This is a story with extreme humiliation. Gay sex, submission and more. If you don't want that, please go to the next story :)
When I returned down to our living room, Karen was already having a drink and relaxing in the sofa. I kissed her hi and asked her about the trip. I was so afraid that she would see that I had the chastity still on or there were still leftover of the guys cum on my face. I turned bright red, just thinking about that but she didn't notice. I opened a beer and she asked me about my weekend.
I decided I should tell her that I got to know Kevin, our neighbor over the weekend. Told her that we had beer earlier and he seemed like a nice guy.
"I thought you didn't like him?" she asked.
"That was before I got to know him some more," I lied. I still didn't like him, but he was now my master, and I needed to be able to keep that going.
"He is what, 15 years older than us, and not in very good shape, I must say," she remarked. "But that doesn't matter, does it. I am happy you made a friend in the neighborhood."
We finished our night with a long chat. She went to bed, and I told her I would be up soon, I just wanted to clean up before. She smiled at me, happy that I would do that and went upstairs.
While I cleaned up, my mind wandered to the change in my life for the last 24 hours. From a married man to a sissy, from a guy who have never had a gay experience to being bukkake by four man and send home with they're cum on my face. To be pissed on and dressed up in a sissy dress while cleaning my neighbor's house. While thinking about all this, I found my cock tried to grow in that little cage. I wasn't sure how I would explain that to my wife. When she wanted sex, I just hoped Kevin would have freed me up.
As I was heading up stairs, my phone pinged. It was a message from Kevin. "Slut, be here 9 in the morning, get in uniform and wake me up with a blowjob." Attached was a short video of me getting cum on my face from one of his friends.
I wouldn't get much sleep that night.
It turned out to be quite hard sleeping with the cage on. I was waking up hurting from my cock trying to grow, hurt from the ring around my balls. But at least, I got a few hours in before I woke up just before 8 in the morning. My wife was still sleeping. I quietly left the bedroom, took my bag with my uniform on and headed downstairs. I poured myself some coffee and waited. I was supposed to be there at 9, I knew I had to do it. I just hoped that my wife would sleep through it.
Just before 9, I walked over and entered. I changed in the kitchen before entering his bedroom. There he was, snoring, sound asleep, naked. He was lying on his back, so there was nothing that prevent me from doing what I was supposed to do. I climbed in bed, between his legs and slowly took his soft cock in my mouth. It was musky, I felt hit grow a little in my mouth before I started to suck on it. Slow at first and I could hear him grunt, move a little so I dropped it out. I felt my head quickly follow his movement and get the cock back in my mouth. He was now fully erect, and I sucked him for 10 minutes before he woke up. I knew that he had woken up when he grabbed my head and forced it down on his cock. I was gagging as he fucked my mouth.
"Good morning sissy," he said as he kept using my mouth as his masturbation tool. I tried my best to hold on and kept sucking and slurping on his cock. Suddenly, I could feel him stiffen up and without a warning, he filled my mouth with his cum. He held my face down as he drained his cock down my throat.
"Yes, that was a good morning wake up sissy. We will do this more often. Now clean me up and go make me some coffee." I licked the rest of the cum from his now shrinking cock before he stood up and walked into the bathroom. I could hear the shower running.
I fixed a coffee, still dressed like a maid and when he came out, he took the mug and went into the living room. "Join me sissy."
He told me that last night was a little disappointment for his friends. "To have the maid run out on us in the middle of the night, was embarrassing for me. If I can't control my slave, then I lose all credibility with my dominant friends, you understand that don't you?" I nodded.
He stood up with his phone up. "I want you to apologize to them". He hit record.
I wasn't sure what to say, but he just looked at me with a angry look.
"Hello. I want to apologize for my behavior last night. It was something that I could not control. I hope you accept my apology."
Kevin stopped the recording and shook his head. "That was pathetic. But we will see, maybe they take pity on you and accept. But I doubt it."
He told me to change and go back to my house. He would be in contact later.
When I came back home, I still had the taste of my neighbors cum in my mouth. Karen was downstairs having a coffee. "Good morning love, were have you been?"
I stammered that Kevin needed some help.
"That early on a Sunday morning. That is a little rude, isn't it."
It was difficult lying to her like that. "No, I don't mind. It was a quick job."
"What was the job?"
She wanted to know more; I had to think quickly. "Just move a closet that was in his way in the garage."
That seemed to settle her curiosity.
We talked about the rest of the day. She told me that a friend of her was in town, and she wanted to grab a coffee with her downtown and if I would mind. I told her to have some fun. "I am just going to hang around the house, just relax a little".
Around noon I saw my wife drive off. I knew she would be out for a few hours. My wife's car was still visible when my phone rang. It was Kevin.
Kevin: Hey sissy. Where was your pretty wife going?
Sissy: Hello Sir, she just went into town, meeting a friend for a coffee.
Kevin: Good, then you have some time on your hand to compensate for your lack of servitude last night.
Sissy: What do you mean Sir?
Kevin: I am texting you the address of Justin. He didn't accept your apology, and your present is expected there now. It will take you about 15 minutes to get there. You better hurry, he is expecting the maid to come.
He hung up. The address came.
I didn't have the opportunity to plead with him. It was outside, another house. I was so scared, what was expected of me there.
I dressed up and then put on a long coat on that covered my sissy look. I had the wig with me. On the way, I was so nervous. This was something that we had talked about, not exposing me but here I was, going to another house, dressed in a sissy maid outfit, not knowing what would wait for me there.
As I approached the house, I noticed that it was a small house, basement and then two floors on top of that. It was in the middle of the neighborhood and busy street. I parked my car. I didn't know if it was the basement or the top floors. I fixed the wig on my head before running up the stairs. I took my chances and rang the bell on the middle floor.
Justin opened. He just stood there, waiting.
"Hello Sir, Kevin sends me," I managed to say.
He still just stood there, in silent. I didn't know what to do. Finally, he spoke. "This is not what I ordered," he said as he started to close the door.
"Wait, Sir, please wait." He looked around before removing my coat and show him my maid uniform.
He smiled. "That's more like it. Hand me the coat," he ordered as he ripped it from me before allowing me to enter. I was sure so many people have seen my exposure, but I just kept looking inside. Hopefully no one would recognize me.
He sat down at the kitchen table. "So, you want to make up for being such a poor slave last night?"
