Chapter 1: Skater Boy Meets a GILF

I first saw her at the skate park; she used to come and watch. Sometimes when someone would make a particularly smooth move, she’d clap and shout out a compliment. I thought she was around 45 years old, because her face was just beginning to crease, and she was still good looking even though her hair was half black and half grey. It was her smile; the way she smiled when I caught her eye, the way she looked at me instead of past me, or though me like most people did.

I was poor; I lived in a group home paid for (barely) by the state. I wore old clothes and my hair was ragged. Even my skateboard was a gift from a friend.

I can’t really pin down when we started flirting; it sort of developed. A word, a smile, a sentence; when we met we’d both be happy, sit and talk for a while. I found myself thinking of her when I jerked off, which was weird; but I never worried about it. I was 15 and I jerked off to all sorts of women.

I was always hungry; and Cucthao brought food. Spicy meat sandwiches and hot tea in a thermos. She seemed to love feeding me, and I sure loved to eat. We laughed, talked, and I became aware of a sexual tension that was crazy and fun. I didn’t think it would go anywhere, I just enjoyed it.

I was an orphan, sort of. My dad had vanished and my mom was in jail, I didn’t do well in school.

Then I noticed that she was dressing pretty sharp; and that the old woman had a hot bod. Tight ass, narrow waist, decent tits as far as I could tell. And she had this great hair, thick and long, styled in different ways, elegant with the grey streaks. And she wore a little makeup, and smelled great all the time.

“Hi Freddy!” she called out with a wave and a smile as she took her usual seat, spreading her skirt around her knees. It was late, just after sunset and I’d been about to go home.

“Your hair looks great today.” I told her as I popped up out of the halfpipe and flipped my board up into my hand. She seemed to light up; I really liked that, and made a note to compliment her again.

“You don’t think I should color it?” she asked, running her fingers through it and shaking it out.

“Nah, I think it’s great like it is, it suites you; the way it frames your face is nice.”

Her smile got even brighter and she sort of stretched herself.

“It’s a lot of work though, brushing it every day. You don’t think I should cut it short?”

“No! don’t do that.” I exclaimed.

“Well, if you like it then you should brush it.” She suggested, and then seemed embarrassed and looked away.

This was the moment; I felt myself crunch together, terrified and thrilled. She was giving me an opening, and it was up to me to take it, if I had the guts. I could just laugh, make it a joke. Or...

“I’ll brush it for you.” I said brashly. Brashly? Yeah. I was surprised too.

Her hand reached into her bag, and brought out a hairbrush. Right there in daylight, in the skatepark.

I was more than a virgin; I’d never even touched a woman or a girl. Then I thought; hey, it’s just hair. Friends do hair, maybe she thought I was gay or obviously too young, it didn’t mean anything more than what it was. I stood behind the park bench and pulled the brush through her beautiful mane, noting the decreasing percentage of remaining black strands as I ran my fingers through the smooth wonderful locks with one hand while brushing with the other.

She sat still, straight backed. I couldn’t see her face; did she like it, was this nice for her? I wanted to ask, but couldn’t say anything. So I kept brushing as the night cooled around us.

“Ok, that’s enough.” She said softly, standing and turning to face me across the bench. I gave her the brush back, we said our goodnights, and I went back to the house and jerked off thinking of her as I took my shower.

I brushed her hair almost every evening after that. We both sat on the bench, she twisted away. One time, it was a hot night, and she had naked shoulders. I couldn’t resist, and I let my fingertips trace across them. She said nothing, I brushed some more, and then stroked her shoulders again. She shivered and got goosebumps. I had a hardon. That was our first sex I guess. Just a touch, nothing, yet everything. Because there was no excuse. I did it, I liked it, and she seemed to like it too.

I waited anxiously the following afternoon, looking for her each time I popped up out of the halfpipe. And when I saw her, my heart did a little jump. And she smiled, and took her seat to watch us.

