You dirty bastard: Kate’s affair with a boss [FM]

This is a hot past story told to me by Kate, an ex-girlfriend, about an affair she had with one of her bosses while she was married. As usual I have changed the names of those involved and, for this post, have changed some places and times. It is accurate to the best of my memory.

Recap: At the time this affair Kate was in her late 30s, stood 5’8, weighed about 130 lbs and was married with two children. Kate was slender except for her luscious round ass. She had shoulder length red wavy hair, green eyes, an upturned nose and pale freckled skin. She had almost nothing in the boob area. She was very classy looking and dressed very nicely. She was very well educated.

Kate and I liked to swap stories about our sex escapades. One Saturday afternoon we watched a porn video in which the protagonist, a young business man, had sex with his gorgeous female staff. After we had post video sex and were laying in bed, Kate told me she had fucked one her bosses for the entire time she worked for him. And on and off after she got a different job.

[MFF] The Wedding Plan: Something Borrowed [Cheating] [BDSM] [DDlg] [cuck] [exhibitionism]

“This is crazy.”

I laughed.

“It’s your wedding day,” I said. “Of course it’s crazy.”

As the Bride, you still needed to be in your fluffy white dress, bouncing around the reception. The first dance, cutting the cake and throwing the flowers were still on the agenda. Somewhere in this madness, you were hoping to have a second to gather your thoughts.

You were always the good girl. You focused hard in college and didn’t bother dating. Your best friend Bethany swore that you had no social life whatsoever, always turning down double-dates and parties.

That bitch confessed that she was worried you would still be a virgin in your 40s, given that you never got out and mingled.

Bethany didn’t know what the fuck she was talking about.

We met your freshman year of college. I was already nearly twice your age, deep in the “creepy” range of age gaps. But you knew. You knew that you were *really* attracted older men, and curious about kink.

I wasn’t even your first.

The innocent virgin that Bethany thought you were is a complete fabrication. You were just a discrete, smart slut.

My ex’s hottest law school classmate… [MF]

Years ago, I moved in with my girlfriend Liz during her first year in law school on the West Coast. We had a place off-campus, in an apartment complex where a bunch of her fellow students also had apartments—including her super-hot classmate Margaret, who would occasionally dog sit for us (and vice-versa).

When Liz introduced me to Margaret, I had just moved in and was preoccupied with a job search, so I didn’t think much about her except that she seemed nice. With long-ish, wavy blonde hair and a flowing, colorful dress, she seemed like sort of a hippie and I was just vaguely glad that Liz was making friends.

But then, a couple of days later, I was walking the dog and somebody called out to me in the parking lot. I turned around and saw Margaret waving and coming toward me, having clearly just gotten back from a run.

“Hey, Scott!” she said, taking out her earbuds. I remembered Liz telling me that Margaret lived just around the corner in our same apartment complex, overlooking the pool.

“Oh, hey!” I replied, suddenly seeing Margaret in a whole new light.

Reminding her she is owned. Part 2

[Part 1](https://www.reddit.com/r/Erotica/comments/zqeuto/reminding_her_she_is_owned_part_1/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

I lay you on your back arms grasped tightly to your chest unable to move as the rope holds you firm. I shift and lean my weight off the bed as you hear me rummage through my back pack then hear two clicks as a small vibrator gets inserted into your thoroughly used pussy turning it to the max as i stand up and walk into the living room hearing me open the door and go out to my car. Who knows how long I have been gone as this vibrator keeps switching the rhythm up. You think wait a second, this is a new toy so who is controlling this? Your man must be controlling the pattern as he sets up whatever he sets up. You try to use your legs to sit yourself up but struggle against the constant vibrations deep in your pussy making you moan and squirm when you hear the door to the room open and your I am back with a fucking mission. I come over and lift your body up over my shoulder like a sack of potatoes and carry your ass into the living room before gently placing you down on the couch. I gently slap your face to get your attention and you see the motor bunny is set up on a chair right in front of the couch directly facing the big screen.

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Categorized as Erotica Tagged

Cucking her ex by accident and training her body to love deep penetration [MF]

22 cm = 8.5 inches

I matched with this hot girl on Tinder. She had a pretty serious profile with some nice pictures which looked promising, though she had one picture showing she had a dark side to her as well. Still, I though it was worth a shot.

After talking a bit, she shared was living with her ex-husband. They had broken up some time ago, but due to economic reasons she chose to stay there until she found someone else. Asking if they were still sleeping toghether, she admitted they were having a fwb arrangement going, which admittedly felt more than just a bit wierd as I heard her ex in the background sometimes while we were talking.

She looked serious from the dating profile, but the more I got to know her the more I realized she was a dirty, dirty girl with a lot of red flags. She loved sex and had been with a lot of men over the years. During our convos, she also admitted making porn videos, including some with her ex she was living with. She linked me to her videos, which were anything but softcore.

