Hi there, I just wanted to write in to let you know how much I like your site, ShemaleCrawler.com. I discovered it about two months ago when I was browsing for some shemale galleries and I’ve used it almost every day since. I love how I can always find something new on the site and how everything is high quality. I’ve been into shemales for about three years now and I wanted to share with you the story of my first time with a hot shemale.

I grew up feeling sexually confused. I knew I wasn’t gay, and yet I found myself dreaming of dick sometimes. These were pretty torrid dreams, but when I woke up and thought about being with a guy I was totally turned off. Not only that, but I was confused because it didn’t make any sense. Strangely, I had these dreams while I was dating girls, and having sex with them, so I seemed to be attracted to both sexes, at least certain parts of both sexes. Then one day I was browsing the internet, looking for something suitable to masturbate to, and I came upon a shemale TGP site that had tons of picture and movie galleries. I instantly found myself attracted to the girls on the site, especially the ones with big tits (what can I say, I’m a breast man).

Ever since that day I’ve been obsessed with shemales. Nowadays I don’t masturbate to anything else and I can’t bring myself to date women anymore. It just isn’t the same if she doesn’t have that rare combination of female beauty and a dick. It’s fair to say I’m addicted to shemales, something that began in the flesh about two and a half years ago. I had been looking at shemales on the computer for about six months and I was hungering to be with one in the flesh. I had actually been planning on doing something for about two months, but it’s not as easy as you might think to find a shemale to be with; they’re not exactly coming out of the woodwork.

I decided that I would try something simple and I signed up for an adult matchmaking service that specialized in pairing guys with shemales. It was pretty cheap for the membership and I soon had a few pictures of myself uploaded and a profile filled out. After that I did a search for shemales in my area and it turned up quite a few eligible ladies. Some of them seemed to be just guys dressing in drag, which I really wasn’t interested in. However, there were a fair number who were clearly women that just happened to have penises. These ladies had breast implants, curvy hips, soft faces, and soft skin; basically all the features you associate with a woman.

That first day I sent out emails to five shemales and went to bed excited at the possibility of meeting someone over the weekend. That night I dreamt in depth of being with a shemale, screwing her in the ass, sucking her shemale cock, having her suck my cock, and much more. I awoke with a huge boner and a crazed sex drive. Without even stopping to piss I rushed to the computer to check my email from the matchmaking site. Two of the shemales had responded positively, asking to know more about me and sending along a few pictures. One of them hit me right away as someone I’d be interested in. In the picture she sent she was wearing a short pink dress that ended about halfway down her tights. She had what looked like C cup breasts, very curvy hips, and long, straight black hair. She also had a sultry look on her face that got my cock stirring in my pants upon first glance.

I decided I would only email this sexy tgirl back and take my chances that she would be willing to meet over the weekend. In the email I told her a little bit about myself, when I had discovered shemales, what had prompted me to try and find someone, etc. I included a few more pictures of myself, including one of me shirtless, in case she was concerned about that kind of thing. After I was done I headed out to the kitchen to make some breakfast. After I finished my cereal I went back to the computer and, much to my delight, I saw a reply to my email sitting in the box.

She wanted to come over on Saturday at 3:00! I couldn’t believe my luck. Two days from now I was going to be having sex (hopefully) with a beautiful shemale babe. I emailed Jamie (she finally gave her real name in the last email) back and told her I was looking forward to a great Saturday.

I spent the next two days coasting, just daydreaming about what Saturday would be like, and whether or not it would be the same as all the fantasies I had created in my head. Would she be good at oral sex, would she let me fuck her ass? Would I want to suck her cock if she asked? I didn’t know the answer to any of these questions, although I hoped it was yes for each.

Finally, the big day arrived and I made I was as primped up and ready as I could be. I wore a nice pair of slacks and a fancy shirt, two items that rarely made their way out of my closet. I ran some gel through my hair and shaved, making myself as presentable as I had been in years. When the doorbell finally rang at 3:00 my heart jumped. I was immediately nervous, excited, and a little bit scared all at the same time. I made my way down the hall and pulled the door open to be greeted by a ravishing looking Jamie standing in the hall. She blew my mind.

