You've Got Shemale.
This is my first story of this type, so please, be gentle ;) It's a semi-true story, but definitely more fiction than fact, and it will be at least two parts.
I moved to a smaller town when I was in college and found that I didn't fit in at all. I actually got so lonely that I took up a friends advice and joined a dating site.
I had gone through a large number of messaging women on that site to find most remotely near me wanted nothing to do with me. My age range of early twenties had little selection and those that were in that range were surprisingly stuck up. I was actually really surprised and frustrated. See, not to be arrogant, but I'm a pretty handsome guy. I've got a bit of a belly but I worked out for hours a day to keep it off. I also, to be blunt, have some incredible bedroom skill. I'm almost 8 inches but I rely more on my tongue and hands to please the women, focusing on giving them at least one or two orgasms before I penetrate them. In my hometown, these were all qualities that had me a date every week or so. Women had started passing me around so much that I actually was getting tired of it. I actually had decided just before I moved to stop just having sex with women and find someone serious about dating. See, I'd gotten to the point where I'd give a woman a few orgasms and they'd not even give me one. Sex without feelings just didn't do it for me.
Eventually, after yet another rejection message, I decided to broaden what I was searching for. That's where I met Amy. See, I didn't mention this, but I'd always had a fetish for women with a bit "more" to them. It started off with watching women with strap-ons and moved onto women with the real deal. So, just for kicks, I typed Transexual in the search engine. That's when she popped up. I won't lie, she had one very bad profile pic. However, her profile bio caught my eye, we had a good amount in common, and I decided to send her a message.
I was shocked when she sent one back. I didn't expect it as 3/4's of the women I sent a message to didn't reply back and the rest that did were either rejections or didn't last long. I think I dated two people online, and one honestly just couldn't keep up in bed and the other just lived too far away and was too busy. Anyway, Amy sent me a reply, very friendly and we started talking. We got to know each other really well and actually became good friends for a while. She was semi-new to her MtF transformation and was dealing with a lot of people nearby her that knew her as a guy that gave her grief and I, as a very open-minded man, gave her comfort and support. We wanted to meet each other so badly that we agreed to split the cost and meet each other in a state halfway between us. The deal was that she and I had to actually be a couple, no meeting just for sex.
I was incredibly excited and for the months we had to wait until we could do it (the trip, I mean) seemed like it was crawling by. We did nothing via webcam or online but talk as to keep the sexual tension high, so when the trip did come around I was practically hard all the time (I had to wear jeans and a baggy shirt a lot to try and hide my boner). A flight, skip and a jump away, we were in the same city. We met in the hotel lobby, awkwardly hugging at first, but our chemistry eventually overrode the nervousness and it was like we'd been dating for some time. This woman had become a dear friend to me and I couldn't wait for us to be lovers as well.
We held hands as we checked in, and all the way to our room. Energy flowed between our hands like electricity that tingled all over. I honestly felt so excited that I felt like I was going to start vibrating through things, and she was in a similar mood.
We quickly opened our room and, before the doors even closed, we were on each other like dogs in heat. I had my hands in her beautiful black hair, slowly lowering them to her neck, caressing the back of it gently. She moaned against my lips as my hands moved to her shoulders and then kneaded her lower back. She was like butter in my hands at this point. We went to the bed, our lips never parting, and quickly entangled ourselves together as we passionately kissed for what seemed like moments, but actually turned out to be a few hours.
She pulled her head back and smiled at me. "So this means we're a couple then, huh?"
I smiled and stroked her cheek. "Um, well that was the deal after all." I playfully winked. She rested a hand on my crotch and I shuddered a bit as what felt like electricity came from her fingers.
"I just wanted to make sure," She smiled bigger as she unzipped my pants. I helped her take them off and she began to lightly play with my penis with her hands through my boxers.
"I, um, didn't expect you to be this big," She said a little nervously as my erection grew to it's full extent. I didn't know what to say. Despite my fetishes of strap-ons an the like, I'd never had more than a finger, so I had no idea if bigger was better or worse in this case.
"Is it going to be too painful?" I hesitantly asked. I had no desire to hurt her.
"Well, maybe if I suck it off first we can do more later," She said.
"Yeah, I do admit I'm not normally this hard," I explained. "You're just so beautiful, so sexy, and I've wanted to be with you for so long that I'm really excited."
She blushed a bit and resumed stroking my penis. "Thanks. That really means a lot to me."
I smiled at her, and then quickly gasped as she pulled down my boxers in a quick motion and wrapped those sexy lips around my shaft, then quickly took most of it in.
Like I said before, I'm pretty long, but I'm also pretty thick. Women in the past have told me that while I'm not the longest they've been with, I am definitely one of the (if not the) thickest. No woman has ever been able to deepthroat me, but Amy was the closest I've had. She let my cock sit in her mouth while her magnificent tongue stroked from hilt to tip as best it could, and it felt amazing. She pulled her head back and quickly used her hands to cover the areas her mouth wasn't on. Her head rocked side to side on the tip, sending shockwaves through my body. I actually grabbed the sheets, something I'd never done before like this, in passion, pleasure, and excitement.
"You like that honey?" She said as she began to lick my balls.
"Fuck yes!" I almost yelled. No woman had ever done this to me like this. Actually, of the many women I'd been with, only four ever got me to actually come with a blowjob, and even then I'd had to help out a little. This gal got me so turned on and gave such pleasure that I was fighting not to cum so I could enjoy more of it.
"Cum for me baby," She said so sensually I think my dick got harder. "Cum for me, I want your cum now."
I felt the pleasure build to max. I actually fought hard not to do it, but my penis felt that familiar tightening as it prepared to fire.
"Amy! I'm cumming!" I gasped out, clenching the sheets tighter. She quickly pulled her mouth up and let her hand fly up and down my dick. Then she did something no woman had done for me before, she put her mouth all the way down my shaft and let me explode in her mouth. I filled her up so much that I could feel her heavy swallowing while she struggled to keep all my semen inside her mouth.
"That.... was incredible," I said in a voice just above a whisper. She smiled at me, cum completely swallowed.
"I'm so glad to hear it honey," Her face was flushed but delight emanated from it. "Now lets take a shower and clean up, and perhaps get some dinner before we resume part two."
I've almost never needed a break between my first and second orgasm, which frustrated many of my past girlfriends, so it was no shock to me that I was still hard for her.
"You sure we can't do something else?" I asked, flexing my PC muscle to make my penis twitch and Amy actually looked a bit surprised at how much I could move it.
"I didn't say that we couldn't do something in the shower," She winked as she stood up. It was then that I realized I'd just gotten a blowjob from a transgendered woman, and I'd actually see one naked in a bit. My heart fluttered nervously, but I stood up, still hard as a rock, and followed her into the bathroom.