Date: Mon, 8 Apr 2002 10:54:36 -0700 (PDT) From: Jonathan Seagull <livingbird12306@yahoo.com> Subject: David & Matt - Chapter Two - Anal Experimentation DISCLAIMER: The following story is based on facts - it's about some of the events in my life while I was growing up. I've changed the names to protect the innocent. Only the two people portrayed in this story would be able to figure out that the story is about us anyway. This story is about two young teenagers who come of age and discover and explore their mutual homosexuality with each other. If stories like this offend you, or you are not yet at least 18 years of age, or viewing this type of material is illegal where you are, please do NOT read this story. If you decide to continue, I hope you enjoy hearing about my teenage years spent with my best friend. This is the second of two chapters, more chapters will follow. DAVID AND MATT Chapter Two - Anal Experimentation After our initial weekend together, Matt and I couldn't wait to get together again for more sex! It was during the school year, and we both attended different schools, but we were still able to get together often. Days I wasn't busy after school, I'd usually ride my bike over to his house. Often I'd arrive just as he was getting off his bus. Usually we'd go in the house and he'd flip on the TV. Nobody else was home. We'd sit in the living room and watch some TV and talk about what had happened that day at our schools. Usually it didn't take long, and I'd be watching something on the TV. Next thing, I'd hear Matt let out a low sensual moan. I'd look over and his hard dick would be sticking out of the fly of his pants. He'd have a shit eating grin on his face. In a flash - I'd leap over and grab his dick and start jerking him off, sometimes I'd just go down on him. I'd only do that a for a minute and then I'd stand up and he'd unleash my hardon from my jeans and reciprocate! Both us us would be stiff as boards. He'd flip the TV off, and zip up. So would I. Then I'd follow him up the stairs to his room. Usually on our way up the stairs I'd be following him, so I'd reach between his legs and grab his cock and balls. He'd stop and let me fondle them a minute before we'd get upstairs. Once upstairs, the fun would really begin! We'd both get completely naked. Then we'd take turns lying on the bed, while the other gently sucked our cock and balls. It was really sensual. Didn't take too long to get really hot and bothered. After a few minutes of this we'd get in a '69' position, laying on our sides on the bed, and then we'd spend a good few minutes slowly working on each others' hard cocks. Sometimes we'd finger each other's assholes as well. Usually not though, which disappointed me - as it really turns me on when someone massages my hole! Eventually we'd both be nearing our climaxes, and one of us would stop sucking the other just long enough to warn that we were about to come. Usually this happened to both of us almost at the same time. We'd end up jerking each other off, squirting our boy cream all over each other's belly and chest. Usually we'd clean ourselves up and lay around naked for a bit, then go at it again. Sometimes we'd even go for a third time. Usually though his father or mother would arrive home, and it was dinnertime, and we'd get dressed, and I'd go home. One day after we'd gotten off once, we checked downstairs and found no one was home yet. We both raced down the stairs butt naked to grab a snack out of the fridge. There was a racket on the street, so Matt ran into the living room and knelt on the couch, which was up against the window, and looked out. I stood behind him and just staired at his ass. It was absolutely gorgeous! Smooth, hairless, creamy white cheeks! At that point in my life, I didn't know anything about rimming, or I'd have known that that was what I wanted to do to Matt. All I knew then was that I wanted his ass, and I was pretty sure I wanted to put my dick up it! Well, we didn't get time to discuss things, as the racket was his father arriving home. We beat feet up the stairs, and dressed quickly. I left, but before I did we made plans to have another sleepover (our first since our first weekend of sex) at his house that Saturday night. I couldn't wait! I was going to introduce my hot lover to butt fucking! Saturday arrived, and all day I felt flushed and my heart was racing. I couldn't wait to get Matt alone, naked, in his room all night! Well, there was a slight delay that evening. He and his mom came to pick me up and his mom insisted that we go to church on the way to his house for Saturday night mass, so that we could all sleep in in the morning. Well, that had it's benefits too I guess. So we both sat in the pew next to her, with our crotches bulging. I don't think she noticed. She was a little upset because we kept giggling over the priest's accent. We actually broke out laughing when the priest belched at one point! She was still lecturing us when we got to their house, and she said "Oh just go to your room then!". Which was fine by us! We said "Good Night" to Matt's parents, and up the stairs we went. On the way up, of course I reached through his legs and grabbed his hard penis! Soon as we were upstairs, we ripped all