My best friend Brian made a confession to me last week.  We were hanging out and drinking quite a bit.  I don’t know if he remembers what he told me or not, but I remember, and that’s what is important. We were talking about things that we fantasize about  but haven’t worked up the courage to try just yet.  He told me that has always had a fantasy of having either a woman pegging him with a strap on, or playing with a tranny.

He has never told any of his girlfriends because he was afraid that they would think it was gay or something.  Why do so many guys think this? I can’t speak for all women, but I think it’s hot as fuck when a guy is secure enough to be that vulnerable with me.  I wanted to make Brian’s fantasy a reality so bad!!  The following weekend I told him to come over and hang out with me.

He thought we were just going to watch a movie but it was going to be a little more hands on than just that.  We sat on the couch and I hit “Play”.  A busty blonde came on the screen wearing a strap-on.  Brian started shifting and asked what we were watching.  I told him to just watch, it gets much better.  She walked over to a man who was sprawled across a bench. She lubed up his tight shit hole and started to slide in her nice big piece of rubber meat.  Brian’s breathing got heavier and I reached over, putting my hand in his lap. He was so hard that I could see the outline of his mushroom head through his pants.  I gently squeezed him and asked if he wanted to try that with me.  He seemed surprised but nodded and I took him into the bedroom.

We stripped down and he watched as I put on the strap-on.  This one was a little special.  It was double sided so half went inside my wet opening as I got to penetrate him with the other end.  I picked up a bottle from my night stand and made a show of lubing up the dildo.  I slowly slid my hand up and down my rubber shaft, pretending I was jerking it off.  Brian stared at me as he reached down and began to stroke himself in time with my movements.  When it was nice and slick I told Brian to get down on all fours.

He did and I got on the bed behind him. I put some lube on my fingers and spread it on his hole before pushing my middle finger inside of him.  He clenched tightly around me as I moved my finger in and out of his hole, loosening him up.

When he was relaxed I put my hand on his lower back to keep him still and began to push the dildo inside.  When the tip went in, he tried to pull away but I firmly pressed down on him.  He gasped and squirmed as I slowly pushed it in deeper.  Pulling it almost all the way out and then going deeper each time I pressed back into him.  I didn’t stop until all of it was in him.  I gave him a minute to get used to the feeling then gave a small thrust.  He was okay with it and I got into a steady rhythm, sliding the dildo nearly out of him before shoving it in deep.

Soon he was rocking back and begging me to fuck him harder.  I reached around and grabbed his dick.  I stroked his meat in time with my thrusts in and out of his tight man pussy.  He began to moan non-stop.  I moved a bit faster as he let out a deep groan. I was hitting his prostate just right.  Then I stroked him harder, jerking up and down while giving a little twist on the down stroke.  He grunted and his seed shot out, covering my hand as I pressed my dildo deep inside of him, milking out every drop.

I slowly slid out of him and he collapsed on the bed. I lay down beside him and said that I’d be helping him explore his kinks from now on.  He pulled me into him, gave me a big kiss, and told me that I was the best friend anyone could ever wish for.  My fantasy got to come next though…Give me a call and let me tell you all about how he made my kinky ideas come to life!!

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