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3,457 stories · Page 59

My Lifelong Friend Became My Fuck Buddy

This happened a couple months ago. My friend Hailey and I have known each other for 20 years. We have always been extremely close. People always thought we were dating in high school and college because of how close we were. The reality was we've never done anything. She is insanely hot. 5'6", about 130 lbs, blonde with D cups and a smaller but nice ass and great legs. I always thought she was hot but I knew I never had a chance so my mind never let me get true feelings for her. We were platonic and I was very fine with it. Anyway, she had won a contest through work and received a free week long cruise for her and a guest. 7 days through the Caribbean, balcony room, all inclusive food and drinks/booze. She was planning on going with her boyfriend but they broke up about a month before the trip. She asked if I wanted to go and I obviously agreed. The first 2 days were normal, we had a blast hanging out and doing things on the ship. The 3rd day was a travel day so we were lounging by

Hardcore with Olenka

Another one of my old fantasy about Olenka. Fantasy each time received more and more details and finally found enough of them to take shape in a single story. So... I, Fedor, Peter, Andrey and Matvey waited for the moment when you worked at the car wash in the afternoon and were alone for 3 hours. This was enough to carry out the plan. I was dressed simply in summer, T-shirt, jeans, sneakers and a mask. I knew you'd still recognize me, but it was protection from security cameras. The guys were dressed in riot police uniforms. I went in first, went through the hall where they wash cars, there was no one in it, put on a mask and went further to the waiting room for customers and the administrator. That administrator was you, Olenka. Slender, very beautiful blonde, with long curly hair, with brown luxurious eyes. Your forms excited me very much and forced me to fantasize regularly on your topic during masturbation. And, most importantly, these forms and your sweet, very feminine face, l

28 Sleeping with my boyfriend inside of me

Other than during that time of the month. Each night when we are ready to sleep, I have my boyfriend penetrate me. If it’s a cooler night I’ll sleep on him lying in the cowgirl position, but most nights I’ll be the little spoon with him penetrating me from the big spoon position. I may only be ‘wet enough’ to penetrate when he puts it in, but there’s no other time or action that makes me grool as much as it does throughout the night when he’s inside of me. I can wake up randomly and we both be absolutely covered in my fluids that have leaked out. Often lying in the wet patch, but I don’t care! Mentally I just feel so connected to him, almost like he’s the plug and I’m the port, transferring all of his love through himself into me every night! That’s not even to mention that my wet dream orgasms, with him inside me, have increased ten fold! I maybe had two or three sleeping orgasms from wet dreams in my whole life before this. Now I have one or two per month! His penis head stays in m

I let a of gamers watch me suck their friends dick

When I was in college I worked at a cyber café. Sometimes we would have lock-ins for private parties that would last all night. My boss would let them bring alcohol if they were old enough as long as they didn't get too rowdy. One night I was working one of them and my boss had an emergency that he had to attend to. He asked me if I was comfortable being alone with the 6 guys who were celebrating their friends birthday. They seemed chill so I said it was fine. I ended up drinking with them and playing games most the night. One of the guys asked me if I would do something special for his friend because he thought I was hot and had picked this place for his bday because I worked there. I had discovered recently that one of my kinks was to be watched so the idea of doing stuff with him in front of his friends was turning me on. I suggested that we play some truth or dare to break the ice. After a few rounds of easy stuff I was finally dared to make out with the bday b

24 I helped my virgin friend blow the biggest load ever

Dear Reddit, I’ve been home alone all week this week and have made the absolute best of it! I wanted to talk about my adventure on Tuesday! I invited one of my friends over that’s a virgin. He’s 21 an just a really shy sweetheart. He’s very attractive but I think he struggles to deal the deal with girls just because of shyness. Oh well, I have a thing for virgin guys so their loss and my win, lol. I’ve known him for like 10 years and nothing has really happened over the years until Tuesday! I invited him over to watch Netflix and have a sleepover. We were having some wine and taking some bong rips while watching Euphoria while chillin in our pajamas. For those of you that don’t know Euphoria has a bunch of steamy sex scenes. I was getting fairly turned on watching it and looked over at him. I looked over at his crotch and noticed his cock had snuck out of his pajamas slit and was rock hard. I don’t think he noticed, probably because he was too high, lol. I figured I’d try to make

