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I woke to the gentle sound of Linda's breathing a few inches from me in my parents' king-sized bed. My nakedness against the sheets heightened my awareness of my stiff dick underneath my body. I could feel her warmth radiating across the short distance between us. I'd never awakened next to a girl before. Katherine and I went down on each other in the basement, then usually just went back out to play. Waking up next to Linda after sex was a completely new and exciting experience.

She was faced the other direction, her red locks flowing wildly in a river of bed head flowing towards my face. Her bare shoulders were visible where the covers stopped covering her. I felt a surge in my cock and shifted, feeling the softness of the high thread count sheets caress the head of it pleasurably. I raised up off the pillow slightly to spy one pink nipple, exposed just above the sheet line atop the small mound of her boob.

Squinting through the shadows I saw the clock by the bed read 3:43 AM. I'd only slept a few hours since our first fuck earlier that night when I slipped in bed next to her and talked her into it. She was our house sitter for the week and I don't know why I thought she'd be open to it, but made the move and it paid off. How many guys my age could say they boned a 19 year old? It was hot as fuck. But, bragging rights were not on my mind now so much as were the curves and softness of her nude body next to me and, ringing in my ears, her warning that she would want another round before morning if I was to stay in bed with her. My hard-on was already aching for it.

I had no idea how to approach an older girl while sleeping. So, I just spooned up against her. My dick fit neatly in the crack of her butt, warming my rod and giving me the urge to hump against her. She moved a little, her breathing uneven, but did not speak. My hand slipped around her waist and felt her tummy, then climbed up, feeling ribs and soft skin until the roundness of her breast followed up to the nipple I could see. I fingered it deftly, noting it's shape and how it rose to hardness in the low light, inches from my face. I had to remind myself to breathe.

Her eyes popped open, then closed. She stretched suddenly, reminding me of my little sister in a rather adorable way, her arms straight and taught above her head until collapsing back on the sheets. Some girlish things even a 19 year old hasn't outgrown, maybe. In that moment she felt less like an "older girl" and more like just a girl. It helped me feel less intimidated. Her head turned part way my direction, then back to her original position.

"You can touch me anywhere you want to," she said sleepily.

"Fucking awesome!" I thought. I let my fingers glide up and down her rips, exploring the details. She rolled slightly to allow me to touch her other breast, sighing without opening her eyes when I fingered her nipple, watching it change shape.

"Between my legs," she said, guiding me around her body. I reached down between us, slipping my hand awkwardly between her butt and my penis. "In the front," she added. Oh, ok. I reached around her waist, my fingers finding the furry patch of orange above her labia and sliding through the rich bush to find the top of her clit. "Mmm-hmmm right there," she said contentedly. "Put your finger down in until you find wetness, then spread it over the top."

I loved how chill she was as she coached me through touching her. I always felt with Katherine that I had to figure it out on my own. And, she only told me when I did something she didn't like, never how to please her. Did she tell Scott this too, or do the older guys just know? I felt a sting of competition with him.

Down into her I went, my finger slipping between warm, dry lips and finding a little friction there. The image of her fleshy petals and the pink moist place between them flashed in my mind from earlier when I'd been down on her. I had to push kinda hard, but she lifted her thigh slightly to let me in farther. The opening gave way through resistance to a runny, slippery place that seemed to welcome my probing finger. I made a hook shape, wiggled a bit and pulled back out, a fingerful of her lube slipping behind it like a snail trail. I smoothed it over the gathering of skin at the top of her vagina. She let out a sigh.

"Yess, just like that. Now, massage me there. That's how I diddle myself when I wake up. Just, a nice, slow clit massage."

I settled into a comfortable position, resting against her from behind, my stiffy in her butt crack like a sheath as I reached around front and made little up and down motions on the outer skin of her clit. This one Katherine taught me well. She wanted it on the outside so the two halves could rub together on the inside. Linda laid still and enjoyed while I gently masturbated her.

"How often do you um...diddle?" I asked, feeling self-conscious half way through the question.

"Every day," she answered effortlessly. Then one slit of an eye looked askance towards me. "Don't you?"

"Um, yeah," I answered sheepishly. "What do you think about?" I asked, curious about her sexual life.

