Taking The Leap

"A true story of my first Gay encounter and how it changed my outlook on sex and life."

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I’m straight! At least that’s what I tell myself. Throughout my life I’ve had sexual experiences with exclusively women and have enjoyed the heterosexual lifestyle to the fullest.

But ever since my early twenties (now early thirties) I’ve found the beauty in cock. Certainly there are ideal specimens, but a hard cock always meant a good time in my book. So as time went on my fascination and interest in them only increased.

Sure, my love life continued and I slept and orgasmed my way through a plethora of women, even cultivating somewhat of a player reputation; however, I was always drawn subtly back to cock. Of course this part of my personality never became part of the social me, you could even go to the point where my interest in cock would be received with disbelief or rumour-mongering amongst the people who knew me. Even so, I had an itch that I couldn’t scratch.

University was a particularly busy time. With a thick eight-inch cock and a love of eating pussy, my sexual reputation afforded me a freedom in sleeping around. Little would anyone suspect hours of bi and gay porn leading to powerful orgasms (not replicated during my sexual exploits). Soon porn turned to gay app profiles which after some chats and ball-draining picture swapping, would be swiftly deleted and described as just a phase internally.

Suddenly the app profiles stayed a bit longer, some regular chats started to develop, even WhatsApp numbers were exchanged. This was now becoming more than a phase and my conscious struggled to accept what was happening. I had reluctantly and slowly become bi curious at minimum. And the story below is what became of one of those regular chat buddies (for want of a better word).

His name was Dick (ironically). He was an older man forty years my senior, he was kind, understanding of my personal situation (engaged) and most importantly… had a cock and imagination that got me so horny I could barely contain myself.

Even with his wonderful chats and naughty phone calls, his patience was still tested as I wrestled with the internal dilemma as to – am I ready? We’d arranged and cancelled quick meetings so often I was sure he would eventually turn tail and run, finally giving up on this tease.

But everything changed on a opportune Monday morning at the office.

Since Covid and the ability to work from home, my chats with Dick had really stepped up a notch, and it became obvious that we were at a tipping point in our relationship. It was time to make the decision.

He happened to have a second home near my office which he’d strongly hinted at being at his residence for the week.

I was in the office on Monday, and it just so happened to be that he had painters around, so was unable to accommodate on the one day I was nearby (to my continued relief).

As I drove to the office for my morning meeting I received a message.

“Painters have cancelled, how annoying! Don’t suppose you could improve my day?”

My heart pounded. Now I had no valid excuse; I was nearby and was free in the afternoon. This was the moment where I’d make the decision to take the leap or not!

I found myself asking for his address and what time would be suitable to come around, as I saw …. of his response I felt a warmth in my crotch, giving me the sign that perhaps this was the time for action. His response came with an address and a twelve-thirty time slot. I confirmed I would message when I was out of my meeting and on my way.

Needless to say that morning meeting was not a success. My mind kept wandering to what my life would be like later on this afternoon. Would I be a changed man? Would I go through with it? Would I like it? All kept rolling around my mind. And as all things that worry you, time seemed to be moving twice as fast as normal. And all too soon it was time to get in the car and message my soon-to-be lover that I was indeed on my way to his home.

I parked the car on his road and sent the message that I’d arrived. I scanned the street, all normal-looking homes, none of them giving the impression that one door was soon to change my outlook on sex. Then as I watched I saw a door across from me open and saw Dick in the flesh for the first time. He opened the door, scanned the street and retreated back inside. I opened the door and was surprised at the speed I crossed the road.

I stepped over the threshold and closed the door behind me. As I walked in the living room there he was, standing, waiting for me. He was smaller than me (I should mention I’m 6’3″ and have played rugby my whole life which thankfully keeps me in good shape), had a warm smile and gave me the overwhelming feeling of kindness and warmth. Without a word he held my head in his hands, looked me straight in the eye and smiled, before leaning in for my first kiss.

