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862 stories · Page 38

Cheering up my girlfriend's friend after a breakup (Part I)

My girlfriend, Lisa, had a close friend Val, who had had a string of short relationships and she was really down about it. The latest breakup really pissed her off and Lisa decided to take her out with a couple of their other friends for a girl's night to help her blow off some steam and maybe find a random hookup. I had to hold my jaw up when Val showed up at our place in a tight little blue mini dress. We always had great flirtatious banter but it never seemed serious as I was very happy with Lisa and Val always had multiple guys chasing after her. She had to know how sexy I thought she was by some of the looks I gave her though. Both her and Lisa were about 5'2", but complete contrasts other than that. Lisa is slim, dark haired and dark eyed, with an amazing heart shaped bum and perky b-cups. Val has light blonde hair with striking blue eyes, curvy hips and full d-cup breasts. The pair of them together were sure to draw some eyeballs in the local clubs. I told them how fantastic

You'll never believe what happened when my roommate caught me masturbating...

My old roommate, John, had been out shopping, leaving me alone in the apartment. I had decided to indulge in my favorite pastime, watching erotic videos and pleasuring myself. Just as one of the performers on screen began to pleasure her partner, I heard the telltale sound of the front door opening. **I froze.** My fingers still buried deep inside of me as I turned to see John standing in the doorway. Our gazes met, and I couldn't help but feel a rush of embarrassment and arousal at being caught in such a vulnerable state. We had known each other for years, since high school, and while we were close, we had never been romantically involved. As the silence stretched between us, I scrambled to cover myself with a nearby blanket. John simply stood there, one eyebrow raised in amusement as I stuttered and stammered, trying to come up with an explanation. "Save it," he said finally, his eyes sparkling with humor as he placed his shopping bags on the kitchen counter. "Don't mind me, I'

A ew years ago I challenged myself to do something crazy with this guy...

Hello, my name is Ivy and I love unique challenges. Here's one that happened just a few years ago. I was a true submissive, with a deep craving for oral pleasure. Giving blowjobs was my absolute favorite thing to do, and even when I was alone, I often had a toy in my mouth as I pleasured myself. Over the years, I had become quite skilled in this particular art. One night, I went out with some friends to a local bar. We were all a bit tipsy and as always, our conversations turned to a more risqué nature. **One of the guys in our group, a friend of a friend, claimed he had never had an orgasm from oral sex.** I found this hard to believe, given that he was in his late twenties, but I made a mental note of it all the same. The next day, I added him on ig and we started chatting online a bit... Eventually, I asked him if it was true that he had never had an orgasm from oral sex. *Like, really?* He confirmed that it was. I relished a good challenge and this one seem

We tried swinging while on vacations

She was really, really attractive. We had discussed opening our relationship before. But the truth is that neither of us really wanted the other to go "looking around." We deeply loved each together and were committed to one another. We had been dating since high school, for instance. He was my first, and my only one, and same for him. But that woman was simply gorgeous. I had had that kind of fantasy before. To watch your partner have sex with someone else. Be a third party. Just... observe. Watch him have some fun, watch him do with her what he only did with you. It was all those feeling, I suppose. To be there and watch it happen. Live, under your eyes. It was terribly, terribly arousing. And if Josh had one flaw - and he didn't have many - it was that he was not into domination at all. Sometimes, I fantasized about it. A coworker from work, with big shoulders and big hands, pinning me down, making me do... stuff. I don't even know how to describe it. I d

Skinny dipping with a friend led to us finally hooking up!

Last summer one of my(f) male friends (lets call him Tom) and I did a little trip round Scotland together and decided to go skinny dipping at a secluded loch. At this point we were just friends and had never hooked up before, but there had always been a lot of sexual tension between us and I think we both were hoping this trip could lead to more. Tom was more worried about the cold water but I just went straight for it, walking towards the loch, pulling off my clothing as I went. From where Tom stood still hesitating he would have seen the pale skin of my back revealed as I peeled off my top and let it drop to the peppled beach. Next, right at the waters edge, I let my pants drop, exposing my ass to him. I can’t deny I got a thrill knowing he was seeing me naked and thinking his cock might be starting to twitch inside his jeans at the show I was giving him. Looking over my shoulder I glanced back to him. “You joining me then?” He didn’t need telling twice. In a mom

My husband wants to fuck my best friend ..... and I'm OK with it!

