Sex with Grandma
- 2 years ago
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Jeffery free porn video
My girly girlfriend Casey has this great big treehouse in this huge old oak tree in her back yard. She tells me her dad built it for her when she was like four years old, but it's big enough for a couple of teenagers to spend the night in. She has sleep-overs in it all the time. Her dad even ran a phone line out there so she could call them if she needed them. S eesh!
One Friday night in April, she told me to sneak out and come see her for a few minutes.
"Be there by eight! But if you're not there by 8:30, don't come at all!"
"Fine. I'll be there at eight," I replied, pretending to be annoyed. But I could never be mad at her, and she knew it. She was just too beautiful. She could melt me with a smile.
At around 7:55, I was scaling the back wall of her property. Her parents are rich, and her yard is huge. The wall is about seven feet high, but covered along its entire length with Virginia creeper. If you stand on an upturned garbage can, and then jump up a little, you can grab the low-hanging vines and pull yourself up. Well, most people couldn't, but I'm pretty strong.
Anyway, I got up to the top of the wall, carefully got to my feet, and then leaned as far as I could to grab a branch of the great old oak tree. It was tough to do in the gathering gloom. I could hardly see it. I almost fell. I always almost fall. But I managed to catch it with one hand and then swing over to the back wall of the treehouse. One day that damn branch is just gonna snap on me. But it didn't that day.
I stood on a gnarly old limb next to the back window and waited. The back window was basically a rectangle cut out of the wooden wall, with a sill on it. I didn't peek in yet. She wasn't there. She told me never to peek in because sometimes her mom comes out there with her, helping her carry her blankets and pillows and such. I just waited.
It was a nice night. In April in our city, the sun goes down around 7:30. There was still some light in the western sky, but the stars were coming out. There was a cool breeze that made me kinda wish I'd brought a sweater. My T-shirt was damp from the run all the way to Casey's house, and now I was chilly. But I waited patiently. My watch said 8:02.
A few minutes later, she came out. I heard voices murmuring as the two women crossed the back lawn. They climbed the slats on the trunk of the tree that served as a makeshift ladder and flipped the trap door open. The door thunked against the tree. Light spilled out of the window from her lantern. I held my breath.
"You want me to call you when your little friend gets here?" her mom said.
"Mom, she's taller than me."
"Well, compared to me, everyone's little. Especially you, little pixie."
"Sure. Call me. I'm just gonna read for a few minutes."
"Take your sleeping bag..."
"Thanks."
"Here's your pillow."
"'Kay."
"Your magazine."
There was a fluttering of pages. Casey took it.
"And here's some cookies. Don't eat them all."
"Thanks."
"Now gimmie a hug."
They hugged, I assume. All I heard was the rustle of cloth. I pictured Casey sitting next to the trap door on her sleeping bag, and her mom standing on the second last rung of the ladder, leaning in to hug her. I'd never actually climbed down that ladder, though I'd been in that treehouse many times. I always exited the way I came in, nearly killing myself trying to swing back onto the top of the wall, most of the time in the dark.
"Aren't you gonna be cold out here dressed like that?" her mom asked.
"Mom," she said, sounding annoyed. "That's what the sleeping bag's for."
"All right. Fine. Just asking. Call if you need anything. And you come straight inside when it's time for her to go. I don't want you sleeping out here by yourself."
"Yeah, yeah. I know. You've told me a thousand times."
There was a thump as the trap door was shut behind her, and then barely perceptible footsteps striding across the grass back to the house. Her mother muttered to herself about crazy kid this and die of hypothermia that. The last thing I heard was, " ... not even wearing pants!" I became suddenly excited.
A minute later, after a slam of the back door of the house, an arm extended out from the back window, holding the lantern. And then a pretty little face leaned out and turned to see me awkwardly crouched on the tree like some sort of costumeless ninja, ready to pounce. I just looked up at her and sighed.
"Good evening, miss!"
"Comfy?" she said.
"Not really."
"Been waiting long?"
"Five million years."
"Shut up, you goof."
