Kyle - Good-Touch Bad-Touch

I think the good-touch bad-touch conversation was lost on me. I was already in the early stages of puberty when I got the talk and my hormonal brain didn't see a problem with a hot stranger touching me in my private areas. Hell, I enjoyed touching myself there, if anyone wanted to do that to me...I was in.

That launched a regular fantasy for me that carried me into high school. I didn't have easy access to porn in 1992, so using my imagination needed to do the job. Thankfully, every attractive woman I saw on the street became cannon fodder for those jerk sessions. I must have beat off most nights to the idea of a hot older woman (in her early 20s) putting her hands into my pants and jerking me off.

I didn't realize how naive that thought process was until I was 16 and on a class overnight trip to visit Washington, DC.

We were paired in hotel rooms, 4 boys with 2 queen beds. There was a chaperone for every ten to twelve students, but we knew they would be passed out by 9 pm, and frankly, we didn't care about getting caught doing stupid shit because we were having fun.

With enough caffeine and sugar running through our bodies, you would've thought we were all drunk from the way we were acting. By 1 am Truth or Dare had devolved into a dare or double-dare game. I was stripped down to my tighty-whities, my best friend Sam was completely nude, covering his junk with a pillow. The two Christopher's had only boxers on and I was dared to walk down the hall only wearing my underwear and get more soda from the machine as if it was a completely normal thing to do.

I'm no quitter, and I know the double-dare will be way worse if I don't do it.

"You guys are so lame," I shook my head and confidently walked toward the door. I'm not embarrassed at all, I'm 5'11" with an athletic build, and genetics are really doing me justice in my Jockey's. My hair is a light brown with a part down the middle, girls love to run their fingers through it. My eyes are dark brown and set deep, I don't have the high cheekbones but I have a strong jaw with perfectly straight teeth.

I strut over to the door with the confidence of someone who didn’t have a clue what he was about to get himself into. I grabbed some quarters from the pocket of my jacket, hanging on the hook just inside the entryway, then peered through the peephole on the door to make sure the coast was clear. With a flash of my pearly white teeth to the guys, who were hooting and making all kinds of snickering remarks, I casually unlocked the door and stepped out, looking both ways then strolled down the hall. Looking back I saw their heads pop out of the door, watching me walk down a hall reminiscent of The Shining, then around the corner where I had another 10 yards before the vestibule where the soda and snack machines were kept hidden.

I heard a door open at the other end of the hallway, so I quickly dove into the snack room. I was confident and comfortable with my body, but I wouldn’t want one of the chaperone-parents to catch me in my underwear.

As fast as possible I put my change into the machine, it kicked my quarters back out into the change return. I did it again and again the quarters ended up clanking into the return slot. Fuck, if I return without a can of soda the guys will claim I didn’t complete the dare. Out of the corner of my eye, I saw a man walk passed the doorway, I froze. I don’t think he saw me or maybe didn’t realize I was standing here in my underpants. I looked at the map directory on the wall, it looks like every floor has the same soda and candy machine set up in the same spot, if I quickly take the stairs up a floor I can try that soda machine.

Peeking my head out the doorway to see that no one was in the hall, I ran to the far end of the hall where the stairs were, pushed through the loud heavy door, and darted up the stairs. The little window in the door let me know the coast was clear so I quickly ran to where the machines were. My heart was racing from the running and the excitement of being so on display. I put my quarters in the slot and they fell right into the change return tray. I rolled my eyes, I can’t believe this.

I turned to walk back and a guy walked passed, ignoring me at first but then doubled back to look at me. His balance was off, his tailored suit a bit disheveled, his French cuffs undone, his necktie was undone and the first few buttons at the top were unbuttoned. He looked me up and down then smiled, leaning against the door frame.

“I feel overdressed,” he laughed at his joke.

I smiled, looking down at my underwear then back up to meet his gaze, “Yeah, I was just grabbing a soda, I didn’t expect anyone to be up at this time of night,” I laughed.

His eyebrows raised, “Where do you keep your money?” Then he looked directly at my crotch, which gave me a weird but exciting feeling I didn’t recognize.

I held out my hand, showing him my quarters.

He smirked, “oh,” he looked down the hall both ways then leaned back on the door frame to steady himself, “That makes sense, not much room left in those undies,” his grin got wider.

I felt a sense of pride in my body, which was odd because never had a guy complimented my body before. I also felt the blood start to rush to my dick and my face at the same time, my chest turning red along with my cheeks as my brain tried to will my dick not to get hard from this interaction.

“You like to show off?” he asked, somewhat slurring the word “show” as he said it.

“Huh?” I tilt my head, not quite understand his meaning.

He stepped forward, closing the gap between us, his hand immediately cupping my package gently. I froze, my brain flatlined. I tried to swallow, or breathe, all my blood flowing to my dick, but I couldn’t comprehend what was happening.

“Wow, these are full,” he said, continuing to grope the pouch of my briefs, the smell of alcohol on his breath.

I felt my dick get instantly rock hard, my heart beating so hard there was a slight ringing in my ears. I just stood there, waiting for…I don’t know what, but I was in some sort of default, low brain capacity mode, basic functions only and my body was focused on enjoying being touched by someone who wasn’t me in this moment. To my surprise, enjoying being touched by a man who was at least 30 years old and probably drunk.