Surprise Fling with a Friend After Mutual Heartbreak [mf]

I (M31) had a FWB relationship with a friend from high school (F30) about four years ago. (I’ll call her M.) Though we’re not together anymore, the memory of our time together still thrills me to my core.

M and I were in the same grade in high school and shared a few classes together. I liked her just fine then, but was preoccupied with other girls and only thought of her as a friend. After high school, M and I fell out of touch for a couple of years before spontaneously reconnecting over Facebook. She remained in our hometown while I went to college out of state, but we soon kept in touch on a daily basis – sharing our goals, thoughts, preferences, and daily chitchat with each other. We both pursued relationships with the opposite sex, but both remained single. We continued that way for five years.

[MF]All Day Edging Session Before Fun Night with GF

At the request of my girlfriend I spent the the whole day while she was at work watching porn and chatting online. I was also instructed to edge myself as much as possible. I think I spent at least five hours with my cock in the masturbation sleeve, using plenty of lube.

Why did she want me to do this? Because she wanted me to build up as big of a load as I could for her to enjoy that evening.

I made sure to give her updates via text during the day, letting her know what I was doing, including sending her pictures. First one was simply my computer screen with Pornhub open. From there they got naughtier. My cock in hand with the screen showing the porn I was watching. The screenshot of the dirty things I was chatting about online. All the toys charged and laid out ready for use. And then one guy I was chatting with started making suggestions (I’d shown him the pics I’d sent her already).

Send a pic of me wearing the nipple clamps? Sure. Me licking the tip of a dildo? Done. One of me deepthroating it? Well, as close as I could get to doing so lol.

My Best Friend and I ( The Awakening 3 Sum) Part. 1

This will be a few part series telling some stories that my best friend and I had growing up, to present time, There will be a little bit of everything in these stories. All 100% true. Enjoy.

“Is it cold or is it just me?”

I asked nervously, hoping I wasn’t the only trembling in the moment. It had little to do with being cold, and everything to do with laying naked in bed with my best friend and a girl. Just moments before something big happened. And we all knew it.

To take a few steps back, I’ll explain how we got there. I was around 19 or 20, back for the summer after college. With really only one goal in mind every waking day. To get laid. Which wasn’t an issue for me ever. By then I had probably already slept with 15-20 women and felt pretty good about my sex life. So my entire summer consisted of drinking, getting laid, and hanging out with my best friend, Justin. Back to the story.

There was this girl, Nikki, that had been trying to sleep with me since high school. She was a couple years younger than me so I had stayed away, but she was 18 now so I figured, what the fuck.

Collared in public – Anal, Ass play [MF]

Yesterday was wild.

We woke up from an amazing sleep. We cuddles and asked each other about our sleeps and dreams. Lily dreamed of some nonsense and I of course dreamed of some lewd acts we committed together.

We Lily wanted to go to the mall before the Christmas crowd. I came up with an idea. I asked Lily to pick the toy(s) she’d like to wear to the mall. She thought about her anal plug, but didn’t want to be plugged for too long, and it isn’t comfortable walking for long periods of time. She was worried that people could see her nipple clamps, if she tried on clothes. She quickly wrote off wearing her handcuffs, ballgag, and blindfold. With a devilish smile I suggested her collar.

I’ve been very turned on with the thought of collaring her. I would love for her to wear a permanent collar that only I have the key for. I was looking at fancy necklaces and titanium ring collars. Since Lily isn’t really into that I respect her wishes and haven’t bought any.

We do have a velcro collar that came with her nipple clamps. (there’s a story of her wearing it in my profile)

[MFF] how a New Year’s Eve party blowjob turned into the first time I came in my best friends mouth