Casey was absolutely gorgeous. She's petite, just over five feet tall. Her eyes only come up to my chin. She has to stand on her tiptoes to kiss me when we're standing up. She has short reddish-brown hair, auburn, I think they call it, but it's more reddish than brown. She has green eyes that light up and sparkle when she laughs, but they're magical when she smiles. Her cheeks are covered in the most adorable freckles. She's got nice little boobies, too, and a butt so cute and round and bouncy, you'd almost risk going to jail just to grab it and give it a nice firm squeeze. She lets me grab it all the time, though, so no worries for me.
She was indeed barely wearing anything at all. She had a little red night shirt on that came down to the tops of her thighs, and that was it. Leaning out the window like she was, I could see her panty-covered butt. I hummed in appreciation.
"Mmmmm-mmmmm... !"
"Stop it, you perv! Get in here!"
She leaned back and I climbed in. Moments later, she was kissing me like we'd just fought an epic battle against the world's ending and finally found each other again after a life-and-death struggle. Cue the brass section. Cue the strings. Forte!
Ah, who'm I kidding? She's just really horny all the time, and God, do I love her for it.
She shoved me back onto the sleeping bag, swung one leg over, planted her plump and puffy, panty-covered pussy right onto the crotch of my sweat pants, and went crazy on me, kissing me, shoving her boobies into my chest, grinding on me, moaning, and sighing happily. She practically devoured me, to be honest. Not that I was complaining. Her tongue in my mouth was like candy. Within moments I was hard as a rock, bent awkwardly sideways down there, almost poking right out of my sweats. And I was moaning into her excited little kiss as she stroked her damp little mound against me. Oh, man, I could feel everything, so soft and wriggly.
"Shhh!" she kept reminding me. "You're too noisy!"
Like I could help it! We kissed even more, until finally it was her who was moaning.
"I love you, I love you, I love you! My beautiful sexy boyfriend!"
"I love you, too," I whispered. "Wanna fuck?"
She climbed off me and sat up. "You wish."
"I sure do."
"Just shut up and listen! My friend is coming over in a few minutes. Her parents are visiting my parents, and she's going to hang out with me out here while they're busy in there doing ... whatever the hell they're doing."
"I heard your mom say something like that. So why did you need me here?"
"Because I have to fill you in on the plan before I tell her!"
"There's a plan?"
"Just shut up and listen!"
"I'm listening! I'm listening!"
I pretended to be annoyed again, but I was looking down at her little B-cup boobies in the lantern light. They were amazing. She wasn't even wearing a bra.
She punched me in the chest. "Pay attention!"
"Okay!" I replied in a loud whisper, rubbing the little injury a bit. She packed quite a wallop.
"Here's the plan! Two magical things are happening on Monday."
"Such as... ?"
"Well, first of all. You don't have school, and I do."
"True," I said. I went to public school. She went to a private girls' school. St. Mary the Perpetual Cherry, or something like that. At least that's what my buddies at school called it. Anyway, we normal kids had Monday off for a teacher's training day or something. The Cherry girls had no such luck.
Casey talked very fast, explaining the details to me, and the whole time, she was shoving and smacking my hands away as I moved to grab her and caress her and fondle the various parts of her pretty little female form. She even dodged my kisses when I tried to kiss her again. She really wanted to get the story out.
"The second magic thing is, I just happen to know that our Janitor, Martha Wallabee, is going to be away on Monday. I was in the office today, picking up some photocopies for our science teacher, Mrs. Angelo, and I heard Martha talking to the secretary about how she had to move her day off from Wednesday to Monday because the painters screwed up their schedule. The secretary was all in a huff and told her she's lucky she's even getting a day off, how the school would be absolutely wrecked by the time she got back, but Martha told her to stuff it. I'm pretty sure she was just kidding."
She said all that so fast, my head almost popped from the overload of information. But my logical male mind got the gist of it anyway: the school janitor was going to be away on Monday. I finally managed to get a kiss in on her neck.
"So what?" I said. "So Martha's getting her house painted. Why is that so magical?"
"Because, stupid! The Maintenance Room!"
I felt like I was hearing an inside joke that I wasn't in on.
"I don't get it. That supposed to mean something to me?"
"Don't you remember? That day we went to the Ice Cream Castle last November! I told you about the boiler room and how the door doesn't even have a lock on it, and the only thing keeping anybody out of it is the sign that says KEEP OUT! People can just pretty much go in and out of there whenever they want! It's right next to the girls' washroom by the back door of the school!"