The camping trip (an unexpected naked week with friends) Part 2

I threw my trunks on as fast as I could. I was still in disbelief with the events I was just a part of. Confused about why it had happened and why my wife was ok with it. I hurried after Chrissy and my wife. As I caught up with them I admired their beautiful asses in their bikinis. Chrissy's was half crawling up her ass, I am guessing because of the hurry when she was putting it on and not really caring. The walk to the pool was about 5 minutes and the two of them made idle chitchat like nothing had happened back in the tent. As we rounded the corner just before the pool John and Katie were coming toward us. "Wow" was all I said when I saw them. Both John and Katie were completely naked. My wife let out a surprised but happy squeal and Chrissywas looking at John's hard cock with a lustful grin. Katie's tits were standing at attention bit they looked so inviting with their small dark nipples and hot loop piercings. She had a small landing strip that matched her dark brown hair but othe

(25F) Concert Buddy

I(F) was 19 or 20 at the time, pretty fresh out of high school, and I went to a Jimmy Eat World concert with a bunch of co-workers. It was a great time. Between sets, before the main act, I got to talking with this older guy, like 42 y/o or so; I was 5'4”ish so he must've been about 6". We talked about our favorite songs, what we hoped they would play, and flirted a bit. I specifically mentioned I wanted them to play Blister, but he said that song was too old and not classic/popular enough. He took my beer cup and I walked back to my co-workers. During the concert, they actually did play Blister and when I realized it, I looked back at him and gave him an "I-told-you-so" look. During the song he started dancing with me and I let him put his hands on my hips and we grinded a little bit. His hands were big and smooth, and they gripped my ass cheeks a few times. I felt his fingers dig in a little bit to feel the warm of my pussy. He sucked my neck a little bit and that instantly made me

His mom walked in on her son blowing his second load on my face

Peering through my sunglasses at the neighborhood pool, I tucked a strand of my hair behind an ear before flipping over onto my stomach on my pool chair. It was summer, and I was back home with my parents. I saw Sean’s shadow before he spoke. "Hey, Taylor." Sean said, trying to act cool as his buds watched him snickering. It didn’t take much to know exactly what was happening. They had dared their friend to come talk to me, and he was being a man about it. Ugh, boys. "Hey, Sean! Long time no see." I smiled, sitting up and watched Sean’s eyes go directly to my new boobs in my tight bikini top. "What's up?" Sean was a couple years younger than me and had just graduated high school. I know he was an athlete of some kind, but couldn’t remember the sport. He was cute, and I was prepared to make him look like a freaking stud in front of his leering friends. "I was wondering if you had anything going on tonight?" Sean asked. I paused for effect, "You m

I dominate you

For some time after the threesome, I was bursting with conflicting emotions. Jealousy came in waves, suddenly throwing me from "I legally fucked my girlfriend's hot friend in every way" to "Oksana cheated on me right in front of me." I did not want to quarrel and I withdrew into myself. Previously, Oksana would have found out what was the matter (by all means accompanying the interrogation with torture), but now I saw that she was also worried and was afraid to worsen the situation. This really upset me: I thought that if she felt guilty, then my jealousy was pointing in the right direction. Does she cheat on me regularly? Does she have a relationship with Dasha? Maybe she prefers women in general? This went on for several painful days, until Oksana decided to speak about it first: "I... owe you an apology," she said, fidgeting nervously with an unbuttoned shirt button. - For what? I asked sadly. - Then ... With Dasha ... It seems to me that I have somewhat crossed the line.

I 20F got drunk and ruined a good friendship by sucking dick

So throwaway for obvious reasons me \[F22\] and a guy I’ve been friends with for 12 years were just hanging out and having a few drinks this past weekend. Anyway I had friend-zoned him long ago and didn’t think we’d ever do anything like this but he mentioned he was in a dry spell. To cut a long story short he kept kind of hinting masked as a joke that I could fuck him or suck his cock. After a few hours of him mentioning it every now and then I found myself on my knees sucking his dick. Thing is though he started saying stuff like he knew I’d do stuff like this. He’d been waiting for years etc He called me mean names, which I’m fine with I kinda liked it. But now it feels weird when I see him, like the friendship isn’t the same.

