tagTranssexuals & CrossdressersAnd When I Return Ch. 01

And When I Return Ch. 01


The first of many chapters to come. This may not appeal to many, but I hope that those that like it, like it a lot. Smiles to all those cross dressers, fetishists, and sissies out there.


Jason had been dreaming of this for years, planning it for months, and as he lay in bed, sleepless beside his wife Jenna, he had some last minute pangs of guilt. The two week excursion laid out before him was held together by a complex network and web of lies, all of which had been built and nurtured for a very long time to deceive Jenna. And as in all webs of lies, the stories became complex, interwoven and hard to manage, so difficult in fact, that he sometimes panicked when she asked him questions like: "So, when is your flight?" or "What airline?" or "Why aren't you taking your laptop?" or "Why are you taking two suitcases?" It was endless.

It all had to tie together, but in the last twenty-four hours his excitement had built to the boiling point, his skin occasionally flushing with pent up energy and adrenaline, and he sometimes stumbled, saying, "The flight's at 0805, no 0835 with Air Canada...I think."

"Let me see your ticket," she had said.

"Oh, it's packed. It's 0835, I'm sure," he answered hurriedly and with artificial confidence.

There was no ticket.

"Packed? Why would you pack your ticket Jason? You need it in your hand," she had said, puzzled.

"I mean it's in my brief case," he answered. His face felt hot and red.

"Well, your brief case is right there. Get it out so we can check."

For this he relied heavily on his amateur acting skills by smiling and softly saying, "Relax, okay? The flight's at 0835. It's with Air Canada, and I need to be at the airport at about 0700, leave here at about 0630. Is that detailed enough?"

He had hugged her then, but she had resisted his pull initially, still puzzled and curious. She eventually melted into him and said gently, "Let's have sex tonight okay? I don't want you leaving horny and finding some hooker in San Francisco or something."

Jason had panicked at that invitation, for his mind was far, far away from vanilla at the present time. But he hugged her close and replied in a whisper, "Okay, that would be really sweet honey. Let's go into the hot tub first, have a glass of wine, and let it build."

He pulled away, proud of himself for sounding so natural and loving, and smiled at her. He hated himself for that.

That was then. This was now. He laid there guilt-ridden. The sexual play had not built as he had said and he had simply been unable to act it all out. He had overpromised and underperformed, well, had actually been unable to perform at all, other than oral sex for her. Penetration was like pushing on a rope, and no amount of dirty talk or manual stimulation on Jenna's part seemed to help at all.

He had eventually rolled off to the side, saying, "I don't know what's wrong. I guess I must be nervous about this course. It's going to be intense."

Jenna had been very understanding. "It's ok. Not the first time, or the last," she said. Then she smiled a weird grin and added, "And I'm sure you are nervous. The next two weeks are going to be very intense for you, maybe even more than you imagine. But you're more than ready for it aren't you?"

With impish intimacy, she patted him on his limp penis and said, "Now go to sleep. You're going to need it. Good night sweetie."

At that moment he had never loved her more, and at the same time he had never felt guiltier. His mind leaped about, trying to sort things out. Thus the sleep did not come.

At one point he thought about waking Jenna and confessing that it was all lies, but he had literally spent thousands of dollars on this fourteen day adventure. He had been surprised at how much money Mistress Diane had demanded for specialized clothing and equipment for his visit, but she had assured him that based on his description of his fantasies, the gear was essential. Other than the sunk financial costs however, there was the sunk emotional cost, expressed in the dreaming and fantasy, the realization of a life long craving and need. This trumped even the dollars, and he let her sleep.

Mistress Diane had refused to tell him what the clothing and equipment were, but she had said several weeks ago that it was all based on the descriptions of his fantasies and fetishes that had been input to her questionnaire on her website, a list that even she had been impressed with.