"And?" I said, still confused. If there was a point to all of this, she sure wasn't making a long story short.
"And I'm the only one who knows about it! I saw Martha go strolling in there one day without even unlocking the door. She has to take out her keys and unlock every other door in the school, but not that one. She just opens the door and goes in. There's a lock on the door, but it must be broken or something. Or maybe she goes in and out of there so many times during the day, she just doesn't bother locking it any more. It looks broken to me, though. Maybe she lost the keys at some point and had to break in. I have no idea. I peeked in there one day, just to look. There's all kinds of machines, and electrical panels, and fans and air ducts and stuff. I guess the furnace and air conditioner and fuse boxes and everything are in there, for the whole school. I'm pretty sure Martha sneaks in there for a smoke break, or a nap or whatever. I'm not sure, but all I know is, that door doesn't have a lock on it, and from what I saw, it's huge in there!"
"How magical," I said, teasing her. She smacked me in the chest again. In retaliation, I gave her left boob a little jab with two fingers, getting a bit of a nice feel for half a second. She didn't even smack my hand away. She just looked down for a moment, and then scowled at me.
"It's a good thing you're so gorgeous because you sure are dumb!" she told me.
"Hey, now! That's not nice." I wasn't mad of course. Her creamy white thighs were exposed before me, and sitting cross-legged like she was, I could see the crotch of her little white panties.
"Don't you get it!? I'm gonna sneak you into the school! We can have an extended make-out session, with no worries of being caught, no time limits. Just a whole hour, all to ourselves! You're off school, I'm not, and Martha Wallabee won't be there. So basically nobody will interrupt us! We can do whatever we want."
That did sound very nice. We'd been dating for nearly a year, but so far, our longest make-out sessions had been twenty minutes or so up in the treehouse. But even then, we were scared half to death of hearing the back door slam and me having to scramble out the window in a mad rush, nearly killing myself. It happened all the time. The only time they ever let her stay out there overnight was when she had a friend with her, and that was eliminated any sort of heavy duty making out we might have planned. Her friends from school were all tight-asses who thought even kissing a boy made you a whore. None of them even knew she had a boyfriend as far as I knew.
But now she'd come up with this once-in-a-lifetime plan to have a whole hour alone together. I was giddy to say the least. It would be almost like we were married or something!
"Well, we better fuck right now then, just for practice!" I told her, reaching for the crotch of her panties with two fingers. She did smack my hand away this time.
"This is the thing, stupid! It's your birthday on Monday, too! So that makes it extra special!"
"So it is," I murmured. "You're gonna fuck me on Monday, then?"
I flinched expecting another smack, but she just raised an eyebrow. "Well, I am going to give you... something."
My heart nearly exploded in my chest. My eyebrow shot up, questioning. Up to this point, she hadn't let me do anything more than grab her boobs and ass above the clothes. She'd grabbed my dick once, but it was purely by accident. At least I think so, anyway. She'd moved to get up and she'd put her hand on what she thought was my thigh. When she'd felt a weird, elongated bulge, she'd given it a curious squeeze, wondering what it was. Then she looked down and gasped, yanking her hand away. That was the most action I'd ever gotten out of her. It was pathetic and glorious at the same time.
But now she was planning, well... something.
"But this still doesn't explain why you need to let your friend in on this whole mess," I said.
"Well, d'uh! It's not a hundred percent fool-proof. There's still a very small chance someone could come along. We need someone for a look-out."
"Okay. Makes sense."
"The only thing you need to know is to be at my school, waiting by the back door on the Kingsway side, at exactly 9:55 am on Monday, by the parking lot. Nobody can see you walk up from that side. The doors are locked from the outside, but I'll let you in. Let me handle everything else. I have a study period in the library from 10 to 11. But the librarian is so out of it most of the time, she won't even notice if I'm gone the whole period, and if she does, I'll just say I had girl troubles in the bathroom."
"Boy, you really have planned all this out, haven't you?"
"I've been dreaming about it for months. Now shut up and kiss me."
