NSFW story — Page 10094 of 11466 — collection of stories you shouldn't read at work

My First MILF [MF]

My name is Andy. I grew up in a very religious household, so I was a late bloomer. It took me until college to have my first kiss, and I didn’t lose my virginity until I was twenty-one. Since then, I’ve been doing my best to catch up. This is the story of the first time I slept with an older woman:

As I’ve mentioned in previous posts, I’m in the Army. That experience led to a lot of opportunities to travel, see new things, and meet new people. It is not, however, particularly conducive to dating. Fortunately for me, I had plenty of friends who were happy to set me up with people they knew.

One of these friends was an older woman named Janet. I was over at Janet’s house, having a beer with her husband, when she mentioned that she knew a woman who was looking to date. Janet asked if I was comfortable with a woman having kids, and being a little older. At the time I was 24, and the woman with whom Janet was setting me up was 37, and had a 17-year-old son. I told Janet that I was game as long as she was a cool person. Read more »

A trip to the Lake District [MF] hold the moan.

I have a few stories from my past following on from the reception of my tube encounter a few days back.

As / when I’ve got time to write them, I’ll be sure to do so.

This story involves my friend Helen.

I came out of a relationship and in all honesty was trying to get myself back in the dating scene. Moving to a main UK city (leeds) I decided to jump on pof and see who was around.

Helen was a tall (5ft 10), blonde hair, great eyes and wonderful smile. Toned body from excessive gym and netball playing, with a tattoo running from her ankle to thigh. She had a very well to do family and went to boarding school. We dated on and off (once it became apparent I wasn’t in the best of places from my relationship) and fucked a lot. She wanted sex, I wanted sex….. I made her squirt….. so it was a no brainer for us both. But at the time of the story despite being friends we’d not had sex in months, as she was on/off with a guy from work. Read more »

Sunday in the Bed with Ariel [MF]

I don’t know what I did in my prior life to deserve this summer. It’s been unforgettable. A year ago, I would have scoffed at the thought of me having two gorgeous women available to fuck whenever they pleased.

I was engaged, but that relationship ended. Am I entirely over her? No. But one of the many reasons we weren’t compatible was our difference in sex drives. Mine’s intense. Hers wasn’t. I fantasized about sharing her, I wanted to take risks – she wouldn’t entertain any of that. There’s been a lot of heartache since we split, but in the last six months I’ve embraced my sexuality and really set out to experience everything I’ve fantasized about and been missing out on. You can (and should) read about those adventures in my previous posts. And I won’t get into anymore of my background or description here, as I’ve covered it pretty extensively.

I have two FWBs right now – two gorgeous, smart, sensational women – and I don’t know how long my luck can last, but I’m totally at their mercy. I’m not necessarily their only partner either, and we’re all in the clear health-wise. Caitlin is one of those girls (The Eighth Wonder of Reddit), and Ariel is the second. This one’s about Ariel. Read more »

Watching [30M]y [24F]riend masturbating in Iceland while I was (supposedly) sleeping next to her [MF] – Pt. 2

[Part 1 here](https://www.reddit.com/r/gonewildstories/comments/6yzlmy/30masturbating_to_my_24friend_in_iceland_while/). Read at least the first couple paragraphs for a description of Kari as well as what the hell is going on.

A couple days passed and I was noticing an unsettling phenomenon. Walking behind Kari up the stairs, I would steal glances–okay, more like long, drawn out stares–at her ass, each side tightening by turn, perfectly accentuated by tight pants. But one day, as she took the first step up and I prepared to begin my tortuous enjoyment, I began thinking of how she’d pulled a muscle a little yesterday, and how it must hurt, but of course she was too stubborn to say anything. And instead of holding my hand back from cupping her ass, I found myself holding it back from settling gently around her waist, ready to hold tight if she fell.

This was a problematic development. Kari was just as uninterested as ever, and in my rational moments, so was I. Nothing lay down that path but pain.

The nights stretched out, eternities of conscience-stricken edging. One morning my balls were sore the whole day–worst case of blue balls I’ve ever had. Read more »

Night on The Town, Part 3 [MF] [Oral] [Lite Exh] [Third Person]

(Part 2 can be found [here](https://www.reddit.com/r/eroticliterature/comments/6q8gwo/night_on_the_town_part_2_mf_oral_lite_exh_third/)).

 

Kate opened the bathroom door, revealing an elderly woman, her frown pulling the wrinkles on her face taut. The hallway was empty besides her, and beyond that the soft, jazzy music of the restaurant played undisrupted. If anyone had heard her orgasmic shout, they hadn’t reported it.