I (34F) Just got back from a Gloryhole!

A few months ago a friend of mine and I opened a gloryhole at a bar that she owns. Every Saturday I go there and service countless cocks while she serves drinks and steers men my way. It's honestly the highlight of my week and I just got home. I'm still cum drunk (and normal drunk lol) and I can't stop thinking about it. There's just something so hot about making strangers cum wherever I want. I was there for the past 4 hours and I never took a break. There's nothing more exciting than seeing money fall though a hole and then a juicy cock. I must have made at least 30 men cum while I was there. They came all over my face, tits and ass and I took 9 creampies. I ended up making over $800. I still haven't cleaned myself up, I'm laying here covered in cum fucking myself. My son is at a friend's house so I have all night.

My First Trans Experience

Before I get into the actual experience, I’ll give you some backstory on how we got there. Growing up, I had a best friend named Brian who was also my neighbor. We met when we were 5 or 6 and both also ended up having older brothers who became friends through sports. So basically, we were together all the time, whether it was hanging out together at one of our houses or at sporting events, either our brothers’ or our own. We were essentially inseparable. Brian’s brother was an exceptional hockey player, and even though we all played in some capacity growing up, he was miles better than anybody else in the leagues. Because of that, Brian and his family moved away when we were both 11 years old so he could pursue sports. It was tough when he moved but we still stayed in contact somewhat. This is a few years ago now so social media was still relatively new. We became friends on the various platforms and stayed in contact that way but eventually lost most contact when we entered high sc

Me and my housemate masturbated together, and then she left me a present

At this point in my life I lived in a house with 4 people, me, another guy, and two girls. Just before we’d moved in I’d been having a friends with benefits situation with one of the girls that got really messy and almost caused us to not go ahead with the house (and leave us with far too little time to get somewhere). Because of this there was a bit of a rule that everyone would just stay friends and not start fucking. I went along with it because I really needed somewhere to live, but it just made the idea of it so much hotter. The other girl I lived with was called Lucy. I’d known Lucy a few years and had always thought she was incredibly hot but nothing had ever happened. She was a little less petit than the kind I normally go for, with a slightly stockier build with a larger chest and ass to match. She had an extremely pretty face. Her Spanish father and Greek mother had given her dark hair, gorgeous brown eyes, and a very cute accent to match. I was coming in one Sunday morning

18 years ago me (m20) fucked my sister (f24) for 2 years.

Ive been sharing some of my sexventures with yall. Ive had a varied sex life for sure. Im 38 now married with kids but my 20's were a wild ride. So im going to give the details before the actual deed. Im 6'4 brown light bown skin, brown eyes. In my 20s i had a swimmers body. My dick is 6.5 inches and about the medium size red bull can thick. My sister was/is 5'11 light brown skin, brown eyes with a softball player body. Like thick muscular. Her tits are large like personal watermelon size, they are shapely very little sag but squishy. Her nipples are like those ones they call ghost nipples. They are perfect tits in my opionon. She has a bubble but and thick thighs. Most guys rate her a 9/10. Anyhow my mom is a single mom. I lived still at home with her until i was 22. At the time me, my mom and 2 younger sisters lived there. One 2 years younger other 4 years younger. My older sister had moved out and had a good job. We are a close family we often got together for dinner or BBQs

young bride

Natalya Ivanovna refused to believe what was happening. The smell of incense and incense made my head spin. From the mournful monotonous mumbling of the priest, he pounded in his temples. Among the hubbub of the crowd that filled the church, she clearly distinguished the sobs of her mother. What was happening was like a fog through the veil of a veil. Afraid to turn her head, she felt the imposing figure of her fiancé to her right with her skin. Tall, of outstanding heroic build, in a full dress uniform, in orders, with a proud posture, a lush gray mustache and a bald head shining in the light of numerous candles, next to the fragile short 18-year-old Tatochka, as she was affectionately called by her family, her betrothed stood proudly and majestically - Polikarp Semenovich Stolbov, retired general, 57 years old, rich widower. Natalya Ivanovna saw him for the second time in her life. She had first glimpsed him a month ago. He was present at the family dinner, talking only to the girl

