Chapter 1

“Are you the babysitter?” the woman greeting me at the door turned up her nose when she saw me. I usually get that reaction because I am a guy, and most people are expecting a woman. I posted an ad in a local Facebook group asking to make extra money babysitting and she even spoke to me on the phone. She KNEW I was a guy.

“Yes Ma’am, I am Mark. I spoke to you on the phone,” I replied politely. My parents had only recently started letting me babysit. I take care of my little brothers all the time and I have experience with babies even though I am 14. I told her all of that on the phone.

“You seem a little a young. I am not sure you can handle this,” she seemed uncertain. I heard her son Danny Mason in the living room laughing. He’s a football star and a senior. I know of him, but I doubted he knew of a scrawny freshman like me.

He urged his mother to hurry up because they were apparently late to go someplace. It sounded like the family was laughing about some joke in the house and they were obviously in a very good mood.

“You are sure you have taken care of a baby, IN diapers before?” Mrs. Mason asked. I was glad she was being so careful. The request was kind of short notice. I think I only got the job because I live a few blocks away and I was willing to take it at the last minute. I assured her that I had. “I want you to change Jessica at 9 pm whether she needs it or not. I have a bottle for her floating in warm water on the sink, make sure that she drinks it ALL tonight before 9 pm. We call it a “Ba-Ba”,” she said.

“Yes, Ma’am,” I assured her that would be fine.

“Don’t let her sleep! Whatever you do! If she does, she will be cranky all night long,” Mrs. Mason warned me. That was relatively unusual. Most people wanted their babies to sleep whenever they were tired but I understood that she probably wanted Jessica to sleep all night long so she could get some rest.

“Yes Ma’am, I’ll pick her up and carry her around if she starts to sleep,” I offered.

“I doubt you can carry her,” the woman sounded downright insulting. I am a bit scrawny, but I can certainly carry a baby.

“I promise I won’t drop her, Ma’am. I will be extremely careful,” I said.

“You can probably just talk to her, to keep her awake, but NO television, and she stays in the living room!” Mrs. Mason insisted. “We’ll have you back again if you do a good job.”

“How old is your baby?” I was under the impression she was in diapers. What exactly was I going to say to a BABY that they would understand? I assumed she wanted me to just babble nonsense to keep her awake. I’d do it. They were paying 20 dollars an hour which was much more than I normally charged. I didn’t ask for that. She offered it. Mrs. Mason had asked me if I had experience with babies and her next question was whether or not I had a sense of humor. I told her I did, and she offered me eighty bucks for four hours of work on a Friday night. I jumped at it.

“She’s sixteen,” Mrs. Mason urged me to follow her into the house. I assumed she meant 16 pounds. I was shocked to see Jessica Mason. A popular junior at my high school on the couch. She was topless wearing only a diaper and white knee-high stockings. She had a necklace around her neck. She was sitting on the couch sucking her thumb and looking somewhat angry.

I didn’t know that she and Danny were even related. I had never thought about it before. I never saw them together at school. I also didn’t know either of them lived here. Jessica looked at me and rolled her eyes and didn’t even try to her perfect tits. My eyes went straight to those stiff nipples on her chest.

I barely noticed when Mrs. Mason introduced me to the rest of the family. They were dressed to go out. “This is my husband Kendrick,” she said. He seemed like a typical businessman. “This is Danny,” she introduced him. He fist bumped me. “This is my son Christian and my other daughter Christina.”

They were identical twins. The family seemed amused over my stunned reaction, and either laughed, snickered or teased Jessica.

“Goo-goo, gaa-gaa!” Jessica replied sarcastically after pulling her thumb out of her mouth.

“I apologize for not telling you my daughter’s age on the phone. She lost a bet, and she has to pretend to be a baby until tomorrow. I thought you might think I was a prank caller,” Mrs. Mason apologized. She seemed relatively good natured, but I think the person who enjoyed Jessica’s humiliation the most was her mother.