“What’s your name?” He asked in a whisper, still massaging my package, squeezing my balls through the white cotton material.

“Umm…” I squeaked out, then cleared my throat, “Kyle.”

“I have soda back in my room Kyle, if you want to come with me,” he said.

I just nodded and like a zombie I shuffled down the hall, only a few doors from the snack machine room, where my new friend had his door propped open with the latch lock, pushing it open and then letting us both in.

He guided me over to his bed, then quickly dropped to his knees, my stomach jumped into my throat, was he about to do what I thought he was about to do? He hooked his fingers in the waistband of my briefs, yanking them down to my ankles as my hard dick flew out nearly smacking him in the face. My proud, thick 6.5” cut cock was never this hard before, the visible veins were straining and pushing my dick to be harder than ever.

He doesn't even hesitate, his tongue slides up my shaft from the base to the tip and I nearly cum right away. I let out a groan and he huffs out some air with a smile as he continues to wet my dick with his tongue. He pushed on my abs, forcing me to sit on the bed, spreading my knees wide for him to have full access to my cock and balls.

He jerks my dick and his mouth goes straight for my balls. Holy fuck, I gasp at this amazing sensation I didn't know existed.

I leaned back on my hands, closing my eyes and enjoying this insane experience until he takes my dick into his mouth and starts to bob up and down.

My eyes shot open, "mmmm," I groaned, falling onto my elbows now. I've never experienced anything sexual other than jerking off with Sam once, but this... this is amazing. His free hand comes up and strokes my abs and it adds so much to an already amazing experience. I'm not going to last.

I fall back, laying flat on the bed. He brings one of his hands up to cup and squeeze my balls, his pinky finger slips and rubs my taint and I instantly feel my balls tightening. I know I'm going to cum and without warning I groan and my balls empty into his mouth. It was the best orgasm of my life, my balls almost ache from how much cum they dumped into his mouth. He gags, and to my horror swallows my cum.

I’m spent but I manage to prop myself up on my elbows as I catch my breath. Looking down at my tight body, just over my wet, softening dick I see his face. He’s staring back at me, squeezing my thigh with one hand, his face is a little contorted, his mouth is wet and there’s a bit of wetness at both corners of his mouth. His body is shaking a bit. Wait…is he jerking off?

I start to regret what has transpired here and I’m feeling very uncomfortable watching some strange guy kneeling between my legs jerking off as he looks at my nude body. I don’t know what to do. Should I just put my underwear back on and leave? I don’t want to watch him finish, the thought of watching him cum makes me cringe.

I sat up and went to lean down to pull up my briefs which were bunched up around my ankles, but when I leaned forward I saw a sight I had never seen before. He had his pants undone, his long pale, uncut dick pulled through the fly of his boxers, stroking it fast, like he was getting close to cumming. My eyes jumped up from his dick to meet his eyes.

“I want to cum on you,” he mumbled.

The words rang in my head, “You…what?”

“I want to cum on you,” he said again, with more emphasis on “you.”

I tried to pull my underwear up but his hand snatched them back down. I got a little more uncomfortable.

“I want to cum on your face,” he smiled, still stroking his dick, then getting off his knees his dick was eye level with me.

There was precum all over the head of his dick, I watched as each stroke pulled back the foreskin of his uncut dick, smearing his precum all over the thick head.

I shook my head, “no way.”

“Your ass then,” he kept fisting his cock, varying the speed, rotating his hand slightly with every stroke.

“Huh?” I scrunched my face up, my eyes going from his dick to his face and back.

“Turn over, lay on the bed, I’m going to cum on your ass,” he told me.

I felt bad, he had just swallowed my cum after giving me my first and most amazing blow job. I slowly lay back down on the bed, rolling over for him. He pulled my briefs off my ankles and tossed them on the bed, landing right next to my face. I heard him pull his pants the rest of the way off, his belt hitting the ground with a clunk. He quickly climbed on the bed, his hands sliding up my legs as he straddled me. The warmth of his nude lower body on mine was intense. He slid up my legs and landed on my ass. He grabbed both my cheeks and squeezed hard, letting out a groan.

I closed my eyes and just waited for it to be over, maybe it won’t be so bad letting him cum on me. The sounds and sensations burned into my brain. His weight on me had me pinned onto the mattress, it was somewhat comforting, his hairy balls were dangling on my ass, tickling the previously untouched skin. His meaty cock suddenly slid between my ass cheeks and he groaned with pleasure. He held my glutes together and started humping my ass, I’ll admit this felt weird but good.

I was coming around to like the idea that this guy was turned on by me. I felt him lay flat on my back, he was breathing heavily on my neck and it got weird again. Now he was humping me, his warm body completely covering mine felt awesome and his dick sliding along my ass crack was such a hot sensation. I felt myself getting hard again and I started grinding my dick into the bed as he grind his into me.

“Your ass feels good Kyle,” he whispered.

I didn’t know what to say and I just let out a soft moan.