"Shhhh," she said. "Sex now, talk later." I was overtalking. Her vagina was becoming more responsive as the skin seemed to melt under my caress. Being up against her from head to toe, I could feel all the little reactions her body made to being touched. At first, they were minimal, just small muscle contractions every now and then. Then small shudders. Her pussy produced more lube, a fresh trickle every few minutes flowing out of her until my fingers made small gurgling sounds. Up from deep within her came moans that sounded like pleading. Her body was telling me not to stop. Her face went from a relaxed enjoyment to more and more furrowed brow and agape mouth. It was super erotic to watch her expression take on more and more o-face.

"Oh god, that's just right, right there, ohhhhh..." she continued. Perspiration appeared on her back and butt cheeks as an orgasm swelled in her.

"I want you inside me," she said. He hand reached round and she pouted her ass back towards me. Just past her anus was all slippery and my rock hard dick slid easily up into the hole. She was almost hot inside. I felt myself with my wet fingers as I began to propel in and out of her. I had to work with the position to find the leverage to drive in deep enough. She pulled at me and turned her face towards me, an orgasmic expression twisting eyebrows together and bearing her teeth.

"Fukkk..." she whispered as I began to pound into her, making the bed squeak rhythmical.

"In my ass for a minute," she said to my surprise. Her hands came back and pulled her butt cheeks apart. She lifted one leg up into the air and rolled over on her front. I had to get up on my knees. I could see her bearing down, making her asshole pucker out towards me. She was already glistening with slippery wetness all over her hole. I easily pushed my cock into it. She groaned as I drove past her sphincter and into the warm cavity of her colon. Her muscles contracted and pinched against the length of my shaft as I eased inside her. Then back out, then bringing my rhythm back up faster. She felt different inside her ass, tighter at the opening, looser inside. Linda's pretty face was pushed half down into the pillow as she moaned again, taking the pounding of my penis into her butt as she feverishly fingered herself. It was unbelievable.

Then, she quickly flipped over, grabbed my dick and I was back inside her. She rolled on top of me and fucked me like a jackrabbit, her hot mouth covering mine with rapid breath and the loose wetness of her tongue. We were a ball of sweat and hair as we rose quickly towards sexual crescendo.

"I'm cumming, I'm cumming, I'mmm...oooaaahhhhhhhggggg..." her face was down in my neck as she began to quiver uncontrollably on top of me. The spasms drove me to the peak and I began to inject her with my sperm. Pulse after pulse shot into her as she came on top of me. Her hands clasped at my shoulders as her hips pumped repeatedly up and down against my pelvis. Spasmodically our bodies banged together as I came up into her. Her boobs bounced frantically until her head flipped up, eyes closed and mouth open while the last of the orgasm spent it's sexual urgency through her. My cum continued to spurt inside her, leaking out thickly onto my pubic hair. She finally relaxed a bit, taking a deep breath and squeezing her thighs slightly before coning to rest on top of me, my cock still inserted into her.

She braced herself, panting with face away from me for a few seconds. Then faced me and I felt her lips melt into mine, her tongue coming into my mouth hot and thick. We made out for what seemed like 10 minutes, wound in a ball on the bed until my soft penis slipped out of her and she rolled down onto the bed next to me. Questions about what this meant with her boyfriend Scott floashed through my mind. But, I just relished in the hedonsitic glory of making love to sexy Linda in my parents' bedroom.

"Holy fuck, fucking hell..." she said. "First time was not a fluke. What the fuck?"

"What do you mean?"

"You're way too young to be this good in bed. We must be weirdly compatible or some funky shit, I don't know."

"So are we at 'tell your boyfriend to fuck off' good yet?"

At this she laughed. "You really think a lot of yourself don't you?"

"Too much?"

She eyed me. "Scott is my boyfriend and you can't be my boyfriend for another five years. So this..." she made a gesture between our bodies. "This has to be a secret from ABSOLUTELY everyone, and I mean ev-er-y-body."

"And if it stays secret we can fuck?"

She shook her head like I'd bested her. "We have the rest of this week to find that out. But don't get full of yourself, grasshopper."

"Ok, Kung Fu." I looked away and donned my best David Carradine voice. "When the heart knows no danger, no danger exists."

"Gawd, shut up and kiss me," she said as her mouth enclosed over mine. I felt her body press into me, her legs entangling with mine as her still-wet pelvis pushed into my thigh. We embraced and kissed until my lips and cheeks tingled from the pressure and I'd tasted every square inch of her neck, face, and ears. finally, she laid her head against my shoulder and dozed off.

