A Trans Beginners Anal Experience

I've been thinking about anal for the longest time now. So many late nights watching porn, pretending and wishing to be in place of those gorgeous women, with long hair, perfect perky breasts and tight round booties, taking cock after cock, I was envious. My girl-cock was rock hard and throbbing when I found a video of double anal penetration. Watching how they take cock deep inside their ass, seeing how their hole stretches effortlessly around huge cocks and gapes hungrily for more when they pull out. The pleasure they must get from experiencing it, I was a mess.

Enough was enough, it was time to experiment. In a horny frenzie, I frantically went online searching for anal training kits, a dildo, lube, I needed it all, in my lust to experience anal for the first time I made sure I ordered everything I might need.

Fast forward a week and my toys had arrived. I couldn't control myself, I was rock hard just opening the packages, knowing what was to come. There were so many different sized butt plugs, a vibrating butt plug, anal beads and other toys in a training kit, a 6 inch dildo that was intimidatingly more girthy than I had expected and plenty of lube. The excitement flooded over me as I looked through everything.

That evening I stripped naked, caressing my body as i did so, running my hands over my long soft smooth legs, up to my now 36 DD chest, squeezing my breasts and pinching my nipples as I went. Igot myself comfortable in front of a mirror. It had to be infront of a mirror, I wanted to see what my tight little ass hole was taking as well as feeling it. I lubed up a finger and rubbed it teasingly around my freshly shaved, silky smooth ass hole, it felt incredible to tease my hole like this. I felt like such a slut. The cold from the lube made me tense my butt but it soon warmed and I relaxed into the circular motions I was making around my hole.

When I felt ready, I reached for the first toy, the smallest one I had, I lubed it up and slowly pressed it against my eager hole, it felt uncomfortable as I pushed it further and further inside myself. It was small, only the size of a finger, but still that seemed to be difficult for me. After a few minutes I was struggling to get comfortable, how did they do it? I wondered. How did these women take such huge cock almost effortlessly but here I was struggling with something so tiny? A few more minutes and I gave up. Upset with how things went, I packed up my toys and put them under the bed. Maybe another day things will go better, I said to myself.

It took over a month for me to try again. At this point I was gagging for it even more than the first time. I had a new curiosity for anal fisting which had developed over recent weeks. I identify better watching trans porn and watching trans women getting fisted and double fisted brought an overwhelming pleasure to me. The complete submission to allow a mistress to destroy your asshole, pushing her whole fist or even both fists deep inside, leaving a sloppy, ruined, loose hole when she's done. I was a whore, a complete slut for the content I was watching, wishing even more that one day that would be me, I was a submissive slut that wanted to be used.

That day I tried again, I got my toys out, exposed my slutty little ass and went for it. I started with the small toy like I had done before, lubing up my hole and pushing it inside me. This time was different, I didn't give up. I spent an hour playing with myself, until near the end I was furiously thrusting this finger sized toy inside myself.

Over the next two days I repeated the process twice each day. My ass was a little sore but getting looser, I could feel it opening up to me more easily.

On the third day things started to get interesting. I started with the usual, lubing my hole and then inserting my pathetically small toy. This time was different though. After a while I decided I would insert my finger. I pushed it all the way inside myself. My ass squeezed around it but I managed to relax myself. I could now feel the inside of my ass, the walls were smoother than the skin around the outside, it felt good. My mind was racing with how dirty I was being and I was so proud of myself for it as well. I almost wished I had an audience to watch me, that could encourage me as I teased them with what a filthy slut I was. I removed my finger and lubed up a butt plug, this was quite a bit bigger, four and a half inches with a bit more girth. I relaxed myself so I could insert it easier. Wow! Feeling the stretch it gave me when I pushed it against my hole was crazy, it made my ass feel sore immediately but I persisted, I managed to get it about three quarters of the way in before I stopped. I played with this for a while before I called it a day, satisfied that I was making progress.

