The Ideal match. A story of love, crossdressing and deceit.

To say Amelia is a voyeur is a little simplistic. Amelia is downright perverted, and that comes out in many ways, ranging from the delightful to the distasteful.

I hold none of this against her, however I am very much aware that when she arrives at my rooms dressed smartly, fresh from her office, and clutching a notebook in her hand I can be sure she’s going to ask me to do something complicated, not to mention enjoyable, to her long suffering husband.

Several years ago I first met Amelia, when she was still engaged to Geoffrey, her husband. At that time it was all simple enough.

“I’d like you to dress him up, let him wear some nice clothes, and teach him to walk nicely in heels.”

That was all simple enough. There was but one proviso. She wanted to watch. Of course, I’ve been asked for such services many times. However, Amelia didn’t want Geoffrey to know she was watching. In fact, he was never to know that she was even aware of her knowledge of his secret passion. As far as he was aware he had been fortunate enough to get a gift card to my service as a present, and his fiancé had no knowledge of what went on in the privacy of my rooms.

It took me only a few minutes to deduce that he was a crossdresser and needed the release of being dressed at the hands of a firm woman. And, of course, I fulfilled that desire very willingly. Even to the point of instructing him in his release.

First I’d dress him, have him walk to and fro before a mirror, look surprised at the way his dick disturbed the cut of whatever he was wearing, and then I’d instruct him to jerk off, sometimes into a wine glass, all in view of a discrete camera which his dear wife was monitoring from another room.

And what, you may ask, was Amelia getting out of this little exercise? While watching as her (now) husband jerked off in front of me she was witnessing his transformation. I asked her about it one day as she sipped the glass of wine I provided her with in the room from which she could monitor his activity.

“What exactly is it that you get from it, Amelia,” I asked.

“Oh, it’s very simple. I like to see him reduced.”

“I don’t understand,” I replied.

“You see he’s generally very commanding. He runs a dynamic little company that’s quite successful. When I come here and see him dressed in a sissy maid’s outfit, sucking an enormous dildo, I am reminded that he is just as human as the rest of us.”

“I see,” I replied.

“Yes. Take last night. He was at a charity event for the local hospital. All sorts of people were there. There was an art auction. Some of it was alright, but most of it was really pretty awful. But by bidding on some of the paintings it gives us a way to donate some money to the hospital, and it’s tax deductible of course.”

“Go on,” I said, wondering where this was going.

“Yes, so when he bid an outrageous amount for some complete garbage art, and everyone in the room looks at him, and all those little wanna be trophy bitches look at him, I am reminded “Geoffrey just loves to dress as a sissy wrap his lips around a nice big dildo. He’s as human as the rest of us,” said Amelia. “And when he walks up and is all smiles picking up his art, and everyone thinks how wonderful he is, I know he’s just a little cum drinking sissy that wants to be on his knees taking nine inches of silicon in his ass.”

“I could see how that might give you a slightly different impression of him,” I said.

“Oh yes. I think it keeps us both grounded.”

I left her to her wine and the monitor, and returned to the studio, where I was instructing Geoffrey. His make up was getting much better and he did look particularly nice in heels.

Geoffrey believes that as I carefully move him further along this path he is driving the progress. He has no idea that it’s usually Amelia who is deciding where this goes. Today for example she wants him to be bound, plugged, and forced to watch gay porn for twenty minutes or so, before being left along with the porn, a substantial dildo and some lube.

He will voice his desire to watch straight porn, naturally enough, but will do as I tell him. He often pretends to prefer straight porn. But that’s really not the point, is it? Amelia wants to see him exposed, and likely pleasuring himself, to gay porn. She wishes to witness his corruption.

I will not suggest to him that he should do anything with the lube or the dildo. Far from it. Amelia knows very well what she wants. I am simply to leave them on the coffee table where he can pick them up of his own volition, if he so chooses. And he will. In doing so he is leading himself further down this path. And each time it is a little further.

The poor fool doesn’t realise that his wife is laughing to herself, getting off on his decent into deeper depravity each time. She will leave unseen as he dresses in his street clothes after his session, arriving home shortly after her. To enjoy a meal with his loving and domestically perfect young wife. And all the time she has that secret knowledge that behind the professional exterior there lies a little cumslut, still yearning for more dick.

As I clean the room Amelia has been watching from I notice a little bit of a finger print on the wine glass I provided her with. Anyone would think her fingers had been a little damp, or sticky or something.

I do like Amelia.

Mistress Katia Thornwood

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