Stockings Heels Stories

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Derek & Amy: Derek's Turn

by Kalira on Sep 16, 2017
Transsexuals & Crossdressers

As I walked into the hotel room hours in advance, my cock is rock hard with anticipation. The last time me, my lover Amy, and her husband Matt were all together, it was my dear love Amy's turn to be in charge. Amy had Matt and I dress like two Fifties sluts. The kind of girls uptight parents used to believe would cause the downfall of society. It was both...

Get Ahead, Give Ahead

by johnnysdirtysecret on Sep 19, 2017
Transsexuals & Crossdressers

'How do I get ahead in this business,' Jim, the young, eager new intern asked me one day, 'I've been here for months and I don't seem to be getting anywhere.' 'You want the bosses to notice you,' I replied, watching as Jen, another intern who had started at the same time as Jim and was now the company director's personal assistant, sashayed by, 'Start weari...

Buying Heels

by OpenMouth on Sep 16, 2017
Transsexuals & Crossdressers

I have to know what it feels like to wear heels. I have the house to myself tonight and I'm going to play. I already have panties but want to buy some new ones. My wife bought me a black, frilly thong which I wore for her when we went out one night; I also have a cheap, supermarket pair of sheer black briefs, which have a tiny red bow and a little silver k...

My New Life Ch. 02

by quietguyin_tn on Sep 16, 2017
Transsexuals & Crossdressers

(Thanks to all for the positive feedback and encouragement.) My head was buzzing, I could hardly think, let alone feel and sort through all that was going on in my mind. Had I really just played with and sucked a dick? Waives of shock passed through me, am I gay? What the heck is going on? In a short time it all turned into laughter. What does it matter?...

So You Want to be a Nurse? Ch. 02

by MicheleNylons on Sep 18, 2017
Transsexuals & Crossdressers

Education Michele remained tied to the bed, mortified and full of trepidation whilst Dr Lovejoy dressed and left the room. Polly soon followed with the incriminating eight-millimetre film still in the camera, leaving Matron Holliday alone with Michele. "So you see Nurse Nylons we have some very incriminating evidence in our possession. This means you now b...

The Teasing Air Hostess Ch. 01

by footslave85 on Sep 26, 2017
Fetish

It all started at the airport, I had just been promoted and had to start making regular trips to our corporate head office in Germany which required flights every other week for a couple of days. I checked in and was waiting at the gate reading through some papers when I heard the sound of high heels approaching. I've always had a bit of a thing for feet, s...

Walk a Crooked Milf Ch. 02

by MicheleNylons on Nov 16, 2020
Transgender & Crossdressers

Chapter Two - Don't Be a Sissy! "I'm not sure I like you referring to me as a MILF," Mrs Cashmore said. I had counted the hours until I was back in Mrs Cashmore's house. Much to my mother's regret I had not elected to go on to university and had taken a job in a hardware store to help my mother pay the bills. I had told her that I intended to continue my e...

The Older, The Better

by Jack the whack on Sep 17, 2017
Mature

Some years ago I worked at a small engineering firm. One of the typists there was called Barbara, and she did most of the typing for me. I was about 25 at the time and she was coming up to retirement. She was a small lady, and had put a bit of weight on round the middle. She had quite a large bust which she didn't try to hide, and usually wore a skirt and bl...

Summer at Home Ch. 05

by Reindeer58 on Sep 13, 2017
Group Sex

Thanks to all of you who have written me to encourage me to write more chapters. I apologize for the long time between Chapter 4 and this one and I'll try to do better on all future chapters. I suggest that you read the first four chapters before reading this one to become acquainted with the characters. Be patient, this is a work in progress, chapter six is...

Husband's Fantasy

by Fantasy Husband on Sep 14, 2017
Group Sex

I am a husband that has been married to the same woman whom I love very much for over 25 years. However, I like many husbands have this recurring fantasy to watch my wife being fucked by another man and to watch her climax with wild abandonment. There is nothing I can imagine as thrilling than to watch your wife being fucked by another man or men, unless h...