Chapter 2

I had Jessie’s daughter Shannon do her homework at the kitchen table, then watch a movie on my couch while her mother worked. She was only 14, but I thought she would be a real hottie before long. Her straight red hair nearly descended to the tops of her budding breast bumps, until she tied it up in pigtails, which were cute on her.

I went to my office and turned on my laptop to check how Jessie was doing as a camgirl. She was laying on a sleeping bag smoking a cigarette in only her bra and panties. In three hours, she’d only gotten $11 in tips. I looked at the log and saw that six times she had shown the viewers her boobs or pussy for only a dollar. She had masturbated nude for only five bucks.

I decided to have a little fun and test her limits. I signed in as ‘LuvYewLonger’ and typed, “Put a finger in your pussy $2.” She happily moved her panties aside and did. I typed, “Taste your pussy finger $2.” She looked disgusted a moment but did it with an obviously fake smile. I typed, “Three fingers and lick them, $5.” She sighed, but reluctantly followed my request.

‘HotBoy4Momma’ typed, “Put a dildo in your pussy 2$.”

She said, “Sorry, I don’t have any toys.”

‘HotBoy4’ and two others left the channel, and Jessie looked quite nervous. ‘INeedAGirilla’ and I were the only viewers still watching.

I typed, “Yer really hot. You must have a boyfriend?”

She said, “Yeah.”

I typed, “What is he like? $2.”

“Well, he’s older, but he has a nice big dick. I don’t know him that well, but he does good things for me.”

I responded, “Cool. Suck him off! $40”

“I ah ... he’s not here right now, but maybe some other time. Do you want to see my butt?”

‘INeedAGirilla’ typed, “Sure! Put a finger in your ass $3.”

I closed the laptop screen as her daughter Shannon walked in. She asked, “I’m kind of hungry. Do you have snacks or something?”

“Sure. There are veggies and apples in the fridge, or microwave popcorn in the kitchen cupboard on the right.” She walked out and I wasn’t surprised to hear popping soon after.

I opened the laptop and switched to Admin so Jessie wouldn’t see I was watching. As the image came up, she had two fingers in her asshole! She turned around to face the camera as ‘INeedAGirilla’ typed, “AWESOME! Now lick ‘em clean $10.”

“No, just ... no. That’s too gross!” I could see some feces on her fingers and she looked quite disgusted.

‘INeedAGirilla’ left and Jessie thought she was alone in the channel. I saw her start to cry. I noticed her shift was nearly over and she’d been tipped a measly $34, of which she would only get half.

I closed the laptop and walked Shannon to their apartment, which was only a block from my house. I asked Jessie, “So how did it go tonight?”

I heard her holding back tears as she said, “Not bad.”

“I’m glad. Have a good night.”

Before I could leave, she said, “Wait!” She quickly walked over and whispered, “Um, Kurt, I could get more tips if I had ... a few things from an adult store.”

“We’ll talk about it tomorrow, when Shannon is in school. Have a good night.” I squeezed a butt cheek and kissed her lips. She wasn’t enthusiastic but didn’t resist.

As I turned and left, she said, “Thanks. Good night”

At noon the next day we went to a place named “Dill’s Dos and Don’ts”. I picked up some condoms. Jessie got an assortment of vibrators and dildos, lube, an almost see-through pink tube top, and a pair of fishnet stockings. The total was over two hundred dollars. As we walked to my truck I quietly said, “I’ll treat this as an advance on your pay. I’m glad I could help you out.”

“Thanks so much, Kurt. But ... but that’s a lot of money and I don’t make very much. Maybe I could blow you or something...”

“Shhhh! I’m not going to let you get in trouble again. No hooking, no money for sex.”

“Well...”

“I guess if my girlfriend made me really happy, I could give her a gift. I haven’t had anal in a long time. Have you done anal sex before?”

“Um, yeah.”

“Great!”

“I uh...” She looked quite unhappy with the idea.

“Or if being my girlfriend makes you uncomfortable, we can go back to just boss and employee. I can be professional and not talk about personal things with you. I wouldn’t give you gifts or furniture, though.”

She looked afraid and quite reluctant as she accepted my offer. “I guess we can do it. Just use a lot of lube and start slow, okay? Please?”

“Sure. I’m a nice guy. I wouldn’t want to hurt you.”

“And, um ... Kurt...”

“Yes?”

“One of the internet guys wanted to see me suck off my boyfriend. He was gonna give me a big tip. Less than I usually got for blowjobs, but it would be legal money. If you come over when a guy wants me to...”

“Sure. It won’t count toward the sex twice a week you do as my girlfriend, though. Right? Since I’ll be helping you earn more money.”

“Uh, right.”

Back at my place, I had her lift her skirt and lean over the edge of the bed. I shouldn’t have been surprised she wasn’t wearing panties. “I’ll make sure and get us nice and slippery. I don’t want it to hurt.” I drizzled some lube between her butt cheeks and rubbed my cock in it before I slid halfway in.