Caught and Happy to Receive the Punishment

Both of us kept to ourselves for the most part. I worked with a lot of younger, sexually active people but her and I never really spoke of that kind of stuff that much. I didn't know her well and what her situation was, but I was more or less an in the closet bisexual who didn't have much experience to speak of. She was a curvy redhead, not bad looking. 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'd go over to feed and water her cat after work each day, and change the litter box whenever it was needed. I guess she didn't really know anyone else that well, and knew I was probably more reliable than some of the other people we work with.

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 investigating 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 of mine. I took of 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. Then I finished what I came to do - take care of the cat.

The next day I went over to do the exact same thing. This time I walked in though, and found the television to my surprise.

The person in the living room got up from the couch, and started walking towards me. I asked, "Amber?"

I saw a man about my age appear, dark black skin, tall, and slightly muscular build. "Nope, you know she's out of town. She told me someone was here to watch her cat, I guess that's you - Dan, right?"

"Yeah, " I said nervously.

"I'm Chris, nice to meet you. Me and her get together from time to time, you know. You work with her, right?"

"Yeah," I said, another boring response I felt. I felt odd she didn't just have him take care of the cat as I started to refill the cat's food and water. The litter box hadn't changed much since yesterday so I was pretty much done. I hesitated wondering about Chris. He was back to watching the television. I was curious why he was there, but didn't want to ask. I was just glad he didn't show up yesterday unexpectedly.

When Chris saw me stand there for a second, obviously done with everything, he faced me. "Want to see something?"

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, in 1st person point of view. 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. She leaves the webcam turned on on the computer so I can watch her nude any time I want, she's kind of into exhibitionism."

My stomach sunk a little hearing this, although he was calm. I knew what was coming but wasn't sure how it was going to play out.

"And relax, but you know I saw you being a faggot. I could tell Amber, but I don't think that's necessary."

I didn't say anything. I was incredibly nervous, shaking, humiliated, but turned on too.

"What did you see?" I simply asked.

"Everything. It was in the background on my computer and I wasn't paying attention to it. I didn't even know you were going to be there, but I saw some movement and then figured I'd watch, and what a show. Let me see you in those clothes right now, change into them."

I took off my clothes in front of him, letting them fall on the floor. He held his phone pointing at me, and said, "I'm going to record this. Don't worry I won't show it to anyone."

I hated being recorded, but went through with it anyway. I quickly put on the same clothes from yesterday, in addition to a small, tight blue blouse.

My dick was obviously hard, and he obviously noticed and said, "wow, looks like someone likes the abuse," he responded.

"What do you mean?" I asked. I was beating around the bush - very turned on, but still uncomfortable.

"Watch this," he said as he did something on his phone again, and then faced it towards me.

A video played of Amber struggling to take his whole penis in her mouth, with tears coming from her eyes and everything.

"While Amber is out of town do you want to be my white bitch? It's been a while since a white boy has blown me."

"I don't know," I said.

"Have you been with a guy before?"

"No, have you?," I asked back.

"One or two," he responded. "Do you want to?"

"Yeah," I mumbled.

"Good," he said calmly. He started to undo his jeans, and pull them down along with his boxers. An enormous black cock came out, bigger than what I had anticipated from watching the video.

"What do you want to do with this thing?" he asked.

"Suck it," I said quietly.

"Don't be shy, say it," he demanded.

"I want to suck your big cock," I responded, hoping this was what he was looking for.

He laughed and started to push me downwards by my shoulders, and I started kneeling so that his cock was inches from my face. I was still 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 was semi-hard initially, but quickly hardened like a rock, and grew even larger. I held it upwards for a second to admit its length, and took that opportunity to start licking his balls.

"I knew you'd be a good little bitch," 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.

"What are you?" he asked.

"What do you mean?" I asked, holding his penis for a moment.

"A cocksucker faggot," he answered.

I pulled my mouth away from his cock again with some drool connecting us still, just to say, "I'm a cocksucker faggot."

He started motioning himself towards the edge of the bed, and I backed up on my knees to stay with him, careful with my teeth.

"Alright let's see what this faggot can handle."

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. At this point my head was against the bed, and he just kept penetrating my mouth for a couple minutes, until finally he grabbed my head and held it with his dick as deep in my mouth as I could get it for a moment, and then he let go.

"Get on the bed," he demanded. I obeyed of course. He opened the nightstand by the bed and took off his tee shirt. He grabbed a bottle which looked like lubrication and rubbed it on himself while turned around. He turned back around towards me and got on the bed with me. He kissed my neck, and motioned his hands on me to turn me around. I obliged, and bent over full of anticipation. I pulled up the skirt just a little and pulled down the panties just enough. He smacked my ass a couple times, and then started concentrating on the penetration that was about to happen. "You have a big bubble butt ass that's meant for breeding," he said.

It felt like he was poking me for a split second, and then I felt him slide in me. 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.

"It's not over yet," he said. I was quite worn out, but happy to continue. He laid down on his back facing away from me, his penis now semi-hard. He spread his legs. He started recording this on his phone again.

I instinctively moved my face back towards his penis. He moved my head lower with his hand, so that my tongue could just slightly reach his anus. "Eat it, faggot," he demanded. He was very clean and everything, so I gladly swirled my tongue all over his asshole and tried penetrating it just with the tip of my tongue and everything, and he seemed to enjoy it.

He started stroking himself, and so I started licking his balls again.

After some faster stroking, he pulled my head onto his dick just in time for his cum to splatter against the back of my throat. It wasn't as much this time, but I still loved every bit of it.

"Time to get out of here," he said. He quickly put on his clothes. The second I started to change however, he said, "Amber isn't coming back for almost two weeks, just wear what you're wearing. No one will see you."

"I don't know," I said, nervously.

"I want to see you go to your car in that, just do it," he asserted.

"Okay," I submitted.

We walked outside together, fortunately it was dark outside.

"Catch you tomorrow," he said.

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Caught and Happy to Receive the Punishment