My First Ladyboy

She was my first.

Before I tell you more about her and how I ended up in bed with this gorgeous creature, I should probably make a couple of things clear. First, I am a straight, alpha male. Ex-military, been through a few wars, worked in Africa for a while, have been married and never even looked at another male in a sexual way. Still don't, as there is nothing about the male form that does a thing for me. But one look at that gorgeous peach of an ass and I was in lust.

A few years ago now I had been on several dating sites and had chatted with a number of nice women. I am over six feet, ex-rugby player and while my six pack definitely packed up and left a few years ago, I stay in pretty good shape and I have never had difficulty attracting women. I tend to prefer brunettes and go for slim girls as I have never been attracted to the big boobs, big butt look. But most importantly, I am always searching for girls who enjoy my favourite sexual pastime, anal sex. I have always preferred anal to vaginal sex and have had some great luck over my lifetime in either meeting women who enjoyed this type of pleasure, or taught them to enjoy it.

I had been chatting online for a couple of weeks to a young lady from Texas, and we had a few things in common. She seemed pretty nice and eventually she decided to tell me her little secret: she was transgender. She had transitioned in her early twenties and had decided not to have any surgeries, so still had the 'boy' gear in front. I have to admit, I was a bit shocked, but after a bit of thought I realized it didn't matter to me. Her profile pics were gorgeous and some other images we had exchanged made it clear she was a woman who I was definitely attracted to. Since I had not reacted badly to the news, we had some interesting discussions after that. It was when she was telling me how boys she dated loved all the anal sex, the light went on in my head. Here was a whole category of women who made having their asses fucked the central theme of their sex lives. From that moment on, I saw transgender women differently. We never ended up getting together, but my dating choices definitely changed after that.

I soon expanded the search parameters on my dating site and immediately was flooded by profiles of truly beautiful transwomen who all seemed to want to meet men who were 'straight' and would treat them like women in return. I made it clear in my profile I was a 'top' only, just to avoid anything I wasn't going to be up for. One profile in particular caught my eye. Jennifer was from the Philippines and was absolutely gorgeous. We began chatting and hit if off immediately. Very soon we moved to video calls. Not long after I booked a flight to Cebu and a rented us a chalet at a nice beach resort.

We met at the airport in Cebu and I was immediately struck by how much more beautiful she was in real life. Jen is about 5'8" tall and slim in build with long, lustrous black hair and big, almond-shaped brown eyes. She had very small breasts, which was fine by me, and long legs rising to a perfectly shaped ass. Everything about her screamed sexy, sensual woman.

As I walked towards her, she smiled shyly and only resisted a little when I pulled her into our first kiss. I remember thinking as our lips met that I should be feeling odd about this since is strictly biological terms she was a male, but everything else in my body and mind just felt truly happy to finally be there with her in my arms.

We grabbed a taxi to an upmarket hotel I had booked for the night in the city before heading to the resort the next day. It had been a long flight, but I definitely wasn't feeling tired at all. In fact, I felt electric. We chatted in the taxi and held hands and she couldn't stop smiling. Her cheeks were flush as she was feeling a bit embarrassed by my obvious affection - it seemed ladyboys in the Philippines never received this type of response from Filipino guys. At the hotel, she shyly hid from the check in staff as I got our room sorted, but as soon as we were in the elevator I pulled her to me for another kiss. I am sure she could feel my erection straining in my jeans as she held her hips hard against mine.

Once we made it to the room, we quickly dumped our bags and headed straight for the bed. I was determined to take it a slow and not scare her, but Jen had other ideas, in a tangle of arms and clothes we stripped off hurriedly, although she insisted on keeping her panties on. She knew that I had never been with a ladyboy before and was worried that maybe the sight of her 'front bits' might turn me off. If I had had any doubts about my desire for her, it became quite obvious in those first moments that they had disappeared quickly. I had a raging hard on that she kept her fingers wrapped around as we kissed passionately.

After some amount of time, I have no recollection how long, she broke our kiss and slowly slid down to take my cock in her mouth. For the next few minutes she gave me a fantastic and enthusiastic blowjob. She would keep her big, brown eyes on my face as she worked her tongue and lips over my cock, which excited me hugely. She was obviously enjoying the whole experience of having a big, strong, straight male so turned on by her alone. I think she was also impressed by the fact my size was at least a couple inches longer than the average Filipino dick and seemed quite impressed.

But she knew what I wanted more than anything, as we had talked a lot of my love for anal. I had described in detail, over many video calls, exactly what I wanted to do to her ass the first time we were in bed together. She did admit she was a bit nervous. She had only had sex a few times before with a college roommate who used to come back to their shared dorm room at night, frustrated with the college girls he had been chasing. He would wake her up, or 'him' I suppose as at that point she was more of a very feminine boy who hadn't transitioned at that stage. He would roll her over on her tummy and with a bit of hand lotion for lube take out his sexual frustration on her little ass. Jen told me she never minded, and secretly loved the attention, but since her roommate would then ignore her the rest of the time, there was never any proper relationship between them.

The fact that I not only obviously wanted her, but also adored her and had been telling her so for some time over our video calls, had made her almost as desperate to offer her tight little rosebud to me. Sliding back up my body for a long, warm kiss, she demurely asked if I had brought any lube. For a moment I froze and must have looked pretty panic-stricken. I had figured I would grab some at the airport when I landed, but not knowing the layout of the airport and super keen to find her in the arrivals lounge, I had forgotten all about that critical detail.