Jamie was wearing an amazing black dress that ended right above her knees. The cut was low, it ran down into her cleavage and I could see the sides of her beautiful breasts. It didn’t appear as though she was wearing a bra, so she must have had a nice boob job to keep those tits so perky. The dress was sleeveless and made from a silky, nylon type fabric that clung to her body in all the right places.

“You look stunning Jamie. Please, come in,” I said, beckoning her inside and down the hallway with my hand. “Would you like a drink?”

“A glass of wine would be lovely if you don’t mind,” she said in a voice that was surprisingly feminine. I didn’t know what to expect in that department, but I was pleasantly surprised.

“Why don’t you have a seat on the couch and I’ll be right back with two glasses of wine.”

I quickly poured two glasses of wine in the kitchen and headed out to the couch. When I came into the living room Jamie was sitting on the couch and inspecting the photos on the coffee table. Her legs were crossed and the dress was riding up, revealing some of her luscious thighs. My cock stirred in my pants. I sat down next to her and presented her with the glass. We toasted to find happiness in a relationship and each took a generous sip. Jamie’s free hand came up to my face and gently rested on the side of it, getting ready to say something.

“You’re a very attractive man. I was turned on the moment I saw your picture. I just knew that we would connect with each other. I’m glad I decided to come over today,” she said.

“Me too Jamie. I knew from the moment I saw your picture that you were the one for me.”

After those introductions we continued to drink our wine and chat with each other. I asked her when she had decided to live life as a shemale, and she said she knew from the moment she was born, or at least as far back as she can remember. She had been living full time as a woman for 10 years now; right before college she made the change. As we talked Jamie kept running her hands over my body, stroking my legs, touching my arm, running her hand through my hair. When we finished our drinks and put them on the table she went for it, placing her hand right on my crotch and leaning into me.

“I want you, badly. I need your cock in my mouth. May I suck you?”

How could I refuse? I answered by unzipping my pants and pulling them off, along with my underwear. My cock was already hard and Jamie went to work immediately, kissing my deeply on the mouth while she stroked my shaft. Soon I was hard as a rock and she lowered her head, taking the tip of my dick into her mouth. It felt absolutely amazing, and my hands immediately found her tits and started groping them through her dress. She moaned in response and sucked hard on my cock, sending waves of pleasure through my crotch. I couldn’t believe how skilled she was with her mouth, it was just amazing. It was warm, wet, and the suction she managed to apply almost made it better than fucking a pussy felt.

“That feels amazing Jamie. God you’re a good cocksucker, damn,” I said, overcome with desire.

“Do you want to try sucking my cock baby?” She asked, looking up at me with her beautiful brown eyes.

I was caught in a moment of indecision. I honestly didn’t know what I wanted. I had dreamed about being with a shemale for so long now, and while I had never sucked cock before, it seemed foolish to be with a shemale and not use her cock for something.

I was caught in a moment of indecision. I honestly didn’t know what I wanted. I had dreamed about being with a shemale for so long now, and while I had never sucked cock before, it seemed foolish to be with a shemale and not use her cock for something.

Jamie pulled her head out of my lap and did me one better, pulling her entire dress off and slipping her panties down her legs. She stood before me totally naked and it was a sight to behold. Her breasts were indeed a lovely C cup, standing out perfectly from her chest. She had a flat tummy and great hips that flared out in the classic female style. It was lovely to see such a womanly body with a cock attached to it. Speaking of her cock, it was already hard and it looked to be about 6” long. It wasn’t too girthy to fit in my mouth, which was good because I was nervous enough as it was.

“Sit down baby, I want to suck your cock,” I said, getting on my knees in front of the couch.

