Dark Side Of Town

It was a hot summer Thursday night, bored, TV had reruns, nothing to do, I decided to take a drive. I suddenly found myself at dusk on the dark side of town parked in front of a river park, where I thought I might take a walk. I locked up the car, and headed toward the river walkway, I had been here many times during the day, but the nighttime vibe defiantly changed. There were people gathered in groups, not your normal types, more seedy, the benches were all occupied. Now I’m a guy in my 50’s, and consider myself in decent shape, so I wasn’t scared, but could see where it wasn’t the safest place. I believe I saw drug deals going down, hookers hooking, and homeless begging.

 At one point I saw a very young guy strolling the walk, at that time I thought to myself, he shouldn’t be there. He seemed to be about mid teens, extremely short denim cut offs, and a muscle tight shirt, midriff showing, was very fair skinned, long but well groomed blonde hair, and fairly short maybe 5’5”? or so, twinky but a strong twinky. I first thought drugs? But the more I watched him it seemed like he was just people watching, anyway, he wasn’t my responsibility so I continued past him. He stared directly into my eyes as we made eye contact in passing, and he greeted me very friendly like, saying hello as we passed, unexpectedly, so I turned my head towards him and gave him a late hello after the fact. I unexpectedly found myself staring at his tight shapely butt as it shifted from right to left with its ever so sexy bounce, with exposed lower cheeks. Crap I thought, what am I doing, he’s probably only 15 or 16, damn, so I snapped my head back in front of me and continued on my way. I stopped at a food truck, got a soda as I headed back towards the car, low and behold my little blonde boy passed by me the other way. I stopped and sat on a vacant bench, legs crossed, enjoying the evening river air, finishing my drink, when little blonde boy sat next to me. Damn, this is such a coincidence. He spoke again asking “you from around here”? His voice was much lower than I expected, as I turned to him and said “actually uptown”, as I noticed some facial stubble, maybe I was off a bit on his age, could be slightly older. Sitting he seemed much older, maybe it was his light complexion and short height that possibly threw my initial estimate off.

He sat with his legs crossed spread crotched, as he turned toward me, I turned toward him as he continued to chit chat with me, I was intrigued so I listened and gave vague answers. At one point, I blatantly came out and asked him how old he was, he replied quickly “ I get that a lot,……. but I’m 20”. Then he put his right foot on the bench, knee bent, and spread his left apart on the ground, this easily exposed a perfect sight line at a partial ball sack protruding out of his right leg, any further and they’ll be a ball on the wood bench. All I could do is stare, no matter how hard I tried to look away, my eyes kept slipping back to his crotch. He looked at my eyes as he parted his hair with one hand and flipping his head to one side, saying “you like”? Flabbergasted at his attitude and boldness, I replied, “let’s not say like, just yet, but you seem interesting”. He asked what he needed to do to convince me. I thought for a while and replied, I like to check my goods out thoroughly before making that decision. He immediately replied, “here, your place or mine”? Again not expecting that reply, I said “I don’t ever pay, especially for overpriced product and ego enthused little brats”. But… he then offered, “ hey I’ll give you this on the house,…… if you dislike nothing lost,…. if you like…. we can call it a tip,….. and you decide the over or underprice rate”???? “Deal”? As he slid closer and took my hand off the back of the bench, and dropped it in his lap, brushing across his thigh and his partially exposed nut sack. I thought to myself, shit is this really happening? This young kid? He feels nice, smooth, and he seems clean and cute. Then the negative side, is he possibly under 18? Is this a sting operation? I can’t do this here, I can’t do this at his place either it could be a set up. Hell even if he’s 18 he’s still younger than my own kids, but then again he came onto me, he’s got my egos attention, this young kid knew what to say to get it. So I came out and said why, and are you really over 18, he laughed and pulled out his license, it says he was 20, I still didn’t believe it, but if it was a sting, I could claim I tried every which way to be sure he was over 18, hell that had to count as part of my defense doesn’t it. Now I’m thinking with my dick. I said, “Ok fuck it, let’s do this, my place, my cars up the street”. He said, “let’s do this”, and we both stood up, I tossed my cup in the trash, and he followed.

