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Stories in no regrets

234 stories · Page 10

girlfriend’s best friend

So back in 2012 my girlfriend and I hosted a Super Bowl party at our apartment and invited some friends, her best friend who I’ll call (for privacy) Meg was there, her bf had to work so couldn’t make it. She’s a beautiful Salvadoran girl, about 5 ft, big eyes, b cups and a nice big ass. My girlfriend (Vicki) is a super gorgeous Mexican girl with DD boobs and a rockin body. There were others there too, we were all having a good time drinking, yelling, just socializing. After the game ended we all took some shots and people started leaving (not everyone was drinking so there were DD’s) Meg was pretty buzzed and Vicki was pretty hammered but told Vicki to stay so she doesn’t have to drive home, it was about a 30 min drive, she was reluctant at first but then agreed to stay. Vicki knocked out on the couch, she usually passes out when she drinks heavily so Meg and I were just watching some tv and chatting a bit. She jokingly said “well there goes your time to get lucky tonight” we both gig

How I saved a girl's life and was rewarded with a sexcapade I've never been able to top. (Part 5)

Part 5 The game was afoot. Everyone had been enthused by my idea so Jake and I got up from our seats to make another trip to the bar. As he and I stood waiting, I asked him how his night was going with Emily. He gave me a double thumbs up, said she was good craic and that he thought she was jealous that her cousin was getting some and not her and that was the reason they were getting so friendly. We'd all agreed back at the table that we were getting a bit too tipsy too quickly, and it seemed like Emily had thought things with Jake were moving a little fast. To mellow everything out a touch and make sure the night wasn't over too soon we decided on getting a pint of water each. We agreed that only once once we'd all had the water, we'd start our drinking game with the most fun drinks of the night so far: Tequila slammers. All around the table we sat, and once the age old mantra "salt,tequila,lime" had been reiterated for what must've been the billionth time in the spirit's

Wife shares my big cock with my college crush, part 2: "fill me"

After the life-changing experience I shared with Jane and my wife last weekend, I could barely think straight all week. The images of Jane’s mouth stretched wide around my big cock, my wife nodding with encouragement, were seared into my mind. My life was at a complete standstill. I was terrible at work, distracted at home. I wanted more. My first priority was finding out what my wife had thought about the whole thing. While it’s true that she had initiated proceedings, I wanted to make sure she didn’t have any regrets. I walked into the living room last Monday night. “So, fun weekend huh?” I tentatively offered. My wife smirked at me. “It was,” she replied. “What was your favourite part? The dinner, or?” I laughed. “The dinner, I loved the dinner.” I said. “Did you?” “Of course I loved the dinner, I made it happen!” she laughed. I asked her what were the odds we’d have a dinner like that again sometime. She paused and considered. She stood up and walked across the room to me.

My friend came to me weekly to shave his dick and he always got a surprise at the end.

My friend always said that shaving his dick was kinda scary and he always had a bush down there \[M21\] But one day he came to my house and asked if I could give him a hand. I was a bit hesitant at first but I decided to help him out. We went to the bathroom, he had brought tools for me to use and I dropped his pants. His dick was rock hard already but I ignored that and went straight to do my ''job''. His dick was throbbing the entire duration of the process and until I finished he was already leaking pre cum. I gave him a clean shave and at the end like a good friend I jerked him off so he'd feel more calm. He came all over my hand, his belly and some even got on my face. I bet his dick was hurting, it stayed up hard soo much.

I had sex with a mutual friend’s Dad

I recently went to a birthday party at a random house, I was invited by a girlfriend but I didn’t really know the birthday girl that well. We were running a little late, the party started at 7pm but we didn’t end up arriving until about 9:30pm. By the time we arrived most people were already drunk and a few people were making speeches. I didn’t really know anyone there so I just kind of awkwardly sat in the background. The birthday girl’s Dad got up to make a speech, he was super cute, I assumed he was around 40yo. I couldn’t help but stare at him, he definitely noticed as he looked in my direction and smiled, I smiled back in kind of a panic. My friend had disappeared, she was talking to a few people but returned with a drink, I ended up getting roped into a game a beer pong which definitely got me very tipsy. I wondered inside to use the bathroom, as I was walking through the kitchen, the birthday girls Dad was in there cleaning up. I tried to quickly walk past but he noticed me,

