Cara and her husband Terry have worked out a wonderful way to balance a need for discretion with a wonderful transformation. But I will let Cara tell her own story.
Dear Miss Jay,
I adore your blog and your books - not just A Man in My Position and the other dominant wife material - but also your wonderfully detailed and open minded exploration of how powerful women can maximize their potential as escorts, or, my favorite, mistresses. (The retro smut you have elliot publish I give to my Terry as a special treat.)
I suspect I was drawn to your work on the interesting nexus between sex and money because I met Terry when he was my escorting client. Though I use "escorting" in a very loose way. I had a small business catering to cross-dressers and transvestites (and if you can tell me the difference my hat is off to you, but it was very important to the men I saw.)
Believe it or not, I got into the business when I was a make-up and special effects artist. I spent my days making pretty girls prettier and, from time to time, making them scary. It was a good living and a lot of the sets I worked on paid a cash bonus. On one of these shoots a model I knew slightly asked if I could do a friend of hers make up for a party. I said sure and thought nothing of it. We arranged to meet her and her "friend" at her apartment the next day. Well, like more than a few models I knew, this girl supplemented her modelling income with pay to play encounters and her "friend" was a client who wanted to "Walk on the Wild Side". It took a little doing but I managed to create a passable impression of a woman - but he walked like a trucker. I spoke to my friend who agreed and then I suggested that, if he wanted to, I could offer him some "training" as well as the make-up and clothes. He jumped at the chance and my model friend told me later she had two other clients who wanted this sort of feminization and it was not her thing. And she had friends in the business for whom crossdressing clients were actually a problem. I was launched.
I would only see three or four clients a week, charge a high fee and make a "best efforts" attempt to let them appear and behave as women. I say best efforts because, realistically, very few men have much hope of "passing" for a woman but they seemed to have fun trying. My sessions were quite long, two hours minimum, often four.
Most of my clients were very regular and, once they had done their introductory appointments, I laid on a program of deportment, skirt management, high heels training and so on. There was no "sex" of course. However, at the end of the appointment, if they had been very good, I would tell them to go to the little girl's room and make a mess in their panties which they then had to lick clean before hand washing.
The key insight I had into these men was that they all were, to some degree, ashamed of their need to dress as women. And, here was the thing, they enjoyed the shame and humiliation of having to put on lingerie, foundation wear, wigs, breast forms, false eyelashes and so on. If I didn't tease them, demand instant obedience and tell, not ask, them to put on their "pretty" clothes they would be disappointed in the session. They wanted to be "forced". And yes, I did threaten to spank my naughty boys and, occasionally, it would be necessary as part of a session to paddle or cane a client quite severely. Of course, "quite severely" was a very relative term. The objective was to create a reason for the client to comply with his own humbling - which was the very thing he wanted.
Men! What can you do?
In my case, I charged a lot of money, built up a remarkable collection of plus sized lingerie and outfits - my clients, as part of their training, were required to purchase these items and bring them to their sessions. This all took place several years ago but even then you could get everything from side zip girdles to breast forms to plus size high heels at Amazon. You could even get the correct "gaff" panties to keep every little thing in its place.
It was all part of the ritual and the ritual was very important to my clients. For a few hours, they were going to be "forced" to be female. In a couple of years, I actually had a waiting list.
Terry was a referral from one of my model/escort friends and I saw him really as a favour. He was pretty run of the mill as clients went and I was just going through the motions as I corseted down his waist and put on the breast forms. For cross dressing, Terry was lucky. Not only did he have a gender neutral name - Terry swings both ways but he was almost hairless and was small boned if a little plump in places. The very opposite of "buff". With the corset giving his already quite tight waist a lttle shape and the "C" cup breast forms in place in a lacy black I had him slip on a pair of black satin tap panties. He was a natural blond with a rather nice full head of gently wavy hair. Rather than put him in a wig, I put in hair extensions I happened to have. Light make-up, really just a very transparent foundation, mascara and eye shadow plus a light pink lip and he was done. I clipped semi sheer compression stockings to his garter tabs. (Pro-tip, compression stockings help shape a man's leg and hide any hair which a first timer is likely to have. Plus they feel as if you are actually a naughty boy wearing stockings.)
A simple pencil skirt and sheer blouse and a pair of modest two inch heels and Teri was done. By this point I had done transformations for a fair number of men. A few, a very few, could pass after several sessions. Teri stood up and walked over to my three way mirror. He was a little awkward in his heels but, honestly, with a bit of practice, it would be very had to tell. He had delicate wrists and his Adam's apple was inconspicuous and could be made more so with a bit of reverse contouring.
"Wow," was all he said as he looked at himself in the mirror. "I never thought I would be this pretty."
He was not wrong. Unlike many men Teri suited the longer hair, the makeup, the clothes. We practised walking in heels for a little while and then I had him make and serve me a cup of tea and one for himself. It all seemed perfectly natural. As Teri he was quite feminine, funny in a slightly exaggerated girlish way and rather flirtatious. It was quite a long session and I had him change into a shorter skirt at one point. He was naturally rather modest and went behind my screen rather than showing off his lingerie. Eventually I said I had another appointment and Teri went behind the screen and undressed and came out in the lacy ruffled lilac robe I kept for clients; makeup and hair still intact.
"Come here," I said, "Open your robe."