Unknowingly to him at the time, my husband's photo folder on his phone syncs to our family computer. One day I was working at the computer and was notified to his screenshot folder updating. I clicked on it, and to my surprise were several screenshots from my best friends IG page. Bikini photos, tight clothes, cleavage etc. Now I'm the first to admit, she is really hot (similar height to me, 5ft2" but with bigger boobs and a better bum due her to working out. I'm 100% hetero but I can appreciate her!) and the thought of him checking her out turned me on a little. I kept it to myself for months but whenever we went to her and her husbands place, I always got a little kick out of watching him chat to her. His mannerisms were different, it was so obvious he was into her! Then one night we were in bed kissing, both getting turned on and I mentioned it to him. He got really embarrassed and apologised to me. I pretended to be mad at first, then I played along. He told me he finds her hot

y girlriend blew me in the bed next to our sorta-sleeping friends (with their consent)

This is one of my favorite memories. My girlfriend Leah and I went on a one day trip to see a band in Cleveland with our friends Josh and Katie. We split a hotel room to keep it affordable, and had a really great time. The show ended around 11, so we wandered and had some drinks. Nothing too wild as we knew we had a 4 hour drive in the morning. My girlfriend loves to “blow me to sleep” she calls it her goodnight kisses. We typically have sex in the mornings, and almost every single night she generously deepthroats me into a sleepy oblivion. Some nights she will just lay her head in my lap and casually suck my dick for what seems like hours. We’ve fallen asleep several times with my cock in her mouth. I have a mouth obsessed soon-to-be fiancé who is generous and addicted to sucking me on a nightly. She legitimately insists I do not return the notion, either. It’s a one way street for her, and I love it (of course) After the drinks we all piled into our hotel and Leah and I were ma

I think I took some Christmas night flirting a little too far but I want more from him

Gotta use the throwaway for this! (First post so im sorry if this isnt great!) My brother in laws cousin often joins our family Christmas activities, which is great, the more the merrier and all. I always have a great conversation with Alex (let's call him Alex) whenever I see him. He is pretty quiet, funny, but definitely not particularly forward. I think he is gorgeous as well, but I have always been in a relationship and I know that he is quite religious, so it's never gone past a cheeky joke etc. Til' last night. This is my first Christmas single in almost a decade. I'm doing okay but it's hit a little harder over the Holidays. Last night I spent Christmas with my sister, brother in law and both sides of their family. Alex was there, besides the younger kids/teens we are the only single ones. So my sister ensured we were sitting together which was great. We chatted almost the whole day, I don't think until after dessert I noticed a button on my dress had come open (I am pretty

I sexted with the wrong guy for weeks without knowing. Now we might meet up.

I was hanging out with some work friends a couple of weeks ago and one of our old coworkers who I have always had a crush on showed up. We used to flirt but nothing ever happened because at the time my marriage was closed. Normally he was kind of shy but this night he had a few drinks and we started getting a little grindy on the dance floor. A couple of my coworkers noticed and I didn't want to cause a stir of work gossip (they don't know my marriage is open now) so I told him I had to go but that we should swap numbers. He had left his phone in the car so he gave me his number and I went home. As I was lying in bed I sent him a text letting him know that I was having trouble sleeping because I couldn't stop thinking about him rubbing up against me and that I wished he was there. He responded quickly and after some back and forth dirty talk I sent him a picture showing him how wet he was making me. He sent me a video of him stroking his cock and I remember being surprised that his st

Jamaican resort gives new meaning to all inclusive

My wife and I went to Jamaica for our wedding anniversary. We stayed at an all inclusive resort in Negril, so was a long ride from the airport. When we arrived at the resort, we we’re greeted, given a glass of champagne and told someone would take us to our unit. Soon someone came and directed us to follow to our ocean view cottage. The resort was beautiful, many activities, great food , drinks and entertainment. On out second day the concierge asked if we scheduled our couples massage yet ? We said we didn’t know anything about the massage. She said that it was part of our anniversary package we booked. So she set us up for our massage the next days. The building that housed the massage studio was down a path through the beautiful foliage. When we found the building, a sign on the door said if no one was there, take a seat, enjoy the scenery and someone would be there shortly. It was very quiet, and the foliage was thick, but beautiful. We heard voices coming down the p

