“Perfectly easy anal sex” is an awesome success story from one of my followers on FetLife. The experience and issues that faced this person is echoed by so many that I asked if I could publish our dialogue for the benefit of others. This person’s story actually started with a post entitled “So I really wanted to try anal” about 8 months before she came to me for help. Here is how we started:

” I have gotten ok with the insertion and toys being in there…but the fucking motion…i don’t like it. It causes me pain. Currently I have called an all stop to anal until I figure it out.”

Based on a lot more detailed information that was shared, I directed her to a number of the articles that I have now published here and gave her a couple of specific pointers. 3 months later she wrote back to me;

“I wanted to say thank you for your help and support and advice.

So yesterday afternoon kinda out of the blue, didn’t really plan to, we just kinda went for it…. I had anal for the first time and it was awesome. We didn’t do any prep stretching or anything but because of what I’d been doing on my own it didn’t hurt at all….and he is not even a small guy…lol. and I had the most amazing orgasm from it….lol

Can’t wait to try it again! Yay!

Thank you again. :)”

So pleased with her success she wrote this account of her experience for me. She was happy for me to publish it on for others, especially those who might find a site like FetLife a too confronting to even visit.

At the same time the idea of trying anal kinda squidged me out a bit ….for a couple of reasons.

One, well it’s anal and you hear all kinds of horror stories about how it hurts, and well there’s the poop factor. Also for me I had gotten a little additionally freaked out because I had a bit of a bad experience with a guy who, using just toys, had pushed me a little too far and had caused a good bit of pain and discomfort, some from the stretching but mostly from the thrusting. So I had completely freaked out about anal, and pretty much closed the doors back there for a while.

But I was not deterred. (If you’ve read my profile you know that I can be rather stubborn) I still wanted to get to the point to try anal, why I honestly have no idea, but I did. Maybe I would hate it and never do it again, maybe I’d love it and become an “anal whore.” Either way I wanted to at least try it and see which way my ass went.

Anal 101. I read a bunch of people’s comments and questions and the good advice that people had posted in response. Then being too embarrassed to post my own question on the group I instead messaged someone who had been giving that good advice and told him what had happened and asked him some questions about how I should move forward to –GASP- train myself…

He gave me some really good advice about making it about me, and what felt good to me, and stopping if it didn’t feel good. Which all seem pretty logical, but when it comes to anal, I had gotten all sorts of turned around so I needed that logical advice. He also gave me some pointers on how to go about the first time when I was finally ready for anal.

So that’s what I did. When I masturbated I used butt plugs. Small at first and then slowly worked my way to bigger. Sometimes I would just put them in there and them…ummm concentrate on other things…sometimes I would use my “anal dildo” (it’s long, flexible, thin and has a handle) and move it in and out to get used to the thrusting motion. It all depended on what felt good that day. It got to a point that some days I craved the anal stimulation while I masturbated.

This lasted several months. And over that time I had several guys that I was talking to ask if I was into anal, and I would tell them not yet. Initially I told a couple guys that I was working on it, and was training myself for it. And OMG, the reactions I got from that…

“That’s weird.”

“You can’t train yourself”

“It would work better if I trained you”

So I stopped telling guys that I was training myself and just told them I wasn’t up to anal yet.

So, when I did have anal for the first time I had a plan, based on my reading and the advice I had gotten.

• I was going to be in control…would probably be on top as the squatting position is the supposed to be the easiest.
• Would use toys or fingers first to loosen things up a bit.
• Would do an enema before to get rid of that worry.
• Would use lots and lots of lube.

Yeh…so not a single one of those happened…lol

I was meeting a newish fwb for a little afternoon delight. As I was getting ready to drive over I decided to be a little daring and take my vibrating butt plug, so maybe if he was willing he could fuck me with it in my ass, which I’ve been wanting to try.

So I arrive and we starting kissing and clothes are removed, not that he was wearing much when I got there, just black boxer briefs, my favorite. I tell him about the toys I brought and he seems perfectly willing, so I think YAY!

He pushes me down on the bed and crawls on top of me, pinching and nibbling on my breasts. Then he slides down between my legs and drives me crazy with his mouth and hands for a while, until I came.

He stood up and moved to the side of the bed, and I nearly attacked his cock with my mouth. I was on my hands and knees on the bed in front of him sucking and licking and them I felt the vibrator moving along the seam of my ass. He pushed it in slightly, but for whatever reason, my position, the angle; it wouldn’t go in so he set it aside.

I was a little disappointed, but I figured, oh well, no big deal.

I pulled my mouth back to the tip of his cock and looked up at him and he asked if I wanted his cock inside me, and I said yes. He tossed me back on the bed again, crawled between my legs and impaled himself in my wet pussy. It felt great. He fucked me deep and hard, and then slow and shallow and the fast and then deep again. He was driving me crazy.

Then still kneeling between my legs he pulled out and rubbed his cock on my asshole. I met his eyes and he raises his eyebrow at me and asks me if I want more.

At that moment, I wasn’t scared or worried or anything. And I trusted him. I knew he would stop if I didn’t like it and not be mad or upset about it. That he really did care about my pleasure. And at that moment All I wanted was for him to put his cock in my ass. So I followed my instincts and I said yes.

He pushed his cock in real slow, just to the point where it would stretch and should hurt, but it didn’t, not even slightly, it felt amazing.

He stopped and looked at me again and asked if I wanted more, and I am pretty sure my yes was in the form of a moan that time. So he slowly slid his cock all the way in, and still no pain, just this wonderful feeling.

Then he started to move and I felt the orgasm coming almost immediately.

He asked me if he could come in my ass and I said yes, partly because I didn’t care if he did and partly because I was so not letting him pull out until I had cum. And then I did, at the same time that he did incidentally, and O.M.G….. it was the most amazing orgasm I have ever had!!

So I am pretty sure the reason it went so well is because I trusted him and I had become comfortable with my own ass and its pleasure.

I think if I had followed my original plan it would have gone ok, but I think I would have been too focused on it and nervous about it, and I don’t think I would have had the earth shattering orgasm I had, so I am glad I followed my instincts and went for it, and that my self training made me ready for it.