The Babysitter Takes Over

By sissysherry2

“I know your secret.”

These were the words that I had both dreaded and longed to hear from my babysitter Teri.

Let me start at the beginning. I am single and have a couple of kids at home who aren’t quite old enough to be on their own when I have business obligations. I share custody with my ex, which left me to be with another man, who happened to be black. I get the kids during the week, my ex-gets them over the weekend. Teri had answered a babysitting ad for watching them after school and sometimes during the evening. She is the answer to an older man’s dream- 18, hot as hell, very athletic body. I noticed that lately, she had been wearing tight clothing; perhaps to make her more attractive to me. Whenever she would leave, I would take the next opportunity to go to my bedroom to masturbate.

On Saturday, after dropping off the kids for the weekend, I answered a knock on the door. It was Teri.

“Hey Teri, you know the kids aren’t here. I don’t need you this weekend.”

“Oh that’s where you’re wrong, you do need me,” Teri said.

She walked in without asking.

I didn’t say anything as she just walked in; she is just so damn hot.

She said, “Let me get right to the point. Last night I got curious about you, so I let myself into your bedroom.” I froze and just about passed out. One of my fetishes is dressing in nighties, and I hoped she hadn’t found them.

“I know your secret,” Teri said and smiled. “Now let’s go upstairs and play!”

Therefore, we went upstairs and into my bedroom. Teri sat on the bed and got her phone out.

“Now you are going to do whatever I tell you, right?”

“Wait, do we really have to do this?” I protested.

“Oh come on, you KNOW you want to do this. You want to be my bitch, don’t you? I can tell by the way that you look at me. Now take off all your clothes.”

I decided this was my chance to play out one of my fantasies, so I decided to go along. I took off my shirt first.

“Omigod, check out those man boobs. They’re bigger than mine, you know. Play with them for me, bitch.” I complied, and she started giggling. “OK, now for the pants, take them off.”

Again, I complied. Then Teri walked up to me and felt my tits. She put her hands on my boxers and pulled them down. That’s when the real laughing started.

“Holy shit! Look at that micro dick. No wonder your wife left you for that black guy! Moreover, you can’t even get it up with a hot chick right in front of you. Are you a sissy?”

“Y-Yes,” I stammered.

“I knew that already because last night I went to your dresser.” Teri then recreated the scene by walking over to my dresser. The teen pulled out one of the baby dolls that I had hidden at the bottom of the drawer. It was the pink one. “I found this, put on this nightie for me, sissy.”

Teri handed me the pink baby doll nightie, and I slipped the panties on first. I didn’t think I had much of a choice. It was a g-string that barely covered my dick. She then told me to pose and started taking pictures on her phone.

“Now for the top,” Teri said.

I complied and felt the smooth fabric cascading over my body. It fit perfectly, and I was instructed to pose for the teen as she took more pictures on her phone.

“I think I’ll call you ‘sissy sherry’ from now on, bitch,” Teri said.

Then she told me to go into the bathroom.

“I noticed that you have some of that disgusting body hair. I bought a bottle of Nair, and I want you to spread it all over your body. I want it on all over from the shoulders down, including your chest, underarms, arms, back, shoulder, around your clit and your legs.”

While we were waiting for the Nair to take hold, she took more pictures of me and instructed me to smile for the camera. She told me to talk like a sissy and captured a video of me telling her my sissy name. After fifteen minutes she had me go into the shower and wash it all off. I watched all my body hair go down the drain. I stepped out of the silky shower smooth. She handed me a bottle of feminine moisturizer and had me spread it over my entire body. I must admit it felt fantastic!

“Time for makeup; let’s get you nice and pretty,” Teri said,

She had me sit in front of a mirror and applied foundation, blush, lipstick, mascara, eyeliner, and eye shadow. I posed once again for pictures and videos.

“You probably know this, but I own your sissy bitch ass now, don’t I? Tell me you are now my property.”

“You own me, Mistress Teri! I am your sissy slave,” I said.

“Good little bitch. I’m now going to take control. I’m going to start by having you sign on to your bank accounts, then leave the room. I’m going to change the username, password, and all your contact information. I’m going to link them to my bank account and take what I want. I will also do that to your 401K account and your other investment accounts. We are going to have so much fun playing. I’m going to invite some of my friends over for a little party tonight and don’t you dare embarrass me, bitch!”

