Caught

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."

Chris laughed, and asked, "what do you say, you think she's into the cock?"

"I guess," I answered, nervously, at the unexpected question.

"Listen, I saw you being a faggot. She leaves the webcam running so I can see her naked from my place, she's into exhibitionism and kinky shit."

My stomach sank. I responded, "oh," and kind of trailed off. I was incredibly nervous and humiliated, but turned on too.

"Relax, finish your beer," he said, noticing how nervous I am. "Since Amber's not here, you can be my bitch for tonight" he asserted.

He pointed his phone at me and was looking at me through the phone, and told me, "are you a faggot?"

"Yes," I answered obediently.

"Quick learner," he responded.

"Don't worry, as long as you're my bitch I'll be the only one with this video," he re-assured.

"Take off your clothes, let me see what I have to work with," he demanded.

I took everything off, one thing after another. When I got to my boxers, I hesitated, but pulled them off after a moment. I was rock hard, despite the humiliation.

"Amber wouldn't be impressed," he sneered. Then he took a couple steps closer to me, and started feeling up and down my legs, and then moved his hands to cup my butt.

"Wow, you feel like you were meant to be a girl."

I let out a slight smile, as this was kind of my aim for at least this night, though not anything like this.

"Let me see you in the clothes, find her stockings. I like stockings."

I hurried into the bedroom, he smacked my ass as I walked by him. He followed behind me.

I pulled out the same panties I wore yesterday and threw them on the bed. I looked through some drawers, but Chris opened one that had exactly what he was looking for, and threw the stuff on the bed, and then left the room. I put on the stockings, garter belt, garter straps and panties. While I did regret ever having gotten myself into this, I did find this incredibly hot. I put the skirt on from yesterday, and a tight blue blouse.

Chris returned with his beer. "Good girl," he said calmly. He put his hands on my shoulders and lightly motioned for me to sit on the bed. He got right in front of me. My heart started beating fast at this point.

He started to undo his jeans. He said, "I take it you've never done this before, right?"

"Right," I answered softly.

"Let's see how good at this you are." He pulled his jeans and boxers down. His enormous black dick bounced out, bigger than what I had anticipated from watching the videos. I had never seen someone else's penis before in real life, so this was all new to me. He was halfway to being hard, from what I could tell.

He looked at his phone, which was pointed at me again, and said dryly "here is Dan's first time sucking penis."

He pulled my head so that his dick was inches from my face. I was so nervous, but felt electricity in my body like I never had before.

I reached for it with one hand, and held it, while licking the top of it with my tongue. It quickly hardened like a rock, and grew even larger. I held it upwards for a second to admire its length. I said, "it really is so big," relieved in some weird way that I could finally offer some sort of compliment.

I continued to hold it up, and took that opportunity to start licking his balls.

"I knew you'd be a good at this," he said.

I swirled my tongue all over his balls, and kissed them, and would put one in my mouth and then the other. I couldn't fit them both in my mouth at the same time. Then I went to licking up and down the length of his penis, and then placed his head in my mouth. I started bobbing my head up and down on it, as much as I could, while stroking it with both my hands. He held the back of my head, and pushed himself forcibly more into me.

"How does it feel to be a cock sucker?" he demanded to know.

I pulled my mouth away from his cock again with some drool connecting us still, just to say, "great."

Chris chuckled. Then he grabbed the back of my head, and pulled me close into him. I tried to take as much of him in my mouth as I could, but started choking, then he let go, and I coughed a little, and got back to sucking. I found myself eager to handle his dick.

He put his phone down. He started to get on the bed with his penis still in my mouth, and I started leaning back until I had my back on the bed, and he was kneeling over my head. He pushed his penis deeper into my mouth and pulled it out a little but only to thrust himself into me quicker and more repeatedly. I started gagging and had drool all over his dick, but was eagerly trying to satisfy him more with my mouth. He just kept penetrating my mouth for a couple minutes, until finally he grabbed my head more aggressively and held it with his dick as deep in my mouth as I could get it for a moment, and then he let go.

He pulled out, and I took a few deep breathes. He demanded, "get on your stomach," to which I complied immediately.

He grabbed a bottle by the nightstand and took off his tee shirt. He rubbed the stuff from the bottle which I'm pretty sure was lube to his penis area, at least from what I could tell in the corner of my eyes. "I have a thing for stockings, in case you haven't noticed. Time for these to come down though," he said, as he lifted up the skirt halfway, and then pulled down the panties. I lifted my mid section a little to make it easier for him. He straddled me, and squeezed my ass, and said, "you have a bubble butt that's meant for breeding, you know that?"

"No, good," I said, not sure what to say.

He lifted up a little, and pulled me up a little so that I was on my knees, bending over in front of him, ready to receive him doggy style. It felt like he was poking me for a split second, and then I felt him slide in me. It was like a shock to my system, and was difficult to bear at first, but at the same time I almost came instantly, it was such an intense feeling. He was very slow initially, and as I became comfortable with the sensation I backed up so that my body was against his, and then started moving back and forward repeatedly. Then he started to take control of the rhythm, and I put my head down on the bed, and grabbed my ass with both hands, spreading myself so he could penetrate me all the way. It felt electric. We went at it for a little while, and finally he pulled out, with a plop sounding, and starting stroking himself right over my face. I opened my mouth wide, knowing full well what was about to happen.

"Eat that shit," he said, just when the first burst came out, and then he let out a moan. I tasted the hot saltiness of it right away. It was much more cum than I had ever produced, but I guess it was proportional to the penis size. When he was about done, I licked the tip of his penis of any leftover cum, not minding that it had just been in my ass.

He picked up his phone again, and I looked up at him and saw him looking at me through the phone.

"Don't stop," he said. "Make sure it's perfectly clean, get your tongue around my balls and everything."

"Not bad," he said.

He put his phone down and started to get up.

"See you tomorrow, bitch."