He's crying for some reason. My mind still feels detached from my body. I'd been fucked by a lot of my male friends and quite a few adults and none of them had ever fucked me like this or made me feel so... weird. He's apologizing to me but not all that sorry to stop what he was doing. A part of my mind kept reminding me that I'd wanted sex with him and this is what I get for suggesting that he have sex with a guy... and thinking that I felt sorry for the girl who would give him pussy for the first time. He came. Again. Stayed in me and I thought, "Oh, no, not again - I can't take any more of this!" My whole body was hurting, some of it good, a lot not so good; I didn't like being screwed in the missionary position because it always made my hips hurt and like they were being dislocated. "I'm sorry if I hurt you but it felt so good and I couldn't stop," he said. "Thank you." "You're welcome," I groaned. "Um, you're kinda heavy." "Oh!" he said and moved; I could feel his dick sliding out of me and it felt like... that time I was having stitches removed. Weird feeling. I heard his dick... pop out of me followed by... a breeze. I'd only felt that when certain adults had fucked me and never with a friend but, then again, none of the friends I had sex with had a dick like Ronnie's. I sat up and the room spun for a moment; I managed to get to my feet because I had to go to the bathroom but when I stood up, whatever cum hadn't leaked out of me poured out of me, streaming down my thighs. I... didn't feel like I had to go now. Weird. I sat back down because my legs didn't want to hold me up and Ronnie's looking at me like he's a puppy that just got a beating. "I'm okay and it's okay," I said. "I wanted to do this for you and, well, man, you really did it! I'm going to be walking funny." We'd just sat there quietly for maybe five minutes. There was nothing for me to say but he was looking like he had something to say but I was okay with waiting for him to speak. "Can... we do this again, like, maybe tomorrow?" he asked. A part of me wanted to say no. He'd worn me out with that big, fat dick and amazing stamina. I did not want to go through that again... but how could I say no? What kind of friend would I be if I did? "If we do it again tomorrow, um, do you think you can fuck me?" he asked. "I mean, it's fair, right?" "Yeah, I think it is," I said. "We can do it tomorrow if you really want to." Somewhere inside of me, I knew I was going to regret saying this, well, my poor asshole was going to regret it. I'm sitting next to him and I can see his dick... "squirming" like it's a snake and I almost laughed to think that. I finally had the strength to get to my feet so I could find my clothes and get dressed. He was looking at me like he wanted me to stay but I thought that if I did, that big, fat dick was going to wind up in my ass again. I said my goodbyes to him, renewed my promised to come over tomorrow so we could have sex again, and headed home and thinking about all that had happened. Was it a mistake? Did I do the wrong thing for the right reason? Was my ass going to be sore come tomorrow? Did I have what it took to deal with him again?
He kept saying, "Oh, shit!" over and over. He's slamming his dick into me so hard that... I came again. He put his full weight on me and really gave it to me harder and faster; his body suddenly went as stiff as a board and I could feel his dick pumping hard and strong in me. He's... paralyzed; he can't move or speak and all he could do was breath hard. I'm paralyzed, too, but, nah, not really - I just didn't dare move as he pumped cum in me. I thought he was done. He wasn't. He started moving again and, for a moment, I felt a pang of great envy that he could fuck even though his dick was soft but I thought that it was because his dick was so long. He kept saying, "I'm sorry..." and kept fucking me. I'm... seriously squishy. He'd pumped his cum in me and was now fucking it out of me. Then I could feel his dick getting hard; stretching me open again and I... kinda blanked out. I was there but I wasn't. He busted another nut in me and I almost panicked to think that he was going to keep going again. He pulled out of me and it felt like it took forever for him to pull it all out. He wasn't done with me, though. He leaned over and started sucking my dick until I got hard. He swallowed me whole and in the back of my mind, I was kinda impressed because few people outside of a couple of the adults I was having sex with could do that without gagging... but it made sense that if he could suck a lot of his own dick, my "puny" dick was a piece of cake. Even though I had cum twice when he fucked me, it was like I... wasn't finished? I didn't understand what was going on but what I did know was that my friend, the one everyone called a freak of nature, was about to make me cum "for real." "I... I gotta cum," I said. This was... automatic for me because girls who sucked my dick told me that I'd better tell them that I was going to cum - or else. Ronnie picked up the speed; my back arched and I could feel my dick swell and I started to cum. Ronnie ate all of my dick and held it there as I came. He sucked every drop of cum out of me and slowly released me to sit up and... just look at me. The look on his face scared me and when he moved, I knew he was moving to stick his dick back in me and I almost said, "No..." but I started this and he was now determined to finish it to his liking. I... moaned like a girl when I felt his dick slithering back into me. "This is so good," he murmured. "I can't stop doing it!" It... wasn't so good for me. I was so sore and I felt so helpless under him. His stamina was... freakish. I felt myself becoming detached, my mind wandering but clearly thinking that this was the first time he got to fuck someone so, yeah, he had a lot of... catching up to do.
