Chapter 3

In which our boy Justin has a hookup with a milf in her 40’s

I wanted Joan, my heart and my cock were screaming for her; but she was gone, and insisted I find another lover.

Mom was sympathetic. “She’s such a nice woman, I’m sorry she had to go. Don’t worry dear, you’ll find another, then you’ll feel better. Don’t go for one of those silly school girls, ok? I know they look nice but an older woman will take care of you better.”

It wasn’t easy.

I wasn’t interested in girls my age. I wanted an adult women, a self sufficient woman with her own place, a job, a life. A woman who would be responsible for herself, and could teach me things. A woman who knew what sex was.

15 year old girls look great, but they were children. So was I of course, I knew that.

I did all the things Joan had taught me, the extra moment of eye contact, break off, repeat. I was tall for my age, but my face could never pass as adult. Women looked amused at my efforts, or horrified.

I cruised supermarkets, malls, fast food places, anywhere I could get to.

As I got more frustrated, I came on to anyone who wasn’t fat. I even made a pass at a grey haired Chinese woman.

“How old are you, to be looking at me that way?” she demanded.

I think she was the first to actually talk to me.

“Fifteen.” I said.

She looked surprised.

“How old did you think I was?” I asked.

“Fifteen, but I thought you’d lie about it.” She laughed. “I’m Lucy, and you don’t have a chance with me.”

“Why not?” I pleaded.

“I’m not into kids.” She said, “My daughter is twice your age and I’m married.”

“I don’t care about that, I think you’re hot.” I wheedled.

Lucy laughed hard; “I like you, you have spunk. Oh, bad choice of words. Listen, I’ll tell you where the cougars hang out. Go over to the food court at Greenfield mall. Maybe you’ll find someone, but fifteen is tricky.”

“Do you think I should lie about my age?” I asked her.

She thought about that for a moment.

“No.” she said. “Never start a relationship with a lie. I learned that the hard way.”

“I like you.” I said optimistically.

“I like you too, maybe when you’re a little older.” She replied with an indulgent smile.

“I thought you said you’re married.”

“So much to learn!” she laughed.

It was a big, noisy area. I walked through, around, back again. I observed some collage age guys sitting with middle aged women, could be shopping with mom.

I also saw some high school age girls with guys who looked really old; dads? One looked like a granddad.

I bought a burger and sat. A woman came to my table.

“Can I join you?” she asked.

Nothing came of this, but I was thrilled; we flirted and talked, then she left abruptly before I could ask for her number.

I was there several more times, and managed to talk to a couple of women. They were there looking for sex, but there were 5 times more guys. Collage guys, bigger and more clever than me.

A girl came and sat with me; I’d seen her before, chatting with the old guys.

“No luck?” she asked kindly.

“No. Not for you either?”

“Not yet. I’m waiting for Mr. Right.” She said seriously, then laughed. “I’m Charlie.”

She was well dressed; heels and stockings, skirt above the knee, color coordinated, manicured, good hair. She had a pretty face too, with a rather odd square chin and big brown eyes.

“I’m Justin. You’ll find him, you’re really hot.” I told her.

She blushed a little. “Why, thank you Justin!” she gushed. “And so will you. Hey, see that woman? She’s into you.”

“Really?”

“Go up to her and ask her if she can drive you home.”

“I can’t do that.”

“Go on, quick! Before someone beats you to it.” She hissed. “She’s here all the time, she’s a cruiser. Do it!”

She wasn’t quite thin, but she had a waist. Large breasts, frizzled hair over her shoulders, and a somewhat sad face.

My heart was in my throat as I approached. I saw she was older than I realized, and I almost chickened out, but I did what Charlie told me. Anyway, she wasn’t as old as Lucy. But Lucy was special.

“You’re a little young for that aren’t you?” the lady replied in a high pitched nasal tone.

“Not at all.” I insisted. “I’m Justin.”

She looked at me doubtfully. I smiled hopefully.

“Ok, let’s go.” She said.

This was all a bit sudden; I thought we would talk and hang out for a while first.

I followed her out of the mall into the parking lot. She unlocked a decent looking car and we got in.

“Show me.” She said.

“Huh?”

“Don’t make me repeat myself.” She said irritably, twisting around to look at me.

I was terrified, thrilled, and turned on. It was all a bit nasty and crude. This wasn’t like my affair with Joan at all. Still, here we were; so I pulled my pants open, and down to my thighs. I lifted my young cock and I was erect.

She looked at it as I squeezed it, making the head bulge.

“You’re a bit small.” She commented.

“Yes, but I know how to use it.” I said quickly.

“Really? Ok, well we’ve come this far. Pack it up.” She said, and started the motor.

“What’s your name?” I asked.

“Does it matter?” she quipped.

“Yes.” I insisted, quite thrilled with my own persistence.

“Nora.” She said as we accelerated.

We went to a motel, where she already had a room. That was simultaneously sordid and sexy.

“How old are you?” I asked, immediately regretting the question. Joan had told me never to ask that.

“I won’t tell and I won’t ask.” Nora replied, but she smiled a little.

We went into the room, it was sparse.

“Get undressed.” She instructed.

I started to do it slow, like Joan liked; but I Nora looked impatient so I just took it all off.

“You’ve done this before?” she asked, frowning at me.

“Yes.” I insisted.

“With women?”

“Yes.”

“With men?”

“No!” I exclaimed, shocked by the question.

“Ok, lie on the bed face up.” She told me. Nora had barely even put her car keys down yet.

She sat next to me and reached for it; her hand was cool and excruciatingly wonderful as her old fingers wrapped around my young cock.

“Well it’s not too big but it sure is hard.” She said, squeezing it firmly. “What do you like?”

“Kissing.” I said.

“Well you are full of surprises.” She said, her face breaking into another brief smile. “Kissing! Really.”

“Really.” I insisted. “I mean, I like the other stuff too.”

“Other stuff!” she laughed, “Ok, I like you. And I like the other stuff.”

She bent over me; I lay completely passive as she kissed my mouth, her hand still on my excited penis.

Our tongues met, and I resisted the urge to fondle her dangling breasts. It was a ‘thing’, to lie prone as she did what she liked.