We arrived at my condo, he checked out the place, plopped onto the couch, I asked him if he wanted a drink, he took a beer, as did I. I sat next to him, I asked how does this usually work? He said “ahhhh a newbie, let me show you”. He took my hand put it on his thigh, and worked my fingers under the material. I could feel warmth, soft skin, fine hair, as I swirled it between my fingers, I inched up further and felt his velvety sack, as he pulled my head with his hand into his and gave me a wet lip kiss. I haven’t been kissed in several years, and my pants we’re tightening. He looked into my eyes with his blue eyes, as he began to lean in for a second kiss, this time his blonde hair flopped into my eyes as he darted his tongue separating my lips then pulling my lower lip out with his teeth, slowly releasing it, as he gripped my crotch firmer.

I felt a warmth shoot through my body as I was ready to resign myself to him. I have been alone and on a dry spell for the last 10 years at least, and today and now I feel 16 again, feel wanted, and yet mad at myself for why I haven’t pursued a partner in years, I hadn’t been here for even 10 minutes yet and I’m already in heaven.

He stood and pulled off his crop top shirt, exposing a bare chested, firm body, and inviting abs, with a perfectly placed and shaped navel, cute but slightly large pink protruding nipples, if he had any fat it was in his nipple area, yet his height and weight and maybe 28” waist made him very much a twink. I raised my hand and rubbed my palm down his chest from his neck to his navel, feeling every crevasse and every inch of skin, before long I was massaging his chest, sides and back with both of my hands. Somehow I wound up sitting on his lap massaging his upper torso, staring into his blue eyes, as he leaned in for a 3rd kiss, this time his tongue parted my lips and his tongue tangled with mine. My dick was rock hard inside my jeans, but yet as he drew me in for the kiss, I knew he could feel it poking his stomach.

Next he removed my shirt, getting it stuck on my head and bouncing my glasses to the floor. He grabbed me by my sides as he slid me back and forth on his lap, I could feel his hardness through my jeans, itching to get out, he then pulled me close so our chests were touching, the warmth generating between us as he bent in for a 4th kiss, again tongue dancing as saliva dripped from the sides of my mouth, and he was quick to suck the escaping spit from my face.

He pushed me gently off his lap down to the couch, where he began to unbuckle my belt, and he removed my jeans, leaving me in my skivvies, my dick head and hardness protruding out of the waistband. Him in his cut offs, ass cheeks poking out, he crawled up to my face, gave me a peck kiss first, as he then began to tongue bathe me starting at my neck, he stopped at my nipples and spent way too much time on them, softly biting and stretching them, the wetness he left behind, made me shiver with goose bumps, yet my dick was now in pain burning, if I touched it it probably would shoot cum streams through his body. He gradually moved to my navel, it was here my dick began trying to raise and lower by itself stretching the elastic that was constricting it holding it firm against my body. He grabbed my balls through the cotton as his tongue brushed the exposed head of my dick, as his eyes made contact with mine, and I lay there in a transient state of ecstasy. He pulled my underwear off before returning his tongue to my inner thighs, my now freed shaft was bouncing by itself wanting to burst out of itself, it was painfully hard.

Finally as his hands and soft touch replaced his tongue on my thighs, and he engulfed his mouth on my desperate manhood, he began to jerk up and down while twisting his tongue on the most sensitive parts. I now realized I was moaning in pleasure, louder than I could imagine, and I came so freaking hard as my dick seemingly doubled in size with each explosion inside of his mouth, my breathing was deeper than ever before, as I screamed. He came off of my dick looking up at me smiling, as he caught one drip with his tongue off of his lip, and then licked his lips, in satisfaction. He swallowed it all.

