When I woke up Saturday morning, everything hurt. My legs, arms, and back ached. Most important to this story, my anus felt annihilated. It felt wet and loose and emitted a wave of soreness that was hard to describe. In some part of my brain, it was a pain that felt good. After waking up and falling back asleep several times, I finally shook enough of the fog off to get out of bed. I drank some coffee, had a bite, and sat on the couch, where I would stay pretty much all weekend. I started thinking about how I ended up like this. I logged online to look at his profile and his dick picks, thinking with a dumb grin about everything that had happened the day before, which all began when this older man messaged me.
I had the whole weekend free to do whatever I wanted. Living with my parents while going to school, my life could feel kind of cramped. I spent most weekends out with friends, trying to keep busy, not really spending much time at the house. But this weekend, my parents were away at their friends. That meant I had the whole place to myself. More importantly I had time and space to lounge around and relax for a change. Having Friday off, I woke up with no plans and no idea what to do. I threw on TV and started messing around on my computer. One thing led to another and of course, before too long I was on a hookup site, slowly jerking off, looking at guys profiles.
I had been hooking up with an older guy for the last half a year here and there. I am a total bottom. Just under 6 feet tall, with a thin build. Blonde hair, blue eyes, and in really good shape with a tight ass and long skinny legs. I tend to attract masculine, buff, older guys. This may also be due to the fact that I say I am looking for masculine, buff, older guys in my profile! Guys who really take charge of the situation and make my mouth and ass theirs. Not really aggressive but certainly an assertive total top type of guy. The last guy I had been hooking up with, Ben, fit this to a tee. He was in great shape, a bit bigger than me, with a nice 7 inch cock that really hit the spot. Unfortunately, Ben had to move away when he was transferred in the company he worked for. Our last hookup was something special, but that's a whole different story :)
So I'm on this site and the horniness just keeps rising and rising. I'm naked now, looking through the profiles of older tops, thinking about riding their dicks, getting fucked doggystyle. All the sudden a message pops into my mailbox and of course I check it out. The title just says, "Hi!". Before even opening the message, I open the guys profile. Holy shit, he's a dream! First off, his picture jumps out. He's extremely handsome and strong with washboard abs. He has dark black hair and a nice patch of hair on his chest. He's 45, 6 foot 3, and total top with an 8 inch dick. His dick pics turned out not to do him justice. I thought that maybe he was exaggerating a little bit but it still looked comparable to my last guy so I didn't mind. I would turn out to be happily proven wrong on this fact later. He's the definition of tall, dark, and handsome. His profile says he's looking to hook up with an intelligent, slender, total bottom who likes to worship cock. Well, so far it seems like we are on the same page. I go back and open his message. All it says is, "You should come meet me for a beer after work and then we can head to my place and have some fun. I get off at 3. You won't regret it. - Lewis". Just like that. It wasn't even a question. He just gave me some advice. Basically, I should go meet this guy Lewis and then he would fuck me. I was sooo turned on!
To be honest, I didn't think I'd end up hooking up when I went online that day. I figured I'd hang out, maybe cum eventually to some porn or a story. I usually connected with guys and get to know them a little through e-mail before meeting up. But this was different. I thought to myself, why not? I had nothing to do. I had the whole weekend free. What better way to start then to suck some dick and get fucked by this beautiful man. We corresponded a couple more times. He told me to meet him at 3:15 at a bar not 10 minutes from my place. I still had like 4 hours to kill before I was to meet him there.
Before leaving, I made sure I was ready for a fuck. I always get these butterflies in my stomach during this process and my knees become kind of weak. I clean myself out, shave my ass smooth, and take a nice long shower so I'm squeeky clean. I also spend about 15 minutes opening myself with a small dildo just to get myself started a little bit. Next thing I know I was headed out the door to meet Lewis. I had on tight jeans and a tight shirt that show off my tight ass and compact body. I arrived at the bar. My head was in the clouds as I ordered a drink. and waited. Then I saw him come in, my stomach did loop de loops as we made eye contact. He was wearing a tight shirt that showed off his muscles and pants that were just the right size to be suggestive of how large his manhood was.
