Anal Sex – My First Time Anal

Anal Sex – We were inexperienced teenagers.  Me – young, blonde, eager.  Him – tall, dark, handsome, and my massive crush.  Two weeks ago he took my virginity and I was crazy in love with him.  Which is why I gave it to him freely and unconditionally.  We were at a mutual friend’s house while her parents were out of town and escaped the gathering up to her parent’s bedroom.  Not gonna lie.  I was hoping this time with him would be much better than our first time.  My first time.

We made out as teenagers do.  Kissing.  Fondling. Stroking. Feeling.

He got up and locked the door.  Took his clothes off and stripped me naked.  Told me to get on my hands and knees on the floor.  Promising me that in this position it would be easier and feel much better than my first time.  I did as he asked hoping it would be better than before.  Because before was painful and terrible.  I sensed him coming up behind me and it happened.  All of a sudden his older, teen, hard, young cock was buried.  But not where I expected it to be.  It was in my tight, sweet, virgin ass.  No lube.  No preparation whatsoever.  And it HURT.

Burying my face in the white carpet as he pounded me.

I thought WHY?  WHY?  He grunted and shot his load of hot cum inside of me.  Pulled out and collapsed next to me and asked if it was better this time?  I sucked it up and said it was okay.  Still trying to wrap my head around what just happened.  Years later and still in contact with him, I finally got up the nerve.  I asked him about that day.  He was embarrassed beyond belief and literally had NO idea that he got his cock in the wrong hole.  Mortified was more like it.  Even though he was older, I guess he was just as inexperienced as I was.  Within my first two times – Both Cherries Popped.  Next????

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