Indiscretions in the Dark
Since I received a lot of positive feedback about my first story, Summer Camp Submissive Awakening (which I promise I will get around to finishing! Life got a little hectic lol) and a lot of interest in me writing some of my own experiences, I decided to share a fairly recent one. There will be a sequel story about the second time I hooked up with this guy, but it won't be a part 2 as I had more than one hookup that night lol...
The following is a true account of a recent and very satisfying encounter, although I've changed his name and background a bit to protect his identity.
It was turning out to be a pretty boring night. Nothing great on TV and I couldn't really focus on picking something out on Netflix. On top of that, I was really horny, so I decided to watch some porn. Of course, the more I watched and edged myself, the hornier I got, and the more I wished I was one of the bottoms. I decided what I really needed was to get my hole worked really good, so I got out my dildo and a bottle of lube. I'm a pretty chubby bear, so it's not always easy for me to finger myself, but I slathered the dildo really well after sticking it to the wall of the shower and gently began pushing my tight asshole against it. I was breathing deeply and focusing on relaxing and letting my backdoor open and take in the full length of the firm silicone member. I had had a little bourbon earlier and was lightly yet pleasantly buzzed, which made it feel great as I teased my little pink nipples to hardness by flicking them with my thumbnails.
I felt my hole begin to open up and accept the stiff dildo and relaxed and pushed back more, letting another inch or two slide in before pulling forward off of it and applying more lube. My balls were tight and my 6-inch cock was half hard as I eased back onto the dildo, slowly opening myself up and taking in the entire 7 inches a little at a time until the firm silicone balls were pressed up against my own sack. I stayed all the way in for a moment, getting used to the fullness, and then slowly and gently started fucking myself, moving my firm, round, chubby ass on and off the dildo and continuing to tease my nipples. I squeezed and caressed my chubby man tits as I did so, imaging someone's strong hands playing with them while fucking me from behind. As amazing as it felt, I knew I needed more. I needed a hard cock in my ass for real.
Pulling myself off the dildo, I stuck it upright on the floor of the shower and gently sat down, taking it all the way in to the fake balls much easier now that my ass was well-lubed. I pulled up an adult dating app and modified my profile to reflect what I was looking for, then began browsing to see who was near me that fit what I was looking for.
As a bottom, I have something of a love-hate relationship with anal. I love it when it's done right and I've had some tops who've made me want to propose marriage they were so good. I've also had some really lousy ones who make the age-old mistake of forgetting (or not caring) that the ass is not like the pussy and try to just jam it in and hammer away from the start. So when I'm in the mood to have another guy stick his penis in me, I've become fairly picky. After exchanging messages with a few guys who seemed to be of the "just start jackhammering" mentality, I got an interesting message from a guy who's screen name was Kofi, which I recognized as a common name in Ghana. It read, "Hello dear, would you like to come over and make love? I love chubby men like you." I looked at his pictures, and he was a handsome black man in his mid-20s with a wide, inviting smile and lustrous, very dark skin. He was a little stocky with a bit of a belly, which is fine by me as I prefer other chubby guys. After exchanging messages back and forth for a few minutes, during which he kept referring to me as "sweetie", "honey", "dear", "baby", etc - which I found to be quite charming - and exchanging some pictures, we decided to meet for a hookup at his place. I'll admit, he was pretty irresistible, being handsome, sweet, charming... And of course, since we'd exchanged nudes, possessing an absolutely beautiful cock. It was a little hard to tell in the pics, but it looked to be about 7.5" long and curved to the left somewhat, which was fine by me as I don't usually enjoy getting fucked by much bigger than that.
He lived a fairly short distance away, which was good since I was still buzzed and didn't want to go far. I ordinarily don't drive even if I'm just buzzed just to be safe, but he was only a couple of miles and I was horny like a cat in heat to get fucked by this charming guy, so I pulled on a pair of basketball shorts, a t-shirt, and a pair of boat shoes and within five minutes I was pulling into his apartment complex. I messaged him that I was here, and he replied, "Ok baby, I'll come let you in." I got out of the car, and walked towards his door, which opened just as I got to it.
Wow. He was even better looking in person, closer to 5'10" than the 5'8" he'd stated in his profile. His beautiful dark skin glowed in the moonlight, and his eyes were warm and friendly. "It's good to meet you, honey", he said quietly in a deep, sonorous voice with a very sexy accent. "Please come in, but we must be quiet, honey, since my mother is asleep in her room." I nodded, and he led the way up the stairs to the second-floor apartment. Despite my size, I can move very quietly - all those years playing manhunt in the woods in boy scouts were paying off, as I was about to reap the rewards of a very different man hunt. Sneaking through the dark apartment, knowing I was about to have sex with this hot guy was turning me on and making me want him even more. I was feeling like a dirty little slut being snuck in after dark to get fucked, and I was loving every second of it.
He eased open a door and took my hand, leading me into a small but tidy bedroom. The curtains were drawn back, allowing enough light from a street lamp in the parking lot to enter to get around the room without running into anything, otherwise it was very dark. He didn't switch on any lights, either, which made it feel very intimate and very naughty at the same time.
"Ok baby, now you take your clothes off for me", he said. He spoke the words gently and softly, but still I wouldn't have ever disobeyed. There was something about his kindness and gentlemanliness that made me want to be completely submissive, so I quietly replied, "Yes, honey" and quickly stripped down while he did likewise. I looked over his stocky frame in the dim glow and felt my cock rising up to attention. His own cock hung half hard in between his legs, and looked absolutely delicious. He walked over to his bed and laid down on his back in the middle. There wasn't really room for me since it was a twin-sized bed, and I was a little uncertain what to do when he made the decision for me.
