u/TheSam30

Sharing my first sissy experience. I travel for work and live out my sissy side back in the hotel room. I usually just dress in the room but today I wanted more. I downloaded Grindr and started to chat with guys. The usual flakes and weirdos, it was around 11:00 at night and was about to give up. The Hilton I stayed at stopped public access at this time as well.

Then a new profile popped up that was 1 foot away then pinged me with the usual "Hey". We started chatting to find out we're in the same hotel just 3 floors above me. My heart is racing now. Talked more and ask for pictures. I packed a few outfits, panties, etc. Then he sent a pic of his cock, 7" clean, cut, trimmed, white.

Since I was planning this and wanted to be discreet I went to Walmart earlier in the week to get supplies for a DIY gloryhole. A shower rod and a dark curtain. My room had the perfect entrance where I was able to set it up. Then I cut a slit waist height and height for me to be on my knees. The lighting was perfect to where I could leave the bathroom vanity light on and everything else dark. I could see him but couldn't see me. I sent him a pic of my setup and outlined what I wanted and rules. He immediately asked what room number.

Told him I had to get dressed and setup my room. I slipped on some lingerie and a teddy. Put the gloryhole up and setup the room. Just the vanity light on, I went to the other side of the curtain and placed a towel down to kneel on. I was so freaking nervous and excited. I sent him my room number and within minutes I hear a light knock on my door. I unlocked the door with my app and he opened the door. I see him walk in and head towards the curtain. Undid his shorts and there it was a semi hard cock I make out through the curtain and hole. He slipped through the hole and as I good sissy I began to kiss and lick. He got harder and it was bigger than I thought.

It was now or never as I wrapped my lips and mouth around his head. He let out a moan of satisfaction making me feel better. I didn't know what to expect since it was my first time. It was softer than I expected at first. I twirled my tongue around his head. The taste was neutral, slight salt taste from his tip. I took in more in my more mouth as he continued to moan. I felt his cock getting harder and longer. To a point where I had to watch my teeth, I started to bob and he began to thrust hitting the back of my throat I gagged which he liked. Then felt the curtain brush open as he reached around to grab the back of my head which I didn't plan for but didn't fight. He thrusted harder and faster. Me trying my best not to gag or close my teeth.

I felt him start to tense then it happened, I felt his veins get hard against my lips and the hit cum start to pump. It hit the back my throat forcing me to swallow as he head the back of my head. After he finally finished cumming he let go of my head and pulled out of my mouth and though the hole. Pulled up his shorts and left. I'm still on my knees in the dark covered in spit. I eventually got up and cleaned up and proceeded to finish myself off. It was amazing

Sharing my first sissy experience. I travel for work and live out my sissy side back in the hotel room. I usually just dress in the room but today I wanted more. I downloaded Grindr and started to chat with guys. The usual flakes and weirdos, it was around 11:00 at night and was about to give up. The Hilton I stayed at stopped public access at this time as well.

Then a new profile popped up that was 1 foot away then pinged me with the usual "Hey". We started chatting to find out we're in the same hotel just 3 floors above me. My heart is racing now. Talked more and ask for pictures. I packed a few outfits, panties, etc. Then he sent a pic of his cock, 7" clean, cut, trimmed, white.

Since I was planning this and wanted to be discreet I went to Walmart earlier in the week to get supplies for a DIY gloryhole. A shower rod and a dark curtain. My room had the perfect entrance where I was able to set it up. Then I cut a slit waist height and height for me to be on my knees. The lighting was perfect to where I could leave the bathroom vanity light on and everything else dark. I could see him but couldn't see me. I sent him a pic of my setup and outlined what I wanted and rules. He immediately asked what room number.

Told him I had to get dressed and setup my room. I slipped on some lingerie and a teddy. Put the gloryhole up and setup the room. Just the vanity light on, I went to the other side of the curtain and placed a towel down to kneel on. I was so freaking nervous and excited. I sent him my room number and within minutes I hear a light knock on my door. I unlocked the door with my app and he opened the door. I see him walk in and head towards the curtain. Undid his shorts and there it was a semi hard cock I make out through the curtain and hole. He slipped through the hole and as I good sissy I began to kiss and lick. He got harder and it was bigger than I thought.

It was now or never as I wrapped my lips and mouth around his head. He let out a moan of satisfaction making me feel better. I didn't know what to expect since it was my first time. It was softer than I expected at first. I twirled my tongue around his head. The taste was neutral, slight salt taste from his tip. I took in more in my more mouth as he continued to moan. I felt his cock getting harder and longer. To a point where I had to watch my teeth, I started to bob and he began to thrust hitting the back of my throat I gagged which he liked. Then felt the curtain brush open as he reached around to grab the back of my head which I didn't plan for but didn't fight. He thrusted harder and faster. Me trying my best not to gag or close my teeth.

I felt him start to tense then it happened, I felt his veins get hard against my lips and the hit cum start to pump. It hit the back my throat forcing me to swallow as he head the back of my head. After he finally finished cumming he let go of my head and pulled out of my mouth and though the hole. Pulled up his shorts and left. I'm still on my knees in the dark covered in spit. I eventually got up and cleaned up and proceeded to finish myself off. It was amazing.

Love to hear your hotel experiences!

