Sissies random encounter in a park

By Sissy Chanel

Published on Nov 11, 2023



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Disclaimer: This story is erotic fantasy. The characters and events described are fictional. Any likeness or similarity between persons, places, products or concepts are purely coincidental.

If you are under 18, and/or offended by descriptions of homosexual activity or live someplace where reading such material is prohibited, don't read this. The following story contains strong language and explicit scenes of male on male sex, and cross-dressing.

Please email me your comments to sissy chanel or Kandi, if you enjoyed reading, shot your load or can relate to the story in any way. It means a great deal to us to get feedback from our readers. I will respond to every one of them. My email address is, or (this was a collaboration. The story is from and edited by We'd both love to hear from you.

This story is the copyright property of the author and may not be copied, used or posted to any other websites without explicit permission from the author.

Chapter 1: How it all started

It was 1:30 am a few days after my 18th birthday. My parents had just left town to visit my older sister. I had just finished three wine coolers, and I was pretty buzzed, I didn't have a lot of experience drinking.

I had often dabbled in crossdressing. Mostly I wore panties when I could. I always loved how the silk felt against my small 5'4 body. My small frame and curly hair didn't help matters. A friend at school had joked that I was a sissy. He didn't know how that affected me (he still doesn't know.)

I went home and I thought to myself, "Damnit, I need to know! Am I a sissy faggot?" Needing to find out I decided to go to a park roughly three blocks from my house.

It was well known among the locals that sissies, gays and other guys would hook up there. The park had quite a few trees and a little stream area. I walked down to the park shaking because I was so nervous. I was also oddly excited. I had stolen my sister's small silky red and black thong panties with a cute red bow on the front. The thong was riding up my ass so hard. I couldn't contain my excitement and arousal in the small panties.

I had only been in the park for about two minutes when this straight-up daddy type walked right up to me. He was probably in his late fifties. If I had to guess he was about 5'7. He was a bigger guy, not fat, but he had a dad's body for days.

I loved the features of his round face, grey stubble beard, and his well-cared-for salt and pepper hair.

I made eye contact. I quickly averted my eyes hoping that he didn't notice. He noticed alright! He walked straight up to me and without saying a word simply grabbed my hand. His hands were rough yet gentle. I was in a complete haze as he led me behind some bushes a little ways off.

I started to mumble something about how I wasn't ready, I was scared, etc. However, he was already holding my hand. Like an alpha, he moved my hand and put it on his semi-hard cock through his mesh-type shorts. He said, "It's ok, I know what you need."

I was hypnotized. I thought to myself "holy shit this is happening!" I had no control like an out-of-body experience. Worse yet, I loved how that felt!

He moved my hand around on his still-growing cock through his shorts. He asked me "Is this what you want?"

I couldn't believe what I was doing. without thinking I simply moaned the word "yes."

He instructed me to "get on my knees and take out his cock." My little clitty was straining so hard against my silky panties. It was trying to tell me this was just so, right.

Without any more prompting, I slipped to my knees and undid his shorts. I gently tugged them down just a little. My mind still wasn't sure that I wanted to go through with this, but my body sure did. As I pulled his shorts down just a little bit his cock flopped out. It was semi-erect and right in my face. This older experienced man's cock was just right there in my face!

He told me exactly what he wanted and what he wanted to do. I was so lucky. He was in control and was not afraid to teach me.

He told me to slap his dick on my face. I couldn't resist even if I wanted to. As I was slapping his hot cock on my face I could feel his dick growing and getting hotter.

He had me use both hands. Being so small I have quite small hands. Jerking this hot dick off felt heavy in both hands. As I was doing this he had me use one hand to rub his balls. I could see him roll his head back and groan. I was so hot because I was making this grown man heavy with arousal. Without warning he grabbed the back of my head and pulled it forward. The next thing I knew his dick was in my mouth. Maybe this is bad to say but it just felt so easy and natural.

He was hot and talked dirty to me. The more dirty he talked the more aroused I got. I loved it when he called me "sissy slut" or "cum dump," He constantly repeated that I was a "good little cocksucker." Sometimes I would slow the pace so I could feel his heat and the veins on his dick. I paid attention to the details. I knew to lick right under the tip of his cock because I saw how much that made him jump when I did. Sometimes I did gag and it was a struggle. When that happened he would slow down and let me get my composure. As he was deep in my mouth I wanted to touch myself in my panties. I reached down and started to rub my clitty. When he saw this he slapped my hand and told me "NO!" He pulled his cock out of my mouth, grabbed my throat, and told me I was there to service him. Once he was done telling me "no" he simply slid his warm delicious cock right back into my mouth. He was firm with me as I worked up to trying to get my nose to his belly. Suddenly he grabbed the back of my head again. This time he used both hands.

He started to groan loudly this time he flooded my mouth. I was caught off guard and surprised that I backed up as he was still shooting his load. Most of it went down my throat and in my mouth but some also sprayed onto my face, hair, and clothes. It was so brutal, primal, and most of all amazing!

Without a word, he pulled up his shorts and slapped my ass. He didn't believe that it was my first time and simply walked off. As he walked off he said "once you make a man cum, you're forever a sissy."

He was so smart as to not let me cum. I think he knew if I did I would have regrets and "buyer's remorse."

I now know my friend was right, I am a sissy. Also, I just got turned into a little faggot sissy by a PRO!

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