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Michelle2023
6 hours ago
Heteroflexible Male, 70
0 miles · Cockermouth

Stories

Series

The Rodeo Continues Part 1.

Well and truly... putting the sex in sexagenarian.

Linda received a text from Judy the following morning apologizing for Billy's behaviour. She also said in her text that she would love to get together with us, and Saturday night would be good for her. "She's keen." Linda laughed. "You doing anything Saturday?" "What! No!" And if I was, I would have cancelled it... Only two more sleeps! The following evening, Linda and I planned for our night with the newest member of Mic...

A Cross-dressers Dream!

It's been a long time fantasy of mine, to spend a day in the life as my wife... at her workplace.

The landline phone by my bed had been ringing for quite a while before I realised it was not in my dream. "Hello!" "Hi!" It was my wife. "Were you asleep?" "What! Well yeh!" I was still groggy. "What time is it?" "It's almost nine." "NINE!" I couldn't believe my wife had rung me at this ungodly hour. "... in the morning?" "Well yes. Of course in the morning. I just got into the office. Have you seen the weather?" "No! I w...

Maybe My Last Rodeo (Part Three)

The realization that I still have a few crossdressing years left!

As 'Michelle' outings go, It had been quite an evening. A milestone achievement in the life of a 'hanging on in there' cross-dresser. After fifty years of sporadic sessions, of pretending to be a female, and not since Michelle and Linda sauntered through the red-light district of Amsterdam, had I felt closer to my fem-side. It was just after nine-thirty when I drove into the Old Coach-House Inn car park. It would appear t...

Maybe My Last Rodeo (Part Two)

My crossdressing clock is still ticking and there's still one more thing on my 'fuckit' list.

One thing was for sure... there was no way on God's earth, that Bob's monster cock would slide inside my tight little man-pussy. But I could give him the best blow-job he's ever had, on that, I could be sure. In my time I've been on the receiving end of many, and feel well-qualified in the art. I blew Bob a kiss and prepared to leave the house. The car was in the driveway and I hoped there would be enough fuel for the sho...

Maybe My Last Rodeo (Part One)

My crossdressing clock is ticking and there was one more thing on my 'fuckit' list.

It had been over a year since my last dressing. As I enter my mid-60s, the phrase "mutton dressed as lamb" has extinguished any urges that I've had to dress en-femme. My legs were always my best feature, and I loved to show them off with a mini-skirt or dress. Alas, not befitting for a woman of my age these days. My face when made up, was passable back in the day, but now there are a few more wrinkles to conceal. Any hoot...