How I finally went back to tranny escorting

(A true life account of an escorting episode that I indulged in recently as a provider)

crossdresser escort tranny escort real story

 

“You won’t, I know. You just get my hopes up and do nothing about it”, she said in half complaint. I was looking out through the glass at a rain-soaked airport tarmac while I spoke to my wife. The airplanes moving about looked blurry through the thousands of water droplets snaking their way down the glass wall.

“You never know…” I teased, but I knew she was right. I am a 30-year-old gender fluid person with a hobby for crossdressing. “Hobby” would be putting it lightly. Let’s say being femme and still androgynous is my way of living. At that moment, I was in smart business jeans, canvas shoes, a dinner jacket and v-neck gray t-shirt. But underneath the jeans were fishnets and comfortable mixed fabric panties.

Escorting is a fetish of mine. While I have been crossdressing for over seventeen years now, pleasing men, women, couples and everyone in between in return for benefits is more of a recent development. I don’t do it for the money. I have worked hard and smart to have a kind life and certainly don’t need the money. To put it straight, let’s just say hotels and cash turn me on – a lot. It’s the taboo that gives me the kicks.

Having said that, I have indulged in the kink “far too rarely” according to my wife (who knows, approves, and often instigates my crossdressing lifestyle). I have set my bars high, sometimes too high it would seem, as to whom I meet.

And then there is the mood;

While I practice a 24×7 form of femininity, being in the right frame of mind to meet a stranger and make out, that doesn’t happen too often.

I heard the announcement and people sitting around me started to make a line for the gate that would lead us to the evening flight back to India. I was beginning to sport a bit of a hardon in my panties and was immediately thankful that I was wearing jeans, it would have been rather tricky to hide the obvious bulge otherwise.

I sent the half-composed email which ended with these lines:

“My flight lands at 7:30. I should be at the hotel by 9:30. Meet me at the hotel lobby. I’ll take cash as decided and before we enter the room. See you soon!”

Love,
Isilyen”

I knew I could still back out, make up something like my flight was delayed or just the lame “something’s come up”. Somehow I knew, that wasn’t going to happen.

The flight was uneventful and exactly how I like it. I didn’t have a chatty co-passenger and I was blissfully lost in the music playing through my earphones. Singapore was a whirlwind trip and the tiredness was threatening to set in. “Not yet”, said something inside me, close to the midsection.

I went through the landing ritual quickly enough as I only had cabin baggage with me and soon found myself in my car. On trips less that last less than a week, I usually leave my car in the airport parking. Saves me the trouble of hailing down cabs and waiting for them in the crowd.

It was dark and interestingly, I found the parking bay where I had parked my car to be completely empty. Rather unusual for Bangalore airport. The duffle bag with the basic makeup (I am not someone who likes to sport a drag queen look) was in the luggage carrier at the back.

Taking a deep breath, I almost smiled. I could sense that familiar but rare feeling of someone else taking over me. That someone who’s sassy, sexy and a slut. I mouthed the word slut as I looked at myself in the mirror after a quick change.

Plain nude gloss on my lips, a face made clear with cleaning tissue and a simple base of non-sweating foundation. My hair (which is naturally long till just beyond the shoulders) until now in a bun, brushed and open, a sexy by comfortable bra underneath a plain white top (something I could pass by without attracting too much attention). I could smell the feminine perfume I just wore. These subtle efforts made the transformation quite remarkable and yet not easy to spot you spent some time around me or looked carefully.

The fact that I took off my t-shirt in that empty parking lot, put on my bra, wore the stuffing and the top, was enough to bring the slut out to the front. I was doing this, alright! I looked at the big masculine white beast I drove. I smiled at myself, looking into the large side-view mirror. Partly because the man side of me just loved the car and partly because, in my own eyes, I looked at least a bit hot.

A red neon light from somewhere nearby reflected off my face and torso. The jacket lay on top of the driver’s seat, I leaned against the car, folded my right knee up, lit a cigarette, and took a drag.

Right at that moment, I could have been hooker anywhere in the world. Could have been offered and picked up, and I wouldn’t have minded one bit.

The drive was as it always is in Bangalore – painful. As I drove into the drop-off zone, I was glad once again that I set my standards high. The gleaming entry of a 5-star hotel as always gave both a sense of safety and the sinful rush that only comes from luxury.

