Summer of ’88: Pt. 01

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Ahh, the 80’s. MTV still showed music videos, gas was cheap, the video game industry was trying to recover from the video game crash of 1983, and horrible things like reality TV, Hollywood remaking/rebooting movies that didn’t need to be remade/rebooted and political correctness hadn’t ruined everything yet.

For me, 1988 is the year that will always stick out. Not only was that the year I turned 18, not only was that the year movies like Die Hard and Beetlejuice hit the screen, not only were the radio stations ruled by artists like U2, Michael Jackson and Guns N Roses, but it was also the most memorable summer of my life.

Every year, for as long as I can remember my mother and I would visit my grandparents down in Florida, mom would stay for a couple of weeks, go back home leaving me under the care of my grandparents, and come back to get me at the end of the summer before school started back up. Even after my grandfather died in a traffic accident when I was 10, my grandmother Rosie would still be willing to spend the summer with me. My father was out of the picture (according to my mother, they weren’t married when I was conceived, and as soon as he found out she was pregnant, he disappeared), so it was just me and my mother. Despite her busy schedule as an ADA for a prominent law firm, she always made time for me, and part of that included the yearly summer trip to grandma Rosie’s. However in 1988 that changed a bit. Mom was in the middle of a huge trial, and new evidence had come forward that complicated her case. Since this was also before the horrible events of 9/11, it was a lot easier for me to fly solo to see grandma since my mother couldn’t make it. It took a bit of convincing though.

“I don’t know about this, mom.” My mother said to my grandmother, absentmindedly playing with the phone cord as she sat at the kitchen counter.

I rolled my eyes “Come on mom…”

She waved a hand at me, “Shh, Alex, I can’t hear your grandmother. What mom? (pause) I know he can… but… I know you will… but…”

“Diana, if you say ‘but’ one more time I will reach through this phone and spank you like I did when you were a little girl!” I heard my grandmother say through the phone line. I had to laugh, my mother glared at me but said nothing. I couldn’t hear what my grandmother said next, but my mother eventually sighed and said, “All right, mom, fine. I’ll book his ticket for next week.”

After hanging up my mother sighed and brushed her hair out of her face. “That woman…” she mumbled under her breath. “You mister, you’re lucky I love you so much.”

“Mom, I can handle it.” I said, “I’m 18 years old, I just graduated high school, all my college prep is taken care of, plus almost all of my friends are either gone or are getting ready to go away. What am I going to do all summer? I like spending time with you, but this case is gonna keep you busy as hell, and I’m going to be bored as hell. Even Susan is gone.”

Susan was my long time girlfriend, we weren’t sure if our relationship would survive being a long-distance one, but we were willing to give it a try. Spoiler: it didn’t.

“You sound just like your grandmother. She said almost the exact same thing word for word. You’re both right, I’m just nervous is all, you’re flying solo for the first time, and I guess it’s just the mother in me worried about you. I told you before kid, get used to it, I’m always gonna be your mother and I’m always gonna be worried about you.”

For the next week, my mother took any free time to drill into me over and over what I needed to do to make sure I got on the right plane, and triple checked what I packed for the trip. Finally the day arrived and my mother took the time to drive me to the airport, and (again since this was before 9/11) walked me to my gate and didn’t leave the airport until I had boarded the plane. The flight was uneventful and my grandmother was at the airport to meet me, just like she always was when it was me and my mother.

“Alex!” she called out, waving. I hurried over and was nearly suffocated as she pulled me into a bear hug. For a woman in her mid 60’s you wouldn’t know it looking at her. She certainly didn’t look like anyone’s grandmother. At only 5′ 6″, grandma Rosie still had her naturally red hair, bright green eyes, a smile that could light up a room, very few wrinkles and the body of a woman at least 15 years younger. Grandma güvenilir bahis had always kept in great shape, and it ran in the family, as my mother didn’t look like she had just turned 42. Yeah, both grandma and mom had gotten pregnant young, but they were too stubborn to let that stop them from raising good kids and keeping their families together and happy.

“I’m so happy to see you!”

“Grandma… I can’t breathe…”

She laughed and let go of me, and held be back at arm’s length. “Let me look at you! My how you’ve grown since I saw you last!”

“Grandma, you saw me just last year and I know mom sent you copies of my graduation pictures.” I said as we headed to baggage claim. “You’ve seen me recently.”

She hooked an arm inside mine as we walked, “Yes, but not in person. You’re taller than when I last saw you, you had a growth spurt since last year.”

Well, that was true. I had shot up three inches and was now just a hair over six feet tall. We grabbed my bags from baggage claim and headed to her house, grandma grilling me about my senior year in high school and my life in general as she drove, and telling me about all the fun we were going to have over the summer.

The first few days were pretty routine. Grandma drove me around town, showing me what had changed since last I visited, as well as telling me what else she had planned. Since this was before the internet, some of our plans changed on the fly.

