From Stephen to Stevie Ch. 01

This story started about 10 years ago when I went as usual to Manila on business. I stayed in Makati, close to where the big international companies had their regional offices.

This trip started out no differently to any other trip. I thought I would check into my suite at the Peninsula, head downstairs, and get a taxi to Green Belt and try get some dinner.

On this occasion, I travelled to the room alone, and sat down waiting for the bags, but as there was a convention checking in I assumed it would be delayed. So, knowing the Bell Hops have a key, I called down to the concierge and told them to simply send the bags up and don't knock, and the Bell Hops tip was on the desk.

I undressed, grabbed a toweling robe from the wardrobe and hit the shower.

After washing off the grime from a long journey, I opened the shower door to see the Bell Hop looking at me emerging wet and naked from the shower.

He was a slight chap, slightly effeminate, and as he struggled with the bags I pushed the door closed, as I was naked at the time.

I called out my thanks and suggested he take the tip from the table. It was PHP 2000 not a lot for us but a decent tip for a local.

I toweled off, and emerged from the steamy shower to see the Bell Hop standing awkwardly, semi bowing in gratitude.

I looked carefully at him, and there were feint traces of make up on his face -- Maybe it was a girl, but a second glance at his trousers, which were tenting, it was definitely a boy.

I am generally straight, but have been know to walk on the dark side, especially with the beautiful ladyboys and sexy femboys so prevalent in South East Asia, so I felt a mild twitch from my huge cock.

I realized he was asking for the key for my suitcase in order that he can unpack for me, so I walked towards my carry on bag, whilst wrapped in a towel, which I loosened so as I spun round and bent over the chair where my small bag was, the towel slipped off and my bare butt was exposed. I turned round, holding the key, (I was semi erect) and the Bell Hop, blushing, walked towards me to take the key.

He looked very flustered especially as I made no attempt to cover myself, and grew to my full length, which was 8 and half inches long, and very thick.

I went back to the bathroom to dry my hair, and when I emerged, still naked, the poor Bell Hop was still standing there and hadn't moved.

I Sat on the bed, reached for my Blackberry and scrolled through some messages.

He unpacked, ignoring me but kept looking over. As he bent over to place my socks in a low draw, his shirt un-tucked from his trousers and I noticed he was wearing a pink lacy thong. That really turned me on. I called him over to me, and said I noticed his panties. He blushed, and then brazenly said

"It's a T back Sir not panties, would you like to see?"

My cock twitched, I was still naked and said

"Yes please!"

He lowered his gaze to his belt, which he loosened, then unzipped, pulling the black trousers down to his knees. I noticed his cock in the see through panties had started oozing cum.

"Lock the door," I commanded. He took his trousers off walked to the door, removing his shirt on the way back, where he had a satin vest under it, and hard nipples.

He seemed nervous. He stood next to the bed, with his Asian sized penis jutting rudely out of the side of the panties. He had no hair below his eyebrows and his head hair was floppy and long.

I took his hand and placed it on my cock. This seemed to break the ice, and he gripped it hard, bent over, (I could see the T back in the wardrobe mirror as it disappeared into the crack of his light brown arse) and he started to stroke me, bending over to put me in his mouth. He started to lick the end, and then took my cock into his mouth, and sucked me, fondling by generously sized ball sack too.

Within a few minutes I was ready to cum, I didn't warn him, but he seemed to know, so he looked up at me kept perfect eye contact as I spurted 7 or 8 times into his mouth.

He opened his mouth, I could see my cum on his tongue, and then he swallowed it all down.

Wary of the time, he checked his watch and started to get dressed, he stuffed his leaking cock back into his panties, dressed, took the PHP 2000 and left the room. As I stepped down from the bed, I was still dripping cum, so I went into the bathroom for a long soak in the tub.

I was sated, and didn't want to go to LA Café to find a woman or preferably a ladyboy, so I ordered room service, which was delivered by an elderly lady, and I ate alone.

The next day, I skipped breakfast, walked to the Shangri La round the corner to meet a supplier, then on the way back I sat in the shaded terrace area of a well known US Coffee chain, and ready some notes whilst having an iced coffee and a slice of cake.

I could sense someone was in front of me, blocking the sun, so I looked up and recognized the Bell Hop and he was with a friend, a girl in her late 20's with very long brown hair, and a lovely smile.

