Chapter 4

In which young Justin pushes the envelope of age gap sex with 67 year old Jules.

I met Charlie at the mall again and we talked for a long time. She asked me how it went with Nora, and wanted details. She laughed happily as I told her.

“So you’re not into the bisex thing at all?” she asked.

“No, men aren’t attractive to me.” I told her.

“Too bad.” She said, “There’s a lot of opportunity for a good looking boy like you if you’re into a little cock play.”

“So you’ve done that sort of thing?” I asked.

“Oh yeah!” she said excitedly, “I did, I do. Both ways always I say! I had it with Nora and Fred. That was before.”

“Before what?”

“Before I transitioned. I was a cute boy, like you. Oh, you didn’t know? Haha.”

I guess I stared a little. “You’re bullshitting me.”

She grinned happily at my disbelief; I realized it was a compliment.

“I’m a trans-girl!” she said enthusiastically, “Do I look different now that you know?”

“You’re still hot.” I admitted, “So ... uh...”

“Yes, I still have it, and it works too.” She told me, still grinning excitedly. “I might get gender re-assignment someday, I haven’t decided. Are you shocked?”

“Wow.” I mumbled, “Yeah. I really am.”

She had tits; her low cut blouse meant they were visible. She looked feminine, her voice was soft too.

“I started hormones early.” She told me, “I got them illegal, my parents flipped when they found out but I got them to support me. So, are you really into women as old as Nora? Older? How far does that go?”

“I don’t know.” I admitted, “I’m just attracted to good looking women, age isn’t important to me.”

She thought about that, then said; “I guess if it’s just an affair, it really doesn’t matter.”

“What about you?” I asked.

“I’m flexible with women but I like youngish guys; that is, under 30.”

It was a couple of months before I got laid again. The ‘cougars’ were friendly to me, but they all said the same thing; “Just too young for me.”

I came in one afternoon and looked for Charlie; she was at a table with a guy. He looked maybe 30ish. She caught my eye for a moment, and raised an eyebrow in some sort of message, then said something to the guy.

He looked shocked, then got up and walked away.

“That’s what happens when they find out I don’t have a cunt yet.” She said with a hint of bitterness.

“They’re looking for a girl.” I said gently.

“I am a girl!” she spat angrily. “I can do all the things other girls do, I can look cute and talk cute and dress nice, suck and fuck, but both ways. BOTH WAYS Justin. Haha. Well, he doesn’t know what he’s missing.”

Years later, I had an affair with Charlie. Both ways, as she said. It was good, quite the experience. But I don’t think my readers want to know about that.

Then came Jules.

I saw her talking with some of the other women, including Nora. One pointed to me and Jules headed straight for me with a predatory smile.

She was short. A little bit square. She was much older than any of them, with short snow white hair that framed her face. She wore really high heels, and tight light trousers that stopped at the ankles. A colorful blouse with open shoulders that she managed to get away with, she didn’t have a lot of cleavage.

As she got to my table, her eyes hit me.

Blue eyes, excited eyes. She was excited by the hunt, at the prospect of 15 year old prey. Her red painted lips had a very sexy curl to them, a crazy confidence, joy, zest. Her cheeks were slightly baggy.

Jules was 67 years old. And she was sexy.

She sat in the cheap plastic chair, diamonds in her ears and gold around her neck making her look out of place. A gold Rolex watch adorned one wrist, and her nails were just a little long, painted red. So were her toenails, visible in her open shoes.

She didn’t say anything for a while; she just looked at me, into my eyes.

And I looked back.

I wished Charlie was there to advise me; “How old would you go?” she’d asked me. I remembered my answer; “If she turns me on, I’ll have a try.”

“I’m Jules.” Jules said with a terse smile, breaking the silence.

“I’m Justin.” I answered.

I was trying to figure out why I found her attractive; her figure was passable, but not amazing. She didn’t have big tits, or long legs, or a tight ass. Her hair was so short that it was nearly masculine, and as I said, white.

But those eyes of hers; the way she looked at me, right through me. She was sexy because she was excited, apparently by me. Her smile turned her old face into a beacon of allure, her sensual mouth and bright eyes compensated for everything.

“I hear you like to kiss.” Jules said.

“Yes.” I said, “I like the other stuff too.” I said, trying to sound calm.

Joan had told me, “Stay cool. Be attentive but never eager. Eager scares women away.”

“I’d like to kiss you right here, right now.” Jules challenged me, with a grin of eager delight.

“Ok.” I said, almost shaking with that sweet mix of fear and excitement I’d been waiting so long to feel again.

“Just to be clear; I’m not promising anything. I just like kissing, and I like making a spectacle of myself.” She said.