We kissed, and somewhere in the kiss, I rolled her onto her back and found myself mounted comfortably between her legs. She had them pulled right up to her shoulders, in fact, and everything was hot and humid down there. My erection was pressed so deliciously into her plump little mound that I nearly came in my pants with every move she made. And boy did she move! It was almost like we were having sex for real! If not for our clothes, we would have been.
Like I said, for such a prim and proper, well-raised girl, she sure was horny when you got her alone. She rocked and bumped and thrust up and down against me, and she squealed and moaned into our kisses when I grabbed her boob with one hand. She tried to yank my hand away at first, but then relented, sliding her hand up to caress my back instead. I enjoyed the feel of her soft round breast over her shirt. It wasn't nearly enough, but I had to take what I could get.
Finally she tore herself away and shoved me off of her. My erection was now thrusting out the top of my sweat pants. She was about to say something, but she just gaped at it for a moment in the lantern light. Her mouth dropped open. Her eye sparkled a little. But she quickly snapped out of it.
"Put that away!" she said, as though she were talking about a piece of stray cutlery or something. I tucked it back into my pants. She moved to the front window and glanced out. "I think they're here," she said. "You better go."
The phone rang on the wall beside her and the back door flew open with a bang at the exact same moment. A girl came hurrying across the lawn. She quickly shushed me (as if she needed to), and waved me out the back window. I went. She grabbed me and gave me one last kiss. The phone rang on. "Go! Hurry!" she said in an impatient whisper. And then she picked up the phone. "Hi. Yeah. I see her. Thanks." And she slammed it down again.
The trapdoor banged open before I even had a chance to get my balance to walk across the tree limb and swing down to the wall. I couldn't go now. Her friend would hear me, especially if I fell! So I crouched down in the ninja pose again and waited. God, I hoped her friend wouldn't be there long. I still had a frickin' hard-on.
"S'up, girlfriend!" a girl's voice said. It sounded sweet and musical, the kind of girl who probably would have made a great singer. She sounded about Casey's age. They must be classmates.
But then her tone changed almost immediate. "Holy! You okay? You look all messed up, like you just saw a ghost!"
Yikes! Apparently, the hot and heavy make-out session was still showing on Casey's face.
"You startled me! That's all. Don't come crashing up through the trap door like that!"
Nice cover, I thought to myself.
"Sorry!" her friend said, sheepishly.
I wondered if she was hot. She sure sounded like it. I mean, I wasn't about to go cheating on Casey or anything. I loved her with all my heart. But a hot girl was still nice to look at, as long as you don't say anything to your girlfriend about it and don't get caught staring. Casey always tested me, asking me which girls I thought were hot as we walked around together or sat in a coffee shop. I always told her nobody was as hot as she was, and to me, it was true. But a guy can still look sometimes.
Her friend closed the trapdoor again with a gentle thump.
"So what's the big secret you had to tell me?" the girl said.
"Okay! Sit down. It's kind of a long story."
"Is it a sexy story?" her friend asked, with a naughty giggle.
"Oh God! You're such a perv!" Casey replied. "Si' down!"
The girl sat.
"Boy, it's cold out here. Your nipples are like, solid!" the girl commented casually.
"So are yours!" Casey said back, sounding defensive. I think she was worried her friend would suspect she'd just had a boy grabbing those very same boobs not five minutes ago.
"Mine are always like that! So embarrassing!"
"That's because you're always horny and thinking about boys, ya perv!"
The girl giggled again. Yummy! I thought to myself.
"I love your hair, by the way," Casey said, suddenly changing the subject. Sheesh. How girly. I wished she'd get to the point.
"Thanks," the girl said. "I went with pony tails today."
"It's cute. But they're like, nearly covering your boobs. You'll never get a boyfriend if you keep covering your boobs like that."
So she had long hair, and she was single. Not that I was gonna go hit on her or anything. I was just gathering information, that's all.
"As if I'll ever have a boyfriend anyway!" she said in a sad, pouting tone.
Casey paused. My legs were slowly cramping. It was getting colder. Finally, she continued, beginning with a long sigh.
"Well, speaking of boyfriends, this is what I had to tell you."
"No way!" the girl said. "You have a boyfriend!? Oh my God! Is he hot!? Have you, like, kissed him and everything!? How far have you gone!?"
