Chapter 2

Mrs. Steiner, my former 8th grade math teacher, leaned over my desk. She wore a short skirt that hugged her thick frame, and a light blue, tucked in, button-up shirt with a wide collar. The shirt had just enough buttons undone to show off her massive tits. Her face was framed by a pair of glasses, and her brown hair was in a mess bun on her head, of course with a pencil stuck in it. As a kid she was the source of a lot of masturbatory fantasies since her voluptuous body gave us boys a lot to stare at in class.

Mrs. Steiner leaned over my desk, looking me in the eyes seductively. “So Josh, I am little disappointed in you.” She slid over a sheet of paper that was marked all over with red. “We know you can do better than this.” She then moved behind me and I could almost feel her breath on my ear. “I think you are lacking some motivation. But I think I know what you want. I can help you, my dear boy.”

From behind, my teacher slipped her hands over my shoulders and caressed my body. “Mmm, such a strong boy. You’ve been hiding something under all these baggy clothes.” She unbuttoned my shirt one button at a time and slid her hands over my chest. I turned my head to kiss her and could taste the cigarettes she used to smoke on her lunch break on her tongue. It was acrid and enticing at the same time.

She then moved us to her desk where she sat, open legged on the lip of the table. Between her thick thighs I could see clearly that she wasn’t wearing any panties. “I think you’ve been too distracted by me and just need to clear your head so you can focus. Can I clear your head for you?”

Mrs. Steiner then pulled me by my open shirt closer so that I was between her legs. She ripped my shirt off and with hasty hands unbuckled my belt. My pants hit the floor. I watched her then strip her shirt and skirt to stand before me. Her massive tits sagged a bit and her shapely figure was incredibly enticing. She looked like a fertility doll. She then bent over the desk, exposing her fat ass to me.

My belt in my hand, I knew exactly what to do. I gave her some smacks across that wide ass, and she hissed with pleasure. After I had left some red welts, I dropped the belt and hungrily dove into that waiting ass. The heat coming from her was intense and I buried my tongue into her pussy.

“Oh Josh, yes!,” Mrs. Steiner screamed as I tongued and explored, pushing deeper into her.

“Yes, yes! Lick mommy’s pussy,” came a different voice. My mom’s voice. I kept licking but was trying to back away from the massive ass to see her. But I was stuck. “Don’t stop baby. Keep going!,” the voice cried. But I was shocked. I wanted to keep going but I felt like I was being enveloped. I felt hands push my face deeper into her, until...

I woke up in a sweat from the dream, but within seconds, could hardly remember the details. Was I fucking my teacher? I got up from the bed and felt slightly hung over. I suddenly thought of the previous day and how that too had felt like a weird dream. But that day I remembered clearly and knew was real. My mom had bared herself fully for me and forced me to do the same. I had always known that my experience growing up was different than other kids. That my mom was different than other moms. At first, I assumed it was because my dad was out of the picture, but I have slowly come to realize it is because this is just who mom is. She just isn’t hung up on sexual taboos. How she ended up having a kid with body issues is beyond me.

I ruminated over this as I got up and started to get ready for the day. It was the weekend and I had no real plans but to run some chores. As I got ready I looked over my self and my outfit in the mirror and ... and I actually felt different. For the first time I actually kind of thought I might look OK. It was very tentative and I sensed how fragile it was, but there was something there. I wasn’t immediately repulsed by the young man in the mirror. Maybe mom’s way was not so crazy after all.

I made myself breakfast quietly, knowing that a late shift for mom meant she would be sleeping in. I left the house and met some of my friends at the mall. We tooled around and bought a few things until finally heading to the food court. It felt like it was going to be a good, chill day.

But then I saw her. There in the food court, at the table next door, was Tina. I had had a major crush on her last year, but of course never acted on it. She had graduated and gone on to college, so I hadn’t seen her for several months. But she was still as cute as ever. Standing at 5 foot nothing, she had lightly tanned skin, straight black hair, and almond shaped green eyes- a gift from her half Irish, half Japanese heritage. Her body was slim and toned, and it looked like she had kept up her gymnast training. My friends noticed me staring and knew how badly I had lusted after her, so were nudging me and teasing a bit. My friends knew I was shy but didn’t truly understand how deep my self-esteem issues went.

I did my best not to stare for too long and fantasize about what I would do to her petite body when she suddenly looked up and saw me. A flash of recognition crossed her face, and she smiled.

“Josh?” she said suddenly. She started walking towards me, and I met her halfway, not wanting my friends to witness whatever was about to go down. Although still shy, I had a quick realization that I was walking toward her and not away. This was new.

“Hi Tina, good to see you,” I said, a little proud I didn’t stutter or say something moronic right off the bat.

She smiled. “You too! It’s been a while. I wasn’t even sure you’d remember me.”

We had shared a couple classes and had brief interactions, but never spoke for more than a few minutes, and never outside of class. Remember her? Of course I did. I would never admit it, but I had looked her up online now and then to see if she would post any wild college pictures.

“Of course I remember you,” I said, internally kicking myself for not playing it cooler. Oh god. I should leave. Find some excuse to get out of there. Abort! But instead of bolting I just asked, “How’s life after graduation?”

She smiled. “Great! I’m over at the state school and it’s been tough school-wise, but the parties are great!”

We laughed and chatted for a bit longer. Mostly small talk and it felt really ... easy. Internally there was a voice screaming at me, but externally I was pulling it off.

“Anyway, I have to go apply for some summer jobs. I am definitely going to need the cash, but it seems like nowhere is hiring. But anyway, my sorority is having a huge party in a few months at the house. Maybe you can come? Do you have insta? I’ll DM you. Bye!”