I couldn’t see my way out of this so I agreed, not knowing what the future held. However, I was excited to find out!


“Ok bitch, I’m going to invite my friends over tonight for a party. I’m going to text them an invite, and I want you to do it. Now go over there and start talking. And you better make it good, or I’ll post the pictures on my Facebook page,” Teri said.

I went over to the corner and started talking while Teri got her phone out again and pointed it at me. I spoke in a high girly voice and a lisp. “Hi, this is ‘sissy Sherry,’ and I’d like to invite you to a party tonight at my house. It’s gonna be so much fun! We are gonna play truth or dare, talk about boys and maybe have some guys come over. Please come over as soon as you can.”

“Not bad, bitch,” Teri said. “I’m going to send it out now; I’ll put your address in the text. When they get here you will do everything—and I mean everything—we tell you to do. Now we’ve got to get ready.”

I spent the next hour cleaning up the house. I set up the living room and cleared out the middle of it. She told me to freshen up my makeup, especially my lipstick. I vacuumed, dusted, and sprayed some feminine air freshener all around. Meanwhile, Mistress Teri was on her phone most of that time; she looked up and giggled at me every once a while as she talked. I had a very uneasy feeling about what she was doing. Teri had a very evil look in her eyes. At one point, she had me pose for a picture while doing a courtesy.

Just as she hung up, the doorbell rang, and Teri told me to answer it and to act like a sissy. I was in my pink baby doll nightie and fully made up, but since she had so much on me, I did as I was told.

“Hi and welcome! Come on in,” I greeted her guests.

Five teen girls came in laughing at me as they came into the living room. They were all dressed in provocative clothes, and of course, they all had cell phones in hand.

“Girls, this is Sissy Sherry, and I own her ass,” Teri proclaimed. “We’re going to have a lot of fun at this party, and she’s the guest of honor. I’m having a surprise visitor coming later but for now, let’s have some fun with her.”

Teri told them that I would do whatever they told me, so they should ask away, and the more humiliating, the better. “Let’s see a striptease,” they shouted.

One of the girls started playing ‘Style’ by Taylor Swift on her phone. I didn’t really know what to do, but they started screaming at me to start stripping. Therefore, I seductively danced for them. I took off the top of my nightie, and they told me to play with my tits. I did so as they bounced around. The girls hollered insults at me as the top part of my nightie was thrown into the group of girls. That left with just the g-string on.

“Now take off the panties,” they screamed, and I did so.

I took them and whirled them around my fingers. The laughing was immediate.

“Omigod, she’s hung like a grape,” one of them said.

I was forced to stand there while they all took pictures of me naked. They told me to tuck my little dick between my thighs, so it looked like I had a pussy. One of them got the whole striptease on video.

“Now let’s see just how much of a sissy she really is,” said Teri.

She told me to get on my knees; she had gotten on a strap-on harness with a huge black dildo attached. I was told to start sucking and immediately complied. I licked the balls and ran my tongue up and down the shaft. I loved the feeling as I slid it into my mouth. I then started sucking on it. Of course, the girls were capturing the whole thing on their cell phones. I was able to deep throat it with only a little gagging as I kept sucking. Teri dick slapped me while laughing at how pathetic I looked.

“Now let’s warm the bitch up. Get over there to that couch and assume the ‘sissy slut’ position. That means lean on the couch, stick your ass up in the air, and arch your back. And hold your ass cheeks open, bitch.”

After doing so, I felt something slippery on my ass and then the unmistakable feeling of being penetrated. Teri started fucking me hard while the girls held me down. I was really starting to enjoy the feeling as I submitted to her. She hammered me from behind for quite some time. I moaned like the cheap slut I have become. However, I did wonder what she meant by ‘warm her up?’

Just then, the doorbell rang, and I was told to answer it. The girls told me to put my nightie back on and walk like a girl over to the door.

I opened the door and standing there was my ex-wife’s black boyfriend.


