Sissy Neighbor Stories

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Sarah was Caught Peeping

by SarahCD on Jan 14, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some...

Instructional Jerkoff Sissy

by dirtywordygirl on Aug 19, 2017
Exhibitionist & Voyeur

Right now, I just want you to lay back on the bed and show me what you have down there... No! I DIDN'T SAY YOU COULD TOUCH IT! That's very naughty of you to do that. First you have to ask me, so let go of your cock and show it to me like a bad little girl...you're a very bad little girl, aren't you? Let's get you a little wet and slippery, ok? Ask me if y...

Panty Jerkoff Encouragement

by dirtywordygirl on Sep 13, 2017
Exhibitionist & Voyeur

Right now, I just want you to lay back on the bed and show me what you have down there... No! I DIDN'T SAY YOU COULD TOUCH IT! That's very naughty of you to do that. First you have to ask me, so let go of your cock and show it to me like a bad little girl...you're a very bad little girl, aren't you? Let's get you a little wet and slippery, ok? Ask me if y...

Neighborly Relations Pt. 02

by grizzley123 on Jan 15, 2019
Fetish

NOTE: I always appreciate comments. You can read my slightly longer message on the first part of the story, but the gist is... I like my themes, you might like other ones. But I always enjoy comments, regardless of their content. **************** It helps to read part one where my neighbor starts to take control of me by using his incredibly hot step-daugh...

Jesse's Journey Down a Rabbit Hole Ch. 04

by sadkins116 on Sep 19, 2017
Illustrated

As I mentioned in the previous chapters, this story is a collaborative effort between me and Rebeccsm. She has provided the art, and a lot of the plot, god I love how her mind works, and me for the text. Please let us know how you feel about our efforts. Comments and votes are welcome. It is the only way we will know if you like our work. I would like to th...

The Neighbor Daddy Next Door

by ddogg44 on Jun 4, 2019
Transgender & Crossdressers

PART 2 (continuation of "college is a time to explore) Daniel awoke with the feeling of a lacy black thong riding up his ass. A raging hard on pulsed in rhythm to the sound of Text messages being received. It was the next day, and Daniel was due for a spanking by his next door neighbor "daddy" for getting some cum on the carpet. "Be here at noon, keep th...

Sarah was Humiliated

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I got myself into trouble the other day. I live on the second floor in a little apartment building. I was just starting up the stairs when I looked up and saw that my neighbors were out on the landing. She had her back to the railing and was talking to her boyfriend. She was wearing a short white cheerleaders skirt. I froze and stood there trying to look up...

Sissy Panty Handjob

by CrossdresserCaitlyn on Jun 19, 2018
Transsexuals & Crossdressers

When I woke up in the morning I saw my girlfriend getting ready for work. She sees me awake and reaches out and rubs my penis outside my panties. While rubbing me she tells me if the house was spotless when she got home sissy would get a special treat tonight. She let's go of my dick, smiles and leaves for work. Still hard I jumped out of bed immediately a...

Keeping My Sissy Secret

by VrijeVogel on Apr 24, 2019
Transgender & Crossdressers

YES! She really won't be home! I thought to myself as I cycled towards my house. My mother's car was missing from the driveway, meaning her plans for visiting a distant aunt hadn't been cancelled after all. Her wardrobe would be all mine for the entire weekend and I couldn't wait to try on her clothes. Aside from everyday clothes fit for a single mom, there...

My Neighbor is My Daddy Pt. 02

by sissyrulez on Jul 13, 2020
Fetish

(Continued from My Neighbor is My Daddy Pt. 01) I sat in my living room, covered in Daryl's cum. I really should say my Daddy's cum. I couldn't believe I had let this happen. God I'm such a little bitch. I'm Daryl's bitch. Daddy's bitch. I looked at the list he gave me. I needed to buy panties, a butt plug, and a dildo with balls and a suction cup. How am...