"Now, baby, you suck to get me hard". Again spoken so softly and gently, but I felt so enthralled by him that again I murmured, "yes honey", and leaned over the bed. Taking his half-hard cock in my hand, I lifted it up and lowered my head down, drinking in his masculine, musky scent as I wrapped my lips around the head and began to work his shaft with my mouth. As I felt him get firmer and longer in my mouth, he let out a quiet "mmm" and gently placed a hand on the back of my head. No pressure, not pushing me down to force a deepthroat, just resting it there. It was such a subtly erotic thing for him to do, to gently assert his dominance without being pushy or forceful, that I almost came from it. It made me feel weak in the knees the way he was being such a gentleman, but still letting me know that he was the top and I was going to do what he told me.
His cock filled out while I sucked it. My earlier estimate of 7.5" seemed to be pretty accurate, and it was a little thicker than average, but not absurd. A nice big dick for sure, but the perfect sort of big. After a few minutes of sucking his dick and enjoying the smooth skin sliding in and out of my mouth and the warm, savory, slightly salty flavor of it, he softly said, "Ok, honey, that's good; now I make love to you." He stood up and walked around behind me, then put a hand on my hip and the other on my shoulder and walked me towards the bed, while his deep voice purred in my ear, "Go bend over the bed and spread your legs for me, baby, so I can make love to you ass."
Again, I complied without hesitation, feeling completely aroused and completely submissive. This time, though, I said, "Yes, Daddy". He reached down and gave my ass a firm squeeze as I bent over. He must've noticed the telltale shine of the lube because he asked if I used enough. I told him I had used a lot loosening up my ass with my dildo but that I had the bottle in my shorts if we needed. He began rubbing his big cockhead up against my hole, getting it slippery with lube, and said, "Let's see, dear. I'll push you open slowly and start gentle". Good Lord, this man knew how to sweet talk. His dickhead felt hot and wonderful rubbing my hole, and I started to push back a little while relaxing as I had done with the dildo at home. He guided his cock to my hole and began to gently push. It had been a while since I'd taken a cock as big as his, so it was a little painful as he pushed it in. I gasped a little as a jolt of sharp stabbing passed through me, brief but not fun, and then it went away. "Easy, Daddy", I said, "just let it loosen up, it's almost all the way open." "Okay baby, I will go slower, honey", he whispered. He had his head and the first inch or two of his shaft in when I felt my hole relax a little more, having gotten used to the stretch. He must've felt it, too, because he applied more pressure now - not really hard, but definitely determined now to get it all the way in.
I felt like I was having a bus parked in me as his stiff cock now slid smoothly into me up to his fairly large balls. There must've been something about his curve to the left that stretched different parts of my anus as he slid it in, because it felt way thicker than it was. Once he was all the way in, he leaned over my back and murmured, "Take a minute to get used to it, honey. Then we'll make love."
True to his word, he gave me a minute or two to get used to his big dick opening me up before he slowly started to hump my asshole. He began with really slow and easy thrusts, sliding it in all the way to the balls and then out until just his lead was in. It felt incredible. He was an absolutely amazing top and worked his pace up slowly, strong hands on my hips, working my hole with his big dick and very skillfully swiveling his hips to grind my insides just right.
Over the course of the next ten minutes or so, he truly did make love to my ass. It was absolutely blissful, and I found myself leaning back to receive each thrust. I was in heaven as his big dick massaged my prostate, my cock hard and rubbing against his sheets as he humped me to against the side of his bed. His thrusts were becoming deeper, harder, and more frequent, and I was taking his cock like a good little slut, letting him take my hole the way he wanted to.
He was definitely getting close, since he was giving me a good fucking, when that sexy voice growled softly in my ear, "Honey, can you take it harder for me?" I have no idea how I didn't cum right there because it sounded so sexy, so I whispered back, "Yes, Daddy, fuck me hard!" He began to give my ass the pounding I had been so horny for earlier, precum leaking like a faucet from my erect dick. His breathing got heavier and his hands tightened on my hips as his cock slammed into me. It hurt because he was so big, but he'd done such a great job getting me warmed up and stretched out that it wasn't bad and was totally overridden by the pleasure.
With a few last really hard, deep thrusts that felt like he was trying to get to the back of my throat, he pulled back on my hips as he drove his cock as deep as possible and held it there, throbbing and pulsating as he shot his load deep inside me. It was incredible feeling his dick twitching in my asshole as he filled me with hot spunk. After he finished, he leaned lay down on top of me with his cock still inside me, and purred in my ear, "Thank you, honey, that was so good! Did you feel good too?" "Oh. My. God. That felt so good, Daddy!" We stayed like that for about a minute, both pretty tapped out from the intense fuck, his long dick still hot inside me. It felt so good just having it in there I was a little sad when he stood up and eased it out of me. "You stay like that, baby, I will go get something to clean up with " he slipped out of the room after quickly getting dressed. I lay there, my ass feeling warm from the friction but suddenly empty, hoping my gaped hole would close up soon. He came back in with some paper towels and handed them off. I used half to wipe myself and stuck the other half in my crack since I didn't need hot jizz leaking out, soaking through my shorts, and getting all over my leather seats. I slid my clothes back on and he quietly led me back down to the door, where he gave me a brief kiss and said, "Thank you, honey. That was wonderful. I would like to make love to you again soon!"
As I lay in bed at home, dildo back up my now very loose ass jerking off thinking about how I had definitely gotten the fucking I was looking for, I wondered when I would see him again. As it turns out, it wasn't long at all...
The end (for now)