Do you like:

Cross dressing?Yes Being submissive?Yes Wearing panties?Yes Skin-tight female clothing?Yes Wearing bras and girdles?Yes Corsets?Yes Makeup, wigs, high heels?Yes Do you like role play and cross dressing in general?Yes Rubber/latex enclosure (clothing, other)?Yes? Leather Bondage?Yes Steel bondage?Yes Discipline?Yes? Erotic humiliation?Yes? Anal toys?Never tried

If "Yes" to cross dressing, do you possess:

Female clothing and gear?Yes What types?Skirt, dress, pantyhose, panties, girdle, bra, wig, high heels (one pair), some makeup

The question marks after his answers meant that he either did not understand or that he was curious about the item. He sensed that Mistress Diane did not recognize his reticence. This was just a taste of the questionnaire, but these items had been burned into his psyche and memory, as they claimed most of his interests. He had given her carte blanche with her request of $7,000, an amount large enough that he had taken great lengths to conceal the expense from Jenna. That was on top of the $800 per day that Mistress Diane charged for her services. The amount was staggering, but being a doctor had its perks. What had she bought with the money, he wondered?

Jason rolled over, frustrated in his attempts to sleep. He found that he was hard, and that disgusted him. He was lying beside his wife for Christ's sake! The love of his life, that he had been unable to make love to just an hour ago.

He sat up and squinted through the gloom at her breasts rising and falling in deep sleep. A ringlet of her long brown hair lay across her face and her nose twitched in reaction to the tickling of it.

He couldn't do it. He could not wake her. If necessary, he would seek forgiveness rather than permission, as the latter was not on the table.

Seven years ago, months before they were married, Jason had told her one Friday night that he was going to cook supper for her, with candlelight and wine, the whole works. They lived in an apartment then, and after a couple of glasses of wine, they snuggled while the spaghetti sauce simmered. Finally he screwed up the courage.

"Jenna," he said softly, "I have something to show you, something that has been with me all my life, but I haven't shared it with anyone. I love you and I want to make sure you know everything about me."

He stared intently at her face which instantly went rigid with dread. "Oh God! Please don't tell me you're gay!" she said, as she stood up, out of his gentle grasp.

"Jenna, calm down okay. I'm not gay, and I want you so much. That's not it."

"Well what is it then? You're scaring me."

"Look, rather than tell you, I'm going...just give me half an hour okay? I'll be right back."

"Half an hour? Do you have to go pick up a long lost son or something?"

"No," he laughed, "Nothing like that."

This was it, he had thought at the time. He had crossed the Rubicon. As he shut the bedroom door behind him, locking it to ensure privacy, his breathing was ragged, and his face felt hot. But the decision had been made.

Twenty five minutes later, he stood at the entrance to the living room. His legs felt the draft from the open balcony door, even through his pantyhose. Stress sweat pasted his water-filled plastic bag inserts to his chest, supported by the bra. The girdle compressed the bulge in his groin, and his lipstick tasted strange as he bit his lip, hesitant.

Jenna was in the dinette staring absently out the window, sipping on the Chardonnay, oblivious to his presence. He took one step forward in his high heels, feeling and hearing the hiss of his dress across his feminine undergarments, and cleared his throat.

He walked forward and said, "Jenna, this is me. Please try to understand."

She looked and froze in silence. Finally she rolled her eyes and said, "Ha, this is a joke, right?"


"So, you ARE gay then," she whispered, her voice trembling, "Christ, oh Christ!"

"Jenna, please! I am not gay. I have a fetish for women's clothes, especially tight girdles and the like. If I was a woman, I'd be a lesbian. I want YOU Jenna. And this is me. The same me that you love and who loves you, but I'm in different clothes. That's all."

He sat down beside her at the table and picked up his wine, gulping an unusual and rather unfeminine amount of it at once. He set the glass down, revealing the lipstick stain on the glass.

"You, you've got makeup on?" she asked tentatively.


"You like makeup. You like dresses and girdles. Jesus Jason," she said with a tremble, "Looks like a duck, quacks like a duck. I'm not feeling this. I'm not...Jesus, give me a minute okay?"

He did so. She stood and walked into the kitchen aimlessly, and when she turned around to look at him again in disbelief, she noticed his high heels for the first time.

