Date: Wed, 16 Feb 2022 20:06:31 +0000 From: The 1st Person Subject: Sneaking into Willy's Room It was starting to get late on a Tuesday night and I was starting to get a little bit horny. I hadn't had a good hookup in a few weeks, and there really wasn't anything new on the free porn sites that I went to. It was all mostly a rehash of things that I'd already seen. Though some of them were really good, you get bored watching the same thing over and over. You have to take a break from it for a while to make watching it worth it again. So I decided to go chat some on one of the few half-way decent chat sites that were left. Oh, how I miss the days of AOL and Yahoo chat rooms!! I logged in and sat back watching the endless scrolling of guys who wanted to jack off on cam together, or engage in the timeless art of phone sex. I was one of the few who had taken the time to fill out basic information about myself on the profile. It said how old I was, how tall I was and my weight, where I was from, if I was a top or bottom, and what kind of guy I was looking for. That was if someone started asking me these questions I could tell they hadn't taken the time to read my profile, and unless they said something interesting in a hurry were quickly on their way to getting blocked. I don't know about you, but I think it's pretty rude to start up a chat if you haven't read their profile. So as always, I spent the first little bit of time closing down Bot chats and blocking people asking me profile questions. As I watched the scrolling of the main room go by, I was also checking out the profiles of the guys that had cute pics on display to see if they were my sort of guys. Most were too far away though, or were looking for payment to send pictures or videos, or not interested in older men. But I did find a few that looked promising and sent a message to and was waiting for a reply back. I had been chatting with a few different guys for about a half hour when I got a message from a guy with the user name 'willysroom'. He didn't have a picture attached to his profile though, but he sent one with his introduction message and it immediately got my attention. "Hi," began his opening, "I read your profile and you sound pretty cool. I live in the same city too, but on the north side. Do you wanna chat some?" "Sure thing," I said back. "Few and far between I get to chat with someone from the area on here". Which was a complete lie. lol. The photo that he sent was a stunner. It was one showing a boy that was probably around 13 or 14 years old, laying on his bed shirtless, wearing only a pair of blue briefs underwear that had a pretty good size mound inside (possibly from being a little hard?), and a pair of round dark glasses. The picture was angled just enough so I could tell that his underarms were smooth, and had the silkiest looking legs going right up to the bottom of his underwear. He had a mop of dark black hair, and could only see one ear with an earring, so didn't know if he had a matching set. He had a Spongebob Squarepants poster hanging on one wall, with posters of the star baseball and football players on another. "How are you doing tonight," he asked. "I'm doing pretty well," I answered back. "I'm just relaxing at home right now doing some chatting and watching the TV. How about yourself?" While I waited for his reply I quickly went and checked out his profile. It of course started off by saying he was 18 (right?), that he was about 4'9" and 100 pounds. He said he liked to go camping and hiking, played baseball and PokemonGo. He liked watching scary thriller type movies and playing the old type video games at the arcade in the mall. He also said that he was gay, a virgin, and was attracted to older guys in their late 20s and up. So at just over 40 years old myself, I definitely qualified. "I'm just bored now, laying in bed," came his reply. "I really don't want to go to sleep yet. It's still early." "Well, I'll agree with you on the early part," I shot back, as it was only a few minutes after 9pm. "No video games to play or movies to watch?" "None that will take away a hard dick," came his reply. That answer made me have a good laugh. "I bet not," I replied. "So what made you think my profile sounded pretty cool?" I always like to know why when guys give answers like that. While I was waiting for his answer I couldn't help but stare at his photo. By now I had already saved it and reopened it with the pictures program so I could see it in full size, rather than the miniature that you get in the chat box. OMG it made my cock throb when I saw it full size. It was definitely a 1080p photo because it was so crystal clear. I could almost feel those smooth legs with my hands. I so wanted to run my hand over that blue mound and feel the hardness underneith. I could see myself swirling my tongue around the nipples on his smooth chest. The were almost the same color as his white skin to almost blend in. And I could feel my tongue making contact with his lips, feeling his part, and then our tongues touching. "You like to go camping and hiking too," his reply started out. "Pretty cool that you were a Scoutmaster. I want to travel too, but haven't gone anywhere yet," referencing my comment on having been to 40 of the 50 