Masturbation Archives — Page 391 of 468 — NSFW story

Teacher, Teacher [mF] [oral] [mast]

Allen was always shy. Even today, at 30, he’s awkward, which is a shame because he’s so damn good looking. Sometimes, a woman will smile at him and he’ll smile quickly before looking (or running) away.

In the 5th grade, his teacher left mid-year for maternity leave. In her place, a fresh out of college 21 year old named Maggie Hart. Maggie was a stunner. Bright red hair, freckles, a smile to kill for. All he knew was she made him smile. Allen loved Ms. Maggie Hart.

At the end of the year, Maggie Hart moved. He never saw her again.

20 years later, Allen found himself working in Chicago. He went to a bar with some friends for trivia. Most teams were too far behind, but there was one team that was tied to Allen’s and the woman leading the charge was as smart as all hell.

The only time Allen felt confident enough to talk to another woman was when she was on his intellectual level. If he could only see this woman, he’d try to make eye contact with her. But she had her back towards him. Read more »

Aunt Jane comes to Town [mF] [oral] [anal] [creampie] [inc] [mast] [huml]

When Charlie was 16, he spend the night at his uncle’s house for a weekend. He was close to his uncle, but he was really close to his Aunt Jane — she married into the family. Aunt Jane was hysterically funny, a fantastic cook, and had a sort of Rose McGowan look to her (before the surgery).

It happened that Charlie was visiting at a bad time. First of all, Aunt Jane and Charlie’s uncle were going through a divorce. She had moved into the guest room. And second, Aunt Jane wasn’t even there.

Aunt Jane called and asked to speak to her favorite nephew.

“Listen, kid,” she said. “I know there’s another guest room in the house, but I’ve moved into the better guest room. Since I’m away, why don’t you sleep in my bed? It’s more comfortable and the pillows are better. Feel free to use a drawer if you need it.”

That night, he went snooping, as most 16 year olds do, through her stuff. Her panties. Her bra. And then, he opened the nightstand drawer next to the bed and his eyes nearly fell out of his skull. Read more »

Live Sex Birthday! [mmmmmmmmmmf] [huml] [drugs] [buk] [mast] [oral] [reluc]

Lucy had a wild group of friends. They were always doing something raunchy, whether it was her friend Becky sending her a Snapchat of her shopping for dildos or her friend Scott sending her a Snap of him on the toilet, taking a shit.

She’d laugh, roll her eyes and continue on with her day.

But as her 25th birthday approached, she told her boyfriend Joe that she wanted to do something different. Something bold for her little group of friends.

“What do you have in mind?” He asked.

“I donno, you come up with something. I’m down for whatever, so long as it’s tasty, shocking, and is a dick.”

Lucy hoped Joe got her message for a penis shaped birthday cake.

The problem was Joe, who had “married in” to her group of friends, had a different idea. Something that would definitely shock this rowdy group.

They held the birthday party in Lucy’s backyard and her friends all showed up at sunset. They ordered pizza, everyone brought drinks. Some folks were smoking pot. Nothing unusual. Some friends even took to “The Triple X Room” to fuck. Read more »

The Wives Make a Bet (MFF, public, sister-in-law)

My wife and her sister were arguing again, this time about some no-name actor that played in some long-ago watched movie, and whether he was dead or still alive. At 26, my wife Cindi was in her prime and was looking smoking hot that night and Heather, her sister at two years her junior, was almost as attractive. Both were tall and skinny, but Cindi had bigger boobs and brown hair while Heather was blonde with small perky tits. It was a Friday night and we were at the house that Heather and her husband Brian had just bought having dinner together, something that we tried to do once or twice a month.

“I know he’s dead, I remember reading about it in People”, Cindi insisted! She was absolutely certain that she was right and was not going to back down. Knowing my wife, I suspected that she may have been wrong, but I wasn’t going to tell her that. Brian and I were content just watching the exchange, since it involved two very beautiful women.

“Still alive, he just did a part in Law and Order, I remember!” Heather shot back. “I am so confident that I’m right, I’m willing to bet on it.” And she stuck out her hand. Read more »

Mom saved the day [mff] [inc] [twins] [oral] [mast] [cum]

Anna and Sally—twins—were home for the holidays on their winter break from college. They’d both just turned 21 and were in their childhood room having a heated argument.

Their mother, hearing the commotion from downstairs, went up to intervene and try to help the girls cool down. But before she did, she snooped, like she always had, right outside their bedroom door to get the truth before they could try and lie.

