How I Achieved the Best Orgasm of My Life.
By: Gem Hemingway
Tags: Sex, Relationships, Trust

Photo by Charles Deluvio on Unsplash

I recall a conversation that I had with my now partner on one of our first dates. While discussing sexual boundaries, I swore against backdoor entry and was disgusted by the thought of it…

I was recently out of a seven-year, very emotionally abusive, controlling, and may I say boring relationship with a narcissistic sociopath. I left that relationship crippled with trust issues and insecurities that I’m still fighting to this day. However, that is a story for another day. To say our sex life was lifeless should not come as a surprise. I had not had crazy sexual experiences nor may adventurous life experiences by the age of 30. I’m very much an “up for anything” type person. Still, my ex-husband seemed to put a damper on anything labeled fun and exciting.

About six months after moving out on my own, I meet lovingly coined “Dr. Guy”…

Dr. Guy was the most accomplished, adventurous, charismatic (and humble) person I had ever met, and he still holds that title to this day. Over a year later, I could go on and on with admiration about how incredible a human he is, but I won’t because this story is about sex, and that is why you’re still reading.

So back to the sexual boundaries discussion. I told him that I was pretty much “up for anything” except anal. Truth be told, I did think it was gross, and I was honestly terrified of the idea of anything entering that area. Of course, Dr. Guy respected my wishes and only brought it up in a joking way as time went on. We explored each other and new things, most of which made me blush, but we learned to trust each other in the process. I began to realize that I loved trying new things, and as the trust with my partner deepened, the easier it was for me to let go of my sexual boundaries.

NYE 2020 we were drinking at his place…like drinking a lot. I don’t rememeber a ton from the night’s conversations, but what I do recall is mid-fuck asking him if he wanted to “do anal”. He, of course, was down to clown. The first time was, as probably most anal rookies, pretty straight forward if you will. I remember that it wasn’t as bad as I thought it would be and I could see the potential for pleasure…

Months down the line and countless orgasms later, we found ourselves again drunk, mid-fuck, and freaky as ever. I went from being timid and shy to telling him what I wanted without hesitation. This time, I asked him if he wanted to “put it in my ass” while I use my toy (Enrique), which is a clitoral sucking, g-spot vibrator he gifted me (link in bio…jk). Again, down to clown. He just finished going down on me, so I was extra primed and ready to go. After getting Enrique into position, he lubed up. While laying on my side with him behind me, I gently pushed back until he was (mostly) inside. I turned on the vibrator, which has different settings, and we began to move slowly together. I remember saying, “I’m going to cum so hard,” shortly after we started. Then, I almost blacked out with pleasure. My eyes rolled into the back of my skull, and I screamed through the most intense orgasm of my entire life. It felt like it lasted forever, and I didn’t want it to stop. Once I came down from what must have been heaven, we started moving together again until the second orgasm came more intense than before. I was out of breath and starry-eyed.

The moral of the story is never say never. While I can sit here and say, get this vibrator and use it during anal and you’ll achieve the best orgasm ever, I believe it was only amplified by the trust and ease I have with Dr. Guy. So, I’ll sit here and say, create a space of sexual intimacy without boundaries with a partner you trust. It doesn’t happen overnight, but when everything clicks…