One day, during my second week there, we hit the beach and I had a hard time keeping my excitement hidden from staring at all the bikini clad girls on the beach. I kept having to adjust my johnson to keep it from tenting the front of my swimsuit. If grandma noticed she never said anything. Later that night, after dinner, grandma went to take a shower before she went to bed, I sat in the guest bedroom she had set up for me, but the image of all those bikini clad girls on the beach kept jumping into my head. I closed the door to my room and lay back on the bed pulling out my rapidly hardening cock. My thoughts kept jumping back and forth between the girls on the beach and the few times Susan and I had sex (or the naked fumbling around we did that passed for sex), my hand moving faster and faster on my now rock hard dick, my eyes closed, and my breathing getting ragged. Just as I was about to explode the door swung open. “Alex, I… oh my!”

Grandma’s voice snapped me out of my erotic daydream and I quickly pulled the covers over me and turned away from the door, “Shit! Uh, sorry grandma but… um…”

For a long moment neither one of us knew what to say. I couldn’t even look at her, I just kind of stared at the wall. “Could you… um… you know…” I waved her off with my free hand.

“Oh! Sorry, honey, sure. I just wanted to say good night.” Grandma Rosie said.

“Good night.” I said a little too quickly.

I heard the door close and for a long moment just lay there until I heard her bedroom door close down the hall. “Well that was embarrassing.” I said to myself. I rolled over onto my back, and surprisingly I was still hard. I didn’t realize it at the time, but there was a small part of me that was kind of excited that grandma Rosie had caught me masturbating. I surprised myself when I grabbed my cock and picked up where I left off. Stroking myself even faster than before, the last image in my mind before I blew my load was grandma opening the door and catching me mid stroke. I groaned quietly as I exploded all over my hand and chest with the image of grandma standing in the door frozen in my mind’s eye.

“Did I really just cum to that?” I thought to myself as I grabbed a couple of tissues to clean myself up. “I guess I did.” My heart was still beating a million miles an hour as I turned off the light and rolled over and went to sleep.

The next morning over breakfast grandma didn’t mention what happened last night, but I still found it hard to look at her as I mostly pushed my food around on the plate. It was raining that day so we cancelled our plans for the park and went to a movie instead. I had almost forgotten about getting caught the night before, but I found myself looking at grandma in a new light. Especially after the movie when a strong gust of wind snatched the umbrella out of grandma’s hands in the parking lot. I chased it down but it was hopeless, and I retreated to the car, the both of us soaking türkçe bahis wet, and I caught myself checking out how grandma’s soaking wet clothes stuck to her body. We laughed it off and headed back to her house the heater in the car going full blast in an attempt to dry us out. My eyes flicking back and forth between the rain soaked streets and grandma’s shirt clinging to her chest. I tried to be sneaky about adjusting my erection.

Later that night my stomach was growling so I headed to the kitchen for a snack, as I passed the bathroom I could hear grandma in the shower and I noticed the door was open a crack. I caught sight of my grandmother as the shower curtain was open just enough for me to see her. She had her back turned to me and again my dick jumped to attention. My brain started arguing with itself. “Damn, grandma has a nice ass for an older woman.” “Dude, that’s your grandmother!” “Yeah, so? We were checking out her rain soaked tits in the car!” Then grandma turned around and I backed away a bit, but she didn’t seem to notice me, and for the first time I saw my grandmother fully nude. Her tits were even more amazing than I had imagined. Nice and firm with just the slightest bit of sag, and yes, the carpet matched the drapes. I couldn’t help myself and pulled my now hard cock free of my shorts and started stroking it as I watched my grandmother soap herself up. “I wish those were my hands.” the little voice inside my head said. I stayed rooted in place, slowly stroking my cock as I spied on my grandmother. I panicked when she turned off the shower and quickly moved away from the bathroom door, pulling my shorts back up and went to the kitchen to grab a soda, my appetite forgotten.

I made it there and back to the bedroom while grandma was still in the bathroom. I closed the door behind me and went back to the book I was reading. I heard grandma walk down the hall to her room, and a few minutes later there was a soft knock at the door. “Alex? Is it safe?”

“Yeah, grandma,” I said.

She opened the door, dressed in a over sized nightshirt and pajama bottoms. “Come with me. I want to talk to you about the other night.”

I felt a ball of ice form in my stomach, I knew this was coming, but part of me was hoping that since she didn’t mention it during the day that maybe she wouldn’t bring it up at all. I followed her to her room where she sat down on the bed and encouraged me to sit next to her.

“I’m sorry.” I blurted out.

“There’s nothing to be sorry for.” She said, “You’re a teenage boy and I know you have certain… urges at your age. You forget, your mother wasn’t the only child I raised. That’s not the first time I caught someone doing that.”

The unwanted image of my uncle Joe getting caught masturbating by my grandmother jumped into my head. Uncle Joe was the reason I didn’t have any cousins to play with during my summers with grandma. If you look up white trash in the dictionary, you’d see a picture of my uncle Joe. He was single, unemployed due to an accident, and spent his disability checks on booze. I pushed the image out of my head. I hadn’t looked directly at grandma since I sat down, staring at the floor. She picked my head up to look at her.