"It's me Sir- Stephen from the Peninsula and this is my cousin Frannie"

I recognized him, but he was in denim cut off sorts, his face had more than a hint of make up and he didn't seem embarrassed at all.

"Hi.... Sit down, can I get you some cold drinks or coffee "

They answered n the affirmative and I slipped into the main store and came out with two mango shakes and a couple of cakes, and they were chatting away. I kept noticing Frannie glancing at my lap as presumably Stephen recounted some of the earlier happenings in my suite. As it turned out she owned a condo just behind the giant SM mall -- a parting gift from her Japanese ex boyfriend and seemed solvent, unlike most of the locals. Stephen was from a small island called Tacloban somewhere south and was staying with Frannie whilst he established himself in the hotel he worked in.

What was clear is that what happened with Stephen could never happen again in the hotel as it was a breach of his employment rules. Frannie was a trained Chef and offered to cook for all three of us that night. As my business was over for the day, we went onto the food section of the Mall and I purchased all the ingredients required for a local dish that she wanted to prepare for an early supper. Neither of them used alcohol, which worked for me as I rarely imbibed myself in those days.

I obtained directions to the condo, and then walked back in the punishing humidity to my hotel where I promptly fell asleep on waking at 18,00 for a shower and a very short cab ride to the condo.

When I arrived it was just Frannie there, so we started chatting, she told me her life story that led her to dancing at a club in Tokyo, meeting a gang member, who was quite high up, and she lived with him in Tokyo before she realized it was going nowhere but being a gentleman he purchased a lease on the nice 2 bed condo we were sitting in.

She busied herself with cooking and chattered about Stephen, being what they call a 'soft boy' and his effeminate nature. He was older than I thought and when he came in he came and sat on the sofa next to me.

Frannie wandered back in, sitting on the end of the couch, an arm loosely draped over Stephens shoulder. She chatted away and poured a glass of wine- I don't usually drink, so I had a sparkling water and Frannie as if Stephen wasn't there told me that Stephen was gay, but that he was very effeminate and she felt he was more like a woman than a man. Stephen didn't even blush, and as the evening darkened, and lights went on I could see clearly that Stephen had a bra on under his t-shirt and more make up than before. Frannie cooked, served us pork adobo and rice, and then left as she had a date, leaving Stephen and I to clear up.

The minute the street door closed, Stephen was on my lap, holding my face and kissing me deeply. Deftly he undid my flies, and felt for my huge cock, which was filling my tight boxers.

He knelt on the floor and pulled my trousers and pants down, proceeding to suck my cock again. He was licking my balls rolling them in his mouth, one at a time as they are pretty big before standing up, asking me to wait 5 minutes and then go through the doorway which as he pointed out led to his bedroom. I took the plates into the kitchen scraped them and stacked the dishwasher before going to the bathroom and having a quick wash.

I didn't need to knock on the door as it was partially open, and as I went in, wearing just my boxers, there was Stephen, sitting on the bed in a long wig, more make up, wearing black lacy stockings and a suspender belt, an uplift black bra, and no panties.

I walked towards this exotic erotic Asian vision of beauty and lust took over me as I pulled my pants down and walked towards her open mouth, thrusting deep inside her. Suddenly she / he gagged and I felt my cock disappear down her throat. She sucked me as I ploughed her mouth, till she held up her hand with painted nails, which I noticed on the couch, asking me to stop. She unclipped her bra, revealing two tiny tits, with jutting nipples. Not even an A cup. She squeezed them and offered her nipple to me. She scooted on to the bed and -- naked now -- I joined her, suckling her nipples one at a time. She reached down stroking herself to her full length, a surprising 6 inches -- but thin.

He / she seemed fully erect, and quite excited; I was also at full mast. She turned over, raised her butt and asked me to fuck her.

Initially I felt I couldn't do this as her hole was so tiny, but I thoughts I would try. I started to lick her tiny rosebud. I put one finger in, then two, it seemed that lube had already been applied liberally, and as the hole opened to my probing, it was clear this wasn't a virgin arse.