“These bets are getting out of hand, Carrie,” Kendrick said. “If you are uncomfortable, just say so,” Jessica’s father asked me.

“I doubt he can hear you over the sound of Jessica’s boobs,” Christina laughed. Everyone noticed that I was stunned. I don’t think they were surprised but I blushed anyway when I was called out.

“You want me to babysit your teenage daughter?” I asked.

“She is our baby tonight,” Kendrick shrugged.

“I do expect you to change her diaper at nine, make sure she doesn’t watch TV, use her phone or leave the living room, and stays in character. You should feed her a ba-ba in about an hour. Is that too weird, Mark?” Carrie asked.

IT WAS VERY FUCKING WEIRD. However, I was going to get a chance to sit with a hot girl for four hours. A HOT topless girl.

“As long as you don’t mention this to my parents?” I winced as I said it out loud. I didn’t want to lie to my parents, but I also knew that I probably shouldn’t be doing this.

“What happens in the Mason household, STAYS in the Mason household,” Danny patted me on the shoulder. “My mom and sister have been doing these bets for a long time. We’re used to it. I totally get that you are freaked out, but it is totally harmless fun.”

A popular kid talked to me. He obviously recognized me from high school. That alone was very satisfying by itself. I pretended that this was perfectly normal and not weird at all. “No, it’s very weird, dude. I wouldn’t blame you if you ran out of here screaming like we were the Addams’s family. You were the double or nothing,” Danny explained.

“Mark doesn’t need to know everything,” Carrie shushed her eldest son and explained that Jessica had asked for double-or-nothing. Jessica lost that bet too and had agreed to spend the night with a babysitter IF her mother could find one willing to actually babysit her. “I don’t want you to feel bad about it. Jessica knew that I might find a local babysitter who would put up with her for four hours.”

Jessica sucked her thumb rapidly, pouted and furrowed her brows angrily. “Mom, I know him from school though. He might tell everybody”

“What is it you say when I lose? Oh yes, too bad, so sad. It sucks to be you. You knew the risks. You can talk but you have to use baby talk!” Mrs. Morgan chided her daughter. “Mark, will you promise what HAPPENS in our house STAYS in our house? If not, I may have to call your mother. I do know where you live.”

“I won’t tell a soul,” I said. I was thinking that I doubted anyone would believe me anyway.

“No-ba-ba, will bah-weeb you, any-way,” Jessica lisped what I was thinking in her baby voice. I had to smile because that was funny.

“Good, you have my cell phone in case Jessica breaks any rules or tries to give you a hard time,” Mrs. Mason reminded me. “She can do anything a baby would do, but nothing a teenage girl can do,” she added.

The kids seemed inclined to urge their parents out the door. Apparently, they were going to a new movie and to eat at Applebee’s. “Oh, and Mark,” Mrs. Mason said as she went out the door “No sex. If Jessica promises you anything tonight OR later and I find out, I’ll ground her, and you won’t be invited back.”

I got an instant boner. Jessica’s mother had just casually mentioned the possibility of sex with her daughter.

I stood there and stared at Jessica on the couch for a long while. Jessica didn’t make eye contact and continued to suck on her thumb and slouch. “Are you just going to stare at my tits ALL night?” she finally asked as she pulled her thumb out of her mouth.

“I am sorry,” I said. “You have really nice, uh boobs,” I replied awkwardly.

Jessica rolled her eyes. “If you tell a soul at school, my brother Danny may think this is hilarious, but I am pretty sure he would be happy to put you face down in a trash can and make you wear a diaper at school while you waddle down the hallway. Do we have an understanding?”

I nodded. I didn’t intend to tell anyone. I barely had any friends. I would love to have had someone who might believe me. I was tempted to snap a picture just to have proof that this weird thing happened, but I knew that would freak her out. “Aren’t you supposed to talk baby talk and suck your thumb?” I asked.

