HIGH SCHOOL TEACHER, PT 2 [anal] [mast] [cheat]

The tickets were booked. My high school teacher’s husband was taking the kids to see the grandparents for a very long four day weekend. She messaged me to say she had “begged him” to let her stay home for some much needed R&R. A little “stay-cation,” which he supported, only because he knew his parents would do most of the work involving the kids.

“So excited to see you!” She said.

Her name was Mallory (or Ms. Jacobsen) and even though she was quickly approaching 50, she looked as youthful as I remembered in her high school classes, when I would get erections under my desk as she walked around the classroom giving her lectures.

“I want you to cum inside of my asshole,” she texted. “I feel like a 20 year old again. I swear. I am SO excited. I need some ass play. I need it so bad! I swear!”

I would respond by sending her dick pics, which she frequently requested.

“Do you like to deep throat?” I asked.

“Are you kidding? Wait. Hold on,” she said in response.

HIGH SCHOOL TEACHER, PT. 1 [MAST, CHEAT]

I posted a photo of some food. That’s how it all started. An old high school teacher commented saying how delicious the food looked. So, I DM’d her to share a few more food pics. She joked that she was stuck at home with two young kids and that I was making her jealous.

“What can I do to make you less jealous?” I asked.

“Hmmm,” she said. “Post less pics?”

“Hah ok,” I said.

A lengthy catch up unfolded. What are you up to? Where are you living these days? She said I looked like I’d turned into quite the handsome man. I confessed that I’d always had a crush on her as a teacher. She said she was the older teacher now, at a different school, halfway across the country. And she didn’t feel like the sexy young teacher anymore. I told her she was still gorgeous, and I was sure as many kids were hot for her today as they were in my class.

She said it was nice to catch up, but, speaking of kids … she had to pick the older one up from school.

IT STARTED OFF FACETIMING [mf] [mast] [squirt]

A month. And then a few months. And before they knew it, it had been a year. And then, somehow, almost two since the divorce. They remained sort of friendly. But she was always eager to get back together. And all he was eager for was to fuck her one last time. He would jokingly bemoan the fact that they never had “break up sex.”

She would say, “Your loss.”

They would flirt … or argue … or both. And then they’d both throw their phones down in a fit of rage or annoyance. Or both.

He fell into bachelorhood with ease, downloading all the dating apps straight away. “Recently divorced,” his bio read. “Looking for carefree fun.” He spoke with his female friends, who all shared the same dating app complaints: Topless gym mirror selfies were a turn off. So were photos by luxury cars. And anyone who launched immediately into sex was disqualified. His profile landed him tons of matches and he fucked his way out of his divorce slump and into his “man whore phase,” as he called it.

SHE JUST WANTED TO SWALLOW [mf] [mast] [swallow]

Annie sat on her couch watching some stupid reality show. A glass of white wine sat on the coffee table. She was wearing a see through tank top and big comfy pants. The window was open. It was a little chilly outside. Her nipples hardened. Noticing her erect nipples, Annie nibbled on her bottom lip. She looked outside and into the apartments across from the alley. Sometimes, she could see her neighbors and they could see her. Tonight, there were no lights on. No neighbors standing in windows. She shifted, excitedly, and slid her hand down her pants, masturbating.

She brought herself to orgasm. Twice. And then, she licked her fingers clean. But she wanted more. She was hungry. Annie loved to swallow. In fact, she loved swallowing cum more than she loved anything else—sucking, fucking, foreplay, sexting. A big load in her mouth was her favorite.

She grabbed her phone and scrolled through her texts, looking for a guy she knew. A guy she trusted and liked. A guy to come over … not to fuck, not to suck, not to make out with or giggle with or snuggle with … she wanted one thing. A load. And then, a name jumped out to her. A guy she’d gone on a date with a few times months ago. They got along, but the sparks just weren’t there. Nothing to lose, she figured.

GANG BANG ON THE BUCKET LIST [mmmmmmmmmmmmf] [gangbang] [bukkake]

I’ve been taking a yoga class at my gym recently. The teacher is a smoking hot, blonde from Sweden — muscular, but not in a disgusting sort of way. She’s still got perky tits and a great ass that jiggles when she walks. I started taking Inna’s class because I wanted to strengthen my core. But a few other guys take the class just because they enjoy watching Inna get on her hands and knees to do cat/cows.

After class, once we all retreat to the locker room, we often discuss how sexy Inna is and how good she must look naked. One of the guys then turned to me and said, “Hey, you should ask her out!” They all joined in, egging me on to ask her out. And so, I did.

