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Transvestite Stories

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Warm And Welcoming

When a widower moves in with his stepson, he finds homemaking not only rewarding but also transformative.

When my wife died, my stepson was still at home. I took care of Brad the best I could for the two years before he went away to college. By then his real father had reestablished contact with him and had agreed to help with tuition costs, which I wasn’t able to do. I got a chance to meet Doug at Brad’s graduation. It was hard to imagine my wife Cindy being married to him; he was so different from me. He had that kind of ma...

Jessi’s debut - A true Jessi story

John goes out as Jessi for the first time and at a party at an ABS of all things.

While what I wrote as how Jessi became an owned slut was fiction and fantasy, it inspired me to do what I did below. (Forgive the slow start but I want to tell the whole story for my own sake) Understand while I would not call myself a prude, I have never been a slut. At forty-eight (basically married for twenty of them) I’ve had three female partners, one male one night stand, and one regular hook up. While I have done s...

Attractive To A Fault

A pretty teen crossdresser's search for her identity

Events in our lives can often change us in ways we never expect. In my case I certainly felt different as a young boy. I possessed very real, mysterious, unexplainable, emotions that I can describe only as feminine needs, in spite of being athletic and quite normal in appearance. These internal feline longings and desires were intense and drew me to all kinds of feminine things. I knew that I loved to feel like and even l...

My First Meeting With Mistress Zara

Maid ruby makes her debut.

First time with Mistress Zara – Chapter One. I am naturally nervous as I arrive at Her door. I ring the bell, and almost immediately the door opens and there stands Her full-time permanent maid, vikki. She is wearing sparkly pink platforms, white seamed stockings, a blonde curly wig, full makeup including the shiniest pink lipstick you can imagine and the most gorgeous dress I’ve ever seen. It is blue satin with pink ruff...

The Prisoner Wore Panties - Chapter Six

POW takes the female lead in the prison play so he can use the disguise to escape

Chapter Six – The White Cliffs of Dover Danielle awoke and was initially unaware of where she was and why she was here.  Then she recalled that she was in Katerina’s flat on Munchener Strasse and the awful events that had predicated her arrival here.  Tears filled her eyes as she recalled how Steven had sacrificed himself so that she and Katerina could escape. She rolled over looking for comfort but Katerina was gone; her...

The Prisoner Wore Panties - Chapter Five

POW dresses takes the female lead in the prison play so he can use the disguise to escape

Chapter Five – Subtleties and Nuances Steven awoke first to find Danielle snuggled up to him; she still wore her stockings and he couldn’t resist running his hands over her legs, rubbing her negligee against her stocking-clad thigh. Danielle stirred and he moved his hand to her groin and caressed her morning erection, feeling the girth of her through the nylon slip and satin panties.  His whole attitude towards Danielle h...

The Prisoner Wore Panties - Chapter Four

Crossdressed prisoner escapes from German POW camp

Chapter Four – Over The Wire “How did you get this Intelligence.  You were in his bedroom?  He fucked you didn’t he?” once again Steven could not control his petulance.  Danielle had been summoned to present the intelligence she had gained at the Oberst's house during the dinner the previous night. Wing Commander Smyth-Waddington had been angry with her for taking the interlude with Oberst Wessel.  He was not naïve; he kn...

The Prisoner Wore Panties - Chapter Three

POW dresses to take the female lead in the prison play so he can use the disguise to escape.

Chapter Three – Oberst Kurt Wessel  “For god's sake will you two at least pretend that you like each other,” Benny was exasperated. Danielle and Steven both had their roles down pat and had mastered all of the scenes, especially the scenes where they argued or fought, but their love scenes were awful.  They held each other apart and pecked each other chastely. “I’ve told you that I’ll fire you and put in the understudies...

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The Prisoner Wore Panties - Chapter Two

POW dresses takes the female lead in the prison play so he can use the disguise to escape

Chapter Two – Two For One “I’m not kissing a man and that’s that!” Danielle said indignantly.   Although Danielle had succumbed to the charms of Mary Mayne, she felt that kissing a man was different.  Mary presented as a gorgeous sexy femme fatale, but Flight Lieutenant Steven Boyd was a stuck-up arsehole of a man. Danielle hated her leading man and Steven despised her back.  He wasn’t really that good an actor but Wing C...

The Prisoner Wore Panties - Chapter One

Flyer in German POW camp during WW2 is asked to play female role in play sees opportunity to escape

Chapter One – Benny’s Girls When the train slowed the young woman stood and took her small suitcase down from the overhead baggage rack. A young soldier across the aisle leapt out of his seat to assist but she already had the case resting on the vacant seat across from her. She smiled appreciatively at him and he sat back down. She took a compact out of her purse and freshened her makeup and touched up her lipstick; she b...

Barrack Room Betty - Chapter Sixteen

Final chapter for few following this story - enjoy

Chapter Sixteen – Barrack Room BettysThe voyage back to Portsmouth was via Fremantle Western Australia, Colombo Sri Lanka, with a final fuelling stop at Gibraltar. It was uneventful until the last night at sea. Barrack Room Bettys had been filled to capacity every night as the ports on the return voyage were not particularly conducive to the sort of carousing that the sailors liked to get up to.The girls of BRB literally...

Barrack Room Betty - Chapter Fifteen

Navy Transvestite Girls visit Sydney Australia

Chapter Fifteen – Bettys Down UnderMichele had an emotional last day with Ying. As well as lovers, they had become good friends. Michele promised to write to Ying and vowed that one day she would return to Thailand and they would reunite. Their last night together was a sex-charged boozy affair and Michele rose early the next morning and left Ying fast asleep in the hotel. She was emotionally drained and didn't want an ex...

Barrack Room Betty - Chapter Fourteen

Michele meets a Bangkok ladyboy and they strike up more than just a friendship

Chapter Fourteen – Supergirls Bangkok“I’ve fucking had it with Jason!” Michele spat at Rod Latham“That fuckwit tracked me down and found me in a bar in Naples and created an absolute shitfight. And every night I’m here in the club, he carries on like a petulant child whenever I work a punter and in particular Lieutenant Steve Winters who is one of our best customers. When is that fuckstick going to realise what happens on...

Barrack Room Betty - Chapter Thirteen

Transvestite Wrens visit Naples and have fun in the sun.

Chapter Thirteen – Naples – Whores and PrincessesThe Ark continued her voyage through the Mediterranean Sea, exercising with the Task Group as she went and arrived in Naples a week after she left Gibraltar.Lieutenant Steven Winters, RN, became a regular at Barrack Room Betty’s whenever there was no night flying. He entered into an arrangement with Michele that she would always be available for him at thirty pounds per wee...

Barrack Room Betty - Chapter Twelve

Crossdressing sailors operate a brothel on a navy ship

Chapter Twelve – Pleasuring an Old FriendArk Royal sailed for her deployment in a small Task Group of three ships and on the first night Barrack Room Betty’s opened for business and was an instant success. At first, the main earner was gambling and booze but as the ship got further away from her home port the temptation for the punters to ‘tap’ the attractive transvestite hostesses became more frequent.Michele divided her...