She said this all in one quick rush and I just stood there stunned and nodding my head. “Umm, yea. That’d be great. Bye!” I said, completely taken aback. I watched her walk away, only half my brain remembering to check out her tight ass.

Once she had gone, my friends, who had been watching the whole thing, came to join me. Rounds of back slapping and teasing went around. The general theme was ‘finally, Josh comes out of his shell.’ We spent a few more hours out and just hanging around, and it was late by the time I got home.

Hearing the door open, my mom left her room, closing the door behind her, to meet me in the living room. She was dressed clearly to go out, with a sexy, short skirt and a tight top that had a V cut through it, showing off plenty of the sides of her ample breasts. “Hi sweetie!”

“Hi mom,” I said cheerfully.

She smiled. “Well, someone’s a bit cheerful. Good day?”

“Yea, actually. It was. Just hung out with my friends, and saw someone I hadn’t seen since she went to college. It was nice.”

My mom raised her eyebrow. “Since SHE went to college, ey? Good for you.”

I laughed, but felt like I had to let her know how she helped. “Yea. To be honest, I wasn’t shy around her at all like I used to be. I think last night really helped me. So ... thank you mom,” I said, sincerely.

My mom blushed and seemed to get a little misty eyed. “Oh Josh, I am so happy to hear that.” She closed the gap between us to give me a hug. She was warm and her body felt good pressed against mine. She pulled back only slightly, still holding on. “If it helps, you are welcome to walk around naked anytime!”

I laughed. “I don’t know about that mom, but thank you anyway.”

She smiled. “Are you ready for phase 2?”

I looked at her dumbfounded. I tried to break our hug, but she held, making it clear she wasn’t ready for it to end. “Phase 2? Mom, I just told you. You helped. I don’t think we need a phase 2.”

Her face got serious. “Yes, Josh. You do. I need to know you are OK out there, and this is the only way I know how. You are coming out with me tonight. I called out of work and called in some favors. You’re only 18, so some places with alcohol are still off limits, but I have some pull.”

Was she taking me to a club to meet women? “Mom, seriously, I am ok,” I laughed it off. But her face didn’t change.

“You are doing this. No ifs, ands or buts about it. Now go shower and put on the outfit I left on your bed.”

She was stern and there was no reason to argue. Once she made up her mind, as I saw last night, she wouldn’t hear no.

I took my shower, and as I stepped out I took a hesitant look in the mirror. As I mentioned, I usually avoid this as much as possible. Now though, I tried to see what my mother saw yesterday. I let my towel drop and looked over my body. I was not a hulking mass of muscle for sure, as both my mother and father (of what I could see from pictures) were on the lean side. My arms did show off some definition and I did have the abs my mom had mentioned. Memories of her hands running over my body flooded through, causing my dick to stir. And there was that too- my dick. She clearly remarked on how big and nice my cock was. The memory now of her putting her forearm against it to measure made my dick pulse a bit as it grew. I gave it a stroke and could appreciate its girth. It didn’t look dissimilar to all the cock in porn that those women seemed to REALLY love.

“Hurry up, Josh,” my mom called from the other room. Coming out of my daze, I shoved my meat as best I could into some briefs and put on the outfit my mom had mentioned. I never really went out to anywhere nice, but she had put out a simple, well tailored, white button-up shirt and some stylish back jeans. Looking in the mirror now, the cut of the clothes accentuated my broad shoulders and I had a brief thought ... I look, kinda good?

I entered the livinroom and my mom gave me an approving look. “You look great, honey. And I can see the confidence growing in you already. Sometimes you need an outfit to help you see what sweats and T-shirts hide. You never see me wearing those, do you?”

I chuckled. “Mom, I don’t think I’ll be able to dress like YOU do at school. How would the teachers react to me being basically naked all the time.”

She laughed, but then remarked. “I know some of your teachers, hun. They would be fiiinne, if you did that. Off school grounds anyway. I ran in to Mrs. Steiner last month by the way. I forgot to tell you she says hi.”

She rushed me out the door and into the car before I could really process that. We chatted a bit and before we knew it we were in a different part of town that I had never been. We pulled into the parking lot of an off the path, dark building with the sign on top, “Silks Gentlemen’s Club.”

What the fuck. I thought she was taking me dancing, not to a strip club. She worked at a different club called Secrets, so I knew this wasn’t even that.

“Mom ... why are we at a strip club.”

She smiled over at me. “Phase 2 honey. I mean, I couldn’t take you to where I worked! But I have a friend here that was willing to help out.”

“Ok, but my question wasn’t why aren’t we at YOUR club. I thought you were taking me dancing. Not to,” I pointed, “One of these places.”

My mom’s face turned serious again. “These places? Watch your tone young man. These places are what have paid your bills since your dad left.” She softened, knowing deep down that I wasn’t insulting her. “No sweetie. Not a club. I wanted to be able to 100% guarantee you had a good experience. And my friend Candy is a 100% guarantee, I promise.”

She exited the car, leaving me without the chance to question her further. I followed her dumbly to the door where we were met by a large, intimidating bouncer. He maintained a harsh scowl as he prepared to take my ID. Would they even let me in?

Seeing my mom his entire face changed. He smiled broadly and exclaimed, “Skyler! Good to see you!” He referred to my mom by her stage name. He opened his arms and enveloped my mom into a huge hug. Her body was tiny compared to him, and she seemed to disappear underneath his grip. He released her and looked over at me. “Who’s this lucky young guy with you?”

My mom turned to me to give me a look and said, “I spoke with Candy before and let her know I was coming. This is my ... friend,” she shot me another look as if to say to play along. “He’s from out-of-town so I am showing him around and making sure he has a nice stay.”

The bouncer chuckled. “Oh, Candy will make sure he has a great time.” He gave me a wink and moved from the door, gesturing us in. “Have fun, playboy. Welcome to town.”