I felt his lips press mine in a warm peck. After faltering initially I reciprocated in a polite kiss. He held my head in his hands and placed another kiss on my lips, this time pulling me closer in to a warmer, deeper kiss. Again I reciprocated, letting him take charge in the moment.

Then it happened. I felt his tongue break free, slide my lips apart and fill my waiting mouth. My tongue reacted instinctively and slid out to meet its newest partner, as we finally, after over a year of sexting and mutual masturbation, gave in to each other.

Things escalated quickly. Dick was a good kisser and craved tongue, so for what seemed minutes we kissed deeply – our hands starting to wander and grab each other closer. My cock started to harden through my jeans and Dick quickly tore my baseball hat off to pull our kiss deeper. We broke apart at times to catch our breath but the need for each other was so strong we kissed again, not wanting to stop.

Eventually we reached the sofa where we kissed and groped at each other like teenagers, my cock now as hard as it had ever been for any woman! Dick pulled back and got up. He went to fetch some drinks from the kitchen. I sat there, my lips hot from snogging, my raging cock in my jeans, and feeling a little light headed. As far as my fantasy went, this was living up to everything I’d imagined.

When Dick returned, he asked some questions around my sexuality, worried that I was hiding away who I was. He offered some advice and asked about general things, while we sipped on a glass of fizz which he’d saved for the occasion.

In all honesty my mind was firmly in the gutter at this point and my lust was taking over! I took his glass from him mid-sentence and placed it back on the table. In an act of horniness I straddled the older man and went back to some deep kissing, tongue heavy as I felt him grab my ass. I felt a feminine moan leave my lips as I gave in to him, accepting that I wanted him!

My raging hard-on taking the lead, I slipped off to sit next to him and pulled my thick eight-inch cock from my jeans! I squeezed it hard as it stood proud for him. We kissed as he finally took it in his hand and stroked it for me. Moaning openly now for my gay lover, my cock leaked clear precum down my shaft. Dick slid his thumb over it before letting me taste myself from his fingers.

He kneeled between my legs, my cock centimetres from his lips. He looked at me, ready to devour my cock, but I hesitated and pulled back; I wasn’t ready for that next step just yet.

Dick suggested we go upstairs to the bedroom to get more comfortable. Dick gave me a small tour of the house, every room being used as a new place to kiss and squeeze at each other. An enjoyable ten minutes passed as we made our way through the house! I was shown views out of the window as my cock got stroked and my neck kissed. I recall the memory often; being held and wanted by another man still makes my cock twitch.

Once in the bedroom we both got undressed and got on top of the bed. Dick now took more of the control as he lay on top, our cocks rubbing together as we continued a frenzy of kissing. Feeling his long hard cock rubbing up against mine, my legs naturally parted for him, almost inviting him to fuck me on our first meeting. I felt the head of his cock against my virgin ass as our tongues continued to fight each other.

The situation was getting the better of me. I couldn’t hold back from stroking my cock hard. Between the moaning and kissing I was all of a sudden in the later stages of sex! As we lay next to each other furiously stroking and kissing I couldn’t contain myself. As I moaned that I was going to cum for my daddy my cock erupted. Three, four thick ropes of cum gushed out of my swollen head, covering my stomach. I looked down to see Dick adding his hot jizz to the load as he came over me at the same time!

We lay there panting! Hot cum covered my stomach as realisation dawned on me! I’d just cum as hard as I ever had! For a man! My mind went in to overdrive. The last thirty minutes of hot kissing, touching and stroking had been so fulfilling. Did this mean I was bi? Was this now more than a curiosity?

I’m ashamed to say I panicked and made a quick goodbye to Dick with a promise to see him again. I drove home, showered and tried to block out what I’d just done.

It wasn’t until later that night that I found myself horny at the memory of the afternoon that I realised I’d enjoyed myself.

Fast forward a year, and Dick and I are still in touch. However, I haven’t seen him since that visit.

For this year I think the guy deserves another visit.

Published 2 months ago

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