Loosing my anal virginity

Hey guys, so I'm Boe and this is the story of me loosing my anal virginity to my best friends father. The whole story is 100% true but changing the names of the other player for privacy.

It was a normal Friday night for myself my best friend John and his girlfriend Ally. We had all withing the last 5 months turned 19. So we could finally hit the bars together. 

Im six foot and not a twig but just a bit past. I no longer had my six pack from my early teens and hitting the gym but was far from out of shape. Long jet black hair just past my shoulders and a well trimmed beard all the qay around. I considered myself a fairly straight guy at the time but as most young guys had once or twice thought about gay sex but nothing more of it. 

John's father Jim just so happened to be a great guy and super handsome in his early fifty's, bald up top but a crew cut the rest of the way around. About 5'10" and always wore things that showed off his nice dad body he had going. 

After a few drinks and joints john said we should all go out to the bar for a bit and have a few drinks to wait for his dad to get off and we could all cab back and keep the party going. 

We got to the bar around 1 in the morning. So lots of guys were still there causing and I got more than one wink and nod. I just sat by the bar and had a few drinks chatting with the bar tender who I had known for years as a friend of the family's.

Just after 2 John and ally were ready to leave and I could see they wanted to be alone so I offered to stay and help clean up after the shift was over. Jim knew what was going on so after we finished and everyone had left he cracked a few beers and said "Fuck it, may as well have one or two more for the road and give them some time to cool off". I laughed and made a joke about how they were the lucky ones to get laid that night.

Soon we were off back to Jim and John's place where I was spending the weekend. When we got in John and Ally were both passed out so Jim asked if I wanted another beer and to smoke a joint before we each went to bed. (Who wouldn't? And by this time I wasn't super drunk but was feeling a nice warm buzz all over.)

We chatted for a bit while getting high and it was down to the end so Jim took in a deep haul and moved closer to give me a super, I took it and then he did another but got much closer this time. I wasn't sure what was going on but I knew I was feeling good and hot. That when he did the third super and we locked lips and started to just make out like we had just discovered what it was. 

He was very gentle feeling me up and down, he dropped to his knees and undid my belt. I have a decent 7 inch cock that is fairly thick and uncut. Jim took the whole thing down in one shot. I had never had that happen before in my life. It felt amazing. He sucked me for about ten minutes and then stood up and told me to get on my knees.

I was so horny by this point in time I would have done anything I was asked to do. A little hesitant but it was only a flicker for a moment. What I never knew was that Jim was packing a fuacking monster of a cock. Ten inches and was about as thick as a water bottle. My eyes popped and my mouth just started to water. No second thoughts I went face first into his crotch. Smelling and tasting him as he slapped me with his massive dick.

I slowly worked the head in and out of my mouth for a long time getting used to the size and slowly started to take more. Jim didn't shove me down but would hold my head in place and slowly pop the head down my throat. I thought it had only been about five or ten minutes but apparently I had been sucking him for about 45 minutes and my jaw was killing me.

Jim smiled down at me and said "Your harder after sucking my cock than you were with me sucking yours. Quite the bottom fag I pulled for myself" I looked down and saw I was harder than I had ever been before I my life and all I wanted was more but my face hurt and I couldn't keep going. 

"Well there is another thing you can do for me but only true sluts and bottoms can do it." He said chuckling to himself knowing that I was so in his power he could do anything to me. And he was right, he didn't even have to ask. I quickly and quietly as to not wake my best friend or his girlfriend in the next room went to Jim's room and got on the bed on all fours with my ass up.

He walked in behind me and laughed to himself and said something about me being a good boi and to brace myself. I was to amped up to really hear what he was saying to me. 

He came in and spread my ass cheeks apart as far as they could go and just ate my ass like it was the last one he would ever taste. After about 15 minutes of him eating my hole and using his tongue to prepare me to be opened up. He withdrew his tongue and slid up my body. I didn't realize until that moment how much chest hair he had and it rubbed right up my smooth back tickling and scratching the whole way. 

He now had his cock between my ass cheeks and was slowly humping away in the spit he had left that made it just slip back and forth. He leaned in and bit my ear lobe lightly and said " I'm going to fuck you now boy. You had best put a pillow on your mouth and clamp hard, we don't want john to see you with my cock up your ass now do we?" 

In that moment I wondered what would happen. All I knew is I wouldn't stop anything. 

Next thing I know I feel Jim's large head pushing against my ass hole. Now I had never had anything in there before and felt it start to sting. I tried to move forward but Jim just said no and threw all his weight on me. All of a sudden *POP* the head is in and the rest just followed all the way in. I screamed out and Jim held my face in the pillow. He waited a moment for me to get used to his size. (I didn't really) and then slowly Started to work himself in and out of me. 

Soon enough he is using full strokes to just plow my ass and I'm at the breaking point. I touched my cock and shot the biggest load I have ever had in my life. Jim saw this and pulled me back until I was face to face with my own load I just blew. Next thinf I know he tells me to li k it clean. No cum stains on the sheets I have been told. 

Here I am licking my own  cum up while being fucked hard from behind. And I all I can think of was "when can I have more?" Sure enough as almost on cue Jim tells me he is going to cum. I tried to ask for a facial but he buried himself balls deep and came hard in me. Feeling him twitching and pulsing as his large load filled me. After he pulled out he stuck his softening cock in my face to be cleaned. I smelled his cum and dove on again.

After we both dressed again  I went to pass out in the living room for the night wishing I was with Jim.