Date Night Chapter 12

I dutifully kept Jimmy abreast of each new development via text. A typical exchange went as follows:

Me: Abigail is completely intoxicated and babbling incoherently.

Jimmy: lol dumb fucking whore

Me: She's literally fucking her own stuffed animal.

Jimmy: stupid goddamn skank

Me: lmfao

Whenever I concluded these exchanges, shame and guilt consumed me. There were many nights I cried myself to sleep. Yet still, my morality could not compete with my lust. Observing my brilliant daughter transform from a prodigy to an imbecile fueled my insatiable arousal. The more Jimmy degraded her (with my implicit approval), the wetter I became. I couldn't wait to see how low she, or I, would go.

Entry 12

November 11, 2023

Dear Diary,

I awoke to a feeling of wetness between my legs. It took me a moment to remember I was wearing a diaper. In a panic, I cried out, "Waaahhh!!! Waaahhh!!! Mommmy!!! Mommmmy!!"

Mommy came running as fast as she could. "Don't worry, sweetheart- Mommy's here." I relaxed knowing that Mommy would take care of me. She removed my dirty diaper and wiped me off. She wanted me to wear a diaper to school, but I refused. I was the valedictorian of my class and Harvard bound. Wearing a diaper would be beyond humiliating. We compromised on a fashionable Pull-up.

The next couple days were kinda mid. School was sooo boring. I couldn't wait for it to be done. The only thing I enjoyed was seeing my boyfriend during AP Gov and my friends during lunch. Staying sober during the day was super lame. I started drinking and getting high during lunch. Whenever I was high, I was totally into Carter. We fooled around like he was the love of my life. When I came down, he was like just my stoner friend.

At the end of each school day, I bought booze from Enrico to keep me company on the drive home. I swerved into my driveway and stumbled into the house where Mommy always had milk and cookies waiting for me. When Mommy wasn't looking, I added some rum to my milk.

I spent the afternoons playing pretend games with my toys and stuffed animals while drinking booze out of my sippy cup. I pretended Grover was my boyfriend but I was secretly cheating on him with Cookie Monster. I really wanted to be with Oscar, but he wasn't into me because I wasn't dumb and shanky enough. Then I made love to Cuddles while I told him everything.

At night, Mommy bathed me, put on my overnight diaper, changed me into my jammies, and read me a story. By this point, I was usually so trashed I passed out in my bed sucking my thumb.

On Friday, I was excited for my date with my boyfriend. I had never gone all the way with anyone but William before. I wondered if tonight would be the night.

Before I could do that, I needed to have a "date" with William. He still thought I was his faithful girlfriend, but to me he was just some rando I hooked up with sometimes. Mommy told me to wait in my room and wear my trashiest outfit when he rang the doorbell. I tried to eavesdrop on their conversation.

William: Hi Mrs Hochbyrd.

Mommy: Good Evening. May I help you?

William: I'm here to see Abigail.

Mommy: Do you want the full package or are we doing a la Carte?

William: Excuse me?

Mommy: Didn't Abigail already explain to you the fee structure for her services?

William: Uh.... I mean...

Mommy: I will be taking over the business end of things from now on. Did you bring cash?

William: Uh... yeah, but..

Mommy: Excellent. All funds are payable in advance. No refunds.

William: So you're saying that I need to pay you before I can see my girlfriend?

Mommy: Hey, it's your time. You can call her whatever you want. Just a reminder that for the very reasonable price of $1000 she will treat you to our very authentic girlfriend experience.

William: I'm not going to pay you $1000 just to spend a day with my girlfriend!

Mommy: Absolutely no pressure. Just let me know what you'd like for today, and I'll go get her.

William: I only brought $150.

Mommy: No worries. $100 gets you an hour of her time. For $50 you can choose between kissing or a handy.

William: Are you actually serious?

Mommy: Time is ticking, pal. This is all coming out of your time.

William: Fine. I'll go with kissing.

Mommy: Alright. Follow me.

With that, Mommy led him upstairs and called out to me, "Your 5:00 is here. He just wants kissing. Sounds like he's got some kind of girlfriend kink. Do everything you can to keep the customer satisfied, but If he tries to do more than he paid for just holler. I'll be right outside."

"Mrs Hochbyrd, you know I'd never..." William protested.

"Just go in and do your thing," she said derisively.

"Thanks, Mommy," I said nervously. When William entered my room, I was lying in my bed next to Cuddles wearing skimpy, black lingerie and fishnet tights Mommy bought for me. Needless to say, I was smoking.

"Abigail, what the hell is going on? Is your mom actually pimping you out?" he asked in disbelief.

"First off, the name's Abby. Second, do you really want me to get a knife in my back compliments of some perv?" I asked, taking a drag.

