My ex had a cuckold fetish and was obsessed with watching porn about it. I didn’t get the appeal and really didn’t want to sleep with anyone other than my boyfriend, but over time he convinced me to try it. After a few weeks of searching we found a guy on Reddit who we both felt comfortable with. He was almost twice my age but very attractive and almost had a body builder like physique. My ex was very shy and scrawny and he liked that this guy was so different than him. I won’t lie, it intrigued me too.
I’ll skip ahead to after we met and went back to a hotel room together. My boyfriend didn’t want to be very involved and wanted to watch and masturbate while me and our new friend had fun. As soon as I pulled his pants down I was intimidated by his size. My ex wasn’t tiny but this guy had a monster in comparison. I couldn’t help but get excited and fawn over it a bit. The guy jokingly said something like “you’re not used to a real cock like this are you baby?” and I let slip out “I’m r... continue reading
Mutual masturbation with coworker
Sara has been working with me for about 6 months for now. Our jobs are remote, but it does require some travel to the HQ occasionally so we’ve met in person a few times already. We work with a large team, but the two of us definitely work closest with each other. We’ve shared many hours on zoom together and have gotten fairly close to each other.
Each time we travel to HQ we make a point of getting drinks and dinners as a group. It’s always a good time. We’ve shared some “looks” and “moments” across the dinner tables, but never acted on it. After all, we don’t want things to get awkward between the two of us. I want to make sure we don’t jeopardize our jobs and dynamics to be productive as a team. But the sexual tension has been growing noticeably over time.
Another work trip back to HQ and I get in late Monday night at the hotel and see a text message from Sara.
\[Sara\] “How was your flight? Did you get in the hotel ok?”
\[Me\] “Yeah, long flight but not too bad. Just getting set... continue reading
Made my therapist beg to cum
It’s been a while since I’ve written, but I just wanted to share an experience from last week. A few years ago I had a therapist named Noel. I was her client for about 3 months until I ended up moving out of the state. She always dressed incredibly formal at our appointments, and things were strictly business oriented. I was her client, she was my therapist.
When I started seeing her, I remember thinking immediately that she was cute, around my age— mid 20’s. She always kept her hair up in a tight bun, and the only indication that she wasn’t a total square was her small septum ring. Really she was a wonderful therapist and I wish I could have kept seeing her.
Last week I did. I was back in town, visiting family, and chatting with an old friend at a bar. I excused myself to the restroom and as I was patting my cheeks with blush, there was Noel washing her hands in the mirror.
“Noel?” I said, shocked. She looked over.
She was just as pretty as I remembered, but absolutely f... continue reading
Hi! I’m Evie! A small disclaimer: I am actually 43 currently, but wanted to use the age I was when this happened.
It all started at a holiday party my best friend, Olivia, was having at her place a couple years ago. Olivia and I went to college together, were roommates for the first couple years before I got married, and have been in the same city our entire adult lives. We are two peas in a pod! Her home is quite lovely, and large enough to host fairly large get-togethers. This one is no exception with a catered dinner, open bar, and plenty of room to mingle and talk amongst the small sea of people.
We also had kids around the same time - two for her and three for me - so they’re there too, all home from university for a few weeks before spring semester starts. Her youngest son is a track star at a college close by while her oldest, Kevin, has always been stupidly smart. Graduated high school early, already has a bachelor’s degree, and will have a master’s degree after the next se... continue reading
Emma the church girl, y video penpal
This is another story that I admit is not as wild as some of my other posts but I wanted to relive it so I did my best to capture the essence of the experience because it is one of my fondest memories (holy run on sentence, Batman!).
In my late teens and early 20's I worked a lot of retail jobs. I was working in the mall at a store that no longer exists when I met Emma. Emma was from the midwest and had moved to my area when she was in high school. She was involved in theater in college and loved to sing. As a creative type myself, I always felt a kinship with her.
Emma was average height and skinny with long, straight brown hair and glasses. Her boobs were small, definitely A cups but she was fit and had a cute little butt. She never really wore revealing clothes but I remember one time she came to work after some kind of event and she was dressed up and wearing pantyhose. I remember thinking for the first time I understand the appeal of legs as a sexual object.
