My First Ladyboy Experience

I'm a typical man, big hairy and rough on the edges.

For as long as I have had internet access I've always been drawn to watching shemale/ladyboy porn, just the sight of such magnificent female bodies always ignited a flame in my crotch area, I had masturbated to these clips thousands of times and I still do to this day. That was as far as that went.

I relocated to Thailand for work and quickly fell for the Asian beauty and had a string of decent relationships.

But as I was single and it was a Saturday morning alone in bed and I was scouting the social apps hoping to find some fun.

Got to chatting to this very sexy Thai called Pon and we chatted and she said she is a massage therapist and would I like a massage, in my mind it was just a Thai massage to destress after a busy week so I got showered and drive to her apartment, knocked in the door and she greeted me with a very friendly Thai wai 🙏🏻 And invited me inside. The room had a nice smell of incense and some candles were lit and she asked me To lay on the bed,

I got undressed but kept my boxers on and settled down for a rigorous massage. She had strong firm hands and worked every muscle on my back making my spine click and clack like Rice Krispies, when she got up my lower back her hand would occasionally work a little lower and then back up,

I would get a tingling arousing sensation and then I nothing, she kept doing this and I was considering asking her if she offered happy endings but I assumed this massage was above board and I was to polite to ask her.

The lower she got with the massage the more the hands would slightly glide on a sensual part and my cock was starting to get very hard, I'm still laying on my stomach with my boxers on so I can still conceal the hard erect cock.

She carries on and then asks me to turn around and lay on my back, I'm hesitant at first as she will see my erect cock and might be offended,

But I oblige and turn and her eyes go big and she cracks a sly smile that I'll never ever forget . She suggests I take off my shorts and be more comfortable. Now I'm rock hard and dripping pre cum like a leaky tap.

She is still fully clothed in her massage uniform at this point and I ask her to also take off her clothes, she removes the top but is hesitant to remove the trousers, I am staring at the most pert round boobs and reach up to fondle them and she doesn't stop me so I carry on. All this time she is still massaging my front but not paying much attention to my cock.

I can feel the pre cum dripping and my cock throbbing.

I reach out and I'm hoping to finger her pussy at least but she keeps blocking me. I am getting more sexually aroused but agitated and she can sense that and laughs at me.

She stops and gets off the bed and closes the curtains and turns the lights off leaving just the candles to light the room.

Turns away from me and removes her trousers and I get a good view of her ass. She gets back on the bed and starts playing with my cock and licking the pre cum off my tip and I reach for her Pussy and this time she allows me to touch and as soon as my hand touched it I got a big fright and I was touching a very hard cock.

I recoiled at first and a million thoughts ran through my mind!!

What the hell is this?

What am I doing?

I got touched by a man am I gay?

I'm in two minds to jump up and run but my body is so horny and she has worked me up to such a point I relax and try adjust to my situation.

She realises my shock and stops touching me and replies that she is sorry and she should have told me in the beginning.

I'm always open to trying most things and I'm thinking she isn't a man in the male sense so let's go for it.

I touch her hard cock and it's soft to the touch and so warm and she asks if I would like to suck it and I put it in my mouth and lick the way I like to licked and her breathing is getting deeper so I assume I'm doing it right.

She is stroking my hard cock and running a finger over my virgin ass and I'm losing all abilities to say no and just let her take control of the situation.

She licks my ass and ring and I've never ever experienced an inner fire like that before and I'm moaning with my new found pleasure.

She inserts a finger and slowly teases my hole and I'm moaning a little more.

She asks if I want to try her cock inside me, I have zero desire to say no, I'm completely lost in the moment and so hot with passion. She lubricates my hole and her erect cock and puts the head against my hole, it hurts like hell at first but she is calm and gentle and slowly eases it into me, I'm on my stomach and my ass is raised and she is balls deep inside me and slowly but gently she starts pumping my ass, it hurts for a while then suddenly I'm feeling comfortable and enjoying it.

Her hands are gripping my hips and her breathing is getting heavier and more rapid and I'm face down on the bed moaning and enjoying this.

She says she is going to cum soon and pumps into me a few more times then releases what I can describe as a flow of lava into my ass and I can feel it flowing inside me and some of it leaking out and oozing onto my balls and the bed sheets.

I'm still on my knees with a bum full of cum and she pulls out and starts licking my ass and eating her own cum, it was the hottest thing I'd ever experienced in my life. My anus muscles were tender from been fucked and her tongue licking up her juices added to the sensations.

I needed to cum soon and she put my cock into her mouth and gave me a very wet and rapid deep throat blow job and I did not take long before I exploded.

I showered and drove home and then guilt and Shame set in.

What had I just done and I've not used a condom and will anybody find out.

As much as I tried to convince myself it was a one time only thing my body yearned for it.

We both had tests done and both came out clear and we decided to be an item.

As our friendship grew so did our passion. I would completely open up my body to her and let her do what she does best.

I sadly don't live in Thailand anymore but we still remain good friends to this day.