no regrets Erotic Stories

With my best friend, we have a thread where we swap nudes and explicit videos. It’s our thing, a private game we’ve kept going for years.

One day, I had a twisted idea, a pussy photo contest. We’d vote, “like” our favorites, and eliminate the rest. Simple, just for fun, at least on the surface.

I gathered about twenty close ups from Reddit, scrolling late into the night to pick the best ones. And I don’t know why, but I had this crazy, perverse thought, slipping in a photo of my girlfriend among the others. Just one. Like a secret dare. Of course, he had no idea.

The moment I hit send, a rush of adrenaline hit me. This wasn’t just sharing porn anymore. It was crossing a line, mixing two worlds that should never touch. And that’s exactly what made it even hotter.

As the contest went on, her photo started making it through, round after round. Other girls got eliminated, but hers kept surviving. Every time a little heart popped up on her picture, my own heart pounded harder in my chest... continue reading

I was about 21 when I ran into my oldest sister's friend while out drinking. She was around six years older than me. It wasn't safe for her to drive home, so she came back to crash at my place. It was purely innocent—no flirting, no plans; I was just being helpful. We were both tired and tipsy. I offered to stay on the couch, but she said, "Don't be silly, just go to bed." So, we both instantly passed out in my queen bed.

It was summer, and the night was hot. I woke up feeling hungover, but still with my usual morning wood, just a sheet covering us. She was facing away, and as soon as I moved, she turned over. She was already awake but had been still to let me sleep. When she noticed the tent in the sheets, she laughed.

"Thank you for not letting me drive last night," she said, casually pulling the sheet and my boxers down, grabbing my cock.

"Better take care of this," she added, starting a nice, slow handjob. She took her time, and for how I was feeling, it was just perfect. She pu... continue reading

Backstory, my gf (now ex) Katie and I go on a trip to Vegas with her best friend Michelle and her boyfriend. We are all broke college kids at the time and decided to share a room to save money. Both Katie and Michelle are very attractive, petite with very athletic bodies. They have been friends for years, way before Katie and I started dating. So we had been in Vegas a couple days, nothing out of the ordinary had happened just the usual gambling, drinking and spending time at the pool.

It was the third night where things got more fun, we had been out all day and had gotten in bed ready to pass out, then right before I pass out, I hear soft moaning coming from the other bed. Katie and I look at each other and laugh, it gets louder and now we can definitely tell they are fucking. I’m definitely getting turned on at this point, wasn’t sure if Katie was feeling the same until I feel her hand slide into my shorts and grab my hard cock. She kisses me as she continues to stroke me, the mo... continue reading

I had never lived with boys before. I had always roomed with girls, but this deal was simply too good to pass up and it had to be similar, it just had to be. I guess I didn’t think about how I might be attracted to said male roommates.

When I moved in I completely last track of my thoughts when I met Marcus. Tall with a charming smile, I couldn’t take my eyes off of him. And then the other roommate, Ethan, showed up and he had the deepest blue eyes I’d ever seen.i tried to act normal but I fear I was blushing the entire time.

That first night after Marcus and Ethan had helped me move in, I laid in bed and tried to go to sleep but it evaded me. My body was warm and it craved touch. I tried to push the thoughts down but they only burned hotter.

I reached under the covers and pressed my fingers into my panties.

I thought about Marcus, shirtless, crawling into bed with me. I thought of Ethan pushing his shorts down and taking out his hard cock…

This is where I start to think too hard.... continue reading

This may be a long winded story, but also a fun & spicy one.

My wife and I have a neighbor named Leann. She’s a sweet, lonely, and quiet neighbor who we have lived next to for 7 years. She’s a widow, and I help her with the odd little task or repair often. I put in her widows A/C’s in the summer - that kind of thing.

My wife is with Leann one day chatting, and she comes back with a big smile on her face. “You’ll never believe what she asked you to do for her”

“Anything for Leann, what is it?”

“She wants to you jerk off for her for money” my wife says.

“No fucking way she said that. You are lying!” - I’m stunned. Leann is a little flirty, and I mean very little. The occasional “thanks handsome” is the full extent. She is respectful, sweet, and gentle at all times otherwise. She’s a gardener, and a grandmother.