“Look, I can suck my thumb all night and talk to you like some kind of mumbling baby, OR I can suck something else before my parents come home if you can be cool. Which do you prefer?”

Did Jessica Mason just casually offer me a BLOWJOB? Holy crap. BOI-OING! I had to adjust my pants and sit down on the couch.

“Not now, creepy! You don’t have to sit so close,” Jessica chastised me for joining her on the couch and I moved to a nearby chair. I didn’t agree to her deal, but I didn’t say that I wouldn’t do it either. It was incredibly tempting. What were the chances I’d be invited back anyway?

“What was the bet?” I asked.

“Ooh, you will never believe it,” Jessica got incredibly excited and animated when I asked her. It was like she was suddenly thrilled to talk to me. I didn’t recognize the sarcasm until she said “It was a real NUNYA and it went like this,” she flipped me the bird and pretended to stick it up her ass by lifting her leg and then pulling it out and flinging what I could assume was imaginary poop at me.

I blushed so hard.

“I am just trying to make conversation,” I replied politely.

“I don’t know you. I don’t like you. I would never date you, Mike,” she said.

“Mark,” I corrected.

“Whatever,” she shrugged. “You are my babysitter. You get to stare at my tits. Okay? I have to live with that. The question is can you be cool while my parents are away? and the answer is that I’ll be that cool with you. You seem like a boy in desperate need of having a drainage unblocked and I give great head. What do you say?”

I received a text on my phone, and it vibrated. I rarely get a text. It was not the most opportune time. I felt like I was at a crossroads. I could agree to look the other way and experience my first real blowjob. I could also say that I will do the right thing. I wanted to do the right thing, but a blowjob. That was life-altering.

I assumed the text was from my mother to ask if I found the Mason’s house and if everything was going okay. She tends to worry about me. It was from Mrs. Mason.

“Did she offer sex?” was the text.

“What did my mom ask?” Jessica rolled her eyes. I think she could tell by how I cringed when I got the question that it was from her mother.

“It just says nunya,” I joked.

“Har-har,” Jessica grimaced. I think she secretly thought my reply was funny though. Her respect for me went up ever so slightly.

“Yes,” I wrote back.

“What did she offer?” she wrote.

“Oral sex,” I felt strange texting her mother that her daughter offered to suck my cock. I tried to make it sound a little less vulgar.

“I know that can be hard to resist. I’ll make it worth your while to say no. I have Kendrick’s permission. Tell her that I knew she would do that, and that I am disappointed.”

I said exactly what was on the phone.

“Tell her that I said,” Jessica replied and then switched to a baby voice “Me don’t know better. Me baby.”

I wrote what she said verbatim. Her mom texted a high five, a peach, and a devil emoji. When I told Jessica she said that meant a spanking and looked grumpy.

“Tell her that I expect you to send pictures every five minutes. Get her bottle and put it between her boobs. She can’t use her hands.”

She wanted me to take pictures of her daughter and text them? Jessica groaned but didn’t refuse. I brought her bottle that had been prepared in the kitchen. It seemed like it was probably warm milk.

Jessica curled her lip and when I told her she had to put it between her tits she complained that wasn’t part of the deal. She tried to hold it between her tits by squishing them together and sucking on the nipple and told me in baby talk to text my mom and let her know it was impossible.

“Make her lay on her back in the living room, legs up, bottle between her boobs and suck it. She can raise her butt off the carpet if she needs to. She has to drink the entire thing. She can only crawl, no walking,” Mrs. Mason said.

I told Jessica her mother’s instructions. The teenage girl cussed her mother but obediently slipped off the couch holding the nipple of the bottle in her teeth. She lay on her back with her legs spread and started sucking the bottle as it rested between her tits. She stopped long enough to tell me that I had BETTER delete these pictures at the end of the night and if even ONE makes it on the Internet she’d remove my testicles from my body, blend them up and feed them to me in that baby bottle.