Penny - A Thai Ladyboy Love Tale

One day, actually not so long ago, just before the pandemic hit, I found myself in Bangkok and as usual, I thought I would explore the nightlife.

I went to Pat Pong, as I wanted to get a couple of t-shirts as it's cheaper to buy new than have the overpriced services in the Hotels ruin everything.

I sat in a bar, unfortunately there were some loud Aussies and Brits there drinking heavily, so I sat in the corner and watched as the local girls circled the assembled drinkers. Some girls joined them for overpriced shots, and false bonhomie. I went to the gents, and came back to see a rather shy girl at my table,

I sat down, she was so apologetic as she assumed the table was free, to be fair, my bottle of Singha was nearly finished, so I understood her mistake.

As it was a big table in a booth, I said I was happy for her to sit there, and out of courtesy I offered her a drink. She went for a Carabao, a local energy drink with no alcohol, and she sat there distracted. It wasn't my first trip to Thailand, but it seemed it was her first trip to Bangkok, as she was from a city around 50 to 60 miles away called Ayutthaya, which as many people know is the old capital of Thailand when it was known under a different name- Siam.

We chatted, I was getting tired, and she told me she had arranged to meet a girlfriend at that bar but she hadn't showed up. It was only then that I realised she had a wheelie case next to her, so the story seemed true.

I paid the small bill, and stood up to leave. Penny, the name she told me was hers, all of a sudden looked very vulnerable as the boisterous drunks were leering at her, and she clearly was scared. I asked if I could get a taxi and drop her somewhere, she nodded and we left. I let her talk to the cab driver, as my hotel was some way away and I assumed she was giving directions. I dozed, and woke up at the grand entrance to my hotel the Sheraton, in a tatty side street, but at least my room overlooked the river I asked Penny if the cab was taken her onwards, but the driver had already popped the boot so I guess she was staying near here, as there were lots of guesthouses and small hotels.

She told me that here friend, who she still couldn't raise on the phone had said that she could stay with her for a few days until she got established, which I took to meaning to finding money and work.

She started to tear up, so I said she could come in with me- I could stand her a room for one or two nights while she tried to sort herself out. I looked at her, tiny and vulnerable and she nodded shyly.

We went into the hotel, there is a huge lobby area and there was an enormous crowd of Korean conference attendee's shouting, leering and drinking heavily.

We walked to the from desk, and I made the request for a room, and she got her ID out for the hotel.

The concierge told me that there were no free rooms, but as my room was a large bedroom suite, they said the lady could stay with me as long as I paid for her breakfast, and a small surcharge and that the hotel had a sofa bed which they would gladly make up. Penny agreed, and housekeeping were good to their word and did just that.

I could see Penny had no idea how to react to the luxury of this hotel and the river view from two windows in the suite, and she was quiet.

She thanked me, stood on the sofa on tiptoes and kissed me on the cheek to thank me for being a gentleman.

I offered her to use the bathroom first, which she accepted, opening her suitcase and removing a wash bag and some nightclothes.

She came out of the bathroom, refreshingly free of make up, and slipped under the covers wearing a t-shirt and shorts. I went to the bathroom, took a shower, and out of respect I left wearing one of the oversized towelling robes, before slipping into bed. I didn't feel threatened, but did think what on earth have I done! More to the point what had she done, a slight Asian girl going to a strange foreigners room.

I dozed of to the sound of light breathing from Penny and the gentle rush from the air-conditioning unit.

At some point in the night, Penny crept into bed with me, and laid asleep, head on my chest, her long black hair fanning out on me. I woke up, saw this and I didn't disturb her but I did put my arm around her as she felt cold, and she seemed to shrink into me breathing softly. I had no clothes on, but she either didn't notice or didn't mind.

Morning broke, I awoke alone, but could hear the shower running, and when I opened my eyes for a second time, she was sitting cross legged on the coach, wearing a white t shirt, and cut off denim shorts, which were so short the pockets hung down below the cut off hem.

She was focused on her phone trying to get hold of her friend with no luck.

I asked her to pass my robe and I got up without exposing my semi hard 8-inch cock to her.

