Stockings And Heels Stories

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Ananda Ch. 03: Takes The Lead

by monkeykinglives on May 4, 2020
Group Sex

Ananda Takes The Lead All persons depicted are over 18. This is the third part of the Ananda story. In 'Ananda Visits Her Nanny,' my friend's daughter visits and gets her cherry popped by me after a street festival. In the second part, 'Ananda Returns With Her Roommate,' Ananda returns a year later with her blonde roommate and shows me her new skills. In...

9 Stone Cum Queen in the Suburbs

by 9StoneCumQueen on Sep 18, 2017
Fetish

(This is my third story for Literotica) * Here I am. I am the 9 Stone Cum Queen. My cunt is tighter than your wife's. I am five foot six. That's the perfect weight for my height, a doctor told me. I'm a good height for the average man. When I'm wearing heels and I bend over a table I find my cunt is at just the right height for the average man to slid...

It Starts at the Airport

by CDBeatrix on Sep 16, 2017
Transsexuals & Crossdressers

You are arriving on a flight. You were specific on how I was to dress when I picked you up. Pink stockings with a black seam and 5" heels with a locking ankle strap. The stockings to be attached to a pink corset and a thong. Covering all this is a thin black trench coat that barely covers the lacey tops of my stockings. A locking choker and a chauffeur hat....

Laura's First Time

by Lauralust on Sep 15, 2017
Transsexuals & Crossdressers

It was Friday afternoon about 4:30 and I was just arriving home from work. I was looking forward to a quiet evening of relaxing as my other persona, Laura. My roommate Mark had gone in on afternoons and I had the apartment to myself for the next few hours. I stripped down to my silk undies and stay up stockings that I had worn to work in anticipation of dres...

Sandy Transforms Her Lover

by Cexylady on Sep 16, 2017
Transsexuals & Crossdressers

Sandy was tired, she had a good life, her kids were grown and out on their own. She worked only because she wanted to, she was financially secure as her husband had provided her, Bill had been taken from her by a fatal automobile accident. Sandy was finally over grieving the loss of her husband, she was getting on with her life. She enjoyed working out at...

Not in Public, People will See

by yorktvjane on Jul 15, 2020
Transgender & Crossdressers

My boyfriend loves to make me cum in public and every time we go out in public, I know there is a chance I am going to be milked fully to completion, even if there are people milling about, terrifying, but ...I love it. It's a nice sunny Sunday in early December, its mild for the time of year and we have parked up in Rowntrees park close to the center of Y...

Trained to Have Transvestic Fetish

by Everyday2 on Sep 12, 2017
Fetish

A Problem to Solve I have known for years that my husband of 17 years was intensely interested in panties and just loved seeing panty lines or exposed lace on women when we were out and about. It kind of made me mad that he would so blatantly stare at other women like that, especially since I usually wore sexy panties myself that I wanted him to notice. I w...

Backwards in High Heels

by thrillerauthor on Sep 15, 2017
Transsexuals & Crossdressers

I'm told that when I was two or three, my mother dressed me as a girl and took me trick-or-treating with my older sister on Halloween, but I have no recollection of the event. * * * Fast forward ten years, when I was on the brink of puberty. For some reason which I will never understand, I developed a fixation on trying on my mother's high heels. One nigh...

A Trip to Remember Ch. 01

by marykay9 on Sep 16, 2017
Transsexuals & Crossdressers

I live in Los Angeles and don't get much of a chance to practice my hobby of cross dressing. Once per year however, my company sends me to an industrial convention and I take full advantage of the opportunity. This year I was to travel to San Antonio, Texas, to attend a conference at a large hotel located on the River Walk. I packed two bags, one with my b...

Marion Turns Me Round Ch. 02

by jomar on Sep 16, 2017
Transsexuals & Crossdressers

You might want to read the first chapter for context.... On the other hand, you know what you're in for here. I hope you enjoy the kink, baby. ***** I was back for more the next night. I figured that a blowjob from a pretty woman was worth the time, even if the pretty woman was Marion's boyfriend, a feminine man dressed in lingerie. Her androgynous looks...