Her voice has a soft sexy southern accent.

“Of course.” I said. “I have to tell you, I don’t normally kiss until the second date.”

She laughed happily; “They told me you’re a charmer. Come on, lean forward. They’re all watching, let’s give them a show!”

Her mouth and mine met over the small plastic table. I reached up my hand and put in on her neck, and I kissed the old lady for the first time.

Her mouth tasted fine; her teeth were healthy, natural white. Her tongue entered my mouth brazenly, and I sucked it through our meshed mouths.

The loud lunch area seemed to go quiet. A boy and a granny were kissing in public.

With her hands on my face, and without breaking our kiss, she slid out of her chair and sat on my lap, legs on either side, face to face. She went at my mouth like it was a competitive event. I put my arms around her waist and pulled her tight against myself, thrilled with her audacity and my own. She put her hands on my face, her fingers curling around my ears.

“You’re hard!” she laughed, her eyes gleaming with the thrill of our public show. “Are you an exhibitionist, Justin?”

“No, I just like you.” I said. But I was thrilled by the idea that everyone was watching us. That the cougars who had rejected me saw that I was real, I was a player.

Jules kissed me again, and we kept at it for a while. My hands crept up and down her back, the thrill of it was fantastic; I could kiss her all night.

It was a wonderful beginning of a wonderful relationship; cut right past the crap and just kiss, hold each other and feel the heat, let my hands do the talking, and my mouth do the feeling.

In public, it was outrageous yet safe. We were already at the limit, our kiss was as far as we could go. Either of us could stop, or we could continue, but we couldn’t go further.

The weight of her small body on my thighs was comfortable, her warm sexy old curves in my hands, her short silky hair.

She was an old woman though; I was looking for an older woman, but Jules was granny age, retired for sure, a senior citizen. Way too old for me, but I sure was enjoying this public fooling around. It was fun, exciting, and sexy. I didn’t think she wanted me either, not for more than this bit of exhibitionism.

She smelled nice, and tasted nice. She was soft and sensual. She broke away to look at me for a moment, and we smiled at each other; if it stopped right then and we never touched again, we were friends. We had a connection. I wondered if those fat sparkly jewels in her ears were real diamonds?

She gripped my head in her hands and kissed me some more, the mall and the other people fading away.

A security guy came over; “You two stop that, get off him!” he said angrily.

“What’s the problem honey?” Jules said to him, her hands still in my hair and mine on the small of her back, “Is there a law against kissing?”

The mall really was silent. Still holding Jules against myself, I looked around. EVERYONE was watching. Standing, sitting, frozen at our spectacle.

It excited me; I’d never been noticed before. I was a nobody; until Jules sat on my thighs and stuck her outrageous old tongue into my mouth.

Several more rent-a-cops came over. Jules held her ground, or rather, held me.

“Listen, we tolerate what goes on here but you people have to keep it decent.” An older one said. “Please, take it outside.”

“I can’t argue with that.” Jules sighed, and got to her feet. “Justin, would you like to have dinner with me?”

“I’d love to.” I said, “But just to be clear, I’m not promising anything.”

“Let’s go.” She laughed.

We walked through the mall holding hands. A teenage boy and an old woman holding hands, like lovers. It was great.

I was far from where I lived, no one I knew would see me here; I wouldn’t want it known at my school, but if it was, I’d own it. I wasn’t ashamed.

My cock was poking against my pants, I didn’t know if it was visible and I didn’t care. We went outside and got into a huge very old gleaming Cadillac convertible.

The car started with a quiet whoosh of power. Jules grinned at me.

“Like it?” she asked as the top lifted and disappeared into the back with a whirr of motors.

“Very cool.” I said.

The little old lady backed the big car out of the parking space and accelerated through the parking lot.

“Bench seats the size of sofas!” she said to me, “They don’t make them like this anymore.”

Like her, the big car demanded attention. Heads turned as we passed, and Jules loved it. It was more like a big boat than a car, the way it floated through the streets, gliding smoothly and nearly silently.

Like Jules, a relic from a bygone age.

She stopped for a minute to put the top back up.

“It’s great for showing off, but at highway speeds it’s not nice.” She explained as the old machine worked flawlessly.

The big tires chirped as she accelerated up the ramp to 90, laughing out loud. “God I love this car!” she said, “If only it didn’t spend half the time in the shop and use more fuel than an ocean liner!”

“Tell me about yourself.” She said as we drove, “Why is a cute boy like you interested in old women?”

“I don’t know. An older woman was my first girlfriend and I liked it.”

“How old?”

“Thirty two.”

She laughed; “Well, you’ve come a long way baby!”

