First time trying anal.

I didn’t actually write this one, a very dear friend called Wendy wrote it and asked me to have it published, here we go – be kind to her in your comments:

My first time trying anal was with Chris my b*****r so I would have been in my early teens. Somehow, it wasn’t done deliberately, well, I suppose it was, but not like, “Well we have tried everything else, might as well try this.”

It was like just experimenting and meaning so much to each other that we couldn’t wait to try everything and that was just part of what we were desperate to try.

From the size of my pussy, he could see just how difficult it was going to be and from when he used to fuck my little pussy and he played with my bum hole, he could see that I was able to relax somewhat so that he could at least get a finger in my bum at the same time, but it was going to be very different if he wanted to get his cock up there.

He was so patient with me, we would fuck properly first and then he would suck all the cum out of me and use it to work on my bum, he would take his tongue and push it up inside my bum, then pull it out and with his mouthful of cum now up inside my tiny bum hole, he would work his finger in and out of me.

Of-course, every time he stuck his finger up inside me and started to wriggle it about, at first I would grip his finger and go all tense, he would talk very lovingly to me and gradually get me to relax, finally, I was going crazy with his mouth on my pussy sucking me dry and his finger up my bum ploughing it in and out of me faster and faster.

Many of the times at the beginning, he would get me to the point where I just couldn’t take any more and he would pull his finger out and just cuddle me whilst I cried into his shoulder and told him how sorry I was.

He would never go off in a huff and he really made it feel as though it was ok, but I knew I had to grow up and not act so silly and slowly I taught myself to take more and more from him.

Finally it came to the point of him actually trying to get his huge cock up there and I made the decision as to when it should be just like he told me to time and time again.

He was on top of me with my ankles over his shoulders and he was pounding away at my pussy, my juices were literally pouring out of me and he was working more and more of it up inside my bum.

Suddenly, I felt as though if I don’t cum now, I’m going to blow up and make a real mess of everywhere and without thinking, I pulled back from him so that his lovely cock flopped out of me, I put it at the entrance to my bum and he slowly eased it just inside.

It didn’t make any difference to how I thought my mind was going to react to it, I just clamped shut and pushed him back out with my sphincter. I started to cry and begged him to try again, he did, but I just couldn’t relax and he got no-where near putting it in me after that.

Again the next time, I was laying on top of him and as we got out of our beautiful 69 and I was as open everywhere as I was ever going to get, I spun round and lowered my bum onto his rock hard helmet.

We both held our breath as we watched each other and I lowered myself down a fraction of an inch at a time. I know I was waiting for it to tear me apart, but it never came, more and more of his cock disappeared up inside of me and when I had about an inch in there, I flopped down on his chest so that I didn’t have to squat any more and just kissed him as hard as I could.

He didn’t move at all, I didn’t either but I could feel this huge tool twitching in my bum and it felt really fantastic, no, beyond that but I can’t think of the right word to describe it.

I asked him if he was able to move at all and he said something that I thought at the time was really strange, it makes perfect sense now, he just asked me “Which way”, which way did I want him to move?

Well up of-course, but he didn’t know what I was thinking did he. Well I told him which way and he watched every muscle in my face as he did pull out a tiny bit and push further in, very slowly, he was encouraging me to set up a rhythm with him which I found surprisingly easy to do.

The trouble is, it didn’t take me very long to start to get dry and then an even shorter time to get sore, so without saying anything to me, he pulled out, rolled me over onto my back and gave me huge kisses to thank me with as much love as he had.

We didn’t just keep trying it until we got it right but yes, we did do it again and we tried even more often than we were actually capable of doing, but we were so much in love that it just seemed so natural for us to do it and to keep trying until that glorious day when he was able to get three or four inches up inside of me and it was me doing all the moving.

I was clamping his cock as hard as I could with my muscles and literally wanking his shaft with my bum muscles. To think, the very same thing that had kept us from doing it properly for so long, I was now using to bring him off.

And my god, bring him off I did, he exploded. I don’t know if I have told you, but like me, he sometimes has an orgasm that is so much unlike his normal ones. When he cums like that, he doesn’t pump wad after wad of cum up inside me, it’s as though he’s peeing in one long blast of cum, no break, no jerks, no four, five, six or seven blasts, just one huge one that seems to go on for ever.

And I don’t care what other women have told you, maybe they have never experiences something like that but I felt it, I felt every inch of cum that blasted up inside of me. When I first felt it, I started to laugh and I grew hysterical, I looked at Chris and he hadn’t breathed for about thirty seconds and his veins were sticking out all over his face and he was such a strange colour.

At first I thought I must be hurting him so I stopped laughing and started to pull off him, but he grabbed onto my waist and screamed out “NO”.

I immediately smiled again because I knew that he must be in intense pleasure so I just sunk back down to where I was taking even more of him and slowly wanked him with my bum.

Finally, he took a huge gulp of breath and all I could feel was still this spear up inside me and gallons of cum sloshing all over my bowels. I kept up my rhythm, until he finally opened his eyes and asked me to stop because he had to go and pee.

I just looked at him and raised my eyebrows and shrugged my shoulders. He saw me do it and he knew what that meant.

“Oh no, you’re really going to make me do it aren’t you?” he said.

I didn’t answer, I just kept slowly pumping him.


95% (22/1)
Categories: AnalFirst TimeTaboo
Posted by pinks43
1 year ago    Views: 3,673
Comments (5)
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1 year ago
That's fucking wild! I want to do that to my stepdaughter.
1 year ago
fuck, that's hot! on to part 2
1 year ago
1 year ago
Did he then pee in your bum?
1 year ago
fab horny story,loved it.