“You must be confused. That’s not what she wants.” I say, before my wife shoves 5 crisp $100 bills in my hands and says “she said she wouldn’t ask you directly,... continue reading

TLDR; I'm a 23yo nursing student who sometimes babysits. One of my clients is a single dad I've known for years. After he came home from a bad date, I sucked him off.

I don't regret it at all, but I wasn't certain where things would go from there. Last night I found out :)

He texted me earlier in the week to schedule a babysitting appointment. I had to move some other plans around but I said yes. When I showed up he was trying to act calm and normal (lol) but I could tell he was nervous and excited. To me what happened last week wasn't a big deal, so I was just casual and friendly and that seemed to put him at ease.

He was going on a date. I told him good luck and I genuinely meant it.

Like last week, he came home late after the kids were asleep. Unlike last week, he came home looking excited rather than depressed.

And I could tell he was excited about me. He had a visible hardon lol. I pretended not to notice and innocently asked him how his date went. He said "it was fine" as... continue reading

Recently, I moved into a new apartment. I had been looking for a place for some time, and this one was perfect great commute to work, peaceful neighborhood. On the first day, I met my roommate. We had seen each other briefly before when I was still searching. She seemed nice, maybe even a little shy.

When I finally moved in, it took a few days to unpack and get used to the new place. She really helped me with everything—unpacking, moving things, etc. As she helped, we talked a lot. At first, she was a little withdrawn, but it turned out we had similar hobbies. We were both into running and even liked the same video games. We started talking more every day, but everything stayed on friendly terms.

At this point, nothing seemed unusual.

Maybe after a week, I stayed up a little late, and as I was going to sleep, I heard some quiet noises. A low buzzing and soft muffled moans. I couldn’t sleep. It lasted an hour, maybe two, before it went quiet. Things like that started to happen more an... continue reading

This is a story from a couple of years ago, back when I was still living in central London and swiping on Hinge as a way to pass the time.

I matched with this girl, Riley, and she was funny from the very first message. Not in the generic “haha you like dogs too” way, but actually sharp, teasing, like she was trying to wind me up from the start. It didn’t take long for her to mention (half as a joke, half not) that she had “a bit of an oral fixation.”

Now, I’ve been on Hinge enough to know people say weird shit on dating apps. But with her, it was different. She kept slipping it into conversation in this playful way, like she wanted me to know she wasn’t kidding.

Her photos made it obvious that her body was in great shape. Some of the best tits I've seen in tight fitting shirts and a bubble butt that looked like a perfect handful. I had no reason not to arrange a date and we agreed to meet up one evening after work. Nothing dramatic. Just a drink at a bar near my office.

And yeah, s... continue reading

I'm in my early 20s and working my way through nursing school. I've been a babysitter for a few families since high school, and I'm good with kids so I've kept doing it.

One of the dads, a man in his late 40s, is now a solo parent of two young children. (It's a sad story and I don't want to go into it.) I used to babysit for him occasionally, but he recently started dating and so I've been looking after his kids about once a week while he goes out. He's sweet and kind, a really great catch, but I can tell it's been tough for him to find the right person.

I can also tell he likes me (a lot of guys do) but he's every bit the gentleman and unlike some dads has never tried to cross a line, even though I've never hidden that I like him, too. We just have an understanding.

For a little while he seemed excited about someone he was seeing, but the last time he came home it was clear something had gone wrong. (Honestly, I could see red flags from a phone conversation I overheard between the... continue reading

I have always heard about how filthy guys’ group chats can be. Guys at work talk about it all the time. Now, have you ever wondered what’s in a women’s group chat?

I’m pretty certain that 99% of groups don’t have this, but I’ll spill the beans on a trend that started months ago.

(Everybody who participated was fully up for it and loved the outcome. They knew where the pics were going. It’s pretty much worship in our eyes, and it’ll make sense as you read on).

There’s 4 of us. Myself, an early 20s girl I used to work with, my friend with the dirtiest mind possible who’s 38 and then my bestie, who’s the same age as me (36).

Ms. Dirty Mind. The one with the big tits who won’t hesitate to get them out after a few drinks. They’re pretty beautiful tbh. Anyway, she started this. She starts seeing a guy who she bragged about had a BIIIIG dick. Every woman’s had one.