Emma spent her form... continue reading
Living out my bisexual dreams in my boyfriend's pool
This all happened a few summers ago, but I've been thinking a lot of it recently. I thought I'd share.
Early into my relationship with my boyfriend (let's call him M), I confessed to him that I might be bisexual. Like any good boyfriend, he was gracious to offer me the chance to explore my sexuality while we were together. He offered a one-way open relationship for me to explore with women. As nice of an offer as that was, I knew one of his bucket list items was to have an FFM threesome. I thought the solution was clear, I told him that I was too shy to explore alone and that I would want his support. We agreed to a threesome.
We didn't know how to find a bisexual, F, our age who would be interested in a threesome. However, one day, M reconnected with an old high school friend of his (lets call her K). While they were catching up, she let slip that she came out as bi. M, in keeping up with the conversation, admitted that I was bicurious. He explained that I wasn't ready to put a la... continue reading
First time with daughter's best friend
Hi long time reader here but never had the thought to write up some of my past on here until now. Honestly a bit worried I wont stack up to how well some of you write! If this post gets a lot of attention I may even write up some more! A little about me before we start, mid 40s dad of one. Best daughter I could have wished for! Mostly raised her myself in a household where talking about sex was not taboo at all. That is kind of important for the story. Anyways I will start with no more delay. Everyone in this story is 18+
Me, my daughter (Chloe) and her best friend (Zara) would frequently go to conventions and when my daughter left for college it stopped for a bit. Zara stayed back with her family to work at their family business in the town. Her boyfriend from highschool for many years turned out to be cheating on her repeatedly and she broke up with him. I had heard all this from my daughter Chloe, we all know how drama travels. This was just before the weekend and Zara and her ex h... continue reading
"What's up with you?" Adam asked me as we stood out on the back patio looking at storm clouds off in the distance. The clouds were almost green, which was never a good sign.
"Nothing," I quickly replied. I couldn't tell him what was actually up with me. I couldn't tell him that one week before I had fucked his sister in her bedroom. I couldn't tell him I came all over her stomach and subsequently came all over mine the next day thinking about the encounter.
"You seem weird," he said. A clap of thunder followed his rebuttal, almost as if God was trying to speak to me as well.
"I'm just a weird dude," I walked out in the yard to get a better look at the storm clouds. As I looked up at the darkening sky, Adam's mom opened up the door to let us know dinner was ready. It was a Sunday evening, and if everyone was in town, Adam and his family would get together for Sunday dinner. It usually only happened once or twice a month, since Adam and his father were tr... continue reading
Living in Southern California, I like to enjoy our many offerings that our balmy weather allows us, which often times includes hikes and trail runs. I was recently broken up with around Xmas and sowing my oats so-to-speak. One day I ended up going out for a trail run in January and at the peak was this girl. I noticed she was very long legged (like me) and lean. I mentioned something about the sunset as we were both stretching and I had my Sony A7R camera with me. She asked what I was shooting and I said nothing really, as the camera was heavy and I shouldn't have brought it on a run. Long story short we exchanged IG's and I invited her over for a photo shoot which she agreed to at the end of January (pics from that shoot posted in post history).
Based off her IG, i could tell she had a bf, so I treaded lightly, and tbh, back in Jan, I was def turned on by her during that photo shoot, but I still wasn't over my ex and bummed about that still.
We loosely kept in touch mostly thru IG... continue reading
In the summer of my 21st year, I was broke and honestly a little depressed. I was in the middle of a pretty big life transition. Stuck between taking a big risk and moving to a new city, or staying in my hometown and trying to find a safe job to settle down with. I decided to take the risk, but before I could take it, I needed to save up some money.
So during the summer, my best friend (Adam) and his family allowed me to crash at their place. They had a stable household, especially compared to mine. My father had left years ago and my mom lived with a dude I couldn't stand to be around, so I was very grateful for Adam and his family. Over the years, they had kinda become like a second family.
Adam was one year older than me and he had a younger sister named Riley. She was 18-years-old, and set to turn 19 later in the fall. She was going to a community college and working at a clothing store in town. Meanwhile, Adam was a manager at a roofing company his father owned, so they were out... continue reading
Several people recommended I share this story here too, but I'm new to this and not sure if it's allowed.
