It’s not cheating if you only look… [M/F]

Guilt and Pleasure: Volume 2

It's Not Cheating If You Only Look

by Matthew Myen


If this is the first of mine you have read, please read the first part of Guilt and Pleasure before continuing.

Well, that first post blew up, didn’t it? I’d just like to thank everyone for their words of support and encouragement. If you just read it and enjoyed it – that’s enough for me.

I have bad news for anyone who thought the first one was too long… the second volume is more than double the word count. I couldn’t find a good place in the events to stop without feeling like a tease.

Finally, if you would prefer to read on Kindle or something, have a look at the afterword in the comments.


Prelude

Plan B (or the ‘Morning-after pill’) is a type of emergency contraception that can prevent unwanted pregnancy after unprotected sex.

It was late. Late enough that even the semi-nocturnal birds that roosted in the trees of the park near our townhouse had quit their trilling. Jessica slept soundly next to me breathing in the slow rhythm of deep sleep. My phone glared painfully in the darkness as I browsed incognito for some statistic that would help me sleep.

Swiss Finishing School Pt3 [MF][anal]

John had been stood up. He had been meant to meet his friend David for a drink, but just as he was arriving at the bar, David called and said that he'd managed to get a date with a girl he'd been trying to screw for months. Obviously, John could hardly begrudge him that. He decided to go in for one drink anyway.

With his drink in hand, he sat at a small table by the wall. He surveyed the girls at the bar. One in particular caught his eye. She was about 5'8, slender but curvy, with long blonde hair and a beautiful behind, wearing a tight silver mini-dress and matching heels.
As she turned to speak to a friend, he realized he knew her. It had been a year ago, the best night of his life, four naked girls in a dorm room in Zurich. This one was Kimberly, and he'd been her first. Just then, she glanced around the room, and caught sight of him. There was a flash of recognition, and a big smile. She said something to her friend, then walked over, Martini in hand.

Move to a new city, join the swing set. ([m/f], [m/f], [m/f], observed [m/f/m] and [f/f])

A little more than 24 hours ago, I made a life-changing decision and had the best night of my existence. Enough that I want to write about it and share it. And I already want and need more.

My vitals: straight male, mid-30's, mid-divorce. 5'9", about 250. If I were into men, I guess you could say I'd be a bear. I've had some experience with kink and non-monogamy, but since getting divorced and moving near a major northeastern city, I've decided I want to explore these more. I know I'm a dominant person who isn't all that big on physical monogamy, but in terms of actually playing, I haven't done much.

As it turns out, my ex-girlfriend from college, Carrie, had also gone on the same journey (divorce, sexual exploration). However, she joined a couple of swinging groups in her area (which was closer than I expected) and has blossomed big-time. A while ago, she mentioned that she was going to be dancing in a stripping contest at one of those groups. Back when we dated, Carrie wasn't exactly repressed, but she's gone headlong into kink, so I desperately wanted to see her in a new light. And have some fantastic sex, of course.

Swiss Finishing School Pt2 [mf][ff][virgin]

John arrived at the school just after 7pm. He approached the west entrance, just as the note had instructed, but all was dark. He waited a few minutes, then turned to leave. Just then, there was a quiet creak from the door, and a soft voice whispered: "this way!” The door was open just wide enough for him to slip inside into the darkness of the building. "Take your shoes off,” whispered a female voice, "We need to be really quiet. Here, I'll make some light.” She turned on her cell phone, and in the dim light he saw it was the red-headed girl from that afternoon. She was still wearing the plaid school uniform skirt, but instead of the crisp white shirt she wore a polo shirt. The nipples on her large breasts showed prominently through it, and it was obvious she had no bra on. He removed his canvas deck shoes, and she led him down the corridor, then up a narrow flight of stairs. At the end of this corridor she opened a door and they stepped into a dark room. As soon as she closed the door, a light was switched on. It was a dorm room – there were two beds, two wardrobes and two chests of drawers, and on the beds sat the other three girls from the afternoon's class.

Borrowing the neighbour

This is a story I wrote for another site and I thought you guys might like it. Not sure where to put it so posting in both /r/eroticliterature and /r/sexystories. I hope you enjoy it. Borrowing the Neighbour

It had been a long and tedious day in the office, and by the time 5 o'clock came around, Cindy was ready for a long soak in the hot tub on her deck at home. Just the thought of relaxing on those well placed jets started her nipples tingling. Packing up and saying goodnight to her colleagues was done in double quick time tonight and before she knew it, she was headed for home.

A quick stop to pick up some food and a bottle of wine for herself on the way home and she was ready for a night in by herself. Her husband had taken the kids to his parents in the next city over and she had the house to herself for the weekend. Her mind drifted on the drive home wondering what she might do with the time, besides soaking in the hot tub and topping up her tan. Maybe she could tease the neighbours again. She had caught them both watching her on occasion, alone and sometimes together.

