My First Ladyboy


At 27 I reckoned I had the best job in the world. Twelve months ago I'd been appointed by the London-based international group I'd joined some five years before, to monitor the performance of our agents throughout the Far East from South Korea down to Indonesia and across to Thailand. No doubt one of the deciding factors in my appointment was that I was unattached.

A great deal of travelling was involved which I loved. I also enjoyed the first class hotels I stayed at, the wonderful variety of food and of course the company of the readily available women in many parts of the region.

One of my favourite countries was Thailand which was just as well as our agent there was causing us lots of problems which required frequent and on occasions, prolonged visits.

Early on I'd linked up with a resident pal, Ian, about my own age, who introduced me to numerous bars, massage parlours and other night spots in and around Bangkok.

One night Ian said he'd take me to a special bar where there were usually some interesting girls to be found. On arrival Ian introduced me to a dark-headed beauty with lightly tanned skin and a very ample bosom which she did nothing to conceal. I was immediately aroused, the more so when she spoke in a rather deep sexy voice.

After just one drink I suggested we move somewhere more private. She agreed and suggested we take a taxi to her nearby apartment.

Tam's apartment turned out to be one large room with a large bed, a couple of chairs and a small bathroom with a shower, a basin and a toilet.

Tam wasted little time in pulling me to her and kissing me open mouthed and passionately. I ground my full erection into her belly which caused Tam to say 'That feels just about my size darling. I'd love to feel it deep inside me but I've got my period. Don't worry though. I'm going to give you a blow job unlike anything you've ever had before.'

Now although I prefer to fuck I'm quite partial to a good blow job so raised no objection when she unbuckled my pants, unzipped me and pulled both my trousers and underpants off before getting down on her knees and taking my aching tool into her mouth.

'Play with my tits' Tam breathed sexily while licking the tender underside of my cock before once again gobbling it down deep into her mouth.

I pushed down Tam's blouse and took hold of two hard mounds of flesh which I squeezed and stroked while continuing to enjoy the ministrations of Tam's mouth and tongue on my eager cock. Despite my preoccupation though I took note of her unusually small nipples.

Tam pulled off to draw breath and as she returned to her work she said "Fuck my face darling.'

There was only one way I could react to that and that was to push deep into Tam's mouth. I'm a bit better than average length, a bit fatter than most but Tam accepted everything I had to offer.

Tam was very obviously an experienced cock-sucker and I was delighted when she angled her head to take my knob into her throat. This was turning out to be one hell of a blow-job and I knew it wouldn't be long before I blew a load down her throat.

Reaching up under my shirt with one hand Tam began pinching my nipple while with the other she inserted a finger in my arse hole. All this proved more than I could take and with one final thrust I exploded in her mouth jet after jet of cum spewing into her oral cavity.

Tam waited until the flow stopped and then gently pulled off licking the fuck-cream from my shaft. Then she got to her feet and pressing her lips to mine dribbled my cum into my mouth. This was some woman.

'Let's lie on the bed for a while' suggested Tam and we both moved across the room and made ourselves comfortable, Tam spooning her back into me.

'Let me do something for you darling.' I asked. Tam remained silent. 'Let me stroke you clit and bring you off.' Again no response.

I thought Tam had gone to sleep but then she said quietly 'If I tell you something will you promise not to get mad?'

'You can tell me anything you like and I promise I won't get mad.'

'Give me you hand.'

I reached across and Tam guided my hand under her skirt and then placed it at the top of her panties. This I took as an invitation to slide my hand down inside. I did just that seeking her clit which I then intended to stroke hoping to bring Tam off.

My hand groped and came to rest on what I first thought was an unusually large clit but I quickly realised was in fact a smallish semi-stiff cock.

My first thought was to pull my hand away but something about the appendage I was now holding felt so good that I left it there.

'You're not mad? Asked Tam.

'No not mad. Just very surprised. I've read about ladyboys but you're the first I've come in contact with.'

'Do you like?'

'I haven't held another guy's cock since I was a boy but with you it's different. To me you're a very desirable woman and the fact that you've got a bigger clit than I expected doesn't change that. Yes I like but the absence of a hole is a disappointment I have to admit.'

'I do have another hole darling and you're welcome to use that. In fact I'd love to feel you deep in my boy-pussy.'

'I've never fucked anyone, boy or girl, in the arse though I have to admit I've thought about it.'

'Then why don't you try? Just pretend you're fucking a woman with a very tight fuck-hole. I'm sure you'd enjoy it.'