My name is Hannah. I'm in my late 20s, and I've been with my husband, John, since university. I'm 5'5, with black hair and green eyes. I'm slim, with olive toned skin, a few freckles, a great ass and breasts that are on the smaller side but still a nice handful. I go to the gym regularly. Without trying to sound full of myself, guys often try and chat me up or ask for my number or my snap when we go out to bars, or even in regular public spaces. I think it's fair to say I'm attractive.
I've been hooking up with other guys for about 8 years, ever since John admitted he had intense fantasies about sharing me. It took me a while to believe he wasn't just setting up a trap. When we finally pulled the trigger and I slept with a guy from Tinder, we both absolutely loved it and haven't stopped since.
John's best friend Cam is married, and he, his wife and us are all clo... continue reading
Good guys deserve good, regular sex. I have male friends who I know go without sex, which makes me sad.
My friend experienced the downward skid that most relationships do towards the end. Months of no regular sex before breaking up. Blowjobs probably became a myth.
After having coffee in a group (I’m quite proud of myself considering this wasn’t in an evening, alcohol fuelled setting) - I told him he should be confident in who he is and I reminded him he’s really hot.
I offered to drop him home and I found myself spontaneously ending up gazing into his eyes on his sofa. I put out there that I hadn’t had sex in a while either.
Minutes later, I took his clothes off in his bedroom and stripped for him. My lips descended from his handsome beard all the way down to a large bulge in his boxers.
I gave him the universal symbol of knowing he was about to get head. As I put my hair up, smiling, he expressed he missed blowjobs so bad. It made sealing my lips around his juicy head that much ... continue reading
My first time with a trans woman
Awhile ago, while swiping through tinder, I matched with a trans girl. I didn't notice at first because I wasn't reading profiles and she was very attractive. Let's say her name was Katie. After we matched, I went back to her profile where she mentions she's trans. I hadn't previously considered meeting up with a trans girl, as I figured it wouldn't be my thing, or I couldn't get past the obvious hurdles. However, Katie was a looker. Five foot six or so, slim, gorgeous blonde hair, big soulful eyes, pale skin. She had several photos of her wearing cute dresses on her profile.
While I'm mulling over whether to shoot my shot, she sends me a message saying that my facial hair is cute. I'm about 6'1", athletic swimmer type build, and naturally tan, but I'm horrible at talking to women so her messaging me first was greatly appreciated.
We hit it off after that, I ask for her number, and we text back and forth. The next day, I work up the courage to ask her if she'd like to meet up, and Ka... continue reading
Just skip down to the --------- for the juicy details.
This is the first time I've ever been remotely unfaithful and it is kind of getting out of control. I had to tell someone so REDDIT, here goes nothing!
A little background, I work in a small tech-sales office. I've been here for about 2 years and have always had a little crush on the office admin, Emma. She's 27, short, brunette, beautiful eyes and smile, full lips, and the best sense of humor. She's super chill, has a ton of really well done tattoos and the body of a goddess. I'm not kidding. She's a 32DD (I asked) with a flat stomach and perfectly thick ass. She hides it well but WOW her body is unbelievable.
We get along super well and have very similar taste in music, movies art, etc... So there is plenty to talk about all day. Here's the kicker though, we are both married. Because of that, I NEVER made an advance. There was always sexual tension between us but we just never even mentioned it...until... continue reading
Friday evening I broke up with my boyfriend. We were together for 3 years, but for a few weeks I had this strong urge to change something in my life. I felt so sorry for hurting him, but I knew it was the right thing to do.
Saturday evening I was invited to a house party. My Ex-boyfriend (wow, this sounds strange to me) was invited too, but luckily didn't show up.
I had lots of conversations with people I hadn't seen in a long time. It was so much fun, I played a few drinking games with them, when this hot guy suddenly showed up. We didn't know each other, but somehow connected immediately. You could tell easily that he was one of those fuckboys.
Normally I kept my distance from these kinds of men, but there was something pulling me towards him and I liked his attention. It was like he knew I was easy prey that evening. Things got flirty quickly, I got drunker and before I knew we were making out with all the other people around us. I didn't want everyone to see me doing that jus... continue reading
Accidentally sexted my best friend while riding my bf's dick
I was bouncing up and down on my bfs dick when he grabbed my phone and started to record me. Naturally my inner slut came out and I was showing off for him, rubbing my titties together while drooling on them and moaning his name so he could have something really good to look at later. I saw myself in the mirror and thought of how hot it all looked so I had him pass me the phone so I could take some pics myself.