He humped my ass a couple more times and then sat back up, stroking his dick. He shift his body back down my legs and then I felt the most amazing sensation in the world, he put his mouth on my ass hole and his warm wet tongue started to lick and poke at my hole.

“Mmm,” I couldn’t help but moan, holy shit did this feel good. I continued to grind my cock into the bed, spreading my legs a little so I could switch from grinding to full-on fucking the bed as he tongued at my hole.

After a few minutes he pulled his tongue from my hole, maneuvering his body between my now wide-spread legs and I felt the tip of his slick cock pressing directly on my hole where his tongue was. He grabbed my hips and started to pull me onto his cock.

“Ouch, that hurts,” I groaned as a sting shot around my tight outer ring.

“Shhh,” he hissed and pressed harder.

“Ungh, that hurts, ow,” I tried to wriggle out from under him, but he held on tight and pressed harder.

“Shhhh,” he hissed again, pressing harder still, and then I felt the most excruciating pain in the world when his dick popped into my virgin hole like I was stabbed in the ass with a fire-hot knife.

I tried to let out a scream but nothing came out, it knocked the wind out of me. My eyes clenched shut, I tried to breathe. All I could do was groan and try to pull away but the sting went deep inside me to places you can't rub like a stubbed toe or a bumped elbow. “Fuuuck,” I managed to squeak out in a gasp.

He just groaned and pushed deeper, not stopping until I felt his bushy pubes grinding against my ass with his dick deep in my hole. I can’t understand how his tongue could feel so good but his dick could feel so painful.

He lay on my back again, groaning in my ear, his stubble scratching the skin of my cheek, and he started to hump my ass. Every stroke stretched my virgin hole a little more and it felt slightly less painful every time he bottomed out inside me. I clenched my teeth and held my breath as I tried to take it like a man.

“Fuck, man, you gotta pull out,” I groaned.

He kept thrusting, harder and faster, “Just a little more, I’m so close,” he breathed in my ear.

“Ugh, hurry up, it hurts,” I clenched.

He humped harder, holding my shoulders as he pushed every inch deeper into my hole.

“Fuck,” I groaned.

He grinds his dick deeper into me. It still hurt but it was starting to feel good at the same time.

“Kyle I’m about to cum,” he whispered, his breath and thrusts getting shorter.

“Hurry up,” I groaned.

He thrust a few more times and then pulled hard on my shoulders, his cock swelling inside me, he kept thrusting and pushing deep and I felt it twitch as he groaned and pulled himself hard into me, then warmth, a very wet warmth flooded inside me. He thrust a few more times and it was so smooth and it felt so good, that we both moaned. “Oh yeah,” he groaned, grinding his hips into me. Then he pulled out quickly and rolled onto his back on the bed, out of breath.

“Are you done?” I asked, opening my eyes for the first time since he pushed the head in.

He breathed heavily, “yeah.”

“You’re not going to cum?” I asked, looking over at him, his face wet with sweat.

He smiled, running his hands through his hair, “I did cum.” He closed his eyes, still catching his breath.

I jumped up, “wait, did you cum inside me?” I reached my hand back there, feeling my ass hole, it was slick and slimy, I pulled my hand to my nose and smelled the wetness. It smelled like cum.

He chuckled, “of course.”

“What? Why would you cum inside me?” I got furious and ran to the bathroom.

“I thought it was ok, it’s not like you are going to get pregnant,” he chuckled.

I grabbed some toilet paper, wadded it up and wiped my ass the best I could, and then flushed it. I saw myself in the mirror, flushed from the neck up, my hair a mess, my naked body shiny from a day of sweating and this experience. My dick is still somewhat chubbed. This is a guy who is no longer a virgin, I stared at myself.

I heard him start to snore from the other room.

I quickly walked back into the room and found my briefs under his arm, yanking them out without caring if he woke up. I pulled them on, tucking my dick back in and adjusting myself to look like I didn’t just lose my virginity to this…guy. I looked at him, naked from the waist down, his deflated cock looked much smaller than it felt when it was pumping in my ass a few minutes ago. I shook my head and then headed for the door.

I peeked through the peephole and saw nobody in the hall. Just as I opened the door, I stopped, turned, and ran to his mini fridge, which was filled with soda and alcoholic beverages. I grabbed a soda and ran down the hall, down a flight of stairs, and back to my hotel room. I walked in and everyone looked up at me.

“Kyle, what the fuck took so long,” Sam looked up at me from one of the beds, now wearing his Fruit of the Loom white briefs, watching TV.

The two Christophers were in the other bed under the covers, staring at me.

“You guys wouldn’t believe how many soda machines I had to try before one took my quarters,” I smiled.

They laughed and I got in the bed with Sam, cracking open the soda and taking a sip. I got under the covers and we all watched late-night HBO, which was just softcore porn. I had already emptied my balls tonight, so it didn’t do much for me and I passed out before everyone else.

The next morning I woke up to Sam cuddling me, clearly, he had morning wood and it was pressed against my ass through our underwear. I know he was still asleep, but the idea of Sam doing to me what that drunk guy did last night got my dick hard. So I did the only thing I could, I got up and took a shower, jerking off to a new fantasy for the first time in years.