My first tranny/cross-dresser client

[jadeofsydney]

This client surprised me – pleasantly! I guess it’s true, you can’t judge a book by its cover. He was a mid 30’s caucasian, very tall and lean, dressed in business attire.

We disappeared upstairs for an hour. When I left him to have a shower he asked me if I minded if he “dressed up” and if I could give him 10 mins to get ready. I said ok. Now I’m intrigued......what does he have in the sports bag?

Now this is where things get interesting. I re-enter the room and my client is dressed in black fishnet stockings, heels, black mini skirt, yellow crop top and brunette wig. He is standing in front of the mirror applying make-up – pretty terribly. I asked if he wanted help. He said yes, so I grabbed my make-up case and fixed his lippy, added some blush and eye colour.

Transformation complete, he asked if I could now call him/her “Natasha”. Hahahaha

My first task was to take some pics on his/her iPhone. Natasha posed as I snapped away. I got some good shots. I tried to take this seriously but really struggled to not crack up laughing. I don’t think she was impressed.

Next she asked me to lie down on the bed. Natasha then proceeded with DATY. I have to admit it was pretty good – she brought me to orgasm pretty quickly. Not the best oral I’ve had, but a good 8 or 9/10.

Time for me to get to work. Natasha pulled some nipple clamps out of her bag and helped me to attach them. I gently tugged on the chain with one hand while I stroked her cock with my other hand. She was still fully clothed, I just moved her black satin g-string to the side so I could do a hand job. I don’t think I’ve ever seen someone get so turned on by “nipple play”. She was rock hard!

It was now bj time. She liked a long, slow suck with plenty of attention to the head and a light ball tickle. I continued to tug the nipple chain as I sucked.

She asked me to finish her off with a hand job. She removed her g-string so I could get full access. I oiled her up and she responded well. It wasn’t long before she came.

There was no sex in this booking.

I gave her my make-up remover to get rid of all traces of “Natasha”. Probably not a good idea to be getting on a train with stained red lips. Natasha was now back to being Mr Businessman.

Is it weird to admit I thoroughly enjoyed this booking? Actually, I loved it! Definitely one of the most memorable sessions of 2014.

[cmk76]

...while I stroked her cock with my other hand...

Hmmm... interesting reference...
Unique read though... thanks for sharing...!

[timtam]

That's strange!!! A great report jade!

[max_power]

Right on there....never judge a book by its cover

[Sextus]

Hmm, I'm not too up to speed on the ins and outs of this. This guy was a cross dresser right? Not a trannie. And cross dressers are always straight - they're heteros right? Because if they aren't straight then that makes them trannies - right?

This guy is so into females, he's so super straight that slipping into their clothes and make up makes him feel much closer to them. (Although usually a dick inside is sufficient for that.)

[jadeofsydney]

Tranny/trannie can mean transvestite (cross-dresser), transsexual or transgender.

I'm guessing he was straight. My "gaydar" is usually pretty accurate.

[Mr. Who]

Fun read. Thanks for sharing!

[rooter]

So that's what Tony Abbott gets up to when parliament is not sitting ...