(This story is 100% true and happened in North Carolina, everyone in this story is 18 and up)
I had just freshly turned 18 about 2 months prior to this story taking place and was still a virgin, I had considered myself completely straight up until a few years prior, when the idea of cocks and gay sex started to appeal to me, and knew in that scenario I would definitely be a bottom.
Having discovered the personals sections of Craiglist I decided why the hell not, I lived in a backwoods area of NC not near any real cities to speak of, I was an 18 year old, inexperienced, chubby, ginger bottom with a small uncut cock, I figured I would get no responses and it was just to amuse myself, I had attached two pictures of myself to the ad, simple mirror shots of my front and back.
I posted and waited, my tiny cock twitching with anticipation as I refreshed my email. The first replies were spam bots obviously, and a few people from far away that happened to be browsing.
Then I got a reply from a guy in a nearby town, about 20 minutes away, older guy, grey hair, face pic attached to the message he had sent me. He was very nice and struck up conversation about what I might be into trying and things like that.
We talked for a few days before I drummed up the courage to drive out to see him, I knew I needed to clean myself well, so used the shower head to really clean every inch of myself, shaved my little nest of pubes, and nervously made the 20 minute drive, heart thumping out of my chest the whole time.
I pulled up to his house and drove down the loong driveway, parked and got out, and he swiftly opened the side door to his house and greeted me warmly, he was HUGE…Im talking 6'6 and broad shouldered, I immediately felt small next to him. We walked inside, he offered me a glass of whiskey which I took, even though I was 18 he could tell I was nervous, and boy I was. We sat on the couch for a while and talked, I pet his cats and didn't bring up the subject until he said "You didn't come here just to pet my cats and tease me with that cute ass did you?" i giggled nervously and said no, he took me by the hand and guided me to his bedroom.
When we got in there he stood behind me and kissed at my neck, immediately this sent shivers across my body, he tugged my pants down, along with my boxers and lifted my shirt, I had my eyes closed and when I felt him press against me again he was also naked, his cock semi-hard and throbbing against the small of my back, and I remember letting out the sluttiest moan when I felt it press against me. He grabbed my hand and wrapped it around his cock and I started gently stroking it, he said "Mmm you've got soft hands, boy" and that just made me melt.
He kept kissing at my neck which is just like a drug to me, eventually spinning me around and starting to push on my shoulders "It's time to taste your first cock" he said, as I got on my knees and was face to face with his, huge to me, cut 6.5 inch cock, I was nervous and shaking, but mashed my lips to its side and slide my tongue across its length before taking the pronounced head into my mouth, tasting and smelling him. Making sure to not use teeth I slowly started to move my head back and forth along his cock, he was saying things like "Faster" or "God your lips are soft" as he started to buck his hips, my stiff little cock swaying between my legs.
This continued for a good 5 or 10 minutes and I was really into it when he tugged his cock from my lips, rubbed at the back of my head and told me to get on the bed, which I did quickly. Now prior to this I had told him I was obsessed with cum, and still am, and had thought about being filled with cum a lot. He told me if we meshed he would be ok with breeding me, told me he would claim my hole as his with his seed, but would start out safe with a condom. As I sat on his bed he moved over and mashed his lips to mine, kissing me hotly and pushing me down on the bed, reaching his hand between my legs and stroking my stiff little cock, using my leaking pre to lube my hole, slipping a finger inside quickly and making me pant.
He continued fingering me, opening me up, pulling his one finger out and licking it clean, coating his index and middle finger with his spit as he pressed two back into me and sliding deeper, I was blushing and writhing, twitching with nerves as he pushed his digits in and out of me, spreading them apart, working me open, I knew he wanted that wide tip of his cock inside of my hole.
Eventually he pulled them free and pushed them into my mouth! I sucked my musty taste off of his fingers as he reached to the bedside and pulled out some items, I was unsure what they were as I didn't see them, but I assumed it was condoms and lube, and I was partially right.
He then asked me to lift my legs up as high as I could, I obliged and he folded my legs back with his arm, squirting some of that cold lube RIGHT onto my hole, I must have whimpered because he just said "Cute". Then he worked some onto his cock and looked me in the eyes, saying "So…..about those condoms…I've decided not to use them" he smirked up at me, and I responded nervously, asking him about STDs and the dangers of it. He just shook his head side to side "None of that matters, I'm claiming your hole, now." and as he said that I felt the wide tip of his bare cock press to my hole, increasing his weight with his arm on my legs, holding me down. I must have whimpered like a whore because he just laughed and pushed hard, I remembered the feeling of it hurting, a LOT, a burning sensation, and then I felt his head pop in.
He kept his head there, inside my entrance and let me grow accustomed to it, petting at my legs and thigh, rubbing at my chubby belly, calling me "Good boy" and saying things like "Your hole looks good with my cock in it" before leaning a little more forward and starting to push the rest of his length inside of me, really filling me up, taking my virginity with his raw, unprotected cock.
I was writhing underneath him, loving every second of it as he used my hole, lost in the taboo-ness of having him in me raw, that I didn't notice just how badly my cock was leaking, dribbling a puddle against my crotch as he pushed that cock in and out my hole, slowly increasing with speed and pressure, he looked down and commented on my leaky uncut cock saying "You'll make a good sissy, is my cock gonna make you cum?" as he said that I felt a feeling well up behind my balls, something I had not experienced before, and I responded with a nod. I cant remember if I actually ever came from him penetrating me, but I know I leaked a LOT of cum.
He leaned over me and pushed his lips to mine again, forcing his tongue into my mouth and making out with me as he fucked my ass, kissing me for what felt like forever until he broke it and said "Going to breed you boy, claim this hole for my own cum dump" and he started mashing his hips against me faster, his balls slapping at my ass as he leaned down and kissed my neck again, hard, almost biting it, and he pushed his hips flush with mine, grunting in my ear as I felt his cock twitch and jerk inside of my hole, leaning his lips up and saying "Get pregnant, sissy" as he unloaded inside of me.
He stayed there for a while, his cock inside of me, twitching, softly kissing at my neck and my lips. Post nut clarity must have hit him hard, as he apologize and produced a clean STD test result from just a day or two ago, showing he had gotten tested after we started talking because he knew he wanted to breed me.
He eventually pulled out and I stood up, feeling like my inside had been moved around, as his cum started leaking down my ass and thighs, pulling my boxers and the rest of my clothes on, he kissed me goodbye and said he looked forward to next time, as I got in my beat up old car and drove home, leaking his seed into my undies.
Thanks for reading!