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It had been several months since I first sucked off my best friend after a high school football game. We had continued to meet up on weekends and during the week too for blowjobs. We were constantly sucking each other off and getting our bellies full of cum. One day after school he came over and we had the house to ourselves. We were hanging out on my bed listening to music when things eventually turned to rubbing each other's hard cocks through our shorts. It didn't take long for us to get naked and start 69'ing. I loved sucking his cock because it was as thick as a beer can and a good 9+ inches long, beautifully uncut too. As I was sucking his dick and massaging his balls with my hand he opened his legs and I naturally started to massage his taint and slowly made my way to his hole. I started rubbing his hole with my finger which produced slight moans from his cock-filled mouth. That was all the encouragement I needed to put my finger in my mouth and coat it with spit and try to get my finger into his tight hole. There I was sucking a fat cock, fingering his tight virgin hole and being blown at the same time. I was incredibly horny and kept working his hole with my finger and decided to try another finger, he really moaned when I slowly forced a second finger up his hole. I knew his moan was partly from pain and partly from pleasure. After awhile of all these different simulations at once, he pulled away from me. I was laying on my back and he straddled my waist and grabbed my cock from behind. I had no idea what was happening. Because what was about to happen, I had never even thought of doing. My cock kindof started hurting. That's when I realized he was putting his weight directly onto my raging hard dick, trying to get it up his virgin hole. It was so tight and had so little lube from just my spit. He got almost my whole cock inside him before I truly understood I was fucking his virgin hole bareback. He rode up and down on my cock maybe three times before I blew a huge load of cum up his ass. Which fortunately lubed him up on the inside much better. I'm a multiple cummer and don't get soft, so I took the opportunity to enjoy his wet virgin boypussy. I pushed him onto his back and started ramming my cum-lubed cock into his hole faster and faster. In this new position my rock hard curved cock was hitting his prostate and his eyes practically rolled back in his head. His fingers dug into my back as I continued ramming my rod into his still tight hole. His breathing became labored and with a loud series of moans his huge dick started spraying both of us with hot cum which immediately set me off again and I dumped yet another fat load deep up his once virgin hole. 

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Guest Lempriere
Posted

Great story. Hope you had many similar adventures afterwards.

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