Another couple of days playing with my original toy, fingers and butt plug and things were going well, I could now fit two fingers in my ass and feeling my hole stretch around them brung so much pleasure to me. But it was time to take another step. I picked out another butt plug after the usual play with other toys, this one was slightly shorter but more girthy. I had previously lined all my toys up so I could see what I could use to slowly improve myself until I got to the dildo, I had a long way to go yet I thought to myself.

This butt plug provided a bit of resistance, I could feel it stretching my ring as I slowly pushed it in. I was nervous. But my persistence paid off, after alot of back and forth it finally nestled inside of me, I felt full. I laid back and tried to give myself a few minutes, relaxing my ass around the plug, gently running a lubed finger around the base of the plug and feeling my stretched hole, it felt nice, almost like a little tickle as my finger danced around the rim. I thought to myself about how much of a whore I was and that this was just the start, how if I really wanted it I had to keep this up and go bigger and bigger. If I wanted to take cock and get fucked I had a long way to go. It had been a fantasy of mine for a long time to get fucked and feel a man ejaculate inside me, I wanted to feel his shaft pulse inside my ass as he was balls deep, releasing his cum deep inside. Oh what a feeling that must be. The thought of him pulling out to expose my gaping hole, cum dribbling out and down my leg. He would own me and I would do anything he said. If he wanted me to suck his cock clean or if he fed me his cum from my ass, I would lap it up like a good girl, his personal little slut. I had to keep practicing to make my fantasies come true.

At this point I was beyond horny, pre cum was leaking from my tiny girl cock. I had got myself so worked up with all the ass play and the fantasies running through my head. But my ass had had enough for the day, so I pulled the plug out with the intention of stopping.

Now is where things got interesting. As I got up and went to clean myself off my eyes locked on the dildo, that six inch realistic looking cock, it looked so good, so enticing. I couldn't help myself my mind was in such a filthy place that I decided to grab it and lay back down. Let me just see if I can put the tip in or what it feels like, if I can even get close to accepting it. I used lots of lube, both on my ass and on the dildo. I was breathing heavily now and getting pretty sweaty. I was rock hard and my mind was hell bent on wanting more. I very slowly pushed the head of the dildo against my ass hole. I was amazed! This cock was girthier than anything I'd taken but my hole was loose and relaxed and to my amazement the head slid in with only a little bit of a push. I continued to push slowly. OH MY GOD! I felt everything stretch open, this cock was filling me up and it felt fucking amazing.

My ass widening and stretching around this beautiful shaft was like a dream come true. I pushed it deeper. At this point I had about two thirds of the dildo inside me. I was in absolute dream world, I was shaking, I was in such a place of pleasure, overcome with the absolute bliss of my ass being filled with cock. I slowly pulled it out, the feeling unlike anything I have ever felt before and something I will never forget. I knew this was my life now, I knew this is what I wanted. To be an anal slut and to fucking love it, getting off on fucking cock, the pleasure is incomparable with anything I've ever experienced. I spent a few minutes fucking myself slowly. Oh my god I just can't describe the pure joy and feeling I got from being filled with cock. My mind was a mess, I was drunk on the whole experience.

After a few more minutes I had finally had enough. I pulled out and cleaned up. But my mind is still racing. I can take a cock! Where can I get cock? I need it! If I can take that dildo and get such overwhelming pleasure then I want the real thing. I day dreamed for hours about being fucked by any men that wanted a go. On my back with my legs over my head with cock after cock going balls deep inside me. I thought about a dogging spot that I knew of close by me, imagine if I went up there, imagine it being full of dirty old men just waiting to fuck, imagine getting tied up to a tree and pumped full of cum all night long, a complete submissive cum whore. Getting my tits and ass played with for everyone's pleasure, god I'm such a whore.

And I'm still thinking about it right now as I sit here writing this, in fact it's got my clitty rock hard again. Where do I go from here, what's next?