There was a lot of it. Thick and a little salty. I'm having a hard time keeping up with it and I'm swallowing as fast as I can; some of his cum gets away from me but I wasn't going to take my mouth off of him - I could lick my lips later. The thing was that when he finished cumming, I wasn't finished with him. I'd spied the hair grease he used to make and keep his hair so wavy and looking good. I got up and grabbed it, set it on the bed, then got out of my clothes. "What are you doing?" he asked. "What everyone else is afraid to do," I said. I smeared a glob of hair grease into my crack and used a finger to get it in me; I grabbed another glob of it and started rubbing it all over his dick. "Are you gonna do what I think you're gonna do?" he asked. I just nodded and straddled him, trying to stay balanced to get into position while holding his dick. He wasn't hard but I figured that he was so long and thick that I could get him in me and... I was right. I put him against my hole and slowly started to sit down on him and, wow, whew, yeah, it was hurting but nothing I couldn't handle. I kept sitting down until I had all of his dick in me and it felt good but very uncomfortable. "Be still," I said and started riding him. I'm looking at him and he's got tears streaming down his face; I'm used to him now and all I wanted him to do was cum in me. I'd told him to be still but that was "stupid" because I knew he wouldn't and almost on cue, he started to fuck me. Slowly at first but it wasn't long before he'd grabbed my hips to hold me still and... he hammered my hole. I was having orgasms. A glance down revealed something I rarely saw when being fucked: My dick was hard. Ronnie's moaning and fucking me like his life depended on it. He went deep in me and... I came. I'm gasping like a fish out of water and watching spurts of my cum landing on his chest and... there was some on his cheek. It's... starting to hurt again but I was well and truly committed to relieving him of his virginity and getting his cum in me. He surprised me by rolling us over and, oh, my, god, he was banging the shit out of me now and all I could do was lie there and take it which wasn't normal for me - I hated being fucked really hard.
We were friends but there was something he didn't know about me: My bisexuality. The fact and truth that I had sex with guys. I'd thought about sharing my secret with him but never "got around to it." "Um, how come you haven't tried having sex with a guy?" I asked. "I mean, that's what a lot of guys do when they can't get any pussy." It was a suggestion more than a desire for me to have his dick - and, yes, I wanted it. I'd seen it too many times not to want it but watching him give himself a blowjob made me want it even more. "I thought about it," he started. "I asked Junie if we could have sex and he said my dick was way too big." Junie was one of the two gay dudes in our group and I found it surprising that he turned Ronnie down because Junie was known for taking on any guy (and including quite a few adult men). I didn't want to ruin my friendship with him; I'd lost a few friends because I had no qualms about having sex with a guy but I couldn't take any more of seeing him suffering and being down on himself because, again, he didn't ask to be born this way. "Look, um, if you want to have sex, I'll have sex with you," I said. I waited for him to lose his mind, start cussing me out, wanting to fight, and ending our friendship right then and there. "You would? So it's true that you go both ways?" he asked. I didn't know who told him but I just nodded. It didn't help that, like me, Ronnie wasn't all that modest; he hadn't put his pants on after sucking himself off and I couldn't take my eyes off of his dick and was forcing myself to look him in the eye. "Don't you think it's too big?" he asked. "If I did, I wouldn't have told you what I did," I said. "You don't have to but it breaks my heart to see you going through not being able to get laid, so..." He sat back and I could see that he was thinking about my offer. I was afraid that he would say no and end our friendship. "Well, okay, if you want to," he said and stretched out on his bed. It was all I could do to not jump on him like I was a starving animal... which I was. I walked over to his bed, sat alongside him, and took his dick in my hand. It was very warm and heavy in my hand and I could feel him starting to get hard again. I took the head of his dick into my mouth and he moaned; I took some more in and he gasped. I kept taking more until my gag reflex demanded that I stop but that was fine because I now had a lot of his dick in my mouth... and I started sucking him in earnest. I fondled his huge nuts; I used all of my skill in sucking his dick. "Oh, shit, I'm gonna cum," he moaned and I barely managed to back off to the head of his dick before mouth got flooded with his cum.
