Over the Edge Ch. 01

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Bi-curious guy's first encounter.
2k words
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Part 1 of the 2 part series

Updated 06/10/2023
Created 05/29/2021
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Like some straight guys, I've always been curious about sex with another man.

After years of reading and watching gay porn online, and amusing myself with toys, the simulations simply weren't stimulating any more. I decided to take the next step and have a real encounter.

I posted a profile to a gay dating site: "59 years old and looking to explore my bi-side with NSA meet-ups. I'm 5' 6" and about 170 lbs. Seeking someone around my age who'll show me the ropes. Must be DDF and cut. Available most of the time. Can host or travel."

I received a number of replies, mostly from other curious guys or younger ones, which didn't really interest me. I wanted someone with experience.

About a week later, I received a message that piqued my interest: "Hi there, I can help you explore your bi side. We can take it slowly. Have you ever been edged? Great way to start! I can host."

His profile said he was 63, 6' 0" and 195 lbs. His pic showed a rugged looking, clean shaven, man with a full head of gray hair and a friendly smile.

I responded: "Thanks for reaching out. I'm definitely interested. I have absolutely no experience, so taking it slow is how I want to go."

We agreed to meet at his place Friday evening at 7 p.m. He lived in a condo about a 20-minute drive from my place.

Friday arrived. I had butterflies in my stomach, both in anticipation of what I was about to do and some trepidation - after all, this guy was a complete stranger. I showered and headed out, determined not to chicken out.

The condo was a newly built low-rise, just four floors. I punched in the buzzer code he gave me, heard the door click, and walked in. His corner unit was on the ground floor, down a corridor to the right. I got to the door and was just about to knock, when it opened.

"Hi, I'm Max, come in," he said with a welcoming smile, gesturing me in.

He was barefoot and wearing a black nylon track suit. He was lean and I could tell he kept in shape.

"I'm Paul, nice to meet you," I replied and entered, slipping off my flip flops.

As we walked into the living room, Max said, "Look, I realize you're probably nervous, so let's take it easy. Have a seat on the couch and I'll pour us each a glass of wine. There's no pressure on you to do anything. Just enjoy yourself. If you decide you'd rather do nothing, well at least you'll have had a glass of nice Pinot Noir and some conversation."

He went into the kitchen, and I looked around. The place was open concept. The living room area had a couch and two easy chairs, all leather, facing a gas fireplace. On one side of the fireplace was a bookshelf, on the other an entertainment centre with a TV and stereo system. In front of the couch was a rustic, faded red chest serving as a coffee table.

I sat down on the couch and he returned, handed me a glass and sat down beside me.

"Cheers," he said, as we clinked glasses. "Tell me about yourself."

I told him I had been married for 27 years, but split up about eight years ago. I hadn't done much dating, and I was now semi-retired, doing a bit of project management consulting work to keep busy.

Max told me he had retired at 55 after selling a successful property development company, so he and his partner, Aaron, could travel the world. Unfortunately, his partner died a few years later.

"I prefer to remain single and play the field," he said, with a chuckle as he patted my thigh.

I felt completely at ease. We made small talk for a while, mostly about sports and current events, while sipping our wine. When Max finished his, he placed his glass on the chest in front of us, and said, "Ready?"

I put my glass down beside his. We got up and he led me down a hall, past a den and bathroom, to his bedroom. It had king-sized bed with black bedding, with night tables on each side. The curtains were closed and the only light was a lamp on top of a bureau, making the room somewhat dim.

"Let's get these off you, shall we," Max said as he lifted my t-shirt above my now outstretched arms.

He undid my shorts and pulled them down, along with my underwear. I stepped out of them, now naked in front of Max.

"Hop up on the bed and lay on your back in the middle, with your legs spread," he said. I moved toward the bed and climbed on, my excitement growing. "Now, to get the full effect of edging, I am going to put a sleep mask on you. It helps heighten the sensation."

Max put the mask on. I felt him get on the bed. He placed both hands on my thighs and slowly moved them up and down. I started to get hard. He kept rubbing my thighs, and then stopped. I heard a squirting sound, and felt him move closer.

He grabbed my now hard cock and began slowly stroking it with one oily hand, and massaging my balls with the other. Every so often he would rub his palm atop my cock, sending jolts of pleasure through my body. He would quicken the stroking, and then dial it back to a slower pace.

