Dennis Curiosity Pays Off Again

"Hey. I was wondering what you were doing Friday afternoon. I think I wanna stop by."

Dennis texted me three weeks after our first encounter. When he left the first time, I honestly didn't think he'd reach back despite saying he wanted me to fuck him.

"I think I'm ready to try that cock," he further messaged as he wanted to be "tampered with" again.

"Hey man, it was nice making you cum like you did," I told him as we ended up talking on the phone. "I never swallowed anyone like I did with you. Guess you brought the nasty out of me, too."

Since the last time, he couldn't stop thinking about everything that transpired: Me kissing him, the way I sucked his breasts, even the way I siphoned the sperm out of his cock while finger punching his prostate. Every antic touched him in such a way which allowed me to rent headspace in those three weeks, as he hadn't so much as touched himself in that time, waiting for the moment to get back to me.

"So you're ready for the dick is what you're saying," I asked him as I had a bulge in my pants.

"You really did something to me, Travis, to where I don't even look at my wife the same," he told me.

I looked at the phone in disbelief as this man really admitted I "changed him." In my mind I patted myself on the back for this, taking credit for turning this man into a cock hound when the reality was that he had it in him all the time. I didn't put a gun to his head to let me play the first time as he chose to express himself in my nest, "finally spreading his wings" to where he completely confirmed his bottom tendencies.

"I can't remember the last time I caught an orgasm, or came like that," he noted as he took to getting penetrated quite well, stating how he released cum at this moment more than any other.

He was hooked.

"So are you free Friday, or am I breaking out the toys in the office," he asked me.

I was getting hard on this Monday evening looking over my calendar, trying to ensure I had no plans as Dennis made it vehemently clear he was ready for his maiden voyage.

"You just have to promise me you'll take it easy on me," he said.

"Dennis, I can't make any guarantees," I told him as he had a round, juicy plum that didn't take much to tap.

I for sure wasn't out to hurt him, but coach him in his submissive training by discussing the "initial reception," and "acceptance" of a probing from another man's penis, no matter how big.

"You're not built like a woman, and yet that's no excuse as you will open your legs and accept me the same, you understand," I asked. "There will be no pulling away or me pulling out. You take that cock no matter how it feels, show me you're worthy of being my bottom bitch!"

He got quiet as I gave the pep talk until he began moaning and whining, going up a decibel as he was sitting in his pickup truck with his pants down, jerking out a massive nut.

"Holy smokes, I've got cum all on my windshield," he said with laughter as I was turning him on directing him.

"You make sure you clean up that mess and have that ass to me Friday afternoon," I told him before we hung up.

Friday came and when I woke up, I sent him a video of me stroking myself.

"I've cum twice a day since Monday," he told me, as he seemed a bit hot and bothered thinking of the pending evening.

The day sped by as 5:30 p.m. came, and he was calling my phone.

"Rain's falling pretty hard," he said. "You sure you still wanna do this?"

He was catching "cold feet" as the death of his anal virginity was approaching: the downpour did nothing but fuel me in assisting in creating the seismic shift of him once this cock touched his anus.

"You backing out on me," I asked.

"Not backing out, just figured the rain wouldn't help things," he said.

"Rain increases the mood for me. Makes me want to strip and do whatever comes to mind behind closed doors. Make sure you bring a bottle of bourbon over," I told him as I was preparing to light candles.

I wasn't making our get together a love scene, but rather trying to ease his concerns about getting fucked through a little aroma therapy, setting the mood to a calm, before the actual storm. having his anus stretched for the first time. The liquor would help as it would calm him, and ultimately appease me for I was in the mood for a good drink. An hour passed after we got off the phone when he finally rang my doorbell, the rain coming down profusely as it hammered the top of the house. I opened the door and let him inside, grabbing his umbrella, and the bourbon from him before closing the door, while he took off his drenched jacket.

"Welcome," I said to him before he handed me the jacket and we kissed, with me hanging his jacket then grabbing him by the hand to lead him to the couch.

"You're shaking like a stripper right now," I told him as I noticed he wasn't fully comfortable despite the smile.

It was as if the previous encounter didn't happen.

"What are we really doing," he asked, as he was literally fidgeting with his words, and not making eye contact.

"We don't have to do this," I told him.

As sick as it was, I was feeding off his demeanor as if I was a wolf that smelled blood. I wouldn't force anything, but it was a thing where an experienced guy like me could have such a novice within his claws. I got up to pour our drinks, then returned, placing the glasses side by side, as well as the Blanton's in the vicinity.

"Relax, take a sip," I told him as I picked our glasses up, handing him his as he would take a nice gulp, then sigh.

