Pencil Skirt Stories

117,393 results
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Length
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Infinite Scroll

Quite a First Impression

by HarleyFatboy1 on Sep 15, 2017
Illustrated

My children had been in school for a number of years and I decided to volunteer at the local middle school conducting an art appreciation class for 6th and 7th graders once a week. In order to do this I was required to do a presentation at the Art Institute of our city in front of the school district administrative staff to show my expertise of the subject...

Katie - The Trainee Pt. 04

by Lee0712 on Sep 18, 2017
Exhibitionist & Voyeur

Mr. Oldham came to meet Katie in reception. As he approached her his jaw almost hit the floor! Her boobs were now almost entirely exposed. As the blouse had begun to dry it had tightened and shrunk. Although not entirely dry at least it was no longer as transparent as it had been, but there were still some wet patches that were plain to see and they were off...

Chronicles of a BBW Hunter Ch. 01

by TheGreatRaja on Sep 12, 2017
Exhibitionist & Voyeur

It was a moderately warm summer day, not one of those where you're baking in the sun, but nice. It was just after 4:30 pm on a Monday and I decided to stop by my local Wal-Mart for a few needed things, before going home. Nothing major just a few snack and stuff. For the record I'm not the best looking guy on the planet, but I do all right with the ladies,...

Mary on the Road Ch. 02

by Jappio on Sep 14, 2017
Exhibitionist & Voyeur

Mary sat there thinking about the weekend. They were on the road that she herself had been naked on just a few nights ago. She was day dreaming for awhile, not able to get off her mind that she was bottomless in this car. She had her hands covering up her private area, even though probably only Jenny and Julie would be able to see. "So, what do you plan to...

Accidental Cougar

by LaceStocking on Sep 13, 2017
Mature

Linda arrived home from work and fixed herself a martini. She went to the living room and sat in the oversized armchair. As she relaxed in the big chair, her thoughts drifted off to her daughter, Karri. Karri had started her freshman year at college just a month ago. She was 4 hours away and Linda had not seen her since she had left. Divorced, and with her o...

Anniversary Dinner

by Luvs60smusic on Sep 25, 2017
Exhibitionist & Voyeur

Braless. I don't recall ever going out on a date braless before. A couple months ago, on the way back from dinner with him, in the car, I took off my bra, giving him a peek down my unbuttoned polo shirt. Out to dinner is different. There would be more people around to potentially see. Here it is, the four year anniversary of the day we met. Yes, he still r...

Little Man Pretty Girl Ch. 01

by Scribler on Sep 12, 2017
Transsexuals & Crossdressers

Why I went to the club I didn't know. I guess it was for something to do. I had been alone for so long that I needed the company of others. Even if they did treat me with disdain I still needed to socialize with other humans. You see I live alone and I work from home. I do security consultant work for companies that are having trouble with hackers. Recentl...

Bad Penny Ch. 02

by MVPrimetime on Sep 19, 2017
Group Sex

Mike and I enjoyed watching our girlfriends licking each others pussies. They took their time, responding to each other, mirroring each other. Tara was shorter than Penny, so some movements meant that one or the other had to pause and let their partner pleasure them. Eventually Tara came, and then she insisted on making Penny come. She moved Penny's legs to...

Summer Jobs, Some Are Not

by PMDlite on Oct 5, 2020
Erotic Couplings

This is a work of fiction, although some of the fantasies are real. Please feel free to leave a vote at the end, comments are welcome! Hope you enjoy the story! -0- I decided to treat myself and headed into my favorite diner.. Not that the food was so different or good, but the staff there was the friendliest around and also not hard on the eyes. I had ret...

Nat / alie Ch. 03: Shopping for Two

by Jappio on Sep 14, 2017
Exhibitionist & Voyeur

Part 1a (Nat) I parked my car so I'd have an open space next to me. I waited there for a few seconds... hoping someone else would park nearby or someone would come out of the mall. I was in luck, as a gentleman stepped out of the building and was walking down this aisle of cars. Once he was close enough, I opened my car door. I swiveled my legs to the side...