First and foremost, I wanted to say thank you for the kind response to my writing the other day, it is inspiring me to write more about the fun I had in my 20’s.
About a year after I broke up with my high school girlfriend, I met my best friend while working at a retail store. We hit it off right away and became very close over the course of that summer. She was about 5 years older than me and had a lot more life experience, especially when it came to sex. I had only ever been with my ex and since we were long distance I hadn’t slept with her very often.
My best friend Marie on the other hand was an active member in the polyamory community. She had been in multiple threesomes, did swaps with boyfriends, and was just far more comfortable with her sexuality than I was. Over the first year of us being friends, she helped me come to terms with my bisexuality and my comfort with sex life.
By the time Christmas had rolled around, we hadn’t hooked up together yet but we did have a level of intimacy I hadn’t experienced in a friendship yet. We had slept in the same bed, she would change and get ready in front of me. She had shown me some of the porn she made with her exes and vice versa.
We were very much an open book to each other in that way. Which leads me to this story. One of our mutual friends was named Katie and she was a close friend of Marie. Both Katie and Marie were beautiful alternative girls with tattoos and such, but Katie had a really interesting body modification where her tongue had been split like a snake. It was kinda freaky at first, but it totally turned me on too.
One night after drinks, I mentioned to Marie that Katie had actually started to pop in my head during my dreams. I kept having dreams about getting a blowjob with a tongue like Katie’s. Marie laughed, but we never talked more about it.
Flash forward to New Year’s Eve, and I got to Katie’s apartment for a party. My best friend is already there with her boyfriend and a whole bunch of other folks from the Poly /bar communities. We all say hello and I participate in the party for about a half hour before Katie comes over with Marie and asks.
“Are you really a music major?”
“Um yeah, I am!”
“My flute isn’t working, can you look at it for me?”
(In retrospect, I really should have known this was a line) haha
I had worked in a music store in high school so I had basic repair knowledge so I agreed.
Marie, Katie and I all went to her room and she got out her old high school flute. She put it together and sure enough it wasn’t working on a few keys. She handed it over and it turned out that a spring had come loose causing some keys to never press. Connecting the spring fixed the issue and she got it working. She played for a few moments and both Marie and I did a polite golf clap.
All through this, we’re causally bantering like you do at a party, but as she was putting the flute away Katie drops this Line of, “So Marie told me that you like my tongue?”
I froze a little bit, glaring at my friend who had this shit eating grin on her face.
“Umm… yeah I do…”
“Been having dreams about it even…” she teased.
“Yeah, I am sorry.”
“Don’t be sorry! I am glad you like it, I wouldn’t have gotten done if I didn’t.” She said. “Marie also said that you haven’t gotten any since your break up.”
“Yeah… that’s right.”
“Well don’t get too excited, cause I don’t like the taste of cum, but if you wanted I could give head for a few minutes.” She said with a smirk. “It’ll give you a little bit of fun before new years.”
I stood there frozen for a second.
“I think you broke him.” Marie said.
“I would like that very much.”
They both laughed at me then, and Katie got on her news and undid my belt. Marie on the other hand got out her phone and was going to take a video.
“I will send it to you later.” She winked.
Katie slid down my pants and pulled my cock through my boxers. I was already half hard. She slid my dick through her lips and my breath caught.
She felt amazing. At first I could only feel the back part of her tongue, but then the two tips began rubbing on either side of my tip and it was incredible.
On top of that, it was the first time Marie had ever seen my dick, and the fact she was recording me was really turning me on.
They flirtatiously talked to each other, pretending like wasn’t there while Katie sucked Me. I gathered that I was going to get a 5:00 minute video or so before we all went back to the party. The would send me the video later to have fun with. The only problem was that I didn’t think I was going to last.
I hadn’t had any action in over a year and I was in a really hot situation.
After a few minutes, Katie pulled down my boxers so I was completely without bottoms and was feeling my ass while deep throating my cock. I finally needed to tell her to stop.
Haha she came up to laugh at me and Marie looked up and made eye contact.
“Holy shit, you’re going to cum already!”
She and Katie laughed.
“Dude, you try getting your first blowjob in a year like this!” I whine, laughing.
“Well Katie, do you think you could finish him?” She asks, panning the camera down to her.
Katie playfully squints her nose and eyes at the camera. “I don’t mind jerking him off, but I don’t like cum on me or in me.”
The way they were talking about me like I wasn’t there was so hot.
Marie laughed. “Okay fiinnneeee. Switch places with Me.”
Katie got off her knees and took the phone from her, and then Marie took my dick her hand before kneeling down herself. It was the first time she had ever touched me like this.
“Don’t think this is going to happen every time we hang out now, do you hear me!?” She asks.
I nod my head.
“Good, we’re still friends, but I am not going to leave you hanging on new years.”
She wrapped her lips around my cock and it felt incredible. Seeing my friend like this, having our shared story leading to this moment, the fact that it was being filmed was so fucking hot.
She occasionally would make eye contact and smile, but she was mostly on a mission. Her whole mouth sliding up and down, her tongue creating suction on my tip. It wasn’t very long before I was telling her I was about to cum. Her hands came up to my thighs as she sucked faster. My hand reached up to grab the top of her head to guide her and before long I was cumming deep in her mouth.
I could feel the cum pooling around my dick in her mouth as Katie moved the camera close to her face. She opened her eyes and mouth to smile with a mouth full of cum… my cum for the camera. She then closed her mouth and swallowed before sucking on my tip again.
Katie then ended the video and Marie slapped my ass a few times in a “good boy” sort of matter. Neither of them had removed any clothes, but it was very hot to get dressed while they were watching me.
We all got ourselves presentable and went back to the party.
Katie and I never fooled around again after that night, but she routinely teased me about it.
Marie and I however ended up having a several more adventures of a sexual nature over the next several years. Maybe I will write about them if you are all interested.