I showered, shaved and dressed in the dressing area of the suite, and as it was Saturday morning I had no meetings to attend.

Penny told me her friend was not answering and that she was wondering what to do, where to go and even if she should go home to her family a few miles north of Ayutthaya.

I was hungry.

I dressed in shorts and a polo shirt I asked if she wanted some breakfast, we had only chatted briefly in the bar, it was noisy, and I was certain how much she understood. As it turned out over breakfast she told me that she was a nearly qualified English teacher, but had come to Bangkok to work in a bar with her friend to raise the final amount, and the exam fees as her families farm was barely producing enough for them to live on.

She had no luck in finding here friend, but I said she could stay with me for a few days until I left Bangkok, but that I had some meetings Monday and Tuesday.

She was cute, but I am a man in my late 50's and figured she would want and deserve someone closer to her age, which I didn't know but was confirmed later that she was 22.

We toured Bangkok, I have been there before so we did the river cruise and stopped at various temples on the way.

She had very little money on her so I told her to put 5,000 Bhatt in her purse in case we got separated or if she needed personal items, or whatever. She refused, but took 2,500 when I insisted- for safety reasons.

We walked around the Temple area, and I wanted to take her to the Kings Palace, but it was mid afternoon, so we caught the riverboat back to the Hotel.

She went into the chemist at the terminal, I waited outside, and then we went to the hotel.

In the elevator for the first time she stood close to me, and when we reached the room, she locked and bolted the door and hugged me for being so nice, and such a gentleman.

To be honest she was an incredibly sexy girl, not so small budding breasts and lovely legs. She was slim and pretty too, with a sweet nature. Of course I wanted to fuck her senseless, and I was imagining a tight shaved pussy, and a tiny arse to play with, but I could sense she was in a bad place, and I didn't want to abuse her trust.

I had watched her all day, she seemed so nice almost innocent, but I wasn't a creep and I wanted to treat her with respect.

I made us coffee in the room, while she went to the bathroom, grabbing some things from her bag.

She called me from the bathroom, it was steamy, and she asked me to pass something from her bag. I did look as I am a man, and I could see rigid brown nipples poking through the bubbles in the huge corner bath.

I passed her something to tie her hair back with, she asked me to join her in the bath, which to be honest I was hoping for but I felt it had to come from her first I disrobed in seconds, my hardening large cut cock swinging around as I lowered myself into the tub.

She shuffled up, sat on my lap, and kissed me long and hard, thanking me for being ' one of the good guys' -- luckily she wasn't a mind reader!

We kissed deeply, she shuffled up and put one arm around my neck, and she guided my hand to her breasts with the other. I didn't need a second invitation, so I grabbed her boobs, they felt larger than I was expecting but it was her nipples so hard I reckon you could slice bread use them as a weapon!

She kissed me further, reached down and grabbed my cock, and withdrew her hand gasping.

"Too big "

Two words every man likes to hear. She looked thoughtful, and seemed about to say something, and moved my hand off her lovely soft (but small) tits and moved it down to her pussy.

Which wasn't there.

Instead, she had a small cock. I wasn't altogether surprised, as she never spoke about kids, she was silent about her family, her friends and her thoughts in general, Also women have children younger in some Asian countries and she never mentioned kids, her nipples were sharp, and her boobs were high-thereby not showing the effects of breastfeeding which most Asian mothers do for a long time.

Also I had an inkling she was Trans, spending so much time travelling I had a 6th sense for these things. I was secretly delighted.

She stood up, it was erect and about 4 inches, thin and totally shaved.

My ex GF was trans, so I opened my lips and sucked her into my waiting mouth. It was an instant reaction, and probably not the reaction she was expecting.

No words were spoken, she seemed calm, a little shocked when I first ignored the cock, and took it into my mouth, but now she was running her fingers through my hair, and was lost in the moment until she climaxed.

She withdrew, horrified as she didn't warn me. I pulled her face down, squatted down so we were level and kissed her and held her tightly.

Perhaps I should explain. My personal preference is to have relationships with Trans ladies who I consider as women. It doesn't matter to me what is between your legs, as this doesn't, (in my humble opinion) define your gender.

