Tomato in the Mirror
Chapter 1

Caution: This Sex Story contains strong sexual content, including Ma/Fa, mt/Fa, Consensual, Oral Sex, Exhibitionism, Voyeurism, Prostitution,

Desc: Sex Story: Chapter 1 - "Your momma's a whore." Sure a lot of people make that comment, but what if it's true? And how do you handle it? Perhaps it might be time to join the business.

"Your momma's a whore." Now let's be perfectly honest. She is, was and given her tendency to view the world as a place best viewed from on her back with a fist full of dollars in her hand it seemed like she always would be.

But in this case the truth was really not the sort of thing I wanted to discuss with Rocky Tomasi the schools football hero and primary bully. He loved to go around and pick fights with people he thought he could beat up with no real problem.

Today he was getting around to me. Now to look at I'm pretty sure most people would have thought he had the right idea. I was tall for my age (16) but I had a whipcord thin body and features best described as delicate. One of moms pimps had one told me that if I let my hair grow out some and dressed the right way I could probably pull some serious action.

Not hat I was interested in that sort of action. I had nothing against gay people, or straight people or whatever, I just happened to be more fond of women. Despite seeing one of them naked an in action pretty much every night of my waking life.

Oh yeah Rocko, almost forgot about him. I was still resolutely acting like I couldn't hear him as I picked out the books I wanted to take home. "Didn't ya hear me faggot I said..."

I knew how this went, I had a very good idea of where it could go. So instead of speaking I turned and snapped a kick square into his shin. He yelled and came up off the leg. As he did I brought the leg back up and kicked him square in the solar plexus. Air rushed out of him, and he hit the ground gasping.

Part of me wondered if this would complete the trifecta. I had been kicked out of two high schools so far. The city only had this one left, maybe I could just take my GED and get out of this ongoing social nightmare.

As people ran to look after the battered sports hero I walked off quietly and without making a fuss. Then made it out into the parking lot. I had the privilege of being one of the few kids at school who drove a BMW. Sure it was ten years old, needed new paint and I was getting a bit suspicious of the way the transmission was acting, but it was a BMW three series. Mom had gotten it through a client of hers.

Her car was an older Porsche 911. Flashy but accessible. Much like her.

The drive home was smooth and without hassle. It dawned on me that today was wednesday and Mom would want help with her four O'clock. I pulled into the garage of our house at 3:40 and walked into the house, through the kitchen and up the stairs to my room where I set down my books.

I cracked open my english lit book and took in todays homework when mom knocked on the door. "Come in." She walked in wearing a see through baby doll, she had no bra on but I could see pink french cut panties under it.

"Hi Jimmy, Tom is coming over at four and you know what he likes." She said with a smile.

"Yeah should I look in around 4:10?" I asked.

"Yeah he's usually up to full speed by then. Thanks dear."

"No problem mom."

She shut the door and I went back to school work. I had pretty much written my two page paper that would be due tomorrow by the time I heard mom and Tom grunting and moaning through my wall. Looking up I saw the clock read 4:09. Grinning I got up and walked over to moms room.

As usual she had left the door open a little and I walked over and peered in, making sure my eyes could be seen from the bedroom mirror. Tom was happily pumping away into mom with long strokes from behind. Mom had a slim figure but a full ass, one that attracted mens eyes. Today he was burying himself over and over in her pussy. He looked up and saw my eyes looking down at him and doubled down on his thrusting into her.

He leaned down to whisper in her ear, and I heard her giggle as she moved harder back at him. This was Tom's trip, he loved the idea of being watched, feeling something dirty about perhaps warping a young mind. Some dirty young man who was watching a man fuck his mom silly.

Really I didn't have the heart to till I had seen this since I was seven. Everyone has some sort of dark fantasy in the back of their mind, why ruin it for them?

That was moms specialty, being the person someone could bring that fantasy too, and she would do her darnedest to make it happen. When she was younger she played the student to people who had teacher fantasy's, The daughter to men who had little girl fantasy's. Now she played Mommy, and naughty teacher for people. What you wanted she made happen. It was something that earned her a comfortable living.

Tom's cock was rocking her harder and I could see the sweat building on their heads. Her skin was goose bumping and her nipples were standing out. Today she was really into it. I mean she was into it most time. Mom had a mental condition doctors described as over sexualization. She ran hyper sensitive to sexual thoughts so she was pretty much horny all the time. At one time they tried meds to get her to cool down, but she said they made her feel like a robot.

So she decided to make lemons into lemonade and turned her condition into a vocation. She had started in junior year of high school, and had been at it ever since. Somewhere there was an "oops" with a condom and I was conceived. So she started playing the roll of the "fallen girl" for some of her clients, made one or two think they were responsible, and kept right at work.

Tom was making noises like a bull behind Mom, which meant he'd be be doing his thing soon. I hung out for the ending as he shouted at the ceiling then disappeared to finish playing the role of "traumatized son.". Which in this case meant going back to working on Geometry.

I heard Tom and mom talking in the other room then eventually heard him leave. A couple of minutes later there was a knock on the door. "Come in."

Mom opened the door wearing the baby doll but absent the panties. She smiled lazily as she looked in. "Thanks Jimmy, Tom has a thing for that you know."

"Your welcome mom, it's not like helping out like that is a big deal." She grinned.

"Gotten tired of watching mom earn her living the old fashioned way?"

"Don't get me wrong I've just seen you do that a million times."

"Yeah any film does get old after a while." She grinned. "So when are you going to find some girl to do those sorts of horrible things to?"

I shrugged. "Beats me mom. All the girls lately seem to want douchebags."

"Yeah all the ones you look at, look around and you might see some different girls, trust me." She paused and looked thoughtful. "Meanwhile."

"Meanwhile what?" I asked.

"I have a client."

I groaned. "Another one today?"

"Let me finish, she has something she wants to do. It involves a cute young man. So naturally I thought of you."

I raised an eyebrow. Mom had kept me informed as to what she did, and I kept her secrets and occasionally did odd things to help, but this was the first time she suggested I get involved in "the family business." So to speak.

"Like what?"

"She has thing for the idea of the lawn boy, but she doesn't trust any of the guys who actually do lawns to keep their mouths shut."

"So I would..."

"Go over there, do her lawn, then clean her pipes so to speak." Mom said with a grin.

I had to admit the idea had an appeal. I had sex before. A friend of hers loved the idea of taking my cherry and teaching me a few things. And I was an eager learner, but it wasn't like I was getting pussy on a regular basis.

"Okay, and what do I get from it?"

"A couple of hundred dollars."

I acted like I was thinking about it. "Okay I'm in, when do I do this?"

"Is tomorrow too soon?"

I grinned. "Nope that would be perfect."

For the rest of this story, you need to Log In or Register