Losing My Anal Virginity in Bangkok

My name is Josh and ever since I was a young man I have always been somewhat confused sexually, and what didn't help was my shyness towards girls and meeting new people. This has led to where I am now, which is nursing a sore ass while enjoying a holiday in Bangkok with my lovely Asian wife Ping.

Let me tell you how this all came about.

As a teenager I was very shy, I worked hard at school and held a part time job, but always let my shyness get the better of me when in the presence of pretty girls. University came and went with only brief fumbling's outside the nightclub leaving me feeling lonely and a virgin when all of my college friends were getting engaged or getting lots of action.

Life went on and into my mid twenties I eventually married the first girl who I slept with, something I now know to be a mistake. I do believe you really need to sow your oats to see what kinks you really like and the same goes for your partner too.

As a boy I used to dress up in my mothers tights and panties before she came home from work, this was very exciting for me and this carried on through my marriage in secret.

I was keeping a secret stash of ladies clothing hidden away in the attic, these clothes were usually bought from the hosiery department of that well know store Marks and Spencer's, and boy did I just love their pantyhose, and their stockings and suspenders.

I would always be incredibly nervous waiting at the till to pay for my new lingerie, wondering what would the sales girl be thinking?

This one time I had the bottle to dress up in girls clothes at home and take a photo, I then posted my picture on a trans dating website.

Then to my surprise one month later I received a reply from a guy and decided to take the first real step in my life as a cross dresser and meet him somewhere neutral, so after a days work I was driving to Johns hotel room to have my first ever meet up as a cross dressing girl.

As I approached his door my heart was beating furiously, I knew there would be an experienced older man the other side of that door waiting to take his younger virgin, that's me!,

Bang! bang!

I confidently knocked on the door, there's no turning back now I thought, and sure enough he opened the door.

"Come in, come in," John said and he peered out the door to see if anybody else was watching.

He looked older than in his photo, don't they all I guess?

I said to John,

"Hiya love, before we start please let me take a quick shower and dress up for you darling, and I'll be all yours tonight."

I closed the bathroom door behind me and locked it.

With my heart still pounding and my cock erect I shed my clothes, showered, ensuring I washed my ass the best I can and proceeded to transform myself into the sexy young virgin I wanted to be for him.

I had chosen to bring a lacy black suspender belt and stocking set with matching black knickers which I put on over my suspender belt for easy removal, a short black miniskirt and a pink top, light pink hair wig and red lipstick with pink blushed cheeks.

I finished the look with a a pair of pink sparkly sunglasses.

I looked in the mirror and thought wow I look amazing, a million dollars, now go out there and let him take me on a wonderful journey.

I exited the bathroom and there he was, about 48 years old, very tall and manly.

"Hi sexy, sit down here" he said and he sat next to me on the side of the bed.

His hand was now caressing my stockinged knee, I wrapped my hand behind his back. We kissed a little, he took off my sunglasses and said "you look fabulous, now lay down on your front," and he reached out to his bed side table and grabbed something.

He was sat over the back of my knees, his hands running up and down my stocking clad thighs and over my ass.

He had already removed his pants and shirt and was completely naked.

I lay there in stockings and suspenders, in anticipation of losing my cherry.

He lifted my skirt to my waist, lowered my knickers below my ass cheeks and then I felt it, a hard cock, riding up and down my ass crack, back and forth, then just when I was enjoying the suspense he stopped to open his condom, but now what followed was so damn disappointing for me.

"Sorry hun," he said, I just can't seem to fit this condom onto my huge dick, I'm just way too large."

I looked around, OMG his cock was huge, the first cock other than mine that I had touched and held, and to be honest the size was really scary.

We both took turns to stretch the condom around his cock head but every time we failed. I then tried with my box of condoms and we failed again. I even tried putting one on the entrance to my mouth and offering him a blow job, but hell no we could not seem to put it on this monster of a cock.

He faced me and lined up our cocks together, his was all of eight inches to my five and three quarters. He held them together in his strong hands, squeezing gently. It was now that I knew what a real mans cock was, I felt dominated by his size, maybe it was better for me to be a receiver than a giver, had I found my calling?

Disappointingly he was a gentleman and refused to bare back me and fill my ass with his cum, so I sucked a cock for the very first time in my life to try and keep him happy. I remember his manhood stretching my mouth so wide and me being so frightened not to scratch him with my teeth. He fucked my mouth for a long time, he dry humped my ass crack, we 69'd, but at no time did his monster cock cum, shrink or in any way reduce in size. I can only assume he was on tablets?

I sat on top of him, his fingers probing my ass.

He said "your so tight, you really are a virgin."

"Yes I said," but I craved not to be.

At midnight it was time for me to wash and go home, so I moved into the shower and he followed me in. There he was standing with his hard cock pointing skyward, I automatically knelt down on the hard floor and took his cock in my hand, licking the whole length from balls to its mushroomed head, then little by little it entered my mouth, my hand cupping his balls, then he gently thrusted back and forth but he couldn't climax however hard he or I tried. He then stood me up and pushed my front against the glass shower wall, with warm water running down my back he fucked between my ass cheeks but without entering me bare back.

I was in two minds, half of me wanted him and his lovely long and thick cock to ruin my ass and bring me to an amazing orgasm, the other half was scared of being bare backed and the worry thereafter.

His hard and ever erect cock still couldn't cum.

