Pearl

Pearl of the Orient

A Transgender Experience

He discovers his real sexuality when he takes a trip to transgender heaven.

My wife of 10 years had taken another lover. I only found out when I saw her car parked at that motel on that day, when she was supposed to be working. My carpet cleaning business often received callouts from hotels and motels after guests had spilt something or other. I had asked myself many times why that coincidence was how I found out about her cheating.

When she came home that evening, I was unsure how to ask her why she had been at that motel at 2 o'clock in the afternoon. I kept telling myself there must be an innocent explanation. My wife headed straight to the shower without saying much when she arrived home, just after 4 pm.

"Was she washing the smell of another man off her?" I wondered to myself, and an idea came to me. As soon as she was out of the shower, I went to the bathroom. A pair of red panties I hadn't seen before were lying, hidden, under a skirt in her laundry basket. I picked them up. They were low-cut and lace-trimmed with a heart embroidered over where I guessed the opening to her pussy would be when she had them on. The panties were not the same as the regular beige or white cotton, high-cut style in her underwear drawer. I looked closer inside to notice that the crotch section was slightly discolored, like something had leaked from her pussy--I guessed at what that might be--shocked and dreading what it might mean.

In the kitchen later, I told her about my day and the call-out I had received to that motel. Her reaction to that was hard to gauge, but there was a fleeting expression of something strange on her face. I decided to press on.

"I saw your car there at the motel."

She said nothing at first, but her silence spoke a thousand words of guilt. She wouldn't look at me. After what seemed like a few minutes, but was probably only a few seconds, she said, "Well, now you know--and I want a divorce."

"Why?" I asked.

"We haven't had sex in months--or didn't you notice that?"

She was right; I had not had any desire for her in a long time. I didn't know why, but the thought of sex with her or, for that matter, any other woman, no longer appealed to me. I knew I wasn't gay; men had no interest for me sexually, but I had just lost interest for some reason I couldn't explain.

The divorce wasn't too difficult; we hadn't had any children, and the financial split was 50/50. It was largely amicable.

Two and a half years have passed since then. My friends have told me to move on with someone new, but I was worried I would repeat the same mistakes. Something was missing, but I didn't know what. I slowly returned to masturbation, spending a few nights in front of my laptop, but porn seemed so boring that I almost stopped looking, until that night something popped up on my screen that both frightened and excited me.

She was a beautiful girl with a dick. She was wanking herself off in the video, ejaculating strings of white cum at the camera. I was drawn to her stunning 6-inch cock. I watched that video over and over. The girl looked Asian. I had found something that excited me.

I asked myself, "Am I gay?"

But I was sure I wasn't. Men didn't appeal to me in any way. But a gorgeous girl with a dick? That was another thing.

My cleaning business had been doing well, and by now I had two people working for me.

"It's time for a holiday," I thought.

I hadn't stopped working since the divorce. My mind was on Asia. So many of the videos I watched each night were of brown-skinned beauties with throbbing cocks. I watched transgender porn from all over the world. The size of the South American girls' members was scary. I liked something a bit more average in size. I fantasized about sucking a beautiful cock, and it exploding with cum in my mouth. I wondered how a ladyboy's ass tasted, and liked the idea of tonguing a transgender woman from behind while stroking her dick in front. I imagined how my cock would feel clamped in a tight muscular ass. What would it feel like if a T-girl came in my ass? My thoughts ran wild. I booked the tickets.

Manila was hot and steamy when I stepped out of the terminal after the long flight. The taxi ride to my hotel was slow, bogged down in that city's famous traffic. It was just after 4 pm when I finally got to the air-conditioned comfort of my room. I had chosen the hotel after searching the web for the location of ladyboy bars, so I would be able to walk to one only 10 minutes away. I lay on the hotel bed, excited at the prospect of satisfying my long dreamed-of desires, rubbing my cock in anticipation. I hadn't meant to, but I drifted off to sleep, waking several hours later just before 9 o'clock.

A quick shower and out onto the street, maps on my phone pointing the way. After a couple of wrong turns, I found myself in front of a bar called Orient. I had seen videos of this place during my online searches. Gathering my courage, as I was very nervous right now, I entered through heavy curtains into a small bar with about 10 or 12 people inside. I headed for the drink servery area, a little scared to look around until I had a beer in my hand. There were 2 or 3 other guys, and the rest appeared to be young ladies. When it arrived, I nervously gulped at my beer hoping one of them would approach.

