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Hangover sex. This is a true story with a few details and name change for discretion purposes.
I want to start by giving a little background info. I had met up with Dean a few times after meeting him online. We chatted for a couple days before meeting for the first time. When I finally decided to meet up, I drove 45 minutes to his house, parked down the road and knocked on his door. He let me in, we introduced ourselves and I ended up on my knees within minutes. Dean is 58 years old, his 6'2/250# frame towered over my 5'6/160#. He has a bit of a beer belly, which turns me on, a hairy body (except his cock), and his cock was proportionate to his body. It was 8 inches and very thick with a big mushroom head. Before we met I had told him I loved sucking cock and liked bottoming with the right connection. We were a perfection connection cause he was a total top. He had also told me he was very interested in fucking my tight bubble butt (my best feature) which I wanted too, but I kept telling him his cock was too thick.
Anyway, this particular time happened when I woke up pretty hungover from a night out with friends. As I am often hornier than normal when I'm hungover, I texted him and asked if he wanted to get together. It was 8am on a Sunday so I didn't expect an immediate reply but he texted right back saying he wanted me. I was staying in a hotel at the time while waiting to close on my house. I asked him if he could pick me up and bring me to my car (which I left at the bar after taking a taxi home) and then we could go back to my hotel room. He obliged and showed up an hour later. I hopped in his car and we started driving. He told me how glad he was to get my text and that he was extra horny that morning with a smirk on his face. That's when he unzipped his pants and fished out his half hard cock. I reached over and wrapped my hand around it.
"I've missed this big dick" He kept playing it off, telling me "it's not that big". I then pulled my already hard 7" dick out and showed him. My right hand on my cock, left hand on his as a comparison. I showed him how my hand can wrap all the way around mine but didn't even come close to wrapping all the way around his. While doing this, his dick kept growing. Finally when he was fully hard and we were at a stop sign in a quiet part of town, I leaned over and started sucking his cock. The way he was sitting and the fact he had on khaki's only allowed me to get about half of it in my mouth but I was really enjoying myself. The feeling of my tongue swirling around his big head, his moans and the thrill of being caught was driving me wild. In between moans, he'd talk dirty to me.
"That's a good boy, suck that dick."
You can imagine how bummed I was when he told me we were almost there and I should probably stop. I reluctantly put his dick back into his pants for him, keeping my hand massaging his bulge until we got to my car. I jumped out and told him we would continue this back at my hotel room. We practically raced back to the hotel.
As soon as we got into my room, I stripped naked. He followed me to the bed where he sat on the edge and I got onto my knees. I teased him a bit with my mouth and hand caressing his bulge on the outside of his pants before he dropped his pants. As his big thick cock sprang out, I took a minute to stroke and admire it. As soon as I took it in my mouth again, he moaned loudly. I loved hearing him moan. I was really getting into it when I heard him say "Are you finally gonna let me fuck that cute ass of yours?" and I said maybe. I just kept sucking while making eye contact.
He had asked a few times, but I was always nervous because his dick was so thick. But this morning was different. I wanted, so badly, for him to fuck me. I knew it was going to hurt like hell, but I'd get used to it. He reassured me that he would be gentle and I trusted him. I jumped up, gave his cock a few strokes and told him "I want you to bury this big dick inside me". He climbed up onto the bed with his back against the headboard and started stroking his cock. I walked to my suitcase and grabbed the bottle of lube and a towel and crawled between his legs. I poured a generous amount of it in my hands and applied it to his hard cock and my asshole at the same time. I climbed up his body and sat on his lap with his dick pressed between my asscheeks. I started moving my hips foreword and back stroking his cock with my eager hole. Teasing him. Now I've never been a kissing type of guy, but we started to make out as he was spreading my asscheeks.