Wife shares my big cock with my college crush

A decade ago, I went skinny dipping with a couple of friends on a warm summer night. I left that evening with the distinct impression that my friend Jane had been captivated with the size of my cock. We have been good friends before and since, but have always been in relationships with other people; nothing has ever happened between us. It is of note, however, that in the last decade she has brought up the size of my penis twice. Once, she mentioned that it was “big” in passing. Another time more recently (and much more publicly) she drunkenly orated about our skinny dipping experience (and my cock’s generous size) in front of a group of friends, including my wife. It was a strange personal detail to have out in the open, but I’d be lying if I said that it wasn’t a bit of a thrill. Luckily, my wife found it hot that Jane had told everyone about my size, saying that it proved that Jane had been fantasizing about my big dick all this time. This past weekend, my wife and I had some fri

My experience with escorts

So I wouldn’t say I do it often but on occasion, hookers are my guilty pleasure. I’ve had some good experiences, some bad ones but the best one was also the best sex I’ve had in my life. This story takes place a few years ago. At the time I was 22 and in college. I had had one experience paying for a blowjob but it was not something I look back at fondly. I decided to try again and was looking through Craigslist personals back when it was still a thing. I started talking to a girl named Kat. We messaged a bit and traded numbers. She was around my age and somewhat new to this. She was a super chill woman and before we even met we would text casually. Meeting people online (especially for sex) can obviously be sketchy and dangerous but she seemed legit. She sent some nudes and damn. She was pretty, a little on the chubbier side and had massive tits. She had a really slutty, bimbo look about her that really turned me on. We had a few sexting sessions and decided to meet up one evening

I got fucked all weekend by my cheating ex’s old friend and his roommate, both are gorgeous firefighters who have flirted with me for months

Guess who’s back? Back again. Tay is back. Tell a friend! So I erased my NSFW account 2 years ago when I was engaged, and with a POS liar who manipulated me. If you know anything about me you know I like my revenge. Well this is a little story about how when I travelled for a concert and stayed with his old friend and crashed with him and his roommate. My body is slowly recovering and I’m pretty sure I still have their cum in me. I posted a photo that I secured tickets to a concert that I’ve been so excited for and one of my ex’s friends Jamal replied that him and his roommate Tristan were going too. He invited my friend and I to stay with them since they had a 3 bedroom place and always hosted friends and family in their guest room when anyone was in town. We pretended like we were just going to book a hotel room but it was a no brainer. Jamal and Tristan were hot, single, muscular firemen. Duh. Bailey and I were going to stay there and fuck them the entire weekend. We really

Here’s how I made a guy feel relaxed during a blowjob. It’s proof as to why women should tell guys their cum tastes good, even if it doesn’t

I find a common anxiety guys have is whether their cum tastes good. So maybe you guys reading can relate, and the girls reading may have had a guy bring this up with them, like I have before. The thing is, if we like you, it’s almost certain we really want to suck your dick - and we’ll let you know. This is an experience I want to share that backs my theory that you should always tell a guy he tastes good. One of the best blowjobs I ever gave nearly didn’t happen due to the guy worrying about the taste of his cum when I told him I swallow. After two dates, I plucked up the courage to invite him to my place for a third. I wanted at least oral before I went to bed that night. During a movie, I outright said, “I really want to give you my mouth.” I could tell he was excited, yet anxious. I reassured him we could get to know each other more and if he declined, it’s more than okay. We went for it and I tied my hair up, with the intention of not coming up properly for air until I’d swal

My girlfriend of four years went from being shy and innocent to daddy's desperate cum slut.

My girlfriend, let's call her Ruby, slowly went from an innocent good girl to a brainless cum bucket. My gf is extremely shy. She didn't have too many friends growing up, was afraid of people and talking, and mostly kept to herself. When I first met her, she was too afraid to talk on the phone, video chat, or even send a selfie. Ruby and I were together for 3 years before we broke up, mostly because she was so incredibly shy. We had only met up a handful of times. She did lose her virginity to me (and it was kinky and amazing) and we had an amazing honeymoon phase where she was really horny, but towards the end she was too shy to even send me selfies. We were sexual with each other maybe once a month or so but it wasn't enough to keep the relationship going. We were broken up for about a month, and Ruby and I started talking again. She was still really shy but opening up a lot more. She sent me a selfie. And was becoming slowly less shy. Then, about a week into us talking, she admit