I (24f) was a very bad girl and got fucked by the biggest cock I've ever had yesterday

Sorry for the length. But this was wild. I'm going to get into a lot of trouble for what happened yesterday, I'm actually really nervous about it. So nervous I haven't told my owner yet, but I'll tell all of you for now. Yesterday my owner and I went to what was essentially a sex party. He was invited by one of his associates in the lifestyle and since we've never done anything like that together before, he agreed. He thought it would be fun. I was nervous, but very very excited. I wore a cute little sundress, no underwear at all, and my collar. I did't really know what to expect, but I was eager to find out. My owner has been to things like this in the past and told me that it was going to be intense, but he expects me to follow his orders and the rules. For ease of simplicity the rules are basically I'm not allowed to fuck unless he tells me otherwise lol. Which I was fine with. The party was at someone's summer house. It was a private area, surrounded by trees and no other hous

Made me lick

The year before last, in the month of November, I don't remember exactly... But the events are still fresh, as if it were a week ago. My wife was in the hospital for preservation, and I was alone at home, and toiled from the point, thinking about what to do with myself. But then I got a call from my wife's niece, Katerina. We have known each other for a long time, and we had a very good relationship. Well followed by a typical conversation. — Hello, Vova. This is Katya, how are you, what are you doing? Hi, I don't do anything. Tanya is in the hospital, I miss being at home. - And I'm bored ... If you want to come, it will be more fun together. - Come, otherwise I'm dying of anguish ... - All right, wait. I will soon. And gave up. In order to pass the time before arrival, Katerina decided to clean up a bit, put things in order in the apartment. An hour later, the intercom rang, Katya arrived ... - Hi Vov. - Hello Katyusha, come on in. I helped Katya take off her oute

5 Second Rule

I (M18) Was partying in Germany, I live in the Netherlands. I was talking to this German girl, ( We both didn't speak each others language). We started to flirt and I asked her to come to my hotelroom. She agreed and we walked toward my hotelroom. We started making out and I removed her clothes. She gave me head and at one point she want to sit on my face. So i started eating her out while she sat on my face. But i could not breathe so i moved a bit to not die lol. With that little movement she fell of the bed. Then she said with a German accent ''5 Second Rule'' (Like the rule if you drop food and pick it up within 5 seconds its okay to eat it.) So i continued to eat her out. ​ I posted another story! if you want more of this

Watching my buddy fuck my girlfriend in the back seat. Rear view mirror

My best friend Denny agreed to to give me and my girlfriend Annie a ride to Portland to pick up a car I had bought . Denny was two years older than Annie and I , we both had our 18th birthdays that July. He was a tall good looking guy , rugged and strong. His biggest problem was girls , he was super shy and awkward when he was around attractive ones . That's why he didn't have a girlfriend or even a date with one that we knew of . This drove my girlfriend absolutely crazy . Annie was the first nymphomaniac I had ever met . She was bi sexual since puberty , and introduced me to threesomes , foursomes and she was an avid exhabitionist . Absolutely all the qualities I never dreamed I would find and all in one woman . She was pretty , and had the body of a dancer , as in strip club dancer . Annie had tried to set Denny up with a couple of her slutty girlfriends , hopefully one of them could get into his pants but no luck ..She asked if I would tell him that her and I liked having an

Receptionist (F24) at massage parlor call me (M36) an anaconda.

I’m on a business trip. Been so horny all week long. Decided to visit a local massage parlor that is open for negotiations. I arrived and there were 3 “therapists” to choose from. But I liked the receptionist better so I ask if she’s available. She’s Asian, petite and quite cute. She said yes but there will be extra since she’s not “working”. I said I didn’t mind. I paid the fee and she led to a room. She asked me to strip and left the room. I did as she asked but put a tower around my junk. I was already nursing a semi by then. She came back into the room and stripped and said, “You’re not here for a massage, are you?” I said, she’s right. She asked how much can you pay, and I low balled her. When we agreed on a price she pulled my boxer down and immediately step back, “omfg, you’re an anaconda!” I was pleased with her compliment. I always thought I was above average but this was really boosting my ego. I didn’t think I was that big. I suspected she said that to any guy she fuc