our clothes off and grabbed each other's dicks and started jerking each other off. We were both really hot. Matt stopped suddenly, and said, "Wait, I gotta put some records on to cover any sounds we might make!". As Matt was bending over to put a record on the turntable, I sidled up behind him and placed my hard dick on his ass crack. His head popped up and he looked back at me. I gave a slight thrust forward, and my cock head was between his cheeks nudging his sweet little puckered hole. Matt's eyes were kinda big, but he grinned and said "Oh, that feels good!" and pressed back against me a little. But then all too soon, he pulled off my pole and finished setting up the records. When he was done, he straightened up and turned to face me. It was at that point I suggested we try butt fucking each other. I told him how I'd been sticking different things up my butt lately, and how good it felt. I'd tried a smooth-handled screwdriver (handle side obviously), and I had a friend who's father smoked cigars that came in hard plastic tubes. I'd swiped one of his empty tubes from a waste basket once. That was my favorite toy. Well, my stories were getting Matt hotter than ever. He too said he'd stuck a couple things up his butt too - but mostly, just his finger. Anyway, I told him we'd need some lubrication, like vaseline or something. He said they had plenty of that, but that it was downstairs and we'd have to wait for his parents to fall asleep, before he could sneak down and get some. Not to worry - we found other activities to keep ourselves busy. I think we sucked each other off a good 3-4 times, before he said they'd be asleep for sure. So down he went to get the vaseline. Matt returned a couple minutes later with a sheet of waxed paper resting on his hand, with what looked like the entire contents of a huge container of vaseline resting on it, and a bunch of paper towels. Since it was my idea, I volunteered to let him fuck me first. Oddly, neither of us was sure of exactly what to do, so while he liberally greased his love pole, I laid on my stomach on his bed, and spread my legs wide. Matt knelt on the bed between my knees and scooched forward toward me. Then he took a gob of vaseline on his finger, and with his dry hand, he spread my ass cheeks apart. He stuck his greased finger directly on my asshole, and started rubbing. Immediately I was moaning, and I felt some pre-cum dribbling out my piss slit. Eventually, he started to use the tip of his index finger and he pushed against my hole. Suddenly, his finger burst through my sphincter, and up into my butt to the second knuckle. It hurt a little, and I yelped. He pulled it out quick and apologized. I said, "That's OK, it only hurt for a second. Why don't you try your dick now, but take it easy!". So he wiped off his greasy hand on a paper towel, then leaned over me, and positioned his greasy dick between my buttocks! He slid it up and down a couple of times. It felt great! More pre-cum began dripping from my dick. Slowly, Matt lifted up a little and positioned the head of his hard cock against my asshole. I tried to push up a little to meet him at the same time, but he was already down on top of me pretty far. Then with a small shove forward, Matt's huge cock slid through my ring and halfway up my ass! I thought I was going to die from the pain, and let out a yell "It hurts! Get it out!" He quickly withdrew. I had tears in my eyes it had hurt so bad. Matt was looking anxiously at me to see if I was alright. I told him I was. But, when my hand went back to my poor hole, that only seconds before had been impaled by his dick, I wasn't sure I would be OK. My hole was stuck wide open. I could fit three fingers in it it was open so wide. It kept trying involutarily to squeeze shut. Finally, the pain died away, and my hole started to close up again. I was kind of embarassed, and upset that it didn't work. I'd really wanted to feel Matt fucking me! I also hoped I hadn't yelled loud enough for his parents to hear! Nobody came to check on us, or hollered up the stairs, so we figured we were safe. Matt looked a bit worried now. He told me he still wanted me to try and fuck him. But he admitted he was worried about the pain too. I told him he didn't have to if he didn't want to, but he said, "No, fair is fair - you tried, so now I'll try!" After I'd recovered from the pain, Matt laid down on the bed the same way I had. I too, greased my dick, and then rubbed some vaseline all over his asshole. Eventually I pushed a finger in, and both of us liked that feeling! Matt finally said, "OK, let's try it - but go slow!". Like Matt, I dried off my greasy hand first, and then leaned over him and rubbed my greased pole between his cheeks. It was wonderful! Finally, I stuck the tip of my dick against his puckered love hole, and said "OK, Here it comes." Matt tensed up (wrong thing to do), and I slowly pressed downward. I wasn't having much luck, as Matt was so tense. Finally, as I was pushing, I said to Matt "Man, you gotta stop squeezing shut or I'll never get in!". Suddenly Matt stopped tensing up and I just about collapsed into him, my dick sliding into his hole up to my ring meat. This time it was Matt's turn to bellow at me to get it out. Which