Saturday, March 30, 2013

Dear Diary: Anal Sex

Dear Diary,

I have always been terrified of anal sex. I had a terrible experience with a guy I was seeing when I was much younger and that experience shaped my entire view on anal anything. I held a strict "Exit Only" policy and there was no discussing where I stood. There was no way in hell I was going to allow myself to go through that much pain again.... Let me stop here and give a little background on what happened with this guy I am going to call Tim. Tim was the bad boy and I was instantly attracted to him. Big, baggy goth style pants, skater shoes, edgy t-shirts, huge gauges in his ears, and an I-don't-give-a-shit attitude. At this point I was still in high school and rebelling in a way that if my kids ever do I will kill them immediately raid their college funds to pay for a therapist. Anywho, I starting "seeing" this guy (and by seeing I mean skipping school to hang out, smoke pot, and consume large quantities of fat inducing junk food).  At this time in my life I had no idea who I was or what I wanted. My self-esteem was not just lacking, I had none. I though I knew so much but I was so blissfully naive about the real world. It wasn't long before he had me in his bed. I will never forget having sex with Tim and enjoying it then with absolutely no warning I felt a searing hot, body spasming, breath stealing agony in my ass. When I screamed he chuckled, blurted out an insincere sorry, and tried to continue where we had left off. This was my introduction to the world of anal play.

Obviously this was not the ideal way to be initiated into the world of anal play and I would not suggest it for anyone! Lets fast-forward to the present. I got a job at a brick and mortar sex toy shop and while learning about the various products we sold I decided to expand my own knowledge about the industry. That is how this blog was born. I contacted a ton of small mom and pop type sex toy manufacturers and asked for an opportunity to review a product. One of the very first responses I received was an offer for a silicone dog tail anal plug (review coming soon). This is when I began to reevaluate my stance on anal play. I talked it over for a long time with my husband and decided to go for it. When I received this anal plug I was intimidated by its size. It was obviously too big for a beginner and terrifying for someone with my past experience. Once again my husband and I had a long talk about exploring this area and I contacted the manufacturer with my concerns. He graciously allowed me some extra time to review his product (I guarantee product reviews in a specific amount of time) and gave me some pointers for re-introducing anal play into my life. We decided to purchase some training plugs (review also coming soon) and some Anal Eaze to help prepare me for my review assignment.

Well, obviously I masturbate (so do you, or you wouldn't be here ;) ) and so I decided that the best way for me to get comfortable with my ass being invaded was to begin by myself. I grabbed my tube of Anal Eeze, smeared a generous amount onto my hole and searched my favorite erotica website for some double penetration stories. As my arousal mounted I reached for a vibrator and began to tease my clit and pussy. Soon I was stroking my g-spot, building up for an orgasm, and I decided to give my smallest training plug a try. I doused the plug with silicone lubricant while still manipulating the vibrator in my pussy. Gently I caressed my now slightly numbed hole with the tip of the plug. I tensed and held my breath as I prepared to penetrate my ass, then realizing how ridiculous I was being, I took a deep breath and relaxed. Slowly the tip entered my most forbidden of holes. As I worked the tip of the plug in and out, sinking it slightly deeper each time, I began to enjoy the sensations. It didn't take long before I was able to fully insert the plug creating a feeling of fullness that I have never experienced before. With the plug fully seated in my ass I was able to return my attention to stroking my g-spot to orgasm. I quickly realized that having the plug in my ass put enough pressure onto the vibrator for me to almost immediately cum. Not just cum, but squirt! The force of my orgasm pushed the plug from its position and I was speechless. This is what I have been missing? How different could my past sexual experiences been had I known how much I would enjoy the utter fullness of dual penetration.

Anal play has long been a forbidden and taboo act. Honestly, much of the thrill in anal play has to do with its forbidden nature. I had a mindset so ingrained into me from one bad experience that I could have easily never known the amazing feeling of being stretched to my limit while my husband nestles his hard cock into my ass and fucks my pussy with a dildo. I was so centered in on the "dirty" aspect of anal play and wouldn't even entertain conversation on the topic. Now I can comfortably initiate anal play with my husband without feeling ashamed or like I am doing something wrong. I guess I feel in some ways that by allowing myself to explore something that I had previously had such an aversion to I am taking control of my own sexuality. Unexpectedly, I enjoyed anal penetration and that has allowed me to consider exploring other avenues of expressing my sexuality that I may have never before considered. I am able to fully expand my horizons and test my own personal limits. I am excited to figure out what else we can add to our sexual relationship and I invite you to join me on this journey.

Lustfully yours,
xo Chastity Darling ox


  1. I love how this Diary entry ended. What a fucking asshole that Tim. I am sure if he would have talked to you, you would have consented to anal sex. That its something to need to work into not all of a sudden jump into with no warning or lube. But as I said before it ended well for you and your butt ;)

    1. Wasn't he, though?? Thanks for your comment and for reading.

  2. It's always awesome to hear about people (eventually) having good experiences with anal play! I'm really glad it ended up working out for you :)
    And I was a little amused reading this, because my current partner and the only person yet who has taken the time to let me ENJOY anal sex is named Tim and wears big baggy goth pants :P haha!


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