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We had planned this night out for some time, but as usual something always goes wrong. The baby sitter called & cancelled at the last minute. I suggested that my wife ask if Shelly, the 17 year old girl from next door could baby sit at short notice. She trotted off next door & came back to tell me that Shelly was not available but her 19 year old brother Joey Was. We really wanted to go out so she agreed to let him sit for us. He seemed like a fine young lad, he was very fit, he was a...

2 years ago
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The Sitter

The Sitter by Erin Tyler In December of 2450, I took a big chance and left the disquieting confines of The Mistress' junk-lab, the only home I knew. I found myself in a ruined city, surrounded by the hostile natives of the land that had once been United States of America. The nation that had put a man on the moon was defunct, and its descendants led short, bitter, hand-to-mouth lives. In January of 2451, I learned the defunding of all public education and research caused this...

4 years ago
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Wife Hires Baby Sitter

My wife and I had been going through a long dry spell while she was pregnant to a few months after she had the baby. We would have sex occasionally during her pregnancy, but toward the end she said it was getting uncomfortable. The doctor had ordered no sex for at least six weeks after the baby was born. We tried having sex once after the six weeks was up, but again she said it was still a little painful. So the only action I was getting was watching porn late at night, and masturbating. I was...

Taboo
3 years ago
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Black Sissy Sitter

BLACK SISSY SITTER by Throne Jack was in a state of confusion. His girlfriend Tiffany, a willowy blond beauty, had invited him to meet at an unfamiliar address. It was an inner city neighborhood. He had been uneasy driving there, parking his car under a streetlamp, and walking the half block to the door. When he knocked he got a devastating shock. She was there but had drastically changed her look. Instead of the flowing hair he loved so much, she had cornrows that clung to her...

4 years ago
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Seductive Sitter

Jill was the sitter my wife and I had settled on, because she had experience working in a day care and was an early childhood major at the college where I taught. Of course, I would have hired her on looks alone; the chance to see her made Wednesdays when she sat for us wonderful. She was tall and slender, with youthful modest breasts and gentle curves. But she had long, full, lush red hair that perfectly offset her creamy, freckled complexion. And she had a way of moving, deliberate and...

Quickie Sex
3 years ago
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Emergency Sitter

I’d known Kristen for almost two years. Our nine year-old sons played soccer on the same team, so we spent many Saturday mornings alongside the field watching them run around after a white ball. We weren’t exactly “good friends”, but we talked every time we met, passed the time of day and consoled each other in our single parent status. My wife had left me for her rich boss and how her husband ran off with a girl from a trailer park. We always laughed about how there was a message in there,...

Straight Sex
2 years ago
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Anns sitter

Ann complained while her mother was on the phone, I don't need a sitter she argued. Her mother said, I don't care, you're not staying by yourself, and that's final.Hanging up the phone her mother told her to take her bath.While Ann was bathing she got ready for her date.Finishing her bath Ann put on her nightgown and clean panties.Coming out front, her mother was talking to Mary. She explained how she was. Mary smiled and sad no problem.Mary asked Ann what she liked doing. Movie and video...

3 years ago
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Maggies Secrets Secret

Maggie's Secret's Secret This story is purely fiction. No corporations or names represent real people or companies in any way. I appreciate all story reviews to help me become a better writer or, from a purely selfish perspective, make me want to continue writing. If you like the story I've written numerous others that you might want to read. You can search for all my stories by using the 'author search' and typing in the author, 'Want2BaGirl'. I hope you enjoy. Part One -...

3 years ago
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Sorority Sister Sissy Sitters

SORORITY SISTER SISSY SITTERS by Throne Kevin was very uneasy. He knew his wife Petra was going out for the evening and she had hinted at making some special arrangement to deal with him. What else could she do? After discovering his habit of dressing girly when she wasn't around, she had used it against him. Whenever he was home now he had to wear the most shameful outfits she could think of. For instance, at the moment, he had on a sleeveless gingham top, the halves of which tied...

2 years ago
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Seduction Of Gorgeous Indian Mami Met During Housewarming Function 8211 Pt 1

Hi all Indian hot story readers, this is Madhan here. First of all, thanks a lot to all ISS readers for your many likes and valuable feedback for my previous story. Please share your views and corrections if any. About me: I am a Madhan, 27 years old, 6 ft tall, south Indian complexion, broad shoulders and a well-built body. I basically belong to one of the cleanest city in India – Mysuru. But I am currently working in Bangalore (which has all varieties of chicks and aunties). Guys, this is...