"Really? High heels?" she asked, stunned.

He had had no predictions in his mind as to how this should have gone, but he felt everything slipping away now. Abruptly he said, "Look, let's just try to relax and have some more wine, then supper, okay? I realize this must be a huge shock."

"Shock," she said in deadpan. She sat down and finished the last third of her glass of wine, setting the empty glass down with an aggressive clink on the table.

The questions slowly began to pour from her. How long have you done this? How does it make you feel? Why? Do you want to be a woman? Do you want to get a sex change? Are you sure you're not gay? How often do you do this? Are you sure nobody else knows?

Neither of them enjoyed the rest of the wine or the supper. The conversation between them slowed and stuttered until finally at the end of the meal, Jenna said, "Look, I'm really uncomfortable with this. I'm really sorry Jason. I know how much courage it must have taken for you to tell me, but...I do love you, but...look, I can't. I just can't accept this as part of us. As part of you, yes, I guess I can accept that, but not on my time. I'm sorry Jason, I really am. I need you to take all this off. Please."

She waved her hand vaguely around his body and added, "You can dress in private if you want, but not with me. Ever. I just can't. I, I'm just not built for this I guess."

Jason was sweating in the bed on this hot July night as he recalled this trauma seven years ago. He had felt like she had kicked him in the stomach, but he had hidden it well. He also knew that she had felt the same way.

He had said, "Okay. I understand. Kinda sick I guess. I shouldn't have done this. I just wanted you to, I just needed...umm, I'll go change. Then we can have desert okay?"

He had taken twice as long to change out of the clothes as into them. His shoulders sagged as he entered the bedroom and he cried, not feminine tears, but just watery eyes that dripped only when squeezed shut. This was the love of his life, the girl of his dreams, but there was one little piece that did not fit in their complex jigsaw puzzle of a relationship. Now he knew there would always be that hole in the picture, always.

Looking back on it, he should have walked away. She should have walked away. Funny what love does though.

They married and he stuffed his longings back into a tidy little box in his head, and threw out all his feminine attire, determined to be a normal, loving husband. But it festered and burned like an underground fire, squirts of fantasy smoke rising from him over the last three years, buying a girdle here, panties there, a bra, pantyhose, until he had a stash of guilty joy hidden away in the basement, away from her. Their bed became two valleys with a mountain between where they met for the obligatory sex once a week on Saturday night, the lights off, panting and gasping for relief.

He looked at the clock and the glowing digits said 3:36. The next time he looked, the alarm was blaring its annoying enh enh enh.

He rose, instantly excited at the prospects for the day, and indeed the next two weeks. But Jenna seemed pensive. They sat and chatted awkwardly, sipping coffee and waiting for the cab. It felt like that night again.

Finally and mercifully the cab arrived. Jenna helped him put his two bags in the trunk and gave him an exaggerated kiss and a brisk hug.

"I love you," she said, "Have a good time in LA. And don't come back too beat up."

"I love you too," he replied. Did he tell her LA? He thought he had told her San Francisco. Beat up?

She turned and went onto the doorstep to wave him on his way. Jason sat in the back seat of the cab and said to the cabbie, "Budget Rent-a-Car please."

The cabbie turned around, puzzled, and said, "Budget Rent-Car? Which one?"

"Any one," he answered, "The closest I guess."

Toronto was slowly waking as the cab made its way the few blocks required to get to Budget. Within half an hour Jason was on his way.

At a stop light he texted Mistress Diane, "Just leaving. Be there in an hour."

To Jenna he texted, "Plane delayed. Leaving at 0855. Sorry about last night. When I return, I will be different. Love you."

The light turned green and he was gone.

At home Jenna read his text and replied with I love you too. She smiled sadly and shook her head. She hoped this course would be worth it. She missed him already.

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by Anonymous

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by Tootight105/15/18

Totally loved it so far

I think what I loved about it was the reality of it. From my own personal experience. I couldn't do what he did though. An online Mistress, no way. Life is too precarious today to afford that much trust,more...

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