Some kids stayed late, just before I was going to tell them to fuck off, they left us alone. I went to her; she stood and faced me. Small, vulnerable, sweet, beautiful. she reached up and touched my face, looking into my eyes in the half light.

Would she kiss me? What should I do? Then I realized she wouldn’t. Despite the age gap, I was the guy, she was the gal. If it was going to happen, it was up to me. I wasn’t sure how to do it; I moved closer. Closer, until our bodies nearly touched. I bent my neck, she tilted her face up, she could step back, or turn away. She didn’t. slowly, so slowly it took an age to get there, slowly I brought my lips to her lips, and the soft moist thrill of my first kiss was with a Vietnamese grandmother.

I didn’t yet know that she was a grandmother. It wouldn’t have mattered. My arms went around her slim little body, and gently pulled her tight. She gasped, squirmed, and held me tight too. my hands felt the shape of her back, the indentation of her spine, the wonderful heat her body held.

Our kiss was endless, a forever kiss, even though the physical part ceased after a while the memory of it still heats me up. I can still feel her breasts pushing against me, her hands on my face, her thigh pressing against my groin.

“Oh Freddy!” Cucthao gasped, braking away, “We can’t do this!”

“Why not?” I asked.

“You know why, you’re a schoolboy and I’m a grandmother.”

“So?” I responded, my head reeling in the new information; grandmother? Maybe she was older that I’d thought. What was the youngest possible age for a grandmother? “I like you, and that was nice.”

She picked up her shoulder bag with a tolerant laugh; “I like you too, let’s just use our mouths for talking, ok?”

She walked off into the dark; I followed her, watching until she got home. A nice house, freestanding with a fenced yard, lights in the windows.

I was afraid she’d avoid me after that, so I was happy to see her when she turned up as usual, and took her place to watch us ride our boards around the tubes.

“Hey, your granny is here.” One of the guys told me.

When I stopped for a break, she waved me over and gave me two sandwiches and a big glass of ice tea. She spent about half her time punching an Ipad. She was writing a short story, and asked my help with dialog.

“You shouldn’t look at me that way.” She admonished me, “It makes me feel funny. Did you get your exam results?”

“Yeah, flunked math, English, and history.”

“You studied though, so what happened?”

“I don’t know, I thought I was doing ok. I guess my teachers are right, I’m just dumb. Here, I have the marked papers.”

I handed over the handwritten sheets covered in red lines and circles.

“Your teachers said that to you?” she demanded angrily, which was sort of sweet. “I was a teacher you know, in Vietnam.” She put her glasses on and looked closely for a while.

“This essay, it’s good except for spelling mistakes. You always inverse your vowels. And this math, same thing. You have the correct numbers in the wrong order. I don’t know this history, probably you just have the dates wrong. Freddy, you’re not dumb. You’re dyslexic.”

The next day at school, I was called into the office; I practically jumped out of my skin when I saw her there.

“Fredrick, your grandmother has brought it to our attention that you have a learning impediment.” The principle said to me.

Fuck, I thought; now I’d get thrown out, or maybe sent to a school for idiots. I was about to tell her that Cucthao wasn’t really my granny.

“We have a program for dyslexia, you can sit the exam again.” She continued. “Don’t you have access to a computer? A spell checker would catch most of this.”

“He can use my computer.” Cucthao said.

I was allowed to use a calculator too, and given extra time to double check my answers. Thanks to Cucthao’s interference, I had a hope of graduating high school.

I loved her then; loved her for seeing me as more than a skater boy, more than a dumb homeless loser. She fed me, stood up for me, saw me as a human, a person who might do ok.

“Freddy, why are you looking at me that way?” She admonished me again.

The other kids had gone and it was getting dark. We were sitting on our bench, close, so close. My hand reached up behind her and my fingers ran through her lovely hair.

She moaned, or sighed. And we kissed again. I would have just sat there and kissed her all night; her hand landed on my thigh. Well, on my stiff cock that was against my thigh.