states. And cool that you're into younger guys too, cause I am one, lol!" "That you are! LOL!," I answered back, dreaming of my tongue running across the hardness in those blue briefs. "I just turned 13 two months ago," he said. "That's why I don't put a pic on my profile and it says I'm 18. If you want me to prove it, pick a number and I'll write it on a piece of paper and take another pic with it." The only real downside to chatting onine is that you never really know who you are chatting with. Even though the picture he sent was smoldering hot, he could really have been someone my age just pretending to be a teen. When it comes to chatting I don't really care unless you say something accidently that totally give you away. So when he said he was willing to prove it, I was up for the challenge. "OK then," I said, "But let's make it interesting. Write the number 322, but write it on your butt." "LOL! OK," he replied with a smiley emoji. "Give me just a minute." While he was doing his thing on his end I again went back to his picture and tried to imagine what he had in those blue briefs looked like. I was thinking that it was gonna be something like four to four and a half inches and it was going to be cut. Seeing that he didn't have any hair under his arms, I was betting that he was either still naturally smooth, or he had just the beginnings of a bush starting to develope, and that he was going to have a nice smooth ball sack. It took about two minutes to get another reply from him. "Sorry it took so long," he apologizeed. "It's hard to write on your own butt." I was laughing at the reply when the picture came through the chat. What came through looked amazing. He had taken off his underwear completely and managed to write the number 322 on his right butt cheek with a black magic marker. Then had taken the picture with him kneeling on his bed in a doggy position, looking over his right shoulder at the camera. When I saw it I nearly blew what I was drinking across the room. His ass was perfectly smooth with his cheeks spread just enough to see that pink hole between them. I wanted to put my hands on each of them and then just bury my tongue into that virgin treasure. "I hope that works for you," he said. "Oh yes it does!" I replied. "You are very hot for 13." "Thanks," came his reply with a blushing emoji. "Do you like boys my age," he asked. "I saw that you said you can travel to meet guys in the area. Would you want to meet me?" Again I nearly blew my drink across the room when I read that. I also nearly unleashed my cum from my own now rock hard cock. "Yes, I do like boys your age. Yea, I'd be up to meet sometime too. As long as you know a place where we could go." "Cool. I don't know any place where we could "go"," he said, "but I could sneak you into my bedroom once my parents fall asleep in a while. And I was hoping you'd want to do it tonight." "Wow, OK," I shot back. "How would I sneak into your bedroom?" In my mind sneaking in involved either walking through the the house, or somehow climbing up to a second story window. Neither of which sounded to appealing at the moment. "It's easy. We live in some pretty cheesy apartments. My room is on the first floor and the window is only about three feet from the ground. All I have to do is pop the screen out and you can step right in. One of my friends does it all the time when I invite him over." "Ah, sneaky little devil aren't you," I answered. "And your parents don't ever hear you?" "No. Their room is upstairs and on the opposite side, so they wont hear a thing. Once they go to bed they wont get up till their alarm goes off at 6am." "I know the feeling! LOL," I said. "What all did you want to do then," I asked with a twitch in my cock. "IDK. What ever you want to do really. I've never done anything. But I really want to try kissing, sucking a dick, and getting fucked. "Well, that covers about everything," I said. "As long as you don't get to loud and wake your parents with the fucking part." "Yea, for sure. But the way this apartment is I could probably scream and they wouldn't hear it." "That's a bonus for sure then." "So would you want to come over then? I figure if you came at midnight they would be long asleep." "OK then. How would I let you know I was there?" "If you park about a block away I can meet you on the street corner. Then it's just a walk through a whole of bunch of trees and you come right up to my bedroom window." "OK," I said. "Then I just need the address so I know where I'm going." "Here it is then," he said. And though it was only text, I could almost feel the excitement in his fingers as he was typing it out. "How big are you if I can ask?" "Well, you did just ask," I replied jokingly. "I'm 8" and I'm cut." "OMG that's big!" came his comment. "That's like twice my size. And I bet twice as wide too." My cock leaked a bit of precum on that comment. I'd been resisting pulling my cock out to jerk off to his picture while we were chatting, and now I was glad that I did. But it was still rock hard. "I hope it feels good in my butt," he added. "I'm sure it will," I said, trying no to cum free hand as I thought about my cock going between those smooth cheeks and into that tight pink hole. "I'll make sure I bring plenty of lube