Jamie sat down and moved her shemale ass forward, presenting her cock to me. I was now on my knees in between her legs with her cockhead just inches from my face. I reached out with my right hand and grasped her dick, stroking the full length up and down. At my touch Jamie leaned her head back and moaned. She even thrust her hips up to meet my strokes, obviously eager for contact. While Jamie’s head was still back I leaned in and enveloped her cockhead in my mouth, swirling around the sensitive underside with my tongue. I pressed hard into it with my tongue and let my spit leak out of my mouth to lubricate her shaft. While I worked on her head I used my hand to jack the shaft, moving it up and down quickly.

Jamie was really getting into it now, moaning like crazy and thrusting her hips to try and push more of her cock into my mouth. After a minute I relented and opened my mouth wider to let more of her shaft inside. I began to bob my head up and down on her, trying to take more of the shaft in my mouth on each downstroke. Eventually I managed to get about ¾ of her shaft in my throat, which I considered quite an accomplishment for my first time.

“Oh baby, you’re so good at this. You’re so good at sucking my cock. Your warm mouth feels amazing on my shaft. God baby, keep sucking me so good,” Jamie said, keeping a hand on the back of my head to guide my movements.

I kept on sucking Jamie for another five minutes before she pulled my head up and whispered in my ear “I want you to fuck me now. I need your cock in my ass.”

I’m not one to turn down that kind of invitation so I grabbed the condom I had stashed in the coffee table drawer and quickly pulled it over my cock. When I turned back to the couch Jamie was lying down on her back and she had her legs spread open. She was fingering her asshole and stroking her cock at the same time, moaning quietly with her eyes closed while she did it.

“Are you ready for me Jamie?” I asked.

“Oh yes baby. I even cleaned myself out before I came here, hoping that it would end like this,” she said as she pulled her finger out of her ass. It was clean as a whistle. “Now come fuck me stud.”

I crawled on the couch and positioned myself on top of Jamie. My cockhead met her asshole and I pushed lightly, trying to ease myself in. Jamie sucked in a breath and tensed her body slightly, preparing for the painful pop of entry. I continued to push and Jamie used her hand to help guide me in. The lube on the condom was helping and after a few hard pushes I was in. It felt amazing, like a lifelong fantasy come true. At first I just let my cock rest there, soaking up the feeling of being in her asshole. Then I continued forward, burying the other half of my cock in her until I felt my balls resting against her flesh.

Jamie grabbed my head and pulled me down to her mouth where she planted a passionate kiss, snaking her tongue into my mouth. Her erotic move spurred me on and I began thrusting into her ass, pushing my dick deep into her bowels and then pulling it almost all the way out again. I repeated this process over and over, our bodies slapping together in a hot symphony of sounds.

“Your ass is so tight Jamie; it feels so good to fuck you.”

“Pound me harder, fuck my shemale ass as hard as you can. Fuck me so hard. Fuck me until I cum!”

Jamie was really getting into it now and it seemed like she was getting close to orgasm even though I wasn’t even touching her cock. I was getting close to my own orgasm and I followed Jamie’s directions and took to fucking her harder, pounding that tight ass with all the force I could muster. The sound of my body slamming against hers combined with the tight feeling of her asshole was erotic enough to push me over the edge.

“I’m going to cum Jamie, I’m going to blow my load,” I yelled.

With one final thrust I buried myself deep in Jamie’s asshole and let loose with volley after volley of cum, filling the condom with sticky juice. At the same time I felt a blast of something hit my stomach and I looked down to see Jamie cumming as well, her semen landing on my stomach and hers.

“That was amazing Jamie, simply amazing,” I said, bending down to give her a gentle kiss.

“Yes, it certainly was. We’ll have to do that again sometime,” she said, smiling up at me.

“What about later tonight?” I suggested.

She responded by pulling me in for a huge, my cock still in her ass, although now it was deflating. Jamie stayed the night at my place and we ended up fucking three more times. It’s still the best night of shemale sex I’ve ever had in my life. I guess the first time really is the best.