My First Anal Massage
I had been curious about anal play and anal massage for a long time, but the idea of exploring it was deeply uncomfortable for me. I could never bring myself to bring it up with my boyfriend, because I was so worried about what he would think about me. Would he think I was dirty? Would he think I was a freak? Would he be disgusted by that part of me? Was I disgusted by that part of me?
There were so many things that made me uncomfortable about the situation that I just consistently avoided it. Until I got several years into my relationship and realized that it would feel super awkward to admit I had been curious about this all this time, but too afraid, and too distrusting, to voice it.
The whole situation just felt kind of hopeless and icky to me. I wanted to explore it, but it felt so impossible to approach. I wasn’t even comfortable exploring there myself – the angle was awkward and I didn’t know what I was doing, and frankly I only had vague ideas about how to stimulate myself back there. I had some awareness that I occasionally found things pleasurable back there, but I really didn’t know what, exactly. And it was hard for me to relax while stimulating myself.
I felt weird for even being curious about it. And that wasn’t all I was curious about. Deep down, I had quite a fascination with anal penetration. I wanted to know what anal sex felt like.
Curious about experiencing anal massage?
When I discovered yoni massage, what secretly thrilled me most about it was the fact that the massage did not have to focus solely on the yoni, but could also include anal stimulation if that was my desire. The idea of receiving anal massage from someone who was actually a trained professional in the art of giving pleasure was extremely erotic to me.
At first, the idea of allowing, essentially, a complete stranger to touch me back there seemed crazy. I wasn’t even comfortable allowing my boyfriend to touch me back there – how could I possibly be comfortable allowing a stranger to do it?? But the truth was, there was a bit of a sense of safety provided in the idea of this pleasure service being a professional offering. It just didn’t have the same emotional vulnerability to it that the situation had with my boyfriend – I actually didn’t have to worry if he would still like me if I wanted to be touched there – I didn’t have to worry about him liking me at all! He was just doing his job and providing a service for me. That made it easier to think about relaxing and trying to enjoy it.
I decided to contact a yoni massage practitioner and set up the appointment. He sounded nice over the phone, and didn’t seem creepy. I felt like I could be brave enough to at least go meet him and see if I could be comfortable receiving pleasure from him.
On the day that I arrived for the appointment, I was nervous, but I was also excited. I had told him over the phone what I was interested in receiving, but we still sat down and talked beforehand about what I looked forward to receiving, how I wanted to be touched and where, and he also asked if there was anywhere I did not want to be touched. I told him all my preferences, as I had gone through his list and decided how I felt about each experience beforehand, so I knew what to tell him I did and didn’t want.
He had me get undressed and lay face down on a massage table. He started to massage my back, neck and shoulders, and down into my hips. Then he did something surprising and moved to massage my scalp and play with my hair. I relaxed fully enjoying the pleasure of his touch, and then he began to slide his hands down the center of my back and up along the sides of my waist and along the sides of my breasts.
I started to feel a strong tingle down between my legs. He teased the sides of my breasts and moved down to massage my hips and my upper legs. He moved my legs apart, pulling my feet to each side of the table, exposing my pussy and my anus – I could feel the air down there, and I was very aware that he could see everything.
He began slowly teasing the area around my anus – stroking the skin on either side of my butt crack, dipping his hands down to stroke my labia or tickle my clit. I felt my pussy get wet, and begin to drip. My clit tingled like crazy and the skin around my butt felt so sensitive.
My body twitched and I groaned with pleasure. He circled closer and closer to my anus, moving very slowly, and squirting plenty of lube all over me so nothing would get stuck as he touched. He slowly and intentionally probed the outside ring of my anus, putting extremely gentle pressure and moving so slowly.
I moaned with pleasure and could not believe how much I was enjoying this slow and deliberate touch. He would stroke the backs of my thighs or the sides of my waist occasionally as he slowly fingered my anus. His finger was only about a millimeter deep in my anus, and my body rippled with pleasure.
He continued to slowly deepen his touch, millimeter by millimeter, slowly and steadily giving my body pleasure spasms. He would occasionally reach down with his other hand and play with my clit or my vaginal opening for a moment.
My body felt electrified with pleasure – I could not believe how much stimulation I was enjoying from such a simple form of touch! He was moving so slowly and gently, but my body was absolutely rippling with pleasure.
As he continued his gentle attentions, my body pulled his finger deeper and deeper into my anus, and I began to rock my hips, wanting to simulate the feeling of being penetrated, of being fucked. I was deep inside my own mind, totally present in my body and just allowing and enjoying all of the intense sensations that flooded through my system.
As the feeling became more and more intense, he began to play with my clit with more intensity, matching my rocking hips with a slight thrust of his finger into my anus. With his other hand he put a finger into my pussy, and kept playing with my slick wet clit.
With all of the stimulation at once, between my anus, my pussy and my clit, my body began to flood with such intense waves of pleasure, I couldn’t help but radiate with orgasmic pleasure. The orgasm started in my anus then traveled to my pussy and flowed through my whole body. It was the most delicious feeling I had experienced thus far, sexually.
I experienced such a feeling of peace and calm after having such an intense orgasm. I felt so much stress release from my body, and I felt my body thank me for having explored a curiosity that had been so long felt. I felt blissful, and my body kept having little orgasmic aftershocks.
I kept going back to see the yoni massage practitioner and deepened in my anal experience and capacity to play. I had been desiring to experience anal penetration for so long, it was such a relief when the yoni massage therapist finally penetrated and fucked me with a toy that simulated a dick. I loved the feeling of being fucked that way, and it relaxed me in such a deeply profound way – unlike anything else I have yet to discover!
I love the way the yoni massage therapist slowly teases and builds the pleasure in my body, adding variety and spice to what he does so that I can never quite predict how he is going to stimulate me. And the power of the orgasms I have had have steadily increased, as I am able to relax and receive the pleasure more and more deeply.
Next, I hope to build towards experiencing double penetration. I have always been curious about how it would feel to be penetrated in both my anus and my pussy at the same time. It seems like it will be stimulation overload, and that excites me at a very deep level.
I’m so excited that yoni massage exists and that there is a space where I can explore these desires and curiosities without shame, where I can simply experience what I desire and learn where my pleasure edges lie. I can’t wait for my double penetration appointment! I expect I will have a very intense orgasm since I have gotten so much better at relaxing into the experience and going with the flo