We knew they were going on a date, as usual, she posts a pic of her in a nice dress, nips on show. That’... continue reading

Okay so I go to the gym to scout out gym bros to fuck. Y'all already know that so I don't have to explain how much of a huge slut I am, but just now that it's all I ever think about. So when a nice man starting making eyes at me at the gym I was ecstatic. I was giving him some smiles and eventually went over to him to make some small talk. He said he had a small personal studio at his place, but he liked going to the gym to meet people. I asked if I could see his personal gym at home and he happily escorted me out of the gym and into his car.

So, I walked into this stranger's apartment and I am immediately struck by the fact that it's on the nice side of town. It's full of expensive looking shit and he immediately takes me to a gym that takes up an entire room in his house. It's full of free weights and benches and every little fitness tool they have up at the gym, he had it there.

He came up behind me and put his hands on my hips. I pressed my ass back against him and felt him start... continue reading

I'm Paul, 34 (*at the time), single with no kids, spending a week at a Mexican five-star resort with my parents, my older brother Kyle, his wife Beth, and their two kids. It's been great being with them, away from the usual family tensions found when everyone piles into my parent's house. The resort is beautiful and luxurious, with several pools, restaurants, and right on the beach.

After a couple of days, I was in a good routine. Initially, I had naively thought there might be groups of singles traveling here, but it was pretty much families. A few attractive college-age girls occasionally graced the pool, but this wasn't the place to meet anyone. My family would be leaving early Saturday to get back for a soccer tournament, and I had booked my stay to Sunday since I was already here.

I was alone in the main hot tub mid-morning on day five when an attractive woman I hadn't noticed before got in. She was about my age, with dark hair in a ponytail and a pretty face obscured by big sun... continue reading

So this story took place on Valentine’s Day when I was in my late 20s. I was single at the time and so was my friend who I will call Monica for the purpose of this story. I’d known Monica since first year of University and we were both fans of the same local band so we sort of bonded through that. Now Monica is a lesbian and was not shy about it. She wasn’t butch but had sort of a punk/alt thing going on with a Mohawk and piercings which was less common then than it is now. She is about 5’4” and had a nice body with C cup size tits and an ass you could stare at for days. Anyhow, we were both single during Valentines and since it fell on a Saturday that year, we decided to hang out, eat copious amounts of Chinese food, get drunk and play a lot of Mario Kart.

She arrived just after 7 and despite knowing that there was no chance of the night ending in sex, I had to admit she was looking good with her shapely legs exposed under her mid thigh denim skirt and a black t shirt which hugged he... continue reading

*If my wife ever reads this, she’ll kill me.*

When we lived in London, when my wife was still my girlfriend, her younger sister would come over to the UK from Poland to stay with us every summer, during her months-long break from university. She’d come to practise her English and to earn decent money by working temporary jobs we’d help her get.

It would be cramped, three of us living in a one-bedroom place, but we made it work. And she was fun to be around, my wife’s younger sister, she was relaxed and funny, plus she cooked for us. And, of course, she was gorgeous. I’ll call her Lena.

Lena’s seven years younger than my wife (she was older than 18 when this happened, don’t worry). They look broadly similar, tall, slender, blonde, beautiful. When she stayed with us, I had to keep reminding myself that Lena was essentially my younger sister, especially when I found my eye straying to her, when I found myself checking her out.

Lena sure didn’t make it easy though. She often wore tight... continue reading

I will try to keep my hands out of my panties long enough to write this down, because the memories of her make me ache.

I had posted previously about a friend I periodically masturbate with, and I thought it might be enjoyable to share about where this kink started for me.

Lexi was a close classmate during nursing school. She was good-natured, smart, albeit astoundingly sheltered. She came from a huge family of homeschooled children and had very little exposure to concepts like sex ed. Regardless of this, I took her under my wing and we became roommates after graduation, which was especially convenient because we got in to the same nurse residency together.