My body was soon moving to the rhythm he set. Just as I felt I was near coming, he would stop and massage my balls, before stroking me again. I was now moaning with pleasure. It felt absolutely amazing, like nothing I had ever experienced.

I heard another squirting sound, and felt warm oil flow down my cock, dripping onto my balls. He again worked his hand all over my cock. The closer I would get to coming, I would start thrusting, and he would know to stop, preventing me from shooting my load. Sometimes he'd stick a finger in my ass, which just about put me over the edge. Other times, he would twist a nipple, giving me pain and pleasure simultaneously.

"You know, there's something else that would heighten the experience even more," he said, quietly. "Would you allow me to tie your arms and legs loosely to the bed?"

Whoa, I thought. Not sure being naked and tied to a complete stranger's bed was a good idea. But this felt so good, and Max was so gentle.

"Okay," I said, somewhat tentatively. "I'm game, I guess."

"You won't regret it," he said. "In fact, I guarantee you'll love it."

He got off the bed, gently grasped my left arm, tied a cloth band around the wrist and secured it to the bed, before moving onto my other limbs. I was now spread out like a starfish. He climbed back on and resumed his stroking. Faster, slower. Massaging my balls. Fingering my ass. Twisting a nipple. Repeat. Repeat. My cock had never felt harder, and my moans were getting louder. And he was right, being tied to the bed had heightened the sensation.

I needed to come soon, though. I couldn't take this much longer.

"You'd like to come, now, wouldn't you?" Max asked.

"Oh, yes, please, let me come," I pleaded.

"Your release is literally in my hands," he said, with a laugh. "I wonder. Will you do something for me?"

He took off my mask. He was now naked, and as I had assumed, he was well built. He had a patch of hair on his chest, the color of his hair. And his cock, thin but long, was hard and pointed at me.

Without a word he climbed towards me until his legs straddled my chest. He leaned forward, holding himself with his hands on the headboard. His cock dangled above me, inches from my face.

"You're in a somewhat uncompromising position, Paul," he said. "Naked, tied to my bed, at my mercy and desperate to come."

He was right. He had played me. But I didn't care. I wanted this.

I opened my mouth, and he slowly moved downward, his cock entering my mouth. I wasn't sure what to expect. It felt warm and almost rubbery. He slid it along my tongue, in and out, only inserting a couple of inches in my mouth. I made sure my teeth didn't scrape his cock.

I was loving it, as he slowly moved his cock in a little further. I swirled my tongue around his shaft and along his piss hole, tasting his pre-cum.

"You're a natural, this can't be your first time," he said, and then he thrust a little deeper and I started gagging, my eyes watering.

"Ah, maybe it is your first time," he said, and pulled back.

He continued fucking my mouth gently, slowly going deeper. I was living a fantasy, being fed a cock while tied down. I savored his pre-cum. He continued feeding me his cock for a few minutes. He had managed to get most of it in my mouth without me gagging. Then, suddenly he pulled out and climbed off the bed. I moaned in disappointment. I had wanted to taste his seed.

He grabbed a wedge-shaped pillow from the floor, and crawled back onto the bed between my legs. He lifted my thighs and ass, and using his right knee, pushed the pillow under me. Now, I was naked, bound and my ass was exposed.

He grabbed a bottle of lube and coated his cock, before pouring some on my ass and rubbing it in and around my hole, all the while looking me straight in the eyes with a bit of a smirk on his face. I was about to get fucked for the first time.

When the evening began, I was hoping for no strings attached, long hand job. Yet, having his cock in my mouth felt natural, and the fact that he was about to fuck me filled me with excitement. I'd only ever had dildos up there. I wanted him and he knew it.

Max positioned himself above me, and slowly entered my ass. There was no pain, only an intense feeling of pleasure as his long cock slipped in and rubbed my prostate. He leaned forward, his arms by my side and started fucking me. At first, he was gentle, then he started thrusting harder.

"Fuck, you're tight," he said.

I was moaning as Max continued to fuck me, his thighs slapping my ass with every thrust. The feeling was intense and amazing. He fucked me like this for some time, then slowed it down for a while, before moving back to harder thrusts. The bed was creaking as he kept fucking me, his eyes now closed.