 I was exhausted, totally wiped, as my limp arms and legs dangled from the couch, and my dick starting to subside but still pointing upward, and I realized I was covered in sweat. He stood again, unbuckled his tiny tight cutoffs, as he dropped them to the floor commando, and exposed a beautiful smooth, slightly pale white pinkish but large dick and balls with a large purple head, against the rest of his beautifully tanned body. He lowered down to my still spent body, as his dick touched mine as he lay on top of me and began grinding against me, suddenly my manhood began to grow hard again, as the two members generated friction and heat, I then took in the entire experience and realized his balls were rubbing mine, as he went in for another deep kiss.

He stood again bringing his luscious dick to my face where he straddled my head, his knees on the arm, lowering his dick to my lips. I saw the huge round purple knob with a slightly leaking slit in top get larger as he came closer to my mouth, I instinctively opened wide as it entered and I closed my lips around it, he began pushing in and out, as I watched the lower shaft wrinkle and flatten as I could see blue veining sliding in and out, he lowered deeper and deeper until I began to gag, he let up and worked it slow till I could get used to it. Somehow he eventually got it all in, as I realized his nut sack was bottoming into my nose, his clean scent made me want him to stay there. I was also able to see directly up his sweet ass crack as it got closer with each pump. A fine pink bud slightly protruding as his nut sack covered my nose.

While I was enjoying my view and the unique feel and flavor of his body inside my mouth, again I didn’t realize he was sucking my meat and balls again while fingering my ass crack, damn he had me hard again, and that thing he was doing with my balls was absolutely wow. Next while my jaw was tiring and my mouth was drying out, he leaned over further and began sliding his tongue in my ass crevasse. I have never had this sensation before, eventually he began encircling my bud hole. Was he going there? Yup you bet, he pushed in, god what a feeling, at the same time I was ready to cum again, he began to leak as the salty flavor became stronger and stronger in my mouth, I pushed him out as he sprayed all over my chin and chest, and at the same time my cum began shooting toward his landing on my chest. We collapsed onto one another cementing our cum together. By now I have had more than enough, but was he done?

He got off me, pulled me off the couch, as he rested his knees on the cushion and his arms on the arm of the couch, and then instructed me to Fuck his ass, I climbed on the cushion behind him as he lowered his ass to the proper height of me, my softening dick perked up at the sight of that soft perky twinky teenage ass, I took my hands and spread those cheeks, and stared at that one eyed hole as I tried to push my thumbs in to spread it open, it seems he allowed me to do it as I heard him moan in pain or was it pleasure? He asked me to eat him out, I tried but couldn’t, so we compromised and I offered spit to which he agreed. I eventually Lined my dick head up to him and per his instructions proceeded in slow but steady till the head was in, where I waited for a minute before continuing. It felt wonderful as he began pushing back against me, before I knew it we were bumping uglys, my balls into his ass cheeks, I wrapped my arms around his chest squeezing him tightly as my dick slid in and out. Our naked bodies banging together, before long I called out to him that I was Cumming and tried to pull out but he insisted I push in deeper as I dropped my load deep into his bowels.

We both collapsed, and fell asleep, he stayed the night, I awoke with him facing me staring at me as if he conquered mount Everest or something, I guess I was as much of a challenge for him to as it was to convince me he was worth it. We got up, I flipped on the coffee maker and jumped in the shower, he joined me and we continued where we left off last night, he teased me and we wound up back in bed again and did it all over, then finally back to the shower and got dressed, we sat and drank over heated burnt coffee, as I offered to take him home, he slipped me a card with his phone number on it, and asked “Well? Was I worth it?” I replied “Every Cent” and I pulled $200 cash out of my wallet and gave it to him, saying “that’s all the cash I have I catch you up on the next time”, he replied so there will be a next time? I’m glad, but remember I said it was on the house?  I said “NO way, that was way too good to let go unrewarded, and I’ll…… excuse me,…….You’ll be back”, we walked to the car and I drove him  to his apartment, incidentally a very luxurious section of town.