The following week, after class, everyone poured out of the studio, except me. I lingered, pretending to check something on my phone.

“Hey, thanks for coming!” Inna said, as she grabbed her stuff and headed for the door.

“Any time. I think you’re great,” I said.

“Thanks!”

“Hey,” I said, as I held the door open for her. “Would you wanna get coffee or lunch one day after class?”

PUKE AND PISS SLUT [mf] [facefuck] [facial]

Joseph and Sally had known each other since first grade. They’d remained friends into early adulthood, during Sally’s extremely slutty phase. The sexual tension between the two of them was insane, but they never fooled around. Sally viewed him as her protector, often texting him the name and address of her latest one night stand, just incase.

In the morning, she would text him every. Single. Detail. She knew he was masturbating to her texts—not because he told her, but because how could he not? And secretly, she liked the attention. And so she left out nothing.

He wanted her so badly. And she wanted him, too. But they both knew it would potentially fuck with the friendship, and so even though they teased sleeping together … they never did.

Eventually, Sally found herself in a long term relationship. Their friendship morphed from flirty to genuinely friendly. And, as most things often do, her relationship came to an end. After a prolonged funk, she rediscovered her slutty side, one time even saying, “I don’t think I’m built for long term dating. My happy place is a different bed every night.”

CAMPING SLUT [mmmmf]

This is a cut and paste from my friend Mary, from a text message convo we had a few nights ago when we were up late, texting about sex. I had asked her what her sluttiest moment was. This is her response:

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Categorized as sexystories

BUTT FUCKED INTO OBLIVION [mf] [anal] [squirt] [creampie] [facial] [swallow]

Jacob met Kayla on Tinder. They went on a date, didn’t really hit it off, and that was that. He figured he’d never hear from her again. And he was wrong. Because that evening, Kayla texted him around 11pm.

“You up?”

“Sure am,” he wrote back.

“Wanna come over?”

“Sure do,” he said, chuckling to himself. How could this have been? A terrible date, a woman he never thought he’d see again. And suddenly, she’s calling him over to fuck? Well. Perhaps it’s because she figured there was nothing left to lose. Might as well get laid.

Jacob jumped in his car and drove to her apartment and headed in. She met him in the lobby wearing booty shorts and a see through tank.

“Hey,” he said, giving her a quick hug.

“Hey back,” she said casually as they got in the elevator. “So …”

“So …” he said.

“I have a request,” she said quietly.

“Oh? What’s up?”

“Give me your hand,” she said.

She took his hand in hers and turned around, guiding his hand into the back of her shorts. He put his hand on her ass cheek.

CHEATING ON THE MOTHER WITH HER DAUGHTER [MF] [Mf] [oral] [mast] [squirt] [creampie] [swallow] [anal] [cheat]

Connor was in that once in a lifetime sweet spot. He was 32 years old, which meant he was both old enough to date cougars, and young enough to date 20-somethings without being creepy. He wasn’t much interested in fellow 30-something year olds — they were on the marriage and baby track, something he wanted nothing of.

That’s when he met Marissa, a 51 year old woman who looked like she was closer to her 30s. Marissa was insatiable after a recent divorce. All she wanted to do was fuck. Connor and Marissa spent tons of time together. They went on road trips. They went on hikes. She wanted to fuck in every position, and in every location possible. Changing room. Starbucks bathroom. On the side of the road. In the woods behind a boulder while other hikers passed by.

She craved cum. She swallowed it as often as possible. And since she was a little older, the risk of pregnancy was no longer an issue. So condoms became a thing of the past. Connor fucked her as often as possible, relishing in the beauty of the creampie. He loved cumming in her. He loved watching his load drip out of her cunt in the woods while they giggled as others walked past, having no idea what was happening on the other side of that boulder.

SHE WALKED IN [mf] [oral] [creampie] [swallow] [grool]

He was sitting on the sofa in the middle of some stupid TV show—not really even paying attention. And then, she walked in. She was completely nude. He sat up and smirked. She smirked back at him as she walked into the kitchen. She was thick—curves in all the right places—and at his request, had grown out her bush. She walked into the kitchen, opened the fridge, filled up a glass of water, and began to drink it. She knew he was watching. He loved her ass. Absolutely. 100%. Loved it. If you’ve ever been to /r/slightcellulite, you know what her ass looked like. A slight jiggle when slapped.

She walked back towards the living room. His pajama pants did a lousy job covering his massive erection. She licked her lips as she watched his cock throb. Her nipples were rock hard. She had big, perfect tits. She chewed her inner lip as she studied him.