My husband made me have an adult conversation about my thoughts and feelings… and then he proceeded to fuck me silly and come on my face

I am… not great with my feelings. I have a tendency to implode and suffer in silence. Meanwhile, my fucking husband is the most well-adjusted and emotionally stable person I know. It’s very annoying. The hardest part of our marriage, is admittedly my inability to talk about feelings. At first I got away with it, but he has a habit of forcing me into healthy routines that require examining my emotions. *Fucking asshole, right?* My husband fucking LOVES Christmas. He’s obsessed with the holiday and loves all things festive. The man fucking likes caroling like a psychopath. I don’t hate Christmas, but I don’t really get it. I didn’t celebrate when I was a kid and I feel like an alien when everyone talks about traditions. I get the basic stuff, but I don’t have warm memories others associate with it. *Ironically, my husband is Jewish. I am not.* For Christmas, he stuffed a stocking with the most thoughtful Viola-like presents in the world. I stuffed his with lingerie. He made

I 42 just had sex with my 19yo virgin coworker in a hotel room as a Christmas present.

The next morning after our fun in the car, he almost immediately messaged me asking if I was serious about a follow up with a condom. Seriously, it was 7:42 in the morning. It was cute and adorable, and I told him that I was. I wanted to be his little Christmas present this year. One that he’ll always remember. He confessed he was still a virgin, and wanted to know if that was okay. Again, cute and adorable. I told him it was, and that since I had my tubes tied years ago that if he will go to the student clinic on campus and get an STD test, we can forgo the condoms. (Ladies, if you are reading this, don’t trust everyone that says they are ‘virgins’ or are ‘clean.’ Better to be safe than sorry!) I pulled out all the stops for this. The mercantile we work at is in the downtown portion of our city, and there’s a pretty nice hotel a couple blocks down. Rented a room for the two of us, got freshly waxed all over, made dinner reservations, and picked out a little lingerie for him to enjo

The Bridesmaid

I recently found myself at a wedding where I knew few people. It wasn't somewhere I was thrilled to be; just one of those events you need to attend. Nonetheless, I found a seat at the ceremony, nowhere near the front, but not quite in the back. As more people filed in, a group of what I can only describe as "finance bros" surrounded me - a few on my right, more in front. I've dealt with their type often enough and made pleasantries until the ceremony started. And I think they had a comment about every bridesmaid - "looks like a milf", "wonder if she's single", and "great tits on her". They were right, one in particular had great tits, and the snug bridesmaid dresses did well to attenuate them, which just a hint of cleavage to make a man's mind wander. Fast forward to cocktail hour, and I find myself next to "great tits". I tell her she looks great, and we chat about the bride and groom. Maybe it was the alcohol flowing, but I mention to her that the finance bros had comments o

I let my best friend’s father fuck me in an Applebee’s parking lot

This happened my sophomore year in college. It had been a month and a half since I saw Mr Jacobs. The last time I saw him he was licking my pussy and I sent him home with my panties, stuffing them in his pants as he walked out the door with my roommate. The new semester was starting and I was wondering what he had been thinking about for the past 6 weeks. Did he try to forget about me or was he jerking off with my panties every night? I got to the dorm and my roommate and her parents were already there getting stuff set up. My roommate jumped up and gave me a big hug and I pleasantly waved at her parents. “Hi Mr and Mrs Jacobs, good to see you, hope you had a great holiday and got some great gifts.” They both waved back and Mrs Jacobs told me what a wonderful holiday they had had. “Hi Katie” Mr Jacobs said, and he blushed and turned away. I proceeded to starting setting up my side of the room. I wore a jean skirt that day, hoping I would have a chance to tease Mr Jacobs. I didn’t w

My friend caught her husband jerking off to me and now she seems obsessed with me