I coated my cock with lube from a tube lying on the bed and lined up my fearsome cock against his / her tiny hole and gently breached the ring of muscle, hearing a girly yelp and the ' him' became a 'her' as she pushed back surprisingly taking me in one thrust to the depths of her bowels. As she had been sucking me and her arse was both tight and slick, after only a few thrusts I started to cum.

Normally I can last a long time- but the sight of my huge cock inside a reddening stretched arse was too erotic and I climaxed filling her with seemingly gallons of hot spunk. I withdrew and watched my cu, literally pour out of her wide open stretched arsehole and she turned round and said

"Wow- that's the first real cock I've had, only toys in the past and fingers "

I was astonished. We lay and chatted, I got hard again, we made love slowly this time, and in missionary, her stocking covered legs astride my hips, as I made love slowly, whilst she was flinching as I was reaching parts that no toy or finger had ever reached. As I climaxed inside her again, she made herself cum, and jet after jet poured out of her cock over her chest, splattering her face and hair.

We went for a shower, chatting away, and I left shortly afterwards.

The next two days, I saw her one time during the morning, she brought me some messaged from the Concierge desk, and teased me by opening the front of her uniform trousers and showing me black see through panties.

On my last night, I went to Frannie's apartment again, she wasn't there, she was with her girlfriend, at the cinema and we made love brutally up against the wall in her walk in shower, and I left as I was flying back the next morning to Beijing for another round of meetings. I then flew home, but using the 'wechat' app we kept in touch and she said she was waiting for me.

Before I left I gave her a few hundred dollars towards her hormone treatment, which she had started a few weeks previously. It was 4 months until I had cause to visit Manila again, but we kept in touch, and from time to time I sent her some money for hormones, make up and clothes.

When I returned she was still working at the same hotel, so I deliberately stayed at the Shangri La so she could visit my room in privacy.

When we met at the airport, I timed my arrival to the start of her two days off, I noticed some changes. For a start, her hair was in cut into a 'bob' maybe 2 inches longer than before, she was wearing a little yellow sun dress, and seemed to have slightly larger boobs, although it's hard to tell as many Asians wear very big padded bra's.

I checked in as she lingered by the lobby, and we walked round to the elevators, taking the short trip to the 17th floor.

I wanted a shower as I had flown in from Europe, and as I returned to the room, Stevie as she was now knows as stood there in some black hold up stockings, sexy matching panties and I could see that where she had removed her bra she had the beginnings of a very natural looking pair of A cups.

She dropped to her knees, sucked me to full length and then leaned over the bed. I noticed she didn't seem to get hard, but as I pounded her arse, she began to leak clear pre cum form her cock, which I had never actually touched, but I was fascinated about. I reached under and found her tiny hairless balls, and stroked them gently. As I did that amidst a few girly gasps and yelps she suddenly exploded a huge amount of cum over the bed, which precipitated my orgasm.

We collapsed in bed and I explored her body, noticing slightly softer skin, jutting nipples on small sexy boobs, which were very sensitive. We slept, and then on waking I took her to the mall and bought her some cosmetics, hair products, and some new clothes.

We went for a meal in the mall, before returning to my suite where we proceeded to make live again. She was very sore, so when we woke the next morning, she decided to suck me, maneuvering into a 69 position. I felt this was a test, she I licked the end of her cock, which started to harden, before drawing it into my mouth. I was lost in the feelings f her sucking me and as she put a finger inside me I exploded into her mouth, and shortly after she did the same. Several jets of salty cum some of which went straight down my throat spurted from her cute cock.

She slid round and kissed me, our cum mixing and blending until she swallowed it all.

We spent the next day shopping, sightseeing, and when Stevie went back to work, we met for a last dinner before I had to return to Europe.

It was clear to me that this was no boy, not even a femboy anymore, but a ladyboy.

There were tears when I said I could return for 4 or 5 months, but she said she would remain loyal and clean for me only. I believed her and I was right as next time she was just as tight.

She had expressed a desire for some surgery to give her more confidence, this was to be in Thailand, so I agreed to transfer her the money to get some implants and also to keep the wolf from the door during her recuperation. She told me of her dreams to be what she called a ' real ' woman one day. I told her to taker things slowly as certain things such as surgery are largely irreversible.

Next chapter will come soon...........in this I explore Stevie's rapidly changing body and her development into the woman she always felt she was.