to make it go in easier too." I also thought I'd bring a bottle of poppers to have him inhale too to make it easier. I put his address into the mapquest and it said he was about a thirty minute drive away. So with our meet time set at midnight, I figured I'd leave my house at 11pm to give me plenty of extra time. Then I could just read news or something on my phone till our meet time. Since we had been chatting for about about an hour it was a little after 10pm at that point. "Alright then," I said starting to close up the conversation. "I'll start driving up at about 11pm. I'll keep the chat room open if you need, or want, to call it off. I'm gonna go take a shower and get something to eat now to get ready, OK?" "OK," he replied. "I'll put on another movie to wait. My dick is so hard already. LOL" "Great. Just don't fall asleep." "Oh, I wont do that for sure!" "Alright. See you in a bit then." "Bye!" ********** PART TWO ********** The drive up to the boys house was pretty uneventful. I managed to keep my dick soft on the way by listening to the radio and having the window down, feeling the cool night air blow againt me. My GPS brought me right up to the corner that the boy had told me to park at. As I was getting close I saw there was a person sitting at the corner right under the stop sign. I wondered if this was the boy that I was supposed to meet. Our meet time wasn't until midnight, and it was just now a few minutes past 11:30pm, so he must have come out early to wait. As I started to slide over near the curb to park, the person under the stop sign got up and backed a few steps up onto the sidewalk. I pulled to a stop with enough distance between the car and the corner so I wouldn't get a ticket for parking to close. As I did, the person started walking up the sidewalk towards me. I shut the car off and got out, making sure to lock the doors, and walked around the front end to the sidewalk. When I stepped up on the sidewalk, I could see that the person was a young boy for sure. As he got close enough I could definitely tell that this was the same boy from the pictures. "Are you looking for willysroom?" he asked. His voice sounded like it was right on the brink of the puberty change. "Yes, I am," I answered, knowing that I'd found him already. He smiled a bit and said, "You found him." He had pulled on a pair of elastic band soccer shorts, a tshirt, and shoes with no socks, to come out and meet. He looked even better in person than he did in the photos, even if it wasn't as light where we were standing. "Follow me and we can get to my bedroom." "Lead the way," I said. He turned around, but instead of leading me down the sidewalk and around the corner, he led me onto a little path that was almost in line with where I had parked. We went about fifty feet down the trail that was between a tight grouping of tall trees until we came to the corner of his apartment building. The building was backed up to a deep ravine that looked like it went down a good fifty feet or so and was at least that much across. It left a walking path of only about three feet wide between the building and the ravine's dropoff. His bedroom window was about ten or so feet in from the corner and had a milk crate sitting upside down on the outside of it. The boy stepped on it and climbed through the open window, stepping on another crate on the inside and then stepping to the floor. He turned around looking at me and said, "See, not to hard at all." I gave him a big smile in return and couldn't believe what I was about to do. I'd snuck out of my house plent of times when I was a kid to go meet up with friends, and even had a few of my sneak in to hang out. I'd snuck out plenty of times as well to bike down to the park that was known for guys cruising at night so I could suck a dick or get mine sucked. But I'd never snuck an older guy into my own bedroom for sex. This was going to be a first. I was already here, I thought. I was standing outside the boy's bedroom. "What the Hell now," I thought and stepped on the crate and went through his window as well. As soon as I was in and had taken a few steps away from the window, the boy went to it to shut it, and then shut the blinds as well. He turned around then and gave me a huge smile. "Welcome to Willy's room," he said. "Thanks man," I said, walking over to his bed and helping myself to a seat on the edge near the corner, giving him plenty of space to pick a place for himself to sit down as well. I could tell that he was pretty nervous and didn't know what to do now. He was figity and wouldn't sit down. He started showing me things that were around his room and talking about them. I knew I was going to have to take the lead to get anything started, or I doubt it would have. "Why don't you take your shoes off and come over here," I said, indicating a spot in front of me. He kicked off his shoes with his feet and came over to the spot where I was holding my arms out in front of me to show. He was now standing just inside my open legs. "Right here," he asked. "Yep, that's perfect," I replied. I moved my hand gently to him and rested them on his hips. "Here are the rules," I said. "If you change your mind at any time, or don't want to do something, say stop and I'll leave. Otherwise, just