1. First With a Monster


    Date: 7/31/2016, Categories: True Story, Anal, Oral Sex / Blowjob, Teen, First Time, Gay, Hardcore, Teen, Author: ILoveSexPeriod, Source: sexstories.com

    It was my first time with a man. I turned 21 the day before, and somewhere along my binge of top shelf alcohol, I ran into Jimmy Kristol. Ironically Jimmy’s rock hard dick was straining vainly for freedom from the boxer briefs he still wore. How I ended up here, in my bedroom, completely naked and seconds away from being fucked by a hung hot guy, I don’t quite know. It was around midnight when Jimmy approached me at the bar uptown. I was well intoxicated and my comments on his appearance and sexiness startled me and him as well. We got to know each other for a while longer until suddenly, he bluntly asked if I would do anything sexual with him. I weakly declined and Jimmy saw right through me. He saw the glint in my eye. Thankfully the awkwardness was broken by last call. I subconsciously wanted to have sex with him and without thinking I demanded he stay the night at my place. Happily agreeing, we left and headed home. The sexual tension was so tight between us on the drive that when I shut the front door of my home, I bee lined to my abode. “I apologize Jimmy. I don’t really know how to proceed. I’ve never practiced before…” I admitted shyly. Jimmy chuckled. Just do what the porn actresses do on film. Be sloppy yet passionate. I swallowed hard and pulled Jimmys boxers off, releasing a cock so impressive that porn talent searchers would fight for his contracts. He had mentioned earlier in the night that it was nearly 11 inches long. To make matters worse for my unaware and ...
    unprepared asshole, Jimmy’s cock was just as wide as it was long. I stroked him slowly and nervously, gaining confidence to start giving him head. I gave a big sigh of acceptance and started sucking on his tender head. Jimmy got a little impatient when I stayed at the tip for too long and decided to grab the back of my head, pushing me further down. I managed to get ¾ of his cock into my mouth before I couldn’t breathe and had to stop. Luckily, I didn’t gag. Remembering his advice, I quickly went from slow and shy, to gaining speed and getting sloppier, causing him to moan in pleasure. I sucked and sucked and sucked until my jaw cramped up and I was forced to take a rest. “Man! I never thought giving blowjobs would affect me that way. Its like I was in a trance and just couldn’t stop, not that I wanted to.” I said as I jumped onto my bed and laid on my side to face him. “So you liked my throbbing cock in your pretty little mouth?” he taunted playfully. “Now Its time to switch pace. Pick how you want to be positioned. Once your ready I’ll gladly take that virgin asshole.” His naughty talk only fueled me more. I debated for a minute between doggy style or on my back as he stood behind me. I chose the slutty doggy and assumed the position in the middle of my bed. Looking curiously behind me, I watched Jimmy lube the head and a little of his shaft with spit, then he rubbed some onto my puckered pink hole. I looked ahead as he aimed and guided himself forward. I expected a slow ...
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