Penny hugged me so hard, I could barely breath. We got out of the rapidly cooling water and dried ourselves off in the huge bathroom. I offered her towelling robe, and we went and sat down in the lounge area together.

She told me her life story, her willingness to sacrifice her body to study and ensure she received a decent qualification to support her family. Her friend had been a 'bar girl' for years, also Trance, and Penny was persuaded by circumstances to try and make some money doing that too.

Effectively, apart from some fumbling around at her college, she was to all intents and purposes a virgin. She had been penetrated one time by an Uncle- but it lasted a few seconds, as he was small and she managed to push him away spilling his seed all over the floor of their family home.

The evening went into night, and we were both hungry. I took her to a seafood place I have previously visited, where we ate fresh crab and rice.

On returning to the Suite, she excused herself and went to the bathroom. She came out, fully made up, and I could see she had stockings or tights on. She told me to go and freshen up, which I did popping a small blue pill in the process.

I took a shower as it was sticky out there,and to give the pill a chance to work, emerging, in just my robe, which was gaping as my 8 inch hard cock was poking through the opening.

Penny opened her robe, and was a vision in a black lacy outfit, stockings, suspenders and a push up bra, with no panties. She beckoned me to the bed; I threw my robe over a chair, and joined her.

We kissed deeply, she seemed overcome with passion, and she pushed me back on the bed, opening her lipstick-covered mouth, and sucking my cock. I manoeuvred her round so she lay on top of me and I could lick her balls and arse. She squirmed and pushed her arse down onto my tongue, whilst she struggled to take my cock into her mouth.

We both came up for air, and then moved to lie down next to each other, sucking each other. She put a finger in my arse, I did the same and we climaxed together within seconds of each other. I hadn't cum for a while, so she got a real mouthful. We were both sticky, and gazed into each other's eyes with pure lust. I was still hard from the blue pill, so I lay her on her back, her cock and my cock still leaking and I sucked her big brown nipples, which sent her thrashing about on the bed like a captured fish.

I kissed all the way down and spread her legs licking the inside of her thighs. She told me to stop and pass her bag, which I did and she extricated a tube of lube, which may have been what her friend recommended her to buy!

She worked it inside her, and over me, probably too much, but I am big and she had only taken one cock in her some time ago, so she smiled, said she was ready, and I eased my cock past her outer ring, stopping whilst she breathed deeply and relaxed, and slowly and surely I managed to penetrate her.

To be honest, it is lucky I had already cum otherwise it would have been over too quickly, and she was tight, slippery and was making some sexy noises and gasps.

I buried my cock completely inside her, she had her eyes closed and was squeezing her nipples, having divested herself from her black lacy pushup bra and I started to move slowly in and out, and her young cock started to get hard again and leak as I ploughed her prostate with my huge thick cut cock. We remained in this position so I could see her face as I fucked her over and over again, She gasped,yelped and tightened her sphincter.

I looked down, and she had cum all over her chest, some drops even hitting her chin and she in a wonderful way smiled as I emptied my load inside her. I figured she was safe, as was I, and she couldn't get pregnant so I filled her tight hole with hot cum.

I softened inside her and as I withdrew, and glob of cum left her gaping reddened hole and landed on the sheets.

I lay back, sated, and she undressed completely and went to the bathroom. I could hear the shower running, so I joined her and we kissed and stroked each other under the warm jets, I really wanted to fuck her again, but I didn't have the energy!

The next day I was woken up by warm lips enveloping my cock, followed by a shifting as she straddled me and slowly sank down on my shaft, until she was impaled totally. She moved up and down, in her own world, and started leaking before she climaxed so hard, it hit me in the face! I can't usually cum that way, except if the girl is very experienced, which Penny is not, so I extricated myself, told her to get on her knees, and as she was slick and recently lubed before I woke up, I managed to enter her in one smooth thrust, and powerfully fucked her till I emptied my morning load inside her. She turned round as I climaxed and told me she loved me.

Asian girls do this a lot on the first / second date!

I filled her arse with hot cum, and as I withdrew, so much of it poured out as her arse was gaping open that she had to put her hand there and run to the bathroom, juice dripping through her fingers. I was impressed with myself!