Boy, she'd jumped to those conclusions pretty quick! She wasn't wrong, though. She was a sharp one, whoever she was.
"Just wait! I'll get to it!" Casey said, feigning exasperation. "God! Such a perv!"
Casey told her the whole story. I listened with increasingly cramping legs, smiling at the memories. Eventually, I just slid my feet out from under me and hung them down on each side of the limb, sitting instead of crouching. It was still murder on the ass after a while, though.
We'd met at a little dessert place near my house, near their school. The Ice Cream Castle. She'd walked in wearing her little school uniform, red tartan skirt, white blouse, matching tie, knee socks, the whole works. She even had a little red beret. Her hair was in these little pig tails that just barely hung down from each side of her ears. My heart nearly stopped. God, she was so cute! She was the most beautiful girl I'd ever seen up until that moment. The spoon slipped out of my fingers and clattered onto the table. She looked over at me and saw me staring with wide-eyed wonder. She blushed cutely and looked away, stepping up to get in line behind this enormously fat woman.
She glanced my way again and I made a motion for her to back away from the fat lady a bit, implying with a grimace that a creature that size might be dangerous if anybody got in between her and her ice cream. The girl, who I would later come to know as Casey Angela Simmons, suppressed a giggle.
She ordered her ice cream treat, and then scanned around for an empty table. The fat lady had taken the very last booth just before she'd gotten her order. I gallantly got up and offered her my table, since I was done anyway. Idiot! Why hadn't I thought to just stay and sit with her? I was so nervous, though!
"Are you sure?" she asked in the most beautiful voice I've ever heard.
"Sure! I was, um, just leaving. I'm here every Wednesday, anyway. It's no big deal."
"Every Wednesday?" she asked, sliding into the seat as I got up from the opposite side of the booth.
"Yeah. They have a, uh ... special ... on, um, milkshakes." I wiggled my nearly-empty cup at her. She smiled.
I was trying so hard not to look at her boobs. They were so gorgeous. But her eyes were gorgeous, too. I could barely speak, I was so overwhelmed. I just stood there awkwardly, like an idiot, wanting to flee in terror, but never wanting to not be near her ever again. It was sort of love at first sight, I guess.
She told her friend in the treehouse how cute I was as she described the scene to her, how I was just stammering and babbling. She also told her friend how amazingly hot I was, and how she'd almost died right there just staring into my eyes. That was nice.
"Ever looked into a boy's eyes and just wished you could put the universe on pause so you could lay down and spread for him right there on the spot?"
Her friend gasped, adding a little bit of a sigh, a squeal, and a giggle all at the same time.
"Well, that's how I felt about Jeffery Taurling the very first day I met him. Oh my God! You'll just die when you meet him!"
Anyway, I'd left the ice cream place and walked home in agony and terror, wanting to run back and get her phone number, or even just sit and talk to her for a while. It was too overwhelming, though. She was so beautiful I could barely speak. I was afraid I'd make myself look like a fool. So I walked all the way home and just laid on my bed, thinking about her. Apparently the opportunity was gone forever, though. Or so I'd thought.
Next Wednesday, she was back again. She told her friend she'd planned it all week, knowing I'd be there, hoping I wasn't exaggerating. I grinned to myself. Sure enough, there I was, sipping my milkshake and reading some stupid flyer somebody had left on the bench. Something about sin and hell and dying without Jesus. In walks the little red-headed angel again. No fat lady this time, though. The place was nearly empty, in fact. So imagine my surprise when she strolled right up with her ice cream sundae and sat across from me in the booth. My heart nearly seized right up on me. I couldn't even speak for like two minutes, other than an awkward, "Hi ... back again?"
"Yup!" she said. "This seat taken?"
I just shook my head and fell into awed silence.
Boy could she talk! She babbled on like she would suffocate if she didn't belt out at least a hundred words a minute. She talked like she was addicted to it. Well, I didn't mind. I was soon addicted to her. She told me her name. I told her mine. She asked about my school I asked about hers. We exchanged ages. I'm exactly four months older than her. I was born in April, she was born in August, both on the 18th. She clapped her hands with glee, declaring our meeting must be fate.
