Tim's DILF

My best friend Tim was the first person to know I was gay. He was straight himself, but he didn't mind me being gay. But there was something about his dad that I thought was really sexy.

His dad was called John. He was around 40 years old. I was 21 and had never been with an older man before, but I wanted to get with him. He was over 6ft tall (towering over me, I was only around 5ft 6 at the time), and he was pretty well built. He had short, greying hair and green eyes. Whenever he greeted me I would stare deep into them, often drifting off into a fantasy world. After a few times of seeing him, I started noticing him giving me looks.

I got a call around 7pm one night from John. He asked me to come round. I came round thinking Tim wanted to see me but John was the only one home. He answered the door in a dark blue, tight polo shirt and jeans. I could smell his aftershave; it was strong but really nice. He invited me in and got me to sit on the sofa, and he sat down next to me. I asked him why he called me over, but he didn't answer. He simply put his hand on my leg and gently squeezed it. I looked him in the eyes and he went in to kiss me. I pulled back and said, 'I'm not sure if I can do this...what about Tim, or your wife?'

'They don't need to know,' he replied softly. 'What they don't know can't hurt them.'

John was sat with his legs apart, so I sat on his lap, facing him. I unbuttoned the 3 buttons on the top of his shirt, exposing his hairy chest. He was a very manly man; I never would have expected him to be gay. I kissed him gently on the lips before he pulled his shirt over his head. I stopped him, so his shirt was covering his face. I ran my finger down his muscley arm, until it reached his armpit. I stopped and smelt it - the smell was a mix of deodorant and sweat. I then worked my way down to his chest. I started to lick and suck on his right nipple, whilst playing with the other with my finger. He chuckled and wrapped his arms around me, squeezing my ass and massaging my cheeks in his big hands. I pulled his shirt all the way off of his head, and met him nose-to-nose. He breathed heavily, his breath tickling my neck.

I pulled off my shirt and grabbed his hand. I trailed his fingers down my chest, over my nipples and to my fairly toned stomach. I let go of his hand and it went straight for my belt buckle. He undid it before pulling it out of my jeans, and throwing it on the floor. He opened up my button fly and pulled down my trousers, leaving me left in nothing but my socks and boxer shorts. I was wearing tight, light blue boxer-briefs which hugged my bulge. I was around 5 inches flaccid, and 7.5 inches erect. I was still soft, but as John put his hands down my pants and started to play with my asshole, my dick got harder by the second. John still had his trousers on, but as I rested my dick on his crotch I could feel him getting hard. I could feel it was big, so I looked him in the eyes and he gave me a sexy half smile, before nodding his head, signalling me to get it out.

I undid his belt and slid his jeans off; he was wearing skin tight, black briefs, and I could see a spot of precum at the tip of his dick. I went to take them off but he stopped me, leaving us both in nothing but our underwear. He got me to stood up and he followed, his big hands still resting on my butt cheeks. He kissed me on the forehead, grabbed me by the wrists and turned around. He bent over, resting his chest on a pillow. He told me to ‘tease him,’ and I obeyed. I couldn’t say no to him; his voice was deep and sexy, and his body was too hot to resist.

He was bent over the sofa, and his tight briefs were rising up into his bum crack. His ass was perfectly round. I hadn’t seen anything like it. I massaged the cheeks before pulling them apart, allowing his briefs to go deeper into his hairy crack. I still had my boxers on so I opened his cheeks further and started to dry hump him. I was rock hard and I could tell it felt good as he was softly moaning. I humped him harder, before stopping and pulling the back of his briefs down, baring his ass but keeping his monster covered.

His hole was tight and pink, but quite hairy. I moved closer and began to lick it, before sucking my fingers and sticking two of them in. He moaned as I fingered him faster, his tight asshole pulsing around them. I took them out of him, before spanking him and sitting down on the rug with my legs wide open in front of me. He got on his knees and crawl over me. He then, still on his knees, straightened his back so he was over my chest, and slowly pulled down his briefs. He was hard but he was slowly taking them off, so his thick, throbbing cock slowly appeared out of them. He had a big bush of pubes above his long thick cock. He got his briefs all the way off and his dick sprang up. It was easily 5.5 inches round and 9-10 inches long. He held it in his big hand, looking me in the eye and laughing at my shocked expression.

 I grabbed it in both my hands and took about half of it in my mouth. I bobbed up and down it and made John moan and grunt with pleasure. I sucked him until he was about to cum, before taking him out of my mouth. I took my dick out and John spat on his hand and gave me the best hand job ever. He played with my ass and balls with one hand and wanked me off with the other, and he let me explode all over my stomach. He licked all of the cum off of me.

I lay on my stomach, with my dick in-between my legs, and spread my ass open for John. He lubed up his monster cock before slowly penetrating my tight asshole. He went in inch at a time; I was moaning and grunting in pain and pleasure. He had all 10 inches in me, so he rest his hips on my ass and softly moaned my name, before asking if I was ready. I reached around and grabbed his ass and replied yes. He pulled his dick out almost all the way, before slowly entering all the way in again. He got faster and faster as I groaned louder. I could hear his hips slap against my ass as he got so deep. He was dominant; he was always in control. His cock made my ass hurt like hell but he felt so good inside of me. He pulled out and sat down, and he got me to slowly sit down on his dick. I bounced up and down on him, and we were both sweating and moaning. He was the best fuck I’d ever had. He moaned loud as he cummed deep in my ass, before pulling out and cumming all over his chest and mine.

He laid back with his arms behind his head, and I lay on top of him. I kissed his lips before slowly fucking him up the ass, making him softly moan. We fucked until late at night, before going up to sleep naked in his and his wife’s bed. This wasn’t the last time we had sex either, we stayed together for plenty of times after.