Even though I got a few glances, I had almost finished my bottle of beer before a beautiful woman walked over to me. She was tall, about 5 foot 9, long black hair, and provocatively squeezed into a tight black dress which barely covered her ass above her long slim brown legs. Her eyes were dark and beautifully made up with a mascara line slanted upward at the outside of each eye, emphasizing her slightly oriental look. Her breasts were large, impossibly so for her slim body, but excitingly

firm and erect.

"Hi," she said in a quiet, low, breathy voice. "My name is Pearl--would you like to buy me a drink?"

"Sure," I replied. She was gorgeous.

"First time here?" she asked. "You know this is a ladyboy bar--don't you? I'm just asking 'cause you don't seem to be in the right place."

"N-n-no, no--I wanted to come to this bar," I stuttered out.

"OK--that's great, 'cause you're a handsome-looking man,... maybe just a little nervous?" No one had called me handsome in years.

"It's my first time in a bar like this," I mumbled.

"Ha--if only I had a dollar for every man who said that. Relax, no one will eat you here, unless that's what you are looking for?" she said, parting her full red lips with a big smile, showing a great set of white teeth. An image of her mouth gently biting on my cock flicked through my mind.

Our beers arrived. She took a long gulp of hers and eyed me up and down, stopping for a second or two at my crotch.

"I really am new to this--how do things work here?" I said.

"Well, you could buy me a couple of drinks and we can talk, or there are rooms upstairs where we can... relax." She said, motioning in that direction, her beer in hand.

"What happens up there?" I asked.

"Whatever you're looking for. You can fuck, suck,--whatever. Are you top or bottom?"

Any uncertainty that I was talking to a ladyboy was gone now. Damn! She was so good-looking.

"I-I've never done anything like this before."

"A genuine virgin--well, I like that. I can be very gentle with you."

My mind raced with pictures of the porn scenes I had watched at home. I ordered her another beer, none for myself, wanting to keep a clear head. She squished herself in between me and where I had been leaning on the bar, her hand quickly finding my crotch and rubbing what was already three-parts of a hard-on. She leaned over closer and kissed me full on the lips, her musky, beer-flavored tongue pushing to invade my mouth. It was incredible, not like kissing a woman at all. She was making all the moves. A little scary but so exciting at the same time.

She drank fast. I paid for the drinks and the room charge, then we headed upstairs. She walked in front leading the way up the stairs, swinging her stunning ass with red panties on--her butt on full display. I followed three steps behind, my eyes fixed on her rear end. She opened the door to a small air-conditioned room with a large bed and a small bathroom. "Get comfortable and I will be back soon."

I stripped down to my briefs, my cock bulging in front. It seemed like an eternity, but it was probably only 5 minutes, when she returned with a small tray of items which she placed on the bed. She was stripped down to a red bra, bulging full with her heavy breasts, and wearing those red panties I had followed up the stairs. She turned the lights down so it was hard to see, until my eyes adjusted to the glow from a bedside lamp.

"Lie down and relax. Let's start with a little massage--lie on your stomach--tell me what you like," she whispered close in my ear, and pushed her tongue inside it slowly. That sent a jolt of electricity through my body. "Take off your underwear too."

Once I got comfortable, she reached for a small bottle from her tray, and rubbing something on her hands, she climbed on top of me, her legs astride my butt. I could definitely feel something hard bulging from those red panties as she leaned forward and began to rub my shoulders. My thoughts of this perhaps being a regular massage disappeared as she soon moved her hands down my back to squeeze my butt cheeks and slip a finger into the cleft between them.

She leaned forward. "Open your legs," she whispered into my ear, "No... wider."

Soon one of her fingers found my asshole and rubbed deliciously around my pucker.

"Do you like that?" she asked.

"Incredible!" I replied breathlessly--sparks jolting through every nerve in my body--my back arching involuntarily. She paused for a moment and then I felt her fumbling for my rock-hard cock, freeing it from under my body, so it pointed backwards. Now her slippery fingertips were rubbing my throbbing knob.

Suddenly I felt something moist, warm, and ticklish on my butthole. I knew she had brought her mouth to the party now, alternately licking, then her tongue stabbing, into my little hole. The feeling was incredible as she tongued my ass and rubbed my cock at the same time. I felt like I was already going to cum. She must have noticed I was edging close, so she stopped briefly. I couldn't be sure, but behind me it seemed like she was taking off her bra and panties.

