The Ever Elusive Anal Sex Story...

Hi everyone, if you haven't guessed by the title, this blog will be all about anal sex and my experiences involving this exciting sex act!  I have been lucky to have this experience, but in the more recent past I find it very difficult to find a willing party.  Maybe some of my loyal readers will have some ideas of how to make this a much more common activity for me.

My first experience with anal sex came when I was 18 years old and working my first ever job in the fast food industry in the Nepean area.  I won't name the actual chain, but it's one of the top 4 chains I around town.  This is the perfect job to meet girls who are open to all sorts of things.  I found the girls in these jobs generally had values that were certainly on a different level than what my family taught me (not that I ever listened).  Don't get me wrong, I am not judging them or their families and in fact, I have made some long lasting relationships with people from this job.

Me and this very pretty girl named Chantelle, about two years younger than I struck up a relationship.

Turns out she had previously been in a couple of bad relationships.  However, she was the most loyal and devoted girlfriend I have ever had and perhaps to some extent this had been her downfall in the past, no matter how her boyfriends treated her she would not let that negatively affect her view of them.  Chantelle was a slender, blonde girl with a very cute face.  Her hair was short just above her shoulders and caressed her face.  She was small breasted but perky and had an amazingly tight ass that only a young woman could have.  The kind of girl that just fits so perfectly under your arm.  Despite her very innocent look she had a lot of interesting experiences for her age, not all of which were positive.

When our relationship progressed and we began having sex I had quizzed her about her past sexual  experiences since I did not want to push her too far too soon.  I found out that she was as equally experienced as I was and in fact, perhaps a bit more experienced.  She had tried anal sex with her previous boyfriend and she said she said that she did not love it but had no problems doing it.  I put that in the back of my head and we began having amazing sex.  I remember sneaking off to the local nature trail in the dead of night in my Dad's station wagon.  After making out in the front seat for a bit we would lay back the seats and climb into the back and continue.  

We'd always take it slow, her shirt would come off first and I would suck on her firm, perky tits, she had those perfect pink nipples, perfect circle, and erect.  While I sucked her tits I would stroke her flat stomache, my hand inching ever nearer towards her cunt.  

She would make a move to unbuckle my belt and pants and start stroking me before moving down to take me inside her mouth.  When she came back to me I would have her wiggle out of her pants, pull off her tiny panties and slowly make my way down her body stopping constantly to kiss and suckle as I made it to her waistline.  I would ease my fingers inside of her and start licking her clit.  I would taste her until I heard her begin to moan and writhe in pleasure before climbing slowly back up her stomach and pausing to play with her erect nipples before sliding my cock inside of her wet pussy.  

We would fuck for a while in the missionary position but she liked to ride me, so after a few minutes we would switch places, allowing me to squeeze her tits while she fucked me.  When I was just about ready to cum I would have her get back on her back so I could be in control while I would cum inside of her.  

I can still picture her pretty face, neck arched back, moaning sweetly as I would pump the last bit of cum into her.  Often times I would prefer to finish in her mouth or on her face.  She was always willing to please and would always do as I asked.

That was our normal routine, sometimes, naturally we would throw a little doggie style in the mix, although, it was never that easy with the roof of the car always getting in the way of my head!  

As our relationship got more serious I finally brought up wanting to try anal sex since I have never tried before.  She was more than willing and we started looking for an opportunity to give it a shot.  Since we were both living at home, and I was driving my dad's wagon at the time, it was not always convenient to plan something that would allow us to get away and have the opportunity for our first anal escapade.  Finally, we made our way to a nature trail again, however, it was not our regular spot and it was in an area with more nearby traffic, and we were not in the wagon, but rather a smaller coupe style vehicle.  We planned for a quick blow job before moving along.  

Chantelle being the sexy little girl that she was started sucking my cock, but before long I wanted more and I had pulled her up to play with her tits.  I could not resist her flat stomach and made my way down to feel her flat tummy while we necked.  The passion and urge took over and I unbuckled her belt and pants and slid my fingers inside of her.  Although, being slightly worried that someone would have the same idea or worse yet some cops coming to check up on the area I decided to have her wiggle out of her pants.  I slid over to the passenger seat and she dropped her wet pussy on my throbbing cock.  

We fucked for awhile, and while she was riding me she whispered in my ear "Do you want to try it in my ass?".  I did not hesitate and she slipped her cunt off of my cock and I struggled to put my cock in her ass.  I was not having much luck to be honest, so she took control grabbing my cock and guiding it right into her asshole.  I slid in without any trouble at all and could not believe the amazing sensation of her tight asshole on my cock.  

It was not something I had ever experienced and I had not ever experienced anything like it.  I was loving it, and loving Chantelle for sharing this with me.  We necked while I fucked her ass and squeezed her perfect tits.  It was not long before I was filling her ass with cum and moaning hard for her.  

This was not the last of my anal sex with Chantelle, far from it.  We would sort of rotate from regular sex to anal sex.  I wish I could find that in a woman again!  We had more experiences in my Dad's wagon, I remember fucking her ass at the drive-in that once existed in West Ottawa.  Just before I finished she complained that it hurt and asked me to stop, but she let me finish since I was nearly done.  

There was something distinctly erotic about fucking her and hearing her moan in pleasure in pain, something similar to when you fuck a virgin and she is loving your cock but begging for it to be over at the sametime.  We once fucked at her friends house during a house party, in the same room as another couple also fucking in the ass that night.  I will cherish my time with Chantelle for many reasons, but I would be lying if the anal sex and other daring sex stories that I have from my time with her.  If you are ever reading Chantelle, I loved you very much and thank you for everything you did for me.  

That is my story about first time anal sex and my first anal sex girlfriend.  I had planned to include several other anal sex experiences, but I fear this post will become too long and repetitive.  Therefore, I will save my other stories, perhaps for a later post.  Please leave you feedback, comments, questions, suggestions, or concerns by commenting on my blog.  I would love to hear from all of you.  If you were not a fan of the anal sex stories then let me know and I will skip the other ones I had in mind, or if you are a big fan of them... say it with a comment!

Thank you, Read again! (in my best Pakistani accent).