the same time. He said he was a young guy with a big dick, which was exactly what I was looking for. I told him to come over after sending some dick pics back and forth. After giving him my address, I realized I couldn't back out at that point. By the time he arrived, I was incredibly nervous. He was a nice guy, about my age. He brought a joint over which helped a bit to ease the nerves. We smoked it a bit and had some casual small talk. He had just graduated and I was just about to. He told me he had done this a few times but still considered himself bi. After we smoked it we were sitting on my bed and he asked "so you want to take your pants off?" I was hesitant for a second and then I said sure. I pulled my pants down, showing my 7 inch bulging uncut cock. He said, "wow, nice dick." Then he asked, "do you want to take off my pants?" I reached for his jeans and slowly unbuttoned his pants. I could feel how hard and big his dick was as I unbuttoned them. I pulled down his boxers nervously and saw the biggest dick I had ever seen in person. It was over 9 inches and thick. I was pretty worried it wouldn't fit at this point. Almost right away, I grabbed it and started stroking it. It felt good in my hand because I could feel it throbbing. I lowered my head and started sucking it almost immediately, not knowing really what I was doing. His dick was hard to fit in my mouth but I let him slowly push deeper into my throat. He seemed to like it a lot as he let out a moan, so I started taking it deeper and deeper down my throat. It was pretty hard not to choke as he pushed my head further on his massive cock. I liked how it felt being forced on his dick and the taste of his Precum dripping down my throat. I could fit both my hands on his dick as I sucked it and rubbed it at the same time. He kept trying to go for mine but I kept sucking his dick because I liked it too much. Finally I let him suck mine for a couple minutes. I had a lot of straight sex prior so I was not thoroughly impressed with the blow job. I assume mine was better but I think it was because my excitement and nerves. I was really anxious to bottom and asked a few times if he would fuck me as he sucked my dick. He told me in a little. He sucked my dick a bit longer and finally asked me, "you sure you want to?" I said yes, thinking all I wanted was his huge dick in my ass. He told me to bend over doggystyle on the side of my bed and asked if I had ever gotten a rim job. I said no and he started to lick my tight little ass. It felt amazing. My dick had precum dripping off as he licked my ass with his amazing tongue. My ass was wet from his tongue. He started fingering my ass with one and then two fingers. He kept licking the rim of my ass as he shoved his fingers in my ass. I wasn't touching my dick but it felt amazing and was dripping wet. He finally asked "are you ready?" I said yes, wanting him to shove his massive dick in. He grabbed some lube I had and rubbed it on and in my ass as he kept finger fucking me. He asked if I wanted him to wear a condom. I said no, I was probably only going to do this once so no, I wanted to be barebacked. I trusted the are you clean formalities and got lucky. He slowly began to slide the tip in to my wet ass. It was huge, but I was so hard it felt amazing. I had put a smaller dildo in my ass once before so I was slightly more prepared. It was so big it felt like it never stopped as he slowly pushed it deeper and deeper into my tight ass. Finally I felt his balls on my ass as he rubbed them on me and I said, "you made it, now I'm going to fuck you slowly" He asked me if it felt okay, and I said I think so. It took a second to get over the initial pain which never fully went away but it felt amazing. His dick seemed to be hitting all the right spots, because it was the best feeling I had ever had. He asked if I liked a big cock in my ass and I moaned through a yes. He kept fucking me slowly as he spread my small ass a part. He gradually fucked me harder and harder, faster and faster. I could feel him filling my ass up. Soon he was fucking me hard, which hurt but felt so good at the same time. My dick was rock hard as he kept fucking my ass with his huge dick. His 9 inch cock somehow fit in my virgin ass as he kept pouring more lube on. He spun me around and began to fuck me while I was on my back. He pushed my legs back by my ears and slid his dick in. It went in surprisingly easy this time. This position even filled me up more. I could've sworn his dick was 10 inches by now as it got harder and harder. He rubbed my dick slowly as he kept fucking me. I was moaning with pleasure as he thrusted my tight ass.. Without taking his dick out, he rolled me over so I was laying flat on my stomach. My hard dick was against the bedding rubbing up and down as he fucked me. He slapped my ass and asked if I liked his bare dick in my ass. He pinned my neck down gently and started fucking me hard and I felt like I was going to cum. I wasn't touching my dick but the more he shoved his 10 inch dick in it in. Soon I couldn't hold it in and I came all over myself, uncontrollably. I came the most I ever had and couldn't stop orgasming as he kept fucking me. I told him I came finally after I couldn't handle it anymore and he pulled his massive dick out and told me to roll over. He asked if I wanted to cum in my ass or in my mouth and I said either. He told me to open my mouth and he started jacking off above my head. He filled my mouth with his cum and I swallowed it fully. My ass definitely hurt more than I noticed when he was fucking me. Let's just say I'm still not as tight as I was before him and I haven't experimented more since. To this day, it is my only gay sex experience. I don't think I'll try again, but I'm happy I did it once. If I did, I definitely know I'm a bottom and I prefer a big dick.