Plaid Skirt Stories

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Orientation
Length
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Infinite Scroll

Fun with Trevor

by WatchedBeth on Sep 24, 2019
Exhibitionist & Voyeur

Roger Still reeling from crossing the line with Roger, I was surprised how easy the plan came together and how eager Roger was when it came to it. I knew there would be more fun to be had with Roger but I also had to make sure he kept it to himself. I didn't want to risk losing my job over a little boasting by Roger to his friends. So on Tuesday morning I w...

The Path to Happiness Pt. 03

by brendachaplin2000 on Sep 23, 2019
Transgender & Crossdressers

I woke from a blissful slumber to the smell of coffee. I was grateful for the sofa that acted as my bed in my squat, but this bed was so comfortable I did not want to get up. As my senses returned to me, I noticed my arse was a little sore, Becky's cock cage would need more lube than a little spit if it was to go back in me. I slipped reluctantly out of the...

Gerina - The Prequel

by grgy56 on Oct 30, 2018
Transgender & Crossdressers

"Oh fuck! I'm cumming! F..u..u..c..k!" I cried to myself as my large, white, hot load shot from my cock between my fake "C" breast forms and landed on my parted red painted lips and tongue. The second load laid a stripe down from my neck between my tits and stopped at my belly button. The third, filled and pooled the aforementioned belly button. My name is...

Control Ch. 09

by thisonelad on Apr 15, 2020
Sci-Fi & Fantasy

Samantha Eldridge was proud of herself. At the young age of 25 she had already made herself a millionaire in the telecommunications business. Her climb up the corporate ladder had been swift and efficient. Two thousand people technically worked under her now, many a great deal older than her. Too bad, she thought. Some people just aren't cut out for upper ma...

Pregnant Milky Milf Ch. 03

by MohanSingh on Jan 21, 2020
Erotic Couplings

I wore my black demi bra and thong on my first day as the Executive Assistant to Anand Chaggar. A shiver of excitement ran through me as I thought about my interview and how he had used my body. I found an old skirt that came just above knee length and I wore a blouse and tights. I also had a black blazer that completed the outfit. I checked that the maid...

Robert & Beth Ch. 06

by sirdix on May 13, 2020
Loving Wives

Las Vegas Vacation-Part One Beth has become a hot wife. Now it was time to go to sin city, Las Vegas. Told in two parts, Beth fully embraces the slut lifestyle, and Robert couldn't be happier. A few months passed. During that time, Robert and Beth talked about that night. They finally concluded that Beth wanted to be with other men, and Robert loved to w...

Compromising Positions Ch. 10

by Timeris on Jun 9, 2020
Exhibitionist & Voyeur

As they sat around eating, they began talking. Jenne told them of her recent transformation, and how amazing her week had been. She glanced at Angela with affection. "I'm so lucky that I found Angela, and I found you guys. It's really been incredible." Cheryl got a mischievous look on her face. "So what was up with you the other day? You could hardly talk y...

Yes Sir

by lacecorset on Oct 6, 2020
BDSM

The room is quiet as you look at me, seeing what I wore today. The skirt is your favorite, the soft gray with the slit up the back. The shirt is magenta, with a bit of sheer material along the v-neck. After leaning in to give me a kiss you ask, "Did you leave off the panties today." I answer, "No, it's a bit cold out today." "Didn't I say that whenever you...

G's Submission Ch. 14

by ssubramaniam122 on Sep 25, 2017
Exhibitionist & Voyeur

I hardly remembered anything at this point. I was high. I had just witnessed what my crazy sexual appetite was capable of. The last few hours were only too rapidly becoming a distant memory. I needn't worry about them, need I? The brain has a curious way of dealing with these moments. Whenever I felt I had to calm my hormones and think about what I had don...

Caught by my Sister

by centrum1000 on Sep 26, 2017
Transsexuals & Crossdressers

It was 10 o'clock on a Friday night and I was all alone in the house. My Mom, Erica, who was in her late 30's and recently divorced was enjoying her new found freedom by going out with he girlfriends. My sister, Jane, was out with her friends for the night and that left me alone as usual. My name is Brian and I am an eighteen year old high school senior. I...