Then I felt her weight on me, her bare breasts rubbing on my back and her cock rubbing up and down the crack of my ass. Was she going to penetrate me? I was not sure I was ready for that. After a few delicious minutes she asked me to turn over, and she grabbed at my rigid tool. My god! I had never had an erection like this with my wife.

She squirted some more lube from a bottle on her tray and began giving me the hand job of my life. She was very talented, that's for sure; one hand held flat on the base of my cock and the other rubbing the full length with a twisting motion up to my swollen knob. She had long fingernails which from stroke to stroke she used to scratch lightly over my shaft. My back arched and I held the back of one hand over my eyes--completely lost in ecstasy.

Just when I thought it couldn't get any better, I felt her moist full lips and tongue begin to lick my cock up and down. After a few laps from her tongue, she plunged the head of my cock into her warm, sweet mouth, pushing down to take my fully erect 6 inches all the way inside.

"You are going to make me cum. I, I, c-can't hold back," I stammered.

She mumbled something, her mouth full of cock, but I think it was, "Give it to me."

Maybe that was just wishful thinking, but just then a huge wave of dopamine hit my brain and what seemed a slow, but inevitable ramp up to ejaculation started. I exploded in her mouth. She drew her head back a little at the feeling of my hot cum spraying her tonsils, but she didn't take her mouth away completely. Waves of the strongest orgasm I had ever had overcame me, my body jerking and spasming as she held on to my cock with her mouth.

Incredible! I had never felt anything like that before from a woman. Slowly she lifted her mouth from my dick, cum and saliva dripping from her pouting red lips. I pulled her to me and kissed her full on--pushing my tongue into the slippery depths of her mouth, savoring the salty, sweet taste inside. I never thought I would do anything like that, but pure sexual lust coursed through my veins. She kissed me back passionately before pulling away and swallowing exaggeratedly. Then she opened wide to show me she had swallowed my juice completely.

She lay on top of me, her head nestled against my chest for a minute or two--no words passed between us. Then she looked at me with a mischievous smile.

"I don't normally do that--but you turn me on so much," she said. I wanted to believe that.

"I am so horny with you. I want to fuck you."

I baulked at those words, not sure I was ready for anything like that. I looked down at her still erect cock. It was similar in size to mine, about 6 inches but not quite as thick. It didn't scare me like some of the dicks I had seen on the web on South American girls.

"I know how to be gentle," she said. "You told me you are a virgin--that turns me on. I want to be the first to take your virginity--I won't hurt you."

I thought about this; it was something I had wondered about and had watched on the net when guys were taken in the ass by gorgeous transgender girls--the guys seemed to like it very much.

"I'm not sure it won't hurt--is it safe? I mean, I don't want to catch anything," I worried.

She was silent for a few seconds. I wasn't sure what she was thinking but, scary as it was, the idea of her cock in my ass was definitely exciting. My cock had subsided after my orgasm, but now my thoughts were making it hard again. I could feel it growing. "If I did say yes and it hurts--you will have to stop."

"Mm-hmm," came the response.

"Do you have a condom?" I asked.

"No, but I get tested for STI's every month. My last test was a few days ago--all clear. I haven't had sex since. Besides, if you let me fuck you, I won't cum in your ass."

My logical brain was saying no, but something had taken over my willpower. This gorgeous woman with a beautiful brown dick lying beside me was drawing me inevitably to want to try everything with her that I could.

"Okay, we can try--but pull out before you cum--yes?"

"Mm-hmm," came the reply.

"How do we do this--what position do you want me in?"

"Well first, can you suck my cock?--I'm hard but want to get harder."

She got up and turned around on all fours, pointing that beautiful ass of hers toward me. She reached down to her cock, pointing it backwards at me. It was dripping with precum. It seemed like she was really turned on. I knew what to do so I took the head of her cock in my mouth and slowly moved it up and down her shaft. She moaned and shook her butt. Her taste was salty and earthy, not unpleasant at all. After taking all of her cock length down my mouth, I sucked and slurped her stiffness back and forth. Pulling my mouth off her cock head, I began to lick up her shaft, stopping to suck gently on her balls and lick up her perineum towards her asshole.

I buried my face between her mounds and pushed my tongue into her little hole over and over. The smell and taste of her asshole was something I will never forget. It was warm, musky, salty, sweaty, and it made my cock stand 100% to attention. I spread her ass cheeks as wide as I could with one hand, and took her cock into my other hand. I must have licked, nibbled, and tongue-penetrated her wonderful brown pucker and stroked her steely brown dick for several minutes, with her moaning her approval all the while.