*Readers note: This happened in September of this year but there has been an update since then which I also included below.* Occasionally I will send nudes to one of my girlfriends so I can get a second opinion on poses, outfits, etc. She used to be a model and has a really good eye. Last night she told me that a few weeks ago she had dropped by the house unexpectedly in the middle of the day and caught her husband jerking off to my pictures. He had seen them on her phone one day and then secretly sent them to himself. When she told me this detail I wasn't really bothered (kind of flattered actually) but I kept that to myself. They got in a huge fight. After a week things mostly went back to normal except she couldn't get the image of him stroking his cock to me out of her head. Then a funny thing happened, she started to get turned on by it. She was touching herself and reliving the moment. She started imagining him fucking me while she watched. The next day she handed him a picture

y Girlfriend let me cum down her riend's throat

I have been seeing this woman for about a year now and it has been going, frankly, amazing. I don't have the best track record when it comes to romantic relationships, and this girl is the far-and-away the best yet, so I have been laser-focused on not fucking things up. This is a bit long so I'll spoil it now, might be amazing, might've fucked it up. Her name is Rebecca, she's smarter than me (got her PhD), great in bed, to my friends I'd describe her as gorgeous, for just giving you an image here, honestly think 'gram model. Long legs with the perfect ass, she's in great shape which motivates me to be in great shape (or work back towards it at least). Perfect handful breasts, a body type any dress looks good on. And even before House of the Dragon she was rocking the Targaryen hair. Don't want to get too into what we each do but we live in NYC, early thirties, we're both doing pretty well. In that magical stage of the relationship where we both have our own apartments but rarely s

Licking my Bf's cum out of another girl

So me, my bf, and one of my best friends ended up drinking a bunch of wine at my place the other night. And we ended up tipsy and horny and somehow before i knew it we were both sucking my bfs cock and making out with it in our mouth. It was so hot and we both got horny as fuck and I knew I was gonna get to watch him fuck my best friend. I ended up laying on top of her making out with her while he traded off back and forth between our pussies. It was hot as fuck she would rub my clit while he fucked me and I would touch hers while he fucked her. When I could feel that he was about to cum i pulled his cock out of me and shoved it into my friend and jerked his cum into her pussy it was so hot. Right after I felt a surge of jealousy tho and I dont usually eat pussy but I felt the need to lick his cum out of her so I did. I kept licking her until she was cumming in my mouth and at some point my bf started fucking me again from behind. It was all good tho cause he came in me t

My friends walked in on me riding my boyfriend but we didn't stop

It was Spring Break and we had rented a beach house with a group of 12 friends. There was only a couple of bedrooms but one of the rooms was huge and slept 8 people. It had multiple bunk beds and two queen beds. My boyfriend and I got one of the queen beds. One of the nights we had a huge bonfire on the beach. Everyone seemed to be really occupied and drunk so we figured it would be a good time to sneak back to the house and fuck. When we got to the room we realized that someone was in the room passed out drunk. They didn't seem like they were waking up anytime soon so we killed the lights and started making out. After some fingering, kissing, and dick sucking I straddled him and slid him all the way in. At one point the sleeping drunk friend started to stir so we tried to keep it down a bit. My boyfriend put his hand over my mouth a few times to muffle my moans. We started to hear drunk voices in the living room but we were both really close to cumming and I assumed that they w

there's nothing turning me on more than guys cumming

My inner feminist is screaming with rage, but I managed to lock her away... for now. Seriously tho, the moment I discovered my sexuality was the moment I discovered how much I love cum. And how much I love guys to cum. All the porn I consume (if any) is single guys jerking off. Sometimes even two guys at once (and yeah I know that they probably wouldn't be interested in me). The more guys, the more dicks, the more cum, the happier I am. It's that simple. And even during sex with a partner, it's all I am focusing on. I just want him to cum. Because of me. To see him helpless, whimpering sweet things like "Fuck", "Shit", "Babe, I'm gonna cum", "You're making me cum", "I can't hold it in any longer" is the biggest compliment to me. His orgasm my accomplishment. His leftovers in my pussy my trophy. Just thinking about it makes me wet already. Maybe it's kind of a power play. Although I am usually more of a sub, I discovered that taking care of a guy in this way makes me feel powerful. H

round 2 of my neighbor watching me undress (MILF)

Last night I saw my neighbor peeking into my window again after I got out of the shower. I knew he was there, so I decided to give him an extra show. I teasingly bent over and accidentally "dropped" my panties, giving him a full view of my bare body. I could feel his eyes on me and for a moment, I allowed myself to bask in the pleasure of being watched. I could feel my cheeks getting flushed and my heart racing as I slowly stood back up and put my panties back on. It was a naughty moment, but one that I definitely enjoyed. I honestly think next time I'm going to have to find a way to give him a full show. I wanted to tonight, but I kind of chickened out. How should I get his attention tomorrow and start to touch myself in a way that seems natural?