My TG Tale

Chapter 1

If I could see my future I would have no idea how I could have become what I see; a beautiful, young woman. You see, here and now, I am a slight young man, undersized for my age of 18; at just 5 foot 6 and 120 pounds I am far from the prototypical male physique. I have always been very nerdy and struggled to fit in anywhere or with anyone. As many young males in this position before me I found myself drawn to pornography.

Many years earlier I had stumbled across erotic images on the internet and had found them to give me a thrill I was unable to find in normal interactions. After my first timid steps in this world of visual delight found myself watching progressively more and more, until I would spend easily 5 hours a night after school watching.

At first I just watched good, old vanilla sex but eventually curiosity got the better of me and I started exploring the other categories available on the tube sites. I started picking random categories and sampling their delights; usually one week was given to a category before moving on.

When I first started watching these movies my breath was taken away by these girls, by their beauty and by the sex acts I previously would never even have imagined. I would stare avidly at their pussies, admiring the contours of their labia and vividly trying to imagine how they would feel to touch, to lick, to fuck. This then became an obsession with breasts, moving between small and large, pert and saggy, unsure of what I favoured most. I then began to analyse girls' asses, fascinated by the length of cock they could take.

I would watch as entire shafts would disappear inside these girls' rectums, impressed at the girth, length and savagery of pounding they could take. It was during this time I discovered the Anal Goddesses Sandra Gillet and Katja Malkova. When I discovered this trio they swiftly became all I would watch. It was then I saw the video that would change my life forever, the video with Lex Steele.

It started as a normal afternoon for me, booting the PC and hitting up my favourite tube site. I opened up the Anal section and found a video starring my favourites, Sandra and Katja double teaming Max Hotrod. It started as many had before; the girls played with each other, warming up for what was to come. Then he appeared. It was a muted entrance, strolling in from off camera, but the moment he exposed his cock I was changed. It was perfect. The length, the colour, the turgor. It was breath taking. I watched, not breathing, as the girls worshipped it with their mouths, licking, sucking and gagging on it. I was on the edge of my seat, not breathing, urging them on. Then the fucking started. As Katja first slid down that beautiful shaft I felt a pang of jealousy. Jealousy. I was frightened by this and quickly shut down my PC and sat panicking.

Jealousy!

What did this mean?

I was a regular porn watcher and I had never felt this way before. Not about a female performer being able to take a dick. I was confused and scared. For the rest of the week I didn't even turn my computer on. The week dragged by, I was getting hornier and more terrified than I had ever been. Try as I might I just couldn't get Max and his throbbing member out of my head. Eventually I reached breaking point.

All through college that day images of this magnificent rod kept popping into my head. I kept daydreaming, imagining taking it in my end and slowly jacking it, caressing it and slowly running my tongue up and down. I sank further and further into my fantasy until I was imaging myself on my back with his huge member throbbing against my anus and I moaned, "Max, take me now!"

The laughter started then. I came to with a start to the whole class staring at me. I flushed red and ran from the room, tears already streaming from my eyes. I was humiliated. I ran all the way home. This couldn't go on. If ignoring him meant moaning his name in class I would just have to satiate my desires at home on the internet. I booted up the same video form before and watched it through. I felt the same as before, jealous, all the way through. Especially when the anal started. That at least I could offer him.

With this startling thought, I stopped the video once more. Anal? Anal sex? Was I gay? I had never imagined myself to be but maybe that had been the case all along. But I couldn't be. Hadn't I spent hours gazing at female pornstars online, not male!

It was time to enter into a category I had never ventured into: Gay. I skimmed through and opened video after video but two men fucking just did nothing for me, no jealousy, nothing. Not even a semi. So if I'm not gay, what am I?

I considered what I had felt before. Jealousy. I had wanted that cock to be penetrating me, of that I was certain. That would make me gay, but, jealousy of the girls. I had wanted to be them, not just me sucking his cock. That made me what? A tranny?

Time to enter another category: Shemale. I opened up the first video I found. I couldn't believe this girl was a shemale; she was beautiful. The video progressed and a guy entered the scene with an impressive meaty specimen. My cock twitched as the girl took it into her hand and sank to her knees in front of him. As the camera panned in my mouth opened slightly and my tongue flicked across my lips. I wanted to take it in my own mouth. The tranny started eagerly sucking him off and before long the guy was lifting her up, tearing her dress off and bending her over a sofa. It was when that dress came off and her cock flopped out, dangling from this beautiful woman, it was then I understood why I had felt jealousy. I wanted to be the woman. I wanted to be like this woman before me.

I didn't go back to college the next day. Not for the rest of that week. I stayed at home researching, making sure I was what I thought I was. I ordered some clothes, the most feminine things I could find. I ordered some cheap lingerie and stockings, a skirt and blouse. I spent all my time reading other tranny's stories and discovered that they, we, preferred the term transgendered. The more I read the more I was sure and when my clothes finally arrived there was no turning back for me. The moment I pulled the lacy panties up my legs and the stocking afterwards I knew there was no way back. What would I do now though? I couldn't stay at home and live this way. I couldn't return to college. What could I do?