His breathing had quickened now and I knew he was close. I considered asking him to pull out, but just as quickly as that thought came, it was too late.

"I'm gonna come," he grunted.

And then I felt his cock unloading in my ass with his final thrusts, warm cum filling my hole. He collapsed on top of me, breathing heavily. He lay there for a few minutes, before he slowly pulled out.

My cock was still rock hard and I was still bound. Max started stroking my cock, slowly at first, then speeding up. Teasing me, teasing me. He kept stroking, and massaging my balls.

I could feel his cum slowly leaking out of my ass. He noticed it, too, and scooped some onto his index finger.

"Open up," he said.

I opened my mouth and sucked his cum off his finger.

He kept stroking me, teasing me, until finally, cum exploded out of my cock, spraying my chest and face. My entire body was shuddering. It was the most intense orgasm I had ever had, no doubt fuelled in part by his edging and fucking me.

"Now you've finally experienced what you've always just fantasized about," he said, with a smile. "And I'll wager it was even better than you'd hoped for. The good news is, the night is young."

With that, he put the sleep mask back on me, got off the bed and left the room.

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AnonymousAnonymousover 1 year ago

I had a first encounter just before the pandemic with a guy that I met through a profile I placed on gay encounters site looking to try first time oral with a safe guy. I took a Chance and was so looking forward to exploring further with this guy in his 40's who had a beautiful rock hard average size uncut cock that leaked so much precum! I'll never forget when he asked me to taste it, I was hooked. He was in a transition where he had broken up with a long term partner and was exploring and he said I should be careful on the site because there were a lot of flakes. I really appreciated his approach and thought this was a guy I wanted to explore with. He was very relaxing and and the first time I met him, he invited me to just relax, poured me a water and we sat on the couch and he told me when I was ready I could just start rubbing his crotch and start exploring. My heart was beating so fast, I was nervous about this but also in my mind I was thinking, I can't believe I'm going to actually finally do this. I spent a lot of time licking his shaved balls and he then suggested we head up to his bedroom. I loved the feel of his hard yet soft dick as I sucked on him. In hindsight, I wish I had swallowed his load both times we ended up meeting in his home. He actually rimmed me a bit which was a wonderful feeling. I think he was interested in actually fucking me and he felt me out about my feeling about ass play, but he didn't push it and by rimming me, it did get me thinking a bit about the pleasure and perhaps exploring that further. I think this is why he agreed to a second meeting. In our second meet , he did the same thing, rimming me and he spent a fair amount of time holding my legs up and rubbing his cock along my ass crack and when he was ready he to cum he asked if it was ok to cum on my chest...I told him it was and when he was jerking his dick load onto my chest, I also let my own load go onto my stomach, enhanced from the smell of D's cum. It was a very good experience and I was looking forward to picking up our exploration again after the pandemic. When I told him I liked the idea of a bit of man scent he later sent me a pick of his sweaty crotch in a pair of bikini underwear after he had worked in his garage on a hot summer day. That pic caused me to spill a load thinking about getting my face into his crotch again after a workout like that, his underwear was wet around the edge...mmm. The unfortunate thing was that even though we were in touch on and off through the pandemic, this fella disappeared from the website just as things were opening up again. Too bad...I hope it was because he found himself another long term partner...if so...wouldn't it be neat to explore these feelings with two guys!

AnonymousAnonymousalmost 2 years ago

I'm bicurious. Haven't done anything but an encounter like this would be hot

easyncguy52easyncguy52about 2 years ago

that was a heck of alot better then my 1st time

AnonymousAnonymousover 2 years ago

I am a bicurious married man in my 50’s. I fantasize About an experience like this. I would love to be bareback fucked anally. I know I would come hands-free all over.

Riki1942Riki1942almost 3 years ago

Great sexy story, but why would the thought of asking him to pull out ever cross your mind? If I have already had a guy's naked cock and his precum in my mouth and I'm taking him up my ass bareback, it's already too late to worry about any reason to not take his load up my butt.

I have had plenty of sex with guys using a condom but, when I go as far as sucking a naked cock or taking him up my ass bareback, I DEFINITELY want him to cum inside me! It drives me crazy to know that I actually have his sperm inside me!

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