soulcrushinganxiety, Author at NSFW story — Page 17 of 28

MY OLD HIGH SCHOOL TUTOR [mF] [oral] [anal] [gape] [spit] [piss] [swallow] [facial] [mast] [rimjob] [prostate]

In high school math wasn’t my strong suit. At one point, I had a tutor who was an elderly British woman, but she retired to Florida to live out her years and recommended a woman named Nicole.

“You’ll just love Nicole,” she said with a wink.

I knew what she meant the moment Nicole walked in. She had curly blonde hair, large breasts, a tight stomach, toned legs, a firm ass. She looked like Julie Bowen from Modern Family. But even the best tutors, like Nicole, had trouble reaching me. I just wasn’t interested in math. One afternoon, Nicole had one of those “lightbulb moments” when she caught me staring down her blouse. She was wearing a lace bra—black—her cleavage was hard to ignore.

“Oh,” she said, a hush falling over the room. I was 100% certain that would be the end of that. I blushed, stammered, struggled to come up with a lie, but instead Nicole just winked at me and said, “I think I know how to motivate you.”

IT STARTED WITH A TEXT [MF] [cheat] [oral] [prostate] [mast] [creampie] [swallow]

I’m at the gym five days a week, so it’s pretty normal for me to befriend a lot of the other regulars. One, in particular, is a short haired woman named Lucy. She’s got large breasts, hard nipples, thick thighs, and a flat stomach. I see her there once a week, when she works out with her trainer. So, naturally, we got to talking.

“Wish I could chat longer,” she said. “But I have to get back to the office for a meeting. Gotta run, but … text me.”

I took her number, she disappeared into the locker room and emerged twenty minutes later in office clothes and high heels looking as sexy as you could imagine.

I texted her that evening to ask how the meeting was. There was an obviously flirty tone to the overall conversation … and then she mentioned her husband had fixed dinner, so she had to go. Husband? Well, there goes that, I thought. But, I saw Lucy at the gym a week later and she gave me a hug and a peck on the lips, which was intriguing. I’m no hero, though, not beyond fucking a married woman in the name of decency and respect. And if Lucy was unhappy or miserable in her marriage, she knew what she was doing. Sure, I felt slightly bad for her husband, but I would be blown away if he was happy, too, so maybe sleeping with Lucy would be a blessing in disguise—freeing them both from a miserable marriage? Read more »

NEW NEXT DOOR NEIGHBOR [mf] [cheat] [oral] [squirt] [swallow] [facial] [mast]

I’ve been living here for two years now. My previous neighbors sold their apartment to a younger couple. But the day they were set to move in, her husband got called away for an out of town work trip. It just so happened I was getting my mail downstairs when I caught her unloading boxes one at a time, dragging them, grunting, sweating, cursing.

She was a stunning brunette. Skinny. Large breasts. She was wearing sweatpants and a very loose fitting tee that hung down when she bent over. Her hair was in a ponytail. She looked sort of like Gal Gadot without makeup. And when she lifted her arms up to grab a box, I noticed she hadn’t shaved her armpits. It was unique and in a weird way, it was a turn on. Was she a free spirit? Did she keep an open mind?

“Let me help you,” I said as I walked outside.

“Oh,” she said, lifting her shirt up, exposing her flat stomach to me as she wiped her forehead. “You really don’t have to.”

HE WANTED TO WATCH [mf] [swing] [oral] [mast] [cum]

My next door neighbor looks like a young Christina Applegate. She’s petit, blonde, and unlike the real Applegate, my neighbor has pierced nipples, which I can see jutting through her practically see through tank tops.

My neighbor is a bombshell and she knows it. She walks around the building in her booty shorts and see through tank tops and in the winter, simply adds a super heavy puffy jacket and knee high boots.

When I first moved in, she was one of the first people I met. She gave me a big friendly hello, welcoming me to the building. As a finance guy, I decided to go to the monthly board meetings, but she was never there. Maybe she rented, I guessed. Or maybe she just didn’t care and, like most people in a large building, assume someone is taking care of what needs to be taken care of.

One afternoon, I listed something for sale on the building’s Facebook page and my neighbor, who is named Lynn, by the way, liked the post. Of course I immediately recognized her and friended her. She accepted right away and did the exact same thing I did: Went through my posts, liking various ones to get a better gist of the kind of guy I was. Read more »

The Dating Game [mf] [oral] [mast] [squirt] [facial]

Gotta make dating interesting, or else we end up miserable and frustrated. Dating can seem ultra repetitive, especially if you’re dating some basic bitch or douchebag guy who asks you all the cookie cutter questions: Where did you grow up, did you have any pets and/or siblings, what do you do? Baaaarf.