"Thank you babe for being so patient," he said and he left the shower, we both dried ourselves and dressed, I collected my girly clothes, we kissed one more time before I went home feeling disappointed that my ass was still a virgin and that I had missed out on tasting another mans cum.

Many years later and now happily married to my new Asian wife we booked a holiday to Bangkok in Thailand, a wonderful but crazy place to be.

Walking out to dinner, and to my delight there were scores of young Ladies and Ladyboys offering their services to every foreign man who walked by. For several nights I fantasized about sleeping with a Ladyboy, they looked so sexy, long tanned legs, great boobs, and the way they carried themselves with an extra wiggle of the hips had me transfixed.

Then in a bar one night we were having a few drinks and I was feeling horny watching the sexy working girls and Ladyboy's competing for the foreign tourists. Just around the corner I spotted a street trader selling sex toys, and on leaving the bar my wife and I walked up to the trader, I was feeling somewhat nervous about what Ping would think of me but I was turned on.

"Hi, do you have you something for bum bum fun," I asked.

Ping giggled.

"Yes Sir," he said and produced 2 boxes of strap on dildos.

"5 inch or 8 inch Sir?" he said.

With the bravery of 4 alcoholic drinks already inside of me I said "8 inch please."

Ping squeezed my hand knowingly and placed the box in her bag and we paid the 1000 baht to the trader who gave me a cheeky smile as we left. As we walked my cock became hard and wearing just shorts and a T shirt it was quite hard to hide my tented shorts from the general public walking by. I said to Ping lets get a drink, I need some Dutch courage, and we headed back to the bar. She looked disbelieving of what had just happened.

We then stopped for another 2 drinks in the bar to contemplate our actions and remove our shyness before we went up to the hotel room.

I showered first, then opened the box and took out the long but soft, flesh colored dildo, attached the straps, and placed it on the bedside table next to a tube of lube, and got into bed naked.

Once again I was anticipating the loss of my anal virginity, albeit not to a real live cock but to the same sized monster as John had let me down with all those years ago.

Ten minutes had passed, my wife dimmed the lights and I felt her moving around the end of the bed. I rolled onto my front and waited in anticipation.

I felt her nyloned legs as she positioned herself over my legs.

I felt her squeeze liquid gel onto my ass and a finger traced a line of gel along my crack between my ass cheeks and it stopped at my star, then circled a little more.

Then I felt the soft dildo sliding gently between my ass cheeks, up and down the crack, just like what John had done before, then she lined it up with my anus and pressed forward. I felt my ass stretching and resisting, she maintained the pressure and I tried to relax.

I pushed back a little to meet her thrust and then the feeling of acute pain took my breath away as my sphincter dilated and my ass stretched around this pink cock and the head began to enter me.

Inch by inch she penetrated me, then there would be a rest and then another inch.

The pain got more and more intense as two, then four and now six inches were thrust inside my not so virgin ass. I felt underneath to check my own cock, it had shrunk to the smallest size possible, a dribble of pre cum had wetted the sheet below, then without request she withdrew from me.

My empty ass felt cold inside to the coolness of the air conditioned room.

"I'm taking off this belt, its uncomfortable," Ping said, and she did.

"Girls should be wearing stockings my love, so that's you tonight and not me," said Ping and one by one she removed her hold ups and lovingly pulled them up my legs and straightened them before resuming her position behind my ass.

The silky nylon stockings made me feel more horny and excited and ready as a woman to accept her cock.

Ping then applied more lubricant to the dildo and pushed it back inside my ass with her hand. Just two inches at first, then four, and now six inches.

I reached back, still in great pain, feeling for how much more cock would I have to take, I felt there was at least another 3 fingers width to go when she pushed again, now I felt the cock being pushing up into my stomach, my ass full up to bursting point my little cock squashed into the bed sheet below. Then finally I felt the balls pushing against my ball sack, I was relieved and felt a sense of pride that I had managed on my first time to take all 8 inches.

Ping started a slow pumping motion back and forth, I felt both pain and enjoyment at the same time, it was gradually getting easier to take and I felt my own cock stiffening.

Unfortunately she stopped after 5 or 6 minutes of fucking me, her being too worried about damaging my ass.

She apologized, got out of bed and washed the pink flesh colored dildo, returning it to my bedside table, then kissed me and turned out the light.

"Goodnight hunny, I hope your OK in the morning?" she said.

"Thank you babe," and my head hit the pillow.

Maybe four hours later I woke up, it was still dark, I turned my pillow around so I could cuddle it, and grabbed hold of the dildo which I placed by my lips. As I licked along the long shaft my cock rose to the occasion and snuck under the end of the pillow, I was still in this permanent state of excitement as before.

This 8 inch monster seemed to have a power over me and I started to lick it along the shaft up to the top then I took the whole width into my mouth, with a gentle sucking and licking motion I imagined the dildo to be a real cock and me satisfying the owner.

I was ever so turned on again.

After what must have been ten minutes and with the wonderful cock now half way or more inside my mouth, Ping woke up and rested her arm around my waist and gently massaged my bum cheeks. Without touching my cock I climaxed like never before, cumming all over the pillow and sheet below.

It felt wonderful.

She must have sensed that I was cumming and fingered my deflowered ass and I cum again and again onto the bed sheet.

So here I am completely satiated, with a sore ass and feeling submissive to this massive cock which is now my master, and never to be denied.