It was then that my mind wandered back to porn. They must always want new gurls for that. With that thought I went back to my research and found that it could work but I would have to fuck guys on camera. Was I ready for that? I had never even touched another man's penis before. I decided that I had better test my resolve. I went on Craigslist and posted an advert: 18 year old, transgendered virgin, wants an older, experienced gentleman to show me the wonders of sex. "That should get me some replies." I thought.

Chapter 2

Boy did I get replies. I was snowed under by them. I sifted and sorted until finally I found the right guy. He messaged me back with a photo that showed him to be late 30s. He had ripped abs, a handsome face with an average sized dick. For my first time I was somewhat fearful of a large member ripping me in half. We chatted for a while and he told me how he regularly hooked up with transgendered people like me and would be patient with me. He let me know that if I changed my mind when we met about going through with it that was cool too. I felt comfortable and reassured with him so we arranged to meet at a local motel the next evening.

There was no way I could go out dressed up from home as my parents would see so I packed my clothes, the lingerie, the stockings and my only skirt and blouse in a bag alongside my new makeup. I made an excuse about studying to my family and snuck out early to rent the room and get ready my big night. All the way there I was worried about what the motel people would think and whether they would know? I was in a minor state of panic by the time I arrived.

I approached the reception in a fluster. "Hi, I have a room booked for tonight. My name is Alex Mason." The receptionist looked at me and smiled and replied, "Sure, right here. It's room 269. Just across the parking lot and up those stairs on the right." I thanked her and smiled back, stumbling in my haste to leave.

The first thing I did after entering the room was to take a shower. I was sweating after my fears on the journey over and the opportunity for a steamy shower seemed like a good bet to calm me down. Besides, I had a good 2 hours until my 'friend' was coming over.

When I got out of the shower, I put my hair up in a towel and wandered round naked. I had shaved all my body hair off in the morning and I enjoyed seeing the effect in the long mirror in the corner of the room. I proceeded to unpack my clothes from my bag and lay them out on the bed. I was going to take my time and enjoy dressing up today rather than trying to squeeze it in when everyone else was out.

I started with my favourites, the stockings. I carefully bunched up the first one, slowly slipping it over my toes and sensually rolling it up my leg. The feeling was so sensuous my little clitty started to stir. "Not yet!" I giggled to my crotch. I started with the second stocking but my clitty really started to grow. "Hmmm, I'm a naughty horny girl!" I said to myself, a little grin spreading across my face. I finished up the stocking and decided that I should put my panties on next to offer some restraint to my clit. This sort of worked; by the time the lacey panties had brushed their way up my leg I was well on my way to an erection and I was dripping precum but the panties allowed me to tuck it back and conceal it somewhat. Next up was my bra. I slipped into this quickly, which was when I realised I had nothing to stuff it with. I was annoyed at myself for forgetting but chose my socks as a make do. Next, I slipped my skirt up and put on my blouse, leaving a few buttons undone in what I hoped would be a flirty style. I looked across to the mirror again and was impressed at how feminine I did appear to be in just clothing. My slight figure I once cursed was now paying dividends for me. Now I had to sit down and try to apply some makeup, something I hadn't really done at home.

I sat down at the dresser and started with some foundation, lightly brushing my cheeks, dusting them. Next, I carefully drew a line of deep red over my plump lips and filled in the space between. So far I thought I had done ok. Not perfect by any means but not excessively drag like either. I then gingerly applied some mascara, blinking constantly all the time. I was just finishing up when I heard the knock on the door.

My heart leapt. He was here.

I sprang out of my seat and grabbed for my high heels. I quickly fastened them and hurried to the door, and almost tripping right into it. I opened the door with a lurch, my face no doubt a little red. Standing the other side of the door was my new 'friend', Paul. "Hi" I mumbled, the alluring voice I had practised at home forgotten as my nerves flooded through me again.

"Hi." Paul smiled back. "I've been looking forward to this. May I come in?"

"Of course." I hastily stepped back, realising that I had been blocking the doorway, forcing him to remain outside. "Sorry." I whispered.

"Don't be silly." He said to me with a warm smile that melted my butterflies away. Paul stepped into the room and turned to face me as I pushed the door closed. "You look wonderful. When you told me this would be your first time I wasn't sure how you'd look but truly, you look like a pretty, demure young lady."

I blushed at the compliments he was paying me and nervously stepped towards him. "Really?" I whispered to him. "You're not just saying that?"

"Not at all." He held out his hand to me.

I took it, trembling, and he pulled me in close to him. "What about me? Do I live up to expectations?"