Jen just smiled and whispered that we needed to get some soon, as I was pretty big. But she grinned and licked her fingers before reaching back and lubing up her ass with spit. My smile must have been obvious as I realized I wasn't going to have to wait to get inside that little ass. Relief flooded through me. "Idiot!" I thought.

After adding as much spit as she could muster, all the while gazing at me provocatively, Jen laid down on her tummy and arched her rounded ass into the air, wiggling it back and forth. I climbed to my knees behind her and gazed down at that perfect peach. God, it was beautiful. Perfectly shaped, round and smooth. I reached down and slowly pulled her little panties off her ass cheeks and with a bit of awkward twisting about, managed to slide them down her legs and off. Jen kept her legs close together so I would not be accidently glimpsing any 'boy parts.' To be honest, I wouldn't have minded, but I think Jen, even more than me, wanted to be just a woman for me at that moment. I leaned down and taking her hips in my hands and began kissing those lovely cheeks. I worked my way from one to the other paying homage to their glorious perfection.

I might have done more, like kissing and licking her little rosebud but Jen didn't want to wait any longer. Wiggling her hips again, she looked back over her shoulder and told me in no uncertain terms to, "get my cock inside me now!"

I rubbed some more spit on my cock head and leaned forward lining up the tip with that little brown hole. When Jen felt it touch in just the right spot she gave a quick push backwards onto it, driving my head past her outer sphincter with an earthy grunt. We both held still for a long moment, while she panted and tried to relax.

"Move just a little bit," she said, eyes closed and concentrating intently.

I began just tiny little movements in and out, across her incredibly tight anal ring. God it felt amazing. Every little movement over my sensitive cockhead sent chills coursing through my body. Suspending myself on outstretched arms, I also had the perfect view of my cock pushing in between to those two perfect globes of her ass. In all my hopes, dreams and fantasies of this moment, none could compare with the reality of this experience.

After a couple of minutes Jen gave another push back and took maybe half my cock inside with another grunt. We kept this pattern up for a few minutes until finally I was seated completely against her rump, cock fully buried inside her. I lay down across her back, continuing my small movements and turned her face so I could kiss her lips and whisper how amazing her tight little ass felt.

"Oh, gawd, your deep," she panted. "I feel like...I never felt so full!"

Slowly I began to pick up the pace, taking longer strokes and Jen just lay there panting and moaning. It was a strange moment, we were both enclosed in our own little worlds, Jen feeling completely full and little rushes of pleasure racing through her each time my cock pushed across her prostate. I was in heaven as my cock was encased in the tightest, hottest ass I had ever experienced. Yet, we were also intimately linked in that moment, sharing the most special kind of bond.

I think we lasted about ten minutes before I felt the growing rush of my orgasm coming. Jen could feel it as well and looked back at me again, "Cum...cum inside me...fill me!"

Moments later, I began groaning like a grizzly bear as I pumped pulse after pulse of cum deep into her bowels before collapsing on top of her. My heart was racing like a freight train and I was gasping for breath. Jen, for her part, lay there twitching below me. I didn't know right away that she had cum at the same time as well, but when we finally moved she had left a sweet little puddle of her own juices on the sheet.

We lay there for a while, me embedded in her ass, resting. I don't recall that we talked much. Eventually, she kissed me and slid out of bed, heading to the bathroom. I watched as that perfect little, well-fucked ass bounced across the carpet. I was in heaven.

We spent two more weeks together, travelling out to the beach resort the next morning. Jen and I went snorkelling, parasailing, and lounged by the shimmering pool. We chatted about our lives and I learned even more about my island beauty. Of course, we made love three or four times a day. We had stocked up on lube before leaving the city and she still teases me to this day about grabbing a tube of KY in a pharmacy and holding it up.

I called out in too loud a voice, "Is this it?"

Jen turned red in embarrassment as half a dozen shoppers in the shop turned to look first at me and what I was holding and then her with knowing looks. I paid for the lube to the smirks of the cashier while Jen waited around a corner, out of site of the store patrons. I admit, I did get a few odd looks as I walked out.

We would wake up each morning and after some pleasant, semi-awake cuddling she would roll on to her tummy, sigh, and ask me what I was waiting for. Naturally, my morning wood was always ready to go and after a quick application of lube, would roll onto her and slide straight in. Jen learned to accommodate me a lot easier as the days passed. I would still start with just gentle movements just inside her tightest ring before filling her completely. Jen would just relax and make contented sounds as I gently made love to her.

As the days went by Jen worked up the courage to try different positions, but always kept a hand cupping her cock and balls so I wouldn't accidentally catch a glimpse. I very much enjoyed laying back one lazy afternoon and watched her ride me. I could tell by the slight motions of her concealing hand that she was gently masturbating at the same time. But for the most part, we stuck to her being taken from behind, which allowed her to relax. She admitted that growing up she had always masturbated while lying on her tummy with a pillow scrunched between her legs and found the most joy being taken in that position.

Eventually though, our idyllic holiday ended and after one more bittersweet evening back at the fancy hotel in the city, I headed for the airport once more. One thing I knew as my flight took off was that I would never be the same man again.