All my life I’ve been a hit with the ladies. I started having sex when I was fifteen and since then I’ve never failed to pick up any girl that I set my sights on. I’m pretty good looking and through some stroke of luck I was gifted with an unnatural confidence that women seem to respond to. When people say that women are really looking for confidence in a guy they aren’t kidding (unless you look like a troll).

A week after my 25th birthday I suddenly decided that I was bored with women. I had been chasing tail for most of my adult life and it just wasn’t doing it for me anymore. Sure, sex was still a pleasurable experience and I still managed to have an orgasm when I fucked a girl, but it was no longer the thrill it used to be. Searching for answers, I turned to the internet and the vast collection of porn sites out there. Surely there would be a site that could show me the way to sexual satisfaction once again.

It was right about this time that I discovered your terrific site ShemaleCrawler.com. I was browsing various linklist sites one day, looking for inspiration, when I saw a link to your site. I had heard about shemales and even seen pictures of a few in the porn store and on the nudie rack at the magazine store, but I had never really looked into it in any depth, which is why it was such a delightful surprise when I began exploring your site. I had finally found what I was looking for. Seeing sexy shemales getting fucked, or doing the fucked, immediately connected with my sexual centers and got my genitals tingling like they hadn’t in years. Was it possible all of these feelings had been lying dormant for my entire life? Did I have some latent homosexual feelings that I had never worked out? There were so many questions running through my mind as I tore through page after page of shemale pictures and videos.

Over the first month of my new shemale experience I masturbated on a daily basis to various shemale porn. I had joined two different shemale pay sites that I found on ShemaleCrawler.com. They both had tons of great video content and I spent a few days just downloading stuff to my hard drive. Within a week I had a huge collection of shemale porn and I had begun masturbating every day, sometimes twice. It seems kind of obsessive in retrospect, but I had never been so sexually satisfied. I sat in front of the computer and watched beautiful shemales fuck guys in the ass, burying their dicks deep inside of them.

It was after that first month that I decided I needed to experience a shemale sex first hand. I had become obsessed with experiencing everything about a transgendered girl, including sucking her cock, fucking her ass, and getting her to fuck me. It felt as though it had become an obsession for me, getting to experience this heretofore un-traveled territory. I did some research on the web looking for the best place to find a safe and anonymous partner and I finally settled on making a post on Craigslist.org, that very famous classifieds site. It was a simple post, just a quick blurb about how I was a first timer looking to experience everything with a true shemale.

I wasn’t looking for a guy who liked to wear women’s clothing. I wanted a shemale like the ones I saw in the videos with tits, round hips, and a beautiful ass. I wasn’t really confident that I’d be able to find someone, but as it turns out I got three responses to my message the next day. One of the responses was from a dude who just wanted to give a blowjob, so I trashed that. The other two were from legitimate looking shemales and I messaged them both back asking for more pictures and more information (I also sent them pictures of me). Apparently, my request for more info turned off one of the girls so I only got one response. However, it was an enthusiastic one with lots of pictures and a pretty lengthy biography. The pictures were hot and I trusted this girl enough (God knows why) to setup a tryst at the local cheapie motel. We agreed to meet the next day at 4:00 pm, check in time. I would get the key and then meet her in the parking lot.

The next day I was standing in the parking lot at 4:05 pm, keys in hand, waiting for my beautiful shemale to show up. She pulled up in a new looking Acura, parking in the space next to me. She stepped out of the car slowly, letting her body unfold in a sensual manner. Her pictures had looked good, but I was stunned by what stood in front of me. She had long brown hair, a button nose, big dick sucking lips, and a pair of C cup tits. She was wearing a tight white sweater and a short pleated skirt. In short, she was a picture of perfection, the shemale of my dreams.

I handed her the key and we headed right to the room, wasting no time on small talk. When we got inside and the door clicked she grabbed me by the waist and kissed me deeply, getting right down to business. Her tongue was in my mouth, fishing for my own, and her hands were exploring my body and unbuttoning my shirt at the same time. You’d think I might be scared, but I was turned on immensely. My dick had already hardened and I was ready to go. Our kissing continued and I unzipped her skirt from the side, letting it fall to the floor. My hands immediately went to her crotch where I felt her bulge, a thick package encased in satin underwear. She moaned as I grasped it in my hand, stroking it lightly.

As I continued to rub her crotch she returned the favor, sliding my pants down to my ankles and reaching her hand inside my boxer shorts where she came in direct contact with my throbbing cock. I was harder than I’ve ever been I think, and she moaned in appreciation. I broke our kiss and pulled her shirt off over her head, exposing her braless tits to the open air. I took a bold step and lowered my head to them, taking her left nipple into my mouth and rolling it between my teeth. She put her hand gently on the back of my head, encouraging my actions. I could sense her own head roll back in delight as I sucked on her tits while continuing to massage her shemale cock.

We had barely said a word to each other and I decided, right out of the blue, that I was going to blow this beautiful babe. I needed to know what it felt like to have a cock in my mouth, so I dropped to my knees and pulled her underwear down. When her cock came free it bounced in the air before settling right in front of my face. I had a brief moment of hesitation before I leaned in and engulfed her member, taking half of it in my mouth in one stroke. With me free hand I reached up and stroked her balls, fondling them from side to side while I sucked on her cockhead with my warm mouth. It felt amazing to be sucking a dick, especially one attached to such a beautiful woman.

After sucking her off for a few minutes I felt her pulling on my head, urging me off of her cock. I pulled off of it and looked up at her, afraid that I had done something wrong. I was delightfully surprised when she said that she wanted to be inside of me, to shemale fuck male. I didn’t even say a word; I just crawled on the bed on all fours and presented myself to her, basically begging her to take my ass. She put a condom on and positioned herself behind me, slowly sliding her cockhead into my asshole. In a few pushes she was totally in, thankfully her cock wasn’t very thick. Soon she was thrusting inside of me deeply, burying her cock fully inside of me. I could feel her balls slapping against mine, a feeling that made my throbbing cock even harder.

While she was fucking me she reached around and began stroking my cock, using my precum as a convenient lube. I was so turned on, and so pleasured by the cock in my ass, that there was no way I was going to be able to hold my orgasm. I shouted loudly that I was going to cum and she said she was going to cum as well. She began stroking my cock faster and urged me on, telling me she wanted to see my load on the bedspread. I obliged her, cumming in waves all over the bed. As soon as the first spurt left my cock my asshole tightened around her cock and it sent her over the edge. She began cumming into the condom, keeping her cock buried deep inside of me.

After she finished she pulled out and went to the bathroom to clean up. A few moments later I joined her, washing to dick off and wiping my ass. As she sat on the toilet and peed she said that I could fuck her later, and maybe she’d fuck me again. I wasn’t expecting that, so it was a great bonus. We ended up staying the night together, fucking five or six times in the process. It still remains one of my favorite tgirl sex experiences, although it was only two months ago so I should have a lot more ahead of me. That was a pretty long story, but the point of it was that I wanted to thank you for helping me discover this side of myself. I would never be so sexually free and open if it weren’t for you and I really appreciate it. Thanks.