relax, and have fun." "OK," came a whispered reply. ********** PART THREE ********** I started to lift his shirt up, slideing my hands up his sides the whole way. Instinctively he raised his arms overs his head then leaned over enough so I could pull his shirt off. His beautiful chest was now bare in front of me. His height was just perfect enough so his nipples were right at mouth level. I spread my legs open as far as they would go and pulled him a step closer to me. I leaned in, breathing in his sweet scent, opened my mouth, and kissed his nipple lightly. He let out a soft moan and he dropped his arms straight down his sides. I moved my hands around to his backside and lowered them to cup his ass through his shorts. His body started to shake, so I told him to rest his hand on my shoulders. The feeling of his soft hands on my body really got my dick excited. I took a quick break from his nipples to take my own shirt off so I could feel his hands on me skin to skin. I took a few more minutes moving my mouth from on nipple to the other and then back again. Each time gently kissing it, then swirling my tongue around his hot points. I dared to see what he would do, so I took one of his nipples between my teeth and gave it a gentle nibble. The sounds he made were just intoxicating. While I added a little nipple nibbling to the menu, I hooked my fingers inside his shorts, between them and his underwear, and started to lower them down. After a slow ride down his hips I let them go to fall to the floor. I looked down at them and asked with a little laugh in my voice, "these are the same ones you were wearing in the picture, aren't they?" "Yea, they are," he answered, also with a big smile and a light laugh in his voice. I stood up from his bed and told him to lie down on his back with his head on his pillow. When he had done that, I went to the foot end of his bed, reached out to take hold of his ankles, and spread his legs wide, but not to wide that it hurt. I took a moment to kick off my own shoes and socks then, and watched as his eyes got huge, and glued to my crotch, as I undid my belt, button, and fly, and lowered my shorts till I was standing there in just my own tight boxer briefs. I left my boxers on yet for the time and layed down on my chest between his legs, putting his underwear under my head. He was intently watching me with those cute round glasses still on as I stuck out my tongue and licked his rigid cock from it's base all the way to it's head through his underwear. I thought he was going to explode right there, but he didn't. I opened my mouth and ate at his cock moving my mouth slowly from base to head. Once I got to the head of his still hidden cock, I pulled his underwear tight around his hardness and sucked on it's head creating a nice wet spot on the blue fabric. I hooked my fingers inside his underwear then, and lifting them just enough not to get hooked on his cock, lifted up his butt and and pulled them down the length of his legs and off his feet. My gorgeous boy was now laying totally naked in front of me with the exception of his glasses. I spread his legs again, and got back to where I was, pulled that hardness down so it was pointing at the ceiling, and engulfed his cock with my mouth till my lips were resting on top of his balls and stomach. Again, the moaning, and cooing sounds he made while I gave him his first blow job were amazing. Every so often I'd catch him as his eyes rolled back a little, and watched him curl his cute toes while gripping the side the of the bed. I could tell that he was in absolute Heaven. I reached up his chest with one hand to start playing with his nipple as the other hand moved down to to take hold of his ball sack. I didn't work my mouth fast and furious up and down his cock, but just nice, smooth, gently paced bobbing, stopping ever now and then to swirl my tongue around his cock head. We continued on like that for a good long time, and though I could have stayed like that for a longer time yet, my own cock was dying get out my boxers and feel his lips around it and the warmth of his mouth. I got up off the bed and told him to stand up too, then took his position laying down and told him to come and lay on top of me. As he did, I pulled him up so we were face to face, put my hand around the back of his head, and brought his lips to mine to kiss. I ran my tongue over his lips and he parted them so I could let my tongue meet his. His mouth was so tastefull, and he was a wonderful beginner at the art of kissing. I kept one hand on the back of his head as I moved the around him and dropped it to his ass. The feeling of his cooing as my hand went over his ass was almost enough to make me shoot. I placed my hand on his ass so that my middle finger was able to run up and down the length of his crack. We continued to kiss as my finger explored deeper and deeper into his ass until it found, then came to rest, on his pink, virgin, hole. He broke our kiss and buried his head into my neck, breathing hard, and moaning as he enjoyed the incredible first time experience his body was getting. Without him seeing, I wet my finger with my mouth and placed it back on that tight doorway. I started to give him the slightest amount of pressure and