3 years ago
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The House Sitter

Stepping up to the closed door, I raised my fist and gave the hard wood three sharp raps, hoping the brisk knock was adequate to be heard above the blaring music. A few seconds passed before I raised my hand again to repeat my knock, when the door swung open. Before me stood Laura, smiling enthusiastically as she held a glass of wine in one hand as her other moved from the doorknob to rest on her hip in a blatant attempt to strike a provocative pose. "Hellooooo," she beamed, flashing...

1 year ago
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The House Sitter

I could hear the faint sound of music emanating from behind the door as I made my way down the hallway.   Each step brought me closer as the music became louder and louder.   I listened intently as I closed in, but could not make out place the song or the band, writing it off as one of the many independent, no-name artists that Laura always listened to.   Stepping up to the closed door, I raised my fist and gave the hard wood three sharp raps, hoping the brisk knock was adequate to be heard...

2 years ago
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A show for an 18 yo teenage baby sitter

True story that happened about 10 years ago.... I copied this story from where I wrote it originally. I was responding to a story written by eekntake where she did something very similar that reminded me of this story. So if you see it twice, know it is me in both cases, if you don't believe me then take a look at the username in the comments field. Now on with the story:I had worked late a few years back, like almost all night. It was summer and the k**s were off from school. So when I got...

1 year ago
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The Baby Sitter

Alissa had been baby sitting for the Bentley's for about a year. She was a senior in college, and baby sat to earn spending money. Alissa was a pretty 23 year old, with sexy blue eyes and short blonde hair. Mrs. Bentley, and her husband Tom had called Alissa to babysit for them Saturday night, and told Alissa she could use the guest bedroom because they probably wouldn't be home till the wee hours of the morning. Around eleven Alissa decided to go to bed. Alissa couldn't get to sleep no matter...

3 years ago
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Housesitter

Last year while Tom and I were living in Myrtle Beach we had a house in a very nice neighborhood with many  good friends.  We lived on a circle at the end of a dead end street which eliminated through traffic and noise.  Directly across from us on the circle is where Jeff and Allison lived.  They were a couple just a few years younger then Tom and I and they had two children.   During the month of June Allison stopped over for morning coffee and asked me for a favor.  Her, Jeff and the kids...

2 years ago
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housesitter

this is a fiction ,,,,,, was late as i rolled into the driveway. looks dark as i make my way into the house. is a little light comeing from the tv in the liveing room as i get closer to it. as i walk in i have to let my eyes get used the the surroundings. there on the couch is my housesitter all alseep curled up on one end, i make my way over the the other end and sit down. i see that it was a porn on the tv as i can see its cover laying on the floor in front of lisa my housesitter. beside...

2 years ago
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Nat and the Housesitter

Nat and the Housesitter (c) 2009-2010 by Trismegistus Shandy This work is licensed under a Creative Commons Attribution- Noncommercial-Share Alike 3.0 United States License. Feel free to repost or mirror it unmodified on any noncommercial site or mailing list. You can also create derivative works, including translations or adaptations to other media, or new stories using the same setting, characters and so forth, as long as you mention and point to the original story and release...

3 years ago
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Housesitter

Last year while Tom and I were living in Myrtle Beach we had a house in a very nice neighborhood with many  good friends.  We lived on a circle at the end of a dead end street which eliminated through traffic and noise.  Directly across from us on the circle is where Jeff and Allison lived.  They were a couple just a few years younger then Tom and I and they had two children. During the month of June Allison stopped over for morning coffee and asked me for a favor.  Her, Jeff and the kids were...

Straight Sex
1 year ago
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FunWithFriends

Reddit FunWithFriends, aka r/FunWithFriends! Is there any sex that’s better than with friends? I’m not talking about the weird sex that ends friendships because the bitch couldn’t compartmentalize and, ‘accept what this was.’ I’m referring to the kind of sex where friends want nothing more than to fuck one another’s brains out, clean up, then go out and grab a beer before going home, taking a giant whiskey dump, then going to sleep. The kind of friend sex where everyone fucks because they want...

Reddit NSFW List
4 years ago
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Housesitting Day 0 Chapter 7 Paiges Dirty Secret edit

HOUSESITTING DAY 0: The Day Before Chapter 7: Paige's Dirty Secret Paige's heart skipped a beat when she heard the pebbles click against her balcony door. It thrilled her every time. It made her feel like she was back in high school again. She felt the butterflies fluttering in her stomach as the familiar anticipation of what was to come sent jolts of sexual energy through her body. Taking a deep breath, she got up from her bed where she had been reading and even though she wanted...

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