Author: soulcrushinganxiety

Step-sister’s Failing Marriage [incest] [M] [F] [cheat] [oral] [mast] [swallow]

Mallory’s mom married my dad when we were in our late teens. By that point in time, we really didn’t care about a step-sibling because we had our own lives, and soon, we’d be off to college. Mallory and I were basically roommates, only saying hey if we walked past each other.

After college, we barely spoke. Maybe I’d like a post of hers on Facebook. If she wasn’t traveling abroad, I’d see her at Thanksgiving or Christmas. She got married, had a kid. I had a girlfriend, didn’t want kids.

I moved to NYC. A year later, Mallory called to say she was coming to NYC for work, but her assistant forgot to book her a hotel room and she was scrambling and —

“Say no more, you can stay with me.”

The next night, Mallory took an Uber from Penn Station to my apartment. We hugged. I hadn’t seen her in years and was stunned by how beautiful she was. I showed her to my room. “I’ll sleep on the sofa,” I said.

“Oh, you don’t have to. I’ll take the sofa. It’s okay. I really don’t mind. Actually, I sleep on the sofa most days, now, so …” Read more »

Pegging with a Lesbian [m] [ff] [threesome] [oral] [cheat] [pegging] [anal] [squirt] [mast] [reluc] [cum]

My girlfriend, Maddie, has a lesbian friend named Uma who comes to town twice a year. I didn’t know Uma used to be into men, but it all made sense now—how she grabbed my arms, told me what big muscles I had, told me she loved the beard.

I texted Uma to ask if I could have anything in the house that she might need. When she said no, I wrote back to say I’d get our guest bed set up so she didn’t have to sleep with us.

“Aw, that’s no fun. You mean Maddie doesn’t want to have a threesome?”

“I wish,” I wrote back.

“Huh, for some reason I always pegged her as the kinky type.”

“Nah,” I responded. “And since you say pegged, I doubt she even knows what pegging is.”

One thing lead to another and soon, Uma was packing her strap on dildo. If anyone could convince Maddie to loosen up, it’d be Uma. And tequila.

When Uma arrived, she unpacked her bag in front of Maddie, “accidentally” dropping her strap on dildo on the floor.

“Oops,” she said, shooting me a look. Read more »

The Therapist [m] [F] [oral] [mast] [cum] [cheat]

I was having panic attacks daily when a friend told me to see her therapist. I’d been in a relationship that was going south. We were fighting all the time and, as a result, not having sex. Things were awful.

I made an appointment with a therapist who was a much older, very attractive woman. She had large breasts and long, tan legs. I was in my 30s. She was in her late 60s, but so beautiful it almost didn’t matter. Her skin was smooth, she was wealthy and wealthy looking.

After a few sessions, I already started to feel better. I knew this would help. Then, I started having dreams with my therapist. Sex dreams.

I wanted to share the dreams with her, but I was afraid she’d tell me this was crossing the line between doctor and patient and she would refer me to a man. So, I went weeks without mentioning the dirty dreams.

Finally, at the end of our session one week, I told her I’d been having dreams. With her. And I was hesitant to share them because I didn’t want her to cut me loose. Read more »

Learning a Thing or Two from my Cousin [m] [F] [oral] [mast] [cheat] [cum] [anal]

This isn’t one of those fake incest stories where we’re step-siblings or in-laws or godparents. Sasha IS my cousin, it’s just that she’s like, my third cousin, twice removed, blah blah. So, we’re technically related, but … it goes back quite a ways.

She’s also 10 years older than me. She’d babysit, tell me to stop being a nerd and kiss more girls. She’d tell me to dress cooler, less like my mommy dressed me. That sort of thing.

When she went to college, I was bummed. I liked Sasha. We had a ton of fun together.

Then, life interrupts and I didn’t see her for a long, long time. Until I got her wedding invite in the mail. I went. It was awkward. She hated the guy she was marrying, but her parents had been pushy about wanting grandkids and they were traditionalists, so … Sasha got married.

A few months later, they took a break and things remained like that for almost five years. Married, but not. She eventually settled one state over – just 20 minutes from my house – and we got dinner. Read more »

The Lesbian [M] [F] [oral] [mast] [cum play] [anal] [cheat]

I was new to town. The first thing I needed to do: Join a gym. The gym is where I go to socialize and chat. Don’t get me wrong, I’m all business once the headphones go on, but before and after, I’m chatting up everybody.

That’s when I saw her. She was a fit chick, long brown hair. Nike shorts and an old ratty shirt. I had to talk to her.

A week passed and we happened to both be training legs. I walked over and asked if she was almost done with her machine. She said I could work in. I introduced myself and soon, we were gym buds.

Her name was Kara.

Over the course of the month, I found out we actually had a lot in common. Same hobbies, same workout mentality, same music taste.

“Hey, let’s grab a coffee one day,” I said.

“How about Thursday after the gym?”

We friended each other on Facebook and I immediately stalked her page. She was into bodybuilding and had done some swimsuit competitions. Kept me busy for a few nights.

