Chapter 2

At school that week, Danny and Jessica acknowledged me in the hallways and that was really nice. Jessica didn’t stop and talk to me, but she gave me a knowing smile and a wink. Christian and Christina are in the same grade that I am but they didn’t’ share classes with me and they didn’t act any differently when they saw me in the hallway.

Anytime I saw Christian, I smiled because I realized that his older sister knew that he liked butts and for some reason knowing that secret amused me.

I kept thinking about Jessica sexually and how she was so casual about offering me a blowjob. I wondered if it was a test to see if I would go for the offer just to see how perverted I was. It felt like that at times. I couldn’t imagine a girl like her going down on a scrawny kid like me.

I also kept thinking about Mrs. Morgan and how sexy she was. She hadn’t made a pass at me but she seemed so open to exposing her daughter to me. I had so many perverted fantasies about HER that week that I felt guilty about it. She was a married woman my mother’s age! Yet, she turned me on almost as much as Jessica did.

At least, I hadn’t fantasized about getting it on with Christina. She was cute and my age, but she had really nothing to do with any of their naughty games and bets. I think she only begrudgingly tolerated it.

“Hey Mike,” I got a call from Jessica about a week and a half later. I didn’t’ even know she had my number. I reminded her that my name was Mark.

“I know silly, it’s so easy to bust your balls. Hey, can you come do another babysit tonight? I trust you after that last time.”

WOW! Can I? I had ZERO plans that evening, and I was more than happy to do it. “Great! Same right?” she asked.

I was so nervously enthusiastic I almost said I’d do it for free. I stumbled over my own words before I finally answered yes.

“Great, can you come now? I know it’s last minute,” she said.

I told my parents I’d be babysitting tonight. “I really don’t like Carrie Mason taking advantage of you with these last-minute requests. Does she think you have no life?”

“I really don’t, Mom,” I chuckled that I had zero social life anyway. I nearly ran to the Mason’s house.

Jessica greeted me at the door. She was fully dressed. My first thought was that she invited me over just to see if I was going to be this eager pervert and then she could laugh at me.

“Carrie’s in here,” she invited me in right away without asking any questions. She told me to be quiet. I was shocked to see Mrs. Morgan bound by her wrists to her ankles on the couch with rope. She had rope around her boobs and a blue ball gag in her mouth. Her entire pussy and asshole were spread and exposed. Her pussy looked slippery – I didn’t know that women got ‘wet’ at that point in my life. I had only ever looked at pornography and when I saw Jessica’s pussy it didn’t glisten the same way that her mother’s pussy did. I assumed she had rubbed baby oil on her pussy lips and around her anus.

Carrie’s family stood around quietly tittering and whispering. They smiled at me when I walked in, and Danny held a finger up to his lips to indicate I should be quiet. Her kids were obviously not freaked out by their mother’s nudity. I would have completely lost it if I saw my own mother this way.

“Well Mom, you win again! You were right, your babysitter showed up, but he was afraid to come inside. I guess you get to come play Mini-golf and eat Olive Garden after all!”

Carrie murmured a satisfied groan into the gag and seemed to insist that it be removed. Her kids laughed. Jessica removed her mother’s blindfold “Wait a minute, he’s here! Too bad, so sad, sucks to be you!!!” she teased her.

Carrie’s blue eyes darted over to me, and she looked worried and nervous. The other kids laughed as Jessica plucked the ball gag out of her mother’s mouth. She didn’t remove it entirely. The gag from her mouth had spit dripping off of it and rested on her chin.

“It’s wrong that you tease your mother like this!” Kendrick groaned.

“NOW you say that?” Carrie laughed at the irony of it. Apparently, she had bet that her husband would protest the bet a lot sooner.

“I really don’t appreciate that you two make bets about when I am going to suggest that you have gone too far with your degrading bets. This is the most extreme one yet,” Kendrick protested. He could have forbidden his wife to make bets like this with her daughter. He seemed to protest but I think a part of him enjoyed watching them.

“Nonsense, the most extreme was when I tied mom to a tree outside and left her exposed by the hedges so our neighbor could see her!”

“One of these days you are going to get us reported to the HOA or the police, and then we won’t be laughing,” Kendrick warned.

“Dad, look at mom. You don’t think a cop would laugh if he saw her big fat butthole spread out like that?” Danny chuckled at his mother’s predicament.

“She is still your mom,” Kendrick chastised his son for showing no respect for his mother.