I fucked a lifeguard while we waited for her boyfriend to pick her up

Hey everyone, this is the first time I am posting here. I found this subreddit a few days ago and finally made an account. I have a few stories I’ve been dying to share with people, and I guess this is the best place to do so. Since I am making a few more posts, I thought I would share a little bit about myself. My dad is Dutch and my mother is Italian, and though they met in Europe, they had me and my siblings when they immigrated to America. I am 6’3 (dutch genetics) and have dirty blonde hair and blue eyes. I recently just finished college a few years ago, and am working a job in tech. I used to play sports growing up, primarily soccer and swimming. I am also a little bit of a nerd and am into fantasy and sci-fi, roleplaying games, and video games. I also enjoy traveling, cooking and other hobbies. Most important to all of this, is I am promiscuous. I enjoy hooking up with different women often. This is something thrilling to me about having multiple partners, as I enjoy having s

Whenever I give head, I ask if a guy’s had his cum swallowed. if the answer’s no, like it was here, I ALWAYS make sure to be his first

I love getting to know a new sexual partner. Admittedly, I’ll ask curious questions that most girls wouldn’t. I’ll be specific, like here, asking how they usually finish from a blowjob. I’d met a guy called Nathan and his favourite way to cum was to blow a huge load over a pair of tits. Sure, it’s common, but I asked outright if he’d had his cum swallowed. Nathan hadn’t experienced it. I genuinely believed him. I asked the erotic questions that has his cock throbbing, like, “so you don’t know how it feels to have your cum cleanly gulped down, huh? Are you sure?” After some playful banter, I asked him how he thought I finished a guy off. I could tell he didn’t want to mention swallowing. I told him my tits would stay dry, winking. I then asked Nathan outright, “have you been good enough to have your cum swallowed?” I told him, “I don’t make a mess and I certainly don’t spit it out. It’ll be too good to waste.” I remember the look on his face, almost looking to the ceiling like, “

(PART 3) My roommate's GF opened my hidden folder and all hell broke loose.

Well, it looks like every dude on Reddit is now obsessed with Mariah. 😂 I appreciate all of the love but PLEASE stop asking for pics of her... This all took place 10 years ago and I've lived a lot of life since then and do NOT have any pics saved of her. While we are still "Facebook friends" I refuse to share pics without her knowing. SO, just enjoy the stories of us fucking around. 😉 ​ ​ To continue where we left off...The next day, I got up to make breakfast. Mariah walked in wearing a t-shirt (no bra) and little shorts, smacked my ass, winked and started making her coffee. "WTF?! You can't do that." I said. "Relax. He's out cold. He got in at like 4am." Mariah responded. Me: "Last night was fucking crazy." Mariah: "So fun!" Me: "Are you good? Like for real?" Mariah: "Oh hell yeah. He never has to know. This is bad though because...Now I just want it even more!" Me: "I know right?! We have to be careful though. I don't want to get tossed to

I let two guys creampie me on the same night at a party

So last night I went this party at this huge airbnb with a pool and like 8 bedrooms. It was packed with people and everyone was druck af. I knew that I wanted to hook up with someone that night and I had spent the day smoking weed and playing with myself imagining what I was gonna let some guy do to me that night. I wore a super short shirt and crop top so short it barely covered my tits and guys were giving me tons of attention. I ended up finding a guy who seemed worthy and after playing some pool and talking for a while he asked me if I wanted to go smoke some weed upstairs. We went into one of the bedrooms and he pulled out a joint. After smoking I got horny as fuck and after getting his cock hard with my mouth and throat I bent over the bed and told him to pls put it in me haha. We were all drunk and had rough sex for like 20 minutes before I was begging him to cum inside of me. (I love creampies) He was happy to oblige and he filled my pussy with cum while calling me a naughty

(PART 2) My roommate's GF opened my hidden folder and all hell broke loose.

WOW. So thankful for the love on my story everyone! I'm excited to share more. Now, let me pick up where I left off... As Mariah wiped her cum-soaked torso off with the towel I had given her, I went in and started the shower in my bathroom. Mariah followed me in but picker her phone up on the way. "Let me just make sure we're good!" She shot John some bullshit text like, "Are you really gonna have to stay there all night?" He confirmed and told her she could just head home and he'd see her the next day. Apparently she texted him back saying she would rather, "Stay and wait for (him) to get home." I'm not gonna lie, there was something so sexy about standing in the shower, waiting for her to join me, while she stood in front of me, completely naked, smelling like my cum, texting her boyfriend. That scene made me start getting hard again right away. With that, she set her phone on the sink, looked up at me and said, "Looks like we have all night!" FUCK she was just per

My roommate's GF opened my hidden folder and all hell broke loose.