Half hour into our date, Kara said, “My girlfriend and I just ate a this great new restaurant.” Read more »

Bar Sex with a Near Stranger [m] [f]

I baked some chocolate chip cookies for my Grandma and was headed to her building to drop them off. In the elevator, I met the most unique looking woman I’d ever seen. She had tattoos all up and down her arms, those bar earrings that connect two piercings in her ears and, wait for it, a buzz cut.

She was a natural blonde with stunning blue eyes. She was wearing a lacy ALMOST see through t-shirt with frayed jean shorts and Chucks. And the closer I gawked, the more I realized something else. She had the finest body hair I’d ever seen on her legs.

“I love your hair,” I said.

“Oh?” She asked, running her hand across the buzz. And then I noticed something else! She had hairy armpits. I don’t know why, but it was closely trimmed and so fucking sexy.

“Yeah,” I said. “I think you’re … I don’t know … incredibly beautiful.”

“You do?” She asked. This time, she was blushing.

“I do. Your whole look is curious. But in a good way. I … I can’t take my eyes off of you. You’re stunning.”

“I’m Heather,” she said, extending her hand. Read more »

She wanted an extra dirty martini: Bar Handjob [m] [f] [mast] [swallow]

I have this friend. She’s Chinese and I am crazy attracted to her. We met at a party a few years ago and bonded over our deep, intense love of vodka martinis. It started off as casual flirting and quickly became a very serious inside joke.

We friended each other on Facebook, said our goodbyes and that was it. Every once in a while, I’d see a martini meme and I’d post it on her wall. She’d write back and say, “LOL.” That was pretty much it.

We added each other on Snapchat. I went out with some friends and ordered a martini. I sent her a quick video with text that said, “Wish you were here.”

She texted me back and asked, “Where are you?”

“Griffin Bar. Downtown.”

“I know it,” she said.

About forty five seconds later, there was a tap on my shoulder. I turned around. It was her!

“Maggie!” I said, leaping from my bar stool. “Holy shit! What are you doing here?”

She held up a martini. Read more »

Weekend at the Beach [M] [F] [f] [cheat] [mast] [oral] [swallow]

My girlfriend and her best friend decided we should go to the beach. I love my girlfriend, but we’ve been together 12 years and things have fizzled out in certain departments … if you catch my drift. Her best friend is Korean and smoking hot. She’s fit, thick but in a petit little package.

She’s 4’11 and can’t weigh more than 100 pounds. Her name is Hye. She’s also much, much younger than we are.

So, we book a three day weekend at a nearby beach and load up our cars with all the necessary stuff … but Hye’s boyfriend, Joseph, cancelled last minute because he got sick. So, it was just the three of us.

You’re probably thinking: Threesome! But, yeah, right. Tammy, my girlfriend, would NEVER go for something that cool. She’s a prude — big time. The first time I asked if I could cum on her tits, her eyes grew wide and she said, “Ew! Why?” I had to explain that it was a turn on for some guys.

“None of my past boyfriends wanted to do that! They were romantic and sweet. That seems … gross and vile.” Read more »

That one time in college [f] [mmmmmmm] [bukkake] [cheat] [oral] [mast]

Stephanie was my best friend. It sucked being in the friendzone with someone who I wanted to fuck so badly, but on the other side of the equation, I got to hear a lot of her intimate sexy stories. She often opened up with me when she got too drunk.

We’d sit around in my apartment talking about the good ol’ days and how we used to be so wild and crazy. There was nothing off limits, which meant I had a lot of mental material for when she’d leave and I’d jerk off.

This particular evening, I told her the story of how I got my first blowjob. I was a nervous wreck and the story ended with me jerking off into the girls mouth.

“Did she swallow?”

“Yeah,” I said.

“That’s good.”

“Do you swallow?” I asked.

“Oh, yeah. I love it. Unless the guy cums on my face.”

“You let guys do that?” I asked.

She giggled, “You need a better girlfriend. Of course I do. In fact … there was this one time when …” Read more »

His Name was Richard [f] [M] [oral] [anal] [squirt] [cum]

You’re asking me: How do you know his name was Richard? And I’ll tell you: I went to the mail room and looked at his mail box. I got his last name, got on Google and searched. Bam. Richard. 47.

He was a silver fox. He had short but stylish silver hair and a beard to match, muscles — so many muscles! And a few old tattoos on his forearms. I wanted to fuck him. I wanted him to fuck me. But I was too shy.

My parents bought me the apartment when I enrolled in college. They rented it out for two years and then, this year when I became a junior, I moved into it. My very own place!

I saw Richard on my first night in the studio apartment. He was on his balcony smoking a pipe. A pipe of all things. I thought, this guy is probably an author. Didn’t hurt my fantasy when he sat down and pulled out a thick book.

I started thinking about his cock and I wondered if it was as thick as the book he was reading. I just needed an in. I’m shy, okay? Too shy. I’m not like the girls in my school who send guys a pic of their tits and say “come over.” Read more »