Pervy Germans Pt. 2 – Finger-fucking on the Autobahn leads to high-velocity blowjob, veritable shower of cum [f/m]

This is the first time I've seen the foreign boy toy since my last story.

He's driven countless hours through tough conditions to meet me at the airport, and recounts his harrowing tale as we hit the highway for the long drive back to his hometown. We catch up, joke and belt out Michael Jackson songs (we are in Germany after all), but really, all I can think about is how I've spent the past 2 weeks fantasizing about wrapping my lips around his dick as we race down the Autobahn; riding him in the front seat; being bent over in the back seat, and then on the hood, and then somewhere in the woods. (It's only been 2 weeks, and yet it feels like forever.)

We eventually pull over to a rest stop for a bite to eat and for the first time, he is able to sit back and look at me without car horns honking. We take a moment to drink each other in before leaning in, and what begins as a series of soft kisses, exploring tongues and tasting quickly escalates. Soon we are grabbing at one another, licking, biting and making out like horny teenagers, in a rest stop parking lot in broad daylight, surrounded by semis full of interested truckers. (I am not sure if he notices this, but I certainly do, and it is kind of a turn-on.)

The Bedwarmer [MF]

The head housekeeper called all the slave girls together into the kitchen.

"The Master has just received word that a member of the Senate will be spending the night with us. He had planned to travel through the night, but a wheel has broken on one of his wagons, so he will be stopping here." She looked sternly at us all. "This is a big opportunity for the Master to make a good impression, so we have a lot of work ahead of us."

With that she began handing out tasks, and as each girl received her orders she scurried off. Eventually I was standing there alone. "The Master has decreed that you are to be the Senator's bedwarmer. Now go join the girls preparing the guest rooms."

I groaned inwardly. Whilst it would certainly help my position in the household to be chosen to see to such an important guest, "bedwarmer" was a euphemism for "girl who gets humped by a fat, sweaty old man and has to pretend to enjoy it". Important men traveled with a whole retinue of guards and slaves, of course, but it was traditional for the host to offer a bedwarmer for the first night of a guest's stay, and it was a sign of trust in the host to accept.

My neighbor has loud sex. So I have loud sex with my neighbor. (F/M)

This is a long one haha (sorry not sorry :p). Hope you make it ;)

The dude who lives below me loves to have extremely loud sex. At least once a week, I’ll pass by his door on the way up to my apartment and get overwhelmed by the sounds of women in the midst of (what I assume is) the best sex of their lives. At first I thought it was just a woman, alone, enjoying herself far too much. But then after a few months, I realized it was always a different woman – always making the noises one makes when they are being fucked exceedingly hard.

So I got curious. I’d start to linger whenever I heard. Sometimes I’d hear them outside, through an open window and I sit for a while wondering just what the fuck that man was doing in there.

Finally it happened. I was coming home tipsy from a late-ish happy hour (maybe ‘round midnight). He was leaving, locking his door. I stopped, and I had to ask. “Are you the dude having loud sex all the time?”

Italian Lingerie Store [FF]

My name is Gabriela.

No, it's not, but I'm not telling you my real name. I'm 29 years old. I was 29 last year too.

I'm a professional girlfriend. My boyfriends' wives would call me a whore.

My boyfriends buy me jewelry, clothing, pay my rent, my credit card bills, sometimes even give me shares in their companies or illegal stock tips.

What do they get out of it? What do you think? They get a beautiful woman to go out with, to secretly take on business trips, to make their friends jealous, but most of all, they get mind-blowing sex. The kind of sex their wives couldn't even dream of competing with. Of course, their wives are busy running the house, organizing the help, raising the kids, planning fund-raisers.

I don't have to do any of that crap. I spend my days making myself irresistible to their husbands. I get massages, facials, manicures, tennis coaching. I work out with my personal trainer four times a week. I make sure I'm the kind of woman a rich man will risk everything to be with, except that there's no risk. I'm discreet, I never make a scene, I never ask them to leave their wives, I never call them at home, I never get pregnant. They know this, and they appreciate it.

From Stripper to Hooker [FM/FF][oral][anal][prost]

I'd been stripping for about 6 months. It wasn't my first choice, but I'd been unable to find a job since graduating with an engineering degree – it seems people just couldn't handle the idea of a pretty, female engineer.

It was an ok gig, and it more than paid the bills. I certainly didn't get off on it like I hear about with some girls – it was just a job.

One evening after my shift, the club manager called me into his office. He told me there was a message on the office answering machine the day before asking about hiring a stripper for a private party. He said they didn't do that (something about insurance), but I could have the number for $50 if I wanted a little side work. I'd heard other girls mention this arrangement, so I was pretty sure he wasn't scamming me, and I figured I could probably make good money doing the party in less than an hour, then still make my shift at the club, so I handed over the cash, and he gave me a torn piece of paper with the name "Mike" and a number.