"That's a good boy. Your smooth ass is so sexy. You're going to love this"
Once I felt like we couldn't take the teasing any longer, I lifted up, he spread my cheeks as I lined his cock up with my hole. I pressed down feeling his head trying to push past the resistance. So tight and his dick was so big. I kept having to stop to let my ass get used to the size. I knew he wanted it so bad and it was taking a little while, so I kept apologizing. Dean kept reassuring me that it was okay and that we had all day. "I want to spend all day here in bed with your big cock in my ass. And before you leave, I need you to fuck me harder than you've ever fucked before." "Son, when I'm done with you, you won't be able to walk right for a week" and he grabbed me tightly, pushing me down onto his cock as he kissed me deep. After a few minutes of trying, he was about halfway inside of me and I was in an excruciating amount of pain so I stopped and held still. I told him I needed to stop for a second to let the pain subside. He just held me there making out passionately. A few minutes passed and the pain had decreased substantially so I started rocking my hips back and forth. He just moaned into my mouth and pressed into me. I knew I was ready for it, whether it was going to painful or not. I slide off his lap, grabbed the lube and handed it to him. He pushed me on my side into the spoon position and poured lube between my cheeks and onto his cock. He had one arm underneath me holding my chest and the other massaging my hole with his dick before pushing past my entrance. I gasp.
"How does it feeling having my cock inside you?" "It feels so good. I can't believe how good this feels" "You haven't had the whole thing yet, you're going to love it baby" He turned my face and kissed me while moving in short slow thrusts.
"I'm ready for it sir" "You're ready to be fucked?" "Yes sir" With that, he pushed me forward onto my stomach, grabbed pillows to raise my ass in the air and poured a little more lube while teasing my hole some more. I felt him moving behind me, grab my hips and line his dick up to my hole. "You want this big dick in your tight hole? Are you ready to get fucked?" "Yes sir" "I want to hear you say it. Tell me. Beg me to fuck your ass" "Please sir, please fuck me. I want your big dick so bad" "Here it comes" He slid the whole thing in, in one quick movement. I cried out. Partially because of the pain, but mostly because I was in complete ecstasy. I felt his balls and hips pressed against me. I couldn't believe I had the entire thing inside me. He held it there for a minute or two not saying a word.
"Ohhhhh Daddy, please fuck me"
He stayed still, so I took matters into my own hands and started moving forward and back fucking myself with his cock. I heard moans of approval just as loud as my moans. A few more minutes of this and he grabbed on and started jack hammering inside of me. I'm screaming with every thrust, probably disturbing the neighboring room but I didn't care. I was finally getting fucked the way I had been wanting to. "Fuck. Fuck. Holy. Shit. You feel so good" "I'm getting close, boy" "Me too. Oh god you feel so good" I screamed even louder. I was not worried about the neighboring rooms. I was being fucked properly and it was making my cock spasm underneath me. I almost blacked out when my orgasm finally hit. I had never cum that hard in my life, much less without my cock being touched. This sent him over the edge. A few slow, deep strokes and he pulled out leaving me with a very empty feeling. I turn my head to see what he was doing. "Here it comes boy" I watched as he stroked his cock to an eruption all over my back and ass. He sprayed cum from the back of my neck down to my ass. "Oh my god that was amazing" "Fuck yes it was" He slaps my ass cheeks with his cock a few times and slid it back inside. I felt him scoop some cum off my back and reach around and feed it to me. "I know how much you love my cum" "Mmmmmmm. Yes I do. You taste amazing" I thought he would be done but his dick stayed hard inside me. It didn't take me long to realize we had already started round two. I looked back at him?
"Again?" "I'm not going anywhere"
I pulled off of him, told him to lay back again. I climbed back on top and slid down his pole. We made out as I slowly slid up and down on his dick. We slowly fucked like this for another 20 minutes or so talking dirty until I could sense he was getting close again.
"I want you to cum in my mouth"
I jumped off and laid between his legs looking up at him while I stroked and sucked him. Every time he'd tell me he's about to cum, I'd back off until he was ready for more. I wanted to prolong this as long as possible, but I wanted his cum so bad. After probably 15 minutes of this, I couldn't take any more. I needed his cum. I felt him tense up and backed off until just his head was in my mouth. I massaged his balls and pulled on his dick until he erupted in my mouth. He was moaning loudly with each spurt until my mouth was full of his sperm. I swallowed it and lovingly kissed and licked his dick as it began to soften in my mouth.
"For fuck's sake boy, you must've been hungry"
"I needed that so bad. Thank you"
Standing up, we kissed a few times and I walked to the shower to get cleaned up. When I was done drying off, I realized he left. Looking around I saw a note on the counter:
"Going to get some food, I want you naked when I get back"
What an amazing Sunday it was!