felt his body react. He body tightened, his head buried over my shoulder even more, but was surprised to feel that, ever so lightly, and probably without him even knowing he did it, his ass pushed back onto my finger rather than retreating. I got just a fingernail's length into his opening before running my hands up his sides and pushing his body back so we were again face to face. He had taken his glasses off while burying his head over my shoulders so he reached out to grab them and put them back on. He just had a big smile on his face that told me he was enjoying things so far and wasn't ready to stop. He didn't spend any time at my chest as he slid his body down between my legs, and didn't work my cock with his mouth through my boxers as I had done to him. He simply took hold of the sides of them, and being careful to lift them over the tip of my hardness, pulled them down, rolling over on his side to get them down the length of my legs and then off. Willy rolled back over so he was laying between my legs again, grabbed ahold of my cock right at the base and said, "Damn. I didn't imagine it to be so big." "Well, just do what you can," I said. He gave a little laugh then leaned forward and took his very first cock in his mouth. "Mmmmmm," he moaned and he went down about half way on it. He started in at a very nice pace of going about half way and then back up to the head. Down again, and then back up. "Mmmm Hmmm indeed," I sighed as I watched him work my cock. His young, inexperienced, warm mouth just taking me to cock heaven. "Can I record you giving me your first blow job?" "Sure," he replied with a big smile on his face. I had him quickly pass me my phone that was in my jeans pocket before he returned to work on my cock. I got my camera set on my check so it was looking down my stomach at this beautiful young, glasses wearing, boy, occasionally looking up at me enjoying having his first cock to suck on. After a few minutes I reached down and put a hand on the back of his head to run my fingers through his hair as his warm mouth kept its pace on my cock. Then, without warning, he took his hand off my cock and took all of my cock into his mouth until his nose was now buried into my stomach. "Oh fucking God," I nearly screamed as I realized that this virgin boy had just deep throated my cock and wasn't gagging. He backed all the way off my cock after a few seconds and giggled as he wiped the saliva from his lips. "Do that again," I said. "OK," was his only reply as he took my cock into his mouth again and went down deep. "Fucking God," I exclaimed. I put my hand on the back of his head again but this time held him there for as long as I could before he had to take a breath again. "Fuck, I'm glad I got that on cam." He took a breath again and went back to the normal, rythmic, up and down pace, every so often going down deep again while I held his head hard against me. We kept on like that for a few more minutes before I got up to have him change positions. I told him to roll over on his back with his head at the foot end of his bed. I pulled him down the bed then just enough so his head was hanging off the end. "Try sucking my cock like this," I told him. Again, "OK," was the only thing he said. I put my cock head up to his now upsidedown lips and he opened up wide. I watched as my cock disappeared into his mouth, then saw his throat expand as my cock went deep into him. I told him to breathe through his nose as much as he could as I started to fuck his throat. The sight of this boys throat expanding and contracting as it took on the width and depth of my cock was an amazing sight. I held my camera with one hand having it record each thrust down Willys throat. My other hand was at his neck, rubbing his throat as my cock expanded it. Every so often I'd give his throat a deep thrust and just hold my cock there. He would reach up and grab my sides with his hands trying to push me away as I recorded his toes curling up, and his feet start to kick as he was getting desperate for a breath. I'd back my cock out of his mouth and record his face as he panted for breath, wiping away the saliva. "Ready?" I asked him after a few seconds. "Yea," he replied, and back down his throat my cock went. I'd stroke his throat with my a cock a half dozen times or so before holding it hard deep in him again. I'd wait again until his hands started to push me off, his cute toes beginning to curl again. Then when his feet started to kick would I back off. Each time giving him a shorter and shorter amount of time to catch his breath before sending my cock deep down his throat again. We must have fucked like that for a good ten minutes or before on one of his breath catching breaks he said quickly, "Fuck me for real now, OK?" How could I deny this virgin boy his cherry popping? I told him to flip around so he was sitting on the edge of his bed. I had him lay back as I lifted his legs up and scooted him so his ass was right at the edge of his bed. I quickly reached into my jeans that were on the floor and grabbed both the bottle of lube I had brought, and the bottle of poppers for him to inhale to make the fucking a little easier. Fortunately he knew what the poppers were and what they did so I didn't have to explain