I did immediately. He too had felt the pain I felt, and his quivering hole wouldn't close up right away either. Like me, he too had tears in his eyes. With that, our exploration of anal sex ended for a while. We both agreed that it felt incredibly good when our cocks were up inside each other, but neither of us could handle the pain involved in letting the other one put their love tool up there. That night, after we'd both taken some time to recover from our impalements, we resumed our usual sex play of sucking and jerking off. We also spent some time trying to fuck each other between our thighs, in our armpits, and anywhere else we thought it would feel good. In the end, we settled for basic sucking and jerking. I know many or you won't believe this, but that night, I counted, and I came 14 times! I know, the last few times were pretty much dry orgasms, but still - we had a lot of sex that night! Exhausted, we finally fell asleep naked together under the covers. Several weeks went by, with us doing our usual every day or so afterschool lovemaking. It was a great time in our lives! I was still wondering though what had gone wrong with our attempts at anal sex! I knew that gay guys did it all the time and loved it, even on the receiving end. After some thought, I decided that we'd been in the wrong position, and hadn't properly loosened each other up. So, one Saturday afternoon, when Matt's parents went out and left us home alone, I told Matt what I'd been thinking and asked if he'd like to try butt fucking one more time - he agreed that what I said made sense, and agreed we should try it again! He grabbed some waxed paper and piled on a gob of vaseline. I grabbed the paper towels, and up the stairs we went. Of course we stopped halfway up so I could fondle his hard dick from between his legs! Once in Matt's room we quickly got naked, and Matt said "OK, last time you let me try to do you first, this time I'll let you try to do me first!" I agreed. So Matt said, "Well, how did you think we should do it?" I said "Doggie", and showed him how to get on his hands and knees on the bed and poke his ass back at me. Matt assumed the position, and I greased my dick up and moved behind him. He was really nervous. I told him to relax and enjoy what I was going to do to him - that I'd tell him before I tried my dick. So I went to work massaging his beautiful asshole and finally managed to get a finger inside. I slowly finger fucked him - he loved it. I stuck a second finger in, and he moaned a bit. I continued to finger fuck him. I must've been pressing his prostate each time I went in. He was moaning a lot, and said he felt like he was gonna cum. I said, "Well, I think you're loose enough, want me to try me dick?" He said "OK - but slow and gentle!". So slowly I placed my dick head against his love hole and told him "OK - now just relax!" He did. I slowly pressed forward, and felt the head of my dick go inside him. Matt gasped. I asked if he was OK. He said it hurt, but not as bad as last time, and to keep going. I slowly slid forward, until my throbbing cock was completely up inside Matt's hot rectum. And I'm not kidding you - his rectum was hotter than hell - physically speaking. I think the boy had a fever or something. I only ever felt one other guy that had such a hot rectum since then. The others I've been in weren't so hot. Anyway, I was really enjoying where I was, so I slowly slid backward and out, and there was an audible gasp of relief from Matt, until I started to slowly push forward again, and his gasp turned into a pained whimper. I looked over his shoulder and his face looked pained. I stopped, and he said, "Dave - I can't do it - get it outta me - Please!" - so with that I withdrew, and he heaved a sigh of relief. I felt sorry for him, that I'd hurt him, yet again. I also wsa sorry it hadn't worked. I really wanted it to work. Well, in a bit, I told Matt it was his turn to try and do me. He was surprised. Thought after the second attempt on him had failed, I wouldn't want to. I said "Well, fair is fair, as you said last time!". So, Matt and I switched places, and he greased up. Then he worked on my asshole for a while. It was great - I loved it. Finally, he wiped his greasy hand dry and then directed his rod at my anus. Like I did with him, he went in real slow. I now knew what he was feeling. It still hurt - but not like that first time. Once he stopped to see if I was OK. I told him to continue. He finally was into me up to his balls. His balls felt pleasant rubbing me back there. Then Matt started to slowly go in and out of me. I made it to about the second or thir inward thrust (and he was trying to be slow and gentle), but I too had to ask him to please stop, which he did. We were both disappointed by our second failure. But we of course made up for it with our usual sexual activities. We didn't try anal sex again, until my 17th birthday - but that'll be a chapter unto itself. ***************************************************************************** Hope you liked this chapter. There'll be more. And Matt - Man if you're reading this - I miss your ass man! It was (and I bet still is) a beauty! Wish butt fucking had worked out for us - we'd have had a lot more fun!