“The other bathrooms are full,” the woman said, shaking a fist, “presumably being used for their *intended* purpose. I’ve half a mind to tell management about you. I thought this was a *respectable* establishment.”

Kate and Mark filed out of the bathroom, giving the irate woman a wide berth. She shuffled into the bathroom muttering under her breath, and slammed the door with as much force as she was able.

The couple exchanged a glance, trying to bottle down their laughter. Mark straightened his tie and lead the way back to their table. He looked around the restaurant as surreptitiously as he could, but nobody seemed to realize he was there. Every table was in their own little world. They were all separate planets, orbiting each other but not quite touching. There was a sort of quiet beauty to that, he thought. In way, each couple were the most important people in the world. Nothing else mattered. He looked at his wife, took her hand. That was exactly the way he felt tonight. Read more »

Night on The Town, Part 3 [MF] [Oral] [Lite Exh] [Third Person]

(Part 2 can be found [here](https://www.reddit.com/r/Erotica/comments/6q8gyb/night_on_the_town_part_2_mf_oral_lite_exh_third/)).

 

Kate opened the bathroom door, revealing an elderly woman, her frown pulling the wrinkles on her face taut. The hallway was empty besides her, and beyond that the soft, jazzy music of the restaurant played undisrupted. If anyone had heard her orgasmic shout, they hadn’t reported it.

“The other bathrooms are full,” the woman said, shaking a fist, “presumably being used for their *intended* purpose. I’ve half a mind to tell management about you. I thought this was a *respectable* establishment.”

Kate and Mark filed out of the bathroom, giving the irate woman a wide berth. She shuffled into the bathroom muttering under her breath, and slammed the door with as much force as she was able.

The couple exchanged a glance, trying to bottle down their laughter. Mark straightened his tie and lead the way back to their table. He looked around the restaurant as surreptitiously as he could, but nobody seemed to realize he was there. Every table was in their own little world. They were all separate planets, orbiting each other but not quite touching. There was a sort of quiet beauty to that, he thought. In way, each couple were the most important people in the world. Nothing else mattered. He looked at his wife, took her hand. That was exactly the way he felt tonight. Read more »

[Humil][chastity] Innocent naive college virgin wins a sorority’s life time virgin award. His prize isn’t what he thought it was.

I was homeschooled by my overbearing mom until college. She wasn’t religious, but she was as sheltered and naive to the world as one could get. It was never something I thought about growing up, just as a boy doesn’t know what something is, like a combustion engine, until he’s told of its existence, I didn’t know about sex. I was aware people had it, it’s how babies were made, but outside of that, I was clueless. I never thought it’d be a prominent factor in my life. Boy was I wrong.

I started college at one of the largest universities in the country. Unbeknownst to me, also the largest party school. I found this out via a sorority event believe it or not.

At the time I was unaware, but apparently during pledge week for the major sorority, the pledges are given the task of finding a virgin and bringing them to a party. Like a dinner for schmucks type situation. Read more »

[Request] A boyfriend in love gets unknowingly cuckolded by a disgusting older man who eventually even becomes his boss.

“Are you James Whiting?”

“Uh yeah, who are you?”

“My name doesn’t matter. I was paid to find you and deliver these, they’re divorce papers. I was instructed to tell you to sign them and have them to Julia by the end of week” his hand was stretched out holding a thick manilla folder.

I reached to take it. Said good bye to the man and sulked back into my apartment, collapsing in my sofa, feeling defeated.

I looked back on my relationship with Julia, thinking about where exactly things went wrong. I had always neglected to reflect, trying my best to stave off the shame and guilt. But I was always left wondering why it all went to shit. Or rather, how?

I got out my laptop and started typing it all out from the beginning. I always enjoyed writing and had always found it cathartic. So, here’s my story. Read more »

On the train to Farlo [FM]

*I want him inside of me. God damn the consequences, I want his cock in my pleasure hole.* This went through Evine’s head right before she and Davon had sex in the train’s bathroom.

One month earlier Evine wasn’t that excited that she had to go to summer school. However, it was the only way for her to stay in her prestigious art school. With some resentment, she looked through the different summer courses offered by nearby colleges. None of them looked good to her. In the end, she settled for the “Sociological perspectives on the function of Art” course given at a liberal arts college a three-hour train ride from her art school.

A month later, when Evine had packed her bags and was on her way to the train station, she still wasn’t excited for her week of summer school. The weeks before she left had been spent lying on the beach, recovering from her finals. She wasn’t keen on switching the beach for the classroom. But well, what can you do?

When Evine arrived at the station she thought to herself. Let’s try to be a bit more positive and make the best of my time in Farlo, the town Evine was going to. Read more »