All of a sudden, it became quiet in the room as I was instructed to open the front door. There were half a dozen teenage girls, including my Mistress Teri, watching and waiting. There I was, in my pink nightie, fully made up and hairless on my body. There stood my ex-wife’s lover.

“Well what do we have here?” he sneered. The contempt in his voice was unmistakable. “I’m not surprised from what your ex-wife told me about you. Even though she left your sissy ass, I’m going to call her your wife just to degrade you. Come on, bitch, get inside.”

He is very tall, probably six foot three, and built like a linebacker. He could kick my ass in a second if he wanted to. He would consider it a waste of energy. He was a pure Alpha bull, and I knew I was a pure beta sissy.

“Teri, this is a hell of a great plan, girl,” he said. “I would love nothing better than to put this sissy bitch in her place but to make money off it is even better. Sherry, show me that tiny clitty dick. Your wife told me it’s the smallest she’s ever seen and you were shitty in bed. You couldn’t get it up and hadn’t had sex n years. Well, she’s making up for lost time now, bitch.”

I pulled my panties down and lifted up the top of the nightie. Everybody laughed at me. The black stud then started groping my tits. He took my boobs out from the nightie and felt me up. It was so degrading.

Mistress Teri said, “I know this is gonna be sooo fun. OK let’s get started. Sherry, first I’m going to need you to sign this. Don’t bother reading it just sign.”

I complied; my curiosity and my predicament gave me no choice. Something inside me said not to, but this whole thing was so exciting!

Teri continued, “OK, Melissa, I’ll need you on the laptop to run the main feed. Ann, Caitlyn, and Cathy, you run the cameras and make sure you get her face. Chelsea, you run the website and make sure we keep getting paid customers and take requests. How many do we have so far?”

“About three hundred,” Chelsea said. “Not bad for a first-time audience, Teri. At $30 for the hour, that’s about nine grand, but we can sell it after too.”

“OK, I’ll direct. Let’s get started,” Teri said.

It hit me like a ton of bricks. They are making a porn movie, and I’m the unpaid star. That was what Teri had been doing on the phone while I was getting the house ready for the party. And I probably signed a release just now.

“OK, Sherry, on your knees bitch. I don’t think I need to tell you what to do but watch for cues. I undid his belt, unbuttoned his trousers, pulled down his zipper, and his pants fell to the floor. I didn’t need instructions on what to do next. I pulled down his boxers. It seemed the boxers kept going forever as his massive black cock flopped out.

“I know you want to worship that dick, but you have to earn that privilege,” the black bull said.

He turned around and presented his muscular ass to me. I instinctively started licking and kissing his ass. I stuck my tongue between the crack and moaned. My tongue made its way to his asshole, and I worshiped it. I stayed there for a good ten or fifteen minutes. Every so often, I would look around, and I saw one of the girls pointing their phones right at me. They were using their phones as movie cameras just inches from my face.

He then turned around so I could worship his cock.

“Suck it, bitch. Deep throat the cock that has given your wife such pleasure,” he said.

I started sucking his cock with relish. I could barely fit it into my mouth. The dick slapped me a few times, and I continued sucking. After a while, I could hear him grunt and moan. I felt his cock tense up then explode. I swallowed some, but he sprayed a lot of semen on my face.

“Damn, bitch, you give good head,” my ex-wife’s black boyfriend said.

Teri then chimed in, “Hold on, one of the viewers is offering two hundred and fifty dollars if you piss in her mouth.”

He pushed me away and told me to open up. A strong rush of pee gushed into my mouth. I instinctively swallowed, and he stopped for a moment. He started peeing again so not a drop was wasted. He finally finished and told me to smile at the cameras and kick my lips.

“We just got another request. One of the viewers offered five hundred dollars to whip her ass,” Chelsea shouts.

He took off his belt and starting whipping me. I lost count at twenty hard lashes. One girl was in front of me and told me to look into the camera. Another was behind me filing my ass as it beet red.

Mistress Teri then shouted, “OK, the hour is up. Chelsea, how much did we take in?”

“Just over twelve grand, Teri, and the feedback were excellent; they want to see Sherry get fucked next time,” Chelsea said.

“Oh, they’re definitely gonna see that,” Teri said.

to be continued…


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