“Actually, tonight she is just Carrie. That’s why she needs a babysitter. No authority to tell us what to do, and can’t bitch or complain until noon tomorrow,” Jessica reminded everyone.

“Enjoy it while it lasts, because I’ll catch up what I missed out on at 12:01 tomorrow during lunch!” Carrie assured her daughter.

“We’re not all crazy,” Christian warned me. “Just my mom and sister,” he snickered. Then he asked to hurry up and get to the mini-golf.

“Go on and get in the car, I’ll go over some last-minute things with the babysitter that I hired,” Jessica grinned as the rest of the family went to their garage.

“You can gag Carrie if she gets too talkative,” Jessica told me right away. Carrie kept her mouth shut and listened. “You can blindfold her if you want. Obviously, you cannot untie her or loosen her bindings.”

I wondered what I’d do in an emergency. I got a little nervous. I assumed the chances of a fire breaking out were pretty negligible and the unlikely scenario was just my anxiety over seeing a grown woman naked for the first time.

“At 9pm, I have a bowl of cold, plain oatmeal prepared sitting out on the table. Please spoon-feed her. Saying here comes the airplane open up the hangar is totally optional,” Jessica teased her mother playfully.

“What about something to drink?” I asked.

“I know you were a good babysitter,” Jessica seemed pleased. “See that, Carrie? He’s concerned about you getting enough liquid. I am glad you asked, Mark,” she addressed me by my real first name. “There is a baby bottle in warm liquid. I’ll show you how to hold it so that she can drink. I’d like her to finish two bottles tonight! One at 7 pm and one after her meal.”

“No Jessica, please,” Carrie groaned. I wasn’t sure why that would be a problem.

“You have to stay hydrated! Carrie,” Jessica sounded mockingly concerned about her mother’s well-being.

“Don’t let her sleep. If she tries to nap just pinch, her nose or these lovely little pokey things on her chest. They are perfect handles,” Jessica pinched her mother’s nose and then both of her nipples.

Carrie didn’t protest the offer. I was shocked that they would let me touch her nipples.

“I’ll be texting you and I expect pictures every five minutes. Mom makes boring faces; would you have any problem tickling her if I asked you to?” Jessica asked me.

Carrie protested she didn’t refuse. It was more like she said that was unfair.

“Unfair? You had the babysitter change my pissy diaper and you didn’t even know him. I am just lucky he wasn’t a lecherous little pervert like Christian,” she told her mother. Carrie didn’t argue it any further. Jessica asked me if I had any other questions.

“What should I do if your mom does have to use the bathroom?” I asked. Carrie’s eyes grew wide with nervous anticipation of her daughter’s answer. It was a perfectly reasonable question from my perspective. The mention of a pissy diaper had made me assume that I might need to put a diaper on her as well.

“Excellent question,” Jessica looked menacingly at her mother. Carrie cringed and shivered. “Obviously, Carrie is bound on the couch, and she isn’t allowed to complain. I suppose she could ask you to bring a Tupperware bowl in here and let her drop a deuce?”

“Jessica!” Carrie sounded aghast at the suggestion.

“Would you rather ruin the carpet?”

“I’ll try to hold it until you come home,” Carrie suggested.

“You’ll be on the couch all night, and that’s a long wait until morning,” Jessica said.

“Can you let me lay out in the backyard please?” Carrie begged.

“I could, but you agreed to this bet, and I’d be here right now where you are if I lost, so no. I think you can beg your babysitter to bring a glass or a Tupperware bowl if all that delicious milk starts to feel really heavy in your bladder!”

“Payback is going to be a bitch,” Carrie promised her daughter as Jessica ignored her and walked out the door.

“Oh, and mom offered to take care of you last time you were here. I won’t be making the same offer, but she still owes you one, so feel free to make use of her. She has nothing to do for at least four hours,” Jessica instructed me cryptically and wished us a cavalier “Ta-ta for now!”

Carrie didn’t wait to hear the car pull away the way that Jessica had before talking to me. “I really didn’t think you’d be back after you ran out of here last time,” Carrie said.

“I am sorry you lost the bet. I didn’t know you bet against me,” I apologized. I felt bad that I cost her more humiliation.

“It was the double or nothing. If you hadn’t shown up, I would have had to ride like this in the backseat and if I got to join the family I am sure my daughter would have made something super humiliating.”

“What was the original bet?” I asked Carrie was far more forthcoming and not as sassy as her daughter with her answers.

