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.