"Of course not! What I'm trying to say is, why are you a prostitute to begin with? Are you actually having sex with other people for money?" William asked, in a state of total shock.

I thought about what Mommy said. This dude clearly had some serious girlfriend fetish. I had to play along to keep the customer happy, but I wasn't about to give out no freebies.

"Of course not, honey. You know I'd never cheat on you. I'm your loyal and faithful girlfriend," I said, exhaling smoke into his face. He started coughing. It would be so hot for him to catch me in the act fucking another guy. I pushed that to the back of my mind.

"So does that mean I'm your only client?" he asked hopefully. Sadly, he was.

"Unfortunately business has been slow. Maybe you can spread the word," I said flirtatiously.

"And tell everyone that my girlfriend is a prostitute with openings?" he asked incredulously.

"Don't forget to tell them how hot I am," I said with a wink.

"I think that's self-evident," he replied.

"Does it turn you on that your girlfriend's a fucking whore?" I asked.

"Uh.."

"Does the thought of other creepy randos paying your girlfriend for sex make you hard?" I pressed.

"No! Of course not!" he protested. I could tell from the bulge in his pants that he was lying.

"I think your little friend would disagree," I smirked.

"That's completely unintentional," he shot back, defensively.

"Mmm I bet you'd love to walk in on your perfect little straight A girlfriend sucking a dirty stranger's dick," I teased, seductively.

"No! I'd be devastated," he insisted. I noticed him rubbing the massive bulge in his pants.

"It's ok, dude. You can jerk it if you want. I just can't help," I reassured him.

Reluctantly, he pulled down his pants and started stroking his massive cock.

"That's it, buddy. I want you to imagine me fucking a nasty creep and loving every minute of it,"

He started jerking faster.

"Maybe you can find someone for me. I don't care what they look like as long as they have the cash. Maybe you and Mommy can negotiate a finders fee,"

He started moaning.

"You're... such... a.. dirty... slut," he said.

"You ain't seen nothing yet," I responded in my most sultry voice.

I got on top of Cuddles and started making out furiously with him.

"Cuddles is my boyfriend now. I let him fuck me whenever he wants. He don't even need to pay nothing," I volunteered, trashily.

"But he's just a stuffed animal!" William cried out, exasperated.

"I don't give a shit. He fucks me so much better than you ever could," I taunted. I never knew how much of a turn on it was to put him down.

I sat on Cuddles' face and let him eat my pussy while I sucked his dick.

"You're a bigger whore than I could ever have imagined," he said, finally getting the picture.

"This ain't nothing. I want to let multiple strangers cum in my unprotected teenage pussy," I panted.

"Jesus Christ!" he cried, jerking even faster.

"Hopefully, I'll have a girl that I can raise to be just like her mother. Maybe I'll pimp her out just like my Mommy does with me," I responded, obscenely.

"Oh fuck, I'm gonna cum," he screamed.

"Not so fast, dude. I need to give you your money's worth. You can kiss me and jerk off, while my real boyfriend fucks the living shit out of me," I said matter-of-factly.

I got on top of Cuddles and started riding him. William tried to kiss me romantically, but I just slurped my tongue against his like the drunken whore that I was. It wasn't that I didn't have a romantic side. But that was reserved for my real relationships- Trevor, Candace, Cuddles, and of course, Frank.

William couldn't hold it in any longer. He came hard, spurting his load all over me while I fucked Cuddles hard. I smeared it all over my tits. I looked like a bitch in heat. I imagined I was Cuddles' teddy bear girlfriend.

""Fuck yeah, Cuddles. Fuck your girlfriend."

"Give it to me hard."

"Make me your bitch."

"Knock me up, Cuddles. Spray your baby batter in my teenage teddy bear cunt,"

"I love you, Cuddles. My clients don't mean anything to me. I'm all yours!"

"Fuck, Cuddles. I'm cummming!!!"

"FUCK!!!!"

I came all over Cuddles as I humped him like an animal. When we had relaxed, I snuggled in bed next to Cuddles and lit up a cigarette while William just sat at the head of the bed awkwardly.

Eventually, Mommy knocked loudly at the door.

"Times up!" she called out.

William quickly got dressed and looked back at me nervously. I waved bye-bye flirtatiously, while nestling myself all over Cuddles.

"I love you with all my heart, Abigail," he declared.

"Later bro," I said dismissively. I had to get ready for my date with Trevor.

I took a shower, wiping all of William's cum all over me as if it were body wash. I thought about what to wear. Since he was kinda a preppie type, he was probably into cheerleaders. It was my job as a woman to make myself into whatever he wanted me to be.

Mommy helped me find the perfect outfit. It was a super skimpy cheerleader look. Then she styled my hair into pigtails. At first I was afraid he'd think I was a baby, but Mommy assured me he'd love them.

