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Click here"Yeah, I didn't even mean to stay here last night. I have work in a few hours, and
I don't want to be late."
I hadn't intended on staying, either. After all the drinking we'd done last night and then, of course, all the fucking, I and Alex had both been unable to resist the urge to sleep. As Alex finished dressing and grabbed her phone, she smiled at me.
"Well, I gotta get going now," she said, with a bit of a sigh.
"Right...it was...fun..."
She nodded, then turned to walk out of the room but, I stopped her. "Hey uh, do you...do you wanna hang out sometime?"
I almost couldn't believe myself, that I was asking but, I was really hoping Alex would say yes. She looked at me for a moment, clearly as surprised by my question, as I was.
"You do realize what we did last night, right?"
"Uh...y-yeah," I nodded.
"And that I'm not actually a girl? I mean, I'm just technically a gay dude who likes wearing girly clothes and shit. You're okay with that?"
Obviously, I must have been okay with it, considering I'd sucked his cock last night and let him fuck me in the ass. It was clear to me now though, the next morning, that Alex wasn't as feminine as he'd tried to pretend to be the night before. He was talking in a slightly deeper voice than before, and while he still looked a little like a girl, I could tell without having to see his dick that it was actually a guy. I didn't seem to mind, though.
I'd had fun the night before, and I didn't feel like it was just the alcohol that had made me enjoy myself with him.
"Yeah, I'm okay with it," I replied finally.
Alex hesitated for a moment, then smiled. He stepped forward and leaned down, giving me a kiss on the forehead.
"Get my number off my cousin," he said.
"I'd love to see you again."
Later that day, I called Jamie when I got home and asked if she could give me her cousin's number. She seemed surprised that I was asking for it but, also seemed to know without saying, that I'd definitely crossed a few lines with Alex last night.
In the end, Jamie had nothing against me and Alex hanging out and sleeping around together; she was, after all, just my ex. Hooking up with her cousin even seemed to help me move past my breakup with Jamie, and helped us become close friends.
I and Alex went on to have a sort of friends with benefits relationship, that lasted for a good couple of years before he moved away to another state. I would never forget the times we'd had together though, and we kept in touch on the internet, remaining good friends. I had had some of the best sexual experiences of my life, with my ex-girlfriends cousin.
- COMMENTS
ruwildover 5 years agoGood writing is good writing no matter the content. Even though I'm not into cross dressers you still did a good job with this story. I'm glad you referred to Alex as a girl, it helped me with the read and it's good that you're willing to try on new stuff.
Anonymousover 5 years agoLove the CD element. would be fun to see the psychology and emotional toll having sex with a man in drag would have on a straight man.
WhiskeyIsGoodover 5 years agoAuthorI don't mind crossdressers BUT, I do think Literotica should make it a separate section from transgender. As you know, the majority of my stories involve transsexuals and I tend to get a lot of people suggesting that I make my male characters dress up...that's just not something that I am into. I did write this story with the second main character being what MOST would consider a crossdresser but, he/she maintained the dominant role with the male character...that's not something you see very often, in most of the other crossdressing stories on here. In any case, I'm glad you enjoyed it. Not my usual cup of tea but, I'm trying new things on here...don't expect me to write about sissies or anything though lol
WhiskeyIsGoodover 5 years agoAuthor"I and Alex."
Yeah, I screwed up there, and I guess the program I use for editing didn't pick it up. Sorry about that.
Emirusover 5 years agoCross dressing isn’t my thing. I would like authors of all crossdressing stories to say so at the beginning. I think that Literotica should separate transsexual stories from cross dressing but that’s just me and it’ll never happen.
To me shemale fucking male is much the same as female fucking male with a strap on. If that makes sense. It’s how the story is told that matters. I’ve only published one transsexual story so far but there will be another one shortly.
I thought you were going to continue with them meeting again where Alex worked in which case I would have walked away without rating it. However you didn’t do that so I chose to look on it as a shemale/male story, took in the actual storyline, and as such enjoyed it. Plus you made it clear at the end that there wouldn’t be a sequel which I agree with because it is a stand alone story.
There’s a limit to how you can tell a story like this and you did ok. So you’ve got a 5.