"What are the odds we're both born on the 18th!?" she exclaimed in amazement.
"One in thirty," I muttered. I wasn't even being a smart-ass. We'd actually taken a course in probability in math class just a few days before that, and that was one of the questions on the quiz.
"You're cute," she said, taking a spoonful of her ice cream.
It was a very delightful conversation, though mostly one-sided. But like I said, I didn't mind at all. I was happy to just have an excuse to stare into her eyes. I was completely in love by the end of that second Wednesday. And when it was time to go, I asked for her number. She said she couldn't give me her number. She wasn't allowed to talk to boys. My heart nearly died on me, but I tried to remain cool.
"Okay. So now what?" I asked.
"See you next Wednesday?" she said.
And so it became a thing. We met there every Wednesday for the next month. Finally we made other plans, plans to see movies together, plans to walk in the park, plans to go bike riding. She was always sneaking around, though, telling her mom she was meeting a girlfriend, or just going to study at the library or whatever.
Eventually, I asked her to be my girlfriend, on a sunny hilltop near the library. It was just a few days before her birthday. I gave her a little stuffed bunny and just went ahead and asked her. She was stunned. She was elated. She was horrified, all at the same time. She almost looked like she would cry.
"I really think you're the most beautiful guy I've ever met, and I'd love to, but..."
"But?" I asked, frowning, nearly panicked. I think I might have thrown up if she said no. It had taken me a whole month to work up the courage to ask her.
"But, my parents. Nobody knows I've been seeing you. Not a soul. We'd only ever be sneaking around forever. That's not much of a girlfriend to have. And you could have any girl you-"
"You think I haven't thought about that?" I told her. "I know we'd be sneaking around, but even scraps of light from an angel is better than living in darkness forever."
She really did cry right then. A tear spilled out of her eye and trickled down her cheek. "You're so sweet to me. I'd be a fool to say no."
"So, that's a yes ... then?" I asked, anxiously.
"Yes! Of course, stupid!"
And so it was decided. We didn't even seal it with a kiss, though. She just smiled so brightly I thought I would go blind from it, and then reached out and hugged me tightly to her soft warm body. It was the most beautiful moment of my life so far. Even the smell of her hair made my brain tingle.
It was after that she told me about her treehouse. I told her I'd climb the wall and meet her there, like Romeo and Juliet. She didn't think I could do it, but I scrambled up that wall like a champion athlete that first night and haven't failed once since then.
That's where we first kissed. And I was lost forever, completely and totally gone in love. I didn't eat for a week after that night.
She told her friend in the treehouse a lot more about it than that, mostly girly details about how great a kisser I am and stuff like that, and how she'd let me grab a boob eventually. I grinned to myself. All she ever told me in person was how dumb I am. But apparently, she was really over the moon for me. Her friend sighed, confessing herself to be dying of envy.
It was at this point, I leaned over and peeked in the back window, just a little. It was dark in the rear foliage behind the treehouse. They didn't see me, but I saw them. Her friend was facing the front, but sort of turned toward Casey, who was half turned away from me as well. Neither of them saw my one eye peering over the sill like a ninja in the dark. Casey apparently just assumed I'd left the moment I climbed through the window.
Her friend really was hot. Her face was pretty from what I could see, but it was her lips that I noticed in that dim lantern light. They looked like a kiss from them would make you faint, so soft, round, and puffy. I couldn't believe she didn't have a boyfriend.
Her hair was long, all the way down to the floor the way she was sitting, in two rope-like ponytails. She was blond, too. She had a nice round bottom. But her boobs. Oh my God, her boobs were absolutely epic. I could hold one of them in both hands and there would still be room left over. It was insane! They were high and pert, and protruding proudly, like monuments to female beauty. She was wearing a loose-fitting T-shirt, but it didn't really hide much. Her boobs were as obvious as the full moon on a clear summer night. Two full moons, actually. That would be really conspicuous! And as she'd said, her nipples were stiff little points, poking through the cotton of both her bra and t-shirt. I nearly whistled in appreciation. I didn't, of course. I'm not that stupid. Instead, I crept back into the shadows and just took a deep breath, calming myself.
Tammi
- 07.04.2022
- 21
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