So this happened about a decade ago but it's one of those stories that stays with you forever! To be honest, I remember it like it was yesterday. So, I'm gonna tell it with as much detail as possible. Long lead-up here but hopefully you enjoy it! My last year in college I rented a room from a kid (John) whose parents bought a house in our little college town. He was kind of an entitled asshole but not a terrible roommate and he had a SMOKING girlfriend named Mariah. So, I didn't mind living with him at all. Mariah was Lebanese and OMG she was so sexy. Dark skin, long dark hair, big brown eyes, full lips, HUGE tits and nice round ass. The only reason she was with my roommate is because he had locked it up a few years earlier when she was a freshman and he was a sophomore. Man, Mariah was cool as hell too. She was at our house all the time and stayed over pretty often. Every once in a while she would just throw one of John's tee shirts on with no bra underneath after we went swimmin

The time I got my friend off before his date.

I was hanging out with one of my friend’s who for the sake of this story I’ll call Connor. He was getting ready for a date with a girl from Bumble, and she started sending him lewd pictures. I was sitting next to him on the couch as smirking at his phone quickly became side glances as he hid the screen from my view, and attempted to hide an obvious erection. Connor and I have hooked up on and off, but it’s been off recently as he’s looking for something more serious. Maybe it was horrible of me, considering I wasn’t the one who had made his cock hard, but honestly that just made it hotter to me. “She’s letting you know how your night is going to go?” I asked, smirking in his direction before glancing back to what I was doing on my phone. “In. No. Uncertain. Terms.” Connor replied, a stupid grin on his face. It made me wonder if he got the same grin when I had sent him pictures in the past. Selfishly, I hoped he had smiled more at mine. “You gonna need to take care of that before yo

I gave a blowjob to a guy just because he complimented my outfit

I should mention that I don't typically dress in a way that shows off my body. Not that I dress like a nun, but I don't put myself on display either. On this occasion I opted to wear a low cut, tight fitting top with the express purpose of getting attention. It was unusual for my friends to see me dressed this way, and that was the point. I wasn't feeling my best at the time and was hoping the attention might help lift my spirits. Fortunately the constant looks I received did actually make me feel better. I should also mention that I wore this to a group outing with my friends. We were going on a bar crawl for a birthday celebration. There were also a few people with us that I did not know. Friends of friends. One of them was a good looking guy who was paying more attention to me than the others. When we found ourselves somewhat isolated he took the opportunity to compliment my outfit. He also said he liked my style, which is somewhat goth. I decided that I liked him, and I made

Two friends (F24, M28) found my (F24) BBC dildo while visting me. What happened next was unexpected and made me so horny

I can't believe this just happened. I invited two of my friends, let's call them Henry and Steph, to my place for a drink. We had to attend rehearsals at 9PM for a show that we're part of (we do theater). I haven't known Henry and Steph for that long, we met through this theater group that we all signed up for last October. Around January Henry and Steph started dating each other. Henry is a kind and and good-natured guy, he looks very composed and calm at first, but he can adapt to a situation quickly. Pretty average build, but a very attractive stubble, I must say. Steph is a blonde, in every sense. She's much more exuberant, she's the bubbly type of the two. She's very slim and athletic, and has beautiful smiling eyes. Out of all the people in the cast, I'd say they're among the ones that I connected with the most. But still, I wouldn't say we're THAT close. Anyway, today was a long day, and I wanted to relax before attending rehearsals, so naturally I laid down a bit, and pulled

I made my boyfriend cum while our friends whatched.

This happened when I was 22. I had been dating with a guy called James for around a year. I started reading a lot of shit online, and suggested we do a bit more exploration in the bedroom than we had done before. He was hesitant at first, especially once I confessed that I loved the idea of adding more people (both men and women) to the bedroom, but he kept an open mind and we spent a lot of late nights discussing and role playing the wild things we might do with our friends. We were hanging out in his house one night with a couple of friends, drinking and talking. I don’t know what came over me that night, but I was feeling extremely horny. At around 3 am our friends started heading to sleep. When there were only 4 of us awake, I started to tease James in front of our friends. I just couln’t wait any longer. If it was up to me, I would have started to suck his dick. I slid into his lap, straddling him and started peppering gentle kisses down his neck. Surprisingly, they didn’t no