"To answer your question: What we're doing is what any other two adults would do when they're into each other. This case happens to be two, highly compatible men as one is rather new to this, while the other isn't. I'm in the mood to train. Are you willing to be trained," I asked him.

"Yes, I'm willing," he said.

"You willing to have a big, black dick deep in your ass," I asked.

"I'm more than willing, and ready," he told me before taking another gulp.

"Are you willing to let me touch you any, and everywhere, like before," I asked, as I slid my hand in his dress shirt. "Because even if you aren't willing, I'm gonna touch you anyway. You understand?"

"Yes sir," he whispered as he closed his eyes and bit his bottom lip.

He put his drink down on the end table while I began unbuttoning his shirt, with him sliding his arms out of it, then raising his undershirt to allow me to begin sucking that left tit while squeezing the bottom area of his right tit with my left hand.

"Rule number one: always let me touch, or suck, whatever I choose first off," I said to him as he began to moan while I nursed on that nipple.

"Whatever you like sir," he whispered as I began to bite down lightly on that hairy lump of his, just trying to leave a territorial mark.

After nibbling, I turned to kissing and licking the nipple as I wanted to give my own mixture of pain and pleasure.

"Talk about a roller coaster," he said after a minute or so before I began massaging them both at the same time.

"Take them pants off," I told him, and he would undo them before pushing the pair down to his ankles and kicking them off completely.

"Commando Friday," I asked as he showed he had no underwear.

"Commando for I knew what was going to happen at the end of the day," he said to me.

I went back to nibbling on that left nipple as I loved how he gasped and swooned in reaction. He begged me to let go so he could suck me, but I couldn't get enough of his feminine sounds as he showed his bitch side.

"I'll let you suck this dick, but first let's climb in the shower," I told him.

We finished our drinks, then walked to the closest guest bathroom, with me turning on the shower and entering the stall first. I'd sit on the stool with a rag in hand, lathering it with some body wash when he arrived shortly after. I made him face me as his belly and cock were in front of my nose, and I would use my long arms to scrub his scalp, then his shoulders before working lower, and turning him around. I waved the rag under the water, then added a second dash of soap on the rag before I scrubbed his balls and cock, then had him bend over as I gave the area between his cheeks a special scrub. He'd moan once I brushed the rag against his hole, and I would wrap my right pointer finger with the fabric, and plug inside to find he was squeaky clean.

"I would never come to you unprepared," he said to me before I directed him to touch his toes, and I scooped falling water in my right hand to splash on his hole.

Everything was clear, and so I grabbed his outer ass cheeks to pull him to me, and commence tongue brushing his eager hole in the shower.

"Feel good," I asked as he grimaced and groaned, reacting to my slab brushing the outer edge.

He started poking it out, and I counteracted by kissing the pink mini volcano, then digging my tongue inside and letting it flicker. I placed my hands on his sweet ass to pull his cheeks apart and devour him more as he whimpered from me scraping his soft walls. He tried his best to escape and I strengthened my grip, getting carried away until he almost fell over.

"I want that cockkkkkk," he begged.

He'd wiggle away from me and turn off the water, then step out of the stall to dry off with me behind him. We wiped each other dry before he headed back into the living room to sit on the couch. I stood in front of him with a fully erected prick and he would open his mouth to stick his tongue out and lick the slit, then closed his lips under the head to begin the suck session.

"Breathe through your nose," I told him as he closed his eyes and to glide his skull on my shaft.l

I loved the sight of him pumping his throat on my cock, leaving his drool on the shaft as he banged his face in my body. He squeezed tight and had me ready to blow early, so I pulled away, as he smiled while continuing to try and blow me.

"Reckoning time, boy, " I said to him.

The smile disappeared into a look of disarray as he knew this was the moment we worked towards.

"Get on your back," I told him, and he would lay flat.

He started shaking more, and I would talk him into letting me try him, advising him that this was somewhat a rite of passage.

"Gotta man up, boy. Get through this and you'll be able to get through anything else," I told him.

I imposed myself through mind control, letting the physical follow as he rolled to his back and held his legs up by himself. I took a gander at his entire posture starting with his eyes as they were closed, to his nipples that were hardened through anticipation, then the rest of his hairy, chubby body as his feet were pointed upward, and his hole twitching. I stepped away to grab the lubricant from the bedroom, and shook a small amount to fall into my right palm before stroking my throbbing dick as I was more than eager to break him open. I came back to him and pushed his feet back as that allowed for his ass to arch upward, with his pretty, pink anus facing the sky.