He did as he was told and stood in front of me his little cock - and it was quite small - naked and erect. I reached out and took it in my hand.
"You enjoyed dressing up as a girl didn't you," I said gently pumping his cock.
"Yes, Miss," he said.
"And you'd like to do it again wouldn't you Terry?" I said pumping a little faster.
"Oh yes Miss."
I could feel him coming very close and I let go of his cock.
"Good. I will see you next week. Now get dressed."
He was, I suspect, a bit disappointed that I had not taken him to completion but I had other plans.
He arrived the next week and we did much the same thing. I was a bit more prepared with sizes and I had a surprise for him at the end of the session. I had him, once again, undress from his girl clothes behind the screen and came out in the peach robe I had bought him.
"Terry, when you left last week did you go home and ejaculate?" I asked holding his hard little cock firmly.
"Yes, Miss, twice that night and two or three times a day since. I can't help it," said Terry.
"I thought so," I said. "That won't do at all. Girls don't masturbate the same way as boys so we're going to have to make sure you behave. Now, here's a tissue. Jack yourself off for me."
"Yes, Miss," said Terry as he began to pull on his cock.
"Faster, I don't have all day," I said which was all it took to send plumes of sperm out of his purplish cock head. "Now, go over to that corner with my panties (I am a huge fan of corner time for men.) and hold them in the corner with your nose."
Terry did what he was told and ten minutes later I called him back. As I suspected he would be he was just as hard.
"Now, I could whip that erection away or put that naughty little cock in ice water until you get soft; but instead, jerk it again. Quickly," I said handing him a dish. "Every drop in the dish."
It took a little longer this time but in a couple of minutes there was a nice dollop of cum and several drops and strands decorating the china dish.
"You know what you have to do, Terry," I said looking at the dish. "Lick up your mess."
It was a test he passed eagerly.
"Good boy," I said reaching around for the package I had received air express.
"Now, Terry, good girls always ask for permission to masturbate. Which I know is hard for girly-bois so I have bought you a little gift. Turn around and put your hands behind your back," I said. I took a pair of handcuffs and clicked them locked. "Turn around."
Terry obeyed and I opened the box the male chastity device came in. "Do you know what this is, Terry?"
"No Miss."
"It's a cock cage. You'll be wearing it when you are not in lady's clothes," I said putting the pink silicone ring around and behind his balls. Then, using my fairly long but nicely squared fingernails, I reached under the head of his cock and pushed it into the silicone cage. He was soft enough that it was easy to get most of his cock in the cage and push the holes over the pegs. I reached through the little slot in the end and grabbed the head of his cock with my nails to pull it all into the cage. Then I slipped the padlock through the short peg and clicked it shut.
"There you go," I said. "All tucked away and I have the key. Now you can get dressed and I want you to pick me up for dinner on Thursday. Seven o'clock. Dress nicely as I am taking you somewhere special.
Two months later we were married in a civil ceremony. I wore a lovely 40's suit, seamed stocking and a pretty, veiled hat. Teri was dressed in a light linen jacket, a pair of side zippered linen trousers, cute loafers, his cock cage for lingerie and his now longer hair pulled off his face with two butterfly barrettes.
I took him back to my apartment, had him put on his nightie for bed and then gave him a good hairbrushing to set the tone of what has been a long and happy marriage. As you can imagine, having been kept in his cage for the three weeks before our wedding night, he was very anxious to perform his marital duties. I, on the other hand, thought that could wait for our honeymoon and enjoyed Teri's girlish tongue on my throbbing clit.
We were honeymooning at a small country house I owned about forty miles from the city we live in. I drove. Teri had changed into her going away outfit. Nothing elaborate, a day dress in a fine grey cotton with a little, to the waist, black jacket. Corset, girdle, bra and breast forms, hair extensions in and nice day make-up as I had instructed her to.
"In the country, Teri, you are always going to be en femme. Most weekends, two or three weeks a summer. Will you like that?" I asked when he had agreed to marry me.
"More than anything," said Terry.
"In the city you have your job so you can't really be who you like to be. Or, at least, not yet. But you'll be a country wife which will be fun for you and fun for me."
"Yes, Miss Cara," said Teri.
"After we're married you will not have to call me miss anymore," I said. "And in the country, you'll wear your pretty gaff panties rather than that nasty old cock cage."
Which was exactly what happened.
Teri has taken to the world of a 1950's housewife with a vengeance. She's always beautifully dressed, her hair is perfect and she is wonderfully obedient. She was, I must admit, a little taken aback when she discovered that I was going to give her the whole experience by having intercourse with her every Saturday night with a strap-on.
"Do I have to?" she asked?
"Of course you have to," I said. "But unlike those poor girls in the fifties with just the one cock, I have a number of dildos which will fit my harness. We'll start you off like a virgin with something small but hard and work your pretty back pussy up to big cocks."
Which is exactly what we did.
During the week, while Terry is wonderfully submissive and attentive, other than his panties and camisole and his cock cage, he is allowed to present as a slightly effeminate man. As soon as he comes home from work on Friday he showers, is let out of his cock cage, gaffed and then changes into his weekend attire.
Our neighbours in the country think we may be lesbians but we simply keep them guessing.
We've lived this way for a few years now. I am still a make-up artist and I still have a select cross dressing clientele. Terry is not in the least jealous. Even if he was, a good wife, and Teri is a very good wife, knows when to keep quiet.
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