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Jen's Anal Sex Experience

Posted by TooTimid Staff to Anal Sex

“So what did he tell you?” We sat around the table waiting for Susie’s reply.

“I need the three B’s,” she told us. She could see the look of confusion on each one of our faces. “Booze, Barry Manilow, and Backrub—the three B’s. He says that’s all I need.”

Susie was having a difficult time with anal sex and her fear of having it was causing her severe anxiety. She had gone to our on-campus doctor for advice. What he suggested, boiled down, was to simply relax.

Relax was what I didn’t do the first time my partner suggested anal sex. We weren’t even in the bedroom; he simply threw it out over burgers one afternoon. “What do ya think about anal?” Thank God he knew the Heimlich maneuver because I instantly began choking on my food.

I thought my near death experience would have thwarted any more anal conversations between us. How wrong I was. Two days later, while having sex, doggy style, I heard from over my shoulder, “You might like anal.” (I think he had it in his head that since I was already in position…) I had him flipped and pinned on the floor within three seconds. A head lock securely in position I gave him my warning, “You even THINK about coming near my ass with that,” I shook my finger violently at his now limp penis, “And I promise you’ll be singing in the boy’s choir before the day is through.”

Sure, it might have been a harsh reaction. I see that now; but then I just couldn’t see the reason for anything anal. Hey, I’m willing to try pretty much whatever else you got up your sleeve, but anal? Nope, just back away slowly.

It wasn’t until two years ago that I allowed a partner to even broach the idea without drop kicking him. I must have had my guard down; it’s the only explanation. It was during a heavy session of foreplay that I realized my partner’s hand was creeping towards my butt. My hormones had the better part of my brain at that moment so I didn’t try and stop him. He slowly began to finger and flick the outside of my anus and before I knew it I was in the middle of a full fledge, no-holds-barred orgasm.

The next night in bed I was coaxing his hand towards my backside before he even tried. I couldn’t believe the intense and mind-blowing orgasms that his anal play were producing! I was relaxed and enjoying this new experimentation, which my partner knew. “Do you want to try?” He asked. I knew what he meant and for the first time I felt comfortable replying, “Yes.” I loved it! I couldn’t believe I had been missing out on something as pleasurable as anal sex. I’ll admit, I’ll take vaginal penetration over anal more often than not, but I love knowing I have a choice.

The number one key to anal sex is to be relaxed and comfortable—literally. The anal muscles spasm when something foreign is placed inside the anus. The only way to avoid this is to relax. A good introduction to anal play is using a finger. Rubbing and stimulating the anal area with your finger will help you and your body relax. Gradually insert the finger in your anus, nothing to quick or jarring. The anus does not create lubrication like the vagina so it is extremely important to use lots of lubrication during any anal play. Keep in mind, oil-based lubricants can break down a latex condom, diminishing its effectiveness. Once you feel at ease using a finger you may want to try using a slender vibrator or dildo.

Anal intercourse is best experimented with once both partners feel comfortable. There are many sexual positions to chose from, with doggy style being one of the most popular. Personally I found lying on my side and fashioning my legs around my partner, in a scissor like fashion, to be the most comfortable way to enjoy anal sex. I was more relaxed and my body was more relaxed, allowing for easier and less painful penetration.

I know I worried about it and I am sure you worry about it too: the cleanliness factor. I’ll be honest, one of the reasons I feared anal sex so much was because of how a partner, in the past, had made me feel. He always made me feel unclean and dirty. He actually thought it was disgusting when I was so worked up that my wetness seeped onto his sheets. I can’t even begin to imagine how he would have reacted to anal sex. So here’s the scoop. Having a bowel movement and showering before anal sex will greatly reduce/eliminate messiness. It’s not to say that there couldn’t be something left in your rectum—which is always a possibility. For the most part though you have cleared the passage way for anal play (pun intended). You can chose to use an anal douche, but I never have and don’t plan on trying it.

So lets review. Jen used to hate/fear anal sex. Jen learned to relax. Jen began exploring anal play. Jen realized what she was missing. All I can say is relax and explore. And also be safe—use a condom!

Toys to get you started:
Beginner Anal Kit - 3 Sizes
Small Jelly Beginner Plug


Date 12/29/2014
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