What happens rest, is best described with pictures. Do read through, I am sure you won’t mind it. The story flows through the pictures and their captions:

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In the elevator. Having my top filled out had made be quite nervous but the jacket helped. Over the years I have learned how to work my angles, so as far as I know, no one probably noticed. The doorkeeper did give me a look, though. However, it was more curious than anything else. He was naughty, though, gently but with all the intention, he slipped the jacket off just as we were entering the elevator. I loved how he didn’t try to grab by dick. As a girl, that’s the last thing that you want. Instead, he palmed me, like feeling for a pussy.

My man for the night was waiting close to the entrance, reading a magazine and sipping a drink of some kind. I liked the look. He was naughty, though, gently but with all the intention, he slipped the jacket off my shoulders just as we were entering the elevator. I loved how he didn’t try to grab by dick. As a girl, that’s the last thing that you want. Instead, he palmed me, like feeling for a feminine something.

 

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Inside the hotel room, a feeling of cash, cigarette smoke, a light drink and spread legs, that’s a mix that I can’t help but get aroused by.  I took off my boy clothes. I belong to a world of crossdressing where the focus is not a huge lot on the clothes (I know it defies the idea of “dressing”. But I believe it is more about dressing the gender, not so much the clothes).

The below couple of pictures is of us just getting a slow feel of our bodies before I excused myself to put on some of the basic necessities of crossdressing.

 

Then it was time for a quick shower and some “me” time as I “transformed” more appropriately. I always insist on some alone time when I meet a patron and don’t prefer to shower together (although that’s something that men have asked me a lot). Crossdressing is an illusion and a magician needs her prep-time.

 

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It’s my wife who had packed for me before I left. One of the many small things in our daily life that make it so endearing for both of us is that how casually erotic the whole thing is. She put in stockings, heels, lingerie and other girl things in a bag with as much “normalcy” as she made sure I did not forget the tie or the diary. I was so pleased that she had chosen this white stocking.
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And white lace panties to match. Much better than the boring dark coloured comfort-cuts that I normally wear during the day under man-clothes. I had what I needed to turn my man for the night happy.

 

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Him teasing me at that point. The top still on, I could feel his cock teasingly rub against my behind and every now and then against the tip of my tucked clit.

 

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I normally am very picky whom I kiss. It’s an art and I hate people who slobber around it. This was an exception and he was pretty good at it.

 

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Him going down on me – taking turns sucking on my clit and rimming me. I was desperate to feel his hardness in my mouth but he insisted on getting me as hungry as possible by first pleasuring me.

 

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Well, he knew what he was doing – I had to take him all the way down my throat in my very first go. A good slut pleasures her man through and through. Especially when that slut is being paid to do so.

 

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I must say, that if I had to choose my favourite thing to do to a man, it had to be giving him the most divine blowjob he had every received in his life. A blowjob that he would go on compare to when he gets sucked by his wife, girlfriend or boyfriend and wished it was me instead.

 

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Time to ride my man for the night but not let him in yet, tease him, just the way he teased me. That’s me grinding against his hard manhood, begging to get inside me and almost doing so many times as it rubbed so close to my entrance.

 

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There’s no better feeling than making your man cum by rubbing your ass on his cock. Okay, perhaps making him cum in your mouth is a headier thing but to feel his precum coat my boy-pussy, to the tip almost popping inside with each grind and to feel his hands reach up and behind, unclasp my bra and feel my breasts that I have worked so hard to get and not be flat-chested, was amazing beyond words.

 

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A little rest but the night that was just only beginning to get interesting. His now softer cock pressing against my thigh, me moving my leg up and down just a bit to stroke it, his hand cupping my clit-cock and fingering my boy-pussy.

 

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As I mentioned somewhere above, crossdressing is all about the illusion it is – and for me, the illusion is carried out more with my body than with my clothes. His thumb teasing my entrance while I hide the obvious from the camera.

 

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I was hoping he wasn’t going to stay soft for too long and I wasn’t disappointed. Still, a bit of teasing was on the cards. That’s me riding him again, just not letting him in yet (I dressed meanwhile as we shared a couple of smokes and a few drinks before I got to the mischief again. The B&W filter somehow inverted the colours).

 

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By now, I needed it as much as he did… Beds are over rated anyway and we needed the right angle, as I am a tall girl. Furthermore, as much as I like being taken missionary, sometimes, a slut needs to be fucked from the behind.

I left a little more than an hour or so later. I didn’t shower, as my wife loves the evidence.

Untill next time,

Love,
Isilyen.