After I finished taking the pics I started to slowly ride him while trying to quickly send him everything. I threw my phone to the side and we kept going at it...at least we tried because very quickly my phone kept lighting up and buzzing.
Frustrated I grabbed my phone and went to put it on silent when I realized it was my best friend and she was sending a ton of emoji only messages sorta like 🥵🙈👀😈😍🥴. I had to stop cause I was so confused and when I opened our messages my heart sank.
The video I had just taken riding my bfs dick moaning his name, the pics I too... continue reading
I fucked twin brothers while their mom cooked us dinner
I was dating this guy in college and he really wanted me to come to his parents house to meet them and his twin brother. We got there a couple of hours before dinner and after meeting his folks he was showing me around the house. He showed me the room that he used to share with his brother, it was a big room in the attic that didn't have a door, only stairs to get in. I was bored and horny so while we were sitting on the bed I started playing with his dick. He seemed a little apprehensive but I pointed out that his mom and dad were both in the kitchen getting dinner ready and the brother still hadn't arrived. I pulled it out and dropped to my knees.
I was getting really into the blowjob but trying to keep quiet when we heard foot steps. I jumped up quickly and he tried to shove his dick back into his pants. Thankfully, it ended up only being his brother. He had a smirk on his face.
We exchanged pleasantries for a minute or two as my boyfriend tried to hide his boner. Fina... continue reading
My best friend and I were bored, so we masturbated together
Megan and I have been best friends for about a decade now. Growing up, she lived in a neighboring town and our paths didn't cross until high school when we met through some mutual friends. She and I immediately hit it off, bonding over great conversations filled with banter, mutual interests, and some light flirtation. We felt free to talk to each other about whatever crossed our minds, including anything and everything sex related. When she lost her virginity, I took her out for ice cream to celebrate. If one of us had the hots for someone, we'd wingman each other without a second though. Most if not all of the stories I've written here she's heard and knows the details as well as I do. When she had her first threesome, she called me immediately after to give me a play-by-play, resulting in us talking about what she enjoyed and what she would change if there was another opportunity. She's texted me an album of nudes, asking which ones would be best for her "tasteful portfolio.... continue reading
I’m inspired to share this recollection in the hope of helping guys who have had anxiety struggles around erectile dysfunction / premature ejaculation.
Rewind - I slept with a guy who was quite anxious beforehand. He’d thrown into conversation that he hadn’t had sex for nearly two years. I struggled to see how, but no judgement. He was kind, had a lot going for himself and was funny.
He dropped in there that he may struggle with lose his boner but wasn’t sure.
Okay, not a problem at all.
I reassured him that I liked him, that I’m not here to judge his ‘performance’. I liked him, wanted to pleasure him and would have fun exploring each others bodies regardless.
I was told I’m not like most girls. This didn’t click at first. He was trying to tell me that I wasn’t putting excess pressure that men often face to ‘deliver’.
I suggested we could enjoy cuddling, or even some foreplay, at his pace. Despite me being VERY horny, the greater good was him feeling comfortable.
We got down to ... continue reading
My roommate pissed me off and then I came inside her
This happened back when I was 25, and was back at college on a second bachelor's degree.
I was living with a 21 year old woman we’ll call Chelle, who played soccer at the local University. We knew each other because I had played football at the same University and had some mutual friends from a few years back. We lived in a small house her parents owned, and had a third roommate who isn’t part of this story, who was never home because she was always with her boyfriend. I was single at the time and Chelle had a guy she was kinda dating.
To paint the picture Chelle was 5’6”, had dark olive skin, dark hair, B cup boobs, 6 pack abs, and an incredible ass, probably from playing soccer for years and years. I’m 6’2”, 200 lbs, brown hair, athletic and muscular from playing football and continuing to workout after football.
To put it bluntly, Chelle was a real bitch. She just wasn’t very nice to me or many others. I didn’t mind living with her because we normally kept to ourselves, ... continue reading