Ronnie was 13 and like most of us were. He was tall for his age, towering over the rest of us who were lucky enough to be over 4' 5". He was skinny, too; that alone was enough to get the "freak" label slapped on him. What really made him a freak was that he had a thick, 10" dick and a set of balls that belonged on a grown man's body. Girls didn't want anything to do with him even though, despite his height, he met their other criteria: He was handsome, somewhat light-skinned, and had very wavy hair; I know I used to tease him about his hair by saying it was so wavy that people who looked at it would get sea sick. As such, he was an outcast and among us guys, too; Ronnie would get picked on because of his height and was the object of a great deal of penis envy. The rumor going around that got a lot of guys riled up was that girls were losing their minds over the size of Ronnie's dick and were flocking to him to be fucked with such a big dick... but I knew it was only a rumor because I knew that because of the size of his dick, Ronnie was still a virgin, unlike the rest of us. I was, maybe, one of two friends that were true friends to him; the other guys teased him unmercifully and often displayed a lot of jealousy by saying that he was so much of a freak that he could suck his own dick. Well, I knew that part was true because I watched him do it one day and, yeah, I was a bit envious and very much impressed. We had been in his room and I'm listening to him telling me about his recent failures to get a girl to have sex with him and the more he talked about it, the harder his dick had gotten and, whew, there was no missing the fact that he had an erection even though he wore baggy pants in order to hide his size and girth and more so when there wasn't a pair of underwear that could contain his dick. He's talking, getting both frustrated and horny and I'm feeling so sad for him. He stops talking and says, "Promise you won't say anything?" "About what?" I asked. His answer was to shuck his pants and free his erection and... I drooled. My own dick started to get hard just looking at his boner. He gave me a look, kinda shrugged, and just bent over and started giving himself a blowjob. I almost came in my pants. Kept wiping my mouth. He'd started out slowly but really picked up the speed. I couldn't stop watching him. A few moments later, he came in his mouth and I... came in my pants watching his dick pumping cum into his own mouth. "You can't tell anyone about this," he said after he was done draining his balls. "I won't," I said. "This is the only way I can... take care of things," he said and my heart went out to him because it wasn't his fault that he was born the way he was.
When your confidence is up and running, there should be little doubt going on in your head. Okay, maybe a little. But being confident means that that little bit of doubt... isn't going to be a problem because you know you're going to do your best for it to not be a problem. A guy tells me that he cums too fast when he gets sucked. He actually said that he wasn't confident that he could hold off from cumming long enough to make me happy and... I got in his case and told him, "The whole purpose of me sucking your dick is to get you to cum and if it happens quickly, okay - you did what I wanted you to do and you did what you wanted to do: You wanted to cum in my mouth and you did. Man, you need a serious confidence boost..." Another guy tells me that he's not good at sucking dick. His past experiences had eroded whatever confidence he may have started out with and my words to him were, "Don't worry about being good at it; be confident that you're going to do the best you can because it's all that any of us can do. Besides, isn't it kinda up to me to decide if I think you were good at it?" He said it was and I said, "Okay, so, what's the problem? Are we gonna do this or what?" But I knew what the problem was: He lacked confidence. He believed that he was lousy at it and was sure he was going to fail to please me and... he was wrong about both things, but he did say that I gave him back his confidence and I suggested that, going forward, he not let anyone take it away from him and he should never take it away from himself. If you don't have confidence, you don't have anything. If you let someone erode your confidence, that's not their fault: That's your fault. Confidence always begins with you. A guy tells me that he's not confident that he can make me cum and I'm thinking, "You're kidding, right?" I said this and he starts telling me about all the times he failed to make a guy cum and while he loved sucking dick, those failures made him less confident and he'd decided to stop trying to make a guy cum. I was... furious. Probably shoudn't have been but I was. I had a long talk with him about being confident and that also means accepting that you will fail at times... but that should never mean giving up and not believing in yourself. He didn't want to go through with it but I convinced him to and... he made me cum. Pretty quickly, too. He was encouraged but said it was a fluke which meant to me that we had to do this again so he could see - and have proven - that it wasn't a fluke. It wasn't. It took him longer to make me cum but I sure the hell did. He got his confidence back. He called me about a month later to tell me that he'd sucked a lot of guys since he sucked me and... made all of them cum. Amazing what some confidence in yourself can do, huh? My final words are if you aren't sure about how confident you are about having sex with men, learn to be confident and beginning with being confident that you are going to do the best you can do.