“You’ll think I am crazy, but I agreed to be naked and do whatever she told me for 24 hours. I can’t complain, punish anyone, or bitch. I really don’t think I do that very much, but hey, it’s a vacation for my kids for 24 hours. I can accept when I lose a bet. The double or nothing was thinking you wouldn’t come and naturally I have to do whatever you tell me until she gets home.”

My dick nearly shot off a full load of jizz the moment she told me she had to do anything I told her.

“I assumed Jessica told you that on the way over here?” Carrie asked. She seemed surprised that I was shocked by that news. “Obviously, you can’t untie me or make you give my ATM pin code or something.”

“Anything?” I asked again in disbelief.

“There isn’t a lot I can do from here on the couch, but if it’s within my power to do then yes. My husband gave me permission.”

I assumed she meant sex. “Is that what Jessica meant by taking care of me?” I asked. I was so shy that I didn’t want to come right out and play with this toy that had just told me I could do anything I wanted with her without first making sure I heard correctly. She was tied up and vulnerable and couldn’t have stopped me anyway.

“Yes, I promised you a blowjob if you resisted her charms the last time, but you left so fast. I assumed she went down on you, and you didn’t feel like getting a hummer from an old woman like me.”

“No, she didn’t,” I said as my pulse raced and I grew intensely nervous. I could feel my ears turning red from embarrassment as I processed the offer that was made. “I thought the twenty-dollar tip was the bonus.”

“Heavens no,” she laughed. “You are a teenage boy with needs and my daughter is very attractive and sexually promiscuous. I assumed it would take a herculean test of will to pass up whatever she promised you to make life a little easier for her and I was going to at least try to make it right. She told me you were a total gentleman and polite and I assumed she was lying. I thought you’d have dove in and begun mauling me by now. It’s always the quiet ones that are the nasty ones.”

“I wouldn’t do anything that made you uncomfortable,” I assured her politely.

“I am tied wrists to ankles, it’s a little late for me to be comfortable. You can touch me or pinch me. Whatever you want. I won’t break,” she offered. I was still passively shy and unconvinced that I should.

Her daughter texted me to ask for a picture. “Are you already pounding my mom? I Am waiting for the first picture, and it’s been six minutes!”

I told Mrs. Morgan what the text said and she stuck out her tongue and had me text the picture to her daughter. “Would you like me to suck your cock? I owe you one anyway,” she offered.

“You really don’t mind?” I asked.

“You make it sound like you are asking to borrow my car. I am here for four hours; all three holes and my boobs are on display and boobs. You can slap, pinch, tweak, poke, and hump me to your heart’s content. The only thing that I ask is that you really don’t tickle me unless she asks you to do that. I will piss myself if you do it.”

I approached her and tested things by touching her nipples. She smiled sympathetically at how awkward I must have looked. “Have you never touched a girl before?” she asked.

I had touched her daughter. I didn’t think it was lying to say that I had touched a girl. “If you don’t mind some advice, go ahead and put two fingers around my nubs, and then slowly stroke. I am already wet but if you want to tease me and make me really horny, play with my tits.”

“What does it mean to be wet?” I asked as I sat on the couch and played with her nipples gently.

“You are more wet behind the ears than Christian,” she seemed to admire my innocence and find it fascinating. “Do you see my pussy?” she flexed the muscles in her vagina and contracted her pussy lips. A drop of clear sticky fluid fell like morning dew from the center of her pussy and ran down the labia like morning dew along a flower petal.

“Yes, of course,” I said.

“The hornier I get, the more my brain sends a signal to turn on the waterworks and lubricate my pussy. Jessica likes to watch me edge myself for hours and won’t let me cum. It’s incredibly humiliating and frustrating,” she smiled as if she enjoyed that part of it.

“Do you want me to do that to you?” I asked.

“You can keep what you are doing now, or explore me, or pop your dick in me dry. I really don’t have a choice,” she reiterated without telling me what her preference was.

“Couldn’t I get you pregnant?” I asked.

“You are so sweet,” she smiled and said that wouldn’t be a problem. “If you are concerned, I may want you to put a baby in my oven, I’ve got a mouth and a butthole that work too.”

I knew about anal sex. I had seen porn. However, I couldn’t imagine a woman WANTING a dick in the hole that she poops out of. “Will it hurt you if I put my dick in your butt?” I asked.

“That depends. I haven’t seen your pecker yet. If you get me ready with some fingers, I am sure I can manage,” she smiled generously. I unzipped my pants and showed her my hard-on. It was leaking pre-cum.