it. He took a big huff of the poppers in each nostril as I lubed up my cock good and wet. I dribbled some of the lube on his ass and ran two fingers deep into him to make sure he was good and covered. He let out a deep, hard, moan as my fingers worked the inside of his ass for about a dozen strokes, his toes curling in on each in-stroke and then relaxing when I pulled them out. I grabbed my camera with one hand while I held back one of his knees with the other. "Hold your other knee back," I told him. I had my camera recording his face as I said, "I'll record my cock going into your ass. Your very first fuck." "I so want it," he said with an absolute look of lust that I could tell meant he was ready. I had him take one more hit off the poppers as I put the head of my cock against his beautifully tight, pink, virgin, hole. He laid the bottle down next to him and took a good grip of the sheets in preparation. Then with our eyes locked, I started pushing my cock into that virgin territory. I watched through the camera as the head of my cock disappeared into his ass. Willy wasn't moaning, he was just breathing hard as he continued to accept my cock into his young ass. I had to set the phone down as I leaned down close to him, chest to chest, and started to kiss him as my cock continued to penetrate him. I knew my cock was about to break through and sink deep into him, wrapped my arms around him as he wrapped his legs around me, and went mouth to mouth in a big kiss as my cock broke through. Willy's eyes flew open as my cock sank deep into the warmth of his ass, his deep moan traveling from his mouth to mine. His arms and legs went into vice grip like holds on my body as his ass got used to the invasion. His body finally relaxed after a few minutes though he was still breathing hard. I backed off of him again so I was standing on the floor with my cock deep in his ass. I put my hand behind his knees and started to fuck him in earnest. Not only was Willy a natural at cock sucking, he was a natural bottom as well. His ass was willingly accepting my entire 8" until my balls were slapping against his ass. He was moaning loud enough on each stroke that I worried a little that his parents might hear. He said not to worry though, and just to keep fucking. I was getting tired of standing after a bit and pulled out of him just long enough for me to lay on my back and tell him to straddle me. I had him kneel over my cock and sit down on it. He put his hands on my shoulders as I felt him take my cock back into his ass. I put my hands on his ass as I helped him to ride my cock. It was a wild sight to watch this young, newly broken in, boy ravage his own ass by bouncing up and down on my cock with long deep strokes. I reached up and took ahold of both sides of face while he was leaning on my chest as I asked, "Does that feel good? Are you enjoying your fucking?" "Yes," came a whimpered reply as he continued to bounce up and down on me. "I love it so much. Will you cum in me?" "Absolutely," I replied. I pulled him off my cock and had him lay on his stomach. I got behind him and between his legs and reinserted my cock into his warm depths. I took hold of his hips as I was thrusting forward, feeling him pushing back onto my cock as well. I continued to pound this kids totally accepting hole as he continued to whimper beneith me. I was getting close to cumming, which was perfect timing as between whimpers he said he was too. I pulled out of him one last time to flip him on his back again to how we had started, and thrust my cock deep into him again. I started to fuck him nice and hard, long deep strokes, and he grabbed onto his cock and started jacking himself off. We were both huffing and puffing as my cock stroked his ass, and his hands stroked his cock. I had my hands on his ankles and spreading his legs wide as he said the magic words. "I'm cumming," he said as he threw his head back and yanked at his cock as hard as he could. The moment I saw cum start to fly out of his cock I let him know I was cumming too and just held my cock deep in his ass as I felt jet after jet of my cum start to fill his now throughly fucked ass. I let my cock stay in his ass as we both worked to catch our breath from the good fucking that we had just finished. "So how did you like that," I asked as I pulled myself out of him and stood up to start getting dressed again. "That was fun," he said with a big smile on his face making his move to pull on his underwear again. "I'm glad you liked it," I said as I stepped back into my own underwear and pulled my jeans on. "I had fun too." "Maybe we can do it again sometime." "Maybe when you're parents aren't sleeping upstairs," I said sitting down to pull my socks and shoes back on. "Right. For sure," he agreed as he pulled his own shorts on. "You know how to get ahold of me if you do," I said as I pulled my tshirt on and stepped towards the window. I opened the window up as Willy was still sitting on his bed, and stepped through to leave. I closed the window behind me, gave a wave to Willly who gave a big smile and waved back, and walked back through the trees to my car. I'd had sex with several virgin teens in the past, but this one is going into the top five I thought as I started to drive off.