'OK. But first let me look at your cock. I want to understand everything about you.'

'Let's get undressed' said Tam. I agreed and stripped the rest of my clothes off while Tam shed her panties, skirt and blouse. She lay beside me spread out and naked.

I moved down and took in something I'd never expected to see. Tam had a bush of fine black hair in the midst of which lay a small brown penis, about two inches long with a darker foreskin covering her cock-head. I peeled it back to reveal a pink knob. I felt for her balls but found nothing or close to nothing.

Without thought I leaned forward and sucked the full length of Tam's cock into my mouth teasing back the hood and licking the soft sensitive spot under the head.

'That's so good darling. It gives me big warm feelings.'

'Can I make you cum.'

'No my balls are almost gone now because of the female hormones I take to make me more feminine. My tits of course are implants but the hormones help to keep them firm. My nipples are all mine. I only wish they were bigger. Now I cum more like a woman – inside. It's especially good when I'm being fucked in my boy-pussy. Are you ready for me? Let me feel your cock. Yes, it's hard again. Get on top of me.'

I did as Tam instructed though I was surprised she didn't get on her hands and knees which I thought of as the usual way to arse-fuck.

Tam reached behind her and took a pillow which she placed under the small of her back and then pulled back her legs exposing her dark brown wrinkled hole surrounded by matted fine black hair.

'Lick it darling. Make it wet. Don't worry, it's clean. Get it ready for your cock.'

I have to admit I was somewhat reluctant to put my lips to Tam's arse hole or boy-pussy as she preferred to call it. Much to my surprise however the taste was by no means objectionable and I quickly fell into a rhythm of licking and sucking.

By her murmurings it was clear Tam was greatly enjoying my tongue and my lips and as I pulled away I saw that her hole was slightly open, invitingly so.

I moved up between her legs and Tam grabbed my stiff shaft rubbing the head around her wet hole. I was now leaking pre-cum freely and was getting increasingly aroused.

Tam stopped her movements and placed my knob at her entrance.

'Push darling. Slide into me.'

Despite my cock being absolutely rigid, I felt resistance, so unlike what I was used to in entering a well lubricated cunt. Then I felt Tam's arse hole push out and the head of my cock slipped into a very tight space.

'You're in darling. Just hold it a second and then push in slowly.'

I did as instructed and very soon found my cock firmly embedded in the tightest fuck tunnel I'd ever known. The feeling was indescribably good.'

'Now fuck me darling. Fuck me as a woman. Make me cum inside as you shoot your love juice deep inside me.'

I needed no further encouragement to begin a steady pounding of Tam's arse her legs locked behind me urging me on.

Happily, the wonderful blow job I'd enjoyed just a half an hour before had taken the edge of my appetite and I luxuriated in the thrill of a long steady fuck embedded in a tight, hot hole. With Tam kissing me passionately I forgot completely that I was fucking a guy's arsehole. As far as my cock was concerned, and my head for that matter, I was fucking a highly desirable woman.

As the saying goes, all good things must come to an end and I was not about to prove this old adage wrong. Before long I began to feel the ache in my balls start to overtake the pleasure my cock was experiencing and I knew that I would not be able to hold back the flow of fuck-cream for long. I began to pound Tam's hole faster as she encouraged me with her words and her body. Reaching down I found her little cock was stiff and on pealing back the hood found it quiet wet. At least her prostate was still working.

With one final drive I pushed into Tam's bowels as far as I could reach and dumped jet after jet of cum deep inside her. I held my hard cock inside her relishing the gentle squeezing of her anal muscles.

'Jesus Tam, that was the most fantastic fuck I've ever had.'

'I'm so glad darling. Very good for me too' said Tam. 'You know I had this strong feeling for you when you walked into the bar. I wanted very much to be with you but was scared to tell you I wasn't totally female in case I frightened you away. Sorry darling. But after you kissed me and I sucked you off I felt very close to you and decided to take a chance.'

'Darling Tam you're the first ladyboy I've had anything to do with. I'd heard about them but never had any thoughts of being with one. Now I know better and I promise you'll see me every time I visit Bangkok in future and I'll do my best to make that as often as I can.'

That was the beginning of quite a long association with Tam who proved to be a wonderful lover and very good friend during my frequent visits to Bangkok. After our first coupling she refused to take any money from me but of course I bought her many gifts.

Although Tam was a working 'girl' I always fucked her bareback. Mind you this was before HIV and AIDS came on the scene. It would be a very different story today.

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