I like to go right for the juicy stuff, which makes dating fun, but the very real downside is it makes you very endearing. Women think you’re unique, special, funny, interesting and they don’t wanna let you go. But they definitely fall head over heels, which means no trickery and no deception needed. They’ll suck your cock in the car ride home or let you finger them in the tucked away corner of the bar on date one.

But, so long as you’re being honest about your intentions, it’s all good.

I was working on this theory that interesting first dates lead to first date sex. So, I lined up a series of dates. The first date, I went all in, asking strange, silly, goofy questions instead of the boring personal stuff that ends up feeling somewhat scripted if you go on enough dates. I went out with a woman named Sasha and my questions totally caught her off guard. Read more »

Silver Fox Fucks a 21 Year Old [Mf] [oral] [prostate] [swallow] [creampie] [mast]

Jeff was almost 40. After a lengthy failed marriage, he looked to rebuild his life. As with most people exiting a long term relationship with the prospect of dating, he skewed younger and he had his reasons. People his age were likely also divorced and with that, came divorce drama, which he wished to be far removed from. Of course, dropping the age range down to mid 30s brought it’s own problems. Women in their early 30s wanted kids, husbands, families, the security of an older, career established male.

Jeff didn’t want to go down that route, either, which lead him to one final conclusion: In order to have 100% no strings attached sex with as little drama as possible, he had to skew very, very young. We’re talking early 20s, here, girls right out of college who wanted to have fun and then move on to the next casual fuck.

He knew the odds were not in his favor, though. After all, he was turning 40 soon. Would a 23 year old really want to fuck a 40 year old? He decided honesty was the best policy, and so he crafted his bio to say that he was looking for something very casual and wanted to have fun. Read more »

CREAMPIE ANGST [mf] [mF] [oral] [mast] [swallow] [milf] [anal] [creampie] [creampie eating]

My ex knew I didn’t want kids, and yet, she tried to get pregnant time after time. Things got so bad that I developed a severe case of sex related erectile dysfunction. I didn’t want to have sex, and this was my body’s get out of jail free card. My ex couldn’t get pregnant if I couldn’t get hard.

Naturally, we broke up a short while after. But my anxiety followed me. Shortly after the breakup, I decided to go online and find some fun. I figured the best way to get over someone was to get under someone else. I hooked up with this skinny blonde with perky tits and a firm muscular ass. She was absolutely cute and adorable, but when her clothes were off and she was fidgeting and biting her bottom lip, her hair over her eyes, I couldn’t perform.

SHAMED IN FRONT OF HER HUSBAND TURNED TO PLEASURE [mmf] [anal] [saliva] [piss] [rimming] [double anal] [facial] [spitting]

Anna fucked up pretty big time. We won’t go into the details, but Mark was livid, hurt, confused, ashamed, embarrassed. You pick an adjective, it probably applied to the situation. She said she’d do literally anything to make up for her mistake. And he knew she meant it. She’d fly him around the world, take him to the best restaurants, buy him an Omega watch if he wanted.

But Mark didn’t want any of that. He wanted her to experience the same level of shame and degredation she caused him to feel. He wanted her to loathe herself and feel ashamed. He wanted her to sit in the car and sob and weep afterwards, as he’d done when he first found out what she’d been up to.

And, most disturbed of all, he wanted to watch. He wanted to watch her beg and cry and plead and say, “enough,” just like he was forced to do. He felt sick to his stomach and now he wanted her to feel the same way. Would it fix things? He was almost certain it would. Both of them would be so ashamed and disgusted that they’d have to move on together, rebuild, start fresh. Read more »

Found my Niche

Kids? No thanks. Marriage? Eh, not for me. Sex? Lots and lots of sex? Yes, please. Here’s the problem, though: I am in the wrong age bracket for that sort of activity. It’s not that 35 year old men cannot find women to fuck—it’s just that the women who want to fuck me, and who are in my age bracket, want to get married and have babies.

This means the women available for me to fuck are either extremely young (we’re talking 18-25), or are older and have either given up on marriage and kids or have already been down that road (we’re talking 40s and up). Now, I don’t MIND fucking 21 year olds or 50 year olds, so I’m not complaining. But the 21 year olds don’t always want to fuck a 35 year old. And the 50 year olds don’t always want to fuck someone 15 years their junior.

This means, sadly, that my options are relatively limited: I must fuck women who are in my age bracket. So, how do I do that without misleading them? I’m not going to use any sort of trickery to get someone into bed: the promise of the possibility of a future, saying I might want kids, but I’m not sure, etc. Anything that gives false hope isn’t my thing. The best policy, as always, is honesty. But honesty also pushes away a lot of women. Read more »