It was summer school. I was a horny bastard in high school. I remember jacking-off, on average, five to six times a day. I've always had sex with chicks in high school but never with guys, until one day I went on Craigslist looking for a car. I did this for about two weeks before I saw saw the Men seeking Men section and clicked on it. I was surprised how so many men in my area find sex this way. I responded to a few advertisements, but nothing happened until one day I decided to post my own listing around 10:00 P.M. While I didn't have any experience with men, I did know I was very attracted to older, muscular, 'daddy' types, so I posted an advertisement with the heading 'Younger for Older." I received about 30 e-mails within the next 30 minutes. I didn't like any of the responses except for one guy who described himself as: "'Daddy', 40 years old, 8 1/2 inch beer can thick total top, 5'9" tall, 200 pounds, thick muscular hairy." He was just my type. We exchanged e-mails and it turned-out he lived about half a mile down the street, but as I had school very early the next morning we didn't get to meet.
The next night he e-mailed me again, asking me if I was free to play at his house. My parents were still home (and in fact were still awake that night) but I was horny as hell, so I typed "Yes, can you pick me up at my house?" The answer came immediately "Yes, give me your exact address." I complied, adding "Give me half an hour to prep." "You got it" was 'Daddy's' succinct reply. I took a shower, cleaned my butt, used my mom's enema, and 30 minutes later he drove-up in front of the house where I was waiting at the curb. I got in his car and inwardly thought 'Woof'. He was very handsome and just exactly my type. I almost nutted just by looking at him. Three minutes later we arrived at his house. No sooner had the door closed behind us than 'Daddy' started passionately kissing me. We made out for about ten minutes before he lead me to his bedroom where he had me to get on my knees, and opening his trousers, presented me with his beautiful, thick and long cock. He grabbed my head saying merely "Open-up, boy." It was my first time sucking cock and I gagged each time I tried to go all the way down on him. Fortunately he quickly pulled me to my feet, removed my clothing, and positioned me so he could eat-out my ass for a long time, remarking in the process that I had the cleanest and tastiest hole he had ever tasted. I was in heaven! "You are extremely tight" he also commented, eating and fingering my ass for several minutes, preparing me for for his big cock.
He positioned me on my back, and, now fully naked, he lay on top of me. My legs almost automatically curled around his torso. Again we started making out again while his cockhead began to nudge it's way into my ass. "Condom?" I asked. "Sorry, all out" he replied, "We don't have to do this if you don't want to" Daddy said. "Well... I want it... But please put a condom on..." I replied. "I don't have any. Sorry. I'm clean. You don't have to worry" repeating "We don't have to fuck if you're not comfortable." "OK" was all I could manage as we began making out again. His hairy chest was dripping in sweat. I was overwhelmed by him. He was so hot and feeling his sweaty hairy chest on mine felt so good that I was oozing precum. Meanwhile his cock continued to nudge my ass, but this time I didn't object - I was determined to give him what he wanted.
Now, as I said, this was my first time as a bottom and he had a huge thick cock, so naturally his entry was quite painful but no way was I going to chicken-out. I was having the best time of my life! Still it took 'Daddy' about five minutes before his entire raw cock was lodged inside my ass. Yes, it was utterly painful, but damn, at the same time he felt good! Initially he fucked me slowly and gently for about ten minutes, then he pick-up the pace and for another thirty minutes he was pounding my ass very roughly. I moaned and yelled 'Daddy' with every stroke. Although still painful, gain it was painful, but felt unbelievably good - and to be honest, I was proud I was able to give him what he wanted. He fucked me rough for about half hour in every position. By this time my ass was bleeding - whenever he took his dick out of my ass, his dick was coated with my blood, and to be honest, while part of me wanted him to stop, another part did NOT want him to stop. I just wanted him to make me his bottom bitch, and that he did.
After over an hour of hard fucking, he looked me straight in the eyes and said "Tell me you want daddy's load, boy. Say it!. Tell me to breed that pussy!. Say you're daddy's little bitch!" And so I did and as I said the words, I felt his warm load blow up my ass. I felt it for stream inside my hole for as many as ten seconds. Talk about a heavy cummer! And I got every single drop of it.
After he had fucked, cum inside me and utterly used me, he told me he was too tired and told me to walk home. It was now 12:00 midnight. And so I did, walking home bowlegged and sore with his cum still inside my ass. Oh yeah - I came three times that night.
'Daddy' fucked me many more times - until I graduated high school and moved on.
PS: He was neg and so was I.
Edited by Hotload84, 09 November 2012 - 09:06 AM.