I told her everything, as I do. How I was smitten, heartbroken when Joan left.

“What about Nora?” Jules asked.

“That was just sex.” I said.

“From what I heard, it wasn’t Just at all.” She said, and laughed again. “What about your parents, do they know about your sex life?”

“Mom knows everything. I’ve never met my dad.”

“What does your mother do?”

I usually lie about this, but I told Jules the truth. “She’s a whore.” I said. “She likes to say ‘escort’, or ‘professional companion’”.

Jules looked at me wide eyed; I’d got her with that one.

“Really?”

“Yes.”

“How old is she?”

“Fifty.”

“Wow, I’d love to meet her.” Jules said as we pulled off the highway and up a country road.

She stopped the car at a layby with a sunset view. She turned and leaned on the door, one foot up on the seat, and we talked some more.

She’d been married six times, widowed three divorced three. She’d been a hippy girl in the 60’s and had ‘A LOT of fun!’

“At my age, every day of health is a gift.” She told me, “What you’re looking at is one in a hundred, the lucky survivor. I don’t want to waste one minute of the time I have left. Take your shoe off and give me your foot.”

She rubbed my foot and looked at me; her sexy optimistic smile was beautiful. I took her foot and removed her high heeled shoe carefully. Her foot was smaller than my hand, the skin thin and a bit dry, but the arch very pronounced.

We rubbed each other’s feet and looked into each other’s eyes in silence for a while.

“This is nice.” She said, “You have a hardon. But that’s not enough. I’ve been with a lot of young men. A lot of old men too. Let’s just say I’ve been around. You’re all horny and willing, but how will you feel afterwards? If we go through with it, are you going to feel disgusted when your balls are empty?”

“No.” I promised.

“You’ve only been with two women, thirty and forty. I’m in my sixties, baby.” She said softly, her mirth shelved for a moment. “You don’t know how you’ll feel.”

“I guess we could find out.” I suggested.

“Hmmm.” She said, running one hand up my calf. “You’re eager.”

The feeling of her hands excited me; just as much as Nora, maybe even Joan. The sensitive, smooth touch of the human hand, accompanied by a beautiful smile of desire. I looked into her sparkling blue eyes looking back at me and my cock was iron hard. It was so perfectly wrong, that it was right.

“I like you.” I said.

“I like you too baby. I’ve never been with anyone so young though.” She frowned, thinking about it. “Not even when I was that young. Gosh, that was a long time ago. I’d better drive you home.”

“I thought we were going to get dinner.” I complained.

“Hmmmm.” She said, as we continued our mutual foot rub in the parked Cadillac. “I do like this.”

“Me too.” I said, “Can we just sit here for a while?”

“You’ll want to go higher, and higher.” She predicted.

“Sure, but just like this is nice too.” I countered.

Another of Joan’s lessons in seduction; touch is enough. Once you have touch, even just holding hands, keep it for as long as feels comfortable.

The big car at sunset with Jules felt very comfortable.

“What do you feel right now?” Jules asked.

“Comfortable.” I replied.

She laughed; “Lovely boy.”

We sat in silence for a while, gently stroking, an action that was simultaneously obscene and innocent.

As the sun dropped below the distant city, she released my foot and swiveled back into driving position.

“Well, I asked and you accepted, that’s a date. Ok, we’ll have dinner, but then I’ll take you home to your Mom, ok?”

“Mom will be out working.” I informed her, “But sure, ok.”

“Does she, um, still get a lot of work?”

“Yes.” I said, “It’s been like that my whole life, to me it’s normal. I know not to talk about it, I’ve never told anyone before.”

“Not even your Joan?”

“Not even Joan, but I think she knew.”

The sexy old lady looked thoughtful as she pulled the big car onto the road again, and blasted us towards our next destination with a roar of vaporizing fossil fuel.

We went into a moderately fancy restaurant. I ordered a steak, Jules asked for fish.

She launched into a series of life stories, some sad, some funny, some bawdy.

“Listen twice as much as you talk.” Joan had told me.

I listened, commented, and laughed with my elderly date. I liked being with her, she was like the grandmother I’d never had.

Then she drove me home.

I was hesitant to get out of the big old luxurious car; I had the feeling once I left it, I might not be able to get back in.

“Will I see you again?” I asked. In the darkness, only her white hair was visible, the streetlight refracting through the crystal strands.

“I don’t think so.” She said, with a hint of sadness. “I’m a crazy lady, but you and me is more crazy than I am.”

I heard Joan’s voice in my ear; “Ask for a kiss, hello, goodbye, goodnight, whatever. If the kiss doesn’t work, nothing will.”