Giving in

This is my true story that I’ve been wanting to share but don’t really have anyone I can tell. A little bit of background, I’ve been friends with my buddy, let’s call him Jay, for many years, almost 20 years. We are both in our early 40’s now.

  So Jay and I as I said have been friends for a long time. He and I have fooled around in the past, hand jobs at first that eventually lead to blowjobs (me giving to him) but never more than that and always when alcohol was involved!

  This time in particular I had gone over to his place to just hang out and catch up. This was also common for us to do, nothing sexual would happen. While hanging out the subject came up that we only fool around when drinking and why that was. I didn’t really have an answer other than that was the only time I had courage to let it happen.

  Jay said too bad as he’s always in the mood and would fool around even if sober. Hearing him say this instantly got me turned on. I asked him...are you asking me for a blowjob Jay? He didn’t reply with words but his smile answered my question.  I could see he was getting hard as his shorts were not very concealing.

So? He said...want my shorts off? I nodded and he complied.

His hard 6.5 inch thick cut cock flopped out of his shorts right in front of me. I reached over and grabbed it and started to stroke his cock but knew I wasn’t going to be able to stop myself. I leaned over and slide my tongue around the tip of his cock. It was like as if it was the first time my brain was able to register this feeling.

  I started to suck his rock hard cock, getting it nice and wet, gliding my hand up and down his shaft as my mouth slide further and further down his shaft. My head bobbing up and down. Listening to him moan and breath heavy.

  I looked up at him and he had such a big smile, he looked guilty.

What? I asked

Nothing, you won’t want to know 

What? I insisted

It’s just that...nothing don’t worry

What? Is it not good? I asked

Fuck no it’s great

So tell me or this is over

I was just thinking...maybe could we go to my room, in my bed and both get fully naked?

 We’ve never both been naked before but why not I thought. So I agreed and we went to his room and both undressed and got into his bed. I returned back to his cock and continued to suck.

  While I was sucking he reached down and started grabbing my ass, eventually moving his fingers towards my hole. I found myself moving my ass to help him achieve his goal. His finger was pressing against my asshole, rubbing it while i sucked.  He then increased the pressure and I felt his finger slide inside me. I was shocked that I liked it.

Is that ok? He asked

Mmmmhmmm I moaned with his cock in my mouth.

He then reached into his side table and pulled out some lube and covered his fingers in it and returned his fingers to my waiting asshole. This time his finger slide in very easy and it felt great.

Mmmm I think somebody likes that doesn’t he? He asked

Mmhmmm I moaned again

He then added a second finger inside me. At this point I was noticing I was finding it difficult to concentrate on sucking his cock as this new feeling from my ass was so good.

I looked up and he once again had that smile on his face. I knew what he was thinking instantly. I had never done anything like this before. But before I knew it I had let his cock slide out of my mouth and was moving my way up ontop of him. My mind was racing, what are you doing, but my body was in control. Now I was straddling him sitting on his stomach I grabbed the lube and covered his cock with it and lathered more lube on my asshole.

  I reached down and grabbed his cock as I lifted my as towards his cock until I could feel it, that moment the head of his cock rubbed against my asshole.

Are you sure? He asked

Fuck me Jay I said... fuck me

  I then started to sit down on his cock and I could feel the pressure against my asshole. I thought to myself this is never going to fit. And that when I remember reading to relax and it will not hurt. I did just that and then I felt it, the moment the head of his cock popped into my ass. It felt so good...I instantly wanted more. The mix of a little pain but over ran with pleasure. I found myself grinding his cock into me more and more...deeper and deeper until I was sitting fully on him, his cock all the way in my ass. It felt amazing!!

Ohhh fuck that feels so good he said and I moaned in agreement. I continued to ride his cock, deeper and faster as I got more comfortable.

While riding him my cock was the hardest I’ve ever felt and without any touch from him I came a huge load all over his stomach and chest. That seemed to trigger him to thrust his hips while I rode him

Fuck I’m going to cum he said. Better get off or I won’t be able to stop.

  That made me grind harder and faster until that moment I felt it. Hot pumps of cum unloading deep into my ass, shot after shot until he pulled my body down to his and pressed our body’s together

 While we laid there together now with my cum on both of our chests and stomachs he kissed me, giving us yet another first!

This is the story of my first time going all the way with Jay...but not the last! That was a year ago, and there have been many more times since, tonight having been one of those nights!

hope you enjoyed as much as I did