He waved to me and I waved back to confirm I was who he was looking forward. He had a huge smile on his face and I'm sure I did to. We greeted each other warmly, shook hands, and looked each other over. I saw him give me the up and down with his eyes. Approval flashed on his face and he excused himself to grab a beer. When he came back we made small talk initially. Filling each other in on what we were doing. He seemed to be amused that I was a college student figuring things out, living at home. I was showed interest in his job at an architecture firm and we chatted warmly. It definitely wasn't without flirting. Lewis was playful and expressive in conversation. We sparred verbally a little, as the sexual tension built. I naturally touched him at just the right times and let him know I was into him. We really were enjoying ourselves as we each had a couple drinks. At one point though their was a pause in the conversation and we were both about done with our beers. We both felt the time had come. Lewis said, "So, let's go to my place." I just stood up and gave him a coy, sexy look that said Let's Go. Lewis paid for our drinks and we got in his car and drove to his place. It was an expensive apartment building not 5 minutes walk from my parent's house. I had a good feeling about this whole thing!
The tension built as we rode the elevator. We got into his apartment and the tension just popped! He grabbed me by the waist and gave me a huge kiss on the lips which I returned with fervor. Before to long we were making out just inside his door. I took his shirt off and he took mine off as we tottered into his living room, making out. He sat down and pulled me down to straddle him as we made out. He ran his hands over my body, grabbing my ass and really checking out the goods. We made out like this for a bit. I loved the way his strong arms held me and how he kissed me with such conviction. I could feel his dick getting harder while I straddled him. It felt huge! It was this tube sitting under me as I gyrated. The feeling alone made me so much more horny. I had to get at this thing. He needed me to have it to.
Lewis broke the kiss. He said it was time to get down to business as he lifted me off his lap. "Time to get naked!", he said. I was more than happy to comply. we both stripped as we got a good look at other other naked in person for the first time. He was mouthwateringly hot. Just as buff as the pics and of course as handsome as ever. But his dick! Man his dick pics really did not do his cock justice. It was definitely the 8 inches he bragged about on his profile, if not more. And it was chiseled. Almost as if he worked out his cock. It was thick and veiny and perfect and had a light sheen that had built up while we made out. He looked me up and down and just nodded approvingly. He grabbed my shoulders, kissed me, and then started applying light pressure down. I got the hint. I sank to my knees where I my face was level with his powerful dick. I could see a tiny bit of precum starting to seep out from his slit. I thought, where else to start but there? I got my first taste of him as I stuck my tongue out and licked the precum of his tip. It tasted salty and sweet and perfect! I then slowly licked up and down his shaft before taking the head in and really getting down to business giving him a blowjob. After I was able to get pretty much all of him down my throat he knew he could go to town. He started moving his hips in a thrusting motion. Before I knew it, I wasn't pleasing him, he was pleasing himself!
Lewis started fucking my face. I was having trouble keeping up. I was slobbering and grabbing a breath when I could. When he sensed me struggling he would take his dick out and smack my face with it. This whole time he was giving me encouragement. Telling me how good it felt, how I was such a good boy, how I loved dick so much and it showed. Then suddenly he pulled out. I felt empty. He sat on the couch and told me to get on my knees on the couch to his side and suck his dick. I did so happily as the assault on my mouth let up and I was able to savor the flavor of his meat again. He grabbed some lube from a drawer in a side table and poured it onto my ass crack. He began massaging it into the crack, his fingers grazing my hole. This really got me going and my dick sucking intensified. Eventually he began plying my hole with his fingers. First his index finger made its entrance and started dancing around inside me. He began to finger fuck me, first with one finger, then with two, and then three fingers fully thrusting in and out with good speed. I was involuntarily moaning as I sucked his cock, exploring every vein and bump when he pulled his fingers out. I knew it was time to fuck.
Without saying a word I got up from the couch. He pulled me to straddle him again, just like when we first arrived. This time though, we were completely naked. I had both my feet on the couch with my ass poised above his cock. He had his hands on my hips supporting me, looking me in the eye with lust. I held his cock stable beneath me and slowly lowered myself. I felt the massive head touch my ass lips and I quivered from the electricity that it sent coursing through my body. I let gravity take over as the head slowly breached my sphincter. It resisted and then suddenly yielded to the invader as I pushed out to accept him. There was a flash of pain which quickly changed to a throbbing, slightly uncomfortable tightness. I let out a big sigh and a slight moan. I focused on breathing and getting used to his size. Easily the thickest thing I had ever taken in my ass. Once I felt the pain recede to a very dull pulse, I then proceeded to lower myself further. I have never felt so full in my whole life as I did during that initial plunge. I worked myself lower and lower. feeling every vein push past my asshole, my inner ring, and deep inside me. I was breathing so heavy and just moaning.