Sharing my first sissy experience. I travel for work and live out my sissy side back in the hotel room. I usually just dress in the room but today I wanted more. I downloaded Grindr and started to chat with guys. The usual flakes and weirdos, it was around 11:00 at night and was about to give up. The Hilton I stayed at stopped public access at this time as well.

Then a new profile popped up that was 1 foot away then pinged me with the usual "Hey". We started chatting to find out we're in the same hotel just 3 floors above me. My heart is racing now. Talked more and ask for pictures. I packed a few outfits, panties, etc. Then he sent a pic of his cock, 7" clean, cut, trimmed, white.

Since I was planning this and wanted to be discreet I went to Walmart earlier in the week to get supplies for a DIY gloryhole. A shower rod and a dark curtain. My room had the perfect entrance where I was able to set it up. Then I cut a slit waist height and height for me to be on my knees. The lighting was perfect to where I could leave the bathroom vanity light on and everything else dark. I could see him but couldn't see me. I sent him a pic of my setup and outlined what I wanted and rules. He immediately asked what room number.

Told him I had to get dressed and setup my room. I slipped on some lingerie and a teddy. Put the gloryhole up and setup the room. Just the vanity light on, I went to the other side of the curtain and placed a towel down to kneel on. I was so freaking nervous and excited. I sent him my room number and within minutes I hear a light knock on my door. I unlocked the door with my app and he opened the door. I see him walk in and head towards the curtain. Undid his shorts and there it was a semi hard cock I make out through the curtain and hole. He slipped through the hole and as I good sissy I began to kiss and lick. He got harder and it was bigger than I thought.

It was now or never as I wrapped my lips and mouth around his head. He let out a moan of satisfaction making me feel better. I didn't know what to expect since it was my first time. It was softer than I expected at first. I twirled my tongue around his head. The taste was neutral, slight salt taste from his tip. I took in more in my more mouth as he continued to moan. I felt his cock getting harder and longer. To a point where I had to watch my teeth, I started to bob and he began to thrust hitting the back of my throat I gagged which he liked. Then felt the curtain brush open as he reached around to grab the back of my head which I didn't plan for but didn't fight. He thrusted harder and faster. Me trying my best not to gag or close my teeth.

I felt him start to tense then it happened, I felt his veins get hard against my lips and the hit cum start to pump. It hit the back my throat forcing me to swallow as he head the back of my head. After he finally finished cumming he let go of my head and pulled out of my mouth and though the hole. Pulled up his shorts and left. I'm still on my knees in the dark covered in spit. I eventually got up and cleaned up and proceeded to finish myself off. It was amazing.

Love to hear some of your experiences!

Sharing my first sissy experience. I travel for work and live out my sissy side back in the hotel room. I usually just dress in the room but today I wanted more. I downloaded Grindr and started to chat with guys. The usual flakes and weirdos, it was around 11:00 at night and was about to give up. The Hilton I stayed at stopped public access at this time as well.

Then a new profile popped up that was 1 foot away then pinged me with the usual "Hey". We started chatting to find out we're in the same hotel just 3 floors above me. My heart is racing now. Talked more and ask for pictures. I packed a few outfits, panties, etc. Then he sent a pic of his cock, 7" clean, cut, trimmed, white.

Since I was planning this and wanted to be discreet I went to Walmart earlier in the week to get supplies for a DIY gloryhole. A shower rod and a dark curtain. My room had the perfect entrance where I was able to set it up. Then I cut a slit waist height and height for me to be on my knees. The lighting was perfect to where I could leave the bathroom vanity light on and everything else dark. I could see him but couldn't see me. I sent him a pic of my setup and outlined what I wanted and rules. He immediately asked what room number.

Told him I had to get dressed and setup my room. I slipped on some lingerie and a teddy. Put the gloryhole up and setup the room. Just the vanity light on, I went to the other side of the curtain and placed a towel down to kneel on. I was so freaking nervous and excited. I sent him my room number and within minutes I hear a light knock on my door. I unlocked the door with my app and he opened the door. I see him walk in and head towards the curtain. Undid his shorts and there it was a semi hard cock I make out through the curtain and hole. He slipped through the hole and as I good sissy I began to kiss and lick. He got harder and it was bigger than I thought.

It was now or never as I wrapped my lips and mouth around his head. He let out a moan of satisfaction making me feel better. I didn't know what to expect since it was my first time. It was softer than I expected at first. I twirled my tongue around his head. The taste was neutral, slight salt taste from his tip. I took in more in my more mouth as he continued to moan. I felt his cock getting harder and longer. To a point where I had to watch my teeth, I started to bob and he began to thrust hitting the back of my throat I gagged which he liked. Then felt the curtain brush open as he reached around to grab the back of my head which I didn't plan for but didn't fight. He thrusted harder and faster. Me trying my best not to gag or close my teeth.

I felt him start to tense then it happened, I felt his veins get hard against my lips and the hit cum start to pump. It hit the back my throat forcing me to swallow as he head the back of my head. After he finally finished cumming he let go of my head and pulled out of my mouth and though the hole. Pulled up his shorts and left. I'm still on my knees in the dark covered in spit. I eventually got up and cleaned up and proceeded to finish myself off. It was amazing