Although I had tried not to entertain these thoughts too much during school, I couldn’t help noticing that Lexi was insanely hot. Soft, slightly tanned skin, dirty blonde hair, and the most mouthwatering curves. The more time I spent as her roommate, the more I noticed how bouncy her ass was when she moved and how full her br... continue reading

Everything in this story is real, though I have had to take some license with the dialogue as remembering exact conversations verbatim is near impossible. I hope you keep an open mind, and I apologize in advance to all the guys who have had their sisters fucked by their friends.

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My name is Tyler. I'm your typical outgoing guy, nearing 30 now, and currently single. I've been very lucky in the sense that I have a confident and laid back air about me, and am blessed with charisma that tends to draw people to me. As a result, I've never had trouble attracting women. I'm not trying to sound arrogant or big-headed, but on nights out, I'll often be approached rather than having to make a move myself - that sort of energy. I hit the gym regularly, and stand 6'2" with broad shoulders. While I don't have 6-pack abs, I am strongly built. My hair is dark and close-cropped, and I usually have stubble across a strong jawline. I value intelligence, both in myself and in... continue reading

Idk if this makes me a slut or what. I guess i'll let you guys decide haha. I have been single for a little while now and I must say I have been having so much fun just enjoying my freedom. I know most girls probably prefer to find regular sexual partners and kind of just stick with them, but for some reason I like the variety and novelty.

Lately one of my favorite things to do when i'm hooking up with a new guy is to take off the condom while we are fucking, and tell them to cum in me. Just last night I brought home a guy from the bar and we started hooking up. He actually was a pretty good guy and he even asked me if I am taking birth control. I told him that I wasn't, which is true, and he pulled out a condom and put it on before we started.

We fucked for a few minutes and things actually started getting pretty intense. He was choking me, spanking me, and calling me a little slut just like I wanted him too. At one point he was fucking me roughly from behind and spanking me while h... continue reading

In my late 20’s I worked in real estate and met my one client when she attended one of my open houses. She caught my eye immediately, wearing tight yoga pants and a tight athletic top. She was pretty, blonde, shorter than my 6 ft, and decent sized tits. We didn’t talk much that day besides some info about the house, which she did not end up liking. But I gave her my card and told her if she wanted, I could be her exclusive buyer agent and show her whatever other houses fit her price range.

So she ended up texting me later that day and we kind of hit it off from a personality standpoint. Both kinda goofy, she liked my sense of humor, and I genuinely enjoyed showing her houses. But we never really crossed the line through the half a dozen houses I ended up showing her. I had a girlfriend anyways. I ended up learning she was semi-recently divorced, and only a year older than me.

So on closing day we’re at the title company, just me and her and the title agent. Now if you have ever bo... continue reading

So this story all stems from me breaking my debit card. Being the procrastinator that I am it took me a couple weeks to finally getting around to actually calling to get a new one. Luckily the bank was right around the corner so in the mean time I would just stop by the bank and grab some cash a few times a week. It didn’t take me long to notice it would always be the same girl who greeted me with a friendly smile from behind the glass at the drive thru.

So one day I had to actually go into the bank and luckily for me no one was at the drive thru so she came over to help me at the counter. I was finally able to see her name tag read Amber. I was also able to see she stood at about 5’2” with long brown hair and a petite little figure hidden underneath a baggy sweater. Amber had always been super friendly at the drive thru, but now that we were in person I couldn’t help but feel like I was getting some vibes from her. But since it’s literally her job to be nice to me I wrote it off bu... continue reading

Even though I'm Japanese by heritage, I was actually educated in America. I went to high school, college, graduate school, and even worked there for a few years. I lost my virginity to a cute white American guy. Due to work, marriage, divorce, family, and the general quirks of life, I’ve traveled around the world. I've lived in Singapore, Shanghai, Hong Kong, and now back in Japan.

About a few years ago, I started to meet random foreign men (most of them were Americans) who come to Japan for tourism.

The usual "date" goes something like this: We meet. We go somewhere to talk. And then we go fuck. I absolutely love it. I assure each guy I meet that I’m not a slut. I told them that “I don’t do this often. I never do this. … I’m not an easy girl. … I never get on my knees and suck the cock of a guy I just met. ... I have never jumped into bed with a man I just met.”

I tell them those things because it turns them on, and honestly, every time I suck on a stranger’s cock, I still get butt... continue reading