They were arguing about a boy.

“Enough,” their mother said as she knocked on their door and entered. “What is going ON in here? It’s the holidays! Can’t we all just get along?”

“It’s nothing,” Anna said.

“You would say that,” Sally said.

“What is going on? Tell me everything and maybe I’ll have a way to resolve this fight,” their mother said.

“It’s Tom,” Sally said.

“Tom the boy from high school?”

“He’s back for Christmas, too, and we just saw him at a bar,” Sally said.

“And I like him and Sally is trying to steal him away from me,” Anna snapped.

“I liked him first!” Sally shouted. Read more »

Who said Long Distance can’t be [f]ulfilling? It’s just got to be done fucking right. All in with all you got! [M]

I feel this story deserves to be r/gonewildstories worthy as any other story posted here even though it’s a bit different than the standard fair of what is posted. It was hands down one of the most amazing intense hottest encounters I have experienced and what makes it all the fucking more crazy she was the opposite side of the world to me and I feel we broke reality and all fucking logic itself in one particular online encounter.

I am just not sure readers of this story will find it as hot as I feel it was, but I will try my best to give the story the justice it deserves.

A bit of back story. I am a tall, I like to think friendly, somewhat decent, reasonably ok looking guy in his early 30’s. I had been single a while, feeling all unlucky in love and unwanted. I had tried dating apps to not much joy. Read more »

A little [F]act and a little fiction [Fdom][cuck]

Venus I

Venus knew what she was going to find behind the door. It was the same sight she’d uncovered so many times that she – and almost all of her friends – had come to call it by name; The Disappointment.
The Disappointment was 6’3” of wasted potential that had once provided both sexually and financially, but that now laid around smoking too much weed and watching too much porn.

The Disappointment was the owner of an 8 inch dick that lately seemed to struggle to raise above half mast without an exhausting – and usually depraved – effort from Venus to get it there.
Even when she did succeed, the stoned barely fuckable dick was usually connected to an increasingly useless stoned layabout.
Venus had had enough. She ran her thumb over the small steel arch in her pocket. Her index finger toyed with the small opening in the plastic. She pushed the last trace of doubt out of her mind and cracked open the door.

Sure enough, there it was. A flaccid cock hanging over the top of the pink lace panties her pathetic excuse for a mate wore daily, a pool of cum on his stomach and – oh. He’s been watching that. She slammed his laptop closed. Now she was definitely sure she was doing the right thing. Read more »

Jessica was used to getting her way [humiliation][nc][preg][Mf] (part 2)

A little more than a month later Paolo still hadn’t called. Jessica doubted he ever would. She didn’t blame him. She lay there in bed, running through that night again. She flipped on a vibrator, held it between her legs, and let the memory of guilt and pain and pleasure drive her. A few minutes after she came, her stomach turned. She ran to the bathroom. *Uh oh. No way! I’m on birth control.* She cleaned up and called to make an appointment with a gynecologist who she knew performed abortions. Later that day, she bought a home test at CVS. When she took it, it came up positive. Of course. Goddamnit all to hell!

Dr. Brooks, was in his mid fifties. Salt and pepper hair. He had an air of practiced competence that gave him command of the room as soon as he entered it. He was handsome. Jessica sat in the gown the nurse had given her, her head spinning with nerves. He flipped the top sheet on his clipboard. “Jessica Seale, right? You had a home pregnancy test come up, positive?”

“Yes. But I’m on birth control!”

“Okay, that can happen. Were you on antibiotics at the time perhaps?” Read more »

Cabin in the Woods [MF] [oral] [mast] [swallow]

It had been a rough week, so I went online and found a mountain town about an hour and a half away where I could go, by myself, to unwind. Jessica, the AirBNB owner of a small cabin, said she’d meet me when I arrived Wednesday night to give me a brief tour.

“What brings you to the mountains?” She asked.

Jessica was a tall brunette with a nice body. Great, long legs, a few tattoos on her forearms and a sultry smile.

“My girlfriend and I broke up a few weeks ago and this is the first time I feel well enough to do something for me,” I said. “And this is what I want to do.”

“Aw, buddy,” she said, caressing my arm. “I’m sorry to hear things haven’t been going well. But the mountain air’ll be good for you. You know what? I’m gonna get the hot tub going for you. It’s a little crisp outside, but it’ll feel damn good.”

I thanked her and took my suitcase into my bedroom. I sighed. Jessica was beautiful and I’d probably use a mental photo of her to jerk off to later that evening. Read more »