I pulled my face away from her delicious ass and said, "How do you want to fuck me?" Yes, I had given in totally to her, and to the incredibly strong desire I was feeling.

She turned to me and said, "I think it's easier if you lie on your back, and put your legs up. Here, I will put this pillow under your bum."

I wriggled my bum into position, holding my legs apart and up in the air a little with my hands.

"Okay--that's good--are you sure you haven't done this before?"

"No, just watched a lot of porn. Let's do it--but slowly please."

She reached for her lube bottle and began rubbing her full length with its contents. She rubbed some more on and into my asshole. Then she positioned the tip of her 6-inch spear at the entrance to my chocolate starfish. Slowly, ever so slowly, she pushed her cock forward, stopping to withdraw a little then push again slowly into my tight brown ring.

It hurt! "Owww!" I exclaimed and wriggled my butt.

"Oops, sorry--a little too fast maybe."

She withdrew her dick, which was barely in me, and not yet through my anal sphincter. She leaned over me and kissed me full on my lips, her tongue darting in and out of my mouth, rich with her warm saliva. She leaned back again and grabbed my now slightly deflated cock and began jerking me off with that wonderful rhythm she had used 15 minutes ago. Once again her cock pushed against my little hole.

"Breathe," she said. "Long slow breaths in and out," she commanded.

I tried to relax my asshole. This time her cock pushed in further, just into the ring of muscle inside. She stopped, her cock not quite halfway in.

"I'm just inside you now--relax while your ass gets used to my cock being in you."

While it was still a little painful, it wasn't unbearable and gradually I felt my ring loosen to accommodate her girth. It stopped hurting, now just feeling a little uncomfortable--a bit like my ass wanted to shit her cock out. My pucker pulsed reflexively--which didn't push her out, but allowed her to slip inside me a little further.

"OK--I will try to push in all the way--I really believe you are an ass virgin."

With that she pushed steadily until her whole length was inside my rectum. Stopping again to let my ass accommodate her, she said to me, "Your ass is so delicious, so tight around my dick."

After what seemed a minute or so--she began to slowly slide her full length back then forward into me. Everything changed. There was no pain--there was just a delicious feeling. I felt full up when she was all the way in, and strangely empty when she pulled out. My ass wanted her cock. Instinctively I pushed back to her thrusts, willing her cock to penetrate me as deep as possible. I ground my ass against her loins, loving every forward thrust deep into my bottom. It was fabulous. I loved having my ass fucked! Something I had suspected I would, but now I knew it.

She quickened the pace a little--not pounding me hard but fucking me slowly and

sensuously, stimulating all the pleasure receptors around the entrance of my ass. I reached up to hold and caress her beautiful pendulous breasts as she fucked me--her eyes were closed in ecstasy. She was really enjoying the feeling of her cock sliding in and out of my little brown hole. I reached behind her head and pulled her mouth down to mine.

"Fuck me, fuck me, I love your cock!" I said, and kissed her full on the lips. Her tongue began penetrating my mouth in time to the rhythm of her cock thrusting into my ass. I was in heaven.

After only a few minutes of her glorious cock probing me, she suddenly announced, "I'm going to cum soon." Overcome with the feeling of her inside me, I didn't want it to stop. "No, don't pull out, you can cum inside my ass!" my voice said--my brain no longer in control of my senses.

She raised herself up a little and grabbed my rigid tool in one hand, jerking my cock in time with her thrusts inside my asshole. I too was feeling close to climax--when suddenly she threw her head back, plunging herself deep into me, her cock twitching, jerking and throbbing as she poured sperm into the depths of my bowels. I swear I could feel her cum spurting deep inside me, hitting on the walls of my ass--and it pushed me over the edge. My cock throbbed in her hand and gushes of my own semen scattered over her heavy, sweaty breasts.

"Oh my god!" I moaned as wave after wave of dopamine rush filled my head again, and, it seemed, my ass at the same time. My orgasm washed over me, even stronger than the first one, my ass clenching tight on her still throbbing cock. She collapsed onto me, her cock inside me bathed in her jism, and her breasts slippery between us with my cum. After a minute or two, she slowly pulled out of my asshole with a "plop" sound. It made my ass feel empty and I wanted her cock back inside again.

But as I lay there with her cum oozing softly out from my gaping sphincter, I knew I was totally spent after my two incredible orgasms. I would have to wait and recharge myself before getting another assfucking session from her beautiful brown rod - and I hoped that would be soon.