Daddy pops my cherry

I had just turned 18 and joined a gym for the first time in my life to bulk-up as I was the quintessential twink at that point in my life. I was a late bloomer, painfully shy and struggling with my sexuality. I was desperate to be fucked and horny as hell. I was a virgin and didn't feel comfortable experimenting at my all boys high school for obvious reasons.

I kept to myself the first few weeks when training at the gym but eventually an older man struck up a conversation with me. This mans name was Bernard, he was a gym regular and was 50-60 something, retired primary school teacher, 5'8, White/blue eyes, short snowy white hair, manicured short beard, pot belly, average build and hairy. While he wouldn't be conventionally attractive by most standards he was EXACTLY my type. I was raised fatherless with no male role-models and had your typical daddy issues. Bernard would have absolutely no trouble getting my on the bed. I was/am partial to that traditional masculine traits.

Bernard and I became acquainted and would semi-regularly see each other at the gym and would make small talk, nothing salacious. This continued for a few months until I bumped into him at a cafe in the local Westfields. I said hello and joined him for a coffee and a chat. The tone of the conversation was different and he eventually revealed that he's gay. I was genuinely surprised at the time but excited to hear it. He then said he was heading home and invited me back to his place for a drink, I enthusiastically agreed. We silently walked to the carpark and hopped in his car and made small talk on the short drive to his local flat.

We went inside and we sat on the couch and shared a glass of wine after a few minutes we started talking about cocks and it started to get steamy. He asked if I has ever seen another one, I said no and he casually stood up and unzipped his pants and took out his firm, uncut 7.5 incher. I started at it in amazement, he sat back down and rubbed my back with his hand, he said "don't be shy". I promptly dropped to my knees on the floor and kneeled between his thighs and gave him a blowie.

He relaxed on the sofa while i sucked him off for 20 minutes or so, he would occasionally give instructions as this was the first cock I ever sucked and my technique must have left a lot to be desired. Afterwards he guided my face to his mouth and he instructed me to jerk him off while we kissed on the sofa. This continued for a few minutes until he began to casually strip naked and ordered me to do the same. He booted up his laptop and placed it on the coffee-table and we began watching amateur porn clips together, mostly involving twinks being ploughed by daddy. We discussed what we liked, out turns on, preferences (top v bottom, our dream man), shared experiences with me disclosing I'm a virgin.

He then pointed to a doorway and told me to go inside and get on the bed, I nodded and went inside the room. I had fantasised about getting fucked doggy-style so I got in said position and waited patiently. He soon came in the room and walked to a drawer beside he bed, opened it and pulled out a bottle of lube. He walked directly behind me and gently gripped my hips with his hand and I felt him place his lubed tip gently over my asshole. I was very nervous and anxious so went dead silent and just let him do his thing.

He then began to gently penetrate my asshole, slowly and cautiously, gauging my reaction and responded accordingly. It took a few minutes but he eventually worked his tip inside me and began to repeat the process with his shaft. There was naturally some initial discomfort/pain but I pushed through it reasonably quickly/easily and he began to gently and slowly plough me. Despite his age his cock was still nice and hard.

I was overwhelmed and was silent while he fucked me. Bernard began to moan and sigh with pleasure as he worked up the pace and ploughed slightly harder/faster. After a few minutes he pulled out and came on my cheeks. He collapsed on the bed next to me, exhausted.

This was the beginning of a long-term Friend with Benefit situation. Afterwards, Bernard and I would regularly fuck and go on social outings together such as gym workouts, movies, coffees,, gay clubs/bars/events etc

This arrangement lasted around 8 years, we would see each other regularly (fucked countless times) and in addition to being a fuck-buddy he became a mentor and taught me so much about life in general.