"Gorgeous fucking hole," I told him as I rubbed the outer part of his rosebud with my hand.

He clenched his teeth.

"Take a deep breath, Dennis," I said while trying to encourage him to relax, telling him to push his hole out once I entered so he could absorb the initial pinch.

"I don't know about this," he cried out.

I threatened to stop, and he apologized, then begged for me to enter.

"I just wanna get it over with," he said to me.

I crouched over his hole, bending my knees at a 90 degree angle and grabbing my dick at the base, pointing my curved tool downward until my tip met the rosebud. He winced, but I didn't give him a chance to protest. He screamed as if he was in a horror film once his walls were broken into. I wasn't letting up as I loved the sound of him breathing heavily, and the feeling of his hand pressing at my chest as I dropped my entire manhood down his chute.

"That's right, take it baby. Take the dick," I whispered to him.

Once I landed fully, I leaned down to whisper in his right ear about "how much of a good bottom he was, and that he could take dick better than anyone else."

"You didn't warn me about how big you are," he whined.

I let it sit inside of him, my balls resting against his hole before I took my lips to tug his. We made out as I was trying to erase the pain of having his cherry broken, and so I wouldn't move for two to three minutes as his warm, tight hole needed to adjust.

"Proud of you, Dennis," I said before moving my hips, pulling out slightly, then pushing back in as I was trying to mold him.

I made good on the promise of going slow, still trying to get him used to me as his body was in shock. I felt his walls percolating on my shaft, and every other stroke his sphincter squeezing and gyrating on the tip as I made it that deep inside. He'd whimper and cringe, for one moment it felt great, and the next it was uncomfortable for him.

"Say it with me: real deal cock," I told him.

"Real deal cock, baby," he cried out as I kept dipping at his insides.

I would pull out after five minutes because he needed a break, the friction from his hole evident as he couldn't fully relax. I acted as if I was going to rest beside him, but instead ducked my head low between his ass cheeks and licked that swollen, surly hole. I giggled while playing down there, making him moan as he claimed my tongue was like an ice pack. I took two fingers and pressed them against his hole then tried to pry it apart. He cooed once I brushed the surface with my tongue, then allowed it to tango with that stretched rosebud, causing him to curse me and beg for more cock.

"Fuck me, Travis," he yelled.

I stopped licking and raised up to push his legs back for round two, this time guiding my dick with my hips to sliding back inside and thrust deep.

"Ohhhhhhhh my Godddddddddd," he wailed as my still stiff member was filling him out.

The nasty sounds of his mushy hole coupled with his loud groaning was a drug, and I was addicted as I continued oscillating.

"Better," I asked.

He nodded and continued lamenting to the rhythm I gave as now his crevice seemed fully adjusted to me. I looked down to see him biting his lip, eyes closed and hands held above his head as he gave all of himself. I increased the pace and began moving my hips side to side while driving inside of him, making that hole greasy.

"Yeahhhhh, that's more like it," I said to him.

His hole began making a snapping sound each time I'd pull out, and I'd see his flower puffed completely from the beating he took. Dennis officially graduated from contemplating if he could take cock to having a hole that was a gourmand for penetration, pulling me in and squeezing whatever object gave fill. I recalled me fingering him while sucking him the last time, and how moist he became as this moment was that times three, with Dennis so "juicy," he stained my couch. We learned that all it took was the right amount of pressure on that prostate, the right stroke to tap the gland to make things messy as his rosebud was in full bloom.

"Breed me baby," he said before he wrapped his legs around my waist, and I continued jostling my hips against his until I inserted every ounce of available jizz into the depths of that orifice.

My body was shaking and we French kissed as I gave it up, my dick planted deep in his contracting hole. I laid there until I finished, and when I stopped shaking I'd roll over, with the both of us laughing after the intense turn of events. We laid beside, facing each other, looking into each other's eyes as the night unfolded.

"Was it so bad," I asked him.

"That was wonderful," he said to me while running his hands through my chest hairs.

He chuckled and thanked me for the encounter.

"I honestly thought it would be worse," he said to me.

He thanked me for being patient, and appreciated the fact I took the time to find different things to get him off. He once again wanted to lay and cuddle, but I reminded him that he had a wife to tend to, and that I would always be available for another round.

"I wish you were our live-in cock," he joked as he rushed to get up and shower.

I laughed at the notion that he had a life most would dream of, but claimed to be missing that one thing that only I could provide. I became his regular for a few more times until he moved on to better cock. I wasn't worried for it seemed my stock was on the rise with hot men, but I was forever grateful for Dennis letting me be the one who popped his cherry.