I went up and down the entire cock very slowly as Lewis told me how good I was doing, how tight my ass was. He kissed me and looked me in the eye. He was very pleased how this was going. He ran his hands over my body, grabbing my waist and my ass and helping me go up and down. I slowly began to ride his dick faster, letting out a little whimper each time I sank the monster into my bowels, its heat and warmth sending a warm wave of pleasure through my body. I began riding his dick hard as my ass relented completely and became used to the size of his dick. My ass began smacking against his hips as I fucked myself on him. We were both slick with sweat as we moaned and kissed messily and enjoyed the feeling of man fucking twink.
Lewis eventually became ready to take charge now that he knew I could really take his dick. He pulled me off him and made me stand. He got up, pushed me toward the couch, where I grabbed the back of it and arched my back with my knees on the edge of the couch, presenting myself. He lined his dick up and sank it into in one smooth, firm but not rough thrust. I shook with pleasure and gave a large moan. Lewis really started pounding me. I was practically yelling with each thrust into my ass. I was swearing and telling him to fuck me so hard, which made him somehow pick up the intensity. He pulled me off the couch, turned me around, and picked me up with his arms under my legs as I wrapped my arms around his neck. I had seen this one in pornos! My ass was hanging as he lined it up with his dick and let me drop right onto it. He sank right into me and began bouncing me up and down as I held on for dear life. We started making out as he fucked me with total dominance. He walked over to the wall and just started pounding me as I gasped and moaned and squealed. He told me that he loved how much I needed his dick. I told him I needed it more than anything.
He pulled me off the wall and walked me into his bedroom, his dick still planted inside me. This guy was so strong! He threw me on the bed and arranged me into doggy style. I arched my back for him as sexy as I could as he sank his dick into me again. He grabbed my ass cheeks and gave them a smack as he started to fuck me. The sound of skin smacking skin filled the room as his hips collided with my ass, sending waves of impact through my ass cheeks as he filled me with his dick. I settled into a kind of blissful stupor as he fucked me like this for a while. I focused on the feeling of his cock spreading me and making me his as I knew I was emitting all sorts of primal noises as he fucked me.
Lewis pulled out of me and turned me over onto my back. I could tell he was getting close. His eyes had the look of concentration of someone who is waiting for just the right moment to climax. He splayed my legs and lifted them up, exposing my red, beaten down asshole. He sank into me as he kissed me passionately. I wrapped my arms around him and held him close as he ravaged my hole once again. He pulled back from my embrace to make some space between us. I touched him longingly. He started going faster and I knew he was about to blow. He then surprised me by grabbing my neglected dick and jerking me furiously. My rock hard cock took no time to respond as a wave of orgasm overcame me and I began shaking and shooting ropes and ropes of cum all over myself. The contractions of my ass forced Lewis's dick out of me. He grabbed hold of it and while still jerking me off as I finished my orgasm he gave himself a couple strokes and yelled an expletive and a groan as he also began having spasms and shooting rope after rope of come all over me, some of which struck me in the face and open mouth. The rest covered my upper torso along with my own cum. He then collapsed next to me.
We lay next to each other, breathing heavily and soaked with sweat. My legs were still spread, exposing my hole. The feeling of the air on it after the pounded it took felt great. I could tell already I would be sore from the whole thing. Totally worth it. We started laughing and Lewis leaned in to kiss me. He told me how great it was and I agreed. I told him I thought he had made a great suggestion in his e-mail earlier in the day and he got a kick out of that. Eventually we got up, showered, got dressed, and promised to meet up again soon. At the door we gave each other a big hug and a nice little kiss before saying goodnight. I walked out slightly limping but with a huge smile on my face!
And so here I am! Sitting on my couch Saturday morning. My arms hurt from holding on to his neck as he fucked me. My legs hurt from riding his dick after he spread me for the first time. My back hurt from keeping it arched as I took a pounding doggystyle. And of course my asshole hurt from being stretched by the biggest cock it had ever taken. It was a great start to what would promise to be a very unproductive weekend, but the beginning of a great fuck buddy relationship!