"So far, you have exceeded them." I grinned back. With that he leant down and kissed me. It was my first time being kissed and as his lips first brushed mine, I flinched in shock, his stubble gently scratching my face.

"What is it?" He asked, pulling away sharply.

"Nothing. It...it's my first kiss and it was a bit of a shock. You must think I'm silly."

"No. Not one bit. I have an idea. Why don't you control this. You come and kiss me. If you want to anyway."

At this I leant back in, my lips reaching up for his, my eyes closing. As our lips met I trembled once more but this time from excitement, not fear. It started gently but very quickly we were passionately making out, his tongue invading my mouth, wrestling my tongue for control. I broke away breathless and gazed up into Paul's eyes. "That was wonderful." I gasped into his chest. I rested my head on his chest and he pulled me in close.

"Yes. That was great." He replied, pulling me tight into him.

It was then that I felt a stiffness at his crotch. I reached a hand down to it and gently stroked up his length. "Is that all for me?" I asked coyly, peering up at him again.

"Yes, it is." Paul smirked back down to me. "He's been wanting to meet you even more than I have."

"Can I see it?" I asked him naively, to which he replied by undoing his belt and pulling down his trousers. My heart raced as his first his trousers, and then his pants fell down his legs, allowing his throbbing cock free. I gasped slightly. It was the first cock I had seen that wasn't my own after all. I reached out for it, mesmerized, lightly grasping with my fingers. It was rock solid. I felt a sense of pride at what I had done, the response I had evoked in this older, more experienced man. I felt it pulsing in my hand and I let it swing free once more.

"Do you like?" Paul grinned at me expectantly.

"I do." I grinned back excitedly and reached for his member once more.

I gripped his cock and slowly started stroking it up and down. Paul let out a satisfied sigh, which gave me all the encouragement I needed to carry on. As I picked up speed Paul's leg twitched slightly and I gave out an excited squeal. He laughed gently and I dropped to my knees. I looked up at him, fluttering my eyelashes at him. "May I suck your cock please Sir?" I asked in a manner I hoped was sultry.

"Please do." He sighed back at me.

I started slowly, stroking him towards my face as I got into position. I got a big whiff of his musk, which sent my clit into overdrive, straining to break free of my panties. I opened my mouth wide and slowly eased his turgid shaft within. It was velvety smooth and I flicked my tongue over it, savouring the unfamiliar taste. I moaned into his cock, my excitement becoming overwhelming. Paul responded, his cock throbbing more I my mouth. Gingerly, I started bobbing my head up and down on his shaft, relishing the effect I was having on my new 'friend'. Gradually I increased my pace and Paul started to squirm more and more to my ministrations. Eventually he could take no more and pulled his cock free and grabbed me under the arm, tugging me to my feet.

He pulled me close into him, and kissed me passionately, his tongue almost reaching my tonsils as if he was determined we become one through our mouths. Abruptly he broke off and grunted at me, "I want to fuck you now. So bad! So bad!"

I was caught up in the heat of the moment, so I responded, "Fuck me now, and fuck me silly." Upon hearing this, Paul grabbed me by the waist and lifted me bodily into the air and onto the bed. I landed with a thump, more turned on than I could ever remember. Harder too. Paul didn't even want to wait to undress me, content to just rip my panties off of me, revealing my clit for the first time. Paul gobbled it down; sucking it so hard I thought it might come off. Having never been touched down below it was no time at all before I cried out to Paul, "I'm gonna come."

"Not yet!" he replied, flipping me onto my front. He pulled my hips up so I was on my knee and I buried my head into the pillows as he lined up his rod on my quivering, virgin hole. He roughly thrust into me, his desire overcoming any patience he may have had. I cried out, the unfamiliar sensation both a shock and moderately painful. This cry seemed to remind Paul of the situation and he slowed his pumping to a gentler pistoning. It didn't take long for my initial cry to turn into an insistent moan, encouraging him to pick up the pace and fuck my virgin ass as roughly as he wanted. Paul needed very little encouragement and he resumed his rugged pounding, accelerating towards his orgasm. As the pace quickened and he neared his orgasm the thrusting changed character, becoming shorter but more insistent, his length rubbing against my prostate causing my clit to jump with every pump. With a roar Paul thrust into me one last time, filling my ass with his seed and triggering the most powerful orgasm of my life as my little clitty spurted into the sheets as he collapsed on top of me. I gasped into the bedding, desperately trying to get my breath after the fucking we had just performed. Paul rolled off me and drew in a deep breath. He then turned back to me, the lust still in his eyes and said, "Alexis, that was without a doubt the best fuck I've had with a trans-girl, especially considering that was your first time."

"That was the best experience of my life!" I panted back. "I've never orgasmed so hard in my life." I sank into the pillows as Paul rolled over, drawing me into his strong arms and spooning me. I sighed, the feelings of happiness, security and satisfaction I had never felt before. It was with those feelings I sank into a happy slumber.