“Alex, it’s okay. I just want you to know you don’t have to hide that from me.”

My eyes went wide and it took me a minute to form words as my brain tried to process what she had just said. “But isn’t that something you know, you normally do in private?”

“It doesn’t have to be.” she said, my mind was reeling. Was this going where I thought it was going? “I have a confession to make. I masturbated quite a lot after your grandfather died.”


“I’m serious Alex. It’s been quite a while though, and seeing you, well it brought back the memories of him.” she said, now it was her turn to turn away from me, but it was to look at his picture on the nightstand. “It’s been a long time since I’ve seen a man’s penis.”

And I was hard again.

“Grandma, what are you saying?”

“I think you know.”

Holy shit! My grandmother wanted me to masturbate for her? “I don’t know about this. I mean, I’ve never done it in front of anyone before.”

“Not even that girl you’re dating?”

“No, not even for her.”

“Look at it this way, at least you’ll be doing it for an appreciatve audience.” she said, glancing down “Plus it looks like you need the release güvenilir bahis siteleri anyway.”

The outline of my cock was clearly visible through my shorts, and I had almost gotten off watching her in the shower earlier. Oh, shit. Did she know about that? She was right though, my cock was throbbing and all I could think about was finishing what I started outside the bathroom earlier. As eager as I was, I was also nervous as hell.

“This is just between us, right?” I asked.

“Our little secret.” she said, “Do really think I’m going to tell your mother about this?”

I laughed in spite of the nervous energy running through my body. I lay down on grandma’s bed, and she sat on the edge watching me as I pulled my shorts and underwear off. My cock sprang free almost pointing towards the ceiling. I heard grandma let out a gasp and glanced over to see her eyes were glued to my cock. Taking a deep breath I grabbed my cock and slowly started stroking it, from balls to the head, my eyes slowly closing as the images of the bikini clad girls on the beach, grandma’s tits in her wet t-shirt, grandma’s body in the shower danced behind my eyes. I found my thoughts focused more and more on my grandmother, I imagined she had stayed and watched me last night, or that she had put on a show for me in the shower, and of course knowing she was watching me now. I picked up the pace and opened my eyes. Grandma Rosie still had all her attention on my swollen cock. She looked at me and smiled. “Do you want to see what you were looking at in the car? I know you were looking at them.” Her voice had dropped down to a sultry whisper. I could only nod quietly as I started stroking my cock faster and faster. Pre-cum was leaking out and I used that to lubricate myself and keep up the faster pace. Without another word grandma pulled the nightshirt off to reveal her huge tits to me. “They’re magnificent grandma.” I almost came right there, but I slowed down the pace a bit. Now that I was getting into this, I wanted it to last.

I could feel sweat beading on my body, I paused a moment to sit up and pull off my shirt and then got back to work, my eyes glued to grandma’s chest. She started rubbing her tits for me, our eyes meeting. She reached over and brushed my hair out of my face and I closed my eyes as I felt her hand gently wiping the sweat off my forehead and stroking my hair. I felt movement on the bed and opened my eyes again to see grandma was pulling her bottoms off and then she lay down on the bed next to me and her hand disappeared between her legs. Not only was I masturbating for my grandmother, now she was masturbating for me! I watched her hand move between the thatch of red hair between her legs, and she started moaning quietly as she rubbed her fingers over her clit.

She stopped just for a moment to rearrange the pillows behind us so we could easier look down each others bodies as we continued our mutual masturbation. My eyes traveled up and down her body, I watched her hand between her legs, and could hear the squishing sound as she sank two fingers into herself and started vigorously finger fucking herself, then I watched her tits bounce as she got herself off, finally looking at her face as her eyes were closed and her breathing, along with mine grew ragged. “I don’t know how much longer I can hold out.” I gasped.

Grandma looked at me, “Then don’t. Cum for me Alex. Let grandma see it.”

That was it, I lost it, I felt the familiar sensation in my balls and then groaned as my orgasm hit like a freight train. I didn’t just cum, I fucking exploded. Jet after jet of cum shot out of my cock and landed on my chest, arms and I even got some on grandma as I was stroking myself at a machine gun pace my body jerking around like a fish out of water. Just as I finished up I heard grandma moaning, and realized she was coming. Much like me, her body started spasming as her orgasm hit. I could only watch as her body twitched and jumped, her tits bouncing around her chest, her hair plastered to her sweat covered face.

Finally we both came down, catching our breath. Grandma grabbed a handful of tissues from the nightstand and gave them to me to clean myself up and took some to clean herself up as well. That’s when it really hit me. I had just masturbated with my grandmother, not just for her, but with her!

“See, that wasn’t so bad now, was it?” grandma asked, brushing her hair out of her face.

“Not at all.” I said.

She leaned over and gave me a kiss on the cheek. “Now, no more hiding that from me, understand?”

Oh, I understood her just fine. But my unforgettable summer was just beginning.

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