Categories: Other Sex Stories

First Time Sissy At The Gloryhole

First Time Sissy At The Gloryhole

It was Saturday night and I was out with some of my friends. They had been talking about this new place that had opened up called the Gloryhole and I was curious to see what it was all about. We decided to check it out and when we arrived, I immediately noticed the large sign that said “No Sissies Allowed”. I was a bit taken aback by this, as I was a sissy and I wasn’t sure if I’d be allowed in or not.

But my friends were already going inside and I didn’t want to be left out so I followed them. Luckily, the door guy let me in and I found myself in a large room filled with people of all different kinds. There were a few couples making out in the corner, some people playing pool, others dancing, and then there was the glory hole.

I had heard about glory holes before, but this was the first time I had seen one in person. It was an oval-shaped hole in the wall with a thick curtain around it. I watched as a few people went up to it, put their hands through the curtain and then started getting serviced by someone on the other side. I was intrigued, but also a bit scared. I had no idea what to expect, but my curiosity got the best of me.

I walked up to the hole, put my hands through the curtain, and waited. Before I knew it, I felt a pair of warm lips on mine. The person on the other side was kissing me passionately and I felt my heart racing. I closed my eyes and let the sensations wash over me. The person was licking and sucking my ears, neck, and lips, and I felt myself getting aroused.

The person continued to kiss me and I could feel their hands exploring my body. I felt my nipples harden as they were being pinched and rubbed. I was surprised by how much pleasure I was getting from this and I started to moan softly.

The person then moved his hands down to my crotch and I felt a warm wet tongue licking my clit. I gasped as the sensations coursed through my body and I felt myself getting even more aroused. The person started to finger me and I could feel a finger entering my ass. I felt embarrassed at first, but I couldn’t deny the pleasure it was bringing me.

The person continued to lick and finger me until I finally came. Afterward, I felt a sense of relief and satisfaction. I had just had my first experience with a glory hole and I was amazed at how good it had felt. I thanked the person on the other side and then went back to my friends.

I was still in shock from my experience at the glory hole and I couldn’t stop thinking about it. I was no longer scared of the idea of being a sissy and I realized that this was something I wanted to explore more. I started researching the glory hole and all the different types of services they offered.

I found out that there were different types of glory holes, such as the blowjob glory hole and the anal glory hole. I decided that I wanted to try out both and so I made an appointment with an escort service.

The escort arrived at my place and I felt a bit nervous, but I was also excited. He took me to a hotel room and I was amazed at the setup. There was a glory hole in the wall, with a curtain around it, and a bed in the middle of the room.

The escort told me to get undressed and I did as he asked. He then went behind the curtain and I heard him start to pleasure himself. I slowly put my hands through the curtain and felt a warm mouth start to suck my fingers and lick my palms. I felt my body start to respond to the sensation and I closed my eyes and enjoyed it.

The escort then started giving me a blowjob and I was in ecstasy. His mouth felt amazing on my cock and I couldn’t believe how good it felt. I was soon on the brink of orgasm and I felt my body trembling. After a few minutes, I finally came and felt a sense of relief wash over me.

The escort then invited me to the bed to try out the anal glory hole. I felt a bit nervous, but I decided to go for it. I put my hands through the curtain and felt a warm tongue licking my ass. I felt my body start to respond to the sensation and I closed my eyes and enjoyed it.

The escort then started to penetrate me and I felt a surge of pleasure course through my body. He kept thrusting deeper and deeper until I felt him bottom out inside me. I was in ecstasy and I felt my body trembling as I reached my climax.

When it was all over, I felt a sense of accomplishment wash over me. I had just experienced my first time at the glory hole and it had been amazing. I thanked the escort and then went back home feeling satisfied and empowered.

I had finally taken the plunge and explored my sissy side. I had gone to the glory hole and it had changed my life. I now had a newfound confidence in myself and I knew that I could do anything I set my mind to. I was no longer scared of exploring my sexuality, and I was ready to take on the world.

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