My Search for Erotic Videos About Anal Training

I had recently told my boyfriend that I was interested in incorporating anal play in our sex life. I had been sitting on the fact that I was curious about anal training for a long time, and I finally gathered up the courage to tell him that I was into such a taboo kink. I had no idea how he would react, because our sex life up until that point had been pretty vanilla, and I had been afraid to push the envelope around what we were getting into together. I was especially interested in anal training.

The truth was, I had always been interested in trying anal play, and getting into anal training, but I hadn’t been with a man until this point in my life whom I actually trusted enough to play with me back there. My current boyfriend was different. He clearly actually cared about whether or not he was providing me with pleasure. He was super attentive when he touched me, and he never had to ask me if I was enjoying something, because he could just tell from my response. It was so sexy to experience attention of that quality.

For the first time in my life, I actually felt like I had the kind of safety with someone that I needed in order to really bloom into my sexuality. I could feel parts of myself opening and getting curious, and I was feeling far more comfortable in my skin. He made me feel like I was incredibly sexy, as long as I was in my pleasure. What more could I ask for?

I was pleasantly surprised that my boyfriend was enthusiastic about the idea of anal training. He let me know that, he hadn’t wanted to intimidate me, but he absolutely loves anal play, both giving and receiving. He was particularly interested in anal training with me – he loved the idea of slowly training my ass to potentially accommodate his cock. I hadn’t quite gotten to the point of wanting to try anal sex, but I figured that some anal training was a good place to start.

Once I knew he was on board, I took to the net to see what I could find as far as education on anal training. I found a video series in my search called “The Best She Ever Had,” which apparently had a couple videos that were specific to anal training.

In addition to the videos that were focused on anal, there were also videos about erotic pussy massage, clit massage, g-spot massage, breast massage, as well as videos on intercourse techniques. There was a lot of content for us to explore, and it seemed like a good choice to dive into learning about these things.

My boyfriend and I set up a date to watch the anal training video together. He asked me if I wanted to watch it with him and follow along, and I thought that sounded like an exciting idea. We procured a small butt plug and anal toy to bring to our pleasure session, and we got ready to watch the video.

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We put the video on in our bedroom, and I laid down naked on our bed on my front. My boyfriend settled himself next to me and we watched the beginning. To start with, the instructor talked about how important it was to encourage a woman to fully relax in order for her pelvic nerve to activate, so that her entire body could become a pleasure receptor.

I relaxed on the bed, and my boyfriend started to run his hands all over my body, from the bottoms of my feet, up my back and down my arms. He knew I loved having my hair played with, so he sat and ran his fingers through my hair for a while. My breathing deepened, and my body started to feel deliciously relaxed. I could feel myself sinking into the bed. Then, just as I was fully relaxing, my boyfriend excited me by dragging his finger tips through my butt crack, teasing the sensitive skin in that area, and lightly circling his finger around my anus.

My body convulsed with each little touch, and then he went back to rubbing my back and my hips. He would occasionally dip his fingers into my sensitive places, and then back to the regular massage. The instructor in the video was talking about the importance of mixing things up, and keeping things unpredictable so that the excitement would be heightened for a woman. With a woman in such a relaxed state, this kind of teasing increases her pleasure immensely. I can tell you I was experiencing this for myself first hand.

When my body was fully on fire with the amount of pleasure that his teasing was building in my body, he settled himself down by my hips, and started to tease around my buttcrack, and playing with the wrinkles around my butthole. I shuddered as he squirted lube around my anus, slowly and gently rubbing it around with his finger.

The instructor on the video was talking about the importance of going incredibly slow when beginning anal training, because the muscles in the anus take time to relax, and they need to be relaxed in order to be receptive to pleasure and penetration. He also stressed the importance of hygiene and keeping items that are inserted in the anus separate from anything that touches my pussy.

My boyfriend played lightly around the outside of my anus, and I writhed a bit on the bed as he did so. I was very anxious for him to go ahead and explore my ass. He very slowly dipped his finger tip inside my ass, just a tiny bit at a time, allowing me to get used to the size of his finger. His slow and gentle movements sent little shocks of pleasure from my ass straight into my clit.

As he was very slowly fingering my ass, sinking his finger just a little bit deeper, a little bit at a time, he also would occasionally reach his hand between my legs and tickle my clit. I was starting to lose my mind a bit, because I was receiving so much stimulation at once. My body wanted to cum, but my boyfriend was not going to let me anytime soon.

Once he got his finger a couple inches into my ass, he felt around in little circles, finding the spots that gave me the most pleasure, and slowly loosening my muscles. When I was ready, he switched out his finger and began slowly inserting the lubed up anal toy. I was really, really enjoying this anal training.

When he had the toy fully inserted in my ass, he reached his hand down to grasp my clit through my labia, wiggling my hard little clit between his fingers like a gummy worm. He slowly and steadily pumped the toy in and out of my ass, small movements that sent pleasure shocks straight to my clit.

Before I could cum, he pulled out the anal toy and switched it out for the slightly bigger anal plug. I enjoyed the feeling of being more stretched out, as he still very slowly inserted this toy into me. He started to stroke my clit with little up and down movements, like he was jacking off a tiny penis. My body was so ready for an orgasm. I was writhing and squirming and rocking on the toy and his fingers, trying to get myself all the way there.

He was keeping me just on the edge, determined to stay in charge of the timing of my orgasm. He kept pumping with the plug, moving it in circular motions, hitting all the most sensitive places inside my ass. I was feeling absolutely explosive. I begged him to let me finally climax.

He settled into a pace where I could tell he meant business. His rhythm became steady, and he used a bit more pressure with his touch. He was clearly ready for me to cum, and I was so ready to oblige. I allowed myself to lose focus and just feel all of the different pleasure energies moving throughout my body. The pressure on my clit with his fingers drove me over the edge, and I moaned loudly through a powerful orgasm while he pumped the plug in my ass.

Following along with the video was sexy as hell, and I am hoping we will keep doing it in future pleasure sessions with the other videos. We learned so much about anal training. We’ve needed some new material for our sexy time, and I was completely thrilled with our first experience.