Originally Posted by gloves
The only way to know for sure is to take the plunge and give it a go – I am sure you wont regret it.
To help you make the decision, I will tell you a little (or a lot) about my first time. I was in Singapore in January 2010 and I had been fascinated by ladyboys for a couple of years at that time. I had mistakenly downloaded some ladyboy porn a couple of years earlier, but I loved it – I tugged my wanger incessantly, and found myself downloading more and more ladyboy porn. Anyway, I arrive in Singapore, I am staying near Orchard Towers and I have done my research – I know that Crazy Horse and Club Romeo is where you will find these fascinating creatures. It is a Saturday night and I make my way to OT but I don’t have the balls to make my way in – I lost my nerve. I retreat to my hotel and just happen to share a lift with a very mediocre, mid 50s, fat white guy and he has two gorgeous Thai transsexuals dripping off him. I think if he can do it, so can I. So I head straight back to Crazy Horse, cruise on in, and then the magic happens.
They are all over you! Within seconds, a gorgeous, tall Thai lass with big boobs approaches me and asks me if I am into ladyboys. I nervously say yes and we chat, but I want to see what else is on offer – I am in no hurry, and she politely excuses herself and moves on without fuss. Within seconds, a much more elegant, slender lady collars me and we start talking. She is Thai and her name is Eran. She is approximately 170cm, slender, beautiful face, smart bob hairstyle with a blonde tinge and a lovely, friendly person. She lets me know immediately that she is a ladyboy, otherwise I wouldn’t have known (100% passable) and we chat. I want to be topped and she assures me that she has a cock and that she gets hard, so we agree to a price (I think it was S$250 but it was a long time ago). We walk back to my hotel and talk along the way - she is delightful - a little shy but very sassy. Then we are back in the hotel and she knows it is my first time. She undresses to reveal a perfect set of natural looking tits, and then the “pièce de résistance” – she peels down her lacey undies, bends her knees slightly, and out flops a beautiful, long, uncircumcised cock! This was probably the single most arousing sight I have ever seen. And then she said “You can do anything to me”. We jump into the shower and wash each other’s arses and tug each other’s cocks. She also liked to french. We are both already rock hard and rub our cocks up against each other’s – I am at the very height of sexual arousal.
We dry each other off then Eran jumps on the bed and spreads her legs. She demands that I suck her cock. I think “nuff said” and go to town. It was my first time to suck a cock but you wouldn’t know it – I was like a duck to water, and she fucked my tonsils for about 15 minutes. She had a beautiful slender, bent cock and as hard as steel. She occasionally tukey slapped me with it and I also licked her balls and arse (much nicer than you imagine). We took in turns to suck cock and also 69ed each other – it is a magic feeling to have a ladyboy lower her scrotum into your mouth.
Then the moment of truth – Eran wanted to fuck me. I said okay and she put me in the missionary position with a pillow under the small of my back and slowly and gently thrust her hard bent cock into my rectum. The honest truth is that I didn’t like it at first – it felt like I needed to to do a dirty great shit. But once she got into her rythym, and I realised that I wasn’t going to shit myself (it was just her hard cock up my arse), it was pure exhilaration – I let out a weird primal groan as she thrust her way into me up to her balls.
Then I fucked her arse – Eran stood up with one leg on the floor and the other up on the bed and guided my cock into her shitter. What a feeling! What a wonderful tight arse she had and I just banged away, my hands occupied with either her perfect breasts or her swinging cock. Eventually, after all sorts of different positions and activities , we masturbated on the bed together. We ejaculated simlutaneously, Eran dropping her load into my chest hair. We had a quiet smoke on the bed, then I guess she went back to Crazy Horse and waited for the next lucky punter.
Ever since that day, I am hooked – I crave ladyboy cock in my my mouth and up my arse, preferably at the same time. I have been withn all sorts of ladyboys since – Filipino, Malayan, Polynesian, and other Thais, from the high-class ladyboys who travel around the world and earn fabulous amounts of money, to the cheap and cheerful in the back alleys of Geylang. Some offer better service than others but they have all been extaordinary sexual experiences – they know what guys want when it comes to sex. And the sensation of involuntarily shooting your load while a ladyboy is drilling your arse is something that every guy should experience. But for me, the Thais do it best – they have been sweet-natured and I just loved those hard, bent, uncircumcised cocks. But that is my personal preference.
I recently read on this forum that a brother was told by a ladyboy “once you start playing with us, you will be addicted forever”. So true. Does that make me gay? Is that why you are hesitant? That is a whole new thread and I wont delve into it here. But the moral of my whole (long) story is that a good ladyboy can take you to a level of sexual ecstacy that you never dreamed possible.
If the opportunity presents, just do it! If there is a perceived stigma of having sex with someone who was born a man, just cast it aside – don’t deprive yourself of a wonderful sexual experience. And just remember, there are millions of other guys who feel the same way you do now. Some will act on the urge, others will be destined to a life of wanking alone in a dark room in front of a computer screen.
Which one are you?
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