Popping My Anal Cherry – Getting Ready for the First Time

Dear Adam and Eve –

I want to thank you for making my boyfriend’s sexual dreams come true.

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When I asked my boyfriend what he wanted for Valentine’s Day this year, he turned to me with a cheeky smile and said, “anal”. I thought he was just playing at first, but after a bit of discussion, he said that he really wanted to try it. We had been together for years, and our sex lives were getting a bit on the stale side. I have always been open minded about trying new things, but I had a bit of a fear about anal sex. Would it hurt? Would it get messy? Would it do any damage? I tried to convince myself that loads of men and women have anal sex all the time, so there must be some kind of positive side to it.

Whenever you see girls in porn movies get a cock slipped in their ass, there’s never any kind of mess. What I found out is that most of these ladies douche before they perform. When I logged onto your site, I found a douche just for this very reason! After I added that to my inbox, I clicked around and found a few other items that I had read were must-haves for first time anal – lube, small toys and larger butt plugs.

I knew that I needed to start small and work my way up to a size that was similar to my boyfriend’s cock. I wanted to spend a bit of time on my own before involving my partner. I got into a comfortable position on my bed, grabbed my favourite clitoral vibrator to get me in the mood, and just relaxed. When I started getting close to cumming, I slipped the small toy up my back side after lubing it up. It was a strange feeling at first, but as I moved it in and out, it became easier to deal with and added a new sensation. I came hard with the toy in my ass and my vibe pressed against me, and I was pleasantly surprised at the whole experience.

Over the next few days, I kept going with my little toy. After a week, I moved onto the butt plug. This was a bit harder on my body and it took a few days for it not to be painful as I pushed it in. I even needed to take a day off after the first time I used it to make sure I wasn’t doing any kind of damage. Thankfully, I still came every single time I used it, and I knew that my body was starting to enjoy the anal penetration.

After about three weeks of training, I was comfortable enough to get my boyfriend involved. He started off by fucking me with the butt plug while fingering my clit. He told me he got so turned on by the whole thing that he could barely keep himself from taking me then and there. The day that I finally let him slip inside my butt, he came within three strokes! (He’s not usually that quick – trust me!).

I was so glad that I found your helpful tools, as well as the research I did on the internet about anal training. It made an experience that I was quite scared of one of the best sexual episodes in my life!