“Oh Freddy!” She laughed, “You have a big cock.”

We kissed some more as her hand kneaded my rod through my pants; my mind seemed to float away on a sea of sensuality.

“Want to come to my house?” She asked.

“Yes.” I agreed.

We walked in silence, holding hands. How I loved her then; I just fucking loved her, I wanted to hold her, kiss her, be with her, protect her, sleep in her bed. Yeah, and fuck her; I really wanted to do it with her, yet if that never happened I’d love her anyway.

The house was dark, no one was home. She unlocked the door and we went inside. She switched on the light and turned to face me, looking up into my face with her dark slanted eyes. I took her face in my hands, my fingers in her hair, thrilled to be there with her, to look at her in the light in private, and have her look at me the same way.

“Not yet.” She said softly, pushing me away. “We have all night, my daughter and grand-daughter are away. You need a shower, and I need to prepare myself. Here, use this one, and then wait for me.”

I came out of the shower wearing just a towel. I sat on her bed nervously, my mind spinning in opposite directions. It was going to be great, no, this was crazy, can’t fuck a granny, yes, sure I can, why not? No one else was interested, and she was wonderful.

All doubts evaporated when I saw her; her hair down to her tits, she was wearing a gleaming black robe that barely covered her ass, and was clinched at her narrow waist by a knotted belt. Her legs and feet were uncovered. She looked at me with a steady gaze and a smile as she floated to the bed, and sat on the other side.

“I’m not so sure about this, Freddy.” She said softly as I slid towards her, “It’s been a long time since I had a boyfriend. I don’t know if everything still works.”

My hand slipped into her robe, and found her warm skin. My cock lifted the towel to the side, and she put her cool hand on it. A sensation I’d never even imagined, her touch on my penis shocked me with intense pleasure.

“You like that?” She teased. “Don’t worry, I can take care of it for you.”

I took her beautiful face in my hands, and kissed her again, and she cupped my balls and gently stroked my hot hard penis, and it was the greatest feeling I’d ever known.

I opened the robe, exposing her breasts, which were supported by a lacy half bra, big nipples pointed at my heart. Her small body, so sexy, ageless, warm, delicious, and mine for the night. To love, cherish, hold, worship. All I wanted to do was this; kiss, touch, tickle. Nothing could be better, I thought.

Until she went down on me.

Oh man, her mouth! My virgin cock in her gorgeous old mouth, her eyes looking up at me as her face slowly moved down my shaft, then up again, releasing me for a moment before doing it again, slowly, so slowly.

Not like those frantic porn girls in the videos I’d watched; Cucthao wasn’t trying to make me come. She was keeping me in a state of extended ecstasy, sucking my stiff rod for our mutual pleasure.

My doubts were gone now; she was a great lover, experienced, knowledgeable in the art of lovemaking. As I looked into her soft dark eyes, her mouth around my throbbing hot penis, my fingers in her silky greying hair, I knew that she was giving me the greatest gift that could be given.

Her love.

“You want to come in my mouth?” she asked breathlessly.

“No.” I answered brashly as I pushed her onto her back, only to see she was wearing no panties; also, she had no pubic hair. That was really nice; a hairless pussy had no age. Her legs opened and her slot opened too, pink and succulent.

I looked into her eyes the same way she’d looked into mine as I went down on her.

To be honest, I was only doing it because it was what I thought I had to do. As soon as my tongue tasted her though, my doubts disappeared. That taste, it went straight to my brain, and then to my balls. I loved that taste, the deep tangy salty flavor of her pleasure.

Her hands held my head, her hips bucked upward, and I could see the joy in her eyes, mixed with surprise. I had no idea how to do it; I sucked a little, put my tongue in, moved it around, and watched her for signals, felt her hands flutter and squeeze my head, emotions flitting across her face as I wallowed between her thighs.

“Freddy, Freddy!” she laughed, “You’re such a good boy, now that’s enough of that, put your thing inside me, let’s do it.”