It's not... bragging or otherwise "talking shit." It's that... knowing that you're going to do the best you can and being confident that you can and will learn how to have sex with a man and whether it's your first time or the one hundredth time. You can't please everyone but if you're not confident that you're still going to try to, well, hmm. I remember the first 9" dick I had. Homey pulled that snake out and my first thought was, "Oh, shit!" and he wasn't even hard. I wasn't sure if I could suck this guy's dick and it was an ugly feeling inside of me and it didn't help that he was waiting for me to get started. I... lacked confidence in my ability to suck dick and was intimidated by his length and girth. He asked, "Well, what are you waiting for?" and I wasn't going to tell him that I was waiting for my confidence to return but it did and... I had him hollering for his momma and Jesus to come save him. When you don't have confidence, you don't have anything. A lot of guys say, "I wanna do this but I don't know if I can get away to do it..." and I understand that but if you're not confident that you can't find a way to do it, you aren't going to be able to do it. The same kind of guys say that it's impossible when it isn't if you have the confidence that you can "work the problem" and find a solution if, you know, it's something you really want and need to do. You have to... believe in yourself. Have a level of confidence that says you will try your very best to do whatever it is you want to do. Don't let a lack of dick size destroy your confidence in your body's ability to get your dick hard so it can be made soft again. Not confident that you can deep throat a dick or take a big one in your ass? If you believe that you can't, then you won't be able to but confidence in yourself says, "The only way we will know that we can't do it... is to do it and doing our best to deal with it." I was confident that I could deep throat a guy with a measured 13" dick. It was daunting as fuck and, for a long second, I wasn't sure that I could - but my confidence in myself came back and... I did it. Holy shit! High-fiving myself big time. Amazed the shit out of him because no one had ever taken all that dick down their throat before. Next was... taking all that dick in my ass and, again, my confidence wavered but returned because I was confident that I was going to do whatever I had to do to get that dick in me... and get - and deal - with all of it in me. Yeah, I knew I was going to "pay" for all of this later... but I was also confident that I would be able to deal with the aches, pains, and very sore throat I got from repeatedly deep throating him. Building confidence, however, should never result in being cocky and I've encountered a lot of guys who were cocky and, well, let's say that they learned not to be and, yes, it was a lesson I had to learn - and learned it the hard way even though my parents had taught me to not be cocky. You live and learn, right?
I had been invited to audition for the all-state orchestra - quite an honor. I played trumpet and I had to pick a piece that had to demonstrate my understanding of music and my "mastery" with my instrument. My band director sat with me and we picked a piece - "The Trumpet Song" and looking at the music I thought, "Oh, shit... this looks hard!" and, well, yeah, it was but he convinced me that once I got to practicing it, I would be able to nail it. Yeah, not really. There was this one part of the piece, oh, about five or six measures worth, that I couldn't get right. I kept playing those measures over and over and fucked it up every time. I was frustrated and lacked confidence in my ability to play the piece and was thinking about not auditioning. He... jumped in my ass. The first thing he told me was that if you don't have confidence, you don't have anything. I had to be confident that I could do this because if I wasn't, my audition would go very bad. Those words were serious words of wisdom for me; I auditioned, played the piece, and got selected. I found that his words to me were true for... having sex with a guy and especially if it's one's first time. In the many times I've given a guy his first experience, I sometimes had to tell a guy what my band director had told me: If you don't have confidence, you don't have anything. You have to be confident about a lot of things but confident in a way that's not... fooling yourself; it's something I discovered that a lot of guys were doing and false confidence... doesn't work in this. You have to truly believe that you want to do this and that you can do this... and you are going to strive to be the best you can be at it. And beginning with having confidence in yourself. I don't know how many times I've been negotiating with a guy for some mutual cocksucking and the other guy is going on and on about not being sure if he's really good at sucking dick or otherwise being self-depreciating. Lacking confidence in himself. Already deciding that I'm going to say that he's worse than being lousy at it. Getting all weird about not having a monster-sized dick. That he cums too fast or lacking confidence in his ability to just relax and let it happen. Sometimes not even being sure that this is what he wants to do. It drove me "crazy." I had realized that being confident was, in fact, a lesson I'd been taught all along but sometimes something comes along that challenges your confidence and if you don't accept the challenge and do the best you can do, well, that's a problem.