I will never forget that sight as long as I live!

I went to the bathroom, she was squatting over the bidet with her back to me and the cum was still dripping out. Finally her arsehole closed and we ran a bath together, having fun soaping each other, teasing, kissing and relaxing.

Neither of us was hungry, so we grabbed a coffee and took a taxi to the Kings Palace, which is stunning, and then I took her shopping.

Finally her friend phoned demanding she turn up at 18.00 at a sleazy bar near to Nana Plaza.

She went quiet, it's like a dream had finished, and her bubble had burst. Her friend was also demanding her fare and a 'fee' for finding her work.

Penny was upset and asked me how long I was in Bangkok for.

I looked at her innocent little face with those sultry brown eyes and I realised that I didn't want other men pawing her and disrespecting her, and I said I would repay her friend, but she refused and said she came here to finish paying for her education, which was around £1,800. and that she would see it though, but would be grateful if she i allowed her to use some of the money I gave her and a little more to repay her friend.

At that moment, as I most likely wasn't returning to Bangkok for a while I took the decision to change someone's life, and save her from a life of sleaze.

I offered to pay for her to complete her education and of course to replay her friend in full with a few hundred Bhatt on top.

This was after a long afternoon arguing, she finally relented, and I transferred the funds directly to the school and her friend.

We were back in the hotel by now, and she was quiet, and spent a long time in the bathroom -- longer than usual.

I was already ready, showered, different polo shirt and chinos, but she emerged with her beautiful made up face, a black and gold lace trimmed dress that I had purchased for her, heels and she looked like a model. She was wearing a new push up bra to enhance her cleavage, but it was not on show like a western girl, it was hidden by a piece of sheer fabric, hiding hidden treasures for my eyes only- hopefully.

We went out to another American chain hotel, and dined like royalty on a terrace on the banks of the muddy river.

All the way there and back in the hotel van, she was all over me, I had awakened a sex goddess.

She had her hand down my chinos stroking and squeezing me there and back, In turn, I was teasing her so her dress tented as she didn't tuck correctly.

I had to have this girl again with some immediacy but i wanted to extend our evening, so after dinner we went to a quiet bar I had found on a previous trip with dark booths, and a mellow vibe, and she sat next to me, before sitting astride me her long hair covering our heads as she ground her crotch into mine.

She then left me hard and oozing and vanished to the ladies. I loved the confidence she now had!

Unbeknown to me she had removed her panties and lubed her arse.

She returned, sat astride me facing the room, her dress covering us.

She unzipped me, loosened my waistband, and tugged my chinos down to my knees, reached behind and inserted my wet cock inside her tight arsehole. She sat down and took my full length. Our drinks arrived, and she was very cool as she took them from the waitress and used her money I gave her to pay. The music was jazz, which I detest, however the beat got her moving, and shortly after I could feel an orgasm building. I reached under her dress, realising that she was rock hard, and within a minute or two of frantic stroking, by me, she climaxed as I poured a torrent of cum inside her bowels.

Using cloth napkins, we cleaned up as best as we could, and Penny went back to the ladies to put her panties back on, which by the time we got back to the hotel were soaked through front and especially back.

As we entered the room, Penny locked up, undressed and went into the shower, with me following. She faced the wall, and grabbed my cock and put me deep inside her still gaping and dripping arse. For a girl who was previously a virgin ( almost) she couldn't get enough of my cock up her arse- insatiable!

I ploughed her for all I was worth, this girl seemingly liked it hard and hurried.

She moved away, I slipped out, as she turned round to face me, and I lifted her hips, kissed her as she attempted to insert my cock whilst she wrapped her sexy golden thighs around me. The water was thundering down, luckily she had bundled her luscious hair up in a shower cap provided by the hotel. This is an awkward position, but I pulled her to me so close that I swear my cock was touching half way up her back! We tried this for a bit until I could no longer hold her, and I didn't think I could cum this way, so she turned off the shower and led me to the bath, which she bent over so I could finish inside her again. She dribbled out a tablespoon worth of watery cum down the side of the bath, which we later filled and soaked together. Every now and then a cum fart released some of my cum and we laughed as it floated to the surface.