"By the way, here's your cut," she said, handing me a crisp $20 bill. In the back of my mind, that seemed really small, but math made my head hurt and I had a hot date tonight.

Eventually we heard a knock at the door. Mommy answered, while I stepped back feeling shy.

"Hey there hot stuff," Trevor leered. Before I could say thank you, he looked over at me and said, "and you're not so bad yourself." I blushed. Was he flirting with Mommy?

"This one's a charmer," she said, with a Twinkle in her eyes.

"Mommy!! Don't embarrass me," I said, gritting my teeth.

"I'm sorry, honey. You two have a great time. And be on your best behavior, young lady," she admonished.

"Mommy!!" I said. She was sooo embarrassing.

I was super nervous about our date. If Trevor played his cards right, I might let him go all the way. I had never had sex with anyone other than William. I wondered what it would be like!

Trevor took me to dinner at Chili's. He talked about himself the whole time. I learned about his family, how much money he had, how many cars he had, and the cushy job his dad had lined up for him when he graduated. I leaned on every word. It was so refreshing after being with William to be with a guy so focused on his own needs. He didn't ask me a single question about myself. It was like I wasn't even there. I was so turned on.

At the end of the meal, he asked me to pay for my portion. Maybe he was more progressive than I thought! Luckily, I had the $20 I earned from my client.

When we got back to his car, he opened the door to the back seat. At first, I was confused. Then it dawned on me. He wanted me so badly, he couldn't even wait to get home. He was gonna fuck me in the back seat of his car in a public parking lot!!!

I was more sober than usual as I'd only had a few glasses of wine and some rum with my milk and cookies. I nervously waited for him to take the lead. He did not disappoint. He pinned me down and ripped off my skimpy clothes. Without any foreplay at all, he pulled down his pants and whipped out his monster dick.

"See what you've been missing being with that loser," he boasted. It turned me on so much to hear him put down William. It was like the ultimate aphrodisiac.

Without even asking if I was ready, he violently entered me raw. I had never done that with anyone before. It was pretty painful at first. Trevor didn't give a shit about my feelings or desires. He was just using my body to get off. In fact, this was the most he had paid attention to me the whole date. I was starting to learn what a woman needed to do to be noticed.

Soon enough, the fact that he didn't care about my pleasure was actually giving me pleasure. And pretty soon, it became a euphoric pleasure unlike anything I'd experienced before. Here I was, getting fucked raw by my selfish, preppie asshole boyfriend in the middle of a public parking lot where anyone could watch if they wanted to. I hoped they did.

Then I remembered, I needed to record myself to have evidence for Frank. I had already taken plenty of videos of me drunk and high. I wanted to send him the ultimate sex tape. I picked up my phone and hit record.

"Fuck me like a piece of meat," I cried.

"Where'd that prissy little libtard go?" he asked in between pounds.

"I.. killed.. her.." I said.

"So what are you?" he asked.

"I'm... just... a ... slut," I replied breathlessly.

"Whose slut?" he demanded.

"Your... slut... I'm... your... slut!!!" I breathed, struggling to get each word out.

"I'm gonna cum in my slut," he declared.

"But I'm... not..on.. the.. pill," I protested.

"Not. My. Problem" he grunted. I felt him convulse like a crazy person as he unloaded his potent seed in my fertile womb.

The small part of Abigail that was still a part of me was freaking out. This could ruin your life, she said. You can't go to college with a baby!!! Who will take care of it??? How would you afford it???

Blah, blah, blah. She was so freakin' annoying. Always asking her nerdy questions when I was finally getting some action. I just wanted to have a good time getting fucked by my boyfriend. I could always take the morning after pill if I felt like it. And if not, babies are soooo cute. They are kinda adorbs...

"Cum inside me Trevor. Fill me up with your seed. Make me a Mommy," I cried obscenely as I joined him in his orgasm.

When our bodies finally relaxed, I tried to cuddle with him. He pushed me away, and got up to get dressed.

"Not now, babe. I got plans with my bros tonight."

I knew then that I had really hit the jackpot in the boyfriend department. Trevor wasn't some clingy girly-man like that loser William. He was a real man who got what he needed from me and then got on with his life.

He dropped me off at my door, gave me a quick peck on the lips, then sped away.

Of course Mommy wanted to know all the details. Ordinarily I would have been shy, but since she was literally my pimp I felt ok about it. Plus, she discovered all the cum he deposited in me during bathtime anyway.

After Mommy tucked me in and read me my bedtime story, I took out my phone and texted Frank all the videos that proved I completed my assignment. I was so nervous waiting for his response. I tossed and turned. After the longest hour of my life, I finally got my response.

Frank: tomorrow at 7- my place

Gulp. The night I had been dreaming about since I was a little girl was almost here...