I worked for years at a place with this girl named Amber. Most everyone else where we worked was very open and social, but Amber and I both kept to ourselves for the most part. I did not know her well, but we were very friendly to each other. She was slightly on the thick side, nice and curvy, with red hair. I was surprised one day when she asked me to watch her cat while she was gone for a couple weeks. I happily obliged. I wasn't sure, but I thought maybe this would be my way of getting to know her a little, and possibly asking her on a date when she gets back depending. She told me she'd only need me to feed and water her cat after work each day, and change the litter box as needed. She told me she figured I'd be more reliable than most people she knows, and she doesn't have family or anything in the area.
After the first day she was gone, I headed to her apartment immediately after work. Her bedroom door was open, right in front of the entrance to her apartment, and I could easily see some handcuffs on her bed. It made me chuckle a little, I guess she really trusted me or something, she didn't bother to hide that at all. I quickly took care of everything without snooping anything further.
The next day however being a little braver I walked into her bedroom to see the rest of it. I saw all her dirty clothes on the floor, and wanted to try a fantasy I had for the longest time and never really had the opportunity to try - that was to crossdress. I'm normally the type of person that would try to avoid tampering with someone else's stuff like this, but it had been a secret fantasy of mine that I had almost completely forgotten about until this opportunity. I took off my clothes quickly and set them in a neat pile. I felt strange being nude in a strange place. Then I found a pair of red panties on the floor which fit decently enough. It made me feel sexy and horny putting them on, and knew I had to go a step further. So then I found a blue bra, which I managed to get on easily, but obviously they didn't serve any function without any breasts to hold. Then I found a skirt, something I had probably seen her in at work. I pulled it up and could barely fit it on me, but I managed, and it was just a little extra short on me. At this point I started feeling up and down my legs, how feminine I felt. I laid down on her bed and pulled up the skirt so I could masturbate. I came quickly, and it was a lot. I felt guilty about having done this in her apartment though, and quickly cleaned myself up and changed back into my clothes. I made sure there was no evidence whatsoever. Then I finished what I came to do - take care of the cat.
Later that night, I thought about that experience. I shaved my legs, pubic area, everything as much as I could, so that next time it'd be more realistic. I masturbated again finding it so hot.
The next day I went over eager to wear Amber's clothes again. This time I walked in though, and found the television on to my surprise.
There was a person in the living room getting up from the couch. I asked, "Amber?"
I saw a man about my age appear, dark black skin, tall, and slightly muscular build. "Nope, she told me someone was here to watch her cat, I guess that's you - Dan, right?"
"Yeah, " I said nervously.
"I'm Chris. Me and her get together from time to time, you know. You work with her, right?"
"Yeah," I said, wishing I had more to say.
He grabbed a couple beers from the fridge, and handed me one, "here."
I took it, and we both sat on the couch. I was curious why he was there, but didn't want to ask. I was just glad he didn't show up yesterday unexpectedly.
After taking a couple sips, he faced me, and asked, "want to see something?"
"Sure," I said, hesitating.
He pulled his phone out of his pocket and opened it. He swiped and tapped a few times, and then held it so I could see it. He played a video of him banging Amber doggy style. I could see her ass bounce against his body repeatedly. Then I realized she had those handcuffs on behind her back.
"She's an absolute freak, but you'd never know it," he said.
He tapped something on his phone a couple times, and then showed me a video of her gagging on his dick. Both were very hot scenes, and I moved my arm to try to conceal that I was getting hard.
"Like what you see?" he asked, knowing full well why I moved my arm.
